# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_Cat2
_database_code_depnum_ccdc_archive 'CCDC 2098470'
loop_
_audit_author_name
_audit_author_address
'PRIYANKA priyanka.chakraborty'
;KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY (KAUST)
India
;
_audit_update_record             
;
2021-07-22 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_audit_creation_date             2020-03-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H26 Br2 Mn N3 P, C3 H7 N O'
_chemical_formula_sum            'C21 H33 Br2 Mn N4 O P'
_chemical_formula_weight         603.24
_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'
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'
P P 0.1023 0.0942 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8591(13)
_cell_length_b                   10.2949(15)
_cell_length_c                   14.571(2)
_cell_angle_alpha                96.607(5)
_cell_angle_beta                 97.226(5)
_cell_angle_gamma                94.321(5)
_cell_volume                     1304.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      2.56
_cell_measurement_theta_min      32.64
_shelx_estimated_absorpt_T_max   0.559
_shelx_estimated_absorpt_T_min   0.501
_exptl_absorpt_coefficient_mu    3.650
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.3545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1348 before and 0.0999 after correction.
The Ratio of minimum to maximum transmission is 0.4749.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             610
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1135
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            43224
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.936
_diffrn_reflns_theta_min         2.302
_diffrn_ambient_temperature      130.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6462
_reflns_number_total             9718
_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 V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.351
_refine_diff_density_min         -1.239
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         9718
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0521
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0723P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1462
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C9(H9), C1(H1), C7(H7), C8(H8), C2(H2), C19(H19), C3(H3A), C4(H4)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C21(H21A,H21B,H21C), C18(H18A,H18B,H18C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C20(H20A,
 H20B,H20C)
;
_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
Br2 Br 0.49914(4) 1.00780(3) 0.75713(2) 0.02825(9) Uani 1 1 d . . . . .
Br1 Br 0.18760(3) 0.78596(3) 0.55819(2) 0.02703(9) Uani 1 1 d . . . . .
Mn1 Mn 0.40811(5) 0.77802(4) 0.68370(3) 0.01873(10) Uani 1 1 d . . . . .
P004 P 0.28483(9) 0.67374(7) 0.81895(6) 0.02000(15) Uani 1 1 d . . . . .
O1 O 1.2077(3) 0.2781(2) 0.85155(18) 0.0332(6) Uani 1 1 d . . . . .
N2 N 0.4933(3) 0.5777(2) 0.68635(17) 0.0179(5) Uani 1 1 d . . . . .
N1 N 0.5868(3) 0.7647(2) 0.59028(18) 0.0204(5) Uani 1 1 d . . . . .
N3 N 0.3467(3) 0.5214(2) 0.80135(18) 0.0220(5) Uani 1 1 d . . . . .
H3 H 0.315123 0.461541 0.834858 0.026 Uiso 1 1 calc R . . . .
N4 N 1.0027(3) 0.1547(3) 0.7669(2) 0.0268(6) Uani 1 1 d . . . . .
C9 C 0.4853(3) 0.3573(3) 0.7276(2) 0.0225(6) Uani 1 1 d . . . . .
H9 H 0.449753 0.294913 0.764989 0.027 Uiso 1 1 calc R . . . .
C1 C 0.6329(4) 0.8647(3) 0.5455(2) 0.0248(6) Uani 1 1 d . . . . .
H1 H 0.592203 0.946748 0.557677 0.030 Uiso 1 1 calc R . . . .
C10 C 0.4425(3) 0.4871(3) 0.7382(2) 0.0197(5) Uani 1 1 d . . . . .
C7 C 0.6324(3) 0.4165(3) 0.6104(2) 0.0238(6) Uani 1 1 d . . . . .
H7 H 0.697977 0.393855 0.565470 0.029 Uiso 1 1 calc R . . . .
C8 C 0.5780(3) 0.3232(3) 0.6632(2) 0.0245(6) Uani 1 1 d . . . . .
H8 H 0.605898 0.235819 0.654169 0.029 Uiso 1 1 calc R . . . .
