# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_190911_Mn_Cl
_database_code_depnum_ccdc_archive 'CCDC 2060011'
loop_
_audit_author_name
_audit_author_address
'Sotaro Kusumoto'
;Kumamoto University
Japan
;
_audit_update_record             
;
2021-03-16 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2021-03-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C18 H17 Cl Mn N3 O2'
_chemical_formula_sum            'C18 H17 Cl Mn N3 O2'
_chemical_formula_weight         397.745
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         'Mn C N O Cl'
_chemical_oxdiff_usercomment     223K
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Mn 0.34779 0.73263 11.28190 7.35730 3.01930 2.24410 5.34090 0.34320 17.86740
83.75430 1.089599967
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   7.8674(11)
_cell_length_b                   12.6283(19)
_cell_length_c                   16.991(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1688.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    696
_cell_measurement_temperature    223
_cell_measurement_theta_max      17.0610
_cell_measurement_theta_min      2.0780
_exptl_absorpt_coefficient_mu    0.957
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_description       needle
_exptl_crystal_F_000             818.291
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.1075
_diffrn_reflns_av_unetI/netI     0.1913
_diffrn_reflns_Laue_measured_fraction_full 0.9938
_diffrn_reflns_Laue_measured_fraction_max 0.9945
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8491
_diffrn_reflns_point_group_measured_fraction_full 0.9788
_diffrn_reflns_point_group_measured_fraction_max 0.9763
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.85
_diffrn_ambient_temperature      223
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.9938
_diffrn_measured_fraction_theta_max 0.9945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00  60.00   0.50   30.00    --   20.00  54.00  60.00   74
  2  ω     73.00  99.00   0.50   30.00    --   20.00  54.00  60.00   52
  3  ω    -72.00 -46.00   0.50   30.00    --   20.00  54.00-180.00   52
  4  ω    -12.00  73.00   0.50   30.00    --   20.00  54.00-180.00  170
  5  ω    -14.00  99.00   0.50   30.00    --   20.00  54.00 -60.00  226
  6  ω    -73.00 -48.00   0.50   30.00    --   20.00  54.00 -30.00   50
  7  ω    -66.00 -41.00   0.50   30.00    --   20.00  54.00   0.00   50
  8  ω    -69.00 -40.00   0.50   30.00    --   20.00  54.00  60.00   58
;
_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_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0029301000
_diffrn_orient_matrix_UB_12      -0.0559278000
_diffrn_orient_matrix_UB_13      -0.0035954000
_diffrn_orient_matrix_UB_21      0.0077855000
_diffrn_orient_matrix_UB_22      -0.0049684000
_diffrn_orient_matrix_UB_23      0.0414164000
_diffrn_orient_matrix_UB_31      -0.0897787000
_diffrn_orient_matrix_UB_32      0.0013703000
_diffrn_orient_matrix_UB_33      0.0037066000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.952
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                1851
_reflns_number_total             3375
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.8276
_refine_diff_density_min         -0.8910
_refine_diff_density_rms         0.1958
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_d_res_high            0.8001
_refine_ls_d_res_low             7.1392
_refine_ls_extinction_coef       0.0036(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   0.9422
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3375
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1414
_refine_ls_R_factor_gt           0.0701
_refine_ls_restrained_S_all      0.9422
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0355P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1391
_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:
 C5(H5), C12(H12), C2(H2), C3(H3a), C14(H14), C17(H17), C16(H16), C15(H15)
2.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Mn1 Mn 0.60099(12) 0.22523(9) 0.36502(6) 0.0254(3) Uani 1.000000 .
Cl1 Cl 0.2977(3) 0.70810(17) 0.54440(12) 0.0576(7) Uani 1.000000 .
O2 O 0.3035(5) 0.2997(4) 0.5563(2) 0.0306(12) Uani 1.000000 .
O1 O 0.5969(6) 0.3715(3) 0.3515(3) 0.0302(12) Uani 1.000000 .
N2 N 0.5247(7) 0.0752(4) 0.3552(3) 0.0228(15) Uani 1.000000 .
N3 N 0.7305(7) 0.2090(6) 0.2705(3) 0.0323(16) Uani 1.000000 .
N1 N 0.4289(6) 0.2301(5) 0.4473(3) 0.0260(13) Uani 1.000000 .
C7 C 0.3834(9) 0.3120(6) 0.4918(4) 0.0248(17) Uani 1.000000 .
C5 C 0.3596(8) 0.5029(6) 0.5096(4) 0.0278(18) Uani 1.000000 .
H5 H 0.2986(8) 0.4879(6) 0.5559(4) 0.033(2) Uiso 1.000000 R
C6 C 0.4266(8) 0.4193(5) 0.4641(4) 0.0213(17) Uani 1.000000 .
C12 C 0.6000(9) 0.0023(6) 0.3156(4) 0.0303(17) Uani 1.000000 .
H12 H 0.5560(9) -0.0667(6) 0.3197(4) 0.036(2) Uiso 1.000000 R
C18 C 0.8035(10) 0.1183(7) 0.2416(4) 0.032(2) Uani 1.000000 .
C1 C 0.5213(9) 0.4438(6) 0.3971(4) 0.0252(17) Uani 1.000000 .
C13 C 0.7441(9) 0.0166(6) 0.2661(4) 0.0296(19) Uani 1.000000 .
C2 C 0.5401(8) 0.5509(6) 0.3756(4) 0.0309(19) Uani 1.000000 .
H2 H 0.6034(8) 0.5675(6) 0.3303(4) 0.037(2) Uiso 1.000000 R
C3 C 0.4696(10) 0.6316(6) 0.4182(4) 0.033(2) Uani 1.000000 .
H3a H 0.4795(10) 0.7023(6) 0.4016(4) 0.040(2) Uiso 1.000000 R
C9 C 0.3652(9) 0.0543(5) 0.3990(4) 0.0253(17) Uani 1.000000 .
C10 C 0.2154(9) 0.0884(6) 0.3478(4) 0.040(2) Uani 1.000000 .
H10a H 0.231(3) 0.1615(12) 0.332(2) 0.060(3) Uiso 1.000000 GR
H10b H 0.210(3) 0.044(2) 0.3016(13) 0.060(3) Uiso 1.000000 GR
H10c H 0.1108(11) 0.082(3) 0.3776(9) 0.060(3) Uiso 1.000000 GR
C14 C 0.8207(10) -0.0770(7) 0.2332(4) 0.038(2) Uani 1.000000 .
H14 H 0.7828(10) -0.1443(7) 0.2491(4) 0.045(3) Uiso 1.000000 R
C11 C 0.3438(10) -0.0620(5) 0.4248(4) 0.040(2) Uani 1.000000 .
H11a H 0.327(5) -0.1062(7) 0.3787(5) 0.060(3) Uiso 1.000000 GR
H11b H 0.445(3) -0.0850(12) 0.453(2) 0.060(3) Uiso 1.000000 GR
H11c H 0.246(4) -0.0681(8) 0.459(2) 0.060(3) Uiso 1.000000 GR
C17 C 0.9323(10) 0.1224(7) 0.1846(4) 0.042(2) Uani 1.000000 .
H17 H 0.9712(10) 0.1884(7) 0.1663(4) 0.050(3) Uiso 1.000000 R
C4 C 0.3834(10) 0.6061(6) 0.4866(4) 0.0306(19) Uani 1.000000 .
C8 C 0.3782(10) 0.1232(5) 0.4727(4) 0.0260(18) Uani 1.000000 .
H8a H 0.4629(10) 0.0939(5) 0.5089(4) 0.031(2) Uiso 1.000000 R
H8b H 0.2683(10) 0.1258(5) 0.4998(4) 0.031(2) Uiso 1.000000 R
C16 C 1.0028(10) 0.0298(8) 0.1549(4) 0.050(3) Uani 1.000000 .
H16 H 1.0902(10) 0.0344(8) 0.1174(4) 0.060(3) Uiso 1.000000 R
C15 C 0.9483(10) -0.0684(8) 0.1789(5) 0.048(2) Uani 1.000000 .
H15 H 0.9988(10) -0.1298(8) 0.1580(5) 0.058(3) Uiso 1.000000 R
H3 H 0.779(9) 0.270(7) 0.251(4) 0.07(3) Uiso 1.000000 .


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 O2 2.103(4) 2_556 ?
Mn1 O1 1.861(4) . ?
Mn1 N2 1.994(5) . ?
Mn1 N3 1.913(6) . ?
Mn1 N1 1.947(5) . ?
Cl1 C4 1.755(7) . ?
O2 C7 1.273(7) . ?
O1 C1 1.337(7) . ?
N2 C12 1.285(7) . ?
N2 C9 1.484(8) . ?
N3 C18 1.372(10) . ?
N3 H3 0.92(8) . ?
N1 C7 1.329(8) . ?
N1 C8 1.473(8) . ?
C7 C6 1.475(9) . ?
C5 H5 0.9400 . ?
C5 C6 1.410(8) . ?
C5 C4 1.374(9) . ?
C6 C1 1.395(9) . ?
C12 H12 0.9400 . ?
C12 C13 1.423(9) . ?
C18 C13 1.428(10) . ?
C18 C17 1.403(9) . ?
C1 C2 1.409(9) . ?
C13 C14 1.440(10) . ?
C2 H2 0.9400 . ?
C2 C3 1.368(8) . ?
C3 H3a 0.9400 . ?
C3 C4 1.383(9) . ?
C9 C10 1.527(9) . ?
C9 C11 1.542(8) . ?
C9 C8 1.528(8) . ?
C10 H10a 0.9700 . ?
C10 H10b 0.9700 . ?
C10 H10c 0.9700 . ?
C14 H14 0.9400 . ?
C14 C15 1.368(10) . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C11 H11c 0.9700 . ?
C17 H17 0.9400 . ?
C17 C16 1.390(10) . ?
C8 H8a 0.9800 . ?
C8 H8b 0.9800 . ?
C16 H16 0.9400 . ?
C16 C15 1.374(10) . ?
C15 H15 0.9400 . ?

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 103.9(2) . 2_556 ?
N2 Mn1 O2 98.0(2) . 2_556 ?
N2 Mn1 O1 158.0(2) . . ?
N3 Mn1 O2 96.5(2) . 2_556 ?
N3 Mn1 O1 90.7(3) . . ?
N3 Mn1 N2 89.3(3) . . ?
N1 Mn1 O2 94.33(18) . 2_556 ?
N1 Mn1 O1 92.6(2) . . ?
N1 Mn1 N2 83.2(2) . . ?
N1 Mn1 N3 167.5(2) . . ?
C7 O2 Mn1 159.9(4) . 2_456 ?
C1 O1 Mn1 127.9(4) . . ?
C12 N2 Mn1 125.9(5) . . ?
C9 N2 Mn1 112.5(4) . . ?
C9 N2 C12 121.7(6) . . ?
C18 N3 Mn1 127.8(6) . . ?
H3 N3 Mn1 115(5) . . ?
H3 N3 C18 113(5) . . ?
C7 N1 Mn1 128.3(5) . . ?
C8 N1 Mn1 111.7(4) . . ?
C8 N1 C7 118.3(5) . . ?
N1 C7 O2 121.9(6) . . ?
C6 C7 O2 120.0(7) . . ?
C6 C7 N1 118.1(6) . . ?
C6 C5 H5 119.9(4) . . ?
C4 C5 H5 119.9(4) . . ?
C4 C5 C6 120.1(6) . . ?
C5 C6 C7 115.2(6) . . ?
C1 C6 C7 125.9(6) . . ?
C1 C6 C5 118.8(6) . . ?
H12 C12 N2 117.1(4) . . ?
C13 C12 N2 125.8(7) . . ?
C13 C12 H12 117.1(5) . . ?
C13 C18 N3 120.6(7) . . ?
C17 C18 N3 121.2(8) . . ?
C17 C18 C13 118.1(8) . . ?
C6 C1 O1 124.0(7) . . ?
C2 C1 O1 117.3(6) . . ?
C2 C1 C6 118.7(7) . . ?
C18 C13 C12 123.2(7) . . ?
C14 C13 C12 117.2(7) . . ?
C14 C13 C18 119.2(7) . . ?
H2 C2 C1 118.8(4) . . ?
C3 C2 C1 122.4(7) . . ?
C3 C2 H2 118.8(4) . . ?
H3a C3 C2 121.0(4) . . ?
C4 C3 C2 118.0(7) . . ?
C4 C3 H3a 121.0(4) . . ?
C10 C9 N2 108.4(5) . . ?
C11 C9 N2 113.9(6) . . ?
C11 C9 C10 110.3(6) . . ?
C8 C9 N2 104.7(5) . . ?
C8 C9 C10 111.0(6) . . ?
C8 C9 C11 108.5(5) . . ?
H10a C10 C9 109.5 . . ?
H10b C10 C9 109.5 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 C9 109.5 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
H14 C14 C13 119.9(5) . . ?
C15 C14 C13 120.2(9) . . ?
C15 C14 H14 119.9(6) . . ?
H11a C11 C9 109.5 . . ?
H11b C11 C9 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C9 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
H17 C17 C18 119.8(5) . . ?
C16 C17 C18 120.5(8) . . ?
C16 C17 H17 119.8(5) . . ?
C5 C4 Cl1 119.0(6) . . ?
C3 C4 Cl1 119.2(6) . . ?
C3 C4 C5 121.8(7) . . ?
C9 C8 N1 107.5(5) . . ?
H8a C8 N1 110.2(4) . . ?
H8a C8 C9 110.2(4) . . ?
H8b C8 N1 110.2(4) . . ?
H8b C8 C9 110.2(4) . . ?
H8b C8 H8a 108.5 . . ?
H16 C16 C17 119.1(5) . . ?
C15 C16 C17 121.9(8) . . ?
C15 C16 H16 119.1(5) . . ?
C16 C15 C14 120.1(9) . . ?
H15 C15 C14 120.0(6) . . ?
H15 C15 C16 120.0(5) . . ?


