# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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 
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data_jmc_121602_0m
_database_code_depnum_ccdc_archive 'CCDC 1822539'
_audit_update_record             
;
2018-02-06 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2018-02-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C20 H18 Mn N2)'
_chemical_formula_sum            'C60 H54 Mn3 N6'
_chemical_formula_weight         1023.91
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.5006(8)
_cell_length_b                   20.7775(10)
_cell_length_c                   30.9290(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.7317(14)
_cell_angle_gamma                90
_cell_volume                     11596.7(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9839
_cell_measurement_temperature    90
_cell_measurement_theta_max      28.49
_cell_measurement_theta_min      2.17
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1240 before and 0.0493 after correction. The Ratio of minimum to maximum transmission is 0.9047. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             4248
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.086
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            69869
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.252
_diffrn_reflns_theta_min         1.495
_diffrn_ambient_temperature      90
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus rotating anode'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8804
_reflns_number_total             10512
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     622
_refine_ls_number_reflns         10512
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+11.0687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0761
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C18(H18), C20(H20), C1(H1), C6(H6), C5(H5), C3(H3), C4(H4),
 C13(H13), C19(H19), C17(H17), C12(H12), C7(H7), C2(H2), C9(H9), C14(H14),
 C10(H10), C60(H60), C31(H31), C52(H52), C50(H50), C43(H43), C51(H51), C42(H42),
  C57(H57), C47(H47), C40(H40), C54(H54), C58(H58), C39(H39), C59(H59),
 C53(H53), C44(H44), C45(H45), C24(H24), C22(H22), C25(H25), C37(H37), C46(H46),
  C34(H34), C41(H41), C48(H48), C27(H27), C49(H49), C21(H21), C26(H26),
 C23(H23), C38(H38), C33(H33), C32(H32), C28(H28), C8(H8), C30(H30), C29(H29)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.11757(2) 0.84818(2) 0.65765(2) 0.01703(7) Uani 1 1 d . . . . .
N2 N 0.02560(8) 0.77507(7) 0.64806(5) 0.0200(3) Uani 1 1 d . . . . .
N1 N 0.16932(8) 0.75121(7) 0.65447(5) 0.0176(3) Uani 1 1 d . . . . .
C11 C 0.24229(10) 0.74145(9) 0.65909(6) 0.0222(4) Uani 1 1 d . . . . .
H11 H 0.273864 0.776790 0.664349 0.027 Uiso 1 1 calc R . . . .
C16 C 0.04375(10) 0.71327(8) 0.64321(6) 0.0186(4) Uani 1 1 d . . . . .
C15 C 0.12398(10) 0.69972(8) 0.64709(6) 0.0181(4) Uani 1 1 d . . . . .
C18 C -0.08310(11) 0.68145(10) 0.63093(7) 0.0307(5) Uani 1 1 d . . . . .
H18 H -0.119671 0.649949 0.625182 0.037 Uiso 1 1 calc R . . . .
C20 C -0.04596(10) 0.78987(10) 0.64458(7) 0.0262(4) Uani 1 1 d . . . . .
H20 H -0.058470 0.832555 0.648255 0.031 Uiso 1 1 calc R . . . .
C1 C 0.04002(11) 0.90755(11) 0.58858(6) 0.0309(5) Uani 1 1 d . . . . .
H1 H -0.011366 0.906624 0.584020 0.037 Uiso 1 1 calc R . . . .
C6 C 0.14551(15) 0.92413(11) 0.71622(7) 0.0417(6) Uani 1 1 d . . . . .
H6 H 0.149337 0.965035 0.704723 0.050 Uiso 1 1 calc R . . . .
C5 C 0.08572(12) 0.95781(11) 0.60733(7) 0.0332(5) Uani 1 1 d . . . . .
H5 H 0.070110 0.996468 0.617388 0.040 Uiso 1 1 calc R . . . .
C3 C 0.15906(11) 0.87906(11) 0.59022(7) 0.0326(5) Uani 1 1 d . . . . .
H3 H 0.200559 0.855971 0.586896 0.039 Uiso 1 1 calc R . . . .
C4 C 0.15909(12) 0.94058(11) 0.60854(7) 0.0335(5) Uani 1 1 d . . . . .
H4 H 0.200709 0.965640 0.619607 0.040 Uiso 1 1 calc R . . . .
C13 C 0.22569(12) 0.62879(10) 0.64899(7) 0.0319(5) Uani 1 1 d . . . . .
H13 H 0.244707 0.587687 0.647204 0.038 Uiso 1 1 calc R . . . .
C19 C -0.10174(11) 0.74480(10) 0.63581(7) 0.0311(5) Uani 1 1 d . . . . .
H19 H -0.150928 0.756826 0.633241 0.037 Uiso 1 1 calc R . . . .
C17 C -0.00973(11) 0.66515(9) 0.63465(6) 0.0259(4) Uani 1 1 d . . . . .
H17 H 0.003786 0.622591 0.631474 0.031 Uiso 1 1 calc R . . . .
C12 C 0.27249(11) 0.68148(10) 0.65639(7) 0.0274(4) Uani 1 1 d . . . . .
H12 H 0.323329 0.676470 0.659480 0.033 Uiso 1 1 calc R . . . .
C7 C 0.08214(13) 0.89657(12) 0.72462(7) 0.0394(6) Uani 1 1 d . . . . .
H7 H 0.035526 0.915628 0.719150 0.047 Uiso 1 1 calc R . . . .
C2 C 0.08488(12) 0.85833(10) 0.57769(7) 0.0323(5) Uani 1 1 d . . . . .
H2 H 0.068574 0.819130 0.564574 0.039 Uiso 1 1 calc R . . . .
C9 C 0.17354(14) 0.82507(11) 0.74460(7) 0.0416(6) Uani 1 1 d . . . . .
H9 H 0.199628 0.787953 0.755161 0.050 Uiso 1 1 calc R . . . .
C14 C 0.15073(11) 0.63786(9) 0.64431(7) 0.0271(4) Uani 1 1 d . . . . .
H14 H 0.118426 0.602996 0.639338 0.032 Uiso 1 1 calc R . . . .
C10 C 0.20232(12) 0.87988(13) 0.72799(7) 0.0442(7) Uani 1 1 d . . . . .
H10 H 0.251029 0.885511 0.725354 0.053 Uiso 1 1 calc R . . . .
Mn2 Mn 0.49237(2) 0.88208(2) 0.63702(2) 0.01922(7) Uani 1 1 d . . . . .
Mn3 Mn 0.77145(2) 0.95107(2) 0.50267(2) 0.01647(7) Uani 1 1 d . . . . .
N3 N 0.58257(8) 0.80941(7) 0.64721(5) 0.0215(3) Uani 1 1 d . . . . .
N5 N 0.79350(8) 0.93264(7) 0.57553(5) 0.0179(3) Uani 1 1 d . . . . .
C35 C 0.59732(10) 0.78201(9) 0.61052(7) 0.0228(4) Uani 1 1 d . . . . .
C55 C 0.84050(9) 0.97306(8) 0.60185(6) 0.0181(4) Uani 1 1 d . . . . .
N4 N 0.50642(8) 0.85454(7) 0.56946(5) 0.0191(3) Uani 1 1 d . . . . .
C56 C 0.87883(9) 1.02091(8) 0.57876(6) 0.0177(4) Uani 1 1 d . . . . .
N6 N 0.86838(8) 1.01352(7) 0.53466(5) 0.0177(3) Uani 1 1 d . . . . .
C36 C 0.55733(10) 0.80895(8) 0.56740(6) 0.0212(4) Uani 1 1 d . . . . .
C60 C 0.90477(10) 1.05307(9) 0.51244(6) 0.0218(4) Uani 1 1 d . . . . .
H60 H 0.898269 1.047820 0.481964 0.026 Uiso 1 1 calc R . . . .
C31 C 0.61685(10) 0.78688(9) 0.68685(7) 0.0265(4) Uani 1 1 d . . . . .
H31 H 0.607253 0.806337 0.712077 0.032 Uiso 1 1 calc R . . . .
C52 C 0.76874(10) 0.88128(9) 0.63974(6) 0.0252(4) Uani 1 1 d . . . . .
H52 H 0.743702 0.849466 0.651741 0.030 Uiso 1 1 calc R . . . .
C50 C 0.68343(11) 1.01969(10) 0.45661(7) 0.0309(5) Uani 1 1 d . . . . .
H50 H 0.693946 1.022298 0.428608 0.037 Uiso 1 1 calc R . . . .
C43 C 0.77242(11) 0.88679(9) 0.43446(7) 0.0280(4) Uani 1 1 d . . . . .
H43 H 0.745950 0.904564 0.408102 0.034 Uiso 1 1 calc R . . . .
C51 C 0.75884(10) 0.88783(9) 0.59465(6) 0.0214(4) Uani 1 1 d . . . . .
H51 H 0.726485 0.859794 0.576482 0.026 Uiso 1 1 calc R . . . .
C42 C 0.84639(11) 0.90070(9) 0.45516(7) 0.0279(5) Uani 1 1 d . . . . .
H42 H 0.877517 0.929207 0.444856 0.033 Uiso 1 1 calc R . . . .
C57 C 0.92306(10) 1.06945(9) 0.60111(6) 0.0252(4) Uani 1 1 d . . . . .
H57 H 0.927866 1.074754 0.631469 0.030 Uiso 1 1 calc R . . . .
C47 C 0.63753(10) 0.98585(9) 0.51478(7) 0.0263(4) Uani 1 1 d . . . . .
H47 H 0.612205 0.962336 0.532329 0.032 Uiso 1 1 calc R . . . .
C40 C 0.46849(10) 0.88048(9) 0.53157(6) 0.0231(4) Uani 1 1 d . . . . .
H40 H 0.433536 0.912104 0.533026 0.028 Uiso 1 1 calc R . . . .
C54 C 0.85332(11) 0.96905(9) 0.64760(6) 0.0240(4) Uani 1 1 d . . . . .
H54 H 0.886345 0.997174 0.665217 0.029 Uiso 1 1 calc R . . . .
C58 C 0.95997(11) 1.10994(10) 0.57787(7) 0.0284(5) Uani 1 1 d . . . . .
H58 H 0.990151 1.142663 0.592381 0.034 Uiso 1 1 calc R . . . .
C39 C 0.47899(11) 0.86229(10) 0.49031(7) 0.0266(4) Uani 1 1 d . . . . .
H39 H 0.451512 0.880994 0.464564 0.032 Uiso 1 1 calc R . . . .
C59 C 0.95144(10) 1.10118(9) 0.53298(7) 0.0255(4) Uani 1 1 d . . . . .
H59 H 0.976643 1.127177 0.516741 0.031 Uiso 1 1 calc R . . . .
C53 C 0.81661(11) 0.92282(10) 0.66699(7) 0.0273(4) Uani 1 1 d . . . . .
H53 H 0.824034 0.919839 0.697653 0.033 Uiso 1 1 calc R . . . .
C44 C 0.74563(11) 0.84127(9) 0.46067(7) 0.0277(5) Uani 1 1 d . . . . .
H44 H 0.698332 0.823495 0.454574 0.033 Uiso 1 1 calc R . . . .
C45 C 0.80217(11) 0.82733(9) 0.49740(7) 0.0271(4) Uani 1 1 d . . . . .
H45 H 0.799053 0.798841 0.520104 0.033 Uiso 1 1 calc R . . . .
C24 C 0.60612(11) 0.97487(9) 0.63162(7) 0.0262(4) Uani 1 1 d . . . . .
H24 H 0.646171 0.970971 0.618167 0.031 Uiso 1 1 calc R . . . .
C22 C 0.53566(12) 0.97265(10) 0.68299(7) 0.0324(5) Uani 1 1 d . . . . .
H22 H 0.520696 0.966932 0.709536 0.039 Uiso 1 1 calc R . . . .
C25 C 0.53485(11) 0.99616(9) 0.61101(7) 0.0254(4) Uani 1 1 d . . . . .
H25 H 0.519529 1.008726 0.581549 0.030 Uiso 1 1 calc R . . . .
C37 C 0.57107(11) 0.78895(10) 0.52717(7) 0.0307(5) Uani 1 1 d . . . . .
H37 H 0.606793 0.757759 0.526337 0.037 Uiso 1 1 calc R . . . .
C46 C 0.63890(10) 0.97246(9) 0.47087(7) 0.0265(4) Uani 1 1 d . . . . .
H46 H 0.614846 0.938548 0.453972 0.032 Uiso 1 1 calc R . . . .
C34 C 0.64646(11) 0.73084(9) 0.61329(7) 0.0317(5) Uani 1 1 d . . . . .
H34 H 0.656189 0.712503 0.587731 0.038 Uiso 1 1 calc R . . . .
C41 C 0.86488(11) 0.86396(9) 0.49411(7) 0.0294(5) Uani 1 1 d . . . . .
H41 H 0.910419 0.863796 0.514192 0.035 Uiso 1 1 calc R . . . .
C48 C 0.68056(11) 1.04052(10) 0.52805(7) 0.0295(5) Uani 1 1 d . . . . .
H48 H 0.689029 1.059596 0.555913 0.035 Uiso 1 1 calc R . . . .
C27 C 0.36443(11) 0.88324(11) 0.65695(7) 0.0333(5) Uani 1 1 d . . . . .
H27 H 0.340066 0.922670 0.654481 0.040 Uiso 1 1 calc R . . . .
C49 C 0.70888(11) 1.06171(10) 0.49183(8) 0.0317(5) Uani 1 1 d . . . . .
H49 H 0.739145 1.097353 0.491464 0.038 Uiso 1 1 calc R . . . .
C21 C 0.49072(11) 0.99522(9) 0.64253(7) 0.0288(5) Uani 1 1 d . . . . .
H21 H 0.441155 1.007170 0.637801 0.035 Uiso 1 1 calc R . . . .
C26 C 0.36716(11) 0.84150(10) 0.62205(7) 0.0301(5) Uani 1 1 d . . . . .
H26 H 0.345214 0.848311 0.592339 0.036 Uiso 1 1 calc R . . . .
C23 C 0.60659(12) 0.96056(9) 0.67574(7) 0.0305(5) Uani 1 1 d . . . . .
H23 H 0.647034 0.945563 0.696745 0.037 Uiso 1 1 calc R . . . .
C38 C 0.53119(11) 0.81580(10) 0.48844(7) 0.0321(5) Uani 1 1 d . . . . .
H38 H 0.539522 0.802581 0.461225 0.039 Uiso 1 1 calc R . . . .
C33 C 0.68054(13) 0.70768(10) 0.65445(8) 0.0388(5) Uani 1 1 d . . . . .
H33 H 0.713235 0.673187 0.656952 0.047 Uiso 1 1 calc R . . . .
C32 C 0.66586(12) 0.73603(10) 0.69200(8) 0.0339(5) Uani 1 1 d . . . . .
H32 H 0.688496 0.721154 0.720081 0.041 Uiso 1 1 calc R . . . .
C28 C 0.40420(13) 0.85605(13) 0.69602(8) 0.0438(6) Uani 1 1 d . . . . .
H28 H 0.411146 0.874109 0.724143 0.053 Uiso 1 1 calc R . . . .
C8 C 0.09913(13) 0.83645(11) 0.74238(7) 0.0373(5) Uani 1 1 d . . . . .
H8 H 0.066272 0.808226 0.751365 0.045 Uiso 1 1 calc R . . . .
C30 C 0.40870(12) 0.78760(12) 0.63959(9) 0.0460(6) Uani 1 1 d . . . . .
H30 H 0.419243 0.751968 0.623854 0.055 Uiso 1 1 calc R . . . .
C29 C 0.43161(12) 0.79760(14) 0.68583(9) 0.0520(7) Uani 1 1 d . . . . .
H29 H 0.460319 0.769502 0.705966 0.062 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 N2 2.2512(15) . ?
Mn1 N1 2.2420(15) . ?
Mn1 C1 2.6064(19) . ?
Mn1 C6 2.372(2) . ?
Mn1 C3 2.4610(19) . ?
Mn1 C7 2.516(2) . ?
Mn1 C2 2.422(2) . ?
Mn1 C10 2.474(2) . ?
N2 C16 1.344(2) . ?
N2 C20 1.340(2) . ?
N1 C11 1.341(2) . ?
N1 C15 1.348(2) . ?
C11 C12 1.376(3) . ?
C16 C15 1.490(2) . ?
C16 C17 1.390(3) . ?
C15 C14 1.387(3) . ?
C18 C19 1.377(3) . ?
C18 C17 1.379(3) . ?
C20 C19 1.376(3) . ?
C1 C5 1.388(3) . ?
C1 C2 1.404(3) . ?
C6 C7 1.380(3) . ?
C6 C10 1.383(3) . ?
C5 C4 1.396(3) . ?
C3 C4 1.398(3) . ?
C3 C2 1.409(3) . ?
C13 C12 1.383(3) . ?
C13 C14 1.375(3) . ?
C7 C8 1.373(3) . ?
C9 C10 1.402(3) . ?
C9 C8 1.384(3) . ?
Mn2 N3 2.2207(15) . ?
Mn2 N4 2.2361(15) . ?
Mn2 C22 2.388(2) . ?
Mn2 C27 2.574(2) . ?
Mn2 C21 2.3577(19) . ?
Mn2 C26 2.4122(19) . ?
Mn2 C30 2.512(2) . ?
Mn3 N5 2.2329(15) . ?
Mn3 N6 2.2576(15) . ?
Mn3 C50 2.386(2) . ?
Mn3 C43 2.500(2) . ?
Mn3 C42 2.4646(18) . ?
Mn3 C44 2.6166(19) . ?
Mn3 C46 2.4731(19) . ?
Mn3 C41 2.5564(19) . ?
Mn3 C49 2.5625(19) . ?
N3 C35 1.350(2) . ?
N3 C31 1.335(2) . ?
N5 C55 1.346(2) . ?
N5 C51 1.340(2) . ?
C35 C36 1.485(3) . ?
C35 C34 1.389(3) . ?
C55 C56 1.491(2) . ?
C55 C54 1.385(3) . ?
N4 C36 1.347(2) . ?
N4 C40 1.339(2) . ?
C56 N6 1.343(2) . ?
C56 C57 1.384(3) . ?
N6 C60 1.343(2) . ?
C36 C37 1.387(3) . ?
C60 C59 1.381(3) . ?
C31 C32 1.379(3) . ?
C52 C51 1.373(3) . ?
C52 C53 1.382(3) . ?
C50 C46 1.413(3) . ?
C50 C49 1.395(3) . ?
C43 C42 1.407(3) . ?
C43 C44 1.405(3) . ?
C42 C41 1.403(3) . ?
C57 C58 1.381(3) . ?
C47 C46 1.392(3) . ?
C47 C48 1.396(3) . ?
C40 C39 1.385(3) . ?
C54 C53 1.387(3) . ?
C58 C59 1.374(3) . ?
C39 C38 1.376(3) . ?
C44 C45 1.395(3) . ?
C45 C41 1.410(3) . ?
C24 C25 1.404(3) . ?
C24 C23 1.394(3) . ?
C22 C21 1.421(3) . ?
C22 C23 1.402(3) . ?
C25 C21 1.403(3) . ?
C37 C38 1.379(3) . ?
C34 C33 1.377(3) . ?
C48 C49 1.408(3) . ?
C27 C26 1.394(3) . ?
C27 C28 1.389(3) . ?
C26 C30 1.398(3) . ?
C33 C32 1.382(3) . ?
C28 C29 1.379(4) . ?
C30 C29 1.415(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Mn1 C1 87.01(6) . . ?
N2 Mn1 C6 125.50(7) . . ?
N2 Mn1 C3 115.61(7) . . ?
N2 Mn1 C7 92.96(7) . . ?
N2 Mn1 C2 85.00(6) . . ?
N2 Mn1 C10 127.56(7) . . ?
N1 Mn1 N2 72.88(5) . . ?
N1 Mn1 C1 123.54(6) . . ?
N1 Mn1 C6 127.45(7) . . ?
N1 Mn1 C3 88.92(6) . . ?
N1 Mn1 C7 125.91(7) . . ?
