# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mk392
_database_code_depnum_ccdc_archive 'CCDC 1537631'
_audit_update_record             
;
2017-03-13 deposited with the CCDC.
2017-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 Cl Mg N3 O, 2(C H2 Cl2)'
_chemical_formula_sum            'C21 H22 Cl5 Mg N3 O'
_chemical_formula_weight         533.97

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'
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'
Mg Mg 0.0486 0.0363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   24.0022(18)
_cell_length_b                   8.6136(6)
_cell_length_c                   25.556(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.047(3)
_cell_angle_gamma                90
_cell_volume                     4746.9(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    3904
_cell_measurement_theta_min      1.77
_cell_measurement_theta_max      26.20

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             2192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.658
_shelx_estimated_absorpt_T_min   0.817
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_process_details   'Sadabs, Bruker-AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS micro-focus'
_diffrn_measurement_device_type  'ApexDuo, Bruker-AXS'
_diffrn_measurement_method       '1 deg. φ and ω scans'
_diffrn_detector_area_resol_mean 1.75
_diffrn_reflns_number            16678
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.774
_diffrn_reflns_theta_max         26.206
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4733
_reflns_number_gt                3904
_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       'Apex2, Bruker-AXS'
_computing_cell_refinement       'Saint, Bruker-AXS'
_computing_data_reduction        'Saint, Bruker-AXS'
_computing_structure_solution    'SHELXT-2014 (sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0395P)²+12.0103P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4733
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0912
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
Mg1 Mg 0.44241(3) 0.54591(8) 0.44039(3) 0.01098(17) Uani 1 1 d . . . . .
Cl1 Cl 0.44920(2) 0.81488(6) 0.41406(3) 0.01621(14) Uani 1 1 d . . . . .
O1 O 0.53434(7) 0.49465(17) 0.47301(7) 0.0109(3) Uani 1 1 d . . . . .
N1 N 0.61044(8) 0.6863(2) 0.57737(8) 0.0124(4) Uani 1 1 d . . . . .
N2 N 0.57398(8) 0.5360(2) 0.64923(8) 0.0134(4) Uani 1 1 d . . . . .
N3 N 0.65282(8) 0.3930(2) 0.57248(8) 0.0129(4) Uani 1 1 d . . . . .
C4 C 0.57700(10) 0.5417(3) 0.45567(10) 0.0120(5) Uani 1 1 d . . . . .
C5 C 0.61489(10) 0.6716(3) 0.48170(10) 0.0132(5) Uani 1 1 d . . . . .
C6 C 0.69618(10) 0.5042(3) 0.59338(10) 0.0133(5) Uani 1 1 d . . . . .
C7 C 0.58591(10) 0.4606(3) 0.41251(10) 0.0149(5) Uani 1 1 d . . . . .
H7 H 0.5595 0.3759 0.3932 0.018 Uiso 1 1 calc R U . . .
C8 C 0.67674(10) 0.6505(3) 0.61325(10) 0.0141(5) Uani 1 1 d . . . . .
H8A H 0.6845 0.6385 0.6544 0.017 Uiso 1 1 calc R U . . .
H8B H 0.7022 0.7383 0.6111 0.017 Uiso 1 1 calc R U . . .
C9 C 0.66172(10) 0.7114(3) 0.46588(10) 0.0160(5) Uani 1 1 d . . . . .
H9 H 0.6875 0.7982 0.4839 0.019 Uiso 1 1 calc R U . . .
C10 C 0.60178(10) 0.7699(3) 0.52355(10) 0.0138(5) Uani 1 1 d . . . . .
H10A H 0.6295 0.8615 0.5344 0.017 Uiso 1 1 calc R U . . .
H10B H 0.5585 0.8080 0.5037 0.017 Uiso 1 1 calc R U . . .
C11 C 0.58656(11) 0.7835(3) 0.61040(11) 0.0158(5) Uani 1 1 d . . . . .
H11A H 0.5455 0.8258 0.5836 0.019 Uiso 1 1 calc R U . . .
H11B H 0.6150 0.8720 0.6280 0.019 Uiso 1 1 calc R U . . .