_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 3.652
_oxdiff_exptl_absorpt_empirical_full_min 0.618
####################################################################### 
# 
# 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_190925_Mn_Br
_database_code_depnum_ccdc_archive 'CCDC 2060014'
loop_
_audit_author_name
_audit_author_address
'Sotaro Kusumoto'
;Kumamoto University
Japan
;
_audit_update_record             
;
2021-03-16 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2021-03-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C18 H17 Br Mn N3 O2'
_chemical_formula_sum            'C18 H17 Br Mn N3 O2'
_chemical_formula_weight         442.196
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         'Mn C N O Br'
_chemical_oxdiff_usercomment     223K
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Mn 0.34779 0.73263 11.28190 7.35730 3.01930 2.24410 5.34090 0.34320 17.86740
83.75430 1.089599967
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   7.9237(4)
_cell_length_b                   12.7678(5)
_cell_length_c                   17.3798(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1758.28(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3098
_cell_measurement_temperature    223
_cell_measurement_theta_max      26.6910
_cell_measurement_theta_min      2.3460
_exptl_absorpt_coefficient_mu    3.039
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_description       plate
_exptl_crystal_F_000             888.907
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 0.9956
_diffrn_reflns_Laue_measured_fraction_max 0.9961
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9062
_diffrn_reflns_point_group_measured_fraction_full 0.9547
_diffrn_reflns_point_group_measured_fraction_max 0.9477
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.34
_diffrn_ambient_temperature      223
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9956
_diffrn_measured_fraction_theta_max 0.9961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  95.00   0.50   30.00    --   20.00  54.00 -30.00  206
  2  ω    -74.00  53.00   0.50   30.00    --   20.00  54.00 -90.00  254
  3  ω     85.00 110.00   0.50   30.00    --   20.00  54.00 -90.00   50
  4  ω     10.00  35.00   0.50   30.00    --   20.00  54.00-150.00   50
  5  ω     75.00 100.00   0.50   30.00    --   20.00  54.00-150.00   50
  6  ω    -68.00 -38.00   0.50   30.00    --   20.00  54.00 -60.00   60
  7  ω    -67.00 -39.00   0.50   30.00    --   20.00  54.00 -30.00   56
;
_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      0.0035721000
_diffrn_orient_matrix_UB_12      -0.0060414000
_diffrn_orient_matrix_UB_13      -0.0405210000
_diffrn_orient_matrix_UB_21      0.0042997000
_diffrn_orient_matrix_UB_22      -0.0551922000
_diffrn_orient_matrix_UB_23      0.0045474000
_diffrn_orient_matrix_UB_31      -0.0892963000
_diffrn_orient_matrix_UB_32      -0.0029373000
_diffrn_orient_matrix_UB_33      -0.0013868000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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         0.882
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                2872
_reflns_number_total             3405
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.7735
_refine_diff_density_min         -0.4547
_refine_diff_density_rms         0.1112
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.030(13)
_refine_ls_d_res_high            0.8004
_refine_ls_d_res_low             8.6899
_refine_ls_goodness_of_fit_ref   1.0272
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    29
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3405
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.0272
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0194P)²+0.7660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0691
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(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:
 N3(H3), C5(H5), C12(H12), C2(H2), C17(H17), C14(H14), C15(H15), C3(H3a),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Br1 Br 0.70343(6) -0.19613(3) 0.62415(3) 0.04322(15) Uani 1.000000 .
Mn1 Mn 0.37160(7) 0.34529(4) 0.60931(3) 0.02034(14) Uani 1.000000 .
O2 O 0.6953(4) 0.1653(2) 0.47923(15) 0.0372(7) Uani 1.000000 .
O1 O 0.3535(3) 0.21937(19) 0.66347(14) 0.0256(7) Uani 1.000000 .
N2 N 0.4658(4) 0.4831(2) 0.57792(19) 0.0231(8) Uani 1.000000 .
N1 N 0.5520(4) 0.2913(3) 0.54468(19) 0.0258(8) Uani 1.000000 .
N3 N 0.2302(4) 0.4140(2) 0.68296(18) 0.0250(8) Uani 1.000000 .
H3 H 0.1810(4) 0.3717(2) 0.71509(18) 0.0300(10) Uiso 1.000000 R
C6 C 0.5516(5) 0.1126(3) 0.5915(2) 0.0221(9) Uani 1.000000 .
C7 C 0.6032(5) 0.1928(3) 0.5348(2) 0.0231(9) Uani 1.000000 .
C5 C 0.6259(5) 0.0134(3) 0.5843(2) 0.0258(10) Uani 1.000000 .
H5 H 0.7028(5) 0.0010(3) 0.5441(2) 0.0310(11) Uiso 1.000000 R
C1 C 0.4371(5) 0.1297(3) 0.6520(2) 0.0200(9) Uani 1.000000 .
C12 C 0.4061(5) 0.5744(3) 0.5971(2) 0.0254(10) Uani 1.000000 .
H12 H 0.4557(5) 0.6327(3) 0.5730(2) 0.0304(12) Uiso 1.000000 R
C2 C 0.4013(5) 0.0459(3) 0.7027(2) 0.0262(10) Uani 1.000000 .
H2 H 0.3241(5) 0.0563(3) 0.7430(2) 0.0314(12) Uiso 1.000000 R
C9 C 0.6221(5) 0.4757(3) 0.5295(2) 0.0264(10) Uani 1.000000 .
C18 C 0.1926(5) 0.5162(3) 0.6944(2) 0.0230(9) Uani 1.000000 .
C13 C 0.2746(5) 0.5959(3) 0.6502(2) 0.0249(9) Uani 1.000000 .
C17 C 0.0781(5) 0.5495(3) 0.7511(3) 0.0324(11) Uani 1.000000 .
H17 H 0.0249(5) 0.4991(3) 0.7822(3) 0.0388(13) Uiso 1.000000 R
C8 C 0.6070(6) 0.3701(3) 0.4887(2) 0.0296(11) Uani 1.000000 .
H8a H 0.7164(6) 0.3500(3) 0.4668(2) 0.0355(13) Uiso 1.000000 R
H8b H 0.5249(6) 0.3750(3) 0.4467(2) 0.0355(13) Uiso 1.000000 R
C4 C 0.5889(5) -0.0656(3) 0.6344(2) 0.0256(10) Uani 1.000000 .
C14 C 0.2327(6) 0.7021(3) 0.6632(3) 0.0380(12) Uani 1.000000 .
H14 H 0.2841(6) 0.7542(3) 0.6330(3) 0.0456(14) Uiso 1.000000 R
C15 C 0.1200(6) 0.7308(3) 0.7184(3) 0.0439(13) Uani 1.000000 .
H15 H 0.0951(6) 0.8019(3) 0.7269(3) 0.0527(15) Uiso 1.000000 R
C3 C 0.4761(5) -0.0502(3) 0.6943(2) 0.0277(10) Uani 1.000000 .
H3a H 0.4514(5) -0.1049(3) 0.7288(2) 0.0332(12) Uiso 1.000000 R
C10 C 0.7740(6) 0.4764(4) 0.5842(3) 0.0417(12) Uani 1.000000 .
H10a H 0.775(2) 0.5412(10) 0.6133(12) 0.0625(19) Uiso 1.000000 GR
H10b H 0.7659(19) 0.4175(13) 0.6193(11) 0.0625(19) Uiso 1.000000 GR
H10c H 0.8774(6) 0.471(2) 0.5545(3) 0.0625(19) Uiso 1.000000 GR
C11 C 0.6386(6) 0.5615(3) 0.4690(2) 0.0377(12) Uani 1.000000 .
H11a H 0.5338(13) 0.5673(15) 0.4405(11) 0.0566(18) Uiso 1.000000 GR
H11b H 0.663(3) 0.6277(5) 0.4942(3) 0.0566(18) Uiso 1.000000 GR
H11c H 0.730(2) 0.5443(11) 0.4340(10) 0.0566(18) Uiso 1.000000 GR
C16 C 0.0418(6) 0.6529(4) 0.7624(3) 0.0382(11) Uani 1.000000 .
H16 H -0.0369(6) 0.6721(4) 0.8004(3) 0.0459(13) Uiso 1.000000 R


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
Br1 C4 1.906(4) . ?
Mn1 O2 2.083(3) 2_456 ?
Mn1 O1 1.869(2) . ?
Mn1 N2 1.988(3) . ?
Mn1 N1 1.945(3) . ?
Mn1 N3 1.914(3) . ?
O2 C7 1.260(4) . ?
O1 C1 1.337(4) . ?
N2 C12 1.301(5) . ?
N2 C9 1.501(5) . ?
N1 C7 1.332(5) . ?
N1 C8 1.465(5) . ?
N3 H3 0.8700 . ?
N3 C18 1.353(4) . ?
C6 C7 1.480(5) . ?
C6 C5 1.403(5) . ?
C6 C1 1.406(5) . ?
C5 H5 0.9400 . ?
C5 C4 1.365(5) . ?
C1 C2 1.415(5) . ?
C12 H12 0.9400 . ?
C12 C13 1.420(5) . ?
C2 H2 0.9400 . ?
C2 C3 1.370(6) . ?
C9 C8 1.528(5) . ?
C9 C10 1.534(6) . ?
C9 C11 1.524(5) . ?
C18 C13 1.430(5) . ?
C18 C17 1.406(5) . ?
C13 C14 1.415(5) . ?
C17 H17 0.9400 . ?
C17 C16 1.366(6) . ?
C8 H8a 0.9800 . ?
C8 H8b 0.9800 . ?
C4 C3 1.386(5) . ?
C14 H14 0.9400 . ?
C14 C15 1.361(6) . ?
C15 H15 0.9400 . ?
C15 C16 1.399(6) . ?
C3 H3a 0.9400 . ?
C10 H10a 0.9700 . ?
C10 H10b 0.9700 . ?
C10 H10c 0.9700 . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C11 H11c 0.9700 . ?
C16 H16 0.9400 . ?