N1 Mn1 C2 92.66(6) . . ?
N1 Mn1 C10 94.81(8) . . ?
C6 Mn1 C1 107.40(8) . . ?
C6 Mn1 C3 114.68(8) . . ?
C6 Mn1 C7 32.63(8) . . ?
C6 Mn1 C2 133.25(8) . . ?
C6 Mn1 C10 33.08(8) . . ?
C3 Mn1 C1 53.14(6) . . ?
C3 Mn1 C7 141.26(8) . . ?
C3 Mn1 C10 114.85(8) . . ?
C7 Mn1 C1 106.83(7) . . ?
C2 Mn1 C1 32.16(7) . . ?
C2 Mn1 C3 33.52(7) . . ?
C2 Mn1 C7 138.95(7) . . ?
C2 Mn1 C10 147.33(8) . . ?
C10 Mn1 C1 136.25(9) . . ?
C10 Mn1 C7 53.07(7) . . ?
C16 N2 Mn1 117.33(12) . . ?
C20 N2 Mn1 124.08(13) . . ?
C20 N2 C16 118.49(16) . . ?
C11 N1 Mn1 124.11(12) . . ?
C11 N1 C15 118.18(16) . . ?
C15 N1 Mn1 117.71(11) . . ?
N1 C11 C12 122.91(18) . . ?
N2 C16 C15 116.15(15) . . ?
N2 C16 C17 121.57(17) . . ?
C17 C16 C15 122.28(17) . . ?
N1 C15 C16 115.82(15) . . ?
N1 C15 C14 121.95(17) . . ?
C14 C15 C16 122.22(16) . . ?
C19 C18 C17 119.43(18) . . ?
N2 C20 C19 123.00(19) . . ?
C5 C1 Mn1 80.74(12) . . ?
C5 C1 C2 108.09(19) . . ?
C2 C1 Mn1 66.68(11) . . ?
C7 C6 Mn1 79.43(13) . . ?
C7 C6 C10 107.6(2) . . ?
C10 C6 Mn1 77.52(13) . . ?
C1 C5 C4 108.51(19) . . ?
C4 C3 Mn1 82.37(12) . . ?
C4 C3 C2 107.72(18) . . ?
C2 C3 Mn1 71.73(11) . . ?
C5 C4 C3 108.1(2) . . ?
C14 C13 C12 119.28(18) . . ?
C20 C19 C18 118.49(19) . . ?
C18 C17 C16 119.03(18) . . ?
C11 C12 C13 118.63(18) . . ?
C6 C7 Mn1 67.94(12) . . ?
C8 C7 Mn1 83.54(13) . . ?
C8 C7 C6 108.9(2) . . ?
C1 C2 Mn1 81.16(12) . . ?
C1 C2 C3 107.6(2) . . ?
C3 C2 Mn1 74.75(12) . . ?
C8 C9 C10 107.3(2) . . ?
C13 C14 C15 119.06(18) . . ?
C6 C10 Mn1 69.39(12) . . ?
C6 C10 C9 108.0(2) . . ?
C9 C10 Mn1 83.55(13) . . ?
N3 Mn2 N4 73.75(6) . . ?
N3 Mn2 C22 107.96(7) . . ?
N3 Mn2 C27 132.40(7) . . ?
N3 Mn2 C21 133.54(6) . . ?
N3 Mn2 C26 116.71(7) . . ?
N3 Mn2 C30 85.03(7) . . ?
N4 Mn2 C22 131.70(7) . . ?
N4 Mn2 C27 121.91(6) . . ?
N4 Mn2 C21 109.19(6) . . ?
N4 Mn2 C26 92.05(6) . . ?
N4 Mn2 C30 91.66(7) . . ?
C22 Mn2 C27 93.17(7) . . ?
C22 Mn2 C26 124.85(7) . . ?
C22 Mn2 C30 136.47(8) . . ?
C21 Mn2 C22 34.83(7) . . ?
C21 Mn2 C27 86.91(7) . . ?
C21 Mn2 C26 109.58(7) . . ?
C21 Mn2 C30 139.37(7) . . ?
C26 Mn2 C27 32.26(7) . . ?
C26 Mn2 C30 32.92(7) . . ?
C30 Mn2 C27 52.71(7) . . ?
N5 Mn3 N6 72.87(5) . . ?
N5 Mn3 C50 130.85(6) . . ?
N5 Mn3 C43 136.57(6) . . ?
N5 Mn3 C42 121.82(6) . . ?
N5 Mn3 C44 108.93(6) . . ?
N5 Mn3 C46 112.14(6) . . ?
N5 Mn3 C41 90.33(6) . . ?
N5 Mn3 C49 105.23(6) . . ?
N6 Mn3 C50 106.85(7) . . ?
N6 Mn3 C43 121.61(6) . . ?
N6 Mn3 C42 90.48(6) . . ?
N6 Mn3 C44 139.39(6) . . ?
N6 Mn3 C46 133.89(6) . . ?
N6 Mn3 C41 87.85(6) . . ?
N6 Mn3 C49 80.44(6) . . ?
C50 Mn3 C43 86.91(7) . . ?
C50 Mn3 C42 107.29(7) . . ?
C50 Mn3 C44 101.46(7) . . ?
C50 Mn3 C46 33.75(7) . . ?
C50 Mn3 C41 138.53(7) . . ?
C50 Mn3 C49 32.49(7) . . ?
C43 Mn3 C44 31.77(6) . . ?
C43 Mn3 C41 53.39(7) . . ?
C43 Mn3 C49 117.12(7) . . ?
C42 Mn3 C43 32.92(7) . . ?
C42 Mn3 C44 53.06(6) . . ?
C42 Mn3 C46 118.55(7) . . ?
C42 Mn3 C41 32.40(7) . . ?
C42 Mn3 C49 126.88(7) . . ?
C46 Mn3 C43 87.20(7) . . ?
C46 Mn3 C44 84.41(6) . . ?
C46 Mn3 C41 136.04(7) . . ?
C46 Mn3 C49 53.63(7) . . ?
C41 Mn3 C44 52.04(6) . . ?
C41 Mn3 C49 156.62(7) . . ?
C49 Mn3 C44 133.58(7) . . ?
C35 N3 Mn2 116.88(12) . . ?
C31 N3 Mn2 123.98(13) . . ?
C31 N3 C35 118.75(16) . . ?
C55 N5 Mn3 116.95(11) . . ?
C51 N5 Mn3 124.45(12) . . ?
C51 N5 C55 118.36(16) . . ?
N3 C35 C36 116.30(16) . . ?
N3 C35 C34 121.45(19) . . ?
C34 C35 C36 122.25(17) . . ?
N5 C55 C56 115.99(15) . . ?
N5 C55 C54 121.51(17) . . ?
C54 C55 C56 122.48(17) . . ?
C36 N4 Mn2 116.79(12) . . ?
C40 N4 Mn2 124.63(12) . . ?
C40 N4 C36 118.58(16) . . ?
N6 C56 C55 115.65(15) . . ?
N6 C56 C57 121.82(17) . . ?
C57 C56 C55 122.53(16) . . ?
C56 N6 Mn3 115.67(11) . . ?
C60 N6 Mn3 124.52(12) . . ?
C60 N6 C56 118.25(15) . . ?
N4 C36 C35 115.95(16) . . ?
N4 C36 C37 121.42(18) . . ?
C37 C36 C35 122.63(17) . . ?
N6 C60 C59 122.71(17) . . ?
N3 C31 C32 122.84(19) . . ?
C51 C52 C53 118.79(18) . . ?
C46 C50 Mn3 76.51(11) . . ?
C49 C50 Mn3 80.74(12) . . ?
C49 C50 C46 108.10(18) . . ?
C42 C43 Mn3 72.14(11) . . ?
C44 C43 Mn3 78.68(12) . . ?
C44 C43 C42 107.89(19) . . ?
N5 C51 C52 123.20(18) . . ?
C43 C42 Mn3 74.94(11) . . ?
C41 C42 Mn3 77.40(11) . . ?
C41 C42 C43 107.90(18) . . ?
C58 C57 C56 119.32(18) . . ?
C46 C47 C48 108.52(18) . . ?
N4 C40 C39 122.93(17) . . ?
C55 C54 C53 119.58(18) . . ?
C59 C58 C57 119.02(18) . . ?
C38 C39 C40 118.19(19) . . ?
C58 C59 C60 118.80(18) . . ?
C52 C53 C54 118.56(18) . . ?
C43 C44 Mn3 69.55(11) . . ?
C45 C44 Mn3 75.79(11) . . ?
C45 C44 C43 108.24(18) . . ?
C44 C45 C41 108.10(18) . . ?
C23 C24 C25 108.32(18) . . ?
C21 C22 Mn2 71.41(11) . . ?
C23 C22 Mn2 88.07(12) . . ?
C23 C22 C21 107.74(19) . . ?
C21 C25 C24 108.19(19) . . ?
C38 C37 C36 119.29(18) . . ?
C50 C46 Mn3 69.74(11) . . ?
C47 C46 Mn3 82.96(12) . . ?
C47 C46 C50 107.63(18) . . ?
C33 C34 C35 119.0(2) . . ?
C42 C41 Mn3 70.20(11) . . ?
C42 C41 C45 107.86(18) . . ?
C45 C41 Mn3 77.80(11) . . ?
C47 C48 C49 107.99(19) . . ?
C26 C27 Mn2 67.46(11) . . ?
C28 C27 Mn2 82.28(13) . . ?
C28 C27 C26 108.5(2) . . ?
C50 C49 Mn3 66.77(11) . . ?
C50 C49 C48 107.76(18) . . ?
C48 C49 Mn3 81.49(12) . . ?
C22 C21 Mn2 73.75(11) . . ?
C25 C21 Mn2 86.84(11) . . ?
C25 C21 C22 107.44(18) . . ?
C27 C26 Mn2 80.28(12) . . ?
C27 C26 C30 108.0(2) . . ?
C30 C26 Mn2 77.47(12) . . ?
C24 C23 C22 108.31(19) . . ?
C39 C38 C37 119.59(19) . . ?
C34 C33 C32 119.57(19) . . ?
C31 C32 C33 118.4(2) . . ?
C29 C28 C27 108.1(2) . . ?
C7 C8 C9 108.2(2) . . ?
C26 C30 Mn2 69.61(12) . . ?
C26 C30 C29 106.9(2) . . ?
C29 C30 Mn2 82.40(15) . . ?
C28 C29 C30 108.5(2) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.892 -0.093 0.250 470.5 118.9 ?
2 -0.395 0.093 0.750 470.5 118.8 ?
3 -0.151 0.407 0.250 470.5 118.9 ?
4 -0.334 0.593 0.750 470.5 118.8 ?
5 0.250 0.250 0.000 158.1 39.9 ?
6 0.250 0.750 0.500 158.1 39.9 ?
7 0.750 0.250 0.500 158.1 39.9 ?
8 0.750 0.750 0.000 158.1 39.9 ?

_olex2_submission_special_instructions ACTA
####################################################################### 
# 
# 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_lacy2_a
_database_code_depnum_ccdc_archive 'CCDC 1822546'
_audit_update_record             
;
2018-02-06 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 Mn N2'
_chemical_formula_weight         369.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.7577(14)
_cell_length_b                   11.0932(14)
_cell_length_c                   15.441(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.970(5)
_cell_angle_gamma                90
_cell_volume                     1892.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    6554
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      30.25

_exptl_crystal_description       Plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             772
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.703
_shelx_estimated_absorpt_T_min   0.781
_shelx_estimated_absorpt_T_max   0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6747
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17051
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.311
_diffrn_reflns_theta_max         26.011
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3716
_reflns_number_gt                3089
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0499P)²+0.5685P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3716
_refine_ls_number_parameters     228
_refine_ls_number_restraints     80
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn Mn 0.77703(2) 0.35610(2) 0.73561(2) 0.04329(12) Uani 1 1 d . . . . .
N1 N 0.75941(13) 0.45474(14) 0.60634(10) 0.0455(4) Uani 1 1 d . . . . .
N2 N 0.62452(12) 0.27221(13) 0.62469(10) 0.0426(3) Uani 1 1 d . . . . .
C1 C 0.83207(18) 0.5437(2) 0.59910(15) 0.0582(5) Uani 1 1 d . . . . .
H1 H 0.8925 0.5707 0.6530 0.070 Uiso 1 1 calc R U . . .
C2 C 0.8231(2) 0.5974(2) 0.51729(15) 0.0600(5) Uani 1 1 d . . . . .
H2 H 0.8763 0.6600 0.5159 0.072 Uiso 1 1 calc R U . . .
C3 C 0.73604(18) 0.55964(18) 0.43720(14) 0.0518(5) Uani 1 1 d . . . . .
C4 C 0.66125(16) 0.46704(17) 0.44481(13) 0.0465(4) Uani 1 1 d . . . . .
H4 H 0.6013 0.4375 0.3916 0.056 Uiso 1 1 calc R U . . .
C5 C 0.67340(14) 0.41765(15) 0.52924(12) 0.0387(4) Uani 1 1 d . . . . .
C6 C 0.59378(14) 0.31995(15) 0.54079(12) 0.0378(4) Uani 1 1 d . . . . .
C7 C 0.49326(15) 0.28056(16) 0.46970(12) 0.0427(4) Uani 1 1 d . . . . .
H7 H 0.4724 0.3173 0.4115 0.051 Uiso 1 1 calc R U . . .
C8 C 0.42314(16) 0.18768(18) 0.48343(13) 0.0456(4) Uani 1 1 d . . . . .
C9 C 0.45640(18) 0.13880(17) 0.57046(14) 0.0504(5) Uani 1 1 d . . . . .
H9 H 0.4111 0.0759 0.5834 0.060 Uiso 1 1 calc R U . . .
C10 C 0.55608(18) 0.18296(19) 0.63779(14) 0.0525(5) Uani 1 1 d . . . . .
H10 H 0.5778 0.1485 0.6968 0.063 Uiso 1 1 calc R U . . .
C11 C 0.7222(3) 0.6159(2) 0.34625(17) 0.0732(7) Uani 1 1 d . . . . .
H11A H 0.6991 0.6998 0.3468 0.110 Uiso 1 1 calc R U . . .
H11B H 0.6601 0.5734 0.2978 0.110 Uiso 1 1 calc R U . . .
H11C H 0.7984 0.6111 0.3351 0.110 Uiso 1 1 calc R U . . .
C12 C 0.3159(2) 0.1412(2) 0.40721(16) 0.0630(6) Uani 1 1 d . . . . .
H12A H 0.3397 0.0721 0.3788 0.095 Uiso 1 1 calc R U . . .
H12B H 0.2847 0.2039 0.3615 0.095 Uiso 1 1 calc R U . . .
H12C H 0.2537 0.1172 0.4318 0.095 Uiso 1 1 calc R U . . .
C13 C 0.7527(3) 0.5466(2) 0.8184(2) 0.0811(8) Uani 1 1 d . U . . .
H13 H 0.7831 0.6132 0.7956 0.097 Uiso 1 1 calc R U . . .
C14 C 0.6454(2) 0.4852(2) 0.77400(17) 0.0737(7) Uani 1 1 d . U . . .
H14 H 0.5889 0.5034 0.7157 0.088 Uiso 1 1 calc R U . . .
C15 C 0.6370(2) 0.3923(2) 0.83136(18) 0.0682(6) Uani 1 1 d . U . . .
H15 H 0.5742 0.3354 0.8183 0.082 Uiso 1 1 calc R U . . .
C16 C 0.7345(2) 0.3974(2) 0.90935(18) 0.0735(7) Uani 1 1 d . U . . .
H16 H 0.7504 0.3450 0.9600 0.088 Uiso 1 1 calc R U . . .
C17 C 0.8057(2) 0.4908(3) 0.9024(2) 0.0831(8) Uani 1 1 d . U . . .
H17 H 0.8791 0.5137 0.9475 0.100 Uiso 1 1 calc R U . . .
C18 C 0.9948(2) 0.2973(3) 0.7437(3) 0.0854(8) Uani 1 1 d . U . . .
H18 H 1.0430 0.3562 0.7295 0.102 Uiso 1 1 calc R U . . .
C19 C 0.9680(2) 0.2919(2) 0.82237(19) 0.0752(7) Uani 1 1 d . U . . .
H19 H 0.9944 0.3463 0.8719 0.090 Uiso 1 1 calc R U . . .
C20 C 0.8951(2) 0.1924(3) 0.8171(2) 0.0759(7) Uani 1 1 d . U . . .
H20 H 0.8626 0.1667 0.8618 0.091 Uiso 1 1 calc R U . . .
C21 C 0.8795(2) 0.1385(2) 0.7338(3) 0.0917(10) Uani 1 1 d . U . . .
H21 H 0.8343 0.0682 0.7113 0.110 Uiso 1 1 calc R U . . .
C22 C 0.9405(3) 0.2037(4) 0.6892(2) 0.0994(10) Uani 1 1 d . U . . .
H22 H 0.9442 0.1867 0.6306 0.119 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn N2 2.2174(14) . ?
Mn N1 2.2231(16) . ?
Mn C19 2.300(2) . ?
Mn C14 2.329(2) . ?
Mn C20 2.370(2) . ?
Mn C13 2.536(2) . ?
Mn C15 2.592(2) . ?
Mn C18 2.603(3) . ?
N1 C1 1.334(2) . ?
N1 C5 1.337(2) . ?
N2 C6 1.330(2) . ?
N2 C10 1.334(2) . ?
C1 C2 1.368(3) . ?
C1 H1 0.9400 . ?
C2 C3 1.374(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.383(3) . ?
C3 C11 1.494(3) . ?
C4 C5 1.376(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.482(2) . ?
C6 C7 1.381(2) . ?
C7 C8 1.381(3) . ?
C7 H7 0.9400 . ?
C8 C9 1.376(3) . ?
C8 C12 1.492(3) . ?
C9 C10 1.365(3) . ?
C9 H9 0.9400 . ?
C10 H10 0.9400 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 C17 1.379(4) . ?
C13 C14 1.391(4) . ?
C13 H13 0.9400 . ?
C14 C15 1.384(4) . ?
C14 H14 0.9400 . ?
C15 C16 1.350(4) . ?
C15 H15 0.9400 . ?
C16 C17 1.360(4) . ?
C16 H16 0.9400 . ?
C17 H17 0.9400 . ?
C18 C22 1.351(5) . ?
C18 C19 1.356(4) . ?
C18 H18 0.9400 . ?
C19 C20 1.382(4) . ?
C19 H19 0.9400 . ?
C20 C21 1.374(4) . ?
C20 H20 0.9400 . ?
C21 C22 1.359(5) . ?
C21 H21 0.9400 . ?
C22 H22 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
N2 Mn N1 73.16(5) . . ?
N2 Mn C19 133.71(8) . . ?
N1 Mn C19 116.65(9) . . ?
N2 Mn C14 91.27(8) . . ?
N1 Mn C14 93.42(8) . . ?
C19 Mn C14 130.07(9) . . ?
N2 Mn C20 105.14(8) . . ?
N1 Mn C20 135.42(8) . . ?
C19 Mn C20 34.40(9) . . ?
C14 Mn C20 130.96(9) . . ?
N2 Mn C13 122.56(9) . . ?
N1 Mn C13 92.88(8) . . ?
C19 Mn C13 102.74(10) . . ?
C14 Mn C13 32.87(9) . . ?
C20 Mn C13 121.16(11) . . ?
N2 Mn C15 90.12(7) . . ?
N1 Mn C15 123.58(7) . . ?
C19 Mn C15 113.56(10) . . ?
C14 Mn C15 32.10(8) . . ?
C20 Mn C15 100.76(9) . . ?
C13 Mn C15 51.71(8) . . ?
N2 Mn C18 117.03(9) . . ?
N1 Mn C18 87.43(8) . . ?
C19 Mn C18 31.34(10) . . ?
C14 Mn C18 150.46(11) . . ?
C20 Mn C18 52.72(9) . . ?
C13 Mn C18 117.59(11) . . ?
C15 Mn C18 144.80(10) . . ?
