# 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_xsc1639_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 1452076'
_audit_update_record             
;
2016-02-07 deposited with the CCDC.
2016-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '[MnBr(CO)3(adamant)]'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 Br Mn N2 O3'
_chemical_formula_weight         459.22

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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.428(3)
_cell_length_b                   7.2853(15)
_cell_length_c                   18.627(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.986(2)
_cell_angle_gamma                90
_cell_volume                     1912.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    6723
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      24.99

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    2.799
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4388
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15394
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.890
_diffrn_reflns_theta_max         25.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3426
_reflns_number_gt                3055
_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)+(0.1000P)²+0.2298P] 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         3426
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1794
_refine_ls_wR_factor_gt          0.1759
_refine_ls_goodness_of_fit_ref   1.388
_refine_ls_restrained_S_all      1.388
_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
Br1 Br 0.29699(4) 0.04611(7) 0.48029(3) 0.0533(2) Uani 1 1 d . . . . .
Mn1 Mn 0.26387(4) 0.19230(8) 0.58926(4) 0.0352(2) Uani 1 1 d . . . . .
C1 C 0.2365(4) 0.3126(9) 0.6718(3) 0.0535(16) Uani 1 1 d . . . . .
N2 N 0.3474(2) 0.4164(5) 0.58414(19) 0.0306(7) Uani 1 1 d . . . . .
O3 O 0.4044(3) -0.0488(5) 0.7072(2) 0.0588(10) Uani 1 1 d . . . . .
O2 O 0.1299(3) -0.1014(7) 0.5823(3) 0.0882(15) Uani 1 1 d . . . . .
N1 N 0.1643(2) 0.3502(5) 0.5045(2) 0.0384(8) Uani 1 1 d . . . . .
C4 C 0.0725(3) 0.3128(7) 0.4622(3) 0.0507(12) Uani 1 1 d . . . . .
H4 H 0.0485 0.2020 0.4710 0.061 Uiso 1 1 calc R U . . .
C5 C 0.0121(3) 0.4295(7) 0.4066(3) 0.0523(13) Uani 1 1 d . . . . .
H5 H -0.0512 0.3975 0.3785 0.063 Uiso 1 1 calc R U . . .
C6 C 0.0461(3) 0.5939(7) 0.3929(3) 0.0506(12) Uani 1 1 d . . . . .
H6 H 0.0057 0.6771 0.3569 0.061 Uiso 1 1 calc R U . . .
C7 C 0.1415(3) 0.6340(7) 0.4338(3) 0.0470(11) Uani 1 1 d . . . . .
H7 H 0.1669 0.7424 0.4243 0.056 Uiso 1 1 calc R U . . .
C8 C 0.1983(3) 0.5093(6) 0.4890(3) 0.0381(9) Uani 1 1 d . . . . .
C9 C 0.2997(3) 0.5383(6) 0.5351(3) 0.0372(10) Uani 1 1 d . . . . .
H9 H 0.3290 0.6447 0.5286 0.045 Uiso 1 1 calc R U . . .
C10 C 0.4518(3) 0.4451(5) 0.6309(2) 0.0327(9) Uani 1 1 d . . . . .
C19 C 0.4682(3) 0.4551(6) 0.7185(3) 0.0386(10) Uani 1 1 d . . . . .
H19A H 0.4345 0.5597 0.7269 0.046 Uiso 1 1 calc R U . . .
H19B H 0.4438 0.3448 0.7330 0.046 Uiso 1 1 calc R U . . .
C16 C 0.5753(3) 0.4738(7) 0.7701(3) 0.0451(11) Uani 1 1 d . . . . .
H16 H 0.5857 0.4797 0.8256 0.054 Uiso 1 1 calc R U . . .
C15 C 0.6279(3) 0.3062(7) 0.7567(3) 0.0535(13) Uani 1 1 d . . . . .
H15A H 0.6042 0.1946 0.7707 0.064 Uiso 1 1 calc R U . . .
H15B H 0.6952 0.3158 0.7896 0.064 Uiso 1 1 calc R U . . .
C14 C 0.6121(3) 0.2990(7) 0.6698(3) 0.0517(12) Uani 1 1 d . . . . .
H14 H 0.6459 0.1927 0.6616 0.062 Uiso 1 1 calc R U . . .
C17 C 0.5056(3) 0.2796(6) 0.6170(3) 0.0412(10) Uani 1 1 d . . . . .
H17A H 0.4814 0.1664 0.6294 0.049 Uiso 1 1 calc R U . . .
H17B H 0.4961 0.2753 0.5623 0.049 Uiso 1 1 calc R U . . .
C13 C 0.6506(4) 0.4735(8) 0.6480(4) 0.0589(14) Uani 1 1 d . . . . .
H13A H 0.6413 0.4684 0.5933 0.071 Uiso 1 1 calc R U . . .
H13B H 0.7181 0.4845 0.6801 0.071 Uiso 1 1 calc R U . . .
C12 C 0.5984(3) 0.6382(7) 0.6614(3) 0.0489(11) Uani 1 1 d . . . . .
H12 H 0.6226 0.7507 0.6472 0.059 Uiso 1 1 calc R U . . .