C6 C 0.5892(3) 0.5423(3) 0.6246(2) 0.0186(5) Uani 1 1 d . . . . .
C5 C 0.6433(3) 0.6485(3) 0.5729(2) 0.0202(5) Uani 1 1 d . . . . .
C2 C 0.7361(4) 0.8532(3) 0.4829(2) 0.0294(7) Uani 1 1 d . . . . .
H2 H 0.765545 0.925638 0.452195 0.035 Uiso 1 1 calc R . . . .
C11 C 0.3727(4) 0.7328(3) 0.9408(2) 0.0285(7) Uani 1 1 d . . . . .
C19 C 1.1511(4) 0.1940(3) 0.7876(3) 0.0282(7) Uani 1 1 d . . . . .
H19 H 1.218498 0.153487 0.749758 0.034 Uiso 1 1 calc R . . . .
C3 C 0.7961(4) 0.7348(3) 0.4655(2) 0.0300(7) Uani 1 1 d . . . . .
H3A H 0.868776 0.725030 0.423098 0.036 Uiso 1 1 calc R . . . .
C16 C 0.0732(4) 0.6394(3) 0.8053(3) 0.0308(7) Uani 1 1 d . . . . .
C4 C 0.7502(3) 0.6305(3) 0.5101(2) 0.0257(6) Uani 1 1 d . . . . .
H4 H 0.790001 0.547987 0.498492 0.031 Uiso 1 1 calc R . . . .
C12 C 0.5449(4) 0.7526(4) 0.9360(3) 0.0376(8) Uani 1 1 d . . . . .
H12A H 0.564034 0.815577 0.892289 0.056 Uiso 1 1 calc GR . . . .
H12B H 0.581814 0.668453 0.914608 0.056 Uiso 1 1 calc GR . . . .
H12C H 0.598910 0.786378 0.998038 0.056 Uiso 1 1 calc GR . . . .
C21 C 0.9410(4) 0.0635(3) 0.6849(3) 0.0330(7) Uani 1 1 d . . . . .
H21A H 0.886288 0.111027 0.638485 0.050 Uiso 1 1 calc GR . . . .
H21B H 0.870401 -0.004381 0.702396 0.050 Uiso 1 1 calc GR . . . .
H21C H 1.024705 0.022351 0.658348 0.050 Uiso 1 1 calc GR . . . .
C18 C 0.0074(4) 0.5799(4) 0.8860(3) 0.0419(9) Uani 1 1 d . . . . .
H18A H -0.102059 0.554084 0.867945 0.063 Uiso 1 1 calc GR . . . .
H18B H 0.022313 0.645296 0.941546 0.063 Uiso 1 1 calc GR . . . .
H18C H 0.060033 0.502592 0.899688 0.063 Uiso 1 1 calc GR . . . .
C13 C 0.3473(5) 0.6352(4) 1.0114(3) 0.0370(8) Uani 1 1 d . . . . .
H13A H 0.411399 0.666255 1.070882 0.055 Uiso 1 1 calc GR . . . .
H13B H 0.374881 0.548627 0.987162 0.055 Uiso 1 1 calc GR . . . .
H13C H 0.239653 0.628630 1.021035 0.055 Uiso 1 1 calc GR . . . .
C14 C 0.3145(5) 0.8654(3) 0.9717(3) 0.0419(9) Uani 1 1 d . . . . .
H14A H 0.368718 0.901682 1.033232 0.063 Uiso 1 1 calc GR . . . .
H14B H 0.204700 0.853018 0.975202 0.063 Uiso 1 1 calc GR . . . .
H14C H 0.332995 0.926323 0.926528 0.063 Uiso 1 1 calc GR . . . .
C17 C 0.0298(4) 0.5421(4) 0.7165(3) 0.0386(9) Uani 1 1 d . . . . .
H17A H 0.064385 0.456392 0.727546 0.058 Uiso 1 1 calc GR . . . .
H17B H 0.078597 0.574380 0.665692 0.058 Uiso 1 1 calc GR . . . .
H17C H -0.081413 0.533399 0.699384 0.058 Uiso 1 1 calc GR . . . .
