# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_test
_database_code_depnum_ccdc_archive 'CCDC 1954214'
loop_
_audit_author_name
_audit_author_address
'David Villaman'
;Pontificia Universidad Catolica de Valparaiso
Chile
;
_audit_update_record             
;
2019-09-17 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
_audit_creation_date             2019-05-22
_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         'C24 H32 Mn N4 O4, Cl'
_chemical_formula_sum            'C24 H32 Cl Mn N4 O4'
_chemical_formula_weight         530.92
_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 0.0015 0.0009 '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 0.0998 0.0984 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.2704 0.4681 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   7.5505(15)
_cell_length_b                   8.4609(17)
_cell_length_c                   19.059(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.780(5)
_cell_angle_gamma                90
_cell_volume                     1213.3(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    99.98
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.924
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1324 before and 0.0465 after correction.
The Ratio of minimum to maximum transmission is 0.8991.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            35540
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         28.016
_diffrn_reflns_theta_min         2.544
_diffrn_ambient_temperature      99.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3604
_reflns_number_total             5025
_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       ?
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.706
_refine_diff_density_min         -1.125
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         5025
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0389P)²+2.6216P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1467
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-C12
 1.469 with sigma of 0.005
 C12A-C12
 1.524 with sigma of 0.005
 N2-C12A_$1
 1.469 with sigma of 0.005
 O1A-C1 \\sim O1A-C1A
 with sigma of 0.001
 O1A-C2 \\sim O1-C2
 with sigma of 0.001
 O1-C2 \\sim O1A-C2
 with sigma of 0.001
 O1A-C1A \\sim O1-C1
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C12A) \\sim Ueq, Uanis(C12) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C1A) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O1) \\sim Ueq, Uanis(O1A) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.02
Uanis(C12A) = Uanis(C12)
Uanis(C1A) = Uanis(C1)
Uanis(O1) = Uanis(O1A)
4. Others
 Sof(O1)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=1-FVAR(1)
 Sof(O1A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=FVAR(1)
 Fixed Sof: C12(0.5) H12A(0.5) H12B(0.5) C12A(0.5) H12C(0.5) H12D(0.5)
5.a Ternary CH refined with riding coordinates:
 N2(H2)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C12A(H12C,H12D)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C8(H8)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C1A(H1AA,H1AB,H1AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.500000 0.58912(5) 0.250000 0.01825(11) Uani 1 2 d S T P B .
O2 O 0.4031(2) 0.58177(18) 0.33806(8) 0.0220(3) Uani 1 1 d . . . . .
N1 N 0.3150(2) 0.7472(2) 0.21913(9) 0.0167(3) Uani 1 1 d . . . . .
N2 N 0.3372(2) 0.4112(2) 0.21214(13) 0.0323(5) Uani 1 1 d D . . . .
H2 H 0.248190 0.387606 0.246721 0.039 Uiso 1 1 calc R . . B .
C2 C 0.2597(3) 0.9781(4) 0.44803(13) 0.0343(6) Uani 1 1 d D . . . .
C3 C 0.3212(4) 0.8401(4) 0.48331(13) 0.0392(7) Uani 1 1 d . . . . .
H3 H 0.332079 0.837733 0.533318 0.047 Uiso 1 1 calc R . . . .
C4 C 0.3656(3) 0.7088(4) 0.44631(12) 0.0327(5) Uani 1 1 d . . . . .
H4 H 0.403977 0.615861 0.471086 0.039 Uiso 1 1 calc R . . . .
C5 C 0.3552(3) 0.7097(3) 0.37203(11) 0.0206(4) Uani 1 1 d . . . . .
C6 C 0.2408(3) 0.9802(3) 0.37584(12) 0.0252(4) Uani 1 1 d . . . . .
H6 H 0.193963 1.071347 0.351815 0.030 Uiso 1 1 calc R . . . .
C7 C 0.2908(3) 0.8474(3) 0.33699(10) 0.0185(4) Uani 1 1 d . . . . .
C8 C 0.2508(2) 0.8472(2) 0.26178(10) 0.0166(3) Uani 1 1 d . . . . .
H8 H 0.171911 0.925890 0.242072 0.020 Uiso 1 1 calc R . . . .
C9 C 0.2248(3) 0.7375(3) 0.14792(11) 0.0245(4) Uani 1 1 d . . . . .
