# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_kub_CM33_0m
_database_code_depnum_ccdc_archive 'CCDC 1480116'
#Added by publCIF



_audit_update_record             
;
2016-05-16 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;
_publcif_datablock.id            {84b85df4-16ec-4872-b1fd-0fe057f3ff67}
#Added by publCIF




_diffrn_detector_area_resol_mean ?
#Added by publCIF




_symmetry_space_group_name_hall  '-P 1'



_atom_sites_solution_primary     direct
#Added by publCIF




_refine_ls_extinction_coef       ?
#Added by publCIF




_refine_ls_extinction_method     none
#Added by publCIF




_atom_sites_solution_hydrogens   geom
#Added by publCIF




_atom_sites_solution_secondary   ?
#Added by publCIF




_diffrn_radiation_monochromator  graphite
#Added by publCIF




_diffrn_radiation_source         'fine-focus sealed tube'
#Added by publCIF




_computing_structure_solution    Olex2
#Added by publCIF




_computing_data_collection       'Bruker APEX2'
#Added by publCIF




_cell_special_details            ?
# publcif _publ_body_element loop end
_audit_creation_date             2015-01-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.06 svn.r3119 for OlexSys, GUI svn.r4979)
;
_chemical_formula_moiety         'C19 H18 Br Mn N4 O5, C2 H3 N'
_chemical_formula_sum            'C21 H21 Br Mn N5 O5'
_chemical_formula_weight         558.27
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   8.4602(13)
_cell_length_b                   8.6080(15)
_cell_length_c                   17.623(3)
_cell_angle_alpha                101.163(6)
_cell_angle_beta                 95.668(5)
_cell_angle_gamma                112.647(5)
_cell_volume                     1140.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4953
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.339
_cell_measurement_theta_min      2.401
_exptl_absorpt_coefficient_mu    2.373
_exptl_absorpt_correction_T_max  0.0932
_exptl_absorpt_correction_T_min  0.0565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1581 before and 0.0710 after correction.
The Ratio of minimum to maximum transmission is 0.6062.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_density_diffrn    1.6255
_exptl_crystal_description       plate
_exptl_crystal_F_000             564.3709
_exptl_crystal_preparation       'vapor diffusion of pentane into'
_exptl_crystal_recrystallization_method 
'vapor diffusion of diethyl ether into acetonitrile solution'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18832
_diffrn_reflns_theta_full        26.4107
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.40
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9908
_diffrn_measured_fraction_theta_max 0.9908
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                3660
_reflns_number_total             4653
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.5595
_refine_diff_density_min         -0.6397
_refine_diff_density_rms         0.1431
_refine_ls_d_res_high            0.7989
_refine_ls_d_res_low             8.4848
_refine_ls_goodness_of_fit_ref   1.0295
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4653