C12 C 0.66708(11) 0.2599(3) 0.55387(10) 0.0159(5) Uani 1 1 d . . . . .
H12 H 0.6360 0.1822 0.5379 0.019 Uiso 1 1 calc R U . . .
C13 C 0.63322(11) 0.5029(3) 0.39770(11) 0.0181(5) Uani 1 1 d . . . . .
H13 H 0.6392 0.4455 0.3688 0.022 Uiso 1 1 calc R U . . .
C14 C 0.58066(10) 0.6910(3) 0.65756(10) 0.0154(5) Uani 1 1 d . . . . .
C15 C 0.56786(10) 0.4503(3) 0.69021(10) 0.0176(5) Uani 1 1 d . . . . .
H15 H 0.5640 0.3410 0.6851 0.021 Uiso 1 1 calc R U . . .
C16 C 0.72509(12) 0.2312(3) 0.55693(11) 0.0212(5) Uani 1 1 d . . . . .
H16 H 0.7338 0.1355 0.5436 0.025 Uiso 1 1 calc R U . . .
C17 C 0.67139(11) 0.6269(3) 0.42438(11) 0.0186(5) Uani 1 1 d . . . . .
H17 H 0.7039 0.6543 0.4145 0.022 Uiso 1 1 calc R U . . .
C18 C 0.75568(11) 0.4832(3) 0.59814(11) 0.0180(5) Uani 1 1 d . . . . .
H18 H 0.7859 0.5629 0.6138 0.022 Uiso 1 1 calc R U . . .
C19 C 0.58012(11) 0.7620(3) 0.70598(11) 0.0209(5) Uani 1 1 d . . . . .
H19 H 0.5847 0.8714 0.7106 0.025 Uiso 1 1 calc R U . . .
C20 C 0.56696(11) 0.5134(3) 0.73941(11) 0.0228(6) Uani 1 1 d . . . . .
H20 H 0.5624 0.4488 0.7674 0.027 Uiso 1 1 calc R U . . .
C21 C 0.77021(11) 0.3449(3) 0.57981(12) 0.0231(6) Uani 1 1 d . . . . .
H21 H 0.8106 0.3278 0.5828 0.028 Uiso 1 1 calc R U . . .
C22 C 0.57282(12) 0.6732(3) 0.74730(11) 0.0254(6) Uani 1 1 d . . . . .
H22 H 0.5718 0.7201 0.7805 0.030 Uiso 1 1 calc R U . . .
C23 C 0.54358(12) 0.8962(3) 0.35175(12) 0.0223(6) Uani 1 1 d . . . . .
H23A H 0.4980 0.9039 0.3289 0.027 Uiso 1 1 calc R U . . .
H23B H 0.5530 0.7966 0.3733 0.027 Uiso 1 1 calc R U . . .
Cl2 Cl 0.57904(3) 0.89901(9) 0.30376(3) 0.03279(18) Uani 1 1 d . . . . .
Cl3 Cl 0.57046(3) 1.05162(8) 0.40168(3) 0.03264(18) Uani 1 1 d . . . . .
C24 C 0.70816(13) 0.8235(3) 0.20046(12) 0.0297(6) Uani 1 1 d . . . . .
H24A H 0.6718 0.8207 0.1618 0.036 Uiso 1 1 calc R U . . .
H24B H 0.7272 0.7189 0.2086 0.036 Uiso 1 1 calc R U . . .
Cl4 Cl 0.68385(3) 0.87219(11) 0.25405(3) 0.0414(2) Uani 1 1 d . . . . .
Cl5 Cl 0.76260(4) 0.96084(11) 0.19955(4) 0.0499(2) 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
Mg1 O1 2.0355(16) . ?
Mg1 O1 2.0609(17) 5_666 ?
Mg1 N3 2.2248(19) 5_666 ?
Mg1 N2 2.260(2) 5_666 ?
Mg1 N1 2.305(2) 5_666 ?
Mg1 Cl1 2.4379(9) . ?
Mg1 Mg1 3.1867(15) 5_666 ?
