# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_111
_audit_block_doi                 10.5517/ccdc.csd.cc1q91pr
_database_code_depnum_ccdc_archive 'CCDC 1587624'
_audit_update_record             
;
2017-11-26 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;
_audit_creation_date             2017-11-22
_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         'C16 H26 Mn N4 Si2'
_chemical_formula_sum            'C16 H26 Mn N4 Si2'
_chemical_formula_weight         385.53
_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'
Si Si 0.0817 0.0704 '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                   28.787(2)
_cell_length_b                   8.9631(7)
_cell_length_c                   21.4722(15)
_cell_angle_alpha                90
_cell_angle_beta                 131.572(2)
_cell_angle_gamma                90
_cell_volume                     4144.8(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4879
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.785
_cell_measurement_theta_min      2.462
_shelx_estimated_absorpt_T_max   0.915
_shelx_estimated_absorpt_T_min   0.794
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0685 before and 0.0609 after correction.
The Ratio of minimum to maximum transmission is 0.9126.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20657
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.461
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                2453
_reflns_number_total             3622
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.949
_refine_diff_density_min         -0.924
_refine_diff_density_rms         0.138
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3622
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1242
_refine_ls_R_factor_gt           0.0840
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1730P)²+26.9280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2449
_refine_ls_wR_factor_ref         0.2868
_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. Uiso/Uaniso restraints and constraints
Uanis(C1A) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C1B) \\sim Ueq, Uanis(C1A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C1A) = Uanis(C1B)
3. Others
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=1-FVAR(1)
 Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C8(H8), C9(H9), C10(H10), C6(H6), C7(H7), C11(H11)
4.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C14(H14A,H14B,H14C), C1A(H1AA,H1AB,H1AC), C3(H3A,H3B,
 H3C), C15(H15A,H15B,H15C), C2(H2A,H2B,H2C), C1B(H1BA,H1BB,H1BC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.43452(5) 0.33599(12) 0.22378(6) 0.0424(4) Uani 1 1 d . . . . .
Si1 Si 0.48086(8) 0.1647(2) 0.09919(13) 0.0442(6) Uani 1 1 d . . . . .
Si2 Si 0.32516(9) 0.5222(2) 0.23485(11) 0.0431(6) Uani 1 1 d . . . . .
N1 N 0.4808(2) 0.3060(6) 0.1546(3) 0.0285(12) Uani 1 1 d . . . . .
N4 N 0.3533(2) 0.3877(6) 0.2108(3) 0.0357(13) Uani 1 1 d . . . . .
N2 N 0.4295(2) 0.5056(5) 0.1516(3) 0.0273(11) Uani 1 1 d . . . . .
N3 N 0.3586(2) 0.1842(6) 0.1524(3) 0.0336(12) Uani 1 1 d . . . . .
C4 C 0.4504(3) 0.4380(7) 0.1184(3) 0.0274(13) Uani 1 1 d . . . . .
C13 C 0.3228(3) 0.2700(7) 0.1598(4) 0.0321(14) Uani 1 1 d . . . . .
C5 C 0.4373(3) 0.5088(9) 0.0485(4) 0.0421(17) Uani 1 1 d . . . . .
H5 H 0.451139 0.464427 0.023172 0.051 Uiso 1 1 calc R . . . .
C12 C 0.2604(3) 0.2269(9) 0.1148(4) 0.0414(17) Uani 1 1 d . . . . .
H12 H 0.234974 0.284512 0.119221 0.050 Uiso 1 1 calc R . . . .
C8 C 0.3980(3) 0.6352(7) 0.1208(4) 0.0398(16) Uani 1 1 d . . . . .
H8 H 0.384450 0.679641 0.146495 0.048 Uiso 1 1 calc R . . . .
C16 C 0.2920(4) 0.4431(12) 0.2791(6) 0.071(3) Uani 1 1 d . . . . .
H16A H 0.253218 0.390584 0.235189 0.106 Uiso 1 1 calc GR . . . .
H16B H 0.283777 0.524139 0.301200 0.106 Uiso 1 1 calc GR . . . .
H16C H 0.321803 0.373059 0.323939 0.106 Uiso 1 1 calc GR . . . .