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 105.37(11) . 2_456 ?
N2 Mn1 O2 96.10(12) . 2_456 ?
N2 Mn1 O1 158.25(13) . . ?
N1 Mn1 O2 92.49(13) . 2_456 ?
N1 Mn1 O1 92.42(12) . . ?
N1 Mn1 N2 83.07(14) . . ?
N3 Mn1 O2 97.54(13) . 2_456 ?
N3 Mn1 O1 90.73(12) . . ?
N3 Mn1 N2 89.84(13) . . ?
N3 Mn1 N1 168.29(14) . . ?
C7 O2 Mn1 166.5(3) . 2_556 ?
C1 O1 Mn1 128.6(2) . . ?
C12 N2 Mn1 125.9(3) . . ?
C9 N2 Mn1 114.1(2) . . ?
C9 N2 C12 120.0(3) . . ?
C7 N1 Mn1 129.3(3) . . ?
C8 N1 Mn1 111.0(3) . . ?
C8 N1 C7 118.1(3) . . ?
H3 N3 Mn1 113.99(9) . . ?
C18 N3 Mn1 132.0(3) . . ?
C18 N3 H3 114.0(2) . . ?
C5 C6 C7 116.7(4) . . ?
C1 C6 C7 124.7(3) . . ?
C1 C6 C5 118.7(4) . . ?
N1 C7 O2 122.6(4) . . ?
C6 C7 O2 118.5(4) . . ?
C6 C7 N1 118.9(4) . . ?
H5 C5 C6 119.4(2) . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5 119.4(2) . . ?
C6 C1 O1 124.4(3) . . ?
C2 C1 O1 117.1(3) . . ?
C2 C1 C6 118.4(3) . . ?
H12 C12 N2 116.3(2) . . ?
C13 C12 N2 127.3(4) . . ?
C13 C12 H12 116.3(2) . . ?
H2 C2 C1 119.2(2) . . ?
C3 C2 C1 121.7(4) . . ?
C3 C2 H2 119.2(3) . . ?
C8 C9 N2 104.6(3) . . ?
C10 C9 N2 107.4(3) . . ?
C10 C9 C8 110.7(3) . . ?
C11 C9 N2 114.3(4) . . ?
C11 C9 C8 108.8(3) . . ?
C11 C9 C10 110.8(4) . . ?
C13 C18 N3 120.5(3) . . ?
C17 C18 N3 122.5(4) . . ?
C17 C18 C13 117.0(4) . . ?
C18 C13 C12 123.1(3) . . ?
C14 C13 C12 117.5(4) . . ?
C14 C13 C18 119.3(4) . . ?
H17 C17 C18 119.0(2) . . ?
C16 C17 C18 122.0(4) . . ?
C16 C17 H17 119.0(3) . . ?
C9 C8 N1 108.8(3) . . ?
H8a C8 N1 109.9(2) . . ?
H8a C8 C9 109.9(2) . . ?
H8b C8 N1 109.9(2) . . ?
H8b C8 C9 109.9(2) . . ?
H8b C8 H8a 108.3 . . ?
C5 C4 Br1 118.9(3) . . ?
C3 C4 Br1 120.1(3) . . ?
C3 C4 C5 120.9(3) . . ?
H14 C14 C13 119.2(2) . . ?
C15 C14 C13 121.6(4) . . ?
C15 C14 H14 119.2(3) . . ?
H15 C15 C14 120.5(3) . . ?
C16 C15 C14 119.0(4) . . ?
C16 C15 H15 120.5(3) . . ?
C4 C3 C2 119.0(4) . . ?
H3a C3 C2 120.5(3) . . ?
H3a C3 C4 120.5(2) . . ?
H10a C10 C9 109.5 . . ?
H10b C10 C9 109.5 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 C9 109.5 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
H11a C11 C9 109.5 . . ?
H11b C11 C9 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C9 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
C15 C16 C17 121.0(4) . . ?
H16 C16 C17 119.5(3) . . ?
H16 C16 C15 119.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C4 C5 C6 -176.8(3) . . . . ?
Br1 C4 C3 C2 177.0(3) . . . . ?
Mn1 O2 C7 N1 33.8(12) 2_556 . . . ?
Mn1 O2 C7 C6 -145.5(11) 2_556 . . . ?
Mn1 O1 C1 C6 -3.9(3) . . . . ?
Mn1 O1 C1 C2 178.9(3) . . . . ?
Mn1 N2 C12 C13 7.3(4) . . . . ?
Mn1 N2 C9 C8 27.2(3) . . . . ?
Mn1 N2 C9 C10 -90.5(3) . . . . ?
Mn1 N2 C9 C11 146.1(3) . . . . ?
Mn1 N1 C7 O2 163.8(3) . . . . ?
Mn1 N1 C7 C6 -16.9(4) . . . . ?
Mn1 N1 C8 C9 43.8(3) . . . . ?
Mn1 N3 C18 C13 -5.2(4) . . . . ?
Mn1 N3 C18 C17 177.3(4) . . . . ?
O2 C7 N1 C8 -0.5(5) . . . . ?
O2 C7 C6 C5 7.4(4) . . . . ?
O2 C7 C6 C1 -173.8(3) . . . . ?
O1 C1 C6 C7 3.7(5) . . . . ?
O1 C1 C6 C5 -177.5(4) . . . . ?
O1 C1 C2 C3 177.9(3) . . . . ?
N2 C12 C13 C18 3.3(5) . . . . ?
N2 C12 C13 C14 178.8(4) . . . . ?
N2 C9 C8 N1 -44.4(3) . . . . ?
N1 C7 C6 C5 -172.0(4) . . . . ?
N1 C7 C6 C1 6.8(4) . . . . ?
N1 C8 C9 C10 71.0(4) . . . . ?
N1 C8 C9 C11 -166.9(4) . . . . ?
N3 C18 C13 C12 -4.7(4) . . . . ?
N3 C18 C13 C14 179.9(4) . . . . ?
N3 C18 C17 C16 179.6(4) . . . . ?
C6 C5 C4 C3 0.0(5) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
C5 C4 C3 C2 0.2(5) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C12 C13 C18 C17 172.9(4) . . . . ?
C12 C13 C14 C15 -173.6(4) . . . . ?
C18 C13 C14 C15 2.1(5) . . . . ?
C18 C17 C16 C15 -1.1(5) . . . . ?
C13 C14 C15 C16 -1.1(5) . . . . ?
C17 C16 C15 C14 0.5(5) . . . . ?


_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 1.771
_oxdiff_exptl_absorpt_empirical_full_min 0.760
####################################################################### 
# 
# 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_180523_MnL-Cl
_database_code_depnum_ccdc_archive 'CCDC 2060012'
loop_
_audit_author_name
_audit_author_address
'Sotaro Kusumoto'
;Kumamoto University
Japan
;
_audit_update_record             
;
2021-03-16 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2021-03-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C18 H17 Cl Mn N3 O2'
_chemical_formula_sum            'C18 H17 Cl Mn N3 O2'
_chemical_formula_weight         397.745
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         C21O2Mn1N3Cl1
_chemical_oxdiff_usercomment     173K
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Mn 0.34779 0.73263 11.28190 7.35730 3.01930 2.24410 5.34090 0.34320 17.86740
83.75430 1.089599967
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   7.8303(3)
_cell_length_b                   12.6301(6)
_cell_length_c                   17.0111(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1682.35(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2246
_cell_measurement_temperature    120
_cell_measurement_theta_max      23.5410
_cell_measurement_theta_min      2.3870
_exptl_absorpt_coefficient_mu    0.960
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_description       plate
_exptl_crystal_F_000             818.291
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0758
_diffrn_reflns_Laue_measured_fraction_full 0.9994
_diffrn_reflns_Laue_measured_fraction_max 0.9995
_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       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8774
_diffrn_reflns_point_group_measured_fraction_full 0.9203
_diffrn_reflns_point_group_measured_fraction_max 0.9071
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.39
_diffrn_ambient_temperature      120
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     12.00  38.00   0.50   25.00    --   20.00  54.00-150.00   52
  2  ω     43.00  69.00   0.50   25.00    --   20.00  54.00-150.00   52
  3  ω    -71.00 103.00   0.50   25.00    --   20.00  54.00  90.00  348
  4  ω     45.00 106.00   0.50   25.00    --   20.00  54.00 -30.00  122
  5  ω    -56.00 -31.00   0.50   25.00    --   20.00  54.00-180.00   50
  6  ω     18.00  43.00   0.50   25.00    --   20.00  54.00-180.00   50
  7  ω    -24.00   1.00   0.50   25.00    --   20.00  54.00-150.00   50
;
_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_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0562096000
_diffrn_orient_matrix_UB_12      0.0051308000
_diffrn_orient_matrix_UB_13      -0.0324752000
_diffrn_orient_matrix_UB_21      -0.0194502000
_diffrn_orient_matrix_UB_22      0.0525538000
_diffrn_orient_matrix_UB_23      0.0117313000
_diffrn_orient_matrix_UB_31      0.0682107000
_diffrn_orient_matrix_UB_32      0.0192103000
_diffrn_orient_matrix_UB_33      -0.0234014000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.781
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                2560
_reflns_number_total             3123
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.5349
_refine_diff_density_min         -0.5278
_refine_diff_density_rms         0.1033
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_d_res_high            0.8001
_refine_ls_d_res_low             8.5055
_refine_ls_goodness_of_fit_ref   1.0078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.0078
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0937
_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:
 C5(H5), C12(H12), C3(H3a), C2(H2), C17(H17), 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_primary     dual
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_refinement_flags_posn
Mn1 Mn 0.39889(7) 0.77481(5) 0.63541(3) 0.01704(16) Uani 1.000000 .
Cl1 Cl 0.70326(15) 0.29087(9) 0.45585(7) 0.0400(3) Uani 1.000000 .
O2 O 0.6949(3) 0.6992(2) 0.44258(15) 0.0225(6) Uani 1.000000 .
O1 O 0.4035(4) 0.62825(19) 0.64904(15) 0.0226(7) Uani 1.000000 .
N1 N 0.5702(4) 0.7705(2) 0.55253(18) 0.0180(7) Uani 1.000000 .
N2 N 0.4751(4) 0.9246(2) 0.6452(2) 0.0186(8) Uani 1.000000 .
N3 N 0.2688(4) 0.7929(3) 0.7302(2) 0.0234(8) Uani 1.000000 .
C7 C 0.6154(5) 0.6885(3) 0.5075(2) 0.0179(9) Uani 1.000000 .
C5 C 0.6399(5) 0.4958(3) 0.4903(2) 0.0208(9) Uani 1.000000 .
H5 H 0.7001(5) 0.5104(3) 0.4444(2) 0.0249(11) Uiso 1.000000 R
C6 C 0.5735(5) 0.5798(3) 0.5349(2) 0.0154(9) Uani 1.000000 .
C12 C 0.3987(5) 0.9984(3) 0.6848(2) 0.0231(9) Uani 1.000000 .
H12 H 0.4422(5) 1.0667(3) 0.6801(2) 0.0277(11) Uiso 1.000000 R
C3 C 0.5320(5) 0.3680(3) 0.5827(3) 0.0238(10) Uani 1.000000 .
H3a H 0.5225(5) 0.2982(3) 0.5995(3) 0.0285(12) Uiso 1.000000 R
C2 C 0.4622(5) 0.4490(3) 0.6260(2) 0.0215(9) Uani 1.000000 .
H2 H 0.4021(5) 0.4326(3) 0.6716(2) 0.0259(11) Uiso 1.000000 R
C18 C 0.1968(5) 0.8829(4) 0.7583(2) 0.0228(10) Uani 1.000000 .
C4 C 0.6174(5) 0.3923(3) 0.5132(2) 0.0222(9) Uani 1.000000 .
C1 C 0.4786(5) 0.5554(3) 0.6038(2) 0.0183(9) Uani 1.000000 .
C11 C 0.6600(6) 1.0613(3) 0.5744(3) 0.0282(11) Uani 1.000000 .
H11a H 0.5600(15) 1.0837(7) 0.5463(13) 0.0423(17) Uiso 1.000000 GR
H11b H 0.676(3) 1.1057(4) 0.6195(3) 0.0423(17) Uiso 1.000000 GR
H11c H 0.758(2) 1.0664(5) 0.5406(12) 0.0423(17) Uiso 1.000000 GR
C17 C 0.0667(5) 0.8791(4) 0.8163(2) 0.0290(11) Uani 1.000000 .
H17 H 0.0292(5) 0.8139(4) 0.8349(2) 0.0348(13) Uiso 1.000000 R
C9 C 0.6373(5) 0.9463(3) 0.6010(2) 0.0212(9) Uani 1.000000 .
C13 C 0.2542(5) 0.9847(3) 0.7348(2) 0.0227(10) Uani 1.000000 .
C16 C -0.0046(6) 0.9703(4) 0.8454(2) 0.0336(12) Uani 1.000000 .
H16 H -0.0911(6) 0.9651(4) 0.8827(2) 0.0403(15) Uiso 1.000000 R
C10 C 0.7863(5) 0.9113(4) 0.6511(2) 0.0294(11) Uani 1.000000 .
H10a H 0.794(2) 0.9557(13) 0.6968(8) 0.0441(17) Uiso 1.000000 GR
H10b H 0.7697(17) 0.8391(7) 0.6671(13) 0.0441(17) Uiso 1.000000 GR
H10c H 0.8899(7) 0.917(2) 0.6213(5) 0.0441(17) Uiso 1.000000 GR
C8 C 0.6205(6) 0.8768(3) 0.5272(2) 0.0215(10) Uani 1.000000 .
H8a H 0.7286(6) 0.8740(3) 0.4994(2) 0.0258(12) Uiso 1.000000 R
H8b H 0.5350(6) 0.9061(3) 0.4921(2) 0.0258(12) Uiso 1.000000 R
C14 C 0.1780(5) 1.0766(4) 0.7672(3) 0.0299(11) Uani 1.000000 .
H14 H 0.2171(5) 1.1428(4) 0.7514(3) 0.0359(13) Uiso 1.000000 R
C15 C 0.0486(6) 1.0706(4) 0.8210(3) 0.0330(12) Uani 1.000000 .
H15 H -0.0025(6) 1.1315(4) 0.8407(3) 0.0396(14) Uiso 1.000000 R
H3 H 0.227(5) 0.737(4) 0.750(2) 0.031(13) Uiso 1.000000 .