O1 C4 1.345(3) . ?
O1 Mg1 2.0609(17) 5_666 ?
N1 C11 1.472(3) . ?
N1 C8 1.479(3) . ?
N1 C10 1.484(3) . ?
N1 Mg1 2.304(2) 5_666 ?
N2 C15 1.341(3) . ?
N2 C14 1.350(3) . ?
N2 Mg1 2.260(2) 5_666 ?
N3 C6 1.341(3) . ?
N3 C12 1.342(3) . ?
N3 Mg1 2.2247(19) 5_666 ?
C4 C7 1.399(3) . ?
C4 C5 1.410(3) . ?
C5 C9 1.394(3) . ?
C5 C10 1.502(3) . ?
C6 C18 1.391(3) . ?
C6 C8 1.507(3) . ?
C7 C13 1.394(3) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C17 1.387(3) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C14 1.503(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C16 1.382(3) . ?
C12 H12 0.9500 . ?
C13 C17 1.377(4) . ?
C13 H13 0.9500 . ?
C14 C19 1.386(3) . ?
C15 C20 1.379(3) . ?
C15 H15 0.9500 . ?
C16 C21 1.384(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C21 1.380(4) . ?
C18 H18 0.9500 . ?
C19 C22 1.376(4) . ?
C19 H19 0.9500 . ?
C20 C22 1.389(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 Cl3 1.765(3) . ?
C23 Cl2 1.773(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 Cl4 1.759(3) . ?
C24 Cl5 1.770(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

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
O1 Mg1 O1 77.86(7) . 5_666 ?
O1 Mg1 N3 166.03(8) . 5_666 ?
O1 Mg1 N3 88.56(7) 5_666 5_666 ?
O1 Mg1 N2 91.28(7) . 5_666 ?
O1 Mg1 N2 151.64(7) 5_666 5_666 ?
N3 Mg1 N2 102.34(7) 5_666 5_666 ?
O1 Mg1 N1 107.24(7) . 5_666 ?
O1 Mg1 N1 86.01(7) 5_666 5_666 ?
N3 Mg1 N1 74.64(7) 5_666 5_666 ?
N2 Mg1 N1 72.15(7) 5_666 5_666 ?
O1 Mg1 Cl1 97.32(5) . . ?
O1 Mg1 Cl1 115.98(5) 5_666 . ?
N3 Mg1 Cl1 85.60(6) 5_666 . ?
N2 Mg1 Cl1 91.15(6) 5_666 . ?
N1 Mg1 Cl1 150.26(6) 5_666 . ?
O1 Mg1 Mg1 39.22(5) . 5_666 ?
O1 Mg1 Mg1 38.64(4) 5_666 5_666 ?
N3 Mg1 Mg1 127.13(6) 5_666 5_666 ?
N2 Mg1 Mg1 125.69(6) 5_666 5_666 ?
N1 Mg1 Mg1 98.30(6) 5_666 5_666 ?
Cl1 Mg1 Mg1 111.39(4) . 5_666 ?
C4 O1 Mg1 130.16(14) . . ?
C4 O1 Mg1 121.25(13) . 5_666 ?
Mg1 O1 Mg1 102.14(7) . 5_666 ?
C11 N1 C8 110.31(18) . . ?
C11 N1 C10 108.91(17) . . ?
C8 N1 C10 110.53(17) . . ?
C11 N1 Mg1 106.70(13) . 5_666 ?
C8 N1 Mg1 106.88(13) . 5_666 ?
C10 N1 Mg1 113.43(14) . 5_666 ?
C15 N2 C14 117.8(2) . . ?
C15 N2 Mg1 126.13(16) . 5_666 ?
C14 N2 Mg1 115.12(15) . 5_666 ?
C6 N3 C12 118.52(19) . . ?
C6 N3 Mg1 117.21(15) . 5_666 ?
C12 N3 Mg1 123.71(16) . 5_666 ?
O1 C4 C7 120.7(2) . . ?
O1 C4 C5 120.7(2) . . ?
C7 C4 C5 118.6(2) . . ?
C9 C5 C4 119.6(2) . . ?