C14 C 0.2625(4) 0.6363(9) 0.1413(5) 0.054(2) Uani 1 1 d . . . . .
H14A H 0.278912 0.684100 0.118390 0.082 Uiso 1 1 calc GR . . . .
H14B H 0.248103 0.713018 0.157721 0.082 Uiso 1 1 calc GR . . . .
H14C H 0.227632 0.571306 0.099088 0.082 Uiso 1 1 calc GR . . . .
C1A C 0.5412(17) 0.172(5) 0.098(3) 0.043(4) Uani 0.35(4) 1 d . U P A 2
H1AA H 0.535112 0.258768 0.064965 0.065 Uiso 0.35(4) 1 calc GR . P A 2
H1AB H 0.540795 0.080813 0.072085 0.065 Uiso 0.35(4) 1 calc GR . P A 2
H1AC H 0.581143 0.180925 0.154571 0.065 Uiso 0.35(4) 1 calc GR . P A 2
C3 C 0.4007(3) 0.1323(9) -0.0046(4) 0.0484(19) Uani 1 1 d . . . . .
H3A H 0.371643 0.113968 0.003839 0.073 Uiso 1 1 calc GR . . . .
H3B H 0.401403 0.045541 -0.031719 0.073 Uiso 1 1 calc GR . . . .
H3C H 0.387395 0.220574 -0.039809 0.073 Uiso 1 1 calc GR . . . .
C9 C 0.3341(3) 0.0622(9) 0.1033(4) 0.0471(18) Uani 1 1 d . . . . .
H9 H 0.359773 0.003631 0.099711 0.057 Uiso 1 1 calc R . . . .
C10 C 0.2732(4) 0.0190(10) 0.0580(5) 0.0511(19) Uani 1 1 d . . . . .
H10 H 0.256591 -0.066063 0.022775 0.061 Uiso 1 1 calc R . . . .
C15 C 0.3919(4) 0.6444(10) 0.3138(6) 0.071(3) Uani 1 1 d . . . . .
H15A H 0.421937 0.588416 0.365642 0.107 Uiso 1 1 calc GR . . . .
H15B H 0.377188 0.730916 0.324396 0.107 Uiso 1 1 calc GR . . . .
H15C H 0.411932 0.678455 0.293168 0.107 Uiso 1 1 calc GR . . . .
C6 C 0.4045(4) 0.6414(9) 0.0175(4) 0.050(2) Uani 1 1 d . . . . .
H6 H 0.395749 0.687260 -0.029151 0.060 Uiso 1 1 calc R . . . .
C7 C 0.3846(4) 0.7064(8) 0.0536(5) 0.0515(19) Uani 1 1 d . . . . .
H7 H 0.362276 0.797770 0.033084 0.062 Uiso 1 1 calc R . . . .
C2 C 0.5071(4) -0.0074(9) 0.1638(6) 0.077(3) Uani 1 1 d . U . . .
H2A H 0.549498 0.007072 0.216922 0.115 Uiso 1 1 calc GR . . . .
H2B H 0.506242 -0.091977 0.134134 0.115 Uiso 1 1 calc GR . . . .
H2C H 0.479306 -0.027545 0.174215 0.115 Uiso 1 1 calc GR . . . .
C11 C 0.2368(3) 0.1047(10) 0.0659(5) 0.054(2) Uani 1 1 d . . . . .
H11 H 0.194987 0.076631 0.036455 0.064 Uiso 1 1 calc R . . . .
C1B C 0.5307(9) 0.217(3) 0.0708(15) 0.043(4) Uani 0.65(4) 1 d . U P A 1
H1BA H 0.512391 0.304587 0.033899 0.065 Uiso 0.65(4) 1 calc GR . P A 1
H1BB H 0.531503 0.133252 0.042405 0.065 Uiso 0.65(4) 1 calc GR . P A 1
H1BC H 0.573112 0.241044 0.121713 0.065 Uiso 0.65(4) 1 calc GR . 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
Mn1 Mn1 3.138(2) 2_655 ?
Mn1 N1 2.094(5) 2_655 ?
Mn1 N4 2.212(5) . ?
Mn1 N2 2.106(5) . ?
Mn1 N3 2.129(5) . ?
Mn1 C13 2.592(6) . ?
