# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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. 
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data_mo_ISOPROPYLE_0m
_database_code_depnum_ccdc_archive 'CCDC 2194541'
loop_
_audit_author_name
_audit_author_address
'Dr Rajesh G Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2022-08-04 deposited with the CCDC.	2022-11-03 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         'C16 H21 Br Mn N4 O2 P'
_chemical_formula_sum            'C16 H21 Br Mn N4 O2 P'
_chemical_formula_weight         467.19

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'
P P 0.1023 0.0942 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   9.1016(5)
_cell_length_b                   14.4759(6)
_cell_length_c                   28.6257(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3771.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5261
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      27.18

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_F_000             1888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    2.921
_shelx_estimated_absorpt_T_min   0.419
_shelx_estimated_absorpt_T_max   0.541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1601
_exptl_absorpt_correction_T_max  0.2092
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            73416
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_av_R_equivalents  0.1649
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.652
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4688
_reflns_number_gt                3291
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_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)+(0.0315P)²+6.2454P] 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         4688
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.29618(4) 0.85611(3) 0.66710(2) 0.02119(11) Uani 1 1 d . . . . .
Mn1 Mn 0.45680(6) 0.75341(4) 0.61333(2) 0.01752(14) Uani 1 1 d . . . . .
P1 P 0.27442(11) 0.65098(7) 0.60277(3) 0.0162(2) Uani 1 1 d . . . . .
O1 O 0.6607(3) 0.6537(2) 0.55240(10) 0.0310(7) Uani 1 1 d . . . . .
O2 O 0.4088(3) 0.8742(2) 0.53198(10) 0.0296(7) Uani 1 1 d . . . . .
N1 N 0.4912(3) 0.6784(2) 0.67153(10) 0.0185(7) Uani 1 1 d . . . . .
N2 N 0.6673(4) 0.7868(3) 0.68549(12) 0.0269(8) Uani 1 1 d . . . . .
N3 N 0.6256(4) 0.8209(2) 0.64314(11) 0.0227(8) Uani 1 1 d . . . . .
N4 N 0.3065(4) 0.5797(2) 0.64999(10) 0.0202(7) Uani 1 1 d . . . . .
H4N H 0.2557 0.5284 0.6534 0.024 Uiso 1 1 calc R U . . .
C1 C 0.4112(4) 0.6032(3) 0.68204(13) 0.0188(8) Uani 1 1 d . . . . .
C2 C 0.4345(5) 0.5553(3) 0.72399(14) 0.0267(10) Uani 1 1 d . . . . .
H2 H 0.3799 0.5012 0.7310 0.032 Uiso 1 1 calc R U . . .
C3 C 0.5379(5) 0.5886(3) 0.75463(14) 0.0326(11) Uani 1 1 d . . . . .
H3 H 0.5546 0.5569 0.7832 0.039 Uiso 1 1 calc R U . . .
C4 C 0.6185(5) 0.6677(3) 0.74459(14) 0.0297(10) Uani 1 1 d . . . . .
H4 H 0.6880 0.6922 0.7660 0.036 Uiso 1 1 calc R U . . .
C5 C 0.5927(5) 0.7088(3) 0.70198(14) 0.0257(9) Uani 1 1 d . . . . .
C6 C 0.7847(5) 0.8348(4) 0.70284(17) 0.0412(12) Uani 1 1 d . . . . .
H6 H 0.8340 0.8238 0.7316 0.049 Uiso 1 1 calc R U . . .
C7 C 0.8170(6) 0.9012(4) 0.67099(17) 0.0433(13) Uani 1 1 d . . . . .
H7 H 0.8926 0.9463 0.6731 0.052 Uiso 1 1 calc R U . . .
C8 C 0.7171(5) 0.8900(3) 0.63456(15) 0.0297(10) Uani 1 1 d . . . . .
H8 H 0.7149 0.9271 0.6072 0.036 Uiso 1 1 calc R U . . .
C9 C 0.5775(5) 0.6896(3) 0.57702(14) 0.0234(9) Uani 1 1 d . . . . .
C10 C 0.4233(4) 0.8273(3) 0.56407(14) 0.0217(9) Uani 1 1 d . . . . .
C11 C 0.2710(5) 0.5715(3) 0.55242(12) 0.0207(9) Uani 1 1 d . . . . .
H11 H 0.1713 0.5425 0.5514 0.025 Uiso 1 1 calc R U . . .
C12 C 0.3825(5) 0.4940(3) 0.55653(15) 0.0278(10) Uani 1 1 d . . . . .