C9 C5 C10 121.0(2) . . ?
C4 C5 C10 119.34(19) . . ?
N3 C6 C18 122.0(2) . . ?
N3 C6 C8 115.50(19) . . ?
C18 C6 C8 122.5(2) . . ?
C13 C7 C4 120.5(2) . . ?
C13 C7 H7 119.7 . . ?
C4 C7 H7 119.7 . . ?
N1 C8 C6 111.94(18) . . ?
N1 C8 H8A 109.2 . . ?
C6 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C6 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C17 C9 C5 121.3(2) . . ?
C17 C9 H9 119.4 . . ?
C5 C9 H9 119.4 . . ?
N1 C10 C5 113.48(18) . . ?
N1 C10 H10A 108.9 . . ?
C5 C10 H10A 108.9 . . ?
N1 C10 H10B 108.9 . . ?
C5 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N1 C11 C14 110.84(19) . . ?
N1 C11 H11A 109.5 . . ?
C14 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
C14 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
N3 C12 C16 122.7(2) . . ?
N3 C12 H12 118.7 . . ?
C16 C12 H12 118.7 . . ?
C17 C13 C7 120.8(2) . . ?
C17 C13 H13 119.6 . . ?
C7 C13 H13 119.6 . . ?
N2 C14 C19 122.0(2) . . ?
N2 C14 C11 116.4(2) . . ?
C19 C14 C11 121.5(2) . . ?
N2 C15 C20 123.1(2) . . ?
N2 C15 H15 118.4 . . ?
C20 C15 H15 118.4 . . ?
C12 C16 C21 118.6(2) . . ?
C12 C16 H16 120.7 . . ?
C21 C16 H16 120.7 . . ?
C13 C17 C9 119.2(2) . . ?
C13 C17 H17 120.4 . . ?
C9 C17 H17 120.4 . . ?
C21 C18 C6 119.1(2) . . ?
C21 C18 H18 120.5 . . ?
C6 C18 H18 120.5 . . ?
C22 C19 C14 119.6(2) . . ?
C22 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?
C15 C20 C22 118.8(2) . . ?
C15 C20 H20 120.6 . . ?
C22 C20 H20 120.6 . . ?
C18 C21 C16 119.1(2) . . ?
C18 C21 H21 120.4 . . ?
C16 C21 H21 120.4 . . ?
C19 C22 C20 118.6(2) . . ?
C19 C22 H22 120.7 . . ?
C20 C22 H22 120.7 . . ?
Cl3 C23 Cl2 110.84(13) . . ?
Cl3 C23 H23A 109.5 . . ?
Cl2 C23 H23A 109.5 . . ?
Cl3 C23 H23B 109.5 . . ?
Cl2 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
Cl4 C24 Cl5 110.49(15) . . ?
Cl4 C24 H24A 109.6 . . ?
Cl5 C24 H24A 109.6 . . ?
Cl4 C24 H24B 109.6 . . ?
Cl5 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?

_refine_diff_density_max         0.766
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_mk395
_database_code_depnum_ccdc_archive 'CCDC 1537632'
_audit_update_record             
;
2017-03-13 deposited with the CCDC.
2017-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H44 Cl2 Mg2 N6 O2, 5(C H2 Cl2)'
_chemical_formula_sum            'C47 H54 Cl12 Mg2 N6 O2'
_chemical_formula_weight         1208.98

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'
Mg Mg 0.0486 0.0363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   27.2980(18)
_cell_length_b                   14.9001(12)
_cell_length_c                   16.8775(10)
_cell_angle_alpha                90
_cell_angle_beta                 124.630(2)
_cell_angle_gamma                90
_cell_volume                     5648.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4116
_cell_measurement_theta_min      1.64
_cell_measurement_theta_max      25.12

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             2488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.653
_shelx_estimated_absorpt_T_min   0.804
_shelx_estimated_absorpt_T_max   0.859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_T_max  0.859
_exptl_absorpt_process_details   'Sadabs, Bruker-AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS micro-focus'
_diffrn_measurement_device_type  'ApexDuo, Bruker-AXS'
_diffrn_measurement_method       '1 deg. ω and φ scans'
_diffrn_detector_area_resol_mean 1.75
_diffrn_reflns_number            19575
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.640
_diffrn_reflns_theta_max         25.118
_diffrn_reflns_theta_full        25.118
_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             5026
_reflns_number_gt                4116
_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       'Apex2, Bruker-AXS'
_computing_cell_refinement       'Saint, Bruker-AXS'
_computing_data_reduction        'Saint, Bruker-AXS'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0752P)²+32.6172P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5026
_refine_ls_number_parameters     314
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1604
_refine_ls_wR_factor_gt          0.1488
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.046
_refine_ls_shift/su_mean         0.002

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
Mg1 Mg 0.56742(4) 0.46691(7) 0.55850(7) 0.0155(2) Uani 1 1 d . . . . .