C18 C 0.6138(3) 0.6477(7) 0.7478(3) 0.0508(12) Uani 1 1 d . . . . .
H18A H 0.5815 0.7544 0.7563 0.061 Uiso 1 1 calc R U . . .
H18B H 0.6810 0.6598 0.7807 0.061 Uiso 1 1 calc R U . . .
C11 C 0.4905(3) 0.6210(6) 0.6099(3) 0.0415(10) Uani 1 1 d . . . . .
H11A H 0.4576 0.7266 0.6185 0.050 Uiso 1 1 calc R U . . .
H11B H 0.4796 0.6185 0.5548 0.050 Uiso 1 1 calc R U . . .
C3 C 0.3533(3) 0.0498(6) 0.6608(3) 0.0398(10) Uani 1 1 d . . . . .
C2 C 0.1810(4) 0.0120(8) 0.5839(3) 0.0542(13) Uani 1 1 d . . . . .
O1 O 0.2269(4) 0.3606(9) 0.7096(4) 0.0853(16) Uani 1 1 d . . . . .


_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
Br1 Mn1 2.5216(9) . y
Mn1 C2 1.807(5) . y
Mn1 C3 1.807(5) . y
Mn1 C1 1.959(8) . y
Mn1 N1 2.051(4) . y
Mn1 N2 2.106(3) . y
C1 O1 0.852(7) . ?
N2 C9 1.272(6) . ?
N2 C10 1.503(5) . ?
O3 C3 1.153(6) . ?
O2 C2 1.135(7) . ?
N1 C4 1.339(6) . ?
N1 C8 1.351(6) . ?
C4 C5 1.371(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.461(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.531(6) . ?
C10 C17 1.544(6) . ?
C10 C19 1.549(6) . ?
C19 C16 1.544(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C16 C18 1.527(8) . ?
C16 C15 1.542(7) . ?
C16 H16 0.9800 . ?
C15 C14 1.535(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C14 C13 1.528(8) . ?
C14 C17 1.540(6) . ?
C14 H14 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C13 C12 1.521(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 C18 1.531(7) . ?
C12 C11 1.552(6) . ?
C12 H12 0.9800 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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
C2 Mn1 C3 86.2(2) . . y
C2 Mn1 C1 89.7(3) . . y
C3 Mn1 C1 91.2(2) . . y
C2 Mn1 N1 94.23(19) . . y
C3 Mn1 N1 177.56(18) . . y
C1 Mn1 N1 91.18(19) . . y
C2 Mn1 N2 173.26(19) . . y
C3 Mn1 N2 100.44(17) . . y
C1 Mn1 N2 91.12(18) . . y
N1 Mn1 N2 79.08(13) . . y
C2 Mn1 Br1 91.1(2) . . y
C3 Mn1 Br1 90.43(15) . . y
C1 Mn1 Br1 178.21(16) . . y
N1 Mn1 Br1 87.16(11) . . y
N2 Mn1 Br1 87.89(9) . . y
O1 C1 Mn1 176.6(8) . . ?
C9 N2 C10 119.4(3) . . ?
C9 N2 Mn1 112.8(3) . . ?
C10 N2 Mn1 127.8(3) . . ?
C4 N1 C8 117.3(4) . . ?
C4 N1 Mn1 128.4(3) . . ?
C8 N1 Mn1 114.3(3) . . ?
N1 C4 C5 123.4(4) . . ?
N1 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
C4 C5 C6 119.2(4) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C7 118.8(4) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C8 C7 C6 118.7(4) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
N1 C8 C7 122.5(4) . . ?
N1 C8 C9 114.5(4) . . ?
C7 C8 C9 123.0(4) . . ?
N2 C9 C8 119.3(4) . . ?
N2 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
N2 C10 C11 114.0(3) . . ?
N2 C10 C17 108.5(3) . . ?
C11 C10 C17 108.6(4) . . ?
N2 C10 C19 107.1(3) . . ?
C11 C10 C19 108.5(3) . . ?
C17 C10 C19 110.2(3) . . ?
C16 C19 C10 109.6(4) . . ?
C16 C19 H19A 109.8 . . ?
C10 C19 H19A 109.8 . . ?
C16 C19 H19B 109.8 . . ?
C10 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
C18 C16 C15 108.9(4) . . ?
C18 C16 C19 109.9(4) . . ?
C15 C16 C19 109.3(4) . . ?
C18 C16 H16 109.6 . . ?
C15 C16 H16 109.6 . . ?
C19 C16 H16 109.6 . . ?
C16 C15 C14 109.3(4) . . ?
C16 C15 H15A 109.8 . . ?
C14 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
C13 C14 C17 109.6(4) . . ?
C13 C14 C15 109.9(4) . . ?
C17 C14 C15 110.3(4) . . ?
C13 C14 H14 109.0 . . ?
C17 C14 H14 109.0 . . ?
C15 C14 H14 109.0 . . ?
C14 C17 C10 109.1(4) . . ?
C14 C17 H17A 109.9 . . ?
C10 C17 H17A 109.9 . . ?
C14 C17 H17B 109.9 . . ?
C10 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C14 C13 C12 108.8(4) . . ?