C1 N1 C5 117.65(16) . . ?
C1 N1 Mn 124.97(13) . . ?
C5 N1 Mn 117.28(11) . . ?
C6 N2 C10 117.76(15) . . ?
C6 N2 Mn 117.66(11) . . ?
C10 N2 Mn 124.39(12) . . ?
N1 C1 C2 123.36(19) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C3 119.81(19) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 116.73(18) . . ?
C2 C3 C11 121.81(19) . . ?
C4 C3 C11 121.46(19) . . ?
C5 C4 C3 120.86(17) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
N1 C5 C4 121.57(16) . . ?
N1 C5 C6 115.76(15) . . ?
C4 C5 C6 122.67(15) . . ?
N2 C6 C7 121.49(16) . . ?
N2 C6 C5 115.83(15) . . ?
C7 C6 C5 122.68(16) . . ?
C8 C7 C6 120.53(17) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C7 117.30(16) . . ?
C9 C8 C12 121.05(18) . . ?
C7 C8 C12 121.66(18) . . ?
C10 C9 C8 119.10(18) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
N2 C10 C9 123.81(18) . . ?
N2 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C17 C13 C14 106.6(2) . . ?
C17 C13 Mn 90.43(16) . . ?
C14 C13 Mn 65.36(13) . . ?
C17 C13 H13 126.7 . . ?
C14 C13 H13 126.7 . . ?
Mn C13 H13 110.0 . . ?
C15 C14 C13 107.5(2) . . ?
C15 C14 Mn 84.48(15) . . ?
C13 C14 Mn 81.77(14) . . ?
C15 C14 H14 126.3 . . ?
C13 C14 H14 126.3 . . ?
Mn C14 H14 101.7 . . ?
C16 C15 C14 108.4(2) . . ?
C16 C15 Mn 90.24(16) . . ?
C14 C15 Mn 63.43(12) . . ?
C16 C15 H15 125.8 . . ?
C14 C15 H15 125.8 . . ?
Mn C15 H15 112.3 . . ?
C15 C16 C17 108.6(3) . . ?
C15 C16 H16 125.7 . . ?
C17 C16 H16 125.7 . . ?
C16 C17 C13 108.9(2) . . ?
C16 C17 H17 125.6 . . ?
C13 C17 H17 125.6 . . ?
C22 C18 C19 108.6(3) . . ?
C22 C18 Mn 85.12(16) . . ?
C19 C18 Mn 61.89(13) . . ?
C22 C18 H18 125.7 . . ?
C19 C18 H18 125.7 . . ?
Mn C18 H18 118.5 . . ?
C18 C19 C20 108.2(2) . . ?
C18 C19 Mn 86.77(16) . . ?
C20 C19 Mn 75.57(12) . . ?
C18 C19 H19 125.9 . . ?
C20 C19 H19 125.9 . . ?
Mn C19 H19 105.1 . . ?
C21 C20 C19 106.5(3) . . ?
C21 C20 Mn 88.25(16) . . ?
C19 C20 Mn 70.03(13) . . ?
C21 C20 H20 126.8 . . ?
C19 C20 H20 126.8 . . ?
Mn C20 H20 108.1 . . ?
C22 C21 C20 108.5(3) . . ?
C22 C21 H21 125.7 . . ?
C20 C21 H21 125.7 . . ?
C18 C22 C21 108.2(3) . . ?
C18 C22 H22 125.9 . . ?
C21 C22 H22 125.9 . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_dcl_001_skd_056
_database_code_depnum_ccdc_archive 'CCDC 1822540'
_audit_update_record             
;
2018-02-06 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2018-02-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 Mn N2'
_chemical_formula_sum            'C22 H18 Mn N2'
_chemical_formula_weight         365.32
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   11.0154(6)
_cell_length_b                   26.5037(15)
_cell_length_c                   11.5756(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3379.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7404
_cell_measurement_temperature    90
_cell_measurement_theta_max      24.12
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) was 0.1739 before and 0.0711 after correction. The Ratio of minimum to maximum transmission is 0.8444. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            45577
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.443
_diffrn_reflns_theta_min         1.537
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                5812
_reflns_number_total             6871
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.772
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.15(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         6871
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0594P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1045
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.85(2)
 0.15(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C18(H18), C20(H20), C16(H16), C1(H1), C6(H6), C4(H4),
 C13(H13), C15(H15), C12(H12), C3(H3), C7(H7), C10(H10), C5(H5), C31(H31),
 C41(H41), C27(H27), C33(H33), C42(H42), C24(H24), C34(H34), C35(H35), C30(H30),
  C32(H32), C40(H40), C38(H38), C29(H29), C2(H2), C19(H19), C11(H11), C26(H26),
 C25(H25), C37(H37), C23(H23), C28(H28)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.61135(6) 0.89773(2) 0.49254(7) 0.01868(17) Uani 1 1 d . . . . .
C9 C 0.5687(4) 0.99820(18) 0.4800(5) 0.0299(12) Uani 1 1 d . . . . .
H9 H 0.525065 1.016635 0.536853 0.036 Uiso 1 1 calc R . . . .
C17 C 0.2221(4) 0.87259(16) 0.5557(5) 0.0212(10) Uani 1 1 d . . . . .
N2 N 0.4313(3) 0.89898(13) 0.5771(4) 0.0196(8) Uani 1 1 d . . . . .
N1 N 0.4992(3) 0.84441(14) 0.3904(3) 0.0180(9) Uani 1 1 d . . . . .
C22 C 0.3805(4) 0.84327(16) 0.4217(4) 0.0162(9) Uani 1 1 d . . . . .
C8 C 0.6925(4) 0.98546(16) 0.4848(5) 0.0278(11) Uani 1 1 d . . . . .
H8 H 0.747162 0.993491 0.545566 0.033 Uiso 1 1 calc R . . . .
C18 C 0.1931(5) 0.90078(18) 0.6547(5) 0.0262(11) Uani 1 1 d . . . . .
H18 H 0.111486 0.902208 0.681002 0.031 Uiso 1 1 calc R . . . .
C21 C 0.3441(4) 0.87256(16) 0.5202(4) 0.0185(10) Uani 1 1 d . . . . .
C14 C 0.2937(4) 0.81389(17) 0.3624(4) 0.0212(11) Uani 1 1 d . . . . .
C20 C 0.3999(4) 0.92424(18) 0.6712(4) 0.0245(11) Uani 1 1 d . . . . .
H20 H 0.461288 0.942014 0.711951 0.029 Uiso 1 1 calc R . . . .
C16 C 0.1352(4) 0.84397(17) 0.4900(5) 0.0256(10) Uani 1 1 d . . . . .
H16 H 0.051953 0.844876 0.511287 0.031 Uiso 1 1 calc R . . . .
C1 C 0.7144(4) 0.86660(19) 0.6562(4) 0.0250(11) Uani 1 1 d . . . . .
H1 H 0.701762 0.895281 0.703917 0.030 Uiso 1 1 calc R . . . .
C6 C 0.6138(4) 0.95469(17) 0.3163(5) 0.0230(11) Uani 1 1 d . . . . .
H6 H 0.606240 0.938515 0.243387 0.028 Uiso 1 1 calc R . . . .
C4 C 0.6969(4) 0.78856(18) 0.5779(5) 0.0269(11) Uani 1 1 d . . . . .
H4 H 0.670868 0.754987 0.563288 0.032 Uiso 1 1 calc R . . . .
C13 C 0.3349(5) 0.78513(17) 0.2686(4) 0.0233(11) Uani 1 1 d . . . . .
H13 H 0.279611 0.764792 0.226144 0.028 Uiso 1 1 calc R . . . .
C15 C 0.1698(4) 0.81602(19) 0.3991(5) 0.0264(12) Uani 1 1 d . . . . .
H15 H 0.110454 0.797163 0.358028 0.032 Uiso 1 1 calc R . . . .
C12 C 0.4547(4) 0.78640(18) 0.2383(4) 0.0228(11) Uani 1 1 d . . . . .
H12 H 0.483254 0.766690 0.175340 0.027 Uiso 1 1 calc R . . . .
C3 C 0.7873(4) 0.81412(18) 0.5170(4) 0.0249(11) Uani 1 1 d . . . . .
H3 H 0.832976 0.801322 0.453870 0.030 Uiso 1 1 calc R . . . .
C7 C 0.7209(4) 0.95860(17) 0.3831(4) 0.0230(11) Uani 1 1 d . . . . .
H7 H 0.798321 0.945447 0.363094 0.028 Uiso 1 1 calc R . . . .
C10 C 0.5211(5) 0.97902(17) 0.3772(5) 0.0267(12) Uani 1 1 d . . . . .
H10 H 0.439074 0.982008 0.352625 0.032 Uiso 1 1 calc R . . . .
C5 C 0.6511(5) 0.82020(19) 0.6634(4) 0.0244(11) Uani 1 1 d . . . . .
H5 H 0.588713 0.812126 0.716928 0.029 Uiso 1 1 calc R . . . .
Mn2 Mn 0.41977(6) 0.62166(3) 0.56558(7) 0.02356(19) Uani 1 1 d . . . . .
N3 N 0.5861(4) 0.59827(15) 0.6669(4) 0.0227(9) Uani 1 1 d . . . . .
N4 N 0.5806(4) 0.65368(15) 0.4702(4) 0.0258(10) Uani 1 1 d . . . . .
C31 C 0.3773(5) 0.72263(19) 0.5797(5) 0.0323(13) Uani 1 1 d . . . . .
H31 H 0.408676 0.747102 0.527716 0.039 Uiso 1 1 calc R . . . .
C41 C 0.6810(6) 0.70150(19) 0.3240(5) 0.0396(15) Uani 1 1 d . . . . .
H41 H 0.674709 0.721560 0.256283 0.048 Uiso 1 1 calc R . . . .
C36 C 0.8056(5) 0.5985(2) 0.6669(5) 0.0320(13) Uani 1 1 d . . . . .
C27 C 0.3702(5) 0.5254(2) 0.5658(6) 0.0369(13) Uani 1 1 d . . . . .
H27 H 0.401487 0.507403 0.630256 0.044 Uiso 1 1 calc R . . . .
C44 C 0.6928(5) 0.61259(18) 0.6200(5) 0.0255(12) Uani 1 1 d . . . . .
C33 C 0.5888(5) 0.56989(19) 0.7615(5) 0.0290(12) Uani 1 1 d . . . . .
H33 H 0.513706 0.560093 0.795133 0.035 Uiso 1 1 calc R . . . .
C42 C 0.5776(5) 0.6822(2) 0.3760(5) 0.0335(13) Uani 1 1 d . . . . .
H42 H 0.500937 0.689662 0.342569 0.040 Uiso 1 1 calc R . . . .
C39 C 0.8001(5) 0.6613(2) 0.4698(5) 0.0356(14) Uani 1 1 d . . . . .
C24 C 0.3590(6) 0.5676(2) 0.3974(5) 0.0416(15) Uani 1 1 d . . . . .
H24 H 0.379875 0.583444 0.326528 0.050 Uiso 1 1 calc R . . . .
C34 C 0.6957(5) 0.55373(19) 0.8141(5) 0.0341(13) Uani 1 1 d . . . . .
H34 H 0.693670 0.533253 0.881407 0.041 Uiso 1 1 calc R . . . .
C35 C 0.8034(5) 0.5681(2) 0.7663(5) 0.0363(14) Uani 1 1 d . . . . .
H35 H 0.877558 0.557472 0.800468 0.044 Uiso 1 1 calc R . . . .
C43 C 0.6898(5) 0.64325(17) 0.5179(4) 0.0259(12) Uani 1 1 d . . . . .
C30 C 0.2762(5) 0.6931(2) 0.5614(6) 0.0415(14) Uani 1 1 d . . . . .
H30 H 0.226470 0.692942 0.494340 0.050 Uiso 1 1 calc R . . . .
C32 C 0.4243(5) 0.7109(2) 0.6847(5) 0.0366(14) Uani 1 1 d . . . . .
H32 H 0.495143 0.725527 0.717285 0.044 Uiso 1 1 calc R . . . .
C40 C 0.7911(6) 0.6915(2) 0.3707(6) 0.0446(17) Uani 1 1 d . . . . .
H40 H 0.862313 0.705010 0.336330 0.054 Uiso 1 1 calc R . . . .
C38 C 0.9125(5) 0.6465(3) 0.5226(6) 0.050(2) Uani 1 1 d . . . . .
H38 H 0.986782 0.658724 0.491851 0.060 Uiso 1 1 calc R . . . .
C29 C 0.2607(6) 0.6631(2) 0.6608(7) 0.054(2) Uani 1 1 d . . . . .
H29 H 0.197625 0.639261 0.673555 0.065 Uiso 1 1 calc R . . . .
C2 C 0.7983(4) 0.86276(17) 0.5670(5) 0.0266(11) Uani 1 1 d . . . . .
H2 H 0.853477 0.888319 0.543496 0.032 Uiso 1 1 calc R . . . .
C19 C 0.2818(4) 0.92616(18) 0.7134(5) 0.0263(12) Uani 1 1 d . . . . .
H19 H 0.263152 0.944653 0.781476 0.032 Uiso 1 1 calc R . . . .
C11 C 0.5352(4) 0.81703(17) 0.3007(4) 0.0200(10) Uani 1 1 d . . . . .
H11 H 0.618080 0.818202 0.278064 0.024 Uiso 1 1 calc R . . . .
C26 C 0.2507(6) 0.53940(19) 0.5508(6) 0.0391(14) Uani 1 1 d . . . . .
H26 H 0.185257 0.532491 0.601932 0.047 Uiso 1 1 calc R . . . .
C25 C 0.2438(6) 0.5655(2) 0.4470(6) 0.0454(17) Uani 1 1 d . . . . .
H25 H 0.172134 0.579633 0.414970 0.054 Uiso 1 1 calc R . . . .
C37 C 0.9149(5) 0.6157(3) 0.6145(6) 0.0424(16) Uani 1 1 d . . . . .
H37 H 0.990770 0.605161 0.645104 0.051 Uiso 1 1 calc R . . . .
C23 C 0.4379(6) 0.5419(2) 0.4713(5) 0.0410(15) Uani 1 1 d . . . . .
H23 H 0.522320 0.536707 0.459338 0.049 Uiso 1 1 calc R . . . .
C28 C 0.3543(7) 0.6747(2) 0.7366(5) 0.0461(17) Uani 1 1 d . . . . .
H28 H 0.367320 0.660230 0.810693 0.055 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 N2 2.213(4) . ?
Mn1 N1 2.219(4) . ?
Mn1 C8 2.493(4) . ?
Mn1 C1 2.358(5) . ?
Mn1 C6 2.538(5) . ?
Mn1 C7 2.380(5) . ?
Mn1 C2 2.417(5) . ?
C9 C8 1.406(7) . ?
C9 C10 1.397(8) . ?
C17 C18 1.405(7) . ?
C17 C21 1.406(6) . ?
C17 C16 1.439(7) . ?
N2 C21 1.358(6) . ?
N2 C20 1.324(6) . ?
N1 C22 1.357(6) . ?
N1 C11 1.328(6) . ?
C22 C21 1.437(7) . ?
C22 C14 1.412(7) . ?
C8 C7 1.411(7) . ?
C18 C19 1.367(7) . ?
C14 C13 1.403(7) . ?
C14 C15 1.430(7) . ?
C20 C19 1.391(7) . ?
C16 C15 1.342(8) . ?
C1 C5 1.416(7) . ?
C1 C2 1.389(7) . ?
C6 C7 1.415(7) . ?
C6 C10 1.399(7) . ?
C4 C3 1.395(7) . ?
C4 C5 1.392(7) . ?
C13 C12 1.366(7) . ?
C12 C11 1.403(7) . ?
C3 C2 1.418(7) . ?
Mn2 N3 2.262(4) . ?
Mn2 N4 2.253(4) . ?
Mn2 C27 2.609(5) . ?
Mn2 C24 2.509(6) . ?
Mn2 C30 2.467(5) . ?
Mn2 C29 2.343(6) . ?
Mn2 C23 2.387(6) . ?
Mn2 C28 2.533(6) . ?
N3 C44 1.349(7) . ?
N3 C33 1.329(7) . ?
N4 C42 1.326(7) . ?
N4 C43 1.353(7) . ?
C31 C30 1.377(8) . ?
C31 C32 1.358(8) . ?
C41 C42 1.387(8) . ?
C41 C40 1.353(9) . ?
C36 C44 1.407(7) . ?
C36 C35 1.405(8) . ?
C36 C37 1.423(9) . ?
C27 C26 1.379(9) . ?
C27 C23 1.395(8) . ?
C44 C43 1.434(7) . ?
C33 C34 1.394(7) . ?
C39 C43 1.420(7) . ?
C39 C40 1.403(9) . ?
C39 C38 1.436(9) . ?
C24 C25 1.394(9) . ?
C24 C23 1.396(8) . ?
C34 C35 1.363(8) . ?
C30 C29 1.409(9) . ?
C32 C28 1.369(9) . ?
C38 C37 1.340(10) . ?
C29 C28 1.389(10) . ?
C26 C25 1.388(9) . ?

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 N1 75.30(14) . . ?
N2 Mn1 C8 108.87(15) . . ?
N2 Mn1 C1 94.66(16) . . ?
N2 Mn1 C6 110.88(16) . . ?
N2 Mn1 C7 132.85(15) . . ?
N2 Mn1 C2 127.72(17) . . ?
N1 Mn1 C8 140.78(17) . . ?
N1 Mn1 C1 118.27(16) . . ?
N1 Mn1 C6 87.49(15) . . ?
N1 Mn1 C7 115.50(16) . . ?
N1 Mn1 C2 114.86(15) . . ?
C8 Mn1 C6 54.02(18) . . ?
C1 Mn1 C8 100.52(18) . . ?
C1 Mn1 C6 148.09(17) . . ?
C1 Mn1 C7 114.87(17) . . ?
C1 Mn1 C2 33.80(18) . . ?
C7 Mn1 C8 33.56(18) . . ?
C7 Mn1 C6 33.24(16) . . ?
C7 Mn1 C2 91.01(17) . . ?
C2 Mn1 C8 93.72(17) . . ?
C2 Mn1 C6 120.37(17) . . ?
C10 C9 C8 108.1(5) . . ?
C18 C17 C21 117.1(4) . . ?
C18 C17 C16 124.1(5) . . ?
C21 C17 C16 118.8(5) . . ?
C21 N2 Mn1 114.3(3) . . ?
C20 N2 Mn1 127.3(3) . . ?
C20 N2 C21 118.3(4) . . ?
C22 N1 Mn1 114.1(3) . . ?
C11 N1 Mn1 126.8(3) . . ?
C11 N1 C22 119.0(4) . . ?
N1 C22 C21 118.0(4) . . ?
N1 C22 C14 122.4(4) . . ?
C14 C22 C21 119.7(4) . . ?
C9 C8 Mn1 83.0(3) . . ?
C9 C8 C7 107.7(5) . . ?
C7 C8 Mn1 68.8(2) . . ?
C19 C18 C17 120.3(5) . . ?
C17 C21 C22 119.9(4) . . ?
N2 C21 C17 122.3(4) . . ?
N2 C21 C22 117.8(4) . . ?
C22 C14 C15 118.7(5) . . ?
C13 C14 C22 117.2(4) . . ?
C13 C14 C15 124.1(5) . . ?
N2 C20 C19 123.5(5) . . ?
C15 C16 C17 121.1(4) . . ?
C5 C1 Mn1 96.6(3) . . ?
C2 C1 Mn1 75.4(3) . . ?
C2 C1 C5 107.9(4) . . ?
C7 C6 Mn1 67.2(3) . . ?
C10 C6 Mn1 82.0(3) . . ?
C10 C6 C7 107.4(5) . . ?
C5 C4 C3 109.0(4) . . ?
C12 C13 C14 119.9(4) . . ?
C16 C15 C14 121.7(5) . . ?
C13 C12 C11 119.5(5) . . ?
C4 C3 C2 107.2(4) . . ?
C8 C7 Mn1 77.6(3) . . ?