H12A H 0.3785 0.4554 0.5284 0.042 Uiso 1 1 calc R U . . .
H12B H 0.3599 0.4563 0.5840 0.042 Uiso 1 1 calc R U . . .
H12C H 0.4812 0.5204 0.5597 0.042 Uiso 1 1 calc R U . . .
C13 C 0.2922(5) 0.6241(3) 0.50654(13) 0.0288(10) Uani 1 1 d . . . . .
H13A H 0.2707 0.5831 0.4802 0.043 Uiso 1 1 calc R U . . .
H13B H 0.3940 0.6457 0.5043 0.043 Uiso 1 1 calc R U . . .
H13C H 0.2255 0.6773 0.5057 0.043 Uiso 1 1 calc R U . . .
C14 C 0.0793(4) 0.6816(3) 0.61218(13) 0.0197(8) Uani 1 1 d . . . . .
H14 H 0.0741 0.7151 0.6427 0.024 Uiso 1 1 calc R U . . .
C15 C -0.0243(5) 0.5984(3) 0.61601(15) 0.0278(9) Uani 1 1 d . . . . .
H15A H -0.0425 0.5730 0.5848 0.042 Uiso 1 1 calc R U . . .
H15B H -0.1176 0.6181 0.6299 0.042 Uiso 1 1 calc R U . . .
H15C H 0.0208 0.5510 0.6357 0.042 Uiso 1 1 calc R U . . .
C16 C 0.0253(4) 0.7487(3) 0.57477(14) 0.0238(9) Uani 1 1 d . . . . .
H16A H 0.0205 0.7169 0.5446 0.036 Uiso 1 1 calc R U . . .
H16B H 0.0933 0.8010 0.5725 0.036 Uiso 1 1 calc R U . . .
H16C H -0.0727 0.7713 0.5832 0.036 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 2.5917(7) . ?
Mn1 C9 1.772(4) . ?
Mn1 C10 1.796(4) . ?
Mn1 N3 2.011(3) . ?
Mn1 N1 2.013(3) . ?
Mn1 P1 2.2462(12) . ?
P1 N4 1.726(3) . ?
P1 C11 1.844(4) . ?
P1 C14 1.850(4) . ?
O1 C9 1.158(5) . ?
O2 C10 1.149(5) . ?
N1 C1 1.343(5) . ?
N1 C5 1.344(5) . ?
N2 N3 1.363(5) . ?
N2 C6 1.368(6) . ?
N2 C5 1.400(6) . ?
N3 C8 1.324(5) . ?
N4 C1 1.366(5) . ?
N4 H4N 0.8800 . ?
C1 C2 1.403(5) . ?
C2 C3 1.374(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(6) . ?
C4 H4 0.9500 . ?
C6 C7 1.358(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(6) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C11 C12 1.517(6) . ?
C11 C13 1.531(5) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C16 1.528(5) . ?
C14 C15 1.534(6) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C9 Mn1 C10 87.44(18) . . ?
C9 Mn1 N3 91.63(16) . . ?
C10 Mn1 N3 99.97(17) . . ?
C9 Mn1 N1 96.20(16) . . ?
C10 Mn1 N1 175.86(16) . . ?
N3 Mn1 N1 78.01(14) . . ?
C9 Mn1 P1 92.01(14) . . ?
C10 Mn1 P1 99.34(13) . . ?
N3 Mn1 P1 160.49(10) . . ?
N1 Mn1 P1 82.55(10) . . ?
C9 Mn1 Br1 175.59(14) . . ?
C10 Mn1 Br1 91.65(13) . . ?
N3 Mn1 Br1 84.27(9) . . ?
N1 Mn1 Br1 84.57(9) . . ?
P1 Mn1 Br1 92.40(3) . . ?
N4 P1 C11 103.99(17) . . ?
N4 P1 C14 101.04(17) . . ?
C11 P1 C14 104.30(19) . . ?
N4 P1 Mn1 99.46(12) . . ?
C11 P1 Mn1 121.98(14) . . ?
C14 P1 Mn1 122.11(14) . . ?
C1 N1 C5 119.5(3) . . ?
C1 N1 Mn1 122.6(3) . . ?
C5 N1 Mn1 117.9(3) . . ?
N3 N2 C6 110.9(4) . . ?
N3 N2 C5 117.2(3) . . ?
C6 N2 C5 131.8(4) . . ?
C8 N3 N2 105.3(3) . . ?
C8 N3 Mn1 140.2(3) . . ?
N2 N3 Mn1 114.5(3) . . ?
C1 N4 P1 119.7(3) . . ?