C14 C13 H13A 109.9 . . ?
C12 C13 H13A 109.9 . . ?
C14 C13 H13B 109.9 . . ?
C12 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C18 C12 C13 110.0(5) . . ?
C18 C12 C11 108.8(4) . . ?
C13 C12 C11 110.0(4) . . ?
C18 C12 H12 109.3 . . ?
C13 C12 H12 109.3 . . ?
C11 C12 H12 109.3 . . ?
C12 C18 C16 109.7(4) . . ?
C12 C18 H18A 109.7 . . ?
C16 C18 H18A 109.7 . . ?
C12 C18 H18B 109.7 . . ?
C16 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C10 C11 C12 110.0(4) . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
O3 C3 Mn1 174.4(4) . . ?
O2 C2 Mn1 178.5(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C4 C5 -2.0(8) . . . . ?
Mn1 N1 C4 C5 -179.9(4) . . . . ?
N1 C4 C5 C6 -0.2(9) . . . . ?
C4 C5 C6 C7 2.4(8) . . . . ?
C5 C6 C7 C8 -2.3(8) . . . . ?
C4 N1 C8 C7 2.1(7) . . . . ?
Mn1 N1 C8 C7 -179.7(4) . . . . ?
C4 N1 C8 C9 -177.8(4) . . . . ?
Mn1 N1 C8 C9 0.4(5) . . . . ?
C6 C7 C8 N1 0.0(8) . . . . ?
C6 C7 C8 C9 179.9(5) . . . . ?
C10 N2 C9 C8 179.3(4) . . . . ?
Mn1 N2 C9 C8 -1.2(5) . . . . ?
N1 C8 C9 N2 0.6(6) . . . . ?
C7 C8 C9 N2 -179.3(5) . . . . ?
C9 N2 C10 C11 -2.9(5) . . . . ?
Mn1 N2 C10 C11 177.7(3) . . . . ?
C9 N2 C10 C17 -124.0(4) . . . . ?
Mn1 N2 C10 C17 56.6(4) . . . . ?
C9 N2 C10 C19 117.1(4) . . . . ?
Mn1 N2 C10 C19 -62.3(4) . . . . ?
N2 C10 C19 C16 176.9(3) . . . . ?
C11 C10 C19 C16 -59.7(5) . . . . ?
C17 C10 C19 C16 59.1(4) . . . . ?
C10 C19 C16 C18 59.7(5) . . . . ?
C10 C19 C16 C15 -59.8(5) . . . . ?
C18 C16 C15 C14 -59.6(5) . . . . ?
C19 C16 C15 C14 60.5(5) . . . . ?
C16 C15 C14 C13 60.3(5) . . . . ?
C16 C15 C14 C17 -60.7(5) . . . . ?
C13 C14 C17 C10 -61.7(5) . . . . ?
C15 C14 C17 C10 59.4(5) . . . . ?
N2 C10 C17 C14 -175.4(4) . . . . ?
C11 C10 C17 C14 60.3(5) . . . . ?
C19 C10 C17 C14 -58.4(5) . . . . ?
C17 C14 C13 C12 61.2(5) . . . . ?
C15 C14 C13 C12 -60.2(6) . . . . ?
C14 C13 C12 C18 60.2(5) . . . . ?
C14 C13 C12 C11 -59.7(6) . . . . ?
C13 C12 C18 C16 -60.6(5) . . . . ?
C11 C12 C18 C16 60.0(5) . . . . ?
C15 C16 C18 C12 59.7(5) . . . . ?
C19 C16 C18 C12 -60.0(5) . . . . ?
N2 C10 C11 C12 179.8(4) . . . . ?
C17 C10 C11 C12 -59.1(5) . . . . ?
C19 C10 C11 C12 60.6(5) . . . . ?
C18 C12 C11 C10 -61.0(5) . . . . ?
C13 C12 C11 C10 59.6(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9 Br1 0.93 3.04 3.833(4) 144.2 1_565
C7 H7 Br1 0.93 2.88 3.719(5) 150.3 1_565
C4 H4 O2 0.93 2.62 3.272(6) 127.4 3_556
C9 H9 Br1 0.93 3.04 3.833(4) 144.2 1_565
C7 H7 Br1 0.93 2.88 3.719(5) 150.3 1_565
C4 H4 O2 0.93 2.62 3.272(6) 127.4 3_556
C4 H4 O2 0.93 2.62 3.272(6) 127.4 3_556
C7 H7 Br1 0.93 2.88 3.719(5) 150.3 1_565
C9 H9 Br1 0.93 3.04 3.833(4) 144.2 1_565

_refine_diff_density_max         0.898
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.090

_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# 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_xsc1597f-auto
_database_code_depnum_ccdc_archive 'CCDC 1452077'
_audit_update_record             
;
2016-02-07 deposited with the CCDC.