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.0295
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0297P)²+0.2964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0856
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C27(H27a,H27b), C30(H30a,H30b)
2.b Aromatic/amide H refined with riding coordinates:
 N12(H12), N8(H8), C19(H19), C14(H14), C18(H18), C23(H23), C24(H24), C17(H17)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C32(H32a,H32b,H32c), C33(H33a,H33b,H33c)
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
Br1 Br 0.12001(4) 0.85028(4) 0.236165(17) 0.02003(10) Uani 1.000000 .
Mn1 Mn 0.26647(5) 0.96013(6) 0.12667(2) 0.01569(12) Uani 1.000000 .
O1 O 0.6609(3) 1.9314(3) 0.44399(12) 0.0311(6) Uani 1.000000 .
O9 O 0.2535(3) 0.6111(3) 0.06068(13) 0.0298(5) Uani 1.000000 .
O3 O -0.0865(3) 0.8316(3) 0.03111(12) 0.0271(5) Uani 1.000000 .
O7 O 0.4037(3) 1.1108(3) -0.00196(12) 0.0249(5) Uani 1.000000 .
O5 O 1.2084(3) 1.4446(3) 0.51279(12) 0.0235(5) Uani 1.000000 .
N4 N 0.5034(3) 1.0449(3) 0.19921(13) 0.0165(5) Uani 1.000000 .
N12 N 0.9613(3) 1.2177(3) 0.44306(13) 0.0172(5) Uani 1.000000 .
H12 H 0.8670(3) 1.1284(3) 0.44517(13) 0.0206(7) Uiso 1.000000 R
N8 N 0.4168(3) 1.6880(3) 0.42785(13) 0.0153(5) Uani 1.000000 .
H8 H 0.3534(3) 1.6064(3) 0.44918(13) 0.0184(6) Uiso 1.000000 R
N31 N -0.1851(4) 1.3162(4) 0.11965(17) 0.0402(8) Uani 1.000000 .
C19 C 0.4561(4) 1.4354(4) 0.30239(16) 0.0157(6) Uani 1.000000 .
H19 H 0.5516(4) 1.4893(4) 0.34566(16) 0.0188(8) Uiso 1.000000 R
C13 C 0.5500(4) 1.1930(4) 0.25610(16) 0.0157(6) Uani 1.000000 .
C16 C 1.0757(4) 1.3135(4) 0.50962(17) 0.0186(7) Uani 1.000000 .
C20 C 0.4308(4) 1.2804(4) 0.25082(16) 0.0144(6) Uani 1.000000 .
C14 C 0.7030(4) 1.2609(4) 0.31228(17) 0.0176(7) Uani 1.000000 .
H14 H 0.7293(4) 1.3622(4) 0.35306(17) 0.0212(8) Uiso 1.000000 R
C21 C 0.2590(4) 0.7471(4) 0.08522(17) 0.0198(7) Uani 1.000000 .
C1 C 1.0336(4) 1.2506(4) 0.58296(17) 0.0262(8) Uani 1.000000 .
H1a H 1.1156(17) 1.203(2) 0.5995(7) 0.0392(11) Uiso 1.000000 GR
H1b H 1.044(3) 1.3483(7) 0.6253(4) 0.0392(11) Uiso 1.000000 GR
H1c H 0.9143(10) 1.1600(19) 0.5714(4) 0.0392(11) Uiso 1.000000 GR
C22 C 0.3553(4) 1.0496(4) 0.04768(17) 0.0177(7) Uani 1.000000 .
C18 C 0.1857(4) 1.2746(4) 0.17644(16) 0.0171(6) Uani 1.000000 .
H18 H 0.0918(4) 1.2197(4) 0.13246(16) 0.0205(8) Uiso 1.000000 R
C23 C 0.7701(4) 1.0311(4) 0.24941(17) 0.0213(7) Uani 1.000000 .
H23 H 0.8451(4) 0.9727(4) 0.24484(17) 0.0256(8) Uiso 1.000000 R
C15 C 0.5627(4) 1.8191(4) 0.47198(17) 0.0183(7) Uani 1.000000 .
C24 C 0.2047(4) 1.4297(4) 0.22528(16) 0.0170(6) Uani 1.000000 .
H24 H 0.1256(4) 1.4801(4) 0.21457(16) 0.0204(8) Uiso 1.000000 R
C17 C 0.6131(4) 0.9665(4) 0.19653(17) 0.0206(7) Uani 1.000000 .
H17 H 0.5822(4) 0.8623(4) 0.15678(17) 0.0248(8) Uiso 1.000000 R
C25 C 0.3409(4) 1.5112(4) 0.29033(16) 0.0156(6) Uani 1.000000 .
C10 C 0.0505(4) 0.8861(4) 0.06946(17) 0.0189(7) Uani 1.000000 .
C32 C -0.3374(5) 1.5249(5) 0.1177(2) 0.0365(9) Uani 1.000000 .
H32a H -0.326(3) 1.566(2) 0.0695(7) 0.0547(13) Uiso 1.000000 GR
H32b H -0.4612(7) 1.4627(9) 0.1189(13) 0.0547(13) Uiso 1.000000 GR