H9A H 0.313152 0.745424 0.112524 0.029 Uiso 1 1 calc R . . . .
H9B H 0.139816 0.826151 0.140249 0.029 Uiso 1 1 calc R . . . .
C10 C 0.1254(3) 0.5798(4) 0.13937(13) 0.0333(6) Uani 1 1 d . . . . .
H10A H 0.043913 0.570627 0.177257 0.040 Uiso 1 1 calc R . . . .
H10B H 0.051845 0.580856 0.093876 0.040 Uiso 1 1 calc R . . . .
C11 C 0.2442(3) 0.4356(3) 0.14157(16) 0.0400(7) Uani 1 1 d . . . . .
H11A H 0.171573 0.341163 0.128376 0.048 Uiso 1 1 calc R . . . .
H11B H 0.333160 0.448101 0.106632 0.048 Uiso 1 1 calc R . . . .
O1 O 0.2232(6) 1.1177(4) 0.4828(2) 0.0291(6) Uani 0.543(5) 1 d D U . A 2
C1 C 0.1939(8) 1.2667(6) 0.4479(3) 0.0346(9) Uani 0.543(5) 1 d D U . A 2
H1A H 0.087790 1.259862 0.414765 0.052 Uiso 0.543(5) 1 calc GR . . A 2
H1B H 0.297154 1.293153 0.422317 0.052 Uiso 0.543(5) 1 calc GR . . A 2
H1C H 0.176631 1.348949 0.482938 0.052 Uiso 0.543(5) 1 calc GR . . A 2
C12 C 0.4435(8) 0.2697(5) 0.2016(2) 0.0243(10) Uani 0.5 1 d D U . B -1
H12A H 0.518286 0.282540 0.161682 0.029 Uiso 0.5 1 calc R . . B -1
H12B H 0.368038 0.174572 0.193845 0.029 Uiso 0.5 1 calc R . . B -1
Cl1 Cl 0.000000 0.22347(9) 0.250000 0.0332(2) Uani 1 2 d S T P . .
O1A O 0.2129(7) 1.0797(5) 0.5007(2) 0.0291(6) Uani 0.457(5) 1 d D U . A 1
C12A C 0.5554(8) 0.2627(5) 0.2718(2) 0.0243(10) Uani 0.5 1 d D U . B -1
H12C H 0.475992 0.245078 0.309896 0.029 Uiso 0.5 1 calc R . . B -1
H12D H 0.637343 0.171448 0.271455 0.029 Uiso 0.5 1 calc R . . B -1
C1A C 0.1264(8) 1.2092(7) 0.4635(3) 0.0346(9) Uani 0.457(5) 1 d D U . A 1
H1AA H 0.020632 1.170606 0.435388 0.052 Uiso 0.457(5) 1 calc GR . . A 1
H1AB H 0.208192 1.257357 0.432386 0.052 Uiso 0.457(5) 1 calc GR . . A 1
H1AC H 0.091238 1.288127 0.497315 0.052 Uiso 0.457(5) 1 calc GR . . A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O2 1.8869(15) 2_655 ?
Mn1 O2 1.8869(15) . ?
Mn1 N1 1.9874(17) . ?
Mn1 N1 1.9873(17) 2_655 ?
Mn1 N2 2.037(2) 2_655 ?
Mn1 N2 2.037(2) . ?
O2 C5 1.327(3) . ?
N1 C8 1.295(2) . ?
N1 C9 1.469(3) . ?
N2 H2 1.0000 . ?
N2 C11 1.479(4) . ?
N2 C12 1.465(4) . ?
N2 C12A 1.513(4) 2_655 ?
C2 C3 1.407(5) . ?
C2 C6 1.371(3) . ?
C2 O1 1.393(3) . ?
C2 O1A 1.389(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.372(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.411(3) . ?
C5 C7 1.409(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.414(3) . ?
C7 C8 1.440(3) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.532(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.513(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
O1 C1 1.434(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C12A 1.524(4) . ?
O1A C1A 1.433(5) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 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
O2 Mn1 O2 176.22(10) 2_655 . ?
O2 Mn1 N1 94.24(7) . 2_655 ?
O2 Mn1 N1 88.31(7) . . ?
O2 Mn1 N1 88.31(7) 2_655 2_655 ?
O2 Mn1 N1 94.24(7) 2_655 . ?
O2 Mn1 N2 91.35(8) . . ?