2016-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '[MnBr(CO)3(triaza-adamant)]'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 Br Mn N5 O3'
_chemical_formula_weight         462.20

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.1920(3)
_cell_length_b                   20.6213(9)
_cell_length_c                   12.1639(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.6430(10)
_cell_angle_gamma                90
_cell_volume                     1800.36(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    7226
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      24.95

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    2.979
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5862
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15394
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.592
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_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             3169
_reflns_number_gt                2800
_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)+(0.1000P)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_number_reflns         3169
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1436
_refine_ls_wR_factor_gt          0.1390
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_restrained_S_all      1.211
_refine_ls_shift/su_max          0.001
_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
Br1 Br 1.25923(5) 0.06673(2) 0.49159(3) 0.0483(2) Uani 1 1 d . . . . .
Mn1 Mn 1.09425(7) 0.17146(2) 0.44645(4) 0.0357(2) Uani 1 1 d . . . . .
O1 O 0.9005(4) 0.28944(19) 0.4034(3) 0.0691(9) Uani 1 1 d . . . . .
O2 O 1.4342(4) 0.23452(16) 0.5420(3) 0.0710(9) Uani 1 1 d . . . . .
O3 O 1.2853(4) 0.18700(14) 0.2406(2) 0.0643(8) Uani 1 1 d . . . . .
N1 N 0.9682(4) 0.15784(13) 0.5911(2) 0.0390(6) Uani 1 1 d . . . . .
N2 N 0.8619(3) 0.11627(12) 0.3927(2) 0.0316(6) Uani 1 1 d . . . . .
N3 N 0.9404(4) 0.02372(15) 0.1330(2) 0.0497(8) Uani 1 1 d . . . . .
N4 N 0.6025(4) 0.02584(15) 0.1537(2) 0.0473(7) Uani 1 1 d . . . . .
N5 N 0.7609(5) 0.12185(16) 0.0847(2) 0.0496(7) Uani 1 1 d . . . . .
C1 C 0.9631(6) 0.2503(2) 0.4189(3) 0.0476(9) Uani 1 1 d . . . . .
C2 C 1.3001(5) 0.21162(18) 0.5078(3) 0.0457(8) Uani 1 1 d . . . . .
C3 C 1.2067(5) 0.17894(15) 0.3189(3) 0.0429(8) Uani 1 1 d . . . . .
C4 C 1.0286(6) 0.17625(18) 0.6936(3) 0.0524(10) Uani 1 1 d . . . . .
H4 H 1.1393 0.1996 0.7024 0.063 Uiso 1 1 calc R U . . .
C5 C 0.9359(6) 0.1624(2) 0.7845(3) 0.0569(11) Uani 1 1 d . . . . .
H5 H 0.9828 0.1760 0.8536 0.068 Uiso 1 1 calc R U . . .
C6 C 0.7735(6) 0.1284(2) 0.7734(3) 0.0629(12) Uani 1 1 d . . . . .
H6 H 0.7068 0.1196 0.8347 0.075 Uiso 1 1 calc R U . . .
C7 C 0.7092(5) 0.1073(2) 0.6712(3) 0.0528(9) Uani 1 1 d . . . . .
H7 H 0.6005 0.0828 0.6625 0.063 Uiso 1 1 calc R U . . .
C8 C 0.8088(5) 0.12292(17) 0.5811(3) 0.0417(8) Uani 1 1 d . . . . .
C9 C 0.7557(4) 0.10157(18) 0.4700(3) 0.0391(8) Uani 1 1 d . . . . .
H9 H 0.6472 0.0778 0.4550 0.047 Uiso 1 1 calc R U . . .
C10 C 0.8150(4) 0.09077(16) 0.2801(3) 0.0347(7) Uani 1 1 d . . . . .
C11 C 0.9751(5) 0.04554(17) 0.2483(3) 0.0403(8) Uani 1 1 d . . . . .
H11A H 1.0928 0.0686 0.2564 0.048 Uiso 1 1 calc R U . . .
H11B H 0.9826 0.0083 0.2971 0.048 Uiso 1 1 calc R U . . .
C12 C 0.7622(6) -0.0128(2) 0.1259(3) 0.0555(10) Uani 1 1 d . . . . .
H12A H 0.7399 -0.0294 0.0516 0.067 Uiso 1 1 calc R U . . .
H12B H 0.7737 -0.0497 0.1753 0.067 Uiso 1 1 calc R U . . .
C13 C 0.5912(6) 0.0826(2) 0.0781(3) 0.0500(9) Uani 1 1 d . . . . .
H13A H 0.5677 0.0674 0.0031 0.060 Uiso 1 1 calc R U . . .
H13B H 0.4868 0.1096 0.0960 0.060 Uiso 1 1 calc R U . . .
C14 C 0.7919(5) 0.14653(17) 0.1975(3) 0.0406(7) Uani 1 1 d . . . . .
H14A H 0.6870 0.1733 0.2154 0.049 Uiso 1 1 calc R U . . .
H14B H 0.9028 0.1734 0.2025 0.049 Uiso 1 1 calc R U . . .
C15 C 0.6332(5) 0.04963(18) 0.2682(3) 0.0416(8) Uani 1 1 d . . . . .
H15A H 0.6431 0.0131 0.3184 0.050 Uiso 1 1 calc R U . . .
H15B H 0.5280 0.0759 0.2871 0.050 Uiso 1 1 calc R U . . .