C8 C7 C6 108.0(4) . . ?
C6 C7 Mn1 79.5(3) . . ?
C9 C10 C6 108.8(4) . . ?
C4 C5 C1 107.6(4) . . ?
N3 Mn2 C27 84.31(17) . . ?
N3 Mn2 C24 117.50(18) . . ?
N3 Mn2 C30 137.71(18) . . ?
N3 Mn2 C29 119.4(2) . . ?
N3 Mn2 C23 85.79(18) . . ?
N3 Mn2 C28 88.7(2) . . ?
N4 Mn2 N3 73.78(15) . . ?
N4 Mn2 C27 122.23(17) . . ?
N4 Mn2 C24 92.55(19) . . ?
N4 Mn2 C30 101.83(19) . . ?
N4 Mn2 C29 129.94(18) . . ?
N4 Mn2 C23 92.49(17) . . ?
N4 Mn2 C28 113.5(2) . . ?
C24 Mn2 C27 52.14(19) . . ?
C24 Mn2 C28 148.0(2) . . ?
C30 Mn2 C27 128.05(19) . . ?
C30 Mn2 C24 104.6(2) . . ?
C30 Mn2 C28 53.6(2) . . ?
C29 Mn2 C27 107.5(2) . . ?
C29 Mn2 C24 115.7(2) . . ?
C29 Mn2 C30 33.9(2) . . ?
C29 Mn2 C23 133.8(2) . . ?
C29 Mn2 C28 32.8(2) . . ?
C23 Mn2 C27 32.0(2) . . ?
C23 Mn2 C24 33.0(2) . . ?
C23 Mn2 C30 136.4(2) . . ?
C23 Mn2 C28 150.8(2) . . ?
C28 Mn2 C27 118.8(2) . . ?
C44 N3 Mn2 114.8(3) . . ?
C33 N3 Mn2 126.9(3) . . ?
C33 N3 C44 118.1(4) . . ?
C42 N4 Mn2 126.7(4) . . ?
C42 N4 C43 118.3(5) . . ?
C43 N4 Mn2 115.0(3) . . ?
C32 C31 C30 108.4(5) . . ?
C40 C41 C42 119.4(6) . . ?
C44 C36 C37 119.8(6) . . ?
C35 C36 C44 117.0(5) . . ?
C35 C36 C37 123.2(5) . . ?
C26 C27 Mn2 86.4(3) . . ?
C26 C27 C23 109.1(6) . . ?
C23 C27 Mn2 65.2(3) . . ?
N3 C44 C36 122.6(5) . . ?
N3 C44 C43 118.1(5) . . ?
C36 C44 C43 119.3(5) . . ?
N3 C33 C34 123.5(5) . . ?
N4 C42 C41 123.2(6) . . ?
C43 C39 C38 118.6(6) . . ?
C40 C39 C43 116.9(5) . . ?
C40 C39 C38 124.5(5) . . ?
C25 C24 Mn2 86.9(4) . . ?
C25 C24 C23 107.1(5) . . ?
C23 C24 Mn2 68.7(3) . . ?
C35 C34 C33 118.2(6) . . ?
C34 C35 C36 120.5(5) . . ?
N4 C43 C44 118.2(5) . . ?
N4 C43 C39 122.1(5) . . ?
C39 C43 C44 119.6(5) . . ?
C31 C30 Mn2 85.2(3) . . ?
C31 C30 C29 107.1(6) . . ?
C29 C30 Mn2 68.2(3) . . ?
C31 C32 C28 109.8(6) . . ?
C41 C40 C39 120.1(5) . . ?
C37 C38 C39 121.4(6) . . ?
C30 C29 Mn2 77.8(3) . . ?
C28 C29 Mn2 81.1(4) . . ?
C28 C29 C30 107.5(5) . . ?
C1 C2 Mn1 70.8(3) . . ?
C1 C2 C3 108.2(4) . . ?
C3 C2 Mn1 97.5(3) . . ?
C18 C19 C20 118.4(5) . . ?
N1 C11 C12 122.0(5) . . ?
C27 C26 C25 107.1(6) . . ?
C26 C25 C24 109.1(6) . . ?
C38 C37 C36 121.1(6) . . ?
C27 C23 Mn2 82.8(4) . . ?
C27 C23 C24 107.5(6) . . ?
C24 C23 Mn2 78.3(3) . . ?
C32 C28 Mn2 83.4(3) . . ?
C32 C28 C29 107.2(5) . . ?
C29 C28 Mn2 66.1(3) . . ?

_olex2_submission_original_sample_id SKD-01-56
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.85(2)
2 0.15(2)

####################################################################### 
# 
# 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_lacy10_a
_database_code_depnum_ccdc_archive 'CCDC 1822544'
_audit_update_record             
;
2018-02-06 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H52 Mn2 N4 O'
_chemical_formula_weight         810.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   14.7987(8)
_cell_length_b                   16.8841(9)
_cell_length_c                   8.5878(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2145.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    5712
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      28.70

_exptl_crystal_description       Block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.628
_shelx_estimated_absorpt_T_min   0.806
_shelx_estimated_absorpt_T_max   0.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6619
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13495
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.830
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5537
_reflns_number_gt                4774
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1809 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.008(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5537
_refine_ls_number_parameters     273
_refine_ls_number_restraints     107
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn Mn 0.39988(2) 0.19231(2) 0.34047(5) 0.04389(12) Uani 1 1 d . . . . .
N1 N 0.30086(13) 0.28423(12) 0.2563(3) 0.0456(5) Uani 1 1 d . . . . .
N2 N 0.40756(13) 0.29056(11) 0.5141(2) 0.0442(4) Uani 1 1 d . . . . .
C1 C 0.4873(2) 0.1399(2) 0.0962(5) 0.0798(11) Uani 1 1 d . U . . .
H1 H 0.4518 0.1133 0.0222 0.096 Uiso 1 1 calc R U . . .
C2 C 0.4938(2) 0.2228(2) 0.1154(4) 0.0726(10) Uani 1 1 d . U . . .
H2 H 0.4651 0.2625 0.0565 0.087 Uiso 1 1 calc R U . . .
C3 C 0.5526(2) 0.2326(3) 0.2419(5) 0.0864(12) Uani 1 1 d . U . . .
H3 H 0.5699 0.2813 0.2857 0.104 Uiso 1 1 calc R U . . .
C4 C 0.5806(3) 0.1594(4) 0.2911(6) 0.119(2) Uani 1 1 d . U . . .
H4 H 0.6208 0.1494 0.3734 0.143 Uiso 1 1 calc R U . . .
C5 C 0.5417(3) 0.1058(3) 0.2038(7) 0.1077(18) Uani 1 1 d . U . . .
H5 H 0.5503 0.0509 0.2143 0.129 Uiso 1 1 calc R U . . .
C6 C 0.3752(2) 0.07224(18) 0.4831(6) 0.0788(11) Uani 1 1 d . U . . .
H6 H 0.4331 0.0493 0.4841 0.095 Uiso 1 1 calc R U . . .
C7 C 0.3156(2) 0.07267(18) 0.3580(6) 0.0795(11) Uani 1 1 d . U . . .
H7 H 0.3255 0.0503 0.2593 0.095 Uiso 1 1 calc R U . . .
C8 C 0.2376(3) 0.1129(2) 0.4073(7) 0.0936(14) Uani 1 1 d . U . . .
H8 H 0.1857 0.1222 0.3469 0.112 Uiso 1 1 calc R U . . .
C9 C 0.2505(3) 0.1366(2) 0.5611(7) 0.1043(17) Uani 1 1 d . U . . .
H9 H 0.2086 0.1647 0.6220 0.125 Uiso 1 1 calc R U . . .
C10 C 0.3337(3) 0.1124(2) 0.6085(6) 0.0947(13) Uani 1 1 d . U . . .
H10 H 0.3592 0.1209 0.7074 0.114 Uiso 1 1 calc R U . . .
C11 C 0.2614(3) 0.2098(3) 0.0211(5) 0.0960(14) Uani 1 1 d . . . . .
H11A H 0.3139 0.2140 -0.0461 0.144 Uiso 1 1 calc R U . . .
H11B H 0.2073 0.2053 -0.0422 0.144 Uiso 1 1 calc R U . . .
H11C H 0.2672 0.1633 0.0865 0.144 Uiso 1 1 calc R U . . .
C12 C 0.25496(18) 0.28187(19) 0.1210(4) 0.0570(7) Uani 1 1 d . . . . .
C13 C 0.20061(19) 0.3450(2) 0.0750(4) 0.0688(9) Uani 1 1 d . . . . .
H13 H 0.1694 0.3431 -0.0202 0.083 Uiso 1 1 calc R U . . .
C14 C 0.1931(2) 0.4095(2) 0.1691(5) 0.0772(10) Uani 1 1 d . . . . .
H14 H 0.1568 0.4525 0.1388 0.093 Uiso 1 1 calc R U . . .
C15 C 0.23884(19) 0.41178(17) 0.3088(4) 0.0636(8) Uani 1 1 d . . . . .
H15 H 0.2332 0.4555 0.3758 0.076 Uiso 1 1 calc R U . . .
C16 C 0.29330(15) 0.34816(13) 0.3484(4) 0.0451(5) Uani 1 1 d . . . . .
C17 C 0.34784(17) 0.34936(14) 0.4937(3) 0.0481(6) Uani 1 1 d . . . . .
C18 C 0.3404(3) 0.4109(2) 0.6003(5) 0.0770(10) Uani 1 1 d . . . . .
H18 H 0.2972 0.4510 0.5857 0.092 Uiso 1 1 calc R U . . .
C19 C 0.3968(3) 0.4126(2) 0.7273(5) 0.0942(13) Uani 1 1 d . . . . .
H19 H 0.3929 0.4541 0.7999 0.113 Uiso 1 1 calc R U . . .
C20 C 0.4576(3) 0.3542(2) 0.7463(4) 0.0830(11) Uani 1 1 d . . . . .
H20 H 0.4969 0.3552 0.8322 0.100 Uiso 1 1 calc R U . . .
C21 C 0.4626(2) 0.29300(18) 0.6408(3) 0.0591(7) Uani 1 1 d . . . . .
C22 C 0.5305(2) 0.2294(2) 0.6617(4) 0.0791(10) Uani 1 1 d . . . . .
H22A H 0.5083 0.1809 0.6147 0.119 Uiso 1 1 calc R U . . .
H22B H 0.5408 0.2209 0.7719 0.119 Uiso 1 1 calc R U . . .
H22C H 0.5866 0.2448 0.6121 0.119 Uiso 1 1 calc R U . . .
O1S O 0.4959(15) 0.4943(19) 0.0332(7) 0.130(4) Uani 0.5 1 d D . P A -1
C1S C 0.5582(15) 0.4570(10) 0.1283(19) 0.139(8) Uani 0.5 1 d D U P A -1
H1S1 H 0.6174 0.4823 0.1172 0.167 Uiso 0.5 1 calc R U P A -1
H1S2 H 0.5641 0.4012 0.0981 0.167 Uiso 0.5 1 calc R U P A -1
C2S C 0.5275(13) 0.4625(8) 0.2918(16) 0.093(4) Uani 0.5 1 d D U P A -1
H2S1 H 0.5004 0.4126 0.3267 0.111 Uiso 0.5 1 calc R U P A -1
H2S2 H 0.5775 0.4763 0.3614 0.111 Uiso 0.5 1 calc R U P A -1
C3S C 0.4622(11) 0.5240(13) 0.2857(17) 0.113(5) Uani 0.5 1 d D U P A -1
H3S1 H 0.4897 0.5751 0.3122 0.135 Uiso 0.5 1 calc R U P A -1
H3S2 H 0.4127 0.5135 0.3587 0.135 Uiso 0.5 1 calc R U P A -1
C4S C 0.4286(8) 0.5246(13) 0.124(2) 0.136(8) Uani 0.5 1 d D U P A -1
H4S1 H 0.3739 0.4922 0.1150 0.163 Uiso 0.5 1 calc R U P A -1
H4S2 H 0.4141 0.5788 0.0915 0.163 Uiso 0.5 1 calc R U P A -1


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn N2 2.234(2) . ?
Mn N1 2.254(2) . ?
Mn C7 2.379(3) . ?
Mn C6 2.397(3) . ?
Mn C2 2.436(3) . ?
Mn C3 2.507(3) . ?
Mn C1 2.619(4) . ?
N1 C16 1.343(3) . ?
N1 C12 1.347(4) . ?
N2 C17 1.341(3) . ?
N2 C21 1.360(4) . ?
C1 C5 1.353(6) . ?
C1 C2 1.413(5) . ?
C1 H1 0.9400 . ?
C2 C3 1.402(5) . ?
C2 H2 0.9400 . ?
C3 C4 1.371(7) . ?
C3 H3 0.9400 . ?
C4 C5 1.308(8) . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C6 C7 1.391(6) . ?
C6 C10 1.413(6) . ?
C6 H6 0.9400 . ?
C7 C8 1.404(5) . ?
C7 H7 0.9400 . ?
C8 C9 1.394(7) . ?
C8 H8 0.9400 . ?
C9 C10 1.360(7) . ?
C9 H9 0.9400 . ?
C10 H10 0.9400 . ?
C11 C12 1.492(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 C13 1.393(4) . ?
C13 C14 1.360(5) . ?
C13 H13 0.9400 . ?
C14 C15 1.378(5) . ?
C14 H14 0.9400 . ?
C15 C16 1.385(4) . ?
C15 H15 0.9400 . ?
C16 C17 1.487(4) . ?
C17 C18 1.389(4) . ?
C18 C19 1.373(6) . ?
C18 H18 0.9400 . ?
C19 C20 1.346(6) . ?
C19 H19 0.9400 . ?
C20 C21 1.376(5) . ?
C20 H20 0.9400 . ?
C21 C22 1.481(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
O1S C4S 1.365(15) . ?
O1S C1S 1.383(15) . ?
C1S C2S 1.478(14) . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C2S C3S 1.420(11) . ?
C2S H2S1 0.9800 . ?
C2S H2S2 0.9800 . ?
C3S C4S 1.475(15) . ?
C3S H3S1 0.9800 . ?
C3S H3S2 0.9800 . ?
C4S H4S1 0.9800 . ?
C4S H4S2 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 Mn N1 74.69(8) . . ?
N2 Mn C7 127.95(12) . . ?
N1 Mn C7 105.31(11) . . ?
N2 Mn C6 107.14(12) . . ?
N1 Mn C6 130.36(11) . . ?
C7 Mn C6 33.86(15) . . ?
N2 Mn C2 110.11(11) . . ?
N1 Mn C2 88.33(10) . . ?
C7 Mn C2 121.93(15) . . ?
C6 Mn C2 132.16(12) . . ?
N2 Mn C3 88.74(11) . . ?
N1 Mn C3 106.90(13) . . ?
C7 Mn C3 136.43(14) . . ?
C6 Mn C3 122.64(14) . . ?
C2 Mn C3 32.90(13) . . ?
N2 Mn C1 139.52(10) . . ?
N1 Mn C1 107.28(11) . . ?
C7 Mn C1 91.31(13) . . ?
C6 Mn C1 101.46(13) . . ?
C2 Mn C1 32.20(12) . . ?
C3 Mn C1 51.38(12) . . ?
C16 N1 C12 119.3(2) . . ?
C16 N1 Mn 114.76(17) . . ?
C12 N1 Mn 125.77(18) . . ?
C17 N2 C21 118.5(2) . . ?
C17 N2 Mn 115.41(17) . . ?
C21 N2 Mn 125.97(18) . . ?
C5 C1 C2 107.6(4) . . ?
C5 C1 Mn 83.7(3) . . ?
C2 C1 Mn 66.7(2) . . ?
C5 C1 H1 126.2 . . ?
C2 C1 H1 126.2 . . ?
Mn C1 H1 115.3 . . ?
C3 C2 C1 104.5(3) . . ?
C3 C2 Mn 76.4(2) . . ?
C1 C2 Mn 81.0(2) . . ?
C3 C2 H2 127.8 . . ?
C1 C2 H2 127.8 . . ?
Mn C2 H2 108.6 . . ?
C4 C3 C2 108.7(4) . . ?
C4 C3 Mn 85.6(3) . . ?
C2 C3 Mn 70.74(18) . . ?
C4 C3 H3 125.7 . . ?
C2 C3 H3 125.7 . . ?
Mn C3 H3 110.4 . . ?
C5 C4 C3 108.3(4) . . ?
C5 C4 H4 125.9 . . ?
C3 C4 H4 125.9 . . ?
C4 C5 C1 111.0(5) . . ?
C4 C5 H5 124.5 . . ?
C1 C5 H5 124.5 . . ?
C7 C6 C10 108.0(3) . . ?
C7 C6 Mn 72.4(2) . . ?
C10 C6 Mn 92.9(2) . . ?
C7 C6 H6 126.0 . . ?
C10 C6 H6 126.0 . . ?
Mn C6 H6 102.4 . . ?
C6 C7 C8 107.0(4) . . ?
C6 C7 Mn 73.76(19) . . ?
C8 C7 Mn 92.2(2) . . ?
C6 C7 H7 126.5 . . ?
C8 C7 H7 126.5 . . ?
Mn C7 H7 101.7 . . ?
C9 C8 C7 108.2(5) . . ?
C9 C8 H8 125.9 . . ?
C7 C8 H8 125.9 . . ?
C10 C9 C8 108.7(4) . . ?
C10 C9 H9 125.6 . . ?
C8 C9 H9 125.6 . . ?
C9 C10 C6 108.1(5) . . ?
C9 C10 H10 126.0 . . ?
C6 C10 H10 126.0 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 120.9(3) . . ?
N1 C12 C11 119.2(3) . . ?
C13 C12 C11 119.9(3) . . ?
C14 C13 C12 119.4(3) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 118.5(3) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
N1 C16 C15 121.8(3) . . ?
N1 C16 C17 117.4(2) . . ?
C15 C16 C17 120.7(3) . . ?
N2 C17 C18 121.3(3) . . ?
N2 C17 C16 117.2(2) . . ?
C18 C17 C16 121.4(3) . . ?
C19 C18 C17 119.4(3) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C20 C19 C18 119.1(3) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
N2 C21 C20 121.2(3) . . ?
N2 C21 C22 118.7(3) . . ?
C20 C21 C22 120.1(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C4S O1S C1S 108.7(7) . . ?
O1S C1S C2S 109.1(12) . . ?
O1S C1S H1S1 109.9 . . ?
C2S C1S H1S1 109.9 . . ?
O1S C1S H1S2 109.9 . . ?
C2S C1S H1S2 109.9 . . ?
H1S1 C1S H1S2 108.3 . . ?
C3S C2S C1S 102.7(12) . . ?
C3S C2S H2S1 111.2 . . ?
C1S C2S H2S1 111.2 . . ?
C3S C2S H2S2 111.2 . . ?
C1S C2S H2S2 111.2 . . ?
H2S1 C2S H2S2 109.1 . . ?
C2S C3S C4S 105.6(13) . . ?
C2S C3S H3S1 110.6 . . ?
C4S C3S H3S1 110.6 . . ?
C2S C3S H3S2 110.6 . . ?
C4S C3S H3S2 110.6 . . ?
H3S1 C3S H3S2 108.8 . . ?
O1S C4S C3S 106.8(10) . . ?
O1S C4S H4S1 110.4 . . ?
C3S C4S H4S1 110.4 . . ?
O1S C4S H4S2 110.4 . . ?
C3S C4S H4S2 110.4 . . ?
H4S1 C4S H4S2 108.6 . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_lacy9_b
_database_code_depnum_ccdc_archive 'CCDC 1822542'
_audit_update_record             
;
2018-02-06 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Mn N2'
_chemical_formula_weight         343.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'A b a 2'
_space_group_name_Hall           'A 2 -2ac'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, z+1/2'

_cell_length_a                   7.8832(7)
_cell_length_b                   17.6630(19)
_cell_length_c                   12.5197(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1743.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    1331
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      24.03

_exptl_crystal_description       Plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             716
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.758
_shelx_estimated_absorpt_T_min   0.794
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6610
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5214
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.306
_diffrn_reflns_theta_max         28.271
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2092
_reflns_number_gt                1631
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_max     0.915
_reflns_Friedel_fraction_full    0.970

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0416P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 621 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.05(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2092
_refine_ls_number_parameters     105
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn Mn 0.5000 0.5000 0.56849(13) 0.0451(2) Uani 1 2 d S T P . .