O2 Mn1 N2 85.85(8) . 2_655 ?
O2 Mn1 N2 91.35(8) 2_655 2_655 ?
O2 Mn1 N2 85.85(8) 2_655 . ?
N1 Mn1 N1 95.41(10) 2_655 . ?
N1 Mn1 N2 172.18(7) 2_655 . ?
N1 Mn1 N2 172.18(7) . 2_655 ?
N1 Mn1 N2 90.22(8) 2_655 2_655 ?
N1 Mn1 N2 90.22(8) . . ?
N2 Mn1 N2 84.73(12) . 2_655 ?
C5 O2 Mn1 123.27(13) . . ?
C8 N1 Mn1 122.98(14) . . ?
C8 N1 C9 116.59(17) . . ?
C9 N1 Mn1 119.74(13) . . ?
Mn1 N2 H2 109.5 . . ?
C11 N2 Mn1 116.47(16) . . ?
C11 N2 H2 109.5 . . ?
C11 N2 C12A 120.4(3) . 2_655 ?
C12 N2 Mn1 109.3(3) . . ?
C12 N2 H2 109.5 . . ?
C12 N2 C11 102.3(3) . . ?
C12 N2 C12A 19.6(3) . 2_655 ?
C12A N2 Mn1 104.2(3) 2_655 . ?
C12A N2 H2 94.5 2_655 . ?
C6 C2 C3 119.5(2) . . ?
C6 C2 O1 117.3(3) . . ?
C6 C2 O1A 134.9(3) . . ?
O1 C2 C3 123.2(3) . . ?
O1A C2 C3 105.2(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
O2 C5 C4 119.4(2) . . ?
O2 C5 C7 122.73(18) . . ?
C7 C5 C4 117.9(2) . . ?
C2 C6 H6 119.8 . . ?
C2 C6 C7 120.3(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C7 C6 120.4(2) . . ?
C5 C7 C8 120.40(19) . . ?
C6 C7 C8 118.64(19) . . ?
N1 C8 C7 124.57(18) . . ?
N1 C8 H8 117.7 . . ?
C7 C8 H8 117.7 . . ?
N1 C9 H9A 109.8 . . ?
N1 C9 H9B 109.8 . . ?
N1 C9 C10 109.40(19) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C9 114.52(19) . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
N2 C11 C10 111.92(19) . . ?
N2 C11 H11A 109.2 . . ?
N2 C11 H11B 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C2 O1 C1 123.7(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C12 H12A 111.7 . . ?
N2 C12 H12B 111.7 . . ?
N2 C12 C12A 100.4(4) . . ?
H12A C12 H12B 109.5 . . ?
C12A C12 H12A 111.7 . . ?
C12A C12 H12B 111.7 . . ?
C2 O1A C1A 104.4(4) . . ?
N2 C12A C12 113.2(4) 2_655 . ?
N2 C12A H12C 108.9 2_655 . ?
N2 C12A H12D 108.9 2_655 . ?
C12 C12A H12C 108.9 . . ?
C12 C12A H12D 108.9 . . ?
H12C C12A H12D 107.8 . . ?
O1A C1A H1AA 109.5 . . ?
O1A C1A H1AB 109.5 . . ?
O1A C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 Cl1 1.00 2.34 3.136(2) 136.1 .
C6 H6 Cl1 0.95 2.66 3.545(3) 154.6 1_565
C9 H9A O1 0.99 2.76 3.376(4) 120.6 4_575

_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_test2
_database_code_depnum_ccdc_archive 'CCDC 1954216'
loop_
_audit_author_name
_audit_author_address
'David Villaman'
;Pontificia Universidad Catolica de Valparaiso
Chile
;
_audit_update_record             
;
2019-09-17 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT934_test2               
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          2 Check
RESPONSE: We checked the reflections visually in the experimental frames, there are no systematic errors. This error is due to fact that with increasing temperature, the scattering factor decreases.
;
# Added during the CSD deposition process: Tuesday 17 September 2019 03:27 PM
# end Validation Reply Form

_audit_creation_date             2019-07-15
_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         'C24 H32 Mn N4 O4, Cl'
_chemical_formula_sum            'C24 H32 Cl Mn N4 O4'
_chemical_formula_weight         530.92
_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 0.0015 0.0009 '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 0.0998 0.0984 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.2704 0.4681 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   8.0387(16)
_cell_length_b                   8.3211(16)
_cell_length_c                   19.109(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.225(5)
_cell_angle_gamma                90
_cell_volume                     1277.9(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    349.98
_cell_measurement_theta_max      25.51
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.346
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1451 before and 0.0512 after correction.