C16 C 0.9182(6) 0.0801(2) 0.0601(3) 0.0537(10) Uani 1 1 d . . . . .
H16A H 0.9005 0.0651 -0.0154 0.064 Uiso 1 1 calc R U . . .
H16B H 1.0318 0.1055 0.0663 0.064 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
Br1 Mn1 2.5082(6) . y
Mn1 C3 1.801(4) . y
Mn1 C2 1.815(4) . y
Mn1 C1 1.899(5) . y
Mn1 N1 2.049(3) . y
Mn1 N2 2.092(3) . y
O1 C1 0.937(5) . ?
O2 C2 1.130(5) . ?
O3 C3 1.150(4) . ?
N1 C4 1.348(4) . ?
N1 C8 1.353(5) . ?
N2 C9 1.285(4) . ?
N2 C10 1.485(4) . ?
N3 C16 1.464(5) . ?
N3 C11 1.480(4) . ?
N3 C12 1.484(5) . ?
N4 C12 1.455(5) . ?
N4 C15 1.480(4) . ?
N4 C13 1.488(5) . ?
N5 C13 1.462(5) . ?
N5 C14 1.467(4) . ?
N5 C16 1.468(5) . ?
C4 C5 1.358(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.362(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.450(5) . ?
C9 H9 0.9300 . ?
C10 C14 1.530(5) . ?
C10 C11 1.550(4) . ?
C10 C15 1.558(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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
C3 Mn1 C2 85.16(16) . . y
C3 Mn1 C1 91.12(16) . . y
C2 Mn1 C1 93.70(16) . . y
C3 Mn1 N1 177.03(13) . . y
C2 Mn1 N1 95.94(14) . . y
C1 Mn1 N1 91.57(14) . . y
C3 Mn1 N2 99.83(13) . . y
C2 Mn1 N2 172.44(14) . . y
C1 Mn1 N2 91.88(13) . . y
N1 Mn1 N2 78.80(10) . . y
C3 Mn1 Br1 91.73(11) . . y
C2 Mn1 Br1 86.61(12) . . y
C1 Mn1 Br1 177.15(11) . . y
N1 Mn1 Br1 85.58(8) . . y
N2 Mn1 Br1 87.56(7) . . y
C4 N1 C8 117.0(3) . . ?
C4 N1 Mn1 128.4(3) . . ?
C8 N1 Mn1 114.5(2) . . ?
C9 N2 C10 118.7(3) . . ?
C9 N2 Mn1 113.5(2) . . ?
C10 N2 Mn1 127.67(19) . . ?
C16 N3 C11 109.8(3) . . ?
C16 N3 C12 107.9(3) . . ?
C11 N3 C12 107.6(3) . . ?
C12 N4 C15 109.1(3) . . ?
C12 N4 C13 107.5(3) . . ?
C15 N4 C13 108.6(3) . . ?
C13 N5 C14 108.7(3) . . ?
C13 N5 C16 108.4(3) . . ?
C14 N5 C16 108.7(3) . . ?
O1 C1 Mn1 178.3(5) . . ?
O2 C2 Mn1 176.0(4) . . ?
O3 C3 Mn1 175.5(3) . . ?
N1 C4 C5 123.2(4) . . ?
N1 C4 H4 118.4 . . ?
C5 C4 H4 118.4 . . ?
C4 C5 C6 119.4(4) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 119.5(4) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C8 118.8(4) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
N1 C8 C7 122.1(3) . . ?
N1 C8 C9 114.6(3) . . ?
C7 C8 C9 123.2(3) . . ?
N2 C9 C8 118.5(3) . . ?
N2 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
N2 C10 C14 110.4(3) . . ?
N2 C10 C11 108.3(2) . . ?
C14 C10 C11 109.9(3) . . ?
N2 C10 C15 114.8(3) . . ?
C14 C10 C15 107.0(3) . . ?
C11 C10 C15 106.4(3) . . ?
N3 C11 C10 109.7(3) . . ?
N3 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
N3 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
N4 C12 N3 113.6(3) . . ?
N4 C12 H12A 108.9 . . ?
N3 C12 H12A 108.9 . . ?
N4 C12 H12B 108.9 . . ?
N3 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
N5 C13 N4 112.9(3) . . ?
N5 C13 H13A 109.0 . . ?
N4 C13 H13A 109.0 . . ?
N5 C13 H13B 109.0 . . ?
N4 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
N5 C14 C10 111.0(3) . . ?
N5 C14 H14A 109.4 . . ?
C10 C14 H14A 109.4 . . ?
N5 C14 H14B 109.4 . . ?
C10 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N4 C15 C10 110.0(3) . . ?
N4 C15 H15A 109.7 . . ?
C10 C15 H15A 109.7 . . ?
N4 C15 H15B 109.7 . . ?
C10 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N3 C16 N5 113.5(3) . . ?
N3 C16 H16A 108.9 . . ?
N5 C16 H16A 108.9 . . ?
N3 C16 H16B 108.9 . . ?
N5 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C4 C5 -1.2(5) . . . . ?
Mn1 N1 C4 C5 -177.5(3) . . . . ?
N1 C4 C5 C6 -0.1(6) . . . . ?