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 O2 2.102(3) 2_466 ?
Mn1 O1 1.866(3) . ?
Mn1 N1 1.947(3) . ?
Mn1 N2 1.991(3) . ?
Mn1 N3 1.921(3) . ?
Cl1 C4 1.745(4) . ?
O2 C7 1.275(4) . ?
O1 C1 1.336(4) . ?
N1 C7 1.336(4) . ?
N1 C8 1.465(5) . ?
N2 C12 1.296(5) . ?
N2 C9 1.500(5) . ?
N3 C18 1.356(5) . ?
N3 H3 0.84(4) . ?
C7 C6 1.486(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.404(5) . ?
C5 C4 1.376(5) . ?
C6 C1 1.421(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.427(5) . ?
C3 H3a 0.9300 . ?
C3 C2 1.374(5) . ?
C3 C4 1.392(5) . ?
C2 H2 0.9300 . ?
C2 C1 1.403(5) . ?
C18 C17 1.419(5) . ?
C18 C13 1.420(6) . ?
C11 H11a 0.9600 . ?
C11 H11b 0.9600 . ?
C11 H11c 0.9600 . ?
C11 C9 1.532(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.372(6) . ?
C9 C10 1.510(5) . ?
C9 C8 1.538(5) . ?
C13 C14 1.417(6) . ?
C16 H16 0.9300 . ?
C16 C15 1.398(6) . ?
C10 H10a 0.9600 . ?
C10 H10b 0.9600 . ?
C10 H10c 0.9600 . ?
C8 H8a 0.9700 . ?
C8 H8b 0.9700 . ?
C14 H14 0.9300 . ?
C14 C15 1.367(6) . ?
C15 H15 0.9300 . ?

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 104.35(12) . 2_466 ?
N1 Mn1 O2 94.07(11) . 2_466 ?
N1 Mn1 O1 92.80(12) . . ?
N2 Mn1 O2 97.58(12) . 2_466 ?
N2 Mn1 O1 157.94(13) . . ?
N2 Mn1 N1 83.14(14) . . ?
N3 Mn1 O2 96.22(13) . 2_466 ?
N3 Mn1 O1 91.36(14) . . ?
N3 Mn1 N1 167.60(14) . . ?
N3 Mn1 N2 88.63(15) . . ?
C7 O2 Mn1 159.1(3) . 2_566 ?
C1 O1 Mn1 128.3(3) . . ?
C7 N1 Mn1 128.3(3) . . ?
C8 N1 Mn1 111.9(2) . . ?
C8 N1 C7 118.1(3) . . ?
C12 N2 Mn1 126.0(3) . . ?
C9 N2 Mn1 112.6(2) . . ?
C9 N2 C12 121.3(3) . . ?
C18 N3 Mn1 128.0(3) . . ?
H3 N3 Mn1 116(3) . . ?
H3 N3 C18 113(3) . . ?
N1 C7 O2 122.9(3) . . ?
C6 C7 O2 118.5(3) . . ?
C6 C7 N1 118.6(3) . . ?
C6 C5 H5 119.4(2) . . ?
C4 C5 H5 119.4(2) . . ?
C4 C5 C6 121.2(4) . . ?
C5 C6 C7 116.5(4) . . ?
C1 C6 C7 125.0(3) . . ?
C1 C6 C5 118.4(3) . . ?
H12 C12 N2 117.0(2) . . ?
C13 C12 N2 126.0(4) . . ?
C13 C12 H12 117.0(2) . . ?
C2 C3 H3a 120.6(2) . . ?
C4 C3 H3a 120.6(2) . . ?
C4 C3 C2 118.9(4) . . ?
H2 C2 C3 118.9(2) . . ?
C1 C2 C3 122.1(4) . . ?
C1 C2 H2 118.9(2) . . ?
C17 C18 N3 121.1(4) . . ?
C13 C18 N3 121.9(4) . . ?
C13 C18 C17 117.0(4) . . ?
C5 C4 Cl1 119.3(3) . . ?
C3 C4 Cl1 119.9(3) . . ?
C3 C4 C5 120.7(4) . . ?
C6 C1 O1 123.8(4) . . ?
C2 C1 O1 117.6(4) . . ?
C2 C1 C6 118.6(3) . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
C9 C11 H11a 109.5 . . ?
C9 C11 H11b 109.5 . . ?
C9 C11 H11c 109.5 . . ?
H17 C17 C18 119.5(3) . . ?
C16 C17 C18 121.0(4) . . ?
C16 C17 H17 119.5(3) . . ?
C11 C9 N2 114.8(3) . . ?
C10 C9 N2 108.6(3) . . ?
C10 C9 C11 110.8(3) . . ?
C8 C9 N2 103.4(3) . . ?
C8 C9 C11 108.0(3) . . ?
C8 C9 C10 111.1(3) . . ?
C18 C13 C12 122.0(4) . . ?
C14 C13 C12 117.8(4) . . ?
C14 C13 C18 119.9(4) . . ?
H16 C16 C17 118.9(3) . . ?
C15 C16 C17 122.2(4) . . ?
C15 C16 H16 118.9(3) . . ?
H10a C10 C9 109.5 . . ?
H10b C10 C9 109.5 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 C9 109.5 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
C9 C8 N1 107.8(3) . . ?
H8a C8 N1 110.1(2) . . ?
H8a C8 C9 110.1(2) . . ?
H8b C8 N1 110.1(2) . . ?
H8b C8 C9 110.1(2) . . ?
H8b C8 H8a 108.5 . . ?
H14 C14 C13 119.1(3) . . ?
C15 C14 C13 121.8(5) . . ?
C15 C14 H14 119.1(3) . . ?
C14 C15 C16 118.0(4) . . ?
H15 C15 C16 121.0(3) . . ?
H15 C15 C14 121.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 O2 C7 N1 77.3(7) 2_566 . . . ?
Mn1 O2 C7 C6 -101.7(7) 2_566 . . . ?
Mn1 O1 C1 C6 0.7(3) . . . . ?
Mn1 O1 C1 C2 -179.3(3) . . . . ?
Mn1 N1 C7 O2 161.3(3) . . . . ?
Mn1 N1 C7 C6 -19.7(3) . . . . ?
Mn1 N1 C8 C9 41.4(2) . . . . ?
Mn1 N2 C12 C13 6.1(4) . . . . ?
Mn1 N2 C9 C11 153.5(3) . . . . ?
Mn1 N2 C9 C10 -82.0(3) . . . . ?
Mn1 N2 C9 C8 36.1(3) . . . . ?
Mn1 N3 C18 C17 162.3(3) . . . . ?
Mn1 N3 C18 C13 -21.5(4) . . . . ?
Cl1 C4 C5 C6 -179.7(3) . . . . ?
Cl1 C4 C3 C2 -178.6(3) . . . . ?
O2 C7 N1 C8 -2.4(5) . . . . ?
O2 C7 C6 C5 6.0(4) . . . . ?
O2 C7 C6 C1 -176.8(3) . . . . ?
O1 C1 C6 C7 5.7(5) . . . . ?
O1 C1 C6 C5 -177.2(4) . . . . ?
O1 C1 C2 C3 178.8(3) . . . . ?
N1 C7 C6 C5 -173.1(4) . . . . ?
N1 C7 C6 C1 4.1(5) . . . . ?
N1 C8 C9 N2 -48.6(3) . . . . ?
N1 C8 C9 C11 -170.6(3) . . . . ?
N1 C8 C9 C10 67.7(4) . . . . ?
N2 C12 C13 C18 12.2(5) . . . . ?
N2 C12 C13 C14 -173.9(4) . . . . ?
N3 C18 C17 C16 179.2(4) . . . . ?
N3 C18 C13 C12 -4.7(5) . . . . ?
N3 C18 C13 C14 -178.4(4) . . . . ?
C7 C6 C5 C4 176.0(3) . . . . ?
C7 C6 C1 C2 -174.3(4) . . . . ?
C5 C6 C1 C2 2.8(4) . . . . ?
C5 C4 C3 C2 3.5(5) . . . . ?
C6 C1 C2 C3 -1.2(4) . . . . ?
C12 C13 C18 C17 171.7(4) . . . . ?
C12 C13 C14 C15 -174.3(4) . . . . ?
C18 C17 C16 C15 -1.2(5) . . . . ?
C18 C13 C14 C15 -0.2(5) . . . . ?
C17 C16 C15 C14 -1.1(5) . . . . ?
C13 C14 C15 C16 1.8(5) . . . . ?