The Ratio of minimum to maximum transmission is 0.9292.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            58925
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         28.386
_diffrn_reflns_theta_min         2.562
_diffrn_ambient_temperature      349.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3089
_reflns_number_total             5832
_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       ?
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         5832
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.0535
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0471P)²+0.7633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1611
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C6(H6), C4(H4), C3(H3)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.500000 0.59229(5) 0.250000 0.04764(14) Uani 1 2 d S T P . .
Cl1 Cl 0.000000 0.22160(11) 0.250000 0.0622(2) Uani 1 2 d S T P . .
O2 O 0.4075(2) 0.58948(19) 0.33936(8) 0.0587(4) Uani 1 1 d . . . . .
N1 N 0.3065(2) 0.7448(2) 0.22008(9) 0.0509(4) Uani 1 1 d . . . . .
N2 N 0.3455(3) 0.3966(2) 0.21290(11) 0.0604(5) Uani 1 1 d . . . . .
H2 H 0.256634 0.381981 0.246648 0.072 Uiso 1 1 calc R . . . .
O1 O 0.2078(4) 1.1225(3) 0.48614(11) 0.1071(9) Uani 1 1 d . . . . .
C8 C 0.2415(3) 0.8441(3) 0.26252(11) 0.0509(5) Uani 1 1 d . . . . .
H8 H 0.163386 0.916359 0.244521 0.061 Uiso 1 1 calc R . . . .
C7 C 0.2811(3) 0.8518(3) 0.33696(11) 0.0494(5) Uani 1 1 d . . . . .
C9 C 0.2283(4) 0.7286(3) 0.14989(12) 0.0621(6) Uani 1 1 d . . . . .
H9A H 0.311819 0.742033 0.114456 0.074 Uiso 1 1 calc R . . . .
H9B H 0.144835 0.811660 0.143107 0.074 Uiso 1 1 calc R . . . .
C5 C 0.3562(3) 0.7214(3) 0.37182(11) 0.0529(5) Uani 1 1 d . . . . .
C6 C 0.2276(3) 0.9863(3) 0.37436(12) 0.0596(6) Uani 1 1 d . . . . .
H6 H 0.175694 1.070998 0.350841 0.072 Uiso 1 1 calc R . . . .
C4 C 0.3737(4) 0.7318(4) 0.44513(13) 0.0764(8) Uani 1 1 d . . . . .
H4 H 0.419990 0.646031 0.469938 0.092 Uiso 1 1 calc R . . . .
C12 C 0.4504(4) 0.2518(3) 0.21573(17) 0.0768(8) Uani 1 1 d . . . . .
H12A H 0.525453 0.251287 0.176638 0.092 Uiso 1 1 calc R . . . .
H12B H 0.381371 0.156394 0.212684 0.092 Uiso 1 1 calc R . . . .
C2 C 0.2515(4) 0.9934(4) 0.44568(13) 0.0718(7) Uani 1 1 d . . . . .
C10 C 0.1473(4) 0.5631(4) 0.14225(14) 0.0705(7) Uani 1 1 d . . . . .
H10A H 0.069404 0.549510 0.179873 0.085 Uiso 1 1 calc R . . . .
H10B H 0.083680 0.560942 0.098540 0.085 Uiso 1 1 calc R . . . .
C3 C 0.3238(4) 0.8655(4) 0.48051(13) 0.0835(9) Uani 1 1 d . . . . .
H3 H 0.338987 0.870178 0.528850 0.100 Uiso 1 1 calc R . . . .
C11 C 0.2653(4) 0.4214(3) 0.14319(14) 0.0710(7) Uani 1 1 d . . . . .
H11A H 0.204420 0.325120 0.129887 0.085 Uiso 1 1 calc R . . . .
H11B H 0.350676 0.438855 0.108895 0.085 Uiso 1 1 calc R . . . .
C1 C 0.1340(7) 1.2536(6) 0.4518(2) 0.160(3) Uani 1 1 d . . . . .
H1A H 0.038082 1.217960 0.425387 0.240 Uiso 1 1 calc GR . . . .
H1B H 0.212478 1.301172 0.420836 0.240 Uiso 1 1 calc GR . . . .