C4 C5 C6 C7 1.7(7) . . . . ?
C5 C6 C7 C8 -2.0(6) . . . . ?
C4 N1 C8 C7 1.0(5) . . . . ?
Mn1 N1 C8 C7 177.7(3) . . . . ?
C4 N1 C8 C9 -176.9(3) . . . . ?
Mn1 N1 C8 C9 -0.1(4) . . . . ?
C6 C7 C8 N1 0.6(6) . . . . ?
C6 C7 C8 C9 178.3(4) . . . . ?
C10 N2 C9 C8 175.9(3) . . . . ?
Mn1 N2 C9 C8 -1.1(4) . . . . ?
N1 C8 C9 N2 0.9(5) . . . . ?
C7 C8 C9 N2 -177.0(3) . . . . ?
C9 N2 C10 C14 122.9(3) . . . . ?
Mn1 N2 C10 C14 -60.5(3) . . . . ?
C9 N2 C10 C11 -116.8(3) . . . . ?
Mn1 N2 C10 C11 59.8(3) . . . . ?
C9 N2 C10 C15 1.9(4) . . . . ?
Mn1 N2 C10 C15 178.4(2) . . . . ?
C16 N3 C11 C10 56.1(4) . . . . ?
C12 N3 C11 C10 -61.1(4) . . . . ?
N2 C10 C11 N3 -175.2(3) . . . . ?
C14 C10 C11 N3 -54.5(4) . . . . ?
C15 C10 C11 N3 60.9(3) . . . . ?
C15 N4 C12 N3 -60.2(4) . . . . ?
C13 N4 C12 N3 57.4(4) . . . . ?
C16 N3 C12 N4 -57.1(4) . . . . ?
C11 N3 C12 N4 61.3(4) . . . . ?
C14 N5 C13 N4 -60.6(4) . . . . ?
C16 N5 C13 N4 57.4(4) . . . . ?
C12 N4 C13 N5 -57.7(4) . . . . ?
C15 N4 C13 N5 60.2(4) . . . . ?
C13 N5 C14 C10 60.3(4) . . . . ?
C16 N5 C14 C10 -57.5(4) . . . . ?
N2 C10 C14 N5 175.3(3) . . . . ?
C11 C10 C14 N5 55.9(4) . . . . ?
C15 C10 C14 N5 -59.1(4) . . . . ?
C12 N4 C15 C10 58.6(4) . . . . ?
C13 N4 C15 C10 -58.3(4) . . . . ?
N2 C10 C15 N4 -178.9(3) . . . . ?
C14 C10 C15 N4 58.2(4) . . . . ?
C11 C10 C15 N4 -59.2(3) . . . . ?
C11 N3 C16 N5 -60.9(4) . . . . ?
C12 N3 C16 N5 56.1(4) . . . . ?
C13 N5 C16 N3 -57.1(4) . . . . ?
C14 N5 C16 N3 60.9(4) . . . . ?

_refine_diff_density_max         0.834
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.076


_exptl_crystal_recrystallization_method 
'layering hexanes over its dichloromethane solution'
_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# 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_xsc1651_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1463775'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '[MnBr(CO)3(QTAm)]'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 Br Mn N5 O3'
_chemical_formula_weight         512.25

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'
Br Br -0.2901 2.4595 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.788(5)
_cell_length_b                   10.438(5)
_cell_length_c                   12.643(3)
_cell_angle_alpha                104.88(2)
_cell_angle_beta                 105.15(3)
_cell_angle_gamma                103.47(6)
_cell_volume                     1024.3(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2400
_cell_measurement_theta_min      5.076
_cell_measurement_theta_max      47.325

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    2.628
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5154
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7969
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.536
_diffrn_reflns_theta_max         24.681
_diffrn_reflns_theta_full        24.681
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             3366
_reflns_number_gt                2400
_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)+(0.1000P)²+0.7534P] 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         3366
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1550
_refine_ls_wR_factor_gt          0.1377
_refine_ls_goodness_of_fit_ref   0.895
_refine_ls_restrained_S_all      0.895
_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
Br1 Br 0.75388(7) 0.62800(6) 0.15178(5) 0.0513(3) Uani 1 1 d . . . . .
Mn1 Mn 0.68140(8) 0.76743(7) 0.31430(6) 0.0296(2) Uani 1 1 d . . . . .
N2 N 0.4350(4) 0.6813(4) 0.2012(3) 0.0255(8) Uani 1 1 d . . . . .
N1 N 0.6048(5) 0.5796(4) 0.3466(4) 0.0322(9) Uani 1 1 d . . . . .
O1 O 0.6241(6) 0.9255(5) 0.5181(4) 0.0624(12) Uani 1 1 d . . . . .
O2 O 1.0430(5) 0.8624(4) 0.4391(5) 0.0730(15) Uani 1 1 d . . . . .
O3 O 0.7916(6) 1.0267(5) 0.2647(4) 0.0716(14) Uani 1 1 d . . . . .
N3 N 0.3216(6) 0.8499(5) -0.0260(4) 0.0460(12) Uani 1 1 d . . . . .
N5 N 0.0642(5) 0.7272(5) -0.0032(4) 0.0443(11) Uani 1 1 d . . . . .