Cl1 Cl 0.61502(3) 0.53014(5) 0.48469(5) 0.0205(2) Uani 1 1 d . . . . .
Cl2 Cl 0.79214(5) 0.52039(9) 0.65398(9) 0.0520(3) Uani 1 1 d . . . . .
Cl3 Cl 0.77333(6) 0.32714(9) 0.61839(10) 0.0576(3) Uani 1 1 d . . . . .
Cl4 Cl 0.72693(6) 0.78177(12) 0.65243(10) 0.0714(4) Uani 1 1 d . . . . .
Cl5 Cl 0.67024(9) 0.81388(13) 0.44936(12) 0.0884(5) Uani 1 1 d . . . . .
Cl6 Cl 0.93556(7) 0.49486(12) 0.70155(11) 0.0758(5) Uani 1 1 d . . . . .
O1 O 0.48360(9) 0.42219(14) 0.46135(15) 0.0163(5) Uani 1 1 d . . . . .
N1 N 0.60295(11) 0.33282(18) 0.54521(19) 0.0184(6) Uani 1 1 d . . . . .
N2 N 0.56852(11) 0.37097(18) 0.66814(18) 0.0183(6) Uani 1 1 d . . . . .
N3 N 0.64277(12) 0.50980(19) 0.70433(19) 0.0204(6) Uani 1 1 d . . . . .
C1 C 0.61353(15) 0.2242(2) 0.4517(3) 0.0258(8) Uani 1 1 d . . . . .
H1 H 0.6161 0.2115 0.3989 0.031 Uiso 1 1 calc R U . . .
C2 C 0.64453(15) 0.4778(2) 0.7805(2) 0.0222(7) Uani 1 1 d . . . . .
C3 C 0.59200(15) 0.4221(2) 0.7573(2) 0.0227(7) Uani 1 1 d . . . . .
H3A H 0.6042 0.3801 0.8110 0.027 Uiso 1 1 calc R U . . .
H3B H 0.5605 0.4617 0.7496 0.027 Uiso 1 1 calc R U . . .
C4 C 0.60749(13) 0.2659(2) 0.6029(2) 0.0204(7) Uani 1 1 d . . . . .
C5 C 0.46913(14) 0.3348(2) 0.4555(2) 0.0188(7) Uani 1 1 d . . . . .
C6 C 0.47940(14) 0.2892(2) 0.5371(2) 0.0203(7) Uani 1 1 d . . . . .
C7 C 0.60838(14) 0.2944(2) 0.6886(2) 0.0221(7) Uani 1 1 d . . . . .
H7A H 0.5963 0.2430 0.7112 0.027 Uiso 1 1 calc R U . . .
H7B H 0.6496 0.3111 0.7413 0.027 Uiso 1 1 calc R U . . .
C8 C 0.44622(14) 0.2856(2) 0.3704(2) 0.0224(7) Uani 1 1 d . . . . .
C9 C 0.60562(14) 0.3107(2) 0.4707(2) 0.0219(7) Uani 1 1 d . . . . .
H9 H 0.6019 0.3571 0.4290 0.026 Uiso 1 1 calc R U . . .
C10 C 0.50747(14) 0.3387(2) 0.6310(2) 0.0219(7) Uani 1 1 d . . . . .