N N 0.6064(3) 0.41998(16) 0.4505(2) 0.0445(7) Uani 1 1 d . . . . .
C1 C 0.7440(6) 0.5347(3) 0.6604(4) 0.0707(12) Uani 1 1 d . . . . .
H1 H 0.7721 0.4862 0.6860 0.085 Uiso 1 1 calc R U . . .
C2 C 0.6251(6) 0.5853(3) 0.7056(4) 0.0791(15) Uani 1 1 d . . . . .
H2 H 0.5589 0.5767 0.7669 0.095 Uiso 1 1 calc R U . . .
C3 C 0.6242(6) 0.6493(3) 0.6434(5) 0.0853(18) Uani 1 1 d . . . . .
H3 H 0.5562 0.6923 0.6547 0.102 Uiso 1 1 calc R U . . .
C4 C 0.7392(6) 0.6401(2) 0.5620(6) 0.0752(11) Uani 1 1 d . . . . .
H4 H 0.7643 0.6759 0.5088 0.090 Uiso 1 1 calc R U . . .
C5 C 0.8110(4) 0.5699(2) 0.5716(5) 0.0674(10) Uani 1 1 d . . . . .
H5 H 0.8925 0.5491 0.5253 0.081 Uiso 1 1 calc R U . . .
C6 C 0.7497(5) 0.3816(2) 0.4698(3) 0.0521(9) Uani 1 1 d . . . . .
H6 H 0.8128 0.3936 0.5312 0.062 Uiso 1 1 calc R U . . .
C7 C 0.8077(5) 0.3258(2) 0.4038(4) 0.0655(11) Uani 1 1 d . . . . .
H7 H 0.9087 0.3000 0.4202 0.079 Uiso 1 1 calc R U . . .
C8 C 0.7189(6) 0.3078(2) 0.3143(5) 0.0693(12) Uani 1 1 d . . . . .
H8 H 0.7573 0.2695 0.2680 0.083 Uiso 1 1 calc R U . . .
C9 C 0.5716(5) 0.3467(2) 0.2929(3) 0.0573(9) Uani 1 1 d . . . . .
H9 H 0.5078 0.3358 0.2314 0.069 Uiso 1 1 calc R U . . .
C10 C 0.5196(4) 0.4018(2) 0.3630(3) 0.0472(8) Uani 1 1 d . . . . .
H10 H 0.4182 0.4278 0.3485 0.057 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn N 2.210(3) . ?
Mn N 2.210(3) 2_665 ?
Mn C1 2.324(4) . ?
Mn C1 2.324(4) 2_665 ?
Mn C2 2.488(4) . ?
Mn C2 2.488(4) 2_665 ?
N C10 1.331(5) . ?
N C6 1.339(5) . ?
C1 C5 1.379(7) . ?
C1 C2 1.413(7) . ?
C1 H1 0.9400 . ?
C2 C3 1.373(8) . ?
C2 H2 0.9400 . ?
C3 C4 1.373(8) . ?
C3 H3 0.9400 . ?
C4 C5 1.368(5) . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C6 C7 1.365(6) . ?
C6 H6 0.9400 . ?
C7 C8 1.359(7) . ?
C7 H7 0.9400 . ?
C8 C9 1.376(6) . ?
C8 H8 0.9400 . ?
C9 C10 1.373(6) . ?
C9 H9 0.9400 . ?
C10 H10 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
N Mn N 96.10(16) . 2_665 ?
N Mn C1 100.69(15) . . ?
N Mn C1 118.48(14) 2_665 . ?
N Mn C1 118.48(14) . 2_665 ?
N Mn C1 100.69(15) 2_665 2_665 ?
C1 Mn C1 120.6(3) . 2_665 ?
N Mn C2 134.26(12) . . ?
N Mn C2 102.98(15) 2_665 . ?
C1 Mn C2 33.94(15) . . ?
C1 Mn C2 98.39(19) 2_665 . ?
N Mn C2 102.97(15) . 2_665 ?
N Mn C2 134.26(12) 2_665 2_665 ?
C1 Mn C2 98.39(19) . 2_665 ?
C1 Mn C2 33.94(15) 2_665 2_665 ?
C2 Mn C2 92.7(3) . 2_665 ?
C10 N C6 117.4(3) . . ?
C10 N Mn 120.6(2) . . ?
C6 N Mn 121.5(3) . . ?
C5 C1 C2 106.9(4) . . ?
C5 C1 Mn 92.1(3) . . ?
C2 C1 Mn 79.4(3) . . ?
C5 C1 H1 126.5 . . ?
C2 C1 H1 126.5 . . ?
Mn C1 H1 97.1 . . ?
C3 C2 C1 107.3(5) . . ?
C3 C2 Mn 96.1(3) . . ?
C1 C2 Mn 66.7(2) . . ?
C3 C2 H2 126.3 . . ?
C1 C2 H2 126.3 . . ?
Mn C2 H2 104.2 . . ?
C2 C3 C4 108.6(4) . . ?
C2 C3 H3 125.7 . . ?
C4 C3 H3 125.7 . . ?
C5 C4 C3 108.4(6) . . ?
C5 C4 H4 125.8 . . ?
C3 C4 H4 125.8 . . ?
C4 C5 C1 108.7(5) . . ?
C4 C5 H5 125.6 . . ?
C1 C5 H5 125.6 . . ?
N C6 C7 122.6(4) . . ?
N C6 H6 118.7 . . ?
C7 C6 H6 118.7 . . ?
C8 C7 C6 119.7(4) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 118.5(4) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C10 C9 C8 118.8(4) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
N C10 C9 122.9(4) . . ?
N C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_dcl-005-skd-086
_database_code_depnum_ccdc_archive 'CCDC 1822541'
_audit_update_record             
;
2018-02-06 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2018-02-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.75(C25 H21 Mn N3), 0.75(C4 H8 O)'
_chemical_formula_sum            'C21.75 H21.75 Mn0.75 N2.25 O0.75'
_chemical_formula_weight         367.87
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   14.905(2)
_cell_length_b                   16.420(3)
_cell_length_c                   16.608(3)
_cell_angle_alpha                94.364(4)
_cell_angle_beta                 91.606(4)
_cell_angle_gamma                115.268(3)
_cell_volume                     3656.7(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    90
_cell_measurement_theta_max      30.82
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.568
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1396 before and 0.0454 after correction. The Ratio of minimum to maximum transmission is 0.8232. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1542
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            50450
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.140
_diffrn_reflns_theta_min         1.514
_diffrn_ambient_temperature      90
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus rotating anode'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                16541
_reflns_number_total             23321
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.975
_refine_diff_density_min         -0.825
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     919
_refine_ls_number_reflns         23321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²+2.4868P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1312
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C85(H85A,H85B), C86(H86A,H86B), C84(H84A,H84B), C76(H76A,H76B), C77(H77A,
 H77B), C78(H78A,H78B), C79(H79A,H79B), C82(H82A,H82B), C83(H83A,H83B),
 C81(H81A,H81B), C80(H80A,H80B), C0AA(H0AA,H0AB)
2.b Aromatic/amide H refined with riding coordinates:
 C37(H37), C50(H50), C48(H48), C47(H47), C27(H27), C44(H44), C32(H32),
 C26(H26), C42(H42), C39(H39), C36(H36), C43(H43), C28(H28), C49(H49), C38(H38),
  C31(H31), C35(H35), C30(H30), C29(H29), C33(H33), C34(H34), C69(H69),
 C57(H57), C68(H68), C67(H67), C51(H51), C56(H56), C55(H55), C64(H64), C54(H54),
  C58(H58), C61(H61), C52(H52), C63(H63), C53(H53), C72(H72), C75(H75),
 C59(H59), C62(H62), C74(H74), C60(H60), C73(H73), C14(H14), C13(H13), C17(H17),
  C19(H19), C22(H22), C12(H12), C25(H25), C11(H11), C24(H24), C23(H23), C3(H3),
 C2(H2), C1(H1), C5(H5), C18(H18), C4(H4), C9(H9), C10(H10), C8(H8), C6(H6),
 C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn2 Mn 0.80102(2) 0.56260(2) 0.56911(2) 0.01644(6) Uani 1 1 d . . . . .
N4 N 0.72427(11) 0.60897(11) 0.66730(10) 0.0185(3) Uani 1 1 d . . . . .
N6 N 0.76490(11) 0.47645(11) 0.44134(10) 0.0183(3) Uani 1 1 d . . . . .
N5 N 0.63777(11) 0.47786(11) 0.54850(10) 0.0168(3) Uani 1 1 d . . . . .
C46 C 0.67212(13) 0.40881(12) 0.42858(11) 0.0174(3) Uani 1 1 d . . . . .
C41 C 0.57695(13) 0.48886(13) 0.60170(12) 0.0187(4) Uani 1 1 d . . . . .
C45 C 0.60010(13) 0.41300(13) 0.48607(12) 0.0184(4) Uani 1 1 d . . . . .
C37 C 0.72375(16) 0.69691(14) 0.78908(13) 0.0251(4) Uani 1 1 d . . . . .
H37 H 0.759959 0.743990 0.830419 0.030 Uiso 1 1 calc R . . . .
C50 C 0.83286(14) 0.47712(14) 0.39013(12) 0.0216(4) Uani 1 1 d . . . . .
H50 H 0.898116 0.524642 0.398667 0.026 Uiso 1 1 calc R . . . .
C40 C 0.62476(14) 0.56245(13) 0.66781(12) 0.0186(4) Uani 1 1 d . . . . .
C48 C 0.71822(16) 0.34303(14) 0.31276(12) 0.0241(4) Uani 1 1 d . . . . .
H48 H 0.702414 0.297437 0.268940 0.029 Uiso 1 1 calc R . . . .
C47 C 0.64635(15) 0.34095(13) 0.36483(12) 0.0221(4) Uani 1 1 d . . . . .
H47 H 0.580647 0.294061 0.357195 0.027 Uiso 1 1 calc R . . . .
C27 C 0.83360(15) 0.71192(14) 0.47941(13) 0.0249(4) Uani 1 1 d . . . . .
H27 H 0.794728 0.685362 0.429993 0.030 Uiso 1 1 calc R . . . .
C44 C 0.49924(14) 0.35489(14) 0.47603(13) 0.0245(4) Uani 1 1 d . . . . .
H44 H 0.474037 0.308351 0.432538 0.029 Uiso 1 1 calc R . . . .
C32 C 0.93051(16) 0.51327(16) 0.60135(14) 0.0298(5) Uani 1 1 d . . . . .
H32 H 0.983230 0.542496 0.567754 0.036 Uiso 1 1 calc R . . . .
C26 C 0.90961(15) 0.69171(14) 0.51148(13) 0.0234(4) Uani 1 1 d . . . . .
H26 H 0.931194 0.649270 0.487646 0.028 Uiso 1 1 calc R . . . .
C42 C 0.47463(14) 0.43355(14) 0.59428(14) 0.0253(4) Uani 1 1 d . . . . .
H42 H 0.432128 0.442015 0.632248 0.030 Uiso 1 1 calc R . . . .
C39 C 0.57123(15) 0.58171(14) 0.72758(13) 0.0238(4) Uani 1 1 d . . . . .
H39 H 0.501022 0.548610 0.726445 0.029 Uiso 1 1 calc R . . . .
C36 C 0.77168(15) 0.67376(14) 0.72778(12) 0.0221(4) Uani 1 1 d . . . . .
H36 H 0.842009 0.705433 0.728495 0.026 Uiso 1 1 calc R . . . .
C43 C 0.43659(15) 0.36649(15) 0.53080(15) 0.0300(5) Uani 1 1 d . . . . .
H43 H 0.367275 0.328249 0.524746 0.036 Uiso 1 1 calc R . . . .
C28 C 0.82558(17) 0.77769(15) 0.53298(15) 0.0303(5) Uani 1 1 d . . . . .
H28 H 0.780064 0.803594 0.526378 0.036 Uiso 1 1 calc R . . . .
C49 C 0.81325(15) 0.41229(14) 0.32533(13) 0.0243(4) Uani 1 1 d . . . . .
H49 H 0.863757 0.415295 0.290414 0.029 Uiso 1 1 calc R . . . .
C38 C 0.62168(16) 0.64971(15) 0.78862(13) 0.0263(4) Uani 1 1 d . . . . .
H38 H 0.586429 0.663899 0.829977 0.032 Uiso 1 1 calc R . . . .
C31 C 0.91317(15) 0.55143(15) 0.67540(14) 0.0277(4) Uani 1 1 d . . . . .
H31 H 0.952308 0.610754 0.700505 0.033 Uiso 1 1 calc R . . . .
C35 C 0.82745(16) 0.48547(17) 0.70495(16) 0.0322(5) Uani 1 1 d . . . . .
H35 H 0.798414 0.492480 0.753643 0.039 Uiso 1 1 calc R . . . .
C30 C 0.94788(16) 0.74647(14) 0.58590(13) 0.0283(5) Uani 1 1 d . . . . .
H30 H 0.999614 0.747111 0.621064 0.034 Uiso 1 1 calc R . . . .
C29 C 0.89590(18) 0.79911(14) 0.59810(14) 0.0324(5) Uani 1 1 d . . . . .
H29 H 0.906454 0.842271 0.643071 0.039 Uiso 1 1 calc R . . . .
C33 C 0.85556(19) 0.42433(17) 0.58662(15) 0.0356(5) Uani 1 1 d . . . . .
H33 H 0.848964 0.382697 0.541343 0.043 Uiso 1 1 calc R . . . .
C34 C 0.79250(17) 0.40786(17) 0.65016(16) 0.0367(6) Uani 1 1 d . . . . .
H34 H 0.735425 0.353076 0.655273 0.044 Uiso 1 1 calc R . . . .
Mn3 Mn 0.69613(2) 0.02786(2) 0.71561(2) 0.01985(7) Uani 1 1 d . . . . .
N8 N 0.83774(11) 0.04473(10) 0.66010(10) 0.0175(3) Uani 1 1 d . . . . .
C70 C 0.86107(13) 0.07944(12) 0.58873(11) 0.0172(3) Uani 1 1 d . . . . .
C66 C 0.89931(14) 0.01806(12) 0.69911(11) 0.0179(3) Uani 1 1 d . . . . .
N7 N 0.78076(12) -0.01757(11) 0.80081(10) 0.0208(3) Uani 1 1 d . . . . .
C65 C 0.86620(14) -0.01831(12) 0.77782(12) 0.0198(4) Uani 1 1 d . . . . .
N9 N 0.70970(12) 0.09752(11) 0.59470(10) 0.0209(3) Uani 1 1 d . . . . .
C69 C 0.94717(14) 0.08734(13) 0.55270(12) 0.0191(4) Uani 1 1 d . . . . .
H69 H 0.962128 0.111001 0.501779 0.023 Uiso 1 1 calc R . . . .
C57 C 0.60105(16) -0.11812(14) 0.62257(14) 0.0285(5) Uani 1 1 d . . . . .
H57 H 0.629550 -0.108156 0.571705 0.034 Uiso 1 1 calc R . . . .
C68 C 1.01055(14) 0.05982(13) 0.59298(12) 0.0207(4) Uani 1 1 d . . . . .
H68 H 1.069707 0.064247 0.569587 0.025 Uiso 1 1 calc R . . . .
C71 C 0.79021(14) 0.11139(13) 0.55357(12) 0.0194(4) Uani 1 1 d . . . . .
C67 C 0.98774(14) 0.02590(13) 0.66723(12) 0.0208(4) Uani 1 1 d . . . . .
H67 H 1.031567 0.008277 0.695935 0.025 Uiso 1 1 calc R . . . .
C51 C 0.65739(16) 0.13964(14) 0.78276(14) 0.0273(4) Uani 1 1 d . . . . .
H51 H 0.603383 0.126283 0.744341 0.033 Uiso 1 1 calc R . . . .
C56 C 0.53748(16) -0.08121(15) 0.65493(15) 0.0307(5) Uani 1 1 d . . . . .
H56 H 0.516295 -0.041792 0.629702 0.037 Uiso 1 1 calc R . . . .
C55 C 0.76061(15) 0.19119(14) 0.77169(13) 0.0238(4) Uani 1 1 d . . . . .
H55 H 0.787393 0.219371 0.724510 0.029 Uiso 1 1 calc R . . . .
C64 C 0.92001(16) -0.05072(14) 0.82463(13) 0.0260(4) Uani 1 1 d . . . . .
H64 H 0.979450 -0.051750 0.806533 0.031 Uiso 1 1 calc R . . . .
C54 C 0.81527(16) 0.19306(14) 0.84192(13) 0.0253(4) Uani 1 1 d . . . . .
H54 H 0.885670 0.221517 0.850435 0.030 Uiso 1 1 calc R . . . .
C58 C 0.61406(16) -0.17189(14) 0.67930(14) 0.0276(4) Uani 1 1 d . . . . .
H58 H 0.653706 -0.204220 0.673913 0.033 Uiso 1 1 calc R . . . .
C61 C 0.74783(17) -0.04798(13) 0.87203(13) 0.0256(4) Uani 1 1 d . . . . .
H61 H 0.687430 -0.047654 0.888440 0.031 Uiso 1 1 calc R . . . .
C52 C 0.65126(17) 0.11248(14) 0.86173(14) 0.0316(5) Uani 1 1 d . . . . .
H52 H 0.591768 0.077723 0.886316 0.038 Uiso 1 1 calc R . . . .
C63 C 0.88550(18) -0.08173(14) 0.89862(14) 0.0301(5) Uani 1 1 d . . . . .
H63 H 0.921215 -0.103834 0.932063 0.036 Uiso 1 1 calc R . . . .
C53 C 0.74807(18) 0.14555(14) 0.89778(13) 0.0298(5) Uani 1 1 d . . . . .
H53 H 0.765216 0.137181 0.951043 0.036 Uiso 1 1 calc R . . . .
C72 C 0.80775(16) 0.15601(15) 0.48336(14) 0.0280(4) Uani 1 1 d . . . . .
H72 H 0.865115 0.165016 0.454847 0.034 Uiso 1 1 calc R . . . .
C75 C 0.64554(15) 0.12844(15) 0.56719(14) 0.0263(4) Uani 1 1 d . . . . .
H75 H 0.588577 0.118724 0.596487 0.032 Uiso 1 1 calc R . . . .
C59 C 0.55826(17) -0.16959(16) 0.74548(14) 0.0314(5) Uani 1 1 d . . . . .
H59 H 0.552974 -0.200788 0.792287 0.038 Uiso 1 1 calc R . . . .
C62 C 0.79860(18) -0.07973(14) 0.92233(13) 0.0290(5) Uani 1 1 d . . . . .
H62 H 0.773813 -0.099955 0.972740 0.035 Uiso 1 1 calc R . . . .
C74 C 0.65812(17) 0.17355(15) 0.49858(15) 0.0307(5) Uani 1 1 d . . . . .
H74 H 0.611303 0.194781 0.481295 0.037 Uiso 1 1 calc R . . . .
C60 C 0.51167(16) -0.11337(15) 0.73064(15) 0.0311(5) Uani 1 1 d . . . . .
H60 H 0.469875 -0.099506 0.765817 0.037 Uiso 1 1 calc R . . . .
C73 C 0.74050(18) 0.18702(17) 0.45576(15) 0.0336(5) Uani 1 1 d . . . . .
H73 H 0.750994 0.217198 0.407901 0.040 Uiso 1 1 calc R . . . .
Mn1 Mn 0.77078(2) 0.58819(2) 0.07028(2) 0.01901(7) Uani 1 1 d . . . . .
N3 N 0.71597(11) 0.48578(11) -0.04727(10) 0.0191(3) Uani 1 1 d . . . . .
