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

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

data_CN13013
_database_code_depnum_ccdc_archive 'CCDC 1909283'
loop_
_audit_author_name
_audit_author_address
'Christoph Nagel'
;Institut fuer Anorganische Chemie Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2019-04-10 deposited with the CCDC.	2019-09-19 downloaded from the CCDC.
;
_audit_creation_date             2013-12-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_chemical_formula_moiety         '0.14(C33 H24 Mn N4 O3), 0.43(H2 O), 0.14(Br)'
_chemical_formula_sum            'C4.714 H4.286 Br0.143 Mn0.143 N0.571 O0.857'
_chemical_formula_weight         101.92
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Mn 0.34779 0.73263 11.28190 7.35730 3.01930 2.24410 5.34090 0.34320 17.86740
83.75430 1.089599967
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

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

_symmetry_Int_Tables_number      14
_cell_length_a                   16.4923(9)
_cell_length_b                   13.8229(7)
_cell_length_c                   14.3262(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.227(2)
_cell_angle_gamma                90
_cell_volume                     3064.6(3)
_cell_formula_units_Z            28
_cell_measurement_reflns_used    9886
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.63
_cell_measurement_temperature    100(2)
_exptl_absorpt_coefficient_mu    1.787
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0667 before and 0.0464 after correction.
The Ratio of minimum to maximum transmission is 0.8371.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.5463
_exptl_crystal_density_meas      .
_exptl_crystal_F_000             1456.8902
_exptl_crystal_size_max          0.775
_exptl_crystal_size_mid          0.324
_exptl_crystal_size_min          0.315
_exptl_crystal_colour_primary    yellow
_exptl_crystal_description       block
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            45659
_diffrn_reflns_theta_full        25.9997
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.32
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              19
_reflns_limit_h_min              -20
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                5031
_reflns_number_total             6030
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_refine_diff_density_max         0.4280
_refine_diff_density_min         -0.5734
_refine_diff_density_rms         0.0997
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             15.4752
_refine_ls_goodness_of_fit_ref   1.0451
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    54
_refine_ls_number_parameters     414
_refine_ls_number_reflns         6030
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0290
_refine_ls_restrained_S_all      1.0451
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0277P)²+2.6612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0685
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O4(H4c,H4d), O6(H6a,H6b), O5(H5a,H5b)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4a,H4b), C14(H14a,H14b), C24(H24a,H24b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17),
 C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C27(H27), C30(H30), C31(H31),
  C32(H32), C33(H33)
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
C1 C 0.41434(15) 0.19542(15) 0.67982(16) 0.0125(5) Uani 1.000000 .
C2 C 0.31166(13) 0.07422(16) 0.66708(15) 0.0113(4) Uani 1.000000 .
C3 C 0.27734(13) 0.25142(15) 0.69413(16) 0.0116(5) Uani 1.000000 .
C4 C 0.15443(14) 0.21985(16) 0.41459(15) 0.0125(5) Uani 1.000000 .
H4a H 0.09356(14) 0.24021(16) 0.39847(15) 0.0150(5) Uiso 1.000000 R
H4b H 0.15856(14) 0.18403(16) 0.35656(15) 0.0150(5) Uiso 1.000000 R
C14 C 0.18728(14) 0.05408(15) 0.46609(16) 0.0123(5) Uani 1.000000 .
H14a H 0.13525(14) 0.03777(15) 0.40838(16) 0.0147(5) Uiso 1.000000 R
H14b H 0.19280(14) 0.00628(15) 0.51940(16) 0.0147(5) Uiso 1.000000 R
C24 C 0.10778(14) 0.14849(16) 0.54577(17) 0.0139(5) Uani 1.000000 .
H24a H 0.12614(14) 0.10337(16) 0.60295(17) 0.0167(6) Uiso 1.000000 R
H24b H 0.05594(14) 0.12033(16) 0.49511(17) 0.0167(6) Uiso 1.000000 R