C15 C 0.0037(4) 0.7677(4) 0.7914(3) 0.0435(10) Uani 1 1 d . . . . .
H15A H 0.036660 0.800841 0.736010 0.065 Uiso 1 1 calc GR . . . .
H15B H 0.037701 0.832374 0.846236 0.065 Uiso 1 1 calc GR . . . .
H15C H -0.107978 0.752331 0.782922 0.065 Uiso 1 1 calc GR . . . .
C20 C 0.8959(5) 0.2130(5) 0.8214(3) 0.0552(13) Uani 1 1 d . . . . .
H20A H 0.946752 0.243377 0.884720 0.083 Uiso 1 1 calc GR . . . .
H20B H 0.810451 0.147843 0.823953 0.083 Uiso 1 1 calc GR . . . .
H20C H 0.857250 0.287750 0.792761 0.083 Uiso 1 1 calc GR . . . .


_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
Br2 Mn1 2.5108(6) . ?
Br1 Mn1 2.5155(6) . ?
Mn1 P004 2.6609(9) . ?
Mn1 N2 2.251(2) . ?
Mn1 N1 2.216(3) . ?
P004 N3 1.702(3) . ?
P004 C11 1.861(3) . ?
P004 C16 1.863(3) . ?
O1 C19 1.225(4) . ?
N2 C10 1.352(4) . ?
N2 C6 1.353(4) . ?
N1 C1 1.346(4) . ?
N1 C5 1.341(4) . ?
N3 H3 0.8800 . ?
N3 C10 1.363(4) . ?
N4 C19 1.333(4) . ?
N4 C21 1.452(4) . ?
N4 C20 1.432(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.414(4) . ?
C9 C8 1.356(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.371(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.393(4) . ?
C7 C6 1.378(4) . ?
C8 H8 0.9500 . ?
C6 C5 1.481(4) . ?
C5 C4 1.405(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(5) . ?
C11 C12 1.536(5) . ?
C11 C13 1.543(5) . ?
C11 C14 1.535(5) . ?
C19 H19 0.9500 . ?
C3 H3A 0.9500 . ?
C3 C4 1.379(4) . ?
C16 C18 1.544(5) . ?
C16 C17 1.531(5) . ?
C16 C15 1.522(5) . ?
C4 H4 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
Br2 Mn1 Br1 109.03(2) . . ?
Br2 Mn1 P004 103.05(3) . . ?
Br1 Mn1 P004 104.90(3) . . ?
N2 Mn1 Br2 136.48(6) . . ?
N2 Mn1 Br1 113.67(6) . . ?
N2 Mn1 P004 74.04(7) . . ?
N1 Mn1 Br2 94.79(6) . . ?
N1 Mn1 Br1 96.50(7) . . ?
N1 Mn1 P004 145.59(7) . . ?
N1 Mn1 N2 72.77(9) . . ?
N3 P004 Mn1 98.22(9) . . ?
N3 P004 C11 102.31(14) . . ?
N3 P004 C16 103.16(14) . . ?
C11 P004 Mn1 116.94(11) . . ?
C11 P004 C16 113.76(17) . . ?
C16 P004 Mn1 118.26(12) . . ?
C10 N2 Mn1 124.2(2) . . ?
C10 N2 C6 118.5(2) . . ?
C6 N2 Mn1 116.97(18) . . ?
C1 N1 Mn1 123.1(2) . . ?
C5 N1 Mn1 117.96(19) . . ?
C5 N1 C1 118.8(3) . . ?
P004 N3 H3 118.2 . . ?
C10 N3 P004 123.6(2) . . ?
C10 N3 H3 118.2 . . ?
C19 N4 C21 122.6(3) . . ?
C19 N4 C20 119.7(3) . . ?
C20 N4 C21 117.4(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 119.0(3) . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C2 122.8(3) . . ?
C2 C1 H1 118.6 . . ?
N2 C10 N3 119.3(3) . . ?
N2 C10 C9 121.4(3) . . ?
N3 C10 C9 119.3(3) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.8(3) . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
N2 C6 C7 122.4(3) . . ?