N1 N 0.88831(11) 0.64024(10) 0.17238(9) 0.0168(3) Uani 1 1 d . . . . .
C15 C 0.94135(12) 0.59284(12) 0.18554(11) 0.0154(3) Uani 1 1 d . . . . .
N2 N 0.85209(11) 0.50091(10) 0.06511(9) 0.0155(3) Uani 1 1 d . . . . .
C16 C 0.92358(13) 0.51671(12) 0.12347(11) 0.0159(3) Uani 1 1 d . . . . .
C14 C 1.00654(13) 0.61283(13) 0.25342(11) 0.0184(4) Uani 1 1 d . . . . .
H14 H 1.044281 0.579377 0.260647 0.022 Uiso 1 1 calc R . . . .
C13 C 1.01536(14) 0.68255(13) 0.31034(12) 0.0207(4) Uani 1 1 d . . . . .
H13 H 1.058642 0.697038 0.357659 0.025 Uiso 1 1 calc R . . . .
C17 C 0.97650(14) 0.46442(14) 0.12461(12) 0.0215(4) Uani 1 1 d . . . . .
H17 H 1.027152 0.476560 0.165941 0.026 Uiso 1 1 calc R . . . .
C19 C 0.87936(15) 0.37736(13) 0.00422(12) 0.0220(4) Uani 1 1 d . . . . .
H19 H 0.862698 0.329189 -0.037301 0.026 Uiso 1 1 calc R . . . .
C22 C 0.71618(14) 0.35229(13) -0.11765(12) 0.0207(4) Uani 1 1 d . . . . .
H22 H 0.741668 0.308170 -0.121543 0.025 Uiso 1 1 calc R . . . .
C21 C 0.75121(13) 0.42244(12) -0.05555(11) 0.0171(3) Uani 1 1 d . . . . .
C20 C 0.82990(13) 0.43274(12) 0.00649(11) 0.0164(3) Uani 1 1 d . . . . .
C12 C 0.96052(14) 0.73072(13) 0.29748(12) 0.0207(4) Uani 1 1 d . . . . .
H12 H 0.965078 0.778431 0.335948 0.025 Uiso 1 1 calc R . . . .
C25 C 0.64552(14) 0.48019(14) -0.10229(12) 0.0219(4) Uani 1 1 d . . . . .
H25 H 0.620453 0.524563 -0.097052 0.026 Uiso 1 1 calc R . . . .
C11 C 0.89901(14) 0.70836(13) 0.22780(12) 0.0198(4) Uani 1 1 d . . . . .
H11 H 0.862631 0.742612 0.218575 0.024 Uiso 1 1 calc R . . . .
C24 C 0.60720(14) 0.41309(14) -0.16650(12) 0.0227(4) Uani 1 1 d . . . . .
H24 H 0.557580 0.411845 -0.204400 0.027 Uiso 1 1 calc R . . . .
C23 C 0.64310(15) 0.34822(14) -0.17383(12) 0.0235(4) Uani 1 1 d . . . . .
H23 H 0.618071 0.301188 -0.216907 0.028 Uiso 1 1 calc R . . . .
C3 C 0.95259(16) 0.76848(14) 0.01017(14) 0.0270(4) Uani 1 1 d . . . . .
H3 H 1.019052 0.778634 0.001186 0.032 Uiso 1 1 calc R . . . .
C2 C 0.86695(15) 0.70396(14) -0.03394(13) 0.0240(4) Uani 1 1 d . . . . .
H2 H 0.865288 0.663334 -0.078479 0.029 Uiso 1 1 calc R . . . .
C1 C 0.78314(16) 0.70989(14) -0.00046(13) 0.0246(4) Uani 1 1 d . . . . .
H1 H 0.715391 0.673771 -0.018051 0.029 Uiso 1 1 calc R . . . .
C5 C 0.81936(18) 0.77981(15) 0.06415(13) 0.0285(5) Uani 1 1 d . . . . .
H5 H 0.780166 0.799137 0.097724 0.034 Uiso 1 1 calc R . . . .
C18 C 0.95372(16) 0.39440(14) 0.06424(13) 0.0255(4) Uani 1 1 d . . . . .
H18 H 0.988955 0.357929 0.063825 0.031 Uiso 1 1 calc R . . . .
C4 C 0.92335(18) 0.81524(14) 0.06957(14) 0.0298(5) Uani 1 1 d . . . . .
H4 H 0.966814 0.863219 0.107473 0.036 Uiso 1 1 calc R . . . .
C9 C 0.67766(16) 0.53098(16) 0.23220(15) 0.0313(5) Uani 1 1 d . . . . .
H9 H 0.707343 0.522428 0.280252 0.038 Uiso 1 1 calc R . . . .
C10 C 0.64323(18) 0.4704(2) 0.16468(18) 0.0420(6) Uani 1 1 d . . . . .
H10 H 0.644833 0.413112 0.157237 0.050 Uiso 1 1 calc R . . . .
C8 C 0.66230(19) 0.60766(19) 0.2194(2) 0.0460(7) Uani 1 1 d . . . . .
H8 H 0.679370 0.659611 0.256743 0.055 Uiso 1 1 calc R . . . .
C6 C 0.6046(2) 0.5097(3) 0.10784(18) 0.0650(11) Uani 1 1 d . . . . .
H6 H 0.574940 0.483193 0.055306 0.078 Uiso 1 1 calc R . . . .
C7 C 0.6180(2) 0.5937(3) 0.1428(3) 0.0689(12) Uani 1 1 d . . . . .
H7 H 0.599539 0.634970 0.117927 0.083 Uiso 1 1 calc R . . . .
O3 O 0.44283(15) 0.14720(16) 0.63932(16) 0.0649(7) Uani 1 1 d . . . . .
C85 C 0.27021(18) 0.06766(18) 0.61507(17) 0.0379(6) Uani 1 1 d . . . . .
H85A H 0.215149 0.016612 0.636691 0.046 Uiso 1 1 calc R . . . .
H85B H 0.252060 0.070374 0.557866 0.046 Uiso 1 1 calc R . . . .
C86 C 0.29296(19) 0.15699(18) 0.66559(17) 0.0389(6) Uani 1 1 d . . . . .
H86A H 0.278704 0.198783 0.633180 0.047 Uiso 1 1 calc R . . . .
H86B H 0.253383 0.146568 0.713825 0.047 Uiso 1 1 calc R . . . .
C84 C 0.3664(2) 0.0576(2) 0.6228(2) 0.0468(7) Uani 1 1 d . . . . .
H84A H 0.365325 0.020621 0.667417 0.056 Uiso 1 1 calc R . . . .
H84B H 0.376866 0.028295 0.571877 0.056 Uiso 1 1 calc R . . . .
O1 O 0.44145(15) 0.09352(13) -0.01736(13) 0.0487(5) Uani 1 1 d . . . . .
O2 O 0.86542(16) 0.06409(16) 0.22746(13) 0.0555(5) Uani 1 1 d . . . . .
C76 C 0.52020(19) 0.11646(17) 0.04403(16) 0.0380(6) Uani 1 1 d . . . . .
H76A H 0.563513 0.086688 0.028692 0.046 Uiso 1 1 calc R . . . .
H76B H 0.492438 0.096042 0.096197 0.046 Uiso 1 1 calc R . . . .
C77 C 0.5793(2) 0.21821(18) 0.05186(17) 0.0434(6) Uani 1 1 d . . . . .
H77A H 0.639736 0.236420 0.021202 0.052 Uiso 1 1 calc R . . . .
H77B H 0.598683 0.242662 0.109237 0.052 Uiso 1 1 calc R . . . .
C78 C 0.5063(2) 0.24981(19) 0.01549(18) 0.0473(7) Uani 1 1 d . . . . .
H78A H 0.460826 0.254949 0.055823 0.057 Uiso 1 1 calc R . . . .
H78B H 0.541139 0.308629 -0.007034 0.057 Uiso 1 1 calc R . . . .
C79 C 0.4517(2) 0.17478(19) -0.05002(18) 0.0447(6) Uani 1 1 d . . . . .
H79A H 0.385649 0.172201 -0.064641 0.054 Uiso 1 1 calc R . . . .
H79B H 0.489959 0.183998 -0.098992 0.054 Uiso 1 1 calc R . . . .
C82 C 0.7895(3) 0.0633(2) 0.1041(2) 0.0597(9) Uani 1 1 d . . . . .
H82A H 0.724751 0.032215 0.072319 0.072 Uiso 1 1 calc R . . . .
H82B H 0.843600 0.081128 0.066471 0.072 Uiso 1 1 calc R . . . .
C83 C 0.8013(3) 0.0054(2) 0.1623(2) 0.0589(8) Uani 1 1 d . . . . .
H83A H 0.736121 -0.034033 0.181634 0.071 Uiso 1 1 calc R . . . .
H83B H 0.830741 -0.033250 0.136884 0.071 Uiso 1 1 calc R . . . .
C81 C 0.7946(3) 0.1444(3) 0.1567(2) 0.0694(10) Uani 1 1 d . . . . .
H81A H 0.730353 0.132417 0.180183 0.083 Uiso 1 1 calc R . . . .
H81B H 0.815429 0.198651 0.126656 0.083 Uiso 1 1 calc R . . . .
C80 C 0.8744(3) 0.1540(3) 0.2214(3) 0.0798(13) Uani 1 1 d . . . . .
H80A H 0.941342 0.193923 0.205345 0.096 Uiso 1 1 calc R . . . .
H80B H 0.863221 0.179898 0.273885 0.096 Uiso 1 1 calc R . . . .
C0AA C 0.4036(2) 0.1946(2) 0.6900(2) 0.0519(8) Uani 1 1 d . . . . .
H0AA H 0.436958 0.260116 0.683429 0.062 Uiso 1 1 calc R . . . .
H0AB H 0.413824 0.186054 0.747347 0.062 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn2 N4 2.2818(17) . ?
Mn2 N6 2.3712(17) . ?
Mn2 N5 2.2281(15) . ?
Mn2 C32 2.452(2) . ?
Mn2 C26 2.344(2) . ?
Mn2 C31 2.468(2) . ?
N4 C40 1.348(2) . ?
N4 C36 1.340(3) . ?
N6 C46 1.352(2) . ?
N6 C50 1.338(2) . ?
N5 C41 1.340(2) . ?
N5 C45 1.347(2) . ?
C46 C45 1.476(3) . ?
C46 C47 1.394(3) . ?
C41 C40 1.481(3) . ?
C41 C42 1.398(3) . ?
C45 C44 1.391(3) . ?
C37 C36 1.380(3) . ?
C37 C38 1.381(3) . ?
C50 C49 1.385(3) . ?
C40 C39 1.391(3) . ?
C48 C47 1.386(3) . ?
C48 C49 1.384(3) . ?
C27 C26 1.411(3) . ?
C27 C28 1.394(3) . ?
C44 C43 1.382(3) . ?
C32 C31 1.418(3) . ?
C32 C33 1.406(3) . ?
C26 C30 1.419(3) . ?
C42 C43 1.379(3) . ?
C39 C38 1.381(3) . ?
C28 C29 1.398(3) . ?
C31 C35 1.407(3) . ?
C35 C34 1.398(4) . ?
C30 C29 1.394(4) . ?
C33 C34 1.397(4) . ?
Mn3 N8 2.2428(16) . ?
Mn3 N7 2.2392(18) . ?
Mn3 N9 2.3571(18) . ?
Mn3 C57 2.560(2) . ?
Mn3 C51 2.361(2) . ?
Mn3 C56 2.407(2) . ?
Mn3 C55 2.520(2) . ?
N8 C70 1.344(2) . ?
N8 C66 1.344(2) . ?
C70 C69 1.391(3) . ?
C70 C71 1.489(3) . ?
C66 C65 1.487(3) . ?
C66 C67 1.392(3) . ?
N7 C65 1.344(3) . ?
N7 C61 1.342(3) . ?
C65 C64 1.387(3) . ?
N9 C71 1.340(3) . ?
N9 C75 1.344(3) . ?
C69 C68 1.385(3) . ?
C57 C56 1.422(3) . ?
C57 C58 1.403(3) . ?
C68 C67 1.383(3) . ?
C71 C72 1.396(3) . ?
C51 C55 1.430(3) . ?
C51 C52 1.410(3) . ?
C56 C60 1.401(3) . ?
C55 C54 1.395(3) . ?
C64 C63 1.393(3) . ?
C54 C53 1.403(3) . ?
C58 C59 1.404(3) . ?
C61 C62 1.382(3) . ?
C52 C53 1.403(3) . ?
C63 C62 1.377(3) . ?
C72 C73 1.385(3) . ?
C75 C74 1.380(3) . ?
C59 C60 1.403(3) . ?
C74 C73 1.380(3) . ?
Mn1 N3 2.3547(17) . ?
Mn1 N1 2.2382(16) . ?
Mn1 N2 2.2361(16) . ?
Mn1 C1 2.337(2) . ?
Mn1 C6 2.381(3) . ?
Mn1 C7 2.638(3) . ?
N3 C21 1.351(3) . ?
N3 C25 1.341(2) . ?
N1 C15 1.349(2) . ?
N1 C11 1.344(2) . ?
C15 C16 1.484(3) . ?
C15 C14 1.390(2) . ?
N2 C16 1.345(2) . ?
N2 C20 1.345(2) . ?
C16 C17 1.393(3) . ?
C14 C13 1.386(3) . ?
C13 C12 1.381(3) . ?
C17 C18 1.384(3) . ?
C19 C20 1.393(3) . ?
C19 C18 1.390(3) . ?
C22 C21 1.392(3) . ?
C22 C23 1.390(3) . ?
C21 C20 1.484(3) . ?
C12 C11 1.380(3) . ?
C25 C24 1.388(3) . ?
C24 C23 1.381(3) . ?
C3 C2 1.401(3) . ?
C3 C4 1.395(3) . ?
C2 C1 1.419(3) . ?
C1 C5 1.418(3) . ?
C5 C4 1.401(3) . ?
C9 C10 1.368(4) . ?
C9 C8 1.403(4) . ?
C10 C6 1.421(5) . ?
C8 C7 1.372(5) . ?
C6 C7 1.384(6) . ?
O3 C84 1.424(3) . ?
O3 C0AA 1.405(4) . ?
C85 C86 1.531(4) . ?
C85 C84 1.514(3) . ?
C86 C0AA 1.523(4) . ?
O1 C76 1.434(3) . ?
O1 C79 1.428(3) . ?
O2 C83 1.418(4) . ?
O2 C80 1.436(4) . ?
C76 C77 1.513(4) . ?
C77 C78 1.520(4) . ?
C78 C79 1.501(4) . ?
C82 C83 1.463(5) . ?
C82 C81 1.509(5) . ?
C81 C80 1.528(5) . ?

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
N4 Mn2 N6 140.62(6) . . ?
N4 Mn2 C32 122.14(7) . . ?
N4 Mn2 C26 107.41(7) . . ?
N4 Mn2 C31 89.04(7) . . ?
N6 Mn2 C32 90.00(7) . . ?
N6 Mn2 C31 122.37(7) . . ?
N5 Mn2 N4 72.01(6) . . ?
N5 Mn2 N6 70.03(6) . . ?
N5 Mn2 C32 127.92(7) . . ?
N5 Mn2 C26 131.96(7) . . ?
N5 Mn2 C31 126.83(7) . . ?
C32 Mn2 C31 33.50(8) . . ?
C26 Mn2 N6 90.55(7) . . ?
C26 Mn2 C32 94.10(8) . . ?
C26 Mn2 C31 100.88(7) . . ?
C40 N4 Mn2 117.07(13) . . ?
C36 N4 Mn2 124.66(13) . . ?
C36 N4 C40 118.03(17) . . ?
C46 N6 Mn2 115.64(12) . . ?
C50 N6 Mn2 124.91(13) . . ?
C50 N6 C46 117.85(17) . . ?
C41 N5 Mn2 119.08(12) . . ?
C41 N5 C45 119.73(16) . . ?
C45 N5 Mn2 121.10(12) . . ?
N6 C46 C45 115.21(16) . . ?
N6 C46 C47 122.14(18) . . ?
C47 C46 C45 122.64(17) . . ?
N5 C41 C40 115.97(16) . . ?
N5 C41 C42 121.29(18) . . ?
C42 C41 C40 122.74(18) . . ?
N5 C45 C46 115.81(16) . . ?
N5 C45 C44 121.76(18) . . ?
C44 C45 C46 122.42(18) . . ?
C36 C37 C38 118.1(2) . . ?
N6 C50 C49 123.57(18) . . ?
N4 C40 C41 115.67(17) . . ?
N4 C40 C39 121.84(18) . . ?
C39 C40 C41 122.48(17) . . ?
C49 C48 C47 119.24(19) . . ?
C48 C47 C46 118.88(18) . . ?
C28 C27 C26 108.0(2) . . ?
C43 C44 C45 118.42(19) . . ?
C31 C32 Mn2 73.87(12) . . ?
C33 C32 Mn2 86.46(14) . . ?
C33 C32 C31 107.6(2) . . ?
C27 C26 Mn2 94.85(12) . . ?
C27 C26 C30 107.4(2) . . ?
C30 C26 Mn2 95.77(13) . . ?
C43 C42 C41 118.75(19) . . ?
C38 C39 C40 118.99(19) . . ?
N4 C36 C37 123.49(19) . . ?
C42 C43 C44 120.03(18) . . ?
C27 C28 C29 108.4(2) . . ?
C48 C49 C50 118.31(19) . . ?
C37 C38 C39 119.5(2) . . ?
C32 C31 Mn2 72.63(12) . . ?
C35 C31 Mn2 86.61(13) . . ?
C35 C31 C32 107.6(2) . . ?
C34 C35 C31 108.1(2) . . ?
C29 C30 C26 107.7(2) . . ?
C30 C29 C28 108.5(2) . . ?
C34 C33 C32 108.1(2) . . ?
C33 C34 C35 108.6(2) . . ?
N8 Mn3 N9 70.25(6) . . ?
N8 Mn3 C57 89.84(7) . . ?
N8 Mn3 C51 128.54(7) . . ?
N8 Mn3 C56 120.89(7) . . ?
N8 Mn3 C55 94.86(6) . . ?
N7 Mn3 N8 72.13(6) . . ?
N7 Mn3 N9 142.11(6) . . ?
N7 Mn3 C57 100.71(7) . . ?
N7 Mn3 C51 110.39(7) . . ?
N7 Mn3 C56 118.81(7) . . ?
N7 Mn3 C55 99.33(7) . . ?
N9 Mn3 C57 83.62(7) . . ?
N9 Mn3 C51 89.88(7) . . ?
N9 Mn3 C56 85.02(7) . . ?
N9 Mn3 C55 79.64(7) . . ?
C51 Mn3 C57 135.97(8) . . ?
C51 Mn3 C56 103.06(8) . . ?
C51 Mn3 C55 33.87(7) . . ?
C56 Mn3 C57 33.10(8) . . ?
C56 Mn3 C55 133.19(8) . . ?
C55 Mn3 C57 159.90(7) . . ?
C70 N8 Mn3 121.47(13) . . ?
C66 N8 Mn3 118.65(13) . . ?
C66 N8 C70 119.87(16) . . ?
N8 C70 C69 121.76(17) . . ?
N8 C70 C71 115.01(16) . . ?
C69 C70 C71 123.19(17) . . ?
N8 C66 C65 115.03(17) . . ?
N8 C66 C67 121.28(17) . . ?
C67 C66 C65 123.68(17) . . ?
C65 N7 Mn3 118.35(13) . . ?
C61 N7 Mn3 123.02(15) . . ?
C61 N7 C65 118.55(18) . . ?
N7 C65 C66 115.67(17) . . ?
N7 C65 C64 122.09(19) . . ?
C64 C65 C66 122.24(19) . . ?
C71 N9 Mn3 117.03(13) . . ?
C71 N9 C75 118.37(18) . . ?
C75 N9 Mn3 124.50(14) . . ?
C68 C69 C70 118.29(18) . . ?
C56 C57 Mn3 67.50(12) . . ?
C58 C57 Mn3 92.61(13) . . ?