C5 C 0.21018(14) 0.30778(15) 0.43130(15) 0.0110(4) Uani 1.000000 .
C6 C 0.18249(14) 0.38225(16) 0.35948(16) 0.0138(5) Uani 1.000000 .
H6 H 0.13039(14) 0.37509(16) 0.30435(16) 0.0166(6) Uiso 1.000000 R
C7 C 0.23039(15) 0.46384(16) 0.36941(16) 0.0142(5) Uani 1.000000 .
H7 H 0.21229(15) 0.51428(16) 0.32163(16) 0.0170(6) Uiso 1.000000 R
C8 C 0.30771(14) 0.47259(16) 0.45207(16) 0.0126(5) Uani 1.000000 .
C9 C 0.33258(14) 0.39541(15) 0.52174(15) 0.0108(4) Uani 1.000000 .
C10 C 0.36010(15) 0.55628(16) 0.46639(17) 0.0176(5) Uani 1.000000 .
H10 H 0.34280(15) 0.60821(16) 0.42030(17) 0.0211(6) Uiso 1.000000 R
C11 C 0.43517(16) 0.56308(17) 0.54574(17) 0.0190(5) Uani 1.000000 .
H11 H 0.47081(16) 0.61869(17) 0.55399(17) 0.0228(6) Uiso 1.000000 R
C12 C 0.45925(15) 0.48762(16) 0.61478(16) 0.0163(5) Uani 1.000000 .
H12 H 0.51165(15) 0.49256(16) 0.66985(16) 0.0196(6) Uiso 1.000000 R
C13 C 0.40892(14) 0.40653(16) 0.60487(16) 0.0133(5) Uani 1.000000 .
H13 H 0.42563(14) 0.35752(16) 0.65437(16) 0.0160(6) Uiso 1.000000 R
C15 C 0.26593(14) 0.05065(15) 0.43630(15) 0.0120(4) Uani 1.000000 .
C16 C 0.27091(15) -0.01455(16) 0.36334(16) 0.0153(5) Uani 1.000000 .
H16 H 0.22377(15) -0.05615(16) 0.33063(16) 0.0184(6) Uiso 1.000000 R
C17 C 0.34434(15) -0.01731(16) 0.34010(16) 0.0167(5) Uani 1.000000 .
H17 H 0.34950(15) -0.06232(16) 0.29235(16) 0.0200(6) Uiso 1.000000 R
C18 C 0.41262(14) 0.04701(16) 0.38730(15) 0.0133(5) Uani 1.000000 .
C19 C 0.40195(14) 0.11485(15) 0.45685(15) 0.0113(4) Uani 1.000000 .
C20 C 0.49127(15) 0.04635(17) 0.36793(16) 0.0167(5) Uani 1.000000 .
H20 H 0.49919(15) 0.00011(17) 0.32278(16) 0.0201(6) Uiso 1.000000 R
C21 C 0.55583(15) 0.11052(17) 0.41258(17) 0.0173(5) Uani 1.000000 .
H21 H 0.60854(15) 0.10822(17) 0.39963(17) 0.0207(6) Uiso 1.000000 R
C22 C 0.54355(15) 0.18011(16) 0.47797(17) 0.0157(5) Uani 1.000000 .
H22 H 0.58801(15) 0.22566(16) 0.50827(17) 0.0188(6) Uiso 1.000000 R
C23 C 0.46825(14) 0.18334(16) 0.49878(16) 0.0134(5) Uani 1.000000 .
H23 H 0.46068(14) 0.23209(16) 0.54179(16) 0.0161(5) Uiso 1.000000 R
C25 C 0.08224(14) 0.24275(16) 0.58042(16) 0.0138(5) Uani 1.000000 .
C26 C 0.02090(14) 0.23783(18) 0.63042(16) 0.0167(5) Uani 1.000000 .
H26 H -0.00423(14) 0.17771(18) 0.63761(16) 0.0201(6) Uiso 1.000000 R
C27 C -0.00103(15) 0.32046(18) 0.66759(17) 0.0179(5) Uani 1.000000 .
H27 H -0.04106(15) 0.31830(18) 0.70190(17) 0.0215(6) Uiso 1.000000 R
C28 C 0.03607(14) 0.40964(17) 0.65491(16) 0.0150(5) Uani 1.000000 .
C29 C 0.09317(14) 0.40854(17) 0.59993(16) 0.0152(5) Uani 1.000000 .
C30 C 0.01825(15) 0.49856(18) 0.69244(17) 0.0196(5) Uani 1.000000 .
H30 H -0.01821(15) 0.49967(18) 0.73127(17) 0.0236(6) Uiso 1.000000 R
C31 C 0.05295(15) 0.58332(18) 0.67347(17) 0.0209(5) Uani 1.000000 .
H31 H 0.03972(15) 0.64276(18) 0.69826(17) 0.0251(6) Uiso 1.000000 R
C32 C 0.10834(15) 0.58233(18) 0.61711(17) 0.0197(5) Uani 1.000000 .
H32 H 0.13184(15) 0.64129(18) 0.60375(17) 0.0236(6) Uiso 1.000000 R
C33 C 0.12845(15) 0.49672(17) 0.58150(17) 0.0182(5) Uani 1.000000 .
H33 H 0.16625(15) 0.49675(17) 0.54429(17) 0.0218(6) Uiso 1.000000 R
N1 N 0.17860(11) 0.15360(13) 0.50236(13) 0.0102(4) Uani 1.000000 .
N2 N 0.28325(11) 0.31112(13) 0.50888(12) 0.0096(4) Uani 1.000000 .
N3 N 0.32822(11) 0.11308(13) 0.48258(12) 0.0098(4) Uani 1.000000 .
N4 N 0.11597(12) 0.32423(14) 0.56472(13) 0.0147(4) Uani 1.000000 .
O1 O 0.48203(10) 0.19254(12) 0.74068(12) 0.0194(4) Uani 1.000000 .
O2 O 0.32309(10) 0.00590(11) 0.71498(11) 0.0174(3) Uani 1.000000 .
O3 O 0.26781(10) 0.29071(11) 0.75991(11) 0.0175(4) Uani 1.000000 .
Mn1 Mn 0.30419(2) 0.18622(2) 0.59825(2) 0.00840(8) Uani 1.000000 .
O4 O -0.22754(13) 0.24483(14) 0.17472(13) 0.0297(4) Uani 1.000000 .
H4c H -0.1895(13) 0.2119(19) 0.2186(14) 0.0445(7) Uiso 1.000000 G
H4d H -0.2670(13) 0.262(2) 0.1969(17) 0.0445(7) Uiso 1.000000 G
Br1 Br -0.106290(15) 0.112482(18) 0.362631(17) 0.01935(7) Uani 1.000000 .
O6 O 0.67360(13) 0.21324(17) 0.79823(17) 0.0446(6) Uani 1.000000 .
H6a H 0.6196(3) 0.222(3) 0.784(2) 0.0669(9) Uiso 1.000000 G
H6b H 0.7006(15) 0.240(2) 0.8540(13) 0.0669(9) Uiso 1.000000 G
O5 O 0.23859(12) -0.19817(16) 0.52164(14) 0.0339(5) Uani 1.000000 .
H5a H 0.1938(9) -0.182(2) 0.5343(19) 0.0508(7) Uiso 1.000000 G
H5b H 0.2236(15) -0.221(2) 0.4631(9) 0.0508(7) Uiso 1.000000 G