H10A H 0.4822 0.3907 0.6219 0.026 Uiso 1 1 calc R U . . .
H10B H 0.5093 0.2985 0.6793 0.026 Uiso 1 1 calc R U . . .
C11 C 0.61461(16) 0.1774(2) 0.5874(3) 0.0273(8) Uani 1 1 d . . . . .
H11 H 0.6173 0.1317 0.6289 0.033 Uiso 1 1 calc R U . . .
C12 C 0.69039(16) 0.4987(3) 0.8744(3) 0.0331(9) Uani 1 1 d . . . . .
H12 H 0.6912 0.4740 0.9270 0.040 Uiso 1 1 calc R U . . .
C13 C 0.46375(15) 0.1997(2) 0.5303(3) 0.0276(8) Uani 1 1 d . . . . .
H13 H 0.4709 0.1701 0.5858 0.033 Uiso 1 1 calc R U . . .
C14 C 0.61774(16) 0.1559(2) 0.5107(3) 0.0295(8) Uani 1 1 d . . . . .
H14 H 0.6227 0.0954 0.4988 0.035 Uiso 1 1 calc R U . . .
C15 C 0.68581(15) 0.5663(3) 0.7211(3) 0.0278(8) Uani 1 1 d . . . . .
H15 H 0.6845 0.5899 0.6676 0.033 Uiso 1 1 calc R U . . .
C16 C 0.43996(17) 0.3286(3) 0.2843(3) 0.0296(8) Uani 1 1 d . . . . .
H16A H 0.4531 0.2865 0.2555 0.044 Uiso 1 1 calc R U . . .
H16B H 0.4645 0.3830 0.3047 0.044 Uiso 1 1 calc R U . . .
H16C H 0.3982 0.3445 0.2368 0.044 Uiso 1 1 calc R U . . .
C17 C 0.43805(17) 0.1519(2) 0.4451(3) 0.0330(9) Uani 1 1 d . . . . .
C18 C 0.43043(16) 0.1960(2) 0.3667(3) 0.0295(8) Uani 1 1 d . . . . .
H18 H 0.4138 0.1639 0.3081 0.035 Uiso 1 1 calc R U . . .
C19 C 0.73184(18) 0.5916(3) 0.8121(3) 0.0395(10) Uani 1 1 d . . . . .
H19 H 0.7612 0.6328 0.8212 0.047 Uiso 1 1 calc R U . . .
C20 C 0.73470(18) 0.5559(3) 0.8902(3) 0.0439(11) Uani 1 1 d . . . . .
H20 H 0.7668 0.5706 0.9540 0.053 Uiso 1 1 calc R U . . .
C21 C 0.4191(2) 0.0558(3) 0.4379(3) 0.0491(12) Uani 1 1 d . . . . .
H21A H 0.3793 0.0538 0.4252 0.074 Uiso 1 1 calc R U . . .
H21B H 0.4474 0.0248 0.4986 0.074 Uiso 1 1 calc R U . . .
H21C H 0.4182 0.0261 0.3852 0.074 Uiso 1 1 calc R U . . .
C22 C 0.75552(19) 0.4242(3) 0.6561(3) 0.0438(11) Uani 1 1 d . . . . .
H22A H 0.7665 0.4149 0.7223 0.053 Uiso 1 1 calc R U . . .
H22B H 0.7120 0.4341 0.6136 0.053 Uiso 1 1 calc R U . . .
C23 C 0.68168(19) 0.7393(3) 0.5373(3) 0.0420(10) Uani 1 1 d . . . . .
H23A H 0.6427 0.7231 0.5248 0.050 Uiso 1 1 calc R U . . .
H23B H 0.6998 0.6837 0.5328 0.050 Uiso 1 1 calc R U . . .
C24 C 1.0000 0.4315(6) 0.7500 0.071(2) Uani 1 2 d S T P . .
H24A H 0.9956 0.3923 0.6989 0.085 Uiso 0.5 1 calc R U P . .
H24B H 1.0044 0.3923 0.8011 0.085 Uiso 0.5 1 calc R U P . .