C58 C57 C56 107.6(2) . . ?
C67 C68 C69 120.04(18) . . ?
N9 C71 C70 116.12(17) . . ?
N9 C71 C72 121.57(19) . . ?
C72 C71 C70 122.27(18) . . ?
C68 C67 C66 118.73(18) . . ?
C55 C51 Mn3 79.18(12) . . ?
C52 C51 Mn3 99.28(15) . . ?
C52 C51 C55 106.7(2) . . ?
C57 C56 Mn3 79.40(13) . . ?
C60 C56 Mn3 89.40(14) . . ?
C60 C56 C57 107.8(2) . . ?
C51 C55 Mn3 66.95(11) . . ?
C54 C55 Mn3 101.71(14) . . ?
C54 C55 C51 108.40(19) . . ?
C65 C64 C63 118.9(2) . . ?
C55 C54 C53 108.02(19) . . ?
C57 C58 C59 108.1(2) . . ?
N7 C61 C62 122.4(2) . . ?
C53 C52 C51 108.32(19) . . ?
C62 C63 C64 118.7(2) . . ?
C54 C53 C52 108.5(2) . . ?
C73 C72 C71 119.2(2) . . ?
N9 C75 C74 123.4(2) . . ?
C60 C59 C58 108.3(2) . . ?
C63 C62 C61 119.3(2) . . ?
C73 C74 C75 118.2(2) . . ?
C56 C60 C59 108.1(2) . . ?
C74 C73 C72 119.2(2) . . ?
N3 Mn1 C6 84.76(10) . . ?
N3 Mn1 C7 110.52(11) . . ?
N1 Mn1 N3 141.85(6) . . ?
N1 Mn1 C1 108.45(7) . . ?
N1 Mn1 C6 115.60(9) . . ?
N1 Mn1 C7 101.19(11) . . ?
N2 Mn1 N3 70.03(6) . . ?
N2 Mn1 N1 72.33(6) . . ?
N2 Mn1 C1 132.57(7) . . ?
N2 Mn1 C6 112.36(12) . . ?
N2 Mn1 C7 137.47(8) . . ?
C1 Mn1 N3 92.69(7) . . ?
C1 Mn1 C6 109.35(11) . . ?
C1 Mn1 C7 89.78(9) . . ?
C6 Mn1 C7 31.48(13) . . ?
C21 N3 Mn1 117.24(12) . . ?
C25 N3 Mn1 124.80(14) . . ?
C25 N3 C21 117.63(17) . . ?
C15 N1 Mn1 118.09(12) . . ?
C11 N1 Mn1 123.14(13) . . ?
C11 N1 C15 118.07(16) . . ?
N1 C15 C16 115.33(15) . . ?
N1 C15 C14 122.28(17) . . ?
C14 C15 C16 122.38(17) . . ?
C16 N2 Mn1 118.40(12) . . ?
C16 N2 C20 119.85(16) . . ?
C20 N2 Mn1 121.73(12) . . ?
N2 C16 C15 115.43(16) . . ?
N2 C16 C17 121.54(17) . . ?
C17 C16 C15 123.03(16) . . ?
C13 C14 C15 118.65(18) . . ?
C12 C13 C14 119.25(18) . . ?
C18 C17 C16 118.57(18) . . ?
C18 C19 C20 118.29(18) . . ?
C23 C22 C21 118.55(19) . . ?
N3 C21 C22 122.53(17) . . ?
N3 C21 C20 115.21(16) . . ?
C22 C21 C20 122.26(17) . . ?
N2 C20 C19 121.66(17) . . ?
N2 C20 C21 115.33(16) . . ?
C19 C20 C21 123.00(17) . . ?
C11 C12 C13 118.85(18) . . ?
N3 C25 C24 123.57(19) . . ?
N1 C11 C12 122.86(18) . . ?
C23 C24 C25 118.24(18) . . ?
C24 C23 C22 119.46(18) . . ?
C4 C3 C2 108.2(2) . . ?
C3 C2 C1 108.07(19) . . ?
C2 C1 Mn1 85.69(12) . . ?
C5 C1 Mn1 99.26(14) . . ?
C5 C1 C2 107.23(19) . . ?
C4 C5 C1 107.7(2) . . ?
C17 C18 C19 120.08(19) . . ?
C3 C4 C5 108.81(19) . . ?
C10 C9 C8 109.4(3) . . ?
C9 C10 C6 106.8(3) . . ?
C7 C8 C9 107.2(3) . . ?
C10 C6 Mn1 86.73(16) . . ?
C7 C6 Mn1 84.6(2) . . ?
C7 C6 C10 107.6(3) . . ?
C8 C7 Mn1 94.38(18) . . ?
C8 C7 C6 109.0(3) . . ?
C6 C7 Mn1 63.96(17) . . ?
C0AA O3 C84 106.5(2) . . ?
C84 C85 C86 104.0(2) . . ?
C0AA C86 C85 103.8(2) . . ?
O3 C84 C85 105.6(2) . . ?
C79 O1 C76 108.2(2) . . ?
C83 O2 C80 109.2(2) . . ?
O1 C76 C77 107.5(2) . . ?
C76 C77 C78 102.6(2) . . ?
C79 C78 C77 101.4(2) . . ?
O1 C79 C78 105.8(2) . . ?
C83 C82 C81 103.5(3) . . ?
O2 C83 C82 106.6(3) . . ?
C82 C81 C80 100.2(3) . . ?
O2 C80 C81 105.7(3) . . ?
O3 C0AA C86 107.2(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_lacy1_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1822543'
_audit_update_record             
;
2018-02-06 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H26 Mn N2'
_chemical_formula_weight         517.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           114
_space_group_name_H-M_alt        'P -4 21 c'
_space_group_name_Hall           'P -4 2n'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   12.1372(7)
_cell_length_b                   12.1372(7)
_cell_length_c                   21.6505(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3189.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9832
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      30.33

_exptl_crystal_description       Block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.078
_exptl_crystal_F_000             1076
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.435
_shelx_estimated_absorpt_T_min   0.845
_shelx_estimated_absorpt_T_max   0.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6979
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            83057
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.521
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4117
_reflns_number_gt                3680
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 Structure factors included contributions from the .fab file. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0745P)²+0.3382P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1505 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.015(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4117
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn Mn 0.0000 0.5000 0.26136(2) 0.03376(14) Uani 1 2 d S T P . .
N1 N -0.08894(15) 0.43401(14) 0.17932(9) 0.0320(4) Uani 1 1 d . . . . .
C1 C -0.1777(2) 0.3696(2) 0.17971(10) 0.0399(4) Uani 1 1 d . . . . .
H1 H -0.2054 0.3462 0.2181 0.048 Uiso 1 1 calc R U . . .
C2 C -0.23196(19) 0.33468(19) 0.12624(10) 0.0417(5) Uani 1 1 d . . . . .
H2 H -0.2945 0.2893 0.1291 0.050 Uiso 1 1 calc R U . . .
C3 C -0.19310(18) 0.36724(19) 0.06905(10) 0.0378(4) Uani 1 1 d . . . . .
C4 C -0.09579(17) 0.43281(18) 0.06749(10) 0.0336(4) Uani 1 1 d . . . . .
C5 C -0.04775(15) 0.46496(16) 0.12359(10) 0.0291(4) Uani 1 1 d . . . . .
C6 C -0.25086(17) 0.33689(19) 0.01109(10) 0.0418(5) Uani 1 1 d . . . . .
C7 C -0.2567(2) 0.2281(3) -0.00793(17) 0.0581(7) Uani 1 1 d . . . . .
H7 H -0.2264 0.1720 0.0167 0.070 Uiso 1 1 calc R U . . .
C8 C -0.3078(3) 0.2022(3) -0.0640(2) 0.0717(10) Uani 1 1 d . . . . .
H8 H -0.3103 0.1285 -0.0773 0.086 Uiso 1 1 calc R U . . .
C9 C -0.3539(2) 0.2823(3) -0.09946(13) 0.0682(9) Uani 1 1 d . . . . .
H9 H -0.3874 0.2638 -0.1372 0.082 Uiso 1 1 calc R U . . .
C10 C -0.3518(2) 0.3900(3) -0.08033(12) 0.0599(7) Uani 1 1 d . . . . .
H10 H -0.3855 0.4450 -0.1043 0.072 Uiso 1 1 calc R U . . .
C11 C -0.2992(2) 0.4177(2) -0.02494(10) 0.0498(6) Uani 1 1 d . . . . .
H11 H -0.2966 0.4916 -0.0121 0.060 Uiso 1 1 calc R U . . .
C12 C -0.04535(18) 0.4679(2) 0.01074(11) 0.0446(6) Uani 1 1 d . . . . .
H12 H -0.0762 0.4458 -0.0271 0.053 Uiso 1 1 calc R U . . .
C13 C 0.1376(4) 0.4211(3) 0.33013(18) 0.0774(10) Uani 1 1 d . . . . .
H13 H 0.1627 0.4759 0.3573 0.093 Uiso 1 1 calc R U . . .
C14 C 0.0425(3) 0.3575(3) 0.33678(17) 0.0764(10) Uani 1 1 d . . . . .
H14 H -0.0081 0.3618 0.3696 0.092 Uiso 1 1 calc R U . . .
C15 C 0.0357(3) 0.2876(3) 0.28716(16) 0.0696(9) Uani 1 1 d . . . . .
H15 H -0.0203 0.2355 0.2803 0.084 Uiso 1 1 calc R U . . .
C16 C 0.1251(3) 0.3066(3) 0.24883(15) 0.0659(8) Uani 1 1 d . . . . .
H16 H 0.1394 0.2701 0.2114 0.079 Uiso 1 1 calc R U . . .
C17 C 0.1891(3) 0.3871(3) 0.27460(15) 0.0682(9) Uani 1 1 d . . . . .
H17 H 0.2554 0.4149 0.2584 0.082 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn N1 2.2273(19) . ?
Mn N1 2.2273(19) 2_565 ?
Mn C14 2.434(3) . ?
Mn C14 2.434(3) 2_565 ?
Mn C13 2.434(3) 2_565 ?
Mn C13 2.434(3) . ?
N1 C1 1.331(3) . ?
N1 C5 1.359(3) . ?
C1 C2 1.398(3) . ?
C1 H1 0.9400 . ?
C2 C3 1.383(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.425(3) . ?
C3 C6 1.484(3) . ?
C4 C5 1.403(3) . ?
C4 C12 1.438(3) . ?
C5 C5 1.438(4) 2_565 ?
C6 C11 1.383(3) . ?
C6 C7 1.384(4) . ?
C7 C8 1.399(4) . ?
C7 H7 0.9400 . ?
C8 C9 1.360(6) . ?
C8 H8 0.9400 . ?
C9 C10 1.371(5) . ?
C9 H9 0.9400 . ?
C10 C11 1.400(3) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?
C12 C12 1.348(5) 2_565 ?
C12 H12 0.9400 . ?
C13 C14 1.396(7) . ?
C13 C17 1.416(5) . ?
C13 H13 0.9400 . ?
C14 C15 1.371(5) . ?
C14 H14 0.9400 . ?
C15 C16 1.385(5) . ?
C15 H15 0.9400 . ?
C16 C17 1.368(6) . ?
C16 H16 0.9400 . ?
C17 H17 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
N1 Mn N1 74.24(9) . 2_565 ?
N1 Mn C14 112.46(12) . . ?
N1 Mn C14 133.47(9) 2_565 . ?
N1 Mn C14 133.46(9) . 2_565 ?
N1 Mn C14 112.46(12) 2_565 2_565 ?
C14 Mn C14 95.73(19) . 2_565 ?
N1 Mn C13 107.27(12) . 2_565 ?
N1 Mn C13 132.75(10) 2_565 2_565 ?
C14 Mn C13 90.84(12) . 2_565 ?
C14 Mn C13 33.34(16) 2_565 2_565 ?
N1 Mn C13 132.75(10) . . ?
N1 Mn C13 107.27(12) 2_565 . ?
C14 Mn C13 33.34(16) . . ?
C14 Mn C13 90.84(12) 2_565 . ?
C13 Mn C13 104.6(2) 2_565 . ?
C1 N1 C5 117.75(19) . . ?
C1 N1 Mn 126.75(15) . . ?
C5 N1 Mn 115.49(13) . . ?
N1 C1 C2 123.7(2) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C3 C2 C1 119.62(19) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 117.63(19) . . ?
C2 C3 C6 121.68(18) . . ?
C4 C3 C6 120.69(19) . . ?
C5 C4 C3 118.66(19) . . ?
C5 C4 C12 118.73(18) . . ?
C3 C4 C12 122.6(2) . . ?
N1 C5 C4 122.62(18) . . ?
N1 C5 C5 117.39(11) . 2_565 ?
C4 C5 C5 119.98(12) . 2_565 ?
C11 C6 C7 119.1(2) . . ?
C11 C6 C3 120.1(2) . . ?
C7 C6 C3 120.8(2) . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 119.8(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C6 C11 C10 120.4(3) . . ?
C6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C12 C12 C4 121.26(13) 2_565 . ?
C12 C12 H12 119.4 2_565 . ?
C4 C12 H12 119.4 . . ?
C14 C13 C17 107.0(4) . . ?
C14 C13 Mn 73.33(19) . . ?
C17 C13 Mn 84.15(19) . . ?
C14 C13 H13 126.5 . . ?
C17 C13 H13 126.5 . . ?
Mn C13 H13 109.1 . . ?
C15 C14 C13 108.1(3) . . ?
C15 C14 Mn 84.34(19) . . ?
C13 C14 Mn 73.33(17) . . ?
C15 C14 H14 126.0 . . ?
C13 C14 H14 126.0 . . ?
Mn C14 H14 109.2 . . ?
C14 C15 C16 108.6(4) . . ?
C14 C15 H15 125.7 . . ?
C16 C15 H15 125.7 . . ?
C17 C16 C15 108.6(3) . . ?
C17 C16 H16 125.7 . . ?
C15 C16 H16 125.7 . . ?
C16 C17 C13 107.7(3) . . ?
C16 C17 H17 126.2 . . ?
C13 C17 H17 126.2 . . ?

_refine_diff_density_max         0.632
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.049



####################################################################### 
# 
# 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_lac14_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1822545'
_audit_update_record             
;
2018-02-06 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2018-01-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 Mn N2'
_chemical_formula_sum            'C24 H22 Mn N2'
_chemical_formula_weight         393.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.0321(7)
_cell_length_b                   23.6980(9)
_cell_length_c                   13.6298(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.457(2)
_cell_angle_gamma                90
_cell_volume                     5727.6(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      26.79
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.839
_exptl_absorpt_coefficient_mu    0.468
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    0.912
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            51305
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         1.148
_diffrn_ambient_temperature      223.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7525
_reflns_number_total             10129
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         10129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²+0.1831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0969
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C6(H6), C5(H5), C3(H3), C2(H2), C20(H20), C24(H24), C23(H23),
 C22(H22), C21(H21), C17(H17), C16(H16), C15(H15), C19(H19), C18(H18), C33(H33),
  C32(H32), C30(H30), C29(H29), C27(H27), C26(H26), C39(H39), C43(H43),
 C42(H42), C41(H41), C40(H40), C46(H46), C45(H45), C44(H44), C48(H48), C47(H47)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C38(H38A,H38B,H38C), C37(H37A,H37B,
 H37C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.35246(2) 0.37530(2) 0.27986(2) 0.04003(9) Uani 1 1 d . . . . .
N1 N 0.42865(8) 0.37558(6) 0.42959(11) 0.0431(4) Uani 1 1 d . . . . .
N2 N 0.44176(8) 0.44000(6) 0.26709(11) 0.0407(4) Uani 1 1 d . . . . .
C14 C 0.35606(13) 0.30538(10) 0.50169(18) 0.0751(7) Uani 1 1 d . . . . .
H14A H 0.320214 0.320005 0.540442 0.113 Uiso 1 1 calc GR . . . .
H14B H 0.373988 0.268742 0.527521 0.113 Uiso 1 1 calc GR . . . .
H14C H 0.331681 0.301622 0.432461 0.113 Uiso 1 1 calc GR . . . .
C10 C 0.42090(11) 0.34487(9) 0.50880(15) 0.0555(5) Uani 1 1 d . . . . .
C9 C 0.47380(15) 0.34862(12) 0.59862(16) 0.0746(7) Uani 1 1 d . . . . .
H9 H 0.467836 0.326274 0.653633 0.090 Uiso 1 1 calc R . . . .
C8 C 0.53290(15) 0.38421(12) 0.60563(17) 0.0791(8) Uani 1 1 d . . . . .
H8 H 0.567823 0.386637 0.665728 0.095 Uiso 1 1 calc R . . . .
C7 C 0.54262(12) 0.41740(10) 0.52457(15) 0.0596(6) Uani 1 1 d . . . . .
C6 C 0.60385(13) 0.45569(12) 0.5270(2) 0.0764(7) Uani 1 1 d . . . . .
H6 H 0.639439 0.459828 0.586177 0.092 Uiso 1 1 calc R . . . .
C5 C 0.61153(13) 0.48591(10) 0.4463(2) 0.0738(7) Uani 1 1 d . . . . .
H5 H 0.652675 0.510615 0.449437 0.089 Uiso 1 1 calc R . . . .
C4 C 0.55842(11) 0.48111(8) 0.35613(16) 0.0542(5) Uani 1 1 d . . . . .
C3 C 0.56443(14) 0.51158(9) 0.26941(19) 0.0691(7) Uani 1 1 d . . . . .
H3 H 0.605631 0.535823 0.269012 0.083 Uiso 1 1 calc R . . . .
C2 C 0.51134(13) 0.50604(9) 0.18727(18) 0.0659(6) Uani 1 1 d . . . . .
H2 H 0.515801 0.526186 0.129216 0.079 Uiso 1 1 calc R . . . .
C1 C 0.44935(11) 0.47049(8) 0.18725(15) 0.0510(5) Uani 1 1 d . . . . .
C13 C 0.38996(13) 0.46632(10) 0.09580(16) 0.0715(7) Uani 1 1 d . . . . .
H13A H 0.350509 0.440909 0.108228 0.107 Uiso 1 1 calc GR . . . .
H13B H 0.412072 0.451939 0.041014 0.107 Uiso 1 1 calc GR . . . .
H13C H 0.368669 0.503387 0.078717 0.107 Uiso 1 1 calc GR . . . .
C12 C 0.49602(10) 0.44483(7) 0.35077(13) 0.0426(4) Uani 1 1 d . . . . .
C11 C 0.48830(10) 0.41163(8) 0.43668(13) 0.0443(5) Uani 1 1 d . . . . .
C20 C 0.33601(13) 0.28098(9) 0.21822(19) 0.0652(6) Uani 1 1 d . . . . .
H20 H 0.288685 0.270091 0.231495 0.078 Uiso 1 1 calc R . . . .
C24 C 0.34860(15) 0.31648(10) 0.14132(19) 0.0718(7) Uani 1 1 d . . . . .
H24 H 0.311515 0.333730 0.093315 0.086 Uiso 1 1 calc R . . . .
C23 C 0.42567(18) 0.32156(11) 0.1488(2) 0.0871(8) Uani 1 1 d . . . . .
H23 H 0.450479 0.342866 0.106399 0.105 Uiso 1 1 calc R . . . .
C22 C 0.45961(14) 0.29031(12) 0.2285(3) 0.0900(9) Uani 1 1 d . . . . .
H22 H 0.511880 0.286773 0.250747 0.108 Uiso 1 1 calc R . . . .
C21 C 0.40442(16) 0.26483(10) 0.2708(2) 0.0777(7) Uani 1 1 d . . . . .
H21 H 0.412481 0.240549 0.326273 0.093 Uiso 1 1 calc R . . . .
C17 C 0.25663(11) 0.44846(9) 0.27491(17) 0.0597(6) Uani 1 1 d . . . . .
H17 H 0.283155 0.482778 0.279284 0.072 Uiso 1 1 calc R . . . .
C16 C 0.24906(11) 0.41341(10) 0.35469(16) 0.0576(6) Uani 1 1 d . . . . .