N4 N 0.2460(5) 0.9546(4) 0.1419(4) 0.0419(11) Uani 1 1 d . . . . .
C14 C 0.3375(5) 0.7472(5) 0.1314(4) 0.0275(10) Uani 1 1 d . . . . .
C15 C 0.1546(6) 0.6540(5) 0.0640(5) 0.0362(12) Uani 1 1 d . . . . .
H15A H 0.1511 0.5665 0.0114 0.043 Uiso 1 1 calc R U . . .
H15B H 0.1011 0.6325 0.1183 0.043 Uiso 1 1 calc R U . . .
C13 C 0.3739(6) 0.5531(5) 0.1890(4) 0.0342(12) Uani 1 1 d . . . . .
H13 H 0.2709 0.4990 0.1325 0.041 Uiso 1 1 calc R U . . .
C17 C 0.3357(6) 0.8843(5) 0.2117(5) 0.0347(12) Uani 1 1 d . . . . .
H17A H 0.2814 0.8647 0.2661 0.042 Uiso 1 1 calc R U . . .
H17B H 0.4490 0.9453 0.2560 0.042 Uiso 1 1 calc R U . . .
C4 C 0.4648(6) 0.4922(5) 0.2630(4) 0.0328(11) Uani 1 1 d . . . . .
C12 C 0.6876(6) 0.5321(5) 0.4289(5) 0.0362(12) Uani 1 1 d . . . . .
C16 C 0.4147(6) 0.7776(6) 0.0405(5) 0.0369(12) Uani 1 1 d . . . . .
H16A H 0.5303 0.8359 0.0794 0.044 Uiso 1 1 calc R U . . .
H16B H 0.4112 0.6904 -0.0125 0.044 Uiso 1 1 calc R U . . .
C18 C 0.3247(7) 0.9775(6) 0.0550(5) 0.0460(14) Uani 1 1 d . . . . .
H18A H 0.2680 1.0269 0.0115 0.055 Uiso 1 1 calc R U . . .
H18B H 0.4396 1.0368 0.0959 0.055 Uiso 1 1 calc R U . . .
C2 C 0.9007(7) 0.8200(5) 0.3932(5) 0.0454(14) Uani 1 1 d . . . . .
C1 C 0.6413(6) 0.8636(5) 0.4387(5) 0.0377(12) Uani 1 1 d . . . . .
C3 C 0.7422(6) 0.9245(6) 0.2793(5) 0.0438(14) Uani 1 1 d . . . . .
C7 C 0.6317(7) 0.3872(6) 0.4193(5) 0.0452(14) Uani 1 1 d . . . . .
C20 C 0.1489(7) 0.7574(7) -0.0839(5) 0.0552(16) Uani 1 1 d . . . . .
H20A H 0.0874 0.8004 -0.1317 0.066 Uiso 1 1 calc R U . . .
H20B H 0.1475 0.6699 -0.1351 0.066 Uiso 1 1 calc R U . . .
C19 C 0.0741(7) 0.8593(6) 0.0782(6) 0.0468(15) Uani 1 1 d . . . . .
H19A H 0.0228 0.8394 0.1340 0.056 Uiso 1 1 calc R U . . .
H19B H 0.0110 0.9060 0.0355 0.056 Uiso 1 1 calc R U . . .
C8 C 0.7223(9) 0.3414(8) 0.5029(7) 0.0633(19) Uani 1 1 d . . . . .
H8 H 0.6902 0.2470 0.4950 0.076 Uiso 1 1 calc R U . . .
C6 C 0.4885(8) 0.2972(6) 0.3256(6) 0.0564(17) Uani 1 1 d . . . . .
H6 H 0.4523 0.2022 0.3149 0.068 Uiso 1 1 calc R U . . .
C5 C 0.4028(7) 0.3494(6) 0.2505(6) 0.0517(16) Uani 1 1 d . . . . .
H5 H 0.3039 0.2915 0.1912 0.062 Uiso 1 1 calc R U . . .
C9 C 0.8564(9) 0.4332(9) 0.5951(6) 0.070(2) Uani 1 1 d . . . . .
H9 H 0.9143 0.4021 0.6506 0.084 Uiso 1 1 calc R U . . .
C11 C 0.8251(7) 0.6242(6) 0.5267(5) 0.0506(15) Uani 1 1 d . . . . .
H11 H 0.8605 0.7192 0.5373 0.061 Uiso 1 1 calc R U . . .
C10 C 0.9063(9) 0.5738(8) 0.6060(6) 0.0644(18) Uani 1 1 d . . . . .
H10 H 0.9982 0.6357 0.6694 0.077 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
Br1 Mn1 2.5152(12) . y
Mn1 C2 1.797(5) . y
Mn1 C1 1.802(6) . y
Mn1 C3 1.805(6) . y
Mn1 N2 2.087(4) . y
Mn1 N1 2.098(4) . y
N2 C13 1.272(6) . ?
N2 C14 1.475(6) . ?
N1 C4 1.329(6) . ?
N1 C12 1.377(6) . ?
O1 C1 1.113(7) . ?
O2 C2 1.152(6) . ?