_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
Mg1 O1 2.026(2) . ?
Mg1 O1 2.062(2) 5_666 ?
Mg1 N3 2.223(3) . ?
Mg1 N1 2.287(3) . ?
Mg1 N2 2.325(3) . ?
Mg1 Cl1 2.4429(12) . ?
Mg1 Mg1 3.187(2) 5_666 ?
Cl2 C22 1.759(5) . ?
Cl3 C22 1.756(5) . ?
Cl4 C23 1.725(4) . ?
Cl5 C23 1.734(5) . ?
Cl6 C24 1.738(5) . ?
O1 C5 1.348(4) . ?
O1 Mg1 2.062(2) 5_666 ?
N1 C9 1.341(4) . ?
N1 C4 1.350(4) . ?
N2 C3 1.469(4) . ?
N2 C7 1.476(4) . ?
N2 C10 1.488(4) . ?
N3 C15 1.338(4) . ?
N3 C2 1.346(4) . ?
C1 C9 1.375(5) . ?
C1 C14 1.381(5) . ?
C1 H1 0.9500 . ?
C2 C12 1.386(5) . ?
C2 C3 1.504(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.379(5) . ?
C4 C7 1.495(5) . ?
C5 C8 1.404(5) . ?
C5 C6 1.414(5) . ?
C6 C13 1.385(5) . ?
C6 C10 1.504(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C18 1.393(5) . ?
C8 C16 1.507(5) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C14 1.382(5) . ?
C11 H11 0.9500 . ?
C12 C20 1.376(6) . ?
C12 H12 0.9500 . ?
C13 C17 1.385(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C19 1.374(5) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.383(6) . ?
C17 C21 1.504(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(6) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 Cl6 1.738(5) 2_756 ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

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
O1 Mg1 O1 77.54(10) . 5_666 ?
O1 Mg1 N3 154.08(10) . . ?
O1 Mg1 N3 93.67(10) 5_666 . ?
O1 Mg1 N1 88.87(10) . . ?
O1 Mg1 N1 165.72(10) 5_666 . ?
N3 Mg1 N1 100.51(11) . . ?
O1 Mg1 N2 86.54(9) . . ?
O1 Mg1 N2 108.91(10) 5_666 . ?
N3 Mg1 N2 73.16(10) . . ?
N1 Mg1 N2 74.13(10) . . ?
O1 Mg1 Cl1 113.43(7) . . ?
O1 Mg1 Cl1 96.55(7) 5_666 . ?
N3 Mg1 Cl1 91.61(8) . . ?
N1 Mg1 Cl1 84.77(8) . . ?
N2 Mg1 Cl1 150.81(8) . . ?
O1 Mg1 Mg1 39.18(6) . 5_666 ?
O1 Mg1 Mg1 38.36(6) 5_666 5_666 ?
N3 Mg1 Mg1 127.81(9) . 5_666 ?
N1 Mg1 Mg1 127.91(9) . 5_666 ?
N2 Mg1 Mg1 99.87(8) . 5_666 ?
Cl1 Mg1 Mg1 109.05(5) . 5_666 ?
C5 O1 Mg1 121.74(19) . . ?
C5 O1 Mg1 128.27(19) . 5_666 ?
Mg1 O1 Mg1 102.46(10) . 5_666 ?
C9 N1 C4 117.6(3) . . ?
C9 N1 Mg1 124.0(2) . . ?
C4 N1 Mg1 116.4(2) . . ?
C3 N2 C7 109.0(3) . . ?
C3 N2 C10 109.4(2) . . ?
C7 N2 C10 110.4(3) . . ?
C3 N2 Mg1 107.3(2) . . ?
C7 N2 Mg1 109.66(19) . . ?
C10 N2 Mg1 111.00(19) . . ?
C15 N3 C2 118.1(3) . . ?
C15 N3 Mg1 124.3(2) . . ?
C2 N3 Mg1 117.6(2) . . ?
C9 C1 C14 118.8(3) . . ?
C9 C1 H1 120.6 . . ?
C14 C1 H1 120.6 . . ?
N3 C2 C12 122.1(3) . . ?