H16 H 0.269215 0.419943 0.422300 0.069 Uiso 1 1 calc R . . . .
C15 C 0.20608(11) 0.36684(9) 0.31586(16) 0.0560(5) Uani 1 1 d . . . . .
H15 H 0.192412 0.336176 0.352545 0.067 Uiso 1 1 calc R . . . .
C19 C 0.18722(12) 0.37401(9) 0.21344(17) 0.0567(6) Uani 1 1 d . . . . .
H19 H 0.158088 0.349019 0.168611 0.068 Uiso 1 1 calc R . . . .
C18 C 0.21835(12) 0.42397(9) 0.18825(16) 0.0577(6) Uani 1 1 d . . . . .
H18 H 0.214243 0.438774 0.123500 0.069 Uiso 1 1 calc R . . . .
Mn2 Mn 0.15336(2) 0.11271(2) 0.27282(2) 0.03913(9) Uani 1 1 d . . . . .
N3 N 0.08022(8) 0.12584(6) 0.12224(10) 0.0361(3) Uani 1 1 d . . . . .
N4 N 0.06227(8) 0.04673(6) 0.26381(11) 0.0409(4) Uani 1 1 d . . . . .
C38 C 0.10842(14) 0.00712(10) 0.42879(16) 0.0756(7) Uani 1 1 d . . . . .
H38A H 0.131668 -0.029890 0.437538 0.113 Uiso 1 1 calc GR . . . .
H38B H 0.082513 0.014829 0.483796 0.113 Uiso 1 1 calc GR . . . .
H38C H 0.147003 0.035472 0.427320 0.113 Uiso 1 1 calc GR . . . .
C34 C 0.05299(12) 0.00857(8) 0.33266(15) 0.0520(5) Uani 1 1 d . . . . .
C33 C -0.00658(13) -0.03026(9) 0.31599(18) 0.0642(6) Uani 1 1 d . . . . .
H33 H -0.012064 -0.056469 0.365949 0.077 Uiso 1 1 calc R . . . .
C32 C -0.05621(13) -0.03042(9) 0.22887(18) 0.0642(6) Uani 1 1 d . . . . .
H32 H -0.096115 -0.056523 0.218346 0.077 Uiso 1 1 calc R . . . .
C31 C -0.04793(11) 0.00845(8) 0.15442(16) 0.0510(5) Uani 1 1 d . . . . .
C30 C -0.09714(13) 0.00990(10) 0.06045(19) 0.0675(6) Uani 1 1 d . . . . .
H30 H -0.136867 -0.016261 0.046841 0.081 Uiso 1 1 calc R . . . .
C29 C -0.08799(12) 0.04775(10) -0.00894(17) 0.0642(6) Uani 1 1 d . . . . .
H29 H -0.121154 0.047719 -0.070703 0.077 Uiso 1 1 calc R . . . .
C28 C -0.02845(11) 0.08831(9) 0.00946(14) 0.0501(5) Uani 1 1 d . . . . .
C27 C -0.01701(13) 0.12831(10) -0.06136(15) 0.0617(6) Uani 1 1 d . . . . .
H27 H -0.049450 0.129573 -0.123652 0.074 Uiso 1 1 calc R . . . .
C26 C 0.04079(12) 0.16525(9) -0.04027(15) 0.0582(6) Uani 1 1 d . . . . .
H26 H 0.048574 0.192165 -0.088045 0.070 Uiso 1 1 calc R . . . .
C25 C 0.08935(10) 0.16354(8) 0.05297(13) 0.0438(4) Uani 1 1 d . . . . .
C37 C 0.15291(11) 0.20490(9) 0.07429(16) 0.0569(5) Uani 1 1 d . . . . .
H37A H 0.174940 0.203618 0.144678 0.085 Uiso 1 1 calc GR . . . .
H37B H 0.134020 0.242596 0.056884 0.085 Uiso 1 1 calc GR . . . .
H37C H 0.190975 0.195311 0.035116 0.085 Uiso 1 1 calc GR . . . .
C36 C 0.02190(10) 0.08838(7) 0.10117(13) 0.0386(4) Uani 1 1 d . . . . .
C35 C 0.01253(10) 0.04718(7) 0.17527(13) 0.0390(4) Uani 1 1 d . . . . .
C39 C 0.23782(14) 0.02967(12) 0.2393(3) 0.0959(10) Uani 1 1 d . . . . .
H39 H 0.212137 -0.004193 0.220037 0.115 Uiso 1 1 calc R . . . .
C43 C 0.24834(14) 0.07566(14) 0.17588(19) 0.0850(9) Uani 1 1 d . . . . .
H43 H 0.231556 0.078169 0.106576 0.102 Uiso 1 1 calc R . . . .
C42 C 0.28837(14) 0.11582(10) 0.2375(2) 0.0719(7) Uani 1 1 d . . . . .
H42 H 0.302992 0.151428 0.217274 0.086 Uiso 1 1 calc R . . . .
C41 C 0.30302(16) 0.09522(14) 0.3319(2) 0.0867(8) Uani 1 1 d . . . . .
H41 H 0.330624 0.114142 0.387399 0.104 Uiso 1 1 calc R . . . .
C40 C 0.27255(16) 0.04442(15) 0.3343(2) 0.0924(9) Uani 1 1 d . . . . .
H40 H 0.274367 0.022055 0.391632 0.111 Uiso 1 1 calc R . . . .
C46 C 0.17111(14) 0.19935(9) 0.36346(17) 0.0618(6) Uani 1 1 d . . . . .
H46 H 0.219287 0.211615 0.355729 0.074 Uiso 1 1 calc R . . . .
C45 C 0.15526(15) 0.15878(9) 0.43086(16) 0.0644(6) Uani 1 1 d . . . . .
H45 H 0.190713 0.138558 0.476677 0.077 Uiso 1 1 calc R . . . .
C44 C 0.07754(16) 0.15385(10) 0.41770(19) 0.0755(7) Uani 1 1 d . . . . .
H44 H 0.050991 0.129461 0.453344 0.091 Uiso 1 1 calc R . . . .
C48 C 0.04587(15) 0.19035(11) 0.3442(2) 0.0762(7) Uani 1 1 d . . . . .
H48 H -0.006049 0.195497 0.321059 0.091 Uiso 1 1 calc R . . . .
C47 C 0.10304(16) 0.21824(9) 0.31007(17) 0.0694(7) Uani 1 1 d . . . . .
H47 H 0.096900 0.245495 0.259125 0.083 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 N1 2.2438(15) . ?
Mn1 N2 2.2530(14) . ?
Mn1 C20 2.387(2) . ?
Mn1 C24 2.338(2) . ?
Mn1 C17 2.440(2) . ?
Mn1 C16 2.454(2) . ?
N1 C10 1.330(2) . ?
N1 C11 1.363(2) . ?
N2 C1 1.334(2) . ?
N2 C12 1.366(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C14 C10 1.487(3) . ?
C10 C9 1.412(3) . ?
C9 H9 0.9400 . ?
C9 C8 1.349(3) . ?
C8 H8 0.9400 . ?
C8 C7 1.393(3) . ?
C7 C6 1.425(3) . ?
C7 C11 1.410(3) . ?
C6 H6 0.9400 . ?
C6 C5 1.341(3) . ?
C5 H5 0.9400 . ?
C5 C4 1.419(3) . ?
C4 C3 1.406(3) . ?
C4 C12 1.407(3) . ?
C3 H3 0.9400 . ?
C3 C2 1.341(3) . ?
C2 H2 0.9400 . ?
C2 C1 1.400(3) . ?
C1 C13 1.492(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C12 C11 1.438(3) . ?
C20 H20 0.9400 . ?
C20 C24 1.394(3) . ?
C20 C21 1.364(3) . ?
C24 H24 0.9400 . ?
C24 C23 1.380(3) . ?
C23 H23 0.9400 . ?
C23 C22 1.364(4) . ?
C22 H22 0.9400 . ?
C22 C21 1.377(4) . ?
C21 H21 0.9400 . ?
C17 H17 0.9400 . ?
C17 C16 1.395(3) . ?
C17 C18 1.383(3) . ?
C16 H16 0.9400 . ?
C16 C15 1.396(3) . ?
C15 H15 0.9400 . ?
C15 C19 1.386(3) . ?
C19 H19 0.9400 . ?
C19 C18 1.380(3) . ?
C18 H18 0.9400 . ?
Mn2 N3 2.2507(14) . ?
Mn2 N4 2.2549(14) . ?
Mn2 C39 2.579(3) . ?
Mn2 C43 2.504(2) . ?
Mn2 C42 2.567(2) . ?
Mn2 C46 2.3877(19) . ?
Mn2 C45 2.410(2) . ?
N3 C25 1.332(2) . ?
N3 C36 1.366(2) . ?
N4 C34 1.335(2) . ?
N4 C35 1.367(2) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C38 H38C 0.9700 . ?
C38 C34 1.497(3) . ?
C34 C33 1.401(3) . ?
C33 H33 0.9400 . ?
C33 C32 1.351(3) . ?
C32 H32 0.9400 . ?
C32 C31 1.398(3) . ?
C31 C30 1.420(3) . ?
C31 C35 1.414(2) . ?
C30 H30 0.9400 . ?
C30 C29 1.335(3) . ?
C29 H29 0.9400 . ?
C29 C28 1.429(3) . ?
C28 C27 1.395(3) . ?
C28 C36 1.405(2) . ?
C27 H27 0.9400 . ?
C27 C26 1.352(3) . ?
C26 H26 0.9400 . ?
C26 C25 1.407(3) . ?
C25 C37 1.496(3) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 H37C 0.9700 . ?
C36 C35 1.436(2) . ?
C39 H39 0.9400 . ?
C39 C43 1.425(4) . ?
C39 C40 1.377(4) . ?
C43 H43 0.9400 . ?
C43 C42 1.382(3) . ?
C42 H42 0.9400 . ?
C42 C41 1.358(3) . ?
C41 H41 0.9400 . ?
C41 C40 1.326(4) . ?
C40 H40 0.9400 . ?
C46 H46 0.9400 . ?
C46 C45 1.395(3) . ?
C46 C47 1.383(3) . ?
C45 H45 0.9400 . ?
C45 C44 1.385(3) . ?
C44 H44 0.9400 . ?
C44 C48 1.367(3) . ?
C48 H48 0.9400 . ?
C48 C47 1.375(3) . ?
C47 H47 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
N1 Mn1 N2 74.93(5) . . ?
N1 Mn1 C20 109.84(7) . . ?
N1 Mn1 C24 131.30(7) . . ?
N1 Mn1 C17 109.67(7) . . ?
N1 Mn1 C16 90.39(6) . . ?
N2 Mn1 C20 130.92(7) . . ?
N2 Mn1 C24 105.09(8) . . ?
N2 Mn1 C17 91.54(7) . . ?
N2 Mn1 C16 112.90(7) . . ?
C20 Mn1 C17 127.83(8) . . ?
C20 Mn1 C16 115.82(8) . . ?
C24 Mn1 C20 34.31(8) . . ?
C24 Mn1 C17 118.96(8) . . ?
C24 Mn1 C16 129.91(9) . . ?
C17 Mn1 C16 33.11(7) . . ?
C10 N1 Mn1 126.83(14) . . ?
C10 N1 C11 118.88(17) . . ?
C11 N1 Mn1 114.29(12) . . ?
C1 N2 Mn1 127.76(12) . . ?
C1 N2 C12 118.15(16) . . ?
C12 N2 Mn1 113.96(11) . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
N1 C10 C14 119.24(18) . . ?
N1 C10 C9 121.0(2) . . ?
C9 C10 C14 119.7(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 H9 119.9 . . ?
C9 C8 H8 119.7 . . ?
C9 C8 C7 120.6(2) . . ?
C7 C8 H8 119.7 . . ?
C8 C7 C6 123.3(2) . . ?
C8 C7 C11 116.8(2) . . ?
C11 C7 C6 119.9(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 C7 121.0(2) . . ?
C5 C6 H6 119.5 . . ?
C6 C5 H5 119.5 . . ?
C6 C5 C4 120.9(2) . . ?
C4 C5 H5 119.5 . . ?
C3 C4 C5 123.0(2) . . ?
C3 C4 C12 116.94(19) . . ?
C12 C4 C5 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C3 C2 H2 119.7 . . ?
C3 C2 C1 120.5(2) . . ?
C1 C2 H2 119.7 . . ?
N2 C1 C2 121.74(19) . . ?
N2 C1 C13 118.76(17) . . ?
C2 C1 C13 119.49(19) . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C12 C4 122.63(18) . . ?
N2 C12 C11 118.26(16) . . ?
C4 C12 C11 119.11(17) . . ?
N1 C11 C7 122.59(18) . . ?
N1 C11 C12 118.48(16) . . ?
C7 C11 C12 118.93(18) . . ?
Mn1 C20 H20 104.4 . . ?
C24 C20 Mn1 70.91(12) . . ?
C24 C20 H20 126.0 . . ?
C21 C20 Mn1 92.00(14) . . ?
C21 C20 H20 126.0 . . ?
C21 C20 C24 108.0(2) . . ?
Mn1 C24 H24 102.5 . . ?
C20 C24 Mn1 74.79(13) . . ?
C20 C24 H24 126.4 . . ?
C23 C24 Mn1 90.35(15) . . ?
C23 C24 C20 107.2(2) . . ?
C23 C24 H24 126.4 . . ?
C24 C23 H23 125.9 . . ?
C22 C23 C24 108.2(3) . . ?
C22 C23 H23 125.9 . . ?
C23 C22 H22 125.7 . . ?
C23 C22 C21 108.5(2) . . ?
C21 C22 H22 125.7 . . ?
C20 C21 C22 108.1(3) . . ?
C20 C21 H21 126.0 . . ?
C22 C21 H21 126.0 . . ?
Mn1 C17 H17 105.3 . . ?
C16 C17 Mn1 74.00(12) . . ?
C16 C17 H17 125.9 . . ?
C18 C17 Mn1 88.09(13) . . ?
C18 C17 H17 125.9 . . ?
C18 C17 C16 108.2(2) . . ?
Mn1 C16 H16 106.3 . . ?
C17 C16 Mn1 72.89(12) . . ?
C17 C16 H16 126.2 . . ?
C17 C16 C15 107.53(19) . . ?
C15 C16 Mn1 87.87(13) . . ?
C15 C16 H16 126.2 . . ?
C16 C15 H15 126.2 . . ?
C19 C15 C16 107.6(2) . . ?
C19 C15 H15 126.2 . . ?
C15 C19 H19 125.7 . . ?
C18 C19 C15 108.62(19) . . ?
C18 C19 H19 125.7 . . ?
C17 C18 H18 126.0 . . ?
C19 C18 C17 108.1(2) . . ?
C19 C18 H18 126.0 . . ?
N3 Mn2 N4 75.27(5) . . ?
N3 Mn2 C39 102.19(9) . . ?
N3 Mn2 C43 84.90(7) . . ?
N3 Mn2 C42 104.09(7) . . ?
N3 Mn2 C46 110.74(7) . . ?
N3 Mn2 C45 131.56(7) . . ?
N4 Mn2 C39 84.78(7) . . ?
N4 Mn2 C43 106.82(9) . . ?
N4 Mn2 C42 135.72(7) . . ?
N4 Mn2 C46 130.72(7) . . ?
N4 Mn2 C45 104.77(7) . . ?
C43 Mn2 C39 32.52(9) . . ?
C43 Mn2 C42 31.60(8) . . ?
C42 Mn2 C39 51.54(8) . . ?
C46 Mn2 C39 136.02(9) . . ?
C46 Mn2 C43 122.28(10) . . ?
C46 Mn2 C42 91.71(8) . . ?
C46 Mn2 C45 33.80(7) . . ?
C45 Mn2 C39 126.22(10) . . ?
C45 Mn2 C43 136.92(9) . . ?
C45 Mn2 C42 107.14(9) . . ?
C25 N3 Mn2 127.73(12) . . ?
C25 N3 C36 118.45(15) . . ?
C36 N3 Mn2 113.77(11) . . ?
C34 N4 Mn2 127.89(13) . . ?
C34 N4 C35 118.69(16) . . ?
C35 N4 Mn2 113.41(11) . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C34 C38 H38A 109.5 . . ?
C34 C38 H38B 109.5 . . ?
C34 C38 H38C 109.5 . . ?
N4 C34 C38 118.80(18) . . ?
N4 C34 C33 121.39(19) . . ?
C33 C34 C38 119.81(18) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 C34 120.7(2) . . ?
C32 C33 H33 119.7 . . ?
C33 C32 H32 120.2 . . ?
C33 C32 C31 119.7(2) . . ?
C31 C32 H32 120.2 . . ?
C32 C31 C30 122.6(2) . . ?
C32 C31 C35 117.50(19) . . ?
C35 C31 C30 119.89(19) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 C31 121.2(2) . . ?
C29 C30 H30 119.4 . . ?
C30 C29 H29 119.6 . . ?
C30 C29 C28 120.9(2) . . ?
C28 C29 H29 119.6 . . ?
C27 C28 C29 122.45(19) . . ?
C27 C28 C36 117.53(18) . . ?
C36 C28 C29 120.02(19) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 C28 119.88(19) . . ?
C26 C27 H27 120.1 . . ?
C27 C26 H26 119.9 . . ?
C27 C26 C25 120.19(19) . . ?
C25 C26 H26 119.9 . . ?
N3 C25 C26 121.53(18) . . ?
N3 C25 C37 119.40(16) . . ?
C26 C25 C37 119.06(17) . . ?
C25 C37 H37A 109.5 . . ?
C25 C37 H37B 109.5 . . ?
C25 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N3 C36 C28 122.41(17) . . ?
N3 C36 C35 118.55(15) . . ?
C28 C36 C35 119.03(16) . . ?
N4 C35 C31 122.05(17) . . ?
N4 C35 C36 118.96(15) . . ?
C31 C35 C36 118.99(17) . . ?
Mn2 C39 H39 115.1 . . ?
C43 C39 Mn2 70.85(14) . . ?
C43 C39 H39 126.6 . . ?
C40 C39 Mn2 79.76(17) . . ?
C40 C39 H39 126.6 . . ?
C40 C39 C43 106.8(3) . . ?
Mn2 C43 H43 112.4 . . ?
C39 C43 Mn2 76.64(15) . . ?
C39 C43 H43 127.2 . . ?
C42 C43 Mn2 76.71(14) . . ?
C42 C43 C39 105.7(2) . . ?
C42 C43 H43 127.2 . . ?
Mn2 C42 H42 114.0 . . ?
C43 C42 Mn2 71.69(14) . . ?
C43 C42 H42 125.7 . . ?
C41 C42 Mn2 80.76(17) . . ?
C41 C42 C43 108.6(3) . . ?
C41 C42 H42 125.7 . . ?
C42 C41 H41 125.1 . . ?
C40 C41 C42 109.8(3) . . ?
C40 C41 H41 125.1 . . ?
C39 C40 H40 125.4 . . ?
C41 C40 C39 109.1(3) . . ?
C41 C40 H40 125.4 . . ?
Mn2 C46 H46 104.3 . . ?
C45 C46 Mn2 73.96(12) . . ?
C45 C46 H46 126.2 . . ?
C47 C46 Mn2 89.04(13) . . ?
C47 C46 H46 126.2 . . ?
C47 C46 C45 107.5(2) . . ?
Mn2 C45 H45 105.1 . . ?
C46 C45 Mn2 72.24(12) . . ?
C46 C45 H45 126.4 . . ?
C44 C45 Mn2 89.78(14) . . ?
C44 C45 C46 107.2(2) . . ?
C44 C45 H45 126.4 . . ?
C45 C44 H44 125.7 . . ?
C48 C44 C45 108.6(2) . . ?
C48 C44 H44 125.7 . . ?
C44 C48 H48 125.9 . . ?
C44 C48 C47 108.2(2) . . ?
C47 C48 H48 125.9 . . ?
C46 C47 H47 125.8 . . ?
C48 C47 C46 108.3(2) . . ?
C48 C47 H47 125.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