N2 C6 C5 115.0(2) . . ?
C7 C6 C5 122.6(3) . . ?
N1 C5 C6 116.5(3) . . ?
N1 C5 C4 121.2(3) . . ?
C4 C5 C6 122.3(3) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.8(3) . . ?
C3 C2 H2 120.6 . . ?
C12 C11 P004 104.9(2) . . ?
C12 C11 C13 108.0(3) . . ?
C13 C11 P004 114.6(2) . . ?
C14 C11 P004 109.1(2) . . ?
C14 C11 C12 109.3(3) . . ?
C14 C11 C13 110.8(3) . . ?
O1 C19 N4 125.3(3) . . ?
O1 C19 H19 117.3 . . ?
N4 C19 H19 117.3 . . ?
C2 C3 H3A 120.2 . . ?
C2 C3 C4 119.6(3) . . ?
C4 C3 H3A 120.2 . . ?
C18 C16 P004 116.2(2) . . ?
C17 C16 P004 106.1(2) . . ?
C17 C16 C18 108.2(3) . . ?
C15 C16 P004 107.6(2) . . ?
C15 C16 C18 109.3(3) . . ?
C15 C16 C17 109.3(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 H4 120.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C21 H21A 109.5 . . ?
N4 C21 H21B 109.5 . . ?
N4 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C20 H20A 109.5 . . ?
N4 C20 H20B 109.5 . . ?
N4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cat1
_database_code_depnum_ccdc_archive 'CCDC 2099104'
loop_
_audit_author_name
_audit_author_address
'PRIYANKA priyanka.chakraborty'
;KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY (KAUST)
India
;
_audit_update_record             
;
2021-07-25 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H26 Cl2 Mn N3 P'
_chemical_formula_weight         441.23

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'
Cl Cl 0.1484 0.1585 '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'
P P 0.1023 0.0942 '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                   12.9997(16)
_cell_length_b                   12.4522(13)
_cell_length_c                   14.3781(18)
_cell_angle_alpha                90
_cell_angle_beta                 109.245(5)
_cell_angle_gamma                90
_cell_volume                     2197.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9920
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      33.09

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             916
_exptl_transmission_factor_min   0.823
_exptl_transmission_factor_max   0.852
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.923
_shelx_estimated_absorpt_T_min   0.823
_shelx_estimated_absorpt_T_max   0.852
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   Sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48566
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.834
_diffrn_reflns_theta_max         33.159
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8376
_reflns_number_gt                6245
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8376
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1588
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
C1 C 0.59988(18) 0.49588(18) 0.72303(16) 0.0309(4) Uani 1 1 d . . . . .
H1 H 0.641751 0.545665 0.770562 0.037 Uiso 1 1 calc R U . . .
C2 C 0.63955(18) 0.39249(19) 0.72385(16) 0.0326(5) Uani 1 1 d . . . . .
H2 H 0.707219 0.371563 0.770488 0.039 Uiso 1 1 calc R U . . .
C3 C 0.5777(2) 0.32101(18) 0.65482(16) 0.0335(5) Uani 1 1 d . . . . .
H3 H 0.602318 0.249395 0.653489 0.040 Uiso 1 1 calc R U . . .
C4 C 0.47969(18) 0.35355(16) 0.58752(15) 0.0275(4) Uani 1 1 d . . . . .
H4 H 0.436287 0.304689 0.539913 0.033 Uiso 1 1 calc R U . . .
C5 C 0.44553(15) 0.45946(14) 0.59064(13) 0.0192(3) Uani 1 1 d . . . . .
C6 C 0.34164(15) 0.50218(14) 0.52183(12) 0.0184(3) Uani 1 1 d . . . . .
C7 C 0.27425(17) 0.44200(15) 0.44567(15) 0.0273(4) Uani 1 1 d . . . . .
H7 H 0.292656 0.370384 0.434656 0.033 Uiso 1 1 calc R U . . .
C8 C 0.17747(19) 0.48954(17) 0.38469(16) 0.0328(5) Uani 1 1 d . . . . .