_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 1.171
_oxdiff_exptl_absorpt_empirical_full_min 0.853
####################################################################### 
# 
# 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_190822Mn-I-h
_database_code_depnum_ccdc_archive 'CCDC 2060015'
loop_
_audit_author_name
_audit_author_address
'Sotaro Kusumoto'
;Kumamoto University
Japan
;
_audit_update_record             
;
2021-03-16 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2021-03-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C18 H17 I Mn N3 O2'
_chemical_formula_sum            'C18 H17 I Mn N3 O2'
_chemical_formula_weight         489.197
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         'Mn N O I C'
_chemical_oxdiff_usercomment     '223 K'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Mn 0.34779 0.73263 11.28190 7.35730 3.01930 2.24410 5.34090 0.34320 17.86740
83.75430 1.089599967
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   9.5006(4)
_cell_length_b                   10.4519(4)
_cell_length_c                   17.3947(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1727.28(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5049
_cell_measurement_temperature    223
_cell_measurement_theta_max      30.6590
_cell_measurement_theta_min      2.3250
_exptl_absorpt_coefficient_mu    2.568
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.881
_exptl_crystal_description       block
_exptl_crystal_F_000             960.173
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.9978
_diffrn_reflns_Laue_measured_fraction_max 0.9980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9519
_diffrn_reflns_point_group_measured_fraction_full 0.9770
_diffrn_reflns_point_group_measured_fraction_max 0.9725
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.27
_diffrn_ambient_temperature      223
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.9980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00 -11.00   0.50    7.00    --   20.00  54.00-150.00   52
  2  ω     33.00  59.00   0.50    7.00    --   20.00  54.00-150.00   52
  3  ω     68.00  94.00   0.50    7.00    --   20.00  54.00-150.00   52
  4  ω    -35.00  55.00   0.50    7.00    --   20.00  54.00-180.00  180
  5  ω     60.00  86.00   0.50    7.00    --   20.00  54.00-180.00   52
  6  ω    -73.00 -44.00   0.50    7.00    --   20.00  54.00  60.00   58
  7  ω    -69.00 103.00   0.50    7.00    --   20.00  54.00  90.00  344
;
_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      0.0111724000
_diffrn_orient_matrix_UB_12      0.0621541000
_diffrn_orient_matrix_UB_13      0.0152894000
_diffrn_orient_matrix_UB_21      -0.0079330000
_diffrn_orient_matrix_UB_22      -0.0246439000
_diffrn_orient_matrix_UB_23      0.0377175000
_diffrn_orient_matrix_UB_31      0.0733692000
_diffrn_orient_matrix_UB_32      -0.0120681000
_diffrn_orient_matrix_UB_33      0.0018665000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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         0.938
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                3332
_reflns_number_total             3427
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.4141
_refine_diff_density_min         -0.4846
_refine_diff_density_rms         0.0854
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.011(17)
_refine_ls_d_res_high            0.8002
_refine_ls_d_res_low             8.9590
_refine_ls_goodness_of_fit_ref   1.0394
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3427
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0191
_refine_ls_restrained_S_all      1.0394
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0295P)²+0.5943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0490
_refine_ls_wR_factor_ref         0.0494
_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:
 C12(H12), C3(H3a), C5(H5), C14(H14), C15(H15), C17(H17), C16(H16), C2(H2)
2.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
I1 I 0.88057(2) -0.029160(19) 0.191222(10) 0.03303(6) Uani 1.000000 .
Mn1 Mn 0.55123(4) 0.40564(4) 0.48830(2) 0.01957(9) Uani 1.000000 .
O2 O 0.9472(2) 0.2465(2) 0.45538(11) 0.0260(4) Uani 1.000000 .
N2 N 0.6121(2) 0.50702(19) 0.57931(12) 0.0199(4) Uani 1.000000 .
O1 O 0.5409(2) 0.3663(2) 0.38361(11) 0.0265(4) Uani 1.000000 .
N3 N 0.3855(3) 0.5098(2) 0.48087(13) 0.0251(5) Uani 1.000000 .
N1 N 0.7394(2) 0.3321(2) 0.49684(14) 0.0251(5) Uani 1.000000 .
C13 C 0.4127(3) 0.6518(3) 0.58913(15) 0.0211(5) Uani 1.000000 .
C9 C 0.7568(3) 0.4742(3) 0.60820(15) 0.0230(5) Uani 1.000000 .
C7 C 0.8187(3) 0.2764(3) 0.44436(16) 0.0206(6) Uani 1.000000 .
C18 C 0.3327(3) 0.6013(3) 0.52700(15) 0.0207(5) Uani 1.000000 .
C12 C 0.5480(3) 0.6043(3) 0.60896(15) 0.0229(5) Uani 1.000000 .
H12 H 0.5962(3) 0.6485(3) 0.64796(15) 0.0275(6) Uiso 1.000000 R
C1 C 0.6204(3) 0.2849(2) 0.34471(14) 0.0222(5) Uani 1.000000 .
C3 C 0.6408(3) 0.1532(3) 0.23034(16) 0.0299(6) Uani 1.000000 .
H3a H 0.6020(3) 0.1224(3) 0.18421(16) 0.0359(8) Uiso 1.000000 R
C5 C 0.8289(3) 0.1557(3) 0.32273(15) 0.0240(6) Uani 1.000000 .
H5 H 0.9185(3) 0.1278(3) 0.33818(15) 0.0287(7) Uiso 1.000000 R
C14 C 0.3589(3) 0.7539(3) 0.63298(16) 0.0280(6) Uani 1.000000 .
H14 H 0.4140(3) 0.7880(3) 0.67287(16) 0.0336(7) Uiso 1.000000 R
C15 C 0.2287(3) 0.8048(3) 0.61922(17) 0.0292(6) Uani 1.000000 .
H15 H 0.1943(3) 0.8730(3) 0.64894(17) 0.0351(8) Uiso 1.000000 R
C17 C 0.1977(3) 0.6545(3) 0.51516(17) 0.0256(6) Uani 1.000000 .
H17 H 0.1406(3) 0.6218(3) 0.47566(17) 0.0307(7) Uiso 1.000000 R
C16 C 0.1480(3) 0.7523(3) 0.55958(17) 0.0273(6) Uani 1.000000 .
H16 H 0.0576(3) 0.7852(3) 0.54994(17) 0.0328(7) Uiso 1.000000 R
C6 C 0.7543(3) 0.2428(3) 0.36895(15) 0.0207(5) Uani 1.000000 .
C2 C 0.5686(3) 0.2405(3) 0.27402(16) 0.0281(6) Uani 1.000000 .
H2 H 0.4818(3) 0.2715(3) 0.25607(16) 0.0337(7) Uiso 1.000000 R
C10 C 0.8604(3) 0.5733(3) 0.5772(2) 0.0392(8) Uani 1.000000 .
H10a H 0.8612(19) 0.5699(16) 0.5215(2) 0.0588(11) Uiso 1.000000 GR
H10b H 0.8318(14) 0.6579(4) 0.5939(12) 0.0588(11) Uiso 1.000000 GR
H10c H 0.9539(5) 0.5549(14) 0.5966(11) 0.0588(11) Uiso 1.000000 GR
C4 C 0.7718(3) 0.1108(3) 0.25486(16) 0.0270(6) Uani 1.000000 .
C11 C 0.7617(3) 0.4685(3) 0.69533(17) 0.0357(6) Uani 1.000000 .
H11a H 0.733(2) 0.5505(8) 0.71635(17) 0.0536(10) Uiso 1.000000 GR
H11b H 0.6980(19) 0.4025(16) 0.71344(18) 0.0536(10) Uiso 1.000000 GR
H11c H 0.8568(6) 0.449(2) 0.71189(18) 0.0536(10) Uiso 1.000000 GR
C8 C 0.7918(3) 0.3433(3) 0.57629(17) 0.0307(6) Uani 1.000000 .
H8a H 0.7484(3) 0.2771(3) 0.60840(17) 0.0369(8) Uiso 1.000000 R
H8b H 0.8940(3) 0.3304(3) 0.57706(17) 0.0369(8) Uiso 1.000000 R
H3 H 0.330(3) 0.490(3) 0.4520(17) 0.019(8) Uiso 1.000000 .


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
I1 C4 2.106(3) . ?
Mn1 O2 2.113(2) 2_456 ?
Mn1 N2 1.991(2) . ?
Mn1 O1 1.8695(19) . ?
Mn1 N3 1.918(2) . ?
Mn1 N1 1.952(2) . ?
O2 C7 1.275(3) . ?
N2 C9 1.504(3) . ?
N2 C12 1.292(3) . ?
O1 C1 1.324(3) . ?
N3 C18 1.346(3) . ?
N3 H3 0.76(3) . ?
N1 C7 1.319(4) . ?
N1 C8 1.474(4) . ?
C13 C18 1.422(4) . ?
C13 C12 1.421(4) . ?
C13 C14 1.408(4) . ?
C9 C10 1.526(4) . ?
C9 C11 1.517(4) . ?
C9 C8 1.514(4) . ?
C7 C6 1.489(4) . ?
C18 C17 1.413(4) . ?
C12 H12 0.9400 . ?
C1 C6 1.411(4) . ?
C1 C2 1.403(4) . ?
C3 H3a 0.9400 . ?
C3 C2 1.371(4) . ?
C3 C4 1.388(4) . ?
C5 H5 0.9400 . ?
C5 C6 1.405(4) . ?
C5 C4 1.381(4) . ?
C14 H14 0.9400 . ?
C14 C15 1.368(4) . ?
C15 H15 0.9400 . ?
C15 C16 1.402(4) . ?
C17 H17 0.9400 . ?
C17 C16 1.366(4) . ?
C16 H16 0.9400 . ?
C2 H2 0.9400 . ?
C10 H10a 0.9700 . ?
C10 H10b 0.9700 . ?
C10 H10c 0.9700 . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C11 H11c 0.9700 . ?
C8 H8a 0.9800 . ?
C8 H8b 0.9800 . ?