Si1 N1 1.738(5) . ?
Si1 C1A 1.76(3) . ?
Si1 C3 1.884(7) . ?
Si1 C2 1.866(9) . ?
Si1 C1B 1.95(2) . ?
Si2 N4 1.712(6) . ?
Si2 C16 1.875(9) . ?
Si2 C14 1.878(8) . ?
Si2 C15 1.856(8) . ?
N1 C4 1.366(8) . ?
N4 C13 1.345(8) . ?
N2 C4 1.346(8) . ?
N2 C8 1.347(8) . ?
N3 C13 1.377(8) . ?
N3 C9 1.348(9) . ?
C4 C5 1.429(9) . ?
C13 C12 1.416(9) . ?
C5 C6 1.383(11) . ?
C12 C11 1.348(11) . ?
C8 C7 1.378(10) . ?
C9 C10 1.382(10) . ?
C10 C11 1.396(12) . ?
C6 C7 1.361(11) . ?

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 Mn1 54.93(14) 2_655 2_655 ?
N1 Mn1 N4 116.24(19) 2_655 . ?
N1 Mn1 N2 117.71(19) 2_655 . ?
N1 Mn1 N3 127.2(2) 2_655 . ?
N1 Mn1 C13 129.79(19) 2_655 . ?
N4 Mn1 Mn1 164.32(15) . 2_655 ?
N4 Mn1 C13 31.3(2) . . ?
N2 Mn1 Mn1 75.14(13) . 2_655 ?
N2 Mn1 N4 101.86(19) . . ?
N2 Mn1 N3 113.27(19) . . ?
N2 Mn1 C13 108.63(19) . . ?
N3 Mn1 Mn1 132.33(15) . 2_655 ?
N3 Mn1 N4 63.2(2) . . ?
N3 Mn1 C13 32.0(2) . . ?
C13 Mn1 Mn1 164.36(15) . 2_655 ?
N1 Si1 C1A 115.8(12) . . ?
N1 Si1 C3 111.4(3) . . ?
N1 Si1 C2 106.1(4) . . ?
N1 Si1 C1B 111.8(6) . . ?
C1A Si1 C3 115.6(13) . . ?
C1A Si1 C2 97.4(16) . . ?
C3 Si1 C1B 104.2(7) . . ?
C2 Si1 C3 109.0(4) . . ?
C2 Si1 C1B 114.4(9) . . ?
N4 Si2 C16 112.8(4) . . ?
N4 Si2 C14 111.9(3) . . ?
N4 Si2 C15 106.3(4) . . ?
C16 Si2 C14 107.2(4) . . ?
C15 Si2 C16 109.1(5) . . ?
C15 Si2 C14 109.5(4) . . ?
Si1 N1 Mn1 114.7(2) . 2_655 ?
C4 N1 Mn1 112.0(4) . 2_655 ?
C4 N1 Si1 122.1(4) . . ?
Si2 N4 Mn1 141.4(3) . . ?
C13 N4 Mn1 90.2(4) . . ?
C13 N4 Si2 127.9(5) . . ?
C4 N2 Mn1 103.2(4) . . ?
C4 N2 C8 121.3(5) . . ?
C8 N2 Mn1 132.9(4) . . ?
C13 N3 Mn1 92.8(4) . . ?
C9 N3 Mn1 146.7(5) . . ?
C9 N3 C13 120.0(6) . . ?
N1 C4 C5 127.3(6) . . ?
N2 C4 N1 115.5(5) . . ?
N2 C4 C5 117.2(6) . . ?
N4 C13 Mn1 58.6(3) . . ?
N4 C13 N3 113.4(5) . . ?
N4 C13 C12 128.1(6) . . ?
N3 C13 Mn1 55.1(3) . . ?
N3 C13 C12 118.5(6) . . ?
C12 C13 Mn1 171.9(5) . . ?
C6 C5 C4 120.5(7) . . ?
C11 C12 C13 120.5(7) . . ?
N2 C8 C7 123.0(7) . . ?
N3 C9 C10 122.5(7) . . ?
C9 C10 C11 117.7(7) . . ?
C7 C6 C5 120.3(7) . . ?
C6 C7 C8 117.8(7) . . ?
C12 C11 C10 120.7(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