H1C H 0.100822 1.331767 0.485769 0.240 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
Mn1 O2 1.8771(15) . ?
Mn1 O2 1.8772(15) 2_655 ?
Mn1 N1 2.0782(19) . ?
Mn1 N1 2.078(2) 2_655 ?
Mn1 N2 2.159(2) 2_655 ?
Mn1 N2 2.159(2) . ?
O2 C5 1.331(3) . ?
N1 C8 1.277(3) . ?
N1 C9 1.475(3) . ?
N2 H2 0.9800 . ?
N2 C12 1.471(3) . ?
N2 C11 1.482(3) . ?
O1 C2 1.374(3) . ?
O1 C1 1.398(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.452(3) . ?
C7 C5 1.403(3) . ?
C7 C6 1.400(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.529(4) . ?
C5 C4 1.408(3) . ?
C6 H6 0.9300 . ?
C6 C2 1.374(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.366(4) . ?
C12 C12 1.518(6) 2_655 ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C2 C3 1.378(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.513(4) . ?
C3 H3 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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
O2 Mn1 O2 178.57(10) . 2_655 ?
O2 Mn1 N1 93.80(8) 2_655 . ?
O2 Mn1 N1 87.07(7) . . ?
O2 Mn1 N1 87.08(7) 2_655 2_655 ?
O2 Mn1 N1 93.80(8) . 2_655 ?
O2 Mn1 N2 85.89(7) 2_655 . ?
O2 Mn1 N2 85.89(7) . 2_655 ?
O2 Mn1 N2 93.03(8) 2_655 2_655 ?
O2 Mn1 N2 93.03(8) . . ?
N1 Mn1 N1 104.74(11) 2_655 . ?
N1 Mn1 N2 166.67(8) . 2_655 ?
N1 Mn1 N2 87.02(8) 2_655 2_655 ?
N1 Mn1 N2 87.03(8) . . ?
N1 Mn1 N2 166.67(8) 2_655 . ?
N2 Mn1 N2 82.06(12) . 2_655 ?
C5 O2 Mn1 123.12(14) . . ?
C8 N1 Mn1 122.30(15) . . ?
C8 N1 C9 117.7(2) . . ?
C9 N1 Mn1 119.75(15) . . ?
Mn1 N2 H2 107.4 . . ?
C12 N2 Mn1 106.26(16) . . ?
C12 N2 H2 107.4 . . ?
C12 N2 C11 112.7(2) . . ?
C11 N2 Mn1 115.23(16) . . ?
C11 N2 H2 107.4 . . ?
C2 O1 C1 117.2(2) . . ?
N1 C8 H8 117.7 . . ?
N1 C8 C7 124.5(2) . . ?
C7 C8 H8 117.7 . . ?
C5 C7 C8 120.9(2) . . ?
C6 C7 C8 118.2(2) . . ?
C6 C7 C5 120.6(2) . . ?
N1 C9 H9A 109.7 . . ?
N1 C9 H9B 109.7 . . ?
N1 C9 C10 110.0(2) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
O2 C5 C7 123.5(2) . . ?
O2 C5 C4 119.3(2) . . ?
C7 C5 C4 117.3(2) . . ?
C7 C6 H6 119.9 . . ?
C2 C6 C7 120.2(2) . . ?
C2 C6 H6 119.9 . . ?
C5 C4 H4 119.4 . . ?
C3 C4 C5 121.2(3) . . ?
C3 C4 H4 119.4 . . ?
N2 C12 C12 108.8(2) . 2_655 ?
N2 C12 H12A 109.9 . . ?
N2 C12 H12B 109.9 . . ?
C12 C12 H12A 109.9 2_655 . ?
C12 C12 H12B 109.9 2_655 . ?
H12A C12 H12B 108.3 . . ?
O1 C2 C3 116.3(2) . . ?
C6 C2 O1 124.1(3) . . ?
C6 C2 C3 119.6(3) . . ?
C9 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 C9 115.8(2) . . ?
C11 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
N2 C11 C10 112.3(2) . . ?
N2 C11 H11A 109.1 . . ?
N2 C11 H11B 109.1 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 Cl1 0.98 2.46 3.228(2) 135.1 .