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
N2 Mn1 O2 99.65(8) . 2_456 ?
O1 Mn1 O2 105.17(8) . 2_456 ?
O1 Mn1 N2 155.08(9) . . ?
N3 Mn1 O2 94.25(9) . 2_456 ?
N3 Mn1 N2 89.43(9) . . ?
N3 Mn1 O1 90.93(9) . . ?
N1 Mn1 O2 95.58(9) . 2_456 ?
N1 Mn1 N2 83.27(9) . . ?
N1 Mn1 O1 92.04(9) . . ?
N1 Mn1 N3 168.61(10) . . ?
C7 O2 Mn1 134.62(18) . 2_556 ?
C9 N2 Mn1 114.21(16) . . ?
C12 N2 Mn1 126.78(18) . . ?
C12 N2 C9 118.5(2) . . ?
C1 O1 Mn1 127.56(17) . . ?
C18 N3 Mn1 132.01(19) . . ?
H3 N3 Mn1 117(2) . . ?
H3 N3 C18 109(2) . . ?
C7 N1 Mn1 130.1(2) . . ?
C8 N1 Mn1 110.48(18) . . ?
C8 N1 C7 119.4(2) . . ?
C12 C13 C18 122.6(2) . . ?
C14 C13 C18 119.9(2) . . ?
C14 C13 C12 117.5(2) . . ?
C10 C9 N2 108.5(2) . . ?
C11 C9 N2 111.8(2) . . ?
C11 C9 C10 111.1(3) . . ?
C8 C9 N2 106.5(2) . . ?
C8 C9 C10 110.0(2) . . ?
C8 C9 C11 108.9(3) . . ?
N1 C7 O2 123.4(3) . . ?
C6 C7 O2 117.9(2) . . ?
C6 C7 N1 118.7(2) . . ?
C13 C18 N3 121.2(2) . . ?
C17 C18 N3 122.1(2) . . ?
C17 C18 C13 116.7(2) . . ?
C13 C12 N2 127.2(2) . . ?
H12 C12 N2 116.40(15) . . ?
H12 C12 C13 116.40(15) . . ?
C6 C1 O1 124.2(2) . . ?
C2 C1 O1 117.4(3) . . ?
C2 C1 C6 118.4(3) . . ?
C2 C3 H3a 120.31(17) . . ?
C4 C3 H3a 120.31(17) . . ?
C4 C3 C2 119.4(3) . . ?
C6 C5 H5 119.63(16) . . ?
C4 C5 H5 119.63(17) . . ?
C4 C5 C6 120.7(3) . . ?
H14 C14 C13 119.05(16) . . ?
C15 C14 C13 121.9(3) . . ?
C15 C14 H14 119.05(18) . . ?
H15 C15 C14 120.90(18) . . ?
C16 C15 C14 118.2(3) . . ?
C16 C15 H15 120.90(17) . . ?
H17 C17 C18 119.12(16) . . ?
C16 C17 C18 121.8(3) . . ?
C16 C17 H17 119.12(17) . . ?
C17 C16 C15 121.5(3) . . ?
H16 C16 C15 119.27(17) . . ?
H16 C16 C17 119.27(17) . . ?
C1 C6 C7 124.0(2) . . ?
C5 C6 C7 116.7(2) . . ?
C5 C6 C1 119.0(2) . . ?
C3 C2 C1 122.0(3) . . ?
H2 C2 C1 118.98(17) . . ?
H2 C2 C3 118.98(17) . . ?
H10a C10 C9 109.5 . . ?
H10b C10 C9 109.5 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 C9 109.5 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
C3 C4 I1 120.0(2) . . ?
C5 C4 I1 119.5(2) . . ?
C5 C4 C3 120.4(3) . . ?
H11a C11 C9 109.5 . . ?
H11b C11 C9 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C9 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
C9 C8 N1 109.9(2) . . ?
H8a C8 N1 109.68(16) . . ?
H8a C8 C9 109.68(16) . . ?
H8b C8 N1 109.68(15) . . ?
H8b C8 C9 109.68(16) . . ?
H8b C8 H8a 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C4 C3 C2 177.3(2) . . . . ?
I1 C4 C5 C6 -175.7(2) . . . . ?
Mn1 O2 C7 N1 79.5(3) 2_556 . . . ?
Mn1 O2 C7 C6 -98.6(3) 2_556 . . . ?
Mn1 N2 C9 C10 99.2(2) . . . . ?
Mn1 N2 C9 C11 -138.1(2) . . . . ?
Mn1 N2 C9 C8 -19.22(18) . . . . ?
Mn1 N2 C12 C13 7.7(3) . . . . ?
Mn1 O1 C1 C6 -20.9(2) . . . . ?
Mn1 O1 C1 C2 160.6(2) . . . . ?
Mn1 N3 C18 C13 10.3(3) . . . . ?
Mn1 N3 C18 C17 -171.4(2) . . . . ?
Mn1 N1 C7 O2 171.0(2) . . . . ?
Mn1 N1 C7 C6 -10.9(3) . . . . ?
Mn1 N1 C8 C9 -42.58(19) . . . . ?
O2 C7 N1 C8 -10.0(3) . . . . ?
O2 C7 C6 C1 -171.0(2) . . . . ?
O2 C7 C6 C5 14.1(3) . . . . ?
N2 C9 C8 N1 38.9(2) . . . . ?
N2 C12 C13 C18 -5.4(3) . . . . ?
N2 C12 C13 C14 175.5(3) . . . . ?
O1 C1 C6 C7 5.1(3) . . . . ?
O1 C1 C6 C5 179.9(3) . . . . ?
O1 C1 C2 C3 -178.1(2) . . . . ?
N3 C18 C13 C12 -3.7(3) . . . . ?
N3 C18 C13 C14 175.4(3) . . . . ?
N3 C18 C17 C16 -176.3(3) . . . . ?
N1 C7 C6 C1 10.8(3) . . . . ?
N1 C7 C6 C5 -164.1(3) . . . . ?
N1 C8 C9 C10 -78.5(3) . . . . ?
N1 C8 C9 C11 159.6(2) . . . . ?
C13 C18 C17 C16 2.0(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C7 C6 C1 C2 -176.5(3) . . . . ?
C7 C6 C5 C4 174.6(2) . . . . ?
C18 C17 C16 C15 0.0(3) . . . . ?
C1 C6 C5 C4 -0.6(3) . . . . ?
C1 C2 C3 C4 -2.6(3) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C14 C15 C16 C17 -1.1(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 1.573
_oxdiff_exptl_absorpt_empirical_full_min 0.777
####################################################################### 
# 
# 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_190525_Mn-I_5
_database_code_depnum_ccdc_archive 'CCDC 2060016'
loop_
_audit_author_name
_audit_author_address
'Sotaro Kusumoto'
;Kumamoto University
Japan
;
_audit_update_record             
;
2021-03-16 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2021-03-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C18 H17 I Mn N3 O2'
_chemical_formula_sum            'C18 H17 I Mn N3 O2'
_chemical_formula_weight         489.197
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         'Mn C N O I'
_chemical_oxdiff_usercomment     '120 K'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Mn 0.34779 0.73263 11.28190 7.35730 3.01930 2.24410 5.34090 0.34320 17.86740
83.75430 1.089599967
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   9.5303(3)
_cell_length_b                   10.3905(3)
_cell_length_c                   17.3403(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1717.12(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5453
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.0690
_cell_measurement_theta_min      2.3520
_exptl_absorpt_coefficient_mu    2.584
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.892
_exptl_crystal_description       block
_exptl_crystal_F_000             960.173
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-10 -10 3 0.1431
1 0 -24 0.0512
-2 0 24 0.0489
-13 2 0 0.1850
0 15 -2 0.0994
11 8 -3 0.1283
11 -9 -1 0.1446
-1 -15 2 0.1074

_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.111
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-10.0132 -9.5554 3.4300 0.2369 0.7290 0.6422
1.0359 -0.1526 -24.3727 0.8996 -0.4005 -0.1738
-1.9623 0.3158 24.1799 -0.8863 0.3946 0.2425
-13.2623 2.3336 -0.3683 0.1025 -0.0456 0.9937
-0.3921 14.5920 -2.0186 -0.3040 -0.9357 0.1789
11.3620 7.5538 -3.4189 -0.1999 -0.6153 -0.7625
10.6974 -8.8418 -0.9239 0.1457 0.4486 -0.8818
-0.5317 -14.5775 2.2061 0.3071 0.9452 -0.1104

_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.9983
_diffrn_reflns_Laue_measured_fraction_max 0.9985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10300
_diffrn_reflns_point_group_measured_fraction_full 0.9743
_diffrn_reflns_point_group_measured_fraction_max 0.9669
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.35
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     65.00 102.00   0.50    3.00    --   20.00  54.00 -90.00   74
  2  ω    -74.00 -26.00   0.50    3.00    --   20.00  54.00 150.00   96
  3  ω      5.00  35.00   0.50    3.00    --   20.00  54.00 150.00   60
  4  ω    -74.00 107.00   0.50    3.00    --   20.00  54.00 120.00  362
  5  ω    -64.00 -39.00   0.50    3.00    --   20.00  54.00-150.00   50
  6  ω    -36.00 -11.00   0.50    3.00    --   20.00  54.00-150.00   50
  7  ω     34.00  67.00   0.50    3.00    --   20.00  54.00-150.00   66
  8  ω    -22.00  25.00   0.50    3.00    --   20.00  54.00 -90.00   94
;
_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      -0.0113202000
_diffrn_orient_matrix_UB_12      -0.0262898000
_diffrn_orient_matrix_UB_13      -0.0372285000
_diffrn_orient_matrix_UB_21      -0.0079368000
_diffrn_orient_matrix_UB_22      -0.0620580000
_diffrn_orient_matrix_UB_23      0.0164855000
_diffrn_orient_matrix_UB_31      -0.0731279000
_diffrn_orient_matrix_UB_32      0.0108410000
_diffrn_orient_matrix_UB_33      0.0039543000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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         0.924
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                3198
_reflns_number_total             3388
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.2960
_refine_diff_density_min         -0.4275
_refine_diff_density_rms         0.0872
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_d_res_high            0.8002
_refine_ls_d_res_low             8.6701
_refine_ls_goodness_of_fit_ref   1.0370
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0220
_refine_ls_restrained_S_all      1.0370
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0150P)²+0.6302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0416
_refine_ls_wR_factor_ref         0.0424
_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:
 C15(H15), C12(H12), C3(H3a), C14(H14), C16(H16), C17(H17), C5(H5), C2(H2)
2.c Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C10(H10a,H10b,H10c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
I1 I 0.11733(2) -0.03308(2) 0.189841(12) 0.01808(6) Uani 1.000000 .
Mn1 Mn 0.44822(5) 0.40499(5) 0.48853(3) 0.01146(11) Uani 1.000000 .
O2 O 0.0504(2) 0.2491(2) 0.45464(12) 0.0144(5) Uani 1.000000 .
O1 O 0.4585(2) 0.3665(2) 0.38313(12) 0.0155(5) Uani 1.000000 .
N2 N 0.3879(3) 0.5079(2) 0.58005(13) 0.0119(5) Uani 1.000000 .
N3 N 0.6147(3) 0.5090(2) 0.48128(14) 0.0147(6) Uani 1.000000 .
N1 N 0.2595(3) 0.3323(2) 0.49633(15) 0.0125(6) Uani 1.000000 .
C15 C 0.7721(3) 0.8078(3) 0.61910(19) 0.0160(8) Uani 1.000000 .
H15 H 0.8066(3) 0.8780(3) 0.64869(19) 0.0192(9) Uiso 1.000000 R
C13 C 0.5883(3) 0.6529(3) 0.58984(17) 0.0122(7) Uani 1.000000 .
C12 C 0.4519(3) 0.6066(3) 0.60958(18) 0.0143(7) Uani 1.000000 .
H12 H 0.4029(3) 0.6529(3) 0.64840(18) 0.0171(8) Uiso 1.000000 R
C18 C 0.6683(3) 0.6017(3) 0.52720(17) 0.0123(7) Uani 1.000000 .
C3 C 0.3577(3) 0.1497(3) 0.22924(18) 0.0182(8) Uani 1.000000 .
H3a H 0.3970(3) 0.1172(3) 0.18282(18) 0.0218(9) Uiso 1.000000 R
C9 C 0.2426(3) 0.4772(3) 0.60877(17) 0.0145(7) Uani 1.000000 .
C14 C 0.6425(3) 0.7568(3) 0.63323(18) 0.0173(7) Uani 1.000000 .
H14 H 0.5870(3) 0.7923(3) 0.67348(18) 0.0208(9) Uiso 1.000000 R
C7 C 0.1795(3) 0.2775(3) 0.44354(18) 0.0119(7) Uani 1.000000 .
C11 C 0.2386(3) 0.4704(3) 0.69683(17) 0.0187(7) Uani 1.000000 .
H11a H 0.3088(14) 0.4085(14) 0.71494(18) 0.0280(10) Uiso 1.000000 GR
H11b H 0.259(2) 0.5555(5) 0.71834(17) 0.0280(10) Uiso 1.000000 GR
H11c H 0.1451(7) 0.4428(18) 0.71365(17) 0.0280(10) Uiso 1.000000 GR
C10 C 0.1400(3) 0.5775(3) 0.57834(19) 0.0195(8) Uani 1.000000 .
H10a H 0.1706(12) 0.6634(4) 0.5944(10) 0.0293(12) Uiso 1.000000 GR
H10b H 0.1371(16) 0.5733(13) 0.5219(2) 0.0293(12) Uiso 1.000000 GR
H10c H 0.0462(5) 0.5603(12) 0.5991(9) 0.0293(12) Uiso 1.000000 GR
C16 C 0.8532(3) 0.7537(3) 0.55967(18) 0.0154(7) Uani 1.000000 .
H16 H 0.9444(3) 0.7868(3) 0.54996(18) 0.0185(9) Uiso 1.000000 R
C17 C 0.8035(3) 0.6541(3) 0.51521(19) 0.0136(7) Uani 1.000000 .
H17 H 0.8613(3) 0.6197(3) 0.47560(19) 0.0163(8) Uiso 1.000000 R
C1 C 0.3784(3) 0.2838(3) 0.34387(17) 0.0133(6) Uani 1.000000 .
C5 C 0.1694(3) 0.1562(3) 0.32123(18) 0.0144(7) Uani 1.000000 .
H5 H 0.0782(3) 0.1297(3) 0.33650(18) 0.0173(8) Uiso 1.000000 R
C2 C 0.4306(3) 0.2382(3) 0.27299(19) 0.0182(8) Uani 1.000000 .
H2 H 0.5184(3) 0.2692(3) 0.25479(19) 0.0218(9) Uiso 1.000000 R
C8 C 0.2059(3) 0.3448(3) 0.57596(18) 0.0150(7) Uani 1.000000 .
H8a H 0.1027(3) 0.3333(3) 0.57611(18) 0.0180(9) Uiso 1.000000 R
H8b H 0.2476(3) 0.2769(3) 0.60878(18) 0.0180(9) Uiso 1.000000 R
C4 C 0.2261(3) 0.1084(3) 0.25375(18) 0.0159(7) Uani 1.000000 .
C6 C 0.2440(3) 0.2435(3) 0.36782(18) 0.0132(7) Uani 1.000000 .
H3 H 0.666(3) 0.486(3) 0.4504(15) 0.004(8) Uiso 1.000000 .