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.155(3) .
C1 Mn1 1.793(2) .
C2 O2 1.144(3) .
C2 Mn1 1.817(2) .
C3 O3 1.145(3) .
C3 Mn1 1.821(2) .
C4 C5 1.493(3) .
C4 N1 1.494(3) .
C14 C15 1.500(3) .
C14 N1 1.495(3) .
C24 C25 1.505(3) .
C24 N1 1.503(3) .
C5 C6 1.415(3) .
C5 N2 1.328(3) .
C6 C7 1.356(3) .
C7 C8 1.414(3) .
C8 C9 1.421(3) .
C8 C10 1.416(3) .
C9 C13 1.411(3) .
C9 N2 1.396(3) .
C10 C11 1.364(3) .
C11 C12 1.397(3) .
C12 C13 1.373(3) .
C15 C16 1.404(3) .
C15 N3 1.330(3) .
C16 C17 1.363(3) .
C17 C18 1.410(3) .
C18 C19 1.423(3) .
C18 C20 1.417(3) .
C19 C23 1.414(3) .
C19 N3 1.388(3) .
C20 C21 1.363(3) .
C21 C22 1.405(3) .
C22 C23 1.375(3) .
C25 C26 1.429(3) .
C25 N4 1.310(3) .
C26 C27 1.361(3) .
C27 C28 1.416(3) .
C28 C29 1.421(3) .
C28 C30 1.413(3) .
C29 C33 1.414(3) .
C29 N4 1.373(3) .
C30 C31 1.372(3) .
C31 C32 1.413(3) .
C32 C33 1.374(3) .
N1 Mn1 2.1007(18) .
N2 Mn1 2.1056(18) .
N3 Mn1 2.0926(17) .