C8 H8 Cl1 0.93 2.86 3.698(2) 150.1 1_565
C6 H6 Cl1 0.93 2.68 3.556(3) 158.0 1_565

_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_test_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1954215'
loop_
_audit_author_name
_audit_author_address
'David Villaman'
;Pontificia Universidad Catolica de Valparaiso
Chile
;
_audit_update_record             
;
2019-09-17 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT934_test                
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          3 Check
RESPONSE: We checked the reflections visually in the experimental frames, there are no systematic errors. This error is due to fact that with increasing temperature, the scattering factor decreases.
;
# Added during the CSD deposition process: Tuesday 17 September 2019 03:27 PM
# end Validation Reply Form

_audit_creation_date             2019-07-15
_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         'C24 H32 Mn N4 O4, Cl'
_chemical_formula_sum            'C24 H32 Cl Mn N4 O4'
_chemical_formula_weight         530.92
_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 0.0015 0.0009 '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 0.0998 0.0984 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.2704 0.4681 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   7.8657(4)
_cell_length_b                   8.3573(5)
_cell_length_c                   19.1322(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.729(2)
_cell_angle_gamma                90
_cell_volume                     1256.25(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    289.99
_cell_measurement_theta_max      24.86
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1477 before and 0.0523 after correction.
The Ratio of minimum to maximum transmission is 0.9249.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            69985
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         28.390
_diffrn_reflns_theta_min         2.555
_diffrn_ambient_temperature      289.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3432
_reflns_number_total             6078
_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       ?
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         6078
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.102
_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)+(0.0495P)²+0.4322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1458
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C8(H8)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.500000 0.58971(4) 0.250000 0.04056(11) Uani 1 2 d S T P . .
O1 O 0.7879(3) 1.1126(3) 0.01263(9) 0.0903(6) Uani 1 1 d . . . . .
O2 O 0.59361(18) 0.58497(15) 0.16151(7) 0.0497(3) Uani 1 1 d . . . . .
N1 N 0.6894(2) 0.74506(17) 0.28026(7) 0.0449(3) Uani 1 1 d . . . . .
N2 N 0.6575(2) 0.40156(18) 0.28730(9) 0.0508(3) Uani 1 1 d . . . . .
H2 H 0.747053 0.387656 0.253910 0.061 Uiso 1 1 calc R . . . .
C1 C 0.8550(6) 1.2482(4) 0.04738(17) 0.1371(18) Uani 1 1 d . . . . .
H1A H 0.878447 1.329488 0.013717 0.206 Uiso 1 1 calc GR . . . .
H1B H 0.958330 1.219854 0.073111 0.206 Uiso 1 1 calc GR . . . .
H1C H 0.773925 1.288059 0.079081 0.206 Uiso 1 1 calc GR . . . .
C2 C 0.7451(3) 0.9858(3) 0.05388(10) 0.0612(5) Uani 1 1 d . . . . .
C3 C 0.6765(3) 0.8535(3) 0.01898(10) 0.0711(6) Uani 1 1 d . . . . .
H3 H 0.662728 0.855176 -0.029558 0.085 Uiso 1 1 calc R . . . .
C4 C 0.6289(3) 0.7206(3) 0.05492(10) 0.0652(6) Uani 1 1 d . . . . .
H4 H 0.585979 0.632344 0.030302 0.078 Uiso 1 1 calc R . . . .
C5 C 0.6437(2) 0.7151(2) 0.12847(9) 0.0458(4) Uani 1 1 d . . . . .
C6 C 0.7673(2) 0.9828(2) 0.12544(9) 0.0512(4) Uani 1 1 d . . . . .
H6 H 0.817059 1.069547 0.148989 0.061 Uiso 1 1 calc R . . . .
C7 C 0.7149(2) 0.8484(2) 0.16321(8) 0.0432(3) Uani 1 1 d . . . . .
C8 C 0.7545(2) 0.8441(2) 0.23777(9) 0.0452(4) Uani 1 1 d . . . . .
H8 H 0.832575 0.918229 0.256230 0.054 Uiso 1 1 calc R . . . .
C9 C 0.7722(3) 0.7314(2) 0.35081(9) 0.0539(4) Uani 1 1 d . . . . .
H9A H 0.687727 0.742266 0.385830 0.065 Uiso 1 1 calc R . . . .
H9B H 0.855157 0.816470 0.357974 0.065 Uiso 1 1 calc R . . . .
C10 C 0.8604(3) 0.5690(3) 0.35864(11) 0.0602(5) Uani 1 1 d . . . . .