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
I1 C4 2.113(3) . ?
Mn1 O2 2.117(2) 2_556 ?
Mn1 O1 1.874(2) . ?
Mn1 N2 1.998(2) . ?
Mn1 N3 1.924(3) . ?
Mn1 N1 1.955(3) . ?
O2 C7 1.280(4) . ?
O1 C1 1.335(4) . ?
N2 C12 1.299(4) . ?
N2 C9 1.506(4) . ?
N3 C18 1.350(4) . ?
N3 H3 0.77(3) . ?
N1 C7 1.320(4) . ?
N1 C8 1.478(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.366(4) . ?
C15 C16 1.405(4) . ?
C13 C12 1.427(4) . ?
C13 C18 1.430(4) . ?
C13 C14 1.414(4) . ?
C12 H12 0.9500 . ?
C18 C17 1.415(4) . ?
C3 H3a 0.9500 . ?
C3 C2 1.380(4) . ?
C3 C4 1.392(4) . ?
C9 C11 1.529(4) . ?
C9 C10 1.523(4) . ?
C9 C8 1.529(4) . ?
C14 H14 0.9500 . ?
C7 C6 1.492(4) . ?
C11 H11a 0.9800 . ?
C11 H11b 0.9800 . ?
C11 H11c 0.9800 . ?
C10 H10a 0.9800 . ?
C10 H10b 0.9800 . ?
C10 H10c 0.9800 . ?
C16 H16 0.9500 . ?
C16 C17 1.375(4) . ?
C17 H17 0.9500 . ?
C1 C2 1.408(4) . ?
C1 C6 1.410(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.381(4) . ?
C5 C6 1.407(4) . ?
C2 H2 0.9500 . ?
C8 H8a 0.9900 . ?
C8 H8b 0.9900 . ?

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 105.58(9) . 2_556 ?
N2 Mn1 O2 99.63(9) . 2_556 ?
N2 Mn1 O1 154.70(10) . . ?
N3 Mn1 O2 94.36(10) . 2_556 ?
N3 Mn1 O1 90.76(10) . . ?
N3 Mn1 N2 89.35(11) . . ?
N1 Mn1 O2 95.66(10) . 2_556 ?
N1 Mn1 O1 91.89(10) . . ?
N1 Mn1 N2 83.52(11) . . ?
N1 Mn1 N3 168.55(11) . . ?
C7 O2 Mn1 133.3(2) . 2_456 ?
C1 O1 Mn1 127.23(19) . . ?
C12 N2 Mn1 126.9(2) . . ?
C9 N2 Mn1 114.46(19) . . ?
C9 N2 C12 118.0(3) . . ?
C18 N3 Mn1 132.4(2) . . ?
H3 N3 Mn1 114(2) . . ?
H3 N3 C18 113(2) . . ?
C7 N1 Mn1 130.5(2) . . ?
C8 N1 Mn1 110.41(19) . . ?
C8 N1 C7 119.1(3) . . ?
C14 C15 H15 120.9(2) . . ?
C16 C15 H15 120.87(19) . . ?
C16 C15 C14 118.3(3) . . ?
C18 C13 C12 122.8(3) . . ?
C14 C13 C12 117.5(3) . . ?
C14 C13 C18 119.6(3) . . ?
C13 C12 N2 126.8(3) . . ?
H12 C12 N2 116.59(17) . . ?
H12 C12 C13 116.59(18) . . ?
C13 C18 N3 120.8(3) . . ?
C17 C18 N3 122.2(3) . . ?
C17 C18 C13 117.0(3) . . ?
C2 C3 H3a 120.29(19) . . ?
C4 C3 H3a 120.29(19) . . ?
C4 C3 C2 119.4(3) . . ?
C11 C9 N2 111.3(2) . . ?
C10 C9 N2 109.3(3) . . ?
C10 C9 C11 111.2(3) . . ?
C8 C9 N2 106.1(2) . . ?
C8 C9 C11 108.9(3) . . ?
C8 C9 C10 109.8(2) . . ?
C13 C14 C15 122.1(3) . . ?
H14 C14 C15 119.0(2) . . ?
H14 C14 C13 118.96(18) . . ?
N1 C7 O2 123.4(3) . . ?
C6 C7 O2 118.3(3) . . ?
C6 C7 N1 118.3(3) . . ?
H11a C11 C9 109.5 . . ?
H11b C11 C9 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C9 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
H10a C10 C9 109.5 . . ?
H10b C10 C9 109.5 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 C9 109.5 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
H16 C16 C15 119.21(19) . . ?
C17 C16 C15 121.6(3) . . ?
C17 C16 H16 119.21(19) . . ?
C16 C17 C18 121.4(3) . . ?
H17 C17 C18 119.31(18) . . ?
H17 C17 C16 119.31(19) . . ?
C2 C1 O1 117.4(3) . . ?
C6 C1 O1 124.0(3) . . ?
C6 C1 C2 118.6(3) . . ?
C4 C5 H5 119.31(18) . . ?
C6 C5 H5 119.31(18) . . ?
C6 C5 C4 121.4(3) . . ?
C1 C2 C3 121.8(3) . . ?
H2 C2 C3 119.12(19) . . ?
H2 C2 C1 119.12(19) . . ?
C9 C8 N1 110.3(3) . . ?
H8a C8 N1 109.59(16) . . ?
H8a C8 C9 109.59(16) . . ?
H8b C8 N1 109.59(17) . . ?
H8b C8 C9 109.59(17) . . ?
H8b C8 H8a 108.1 . . ?
C3 C4 I1 119.8(2) . . ?
C5 C4 I1 120.2(2) . . ?
C5 C4 C3 120.0(3) . . ?
C1 C6 C7 124.3(3) . . ?
C5 C6 C7 116.7(3) . . ?
C5 C6 C1 118.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C4 C3 C2 -177.4(2) . . . . ?
I1 C4 C5 C6 175.4(2) . . . . ?
Mn1 O2 C7 N1 -79.7(3) 2_456 . . . ?
Mn1 O2 C7 C6 98.5(3) 2_456 . . . ?
Mn1 O1 C1 C2 -159.8(2) . . . . ?
Mn1 O1 C1 C6 22.4(3) . . . . ?
Mn1 N2 C12 C13 -9.0(3) . . . . ?
Mn1 N2 C9 C11 137.5(2) . . . . ?
Mn1 N2 C9 C10 -99.3(2) . . . . ?
Mn1 N2 C9 C8 19.14(19) . . . . ?
Mn1 N3 C18 C13 -9.7(3) . . . . ?
Mn1 N3 C18 C17 171.5(3) . . . . ?
Mn1 N1 C7 O2 -170.6(3) . . . . ?
Mn1 N1 C7 C6 11.2(3) . . . . ?
Mn1 N1 C8 C9 42.0(2) . . . . ?
O2 C7 N1 C8 9.4(4) . . . . ?
O2 C7 C6 C1 171.2(3) . . . . ?
O2 C7 C6 C5 -14.7(3) . . . . ?
O1 C1 C2 C3 178.0(3) . . . . ?
O1 C1 C6 C7 -6.3(4) . . . . ?
O1 C1 C6 C5 179.8(3) . . . . ?
N2 C12 C13 C18 6.7(4) . . . . ?
N2 C12 C13 C14 -175.5(3) . . . . ?
N2 C9 C8 N1 -38.5(2) . . . . ?
N3 C18 C13 C12 2.7(4) . . . . ?
N3 C18 C13 C14 -175.0(3) . . . . ?
N3 C18 C17 C16 176.0(3) . . . . ?
N1 C7 C6 C1 -10.5(4) . . . . ?
N1 C7 C6 C5 163.6(3) . . . . ?
N1 C8 C9 C11 -158.4(2) . . . . ?
N1 C8 C9 C10 79.6(3) . . . . ?
C15 C14 C13 C12 179.7(3) . . . . ?
C15 C14 C13 C18 -2.4(4) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C13 C18 C17 C16 -2.8(3) . . . . ?
C3 C2 C1 C6 -4.1(4) . . . . ?
C3 C4 C5 C6 -2.1(4) . . . . ?
C7 C6 C1 C2 176.0(3) . . . . ?
C7 C6 C5 C4 -173.4(3) . . . . ?
C1 C6 C5 C4 1.0(4) . . . . ?


_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 1.193
_oxdiff_exptl_absorpt_empirical_full_min 0.885
####################################################################### 
# 
# 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_190725_Mn_Br_3
_database_code_depnum_ccdc_archive 'CCDC 2060013'
loop_
_audit_author_name
_audit_author_address
'Sotaro Kusumoto'
;Kumamoto University
Japan
;
_audit_update_record             
;
2021-03-16 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2021-03-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C18 H17 Br Mn N3 O2'
_chemical_formula_sum            'C18 H17 Br Mn N3 O2'
_chemical_formula_weight         442.196
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         'Mn C N Br O'
_chemical_oxdiff_usercomment     120K
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Mn 0.34779 0.73263 11.28190 7.35730 3.01930 2.24410 5.34090 0.34320 17.86740
83.75430 1.089599967
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   7.8656(7)
_cell_length_b                   12.7295(6)
_cell_length_c                   17.3852(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1740.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3140
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.2750
_cell_measurement_theta_min      2.0690
_exptl_absorpt_coefficient_mu    3.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_description       plate
_exptl_crystal_F_000             888.907
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.9973
_diffrn_reflns_Laue_measured_fraction_max 0.9976
_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       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10734
_diffrn_reflns_point_group_measured_fraction_full 0.9930
_diffrn_reflns_point_group_measured_fraction_max 0.9913
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.84
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.9976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  87.00   0.50   15.00    --   20.00  54.00  30.00  322
  2  ω    -73.00 107.00   0.50   15.00    --   20.00  54.00 -30.00  360
  3  ω     24.00  49.00   0.50   15.00    --   20.00  54.00-180.00   50
  4  ω     58.00  83.00   0.50   15.00    --   20.00  54.00-180.00   50
  5  ω     22.00  47.00   0.50   15.00    --   20.00  54.00-150.00   50
  6  ω     30.00  55.00   0.50   15.00    --   20.00  54.00 120.00   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      -0.0045244000
_diffrn_orient_matrix_UB_12      -0.0448169000
_diffrn_orient_matrix_UB_13      -0.0241344000
_diffrn_orient_matrix_UB_21      -0.0109779000
_diffrn_orient_matrix_UB_22      0.0330376000
_diffrn_orient_matrix_UB_23      -0.0324590000
_diffrn_orient_matrix_UB_31      0.0894747000
_diffrn_orient_matrix_UB_32      0.0018129000
_diffrn_orient_matrix_UB_33      -0.0051293000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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         0.983
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                3196
_reflns_number_total             3531
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.6126
_refine_diff_density_min         -0.4226
_refine_diff_density_rms         0.1139
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.025(12)
_refine_ls_d_res_high            0.8001
_refine_ls_d_res_low             7.1785
_refine_ls_goodness_of_fit_ref   1.0455
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3531
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.0455
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0324P)²+0.8771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0767
_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:
 C17(H17), C5(H5), C12(H12), C15(H15), C14(H14), C2(H2), C3(H3a), C16(H16)
2.c Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C10(H10a,H10b,H10c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Br1 Br 0.70689(6) 1.19735(3) 0.62576(2) 0.02554(12) Uani 1.000000 .
Mn1 Mn 0.37111(8) 0.65408(4) 0.60983(3) 0.01224(13) Uani 1.000000 .
O2 O 0.6932(4) 0.8362(2) 0.47847(14) 0.0227(6) Uani 1.000000 .
O1 O 0.3524(4) 0.78076(19) 0.66385(14) 0.0170(6) Uani 1.000000 .
N2 N 0.4659(4) 0.5159(3) 0.57792(18) 0.0142(7) Uani 1.000000 .
N1 N 0.5528(5) 0.7097(3) 0.54484(18) 0.0171(7) Uani 1.000000 .
N3 N 0.2298(5) 0.5842(2) 0.68349(18) 0.0152(8) Uani 1.000000 .
C7 C 0.6019(5) 0.8076(3) 0.5346(2) 0.0137(8) Uani 1.000000 .
C17 C 0.0786(5) 0.4483(3) 0.7523(2) 0.0185(10) Uani 1.000000 .
H17 H 0.0246(5) 0.4995(3) 0.7837(2) 0.0222(11) Uiso 1.000000 R
C6 C 0.5506(5) 0.8882(3) 0.5922(2) 0.0135(8) Uani 1.000000 .
C5 C 0.6268(6) 0.9873(3) 0.5845(2) 0.0170(9) Uani 1.000000 .
H5 H 0.7049(6) 0.9996(3) 0.5438(2) 0.0204(10) Uiso 1.000000 R
C12 C 0.4072(5) 0.4238(3) 0.5969(2) 0.0155(9) Uani 1.000000 .
H12 H 0.4580(5) 0.3650(3) 0.5723(2) 0.0187(11) Uiso 1.000000 R
C9 C 0.6229(6) 0.5240(3) 0.5291(2) 0.0164(9) Uani 1.000000 .
C8 C 0.6081(6) 0.6299(3) 0.4886(2) 0.0181(9) Uani 1.000000 .
H8a H 0.5245(6) 0.6251(3) 0.4461(2) 0.0217(11) Uiso 1.000000 R
H8b H 0.7194(6) 0.6500(3) 0.4664(2) 0.0217(11) Uiso 1.000000 R
C13 C 0.2752(5) 0.4020(3) 0.6503(2) 0.0167(9) Uani 1.000000 .
C15 C 0.1229(6) 0.2656(3) 0.7204(3) 0.0256(10) Uani 1.000000 .
H15 H 0.0993(6) 0.1935(3) 0.7295(3) 0.0308(12) Uiso 1.000000 R
C14 C 0.2355(5) 0.2948(3) 0.6641(2) 0.0216(10) Uani 1.000000 .
H14 H 0.2882(5) 0.2421(3) 0.6337(2) 0.0260(11) Uiso 1.000000 R
C18 C 0.1923(5) 0.4819(3) 0.6952(2) 0.0147(8) Uani 1.000000 .
C1 C 0.4359(5) 0.8706(3) 0.6521(2) 0.0143(9) Uani 1.000000 .
C2 C 0.3995(5) 0.9544(3) 0.7033(2) 0.0168(9) Uani 1.000000 .
H2 H 0.3207(5) 0.9435(3) 0.7439(2) 0.0202(11) Uiso 1.000000 R
C3 C 0.4755(5) 1.0512(3) 0.6955(2) 0.0156(9) Uani 1.000000 .
H3a H 0.4508(5) 1.1066(3) 0.7304(2) 0.0187(10) Uiso 1.000000 R
C11 C 0.6410(6) 0.4369(3) 0.4696(2) 0.0218(10) Uani 1.000000 .
H11a H 0.668(3) 0.3706(5) 0.4956(3) 0.0328(15) Uiso 1.000000 GR
H11b H 0.5341(13) 0.4294(14) 0.4412(11) 0.0328(15) Uiso 1.000000 GR
H11c H 0.733(2) 0.4547(11) 0.4337(10) 0.0328(15) Uiso 1.000000 GR
C10 C 0.7764(6) 0.5239(3) 0.5842(2) 0.0272(10) Uani 1.000000 .
H10a H 0.7674(19) 0.5835(13) 0.6197(11) 0.0408(16) Uiso 1.000000 GR
H10b H 0.778(2) 0.4582(10) 0.6137(12) 0.0408(16) Uiso 1.000000 GR
H10c H 0.8817(7) 0.530(2) 0.5544(3) 0.0408(16) Uiso 1.000000 GR
C4 C 0.5895(5) 1.0662(3) 0.6352(2) 0.0195(9) Uani 1.000000 .
C16 C 0.0427(6) 0.3440(4) 0.7645(2) 0.0243(10) Uani 1.000000 .
H16 H -0.0371(6) 0.3246(4) 0.8030(2) 0.0292(11) Uiso 1.000000 R
H3 H 0.184(5) 0.621(3) 0.7151(19) 0.002(10) Uiso 1.000000 .