C1 N4 H4N 120.2 . . ?
P1 N4 H4N 120.2 . . ?
N1 C1 N4 115.4(3) . . ?
N1 C1 C2 120.7(4) . . ?
N4 C1 C2 123.8(4) . . ?
C3 C2 C1 118.5(4) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 121.2(4) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 116.7(4) . . ?
C5 C4 H4 121.7 . . ?
C3 C4 H4 121.7 . . ?
N1 C5 C4 123.4(4) . . ?
N1 C5 N2 112.3(4) . . ?
C4 C5 N2 124.3(4) . . ?
C7 C6 N2 106.6(4) . . ?
C7 C6 H6 126.7 . . ?
N2 C6 H6 126.7 . . ?
C6 C7 C8 106.2(4) . . ?
C6 C7 H7 126.9 . . ?
C8 C7 H7 126.9 . . ?
N3 C8 C7 111.1(4) . . ?
N3 C8 H8 124.5 . . ?
C7 C8 H8 124.5 . . ?
O1 C9 Mn1 175.3(4) . . ?
O2 C10 Mn1 176.8(4) . . ?
C12 C11 C13 110.5(3) . . ?
C12 C11 P1 112.9(3) . . ?
C13 C11 P1 110.9(3) . . ?
C12 C11 H11 107.4 . . ?
C13 C11 H11 107.4 . . ?
P1 C11 H11 107.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 C14 C15 110.6(3) . . ?
C16 C14 P1 111.1(3) . . ?
C15 C14 P1 114.4(3) . . ?
C16 C14 H14 106.8 . . ?
C15 C14 H14 106.8 . . ?
P1 C14 H14 106.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
C6 N2 N3 C8 -0.2(5) . . . . ?
C5 N2 N3 C8 -176.6(3) . . . . ?
C6 N2 N3 Mn1 178.4(3) . . . . ?
C5 N2 N3 Mn1 2.1(4) . . . . ?
C11 P1 N4 C1 132.8(3) . . . . ?
C14 P1 N4 C1 -119.3(3) . . . . ?
Mn1 P1 N4 C1 6.3(3) . . . . ?
C5 N1 C1 N4 177.3(3) . . . . ?
Mn1 N1 C1 N4 1.3(5) . . . . ?
C5 N1 C1 C2 -1.1(5) . . . . ?
Mn1 N1 C1 C2 -177.1(3) . . . . ?
P1 N4 C1 N1 -5.5(5) . . . . ?
P1 N4 C1 C2 172.9(3) . . . . ?
N1 C1 C2 C3 1.8(6) . . . . ?
N4 C1 C2 C3 -176.5(4) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
C2 C3 C4 C5 -2.0(6) . . . . ?
C1 N1 C5 C4 -1.3(6) . . . . ?
Mn1 N1 C5 C4 175.0(3) . . . . ?
C1 N1 C5 N2 179.2(3) . . . . ?
Mn1 N1 C5 N2 -4.6(4) . . . . ?
C3 C4 C5 N1 2.8(6) . . . . ?
C3 C4 C5 N2 -177.7(4) . . . . ?
N3 N2 C5 N1 1.6(5) . . . . ?
C6 N2 C5 N1 -173.9(4) . . . . ?
N3 N2 C5 C4 -178.0(4) . . . . ?
C6 N2 C5 C4 6.6(7) . . . . ?
N3 N2 C6 C7 0.6(5) . . . . ?
C5 N2 C6 C7 176.2(4) . . . . ?
N2 C6 C7 C8 -0.7(6) . . . . ?
N2 N3 C8 C7 -0.3(5) . . . . ?
Mn1 N3 C8 C7 -178.3(4) . . . . ?
C6 C7 C8 N3 0.6(6) . . . . ?
N4 P1 C11 C12 -37.4(3) . . . . ?
C14 P1 C11 C12 -142.9(3) . . . . ?
Mn1 P1 C11 C12 73.4(3) . . . . ?
N4 P1 C11 C13 -162.1(3) . . . . ?
C14 P1 C11 C13 92.4(3) . . . . ?
Mn1 P1 C11 C13 -51.2(3) . . . . ?
N4 P1 C14 C16 178.0(3) . . . . ?
C11 P1 C14 C16 -74.3(3) . . . . ?
Mn1 P1 C14 C16 69.4(3) . . . . ?
N4 P1 C14 C15 -56.0(3) . . . . ?
C11 P1 C14 C15 51.7(3) . . . . ?
Mn1 P1 C14 C15 -164.6(2) . . . . ?

_refine_diff_density_max         0.798
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.115