H32c H -0.2830(19) 1.6247(15) 0.1638(7) 0.0547(13) Uiso 1.000000 GR
C29 C -0.2510(4) 1.4084(5) 0.11911(19) 0.0306(8) Uani 1.000000 .
C27 C 0.3609(4) 1.6777(4) 0.34567(16) 0.0198(7) Uani 1.000000 .
H27a H 0.2479(4) 1.6877(4) 0.33943(16) 0.0238(8) Uiso 1.000000 R
H27b H 0.4473(4) 1.7774(4) 0.33083(16) 0.0238(8) Uiso 1.000000 R
C33 C 0.5966(4) 1.8212(4) 0.55724(17) 0.0242(7) Uani 1.000000 .
H33a H 0.7220(5) 1.859(2) 0.5755(3) 0.0362(11) Uiso 1.000000 GR
H33b H 0.557(2) 1.9017(19) 0.5881(2) 0.0362(11) Uiso 1.000000 GR
H33c H 0.533(2) 1.7040(7) 0.5639(2) 0.0362(11) Uiso 1.000000 GR
C26 C 0.8168(4) 1.1803(4) 0.30864(17) 0.0176(7) Uani 1.000000 .
C30 C 0.9870(4) 1.2556(4) 0.36698(16) 0.0190(7) Uani 1.000000 .
H30a H 1.0426(4) 1.3832(4) 0.37420(16) 0.0228(8) Uiso 1.000000 R
H30b H 1.0667(4) 1.2068(4) 0.34566(16) 0.0228(8) Uiso 1.000000 R
N0AA N 0.2944(3) 1.1983(3) 0.18856(13) 0.0157(5) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Mn1 2.5355(6) . ?
Mn1 N4 2.047(2) . ?
Mn1 C21 1.812(3) . ?
Mn1 C22 1.809(3) . ?
Mn1 C10 1.803(3) . ?
Mn1 N0AA 2.040(2) . ?
O1 C15 1.231(3) . ?
O9 C21 1.148(4) . ?
O3 C10 1.151(3) . ?
O7 C22 1.137(3) . ?
O5 C16 1.235(3) . ?
N4 C13 1.351(4) . ?
N4 C17 1.341(4) . ?
N12 C16 1.334(4) . ?
N12 C30 1.457(3) . ?
N8 C15 1.341(4) . ?
N8 C27 1.453(3) . ?
N31 C29 1.133(4) . ?
C19 C20 1.388(4) . ?
C19 C25 1.387(4) . ?
C13 C20 1.478(4) . ?
C13 C14 1.392(4) . ?
C16 C1 1.518(4) . ?
C20 N0AA 1.362(3) . ?
C14 C26 1.386(4) . ?
C18 C24 1.383(4) . ?
C18 N0AA 1.343(3) . ?
C23 C17 1.388(4) . ?
C23 C26 1.380(4) . ?
C15 C33 1.497(4) . ?
C24 C25 1.392(4) . ?
C25 C27 1.507(4) . ?
C32 C29 1.453(5) . ?
C26 C30 1.511(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
N4 Mn1 Br1 88.82(6) . . ?
C21 Mn1 Br1 90.27(9) . . ?
C21 Mn1 N4 93.94(11) . . ?
C22 Mn1 Br1 173.92(9) . . ?
C22 Mn1 N4 95.10(11) . . ?
C22 Mn1 C21 94.08(13) . . ?
C10 Mn1 Br1 87.12(9) . . ?
C10 Mn1 N4 175.61(11) . . ?
C10 Mn1 C21 87.74(13) . . ?
C10 Mn1 C22 88.81(12) . . ?
N0AA Mn1 Br1 84.91(6) . . ?
N0AA Mn1 N4 78.84(9) . . ?
N0AA Mn1 C21 171.37(11) . . ?
N0AA Mn1 C22 91.28(11) . . ?
N0AA Mn1 C10 99.13(11) . . ?
C13 N4 Mn1 115.74(18) . . ?
C17 N4 Mn1 126.5(2) . . ?
C17 N4 C13 117.7(2) . . ?
C30 N12 C16 122.4(2) . . ?
C27 N8 C15 121.6(2) . . ?
C25 C19 C20 119.5(3) . . ?
C20 C13 N4 114.6(2) . . ?
C14 C13 N4 122.1(3) . . ?
C14 C13 C20 123.3(3) . . ?
N12 C16 O5 123.3(3) . . ?
C1 C16 O5 121.1(3) . . ?
C1 C16 N12 115.6(3) . . ?
C13 C20 C19 123.9(2) . . ?
N0AA C20 C19 122.0(2) . . ?
N0AA C20 C13 114.1(2) . . ?
C26 C14 C13 119.9(3) . . ?
O9 C21 Mn1 178.3(3) . . ?
O7 C22 Mn1 175.5(2) . . ?
N0AA C18 C24 122.8(3) . . ?
C26 C23 C17 119.8(3) . . ?
N8 C15 O1 121.8(3) . . ?
C33 C15 O1 122.4(3) . . ?
C33 C15 N8 115.8(3) . . ?
C25 C24 C18 119.3(3) . . ?
C23 C17 N4 122.7(3) . . ?
C24 C25 C19 118.3(3) . . ?
C27 C25 C19 121.4(2) . . ?
C27 C25 C24 120.2(2) . . ?
O3 C10 Mn1 176.6(3) . . ?
C32 C29 N31 179.3(4) . . ?
C25 C27 N8 113.3(2) . . ?
C23 C26 C14 117.7(3) . . ?
C30 C26 C14 120.8(3) . . ?
C30 C26 C23 121.5(3) . . ?
C26 C30 N12 111.8(2) . . ?
C20 N0AA Mn1 115.76(18) . . ?
C18 N0AA Mn1 126.1(2) . . ?
C18 N0AA C20 118.0(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