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
Br1 C4 1.915(4) . ?
Mn1 O2 2.081(3) 2_466 ?
Mn1 O1 1.872(2) . ?
Mn1 N2 1.989(3) . ?
Mn1 N1 1.954(3) . ?
Mn1 N3 1.915(3) . ?
O2 C7 1.265(4) . ?
O1 C1 1.334(4) . ?
N2 C12 1.302(5) . ?
N2 C9 1.502(5) . ?
N1 C7 1.318(5) . ?
N1 C8 1.475(5) . ?
N3 C18 1.350(5) . ?
N3 H3 0.81(4) . ?
C7 C6 1.489(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.403(5) . ?
C17 C16 1.374(6) . ?
C6 C5 1.402(5) . ?
C6 C1 1.397(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.368(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.421(5) . ?
C9 C8 1.527(5) . ?
C9 C11 1.524(5) . ?
C9 C10 1.541(6) . ?
C8 H8a 0.9900 . ?
C8 H8b 0.9900 . ?
C13 C14 1.421(5) . ?
C13 C18 1.438(5) . ?
C15 H15 0.9500 . ?
C15 C14 1.371(6) . ?
C15 C16 1.407(6) . ?
C14 H14 0.9500 . ?
C1 C2 1.419(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(6) . ?
C3 H3a 0.9500 . ?
C3 C4 1.393(6) . ?
C11 H11a 0.9800 . ?
C11 H11b 0.9800 . ?
C11 H11c 0.9800 . ?
C10 H10a 0.9800 . ?
C10 H10b 0.9800 . ?
C10 H10c 0.9800 . ?
C16 H16 0.9500 . ?

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 105.43(11) . 2_466 ?
N2 Mn1 O2 95.66(12) . 2_466 ?
N2 Mn1 O1 158.61(13) . . ?
N1 Mn1 O2 92.50(13) . 2_466 ?
N1 Mn1 O1 92.05(13) . . ?
N1 Mn1 N2 83.39(14) . . ?
N3 Mn1 O2 97.49(14) . 2_466 ?
N3 Mn1 O1 91.09(13) . . ?
N3 Mn1 N2 89.61(14) . . ?
N3 Mn1 N1 168.33(15) . . ?
C7 O2 Mn1 165.4(3) . 2_566 ?
C1 O1 Mn1 128.5(2) . . ?
C12 N2 Mn1 126.3(3) . . ?
C9 N2 Mn1 113.9(2) . . ?
C9 N2 C12 119.7(3) . . ?
C7 N1 Mn1 129.4(3) . . ?
C8 N1 Mn1 110.5(2) . . ?
C8 N1 C7 118.4(3) . . ?
C18 N3 Mn1 132.5(3) . . ?
H3 N3 Mn1 116(3) . . ?
H3 N3 C18 111(3) . . ?
N1 C7 O2 122.9(3) . . ?
C6 C7 O2 118.3(3) . . ?
C6 C7 N1 118.8(3) . . ?
C18 C17 H17 118.9(2) . . ?
C16 C17 H17 118.9(3) . . ?
C16 C17 C18 122.3(4) . . ?
C5 C6 C7 116.1(4) . . ?
C1 C6 C7 124.4(3) . . ?
C1 C6 C5 119.5(4) . . ?
H5 C5 C6 119.8(2) . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 H5 119.8(2) . . ?
H12 C12 N2 116.5(2) . . ?
C13 C12 N2 126.9(4) . . ?
C13 C12 H12 116.5(2) . . ?
C8 C9 N2 105.0(3) . . ?
C11 C9 N2 114.3(3) . . ?
C11 C9 C8 109.6(3) . . ?
C10 C9 N2 107.0(3) . . ?
C10 C9 C8 110.4(3) . . ?
C10 C9 C11 110.4(4) . . ?
C9 C8 N1 108.9(3) . . ?
H8a C8 N1 109.9(2) . . ?
H8a C8 C9 109.9(2) . . ?
H8b C8 N1 109.9(2) . . ?
H8b C8 C9 109.9(2) . . ?
H8b C8 H8a 108.3 . . ?
C14 C13 C12 117.3(3) . . ?
C18 C13 C12 123.2(3) . . ?
C18 C13 C14 119.2(4) . . ?
C14 C15 H15 120.5(2) . . ?
C16 C15 H15 120.5(2) . . ?
C16 C15 C14 119.1(4) . . ?
C15 C14 C13 121.5(4) . . ?
H14 C14 C13 119.2(2) . . ?
H14 C14 C15 119.2(2) . . ?
C17 C18 N3 122.7(4) . . ?
C13 C18 N3 120.1(4) . . ?
C13 C18 C17 117.2(3) . . ?
C6 C1 O1 124.8(3) . . ?
C2 C1 O1 116.7(3) . . ?
C2 C1 C6 118.5(3) . . ?
H2 C2 C1 119.2(2) . . ?
C3 C2 C1 121.6(4) . . ?
C3 C2 H2 119.2(2) . . ?
H3a C3 C2 120.8(2) . . ?
C4 C3 C2 118.4(4) . . ?
C4 C3 H3a 120.8(2) . . ?
H11a C11 C9 109.5 . . ?
H11b C11 C9 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C9 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
H10a C10 C9 109.5 . . ?
H10b C10 C9 109.5 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 C9 109.5 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
C5 C4 Br1 118.8(3) . . ?
C3 C4 Br1 119.6(3) . . ?
C3 C4 C5 121.5(4) . . ?
C15 C16 C17 120.6(4) . . ?
H16 C16 C17 119.7(3) . . ?
H16 C16 C15 119.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C4 C5 C6 176.4(3) . . . . ?
Br1 C4 C3 C2 -176.7(3) . . . . ?
Mn1 O2 C7 N1 -35.3(11) 2_566 . . . ?
Mn1 O2 C7 C6 143.7(10) 2_566 . . . ?
Mn1 O1 C1 C6 3.8(4) . . . . ?
Mn1 O1 C1 C2 -178.5(3) . . . . ?
Mn1 N2 C12 C13 -7.1(4) . . . . ?
Mn1 N2 C9 C8 -27.2(2) . . . . ?
Mn1 N2 C9 C11 -147.3(3) . . . . ?
Mn1 N2 C9 C10 90.2(3) . . . . ?
Mn1 N1 C7 O2 -163.0(3) . . . . ?
Mn1 N1 C7 C6 18.0(4) . . . . ?
Mn1 N1 C8 C9 -43.3(3) . . . . ?
Mn1 N3 C18 C17 -177.8(4) . . . . ?
Mn1 N3 C18 C13 4.8(4) . . . . ?
O2 C7 N1 C8 0.5(5) . . . . ?
O2 C7 C6 C5 -8.1(4) . . . . ?
O2 C7 C6 C1 172.8(3) . . . . ?
O1 C1 C6 C7 -2.8(5) . . . . ?
O1 C1 C6 C5 178.1(4) . . . . ?
O1 C1 C2 C3 -178.6(3) . . . . ?
N2 C12 C13 C14 -177.9(4) . . . . ?
N2 C12 C13 C18 -3.5(5) . . . . ?
N2 C9 C8 N1 44.3(3) . . . . ?
N1 C7 C6 C5 171.0(4) . . . . ?
N1 C7 C6 C1 -8.1(4) . . . . ?
N1 C8 C9 C11 167.5(3) . . . . ?
N1 C8 C9 C10 -70.7(4) . . . . ?
N3 C18 C17 C16 -179.2(4) . . . . ?
N3 C18 C13 C12 5.0(4) . . . . ?
N3 C18 C13 C14 179.3(4) . . . . ?
C7 C6 C5 C4 -179.2(3) . . . . ?
C7 C6 C1 C2 179.5(4) . . . . ?
C17 C18 C13 C12 -172.5(4) . . . . ?
C17 C18 C13 C14 1.7(4) . . . . ?
C17 C16 C15 C14 -1.1(5) . . . . ?
C6 C5 C4 C3 -0.1(5) . . . . ?
C6 C1 C2 C3 -0.7(4) . . . . ?
C5 C4 C3 C2 -0.2(5) . . . . ?
C12 C13 C14 C15 173.1(4) . . . . ?
C13 C14 C15 C16 1.2(5) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?


_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 1.363
_oxdiff_exptl_absorpt_empirical_full_min 0.753