H8 H 0.129307 0.449685 0.331820 0.039 Uiso 1 1 calc R U . . .
C9 C 0.15217(17) 0.59339(17) 0.40117(14) 0.0273(4) Uani 1 1 d . . . . .
H9 H 0.087080 0.626302 0.360178 0.033 Uiso 1 1 calc R U . . .
C10 C 0.22564(15) 0.64985(13) 0.48078(12) 0.0179(3) Uani 1 1 d . . . . .
C11 C 0.18203(16) 0.83983(15) 0.67158(14) 0.0224(3) Uani 1 1 d . . . . .
C12 C 0.06744(17) 0.88028(18) 0.61376(17) 0.0303(4) Uani 1 1 d . . . . .
H12A H 0.036647 0.836301 0.554545 0.045 Uiso 1 1 calc R U . . .
H12B H 0.071462 0.955301 0.594650 0.045 Uiso 1 1 calc R U . . .
H12C H 0.020911 0.875115 0.655108 0.045 Uiso 1 1 calc R U . . .
C13 C 0.2356(2) 0.9122(2) 0.76060(17) 0.0354(5) Uani 1 1 d . . . . .
H13A H 0.236983 0.986385 0.738288 0.053 Uiso 1 1 calc R U . . .
H13B H 0.310254 0.887684 0.794326 0.053 Uiso 1 1 calc R U . . .
H13C H 0.193752 0.908827 0.806120 0.053 Uiso 1 1 calc R U . . .
C14 C 0.17151(18) 0.72522(18) 0.70827(18) 0.0321(4) Uani 1 1 d . . . . .
H14A H 0.124228 0.726511 0.749097 0.048 Uiso 1 1 calc R U . . .
H14B H 0.243753 0.698561 0.747393 0.048 Uiso 1 1 calc R U . . .
H14C H 0.139858 0.677802 0.651623 0.048 Uiso 1 1 calc R U . . .
C15 C 0.30370(16) 0.95615(14) 0.54611(14) 0.0212(3) Uani 1 1 d . . . . .
C16 C 0.34994(18) 0.92651(17) 0.46366(15) 0.0275(4) Uani 1 1 d . . . . .
H16A H 0.294221 0.888441 0.411046 0.041 Uiso 1 1 calc R U . . .
H16B H 0.413800 0.880119 0.490471 0.041 Uiso 1 1 calc R U . . .
H16C H 0.371225 0.992096 0.437004 0.041 Uiso 1 1 calc R U . . .
C17 C 0.20397(19) 1.02951(16) 0.50373(17) 0.0313(4) Uani 1 1 d . . . . .
H17A H 0.222808 1.088965 0.467675 0.047 Uiso 1 1 calc R U . . .
H17B H 0.181709 1.058214 0.557645 0.047 Uiso 1 1 calc R U . . .
H17C H 0.143865 0.988098 0.458860 0.047 Uiso 1 1 calc R U . . .
C18 C 0.39358(18) 1.01552(17) 0.62707(16) 0.0304(4) Uani 1 1 d . . . . .
H18A H 0.413245 1.081519 0.599819 0.046 Uiso 1 1 calc R U . . .
H18B H 0.457829 0.969193 0.651534 0.046 Uiso 1 1 calc R U . . .
H18C H 0.366877 1.033634 0.681406 0.046 Uiso 1 1 calc R U . . .
Cl1 Cl 0.59372(4) 0.78470(4) 0.64556(4) 0.02586(11) Uani 1 1 d . . . . .
Cl2 Cl 0.46475(4) 0.68028(4) 0.83626(3) 0.02552(11) Uani 1 1 d . . . . .
H3N H 0.139(2) 0.779(2) 0.4582(19) 0.027(7) Uiso 1 1 d . . . . .
Mn1 Mn 0.44260(2) 0.69254(2) 0.66535(2) 0.01820(8) Uani 1 1 d . . . . .
N1 N 0.50532(13) 0.52884(13) 0.65837(12) 0.0226(3) Uani 1 1 d . . . . .
N2 N 0.31837(12) 0.60533(11) 0.53973(11) 0.0171(3) Uani 1 1 d . . . . .