N3 C2 C3 115.8(3) . . ?
C12 C2 C3 122.0(3) . . ?
N2 C3 C2 110.5(3) . . ?
N2 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
N2 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
N1 C4 C11 122.3(3) . . ?
N1 C4 C7 115.6(3) . . ?
C11 C4 C7 122.0(3) . . ?
O1 C5 C8 121.4(3) . . ?
O1 C5 C6 120.4(3) . . ?
C8 C5 C6 118.2(3) . . ?
C13 C6 C5 120.0(3) . . ?
C13 C6 C10 120.6(3) . . ?
C5 C6 C10 119.4(3) . . ?
N2 C7 C4 112.9(3) . . ?
N2 C7 H7A 109.0 . . ?
C4 C7 H7A 109.0 . . ?
N2 C7 H7B 109.0 . . ?
C4 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C18 C8 C5 119.5(3) . . ?
C18 C8 C16 120.1(3) . . ?
C5 C8 C16 120.3(3) . . ?
N1 C9 C1 123.3(3) . . ?
N1 C9 H9 118.3 . . ?
C1 C9 H9 118.3 . . ?
N2 C10 C6 112.4(3) . . ?
N2 C10 H10A 109.1 . . ?
C6 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C6 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C4 C11 C14 119.3(3) . . ?
C4 C11 H11 120.3 . . ?
C14 C11 H11 120.3 . . ?
C20 C12 C2 118.9(3) . . ?
C20 C12 H12 120.5 . . ?
C2 C12 H12 120.5 . . ?
C17 C13 C6 122.1(3) . . ?
C17 C13 H13 118.9 . . ?
C6 C13 H13 118.9 . . ?
C1 C14 C11 118.7(3) . . ?
C1 C14 H14 120.6 . . ?
C11 C14 H14 120.6 . . ?
N3 C15 C19 123.0(3) . . ?
N3 C15 H15 118.5 . . ?
C19 C15 H15 118.5 . . ?
C8 C16 H16A 109.5 . . ?
C8 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C8 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C13 117.5(3) . . ?
C18 C17 C21 121.1(4) . . ?
C13 C17 C21 121.4(4) . . ?
C17 C18 C8 122.5(3) . . ?
C17 C18 H18 118.8 . . ?
C8 C18 H18 118.8 . . ?
C15 C19 C20 118.8(4) . . ?
C15 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C12 C20 C19 119.1(3) . . ?
C12 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Cl3 C22 Cl2 112.7(2) . . ?
Cl3 C22 H22A 109.0 . . ?
Cl2 C22 H22A 109.0 . . ?
Cl3 C22 H22B 109.0 . . ?
Cl2 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
Cl4 C23 Cl5 113.2(2) . . ?
Cl4 C23 H23A 108.9 . . ?
Cl5 C23 H23A 108.9 . . ?
Cl4 C23 H23B 108.9 . . ?
Cl5 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
Cl6 C24 Cl6 114.2(5) . 2_756 ?
Cl6 C24 H24A 108.7 . . ?
Cl6 C24 H24A 108.7 2_756 . ?
Cl6 C24 H24B 108.7 . . ?
Cl6 C24 H24B 108.7 2_756 . ?
H24A C24 H24B 107.6 . . ?

# start Validation Reply Form
_vrf_DIFMX01_mk395               
;
PROBLEM:
RESPONSE:
The relatively high residual peak is due to minor disorder of the DCM
solvent.
;
_vrf_DIFMX02_mk395               
;
PROBLEM:
RESPONSE:
The relatively high residual peak is due to minor disorder of the DCM
solvent.
;
_vrf_PLAT971_mk395               
;
PROBLEM:
RESPONSE:
The relatively high residual peak is due to minor disorder of the DCM
solvent.
;
_vrf_PLAT097_mk395               
;
PROBLEM:
RESPONSE:
The relatively high residual peak is due to minor disorder of the DCM
solvent.
;
# end Validation Reply Form

_refine_diff_density_max         1.710
_refine_diff_density_min         -1.077
_refine_diff_density_rms         0.083

