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


data_mk392

_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