N3 N 0.20177(13) 0.75400(12) 0.49903(11) 0.0201(3) Uani 1 1 d . . . . .
P1 P 0.27723(4) 0.82595(4) 0.59917(3) 0.01694(10) 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
C1 N1 1.338(3) . ?
C1 C2 1.385(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.378(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.342(2) . ?
C5 C6 1.485(2) . ?
C6 N2 1.363(2) . ?
C6 C7 1.377(3) . ?
C7 C8 1.405(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.374(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.413(2) . ?
C9 H9 0.9500 . ?
C10 N2 1.344(2) . ?
C10 N3 1.379(2) . ?
C11 C12 1.532(3) . ?
C11 C13 1.532(3) . ?
C11 C14 1.543(3) . ?
C11 P1 1.8695(19) . ?
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 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C17 1.538(3) . ?
C15 C18 1.540(3) . ?
C15 C16 1.540(3) . ?
C15 P1 1.8714(18) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
Cl1 Mn1 2.3719(6) . ?
Cl2 Mn1 2.3829(6) . ?
Mn1 N1 2.2099(16) . ?
Mn1 N2 2.2642(15) . ?
Mn1 P1 2.6340(6) . ?
N3 P1 1.7050(15) . ?
N3 H3N 0.89(3) . ?

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 C1 C2 123.0(2) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 119.97(19) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.13(17) . . ?
N1 C5 C6 115.78(15) . . ?
C4 C5 C6 123.08(17) . . ?
N2 C6 C7 122.71(16) . . ?
N2 C6 C5 114.92(15) . . ?
C7 C6 C5 122.37(16) . . ?
C6 C7 C8 118.09(17) . . ?
C6 C7 H7 121.0 . . ?
C8 C7 H7 121.0 . . ?
C9 C8 C7 120.33(18) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 118.14(18) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
N2 C10 N3 118.65(15) . . ?
N2 C10 C9 122.15(16) . . ?
N3 C10 C9 119.20(16) . . ?
C12 C11 C13 110.65(17) . . ?
C12 C11 C14 108.04(17) . . ?
C13 C11 C14 108.99(18) . . ?
C12 C11 P1 115.59(14) . . ?
C13 C11 P1 108.52(14) . . ?
C14 C11 P1 104.74(13) . . ?
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 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C17 C15 C18 110.17(16) . . ?
C17 C15 C16 109.22(16) . . ?
C18 C15 C16 107.79(16) . . ?
C17 C15 P1 115.58(14) . . ?
C18 C15 P1 107.67(13) . . ?
C16 C15 P1 106.08(12) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 Mn1 N2 72.44(6) . . ?
N1 Mn1 Cl1 96.21(5) . . ?
N2 Mn1 Cl1 122.52(4) . . ?
N1 Mn1 Cl2 93.83(4) . . ?
N2 Mn1 Cl2 127.15(4) . . ?
Cl1 Mn1 Cl2 109.35(2) . . ?
N1 Mn1 P1 146.59(5) . . ?
N2 Mn1 P1 74.44(4) . . ?
Cl1 Mn1 P1 105.14(2) . . ?
Cl2 Mn1 P1 102.697(19) . . ?
C1 N1 C5 119.11(17) . . ?
C1 N1 Mn1 121.31(14) . . ?
C5 N1 Mn1 119.53(12) . . ?
C10 N2 C6 118.57(15) . . ?
C10 N2 Mn1 124.13(11) . . ?
C6 N2 Mn1 117.27(11) . . ?
C10 N3 P1 123.51(12) . . ?
C10 N3 H3N 115.0(17) . . ?
P1 N3 H3N 121.2(17) . . ?
N3 P1 C11 102.51(9) . . ?
N3 P1 C15 104.06(8) . . ?
C11 P1 C15 113.04(8) . . ?
N3 P1 Mn1 98.49(5) . . ?
C11 P1 Mn1 117.93(6) . . ?
C15 P1 Mn1 117.12(6) . . ?

_refine_diff_density_max         0.932
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.091