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
Mn1 C1 O1 170.54(19) . .
Mn1 C2 O2 174.40(19) . .
Mn1 C3 O3 173.90(19) . .
N1 C4 C5 113.20(17) . .
N1 C14 C15 108.92(17) . .
N1 C24 C25 116.22(18) . .
C6 C5 C4 116.73(19) . .
N2 C5 C4 119.53(19) . .
N2 C5 C6 123.7(2) . .
C7 C6 C5 119.9(2) . .
C8 C7 C6 118.9(2) . .
C9 C8 C7 118.8(2) . .
C10 C8 C7 121.3(2) . .
C10 C8 C9 119.9(2) . .
C13 C9 C8 117.88(19) . .
N2 C9 C8 121.35(19) . .
N2 C9 C13 120.77(19) . .
C11 C10 C8 120.6(2) . .
C12 C11 C10 119.5(2) . .
C13 C12 C11 121.5(2) . .
C12 C13 C9 120.5(2) . .
C16 C15 C14 120.74(19) . .
N3 C15 C14 115.63(18) . .
N3 C15 C16 123.6(2) . .
C17 C16 C15 119.0(2) . .
C18 C17 C16 119.7(2) . .
C19 C18 C17 118.7(2) . .
C20 C18 C17 122.4(2) . .
C20 C18 C19 119.0(2) . .
C23 C19 C18 118.3(2) . .
N3 C19 C18 120.42(19) . .
N3 C19 C23 121.27(19) . .
C21 C20 C18 121.5(2) . .
C22 C21 C20 119.3(2) . .
C23 C22 C21 121.1(2) . .
C22 C23 C19 120.7(2) . .
C26 C25 C24 116.8(2) . .
N4 C25 C24 120.26(19) . .
N4 C25 C26 122.9(2) . .
C27 C26 C25 119.1(2) . .
C28 C27 C26 119.7(2) . .
C29 C28 C27 117.4(2) . .
C30 C28 C27 123.6(2) . .
C30 C28 C29 119.0(2) . .
C33 C29 C28 119.2(2) . .
N4 C29 C28 122.1(2) . .
N4 C29 C33 118.7(2) . .
C31 C30 C28 120.8(2) . .
C32 C31 C30 120.1(2) . .
C33 C32 C31 120.5(2) . .
C32 C33 C29 120.3(2) . .
C14 N1 C4 107.53(16) . .
C24 N1 C4 110.97(16) . .
C24 N1 C14 106.39(16) . .
Mn1 N1 C4 109.55(13) . .
Mn1 N1 C14 103.50(12) . .
Mn1 N1 C24 118.11(13) . .
C9 N2 C5 117.27(18) . .
Mn1 N2 C5 113.02(14) . .
Mn1 N2 C9 129.67(14) . .
C19 N3 C15 118.42(18) . .
Mn1 N3 C15 112.53(14) . .
Mn1 N3 C19 128.70(14) . .
C29 N4 C25 118.70(19) . .
C2 Mn1 C1 80.99(9) . .
C3 Mn1 C1 85.93(9) . .
C3 Mn1 C2 90.05(9) . .
N1 Mn1 C1 171.60(8) . .
N1 Mn1 C2 92.21(8) . .
N1 Mn1 C3 99.07(8) . .
N2 Mn1 C1 104.74(8) . .
N2 Mn1 C2 174.21(8) . .
N2 Mn1 C3 91.22(8) . .
N2 Mn1 N1 82.01(7) . .
N3 Mn1 C1 97.11(8) . .
N3 Mn1 C2 91.28(8) . .
N3 Mn1 C3 176.84(8) . .
N3 Mn1 N1 78.02(7) . .
N3 Mn1 N2 87.18(7) . .

_chemical_name_systematic        '[Mn(CO)3(k3N-tqa]Br*(H2O)3'
_exptl_crystal_colour            yellow
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_properties_physical    Light-sensitive,Photo-sensitive