O3 C3 1.135(7) . ?
N3 C18 1.446(8) . ?
N3 C20 1.464(7) . ?
N3 C16 1.483(7) . ?
N5 C19 1.462(8) . ?
N5 C20 1.465(8) . ?
N5 C15 1.484(6) . ?
N4 C19 1.474(7) . ?
N4 C17 1.476(7) . ?
N4 C18 1.482(7) . ?
C14 C17 1.533(7) . ?
C14 C16 1.542(7) . ?
C14 C15 1.544(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C13 C4 1.438(7) . ?
C13 H13 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C4 C5 1.413(7) . ?
C12 C11 1.407(8) . ?
C12 C7 1.440(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C7 C6 1.403(8) . ?
C7 C8 1.406(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C8 C9 1.359(10) . ?
C8 H8 0.9300 . ?
C6 C5 1.360(8) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C9 C10 1.389(10) . ?
C9 H9 0.9300 . ?
C11 C10 1.364(8) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Mn1 C1 92.5(3) . . y
C2 Mn1 C3 82.7(3) . . y
C1 Mn1 C3 90.7(3) . . y
C2 Mn1 N2 170.1(2) . . y
C1 Mn1 N2 97.1(2) . . y
C3 Mn1 N2 99.3(2) . . y
C2 Mn1 N1 98.9(2) . . y
C1 Mn1 N1 91.4(2) . . y
C3 Mn1 N1 177.3(2) . . y
N2 Mn1 N1 78.66(16) . . y
C2 Mn1 Br1 83.9(2) . . y
C1 Mn1 Br1 175.40(16) . . y
C3 Mn1 Br1 91.7(2) . . y
N2 Mn1 Br1 86.38(11) . . y
N1 Mn1 Br1 86.34(12) . . y
C13 N2 C14 120.0(4) . . ?
C13 N2 Mn1 111.8(3) . . ?
C14 N2 Mn1 128.0(3) . . ?
C4 N1 C12 118.9(4) . . ?
C4 N1 Mn1 110.8(3) . . ?
C12 N1 Mn1 129.6(3) . . ?
C18 N3 C20 108.9(5) . . ?
C18 N3 C16 108.6(4) . . ?
C20 N3 C16 107.5(4) . . ?
C19 N5 C20 108.9(5) . . ?
C19 N5 C15 108.3(4) . . ?
C20 N5 C15 107.8(4) . . ?
C19 N4 C17 107.6(4) . . ?
C19 N4 C18 108.0(4) . . ?
C17 N4 C18 109.2(4) . . ?
N2 C14 C17 109.6(4) . . ?
N2 C14 C16 110.1(4) . . ?
C17 C14 C16 109.6(4) . . ?
N2 C14 C15 113.0(4) . . ?
C17 C14 C15 107.5(4) . . ?
C16 C14 C15 107.0(4) . . ?
N5 C15 C14 110.0(4) . . ?
N5 C15 H15A 109.7 . . ?
C14 C15 H15A 109.7 . . ?
N5 C15 H15B 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N2 C13 C4 119.7(4) . . ?
N2 C13 H13 120.2 . . ?
C4 C13 H13 120.2 . . ?
N4 C17 C14 109.9(4) . . ?
N4 C17 H17A 109.7 . . ?
C14 C17 H17A 109.7 . . ?
N4 C17 H17B 109.7 . . ?
C14 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
N1 C4 C5 122.6(5) . . ?
N1 C4 C13 115.9(4) . . ?
C5 C4 C13 121.4(4) . . ?
N1 C12 C11 121.2(5) . . ?
N1 C12 C7 120.7(5) . . ?
C11 C12 C7 118.1(5) . . ?
N3 C16 C14 110.1(4) . . ?
N3 C16 H16A 109.6 . . ?
C14 C16 H16A 109.6 . . ?
N3 C16 H16B 109.6 . . ?
C14 C16 H16B 109.6 . . ?
H16A C16 H16B 108.2 . . ?
N3 C18 N4 113.9(4) . . ?
N3 C18 H18A 108.8 . . ?
N4 C18 H18A 108.8 . . ?
N3 C18 H18B 108.8 . . ?
N4 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
O2 C2 Mn1 174.0(5) . . ?
O1 C1 Mn1 176.9(5) . . ?
O3 C3 Mn1 174.6(5) . . ?
C6 C7 C8 122.8(6) . . ?
C6 C7 C12 118.1(5) . . ?
C8 C7 C12 119.2(6) . . ?
N5 C20 N3 113.7(5) . . ?
N5 C20 H20A 108.8 . . ?
N3 C20 H20A 108.8 . . ?
N5 C20 H20B 108.8 . . ?
N3 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
N5 C19 N4 113.3(4) . . ?
N5 C19 H19A 108.9 . . ?
N4 C19 H19A 108.9 . . ?
N5 C19 H19B 108.9 . . ?
N4 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C9 C8 C7 120.9(6) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C5 C6 C7 119.8(5) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C5 C4 119.7(5) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C8 C9 C10 119.6(6) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C10 C11 C12 119.9(6) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C10 C9 122.2(7) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?

_refine_diff_density_max         0.554
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.130