H10A H 0.938556 0.557471 0.321256 0.072 Uiso 1 1 calc R . . . .
H10B H 0.927342 0.568139 0.402544 0.072 Uiso 1 1 calc R . . . .
C11 C 0.7425(3) 0.4257(3) 0.35718(11) 0.0598(5) Uani 1 1 d . . . . .
H11A H 0.807356 0.330692 0.370170 0.072 Uiso 1 1 calc R . . . .
H11B H 0.656836 0.440870 0.391400 0.072 Uiso 1 1 calc R . . . .
C12 C 0.5515(3) 0.2551(2) 0.28426(13) 0.0641(5) Uani 1 1 d . . . . .
H12A H 0.476453 0.253615 0.323028 0.077 Uiso 1 1 calc R . . . .
H12B H 0.623490 0.160897 0.287468 0.077 Uiso 1 1 calc R . . . .
Cl1 Cl 1.000000 1.22278(8) 0.250000 0.05307(16) Uani 1 2 d S T 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
Mn1 O2 1.8785(12) . ?
Mn1 O2 1.8786(12) 2_655 ?
Mn1 N1 2.0389(15) 2_655 ?
Mn1 N1 2.0389(15) . ?
Mn1 N2 2.1054(15) . ?
Mn1 N2 2.1054(16) 2_655 ?
O1 C1 1.404(4) . ?
O1 C2 1.373(3) . ?
O2 C5 1.327(2) . ?
N1 C8 1.284(2) . ?
N1 C9 1.475(2) . ?
N2 H2 0.9800 . ?
N2 C11 1.480(3) . ?
N2 C12 1.480(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.387(3) . ?
C2 C6 1.372(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.407(3) . ?
C5 C7 1.401(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.408(2) . ?
C7 C8 1.446(2) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.528(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.514(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C12 1.508(5) 2_655 ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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
O2 Mn1 O2 177.58(8) . 2_655 ?
O2 Mn1 N1 94.01(6) 2_655 . ?
O2 Mn1 N1 87.53(6) . . ?
O2 Mn1 N1 87.53(6) 2_655 2_655 ?
O2 Mn1 N1 94.01(6) . 2_655 ?
O2 Mn1 N2 85.89(6) 2_655 . ?
O2 Mn1 N2 85.89(6) . 2_655 ?
O2 Mn1 N2 92.30(6) 2_655 2_655 ?
O2 Mn1 N2 92.30(6) . . ?
N1 Mn1 N1 100.90(8) 2_655 . ?
N1 Mn1 N2 169.10(6) . 2_655 ?
N1 Mn1 N2 88.23(6) 2_655 2_655 ?
N1 Mn1 N2 169.10(6) 2_655 . ?
N1 Mn1 N2 88.23(6) . . ?
N2 Mn1 N2 83.36(9) . 2_655 ?
C2 O1 C1 116.61(19) . . ?
C5 O2 Mn1 123.37(11) . . ?
C8 N1 Mn1 122.61(12) . . ?
C8 N1 C9 117.19(16) . . ?
C9 N1 Mn1 119.71(12) . . ?
Mn1 N2 H2 107.3 . . ?
C11 N2 Mn1 115.94(12) . . ?
C11 N2 H2 107.3 . . ?
C11 N2 C12 112.20(16) . . ?
C12 N2 Mn1 106.44(12) . . ?
C12 N2 H2 107.3 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 116.04(19) . . ?
C6 C2 O1 124.4(2) . . ?
C6 C2 C3 119.60(19) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.97(19) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
O2 C5 C4 119.41(17) . . ?
O2 C5 C7 123.16(15) . . ?
C7 C5 C4 117.41(17) . . ?
C2 C6 H6 120.0 . . ?
C2 C6 C7 120.01(18) . . ?
C7 C6 H6 120.0 . . ?
C5 C7 C6 120.76(16) . . ?
C5 C7 C8 120.71(16) . . ?
C6 C7 C8 118.15(16) . . ?
N1 C8 C7 124.54(16) . . ?
N1 C8 H8 117.7 . . ?
C7 C8 H8 117.7 . . ?
N1 C9 H9A 109.7 . . ?
N1 C9 H9B 109.7 . . ?
N1 C9 C10 109.68(15) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 C9 115.22(18) . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
N2 C11 C10 112.01(16) . . ?
N2 C11 H11A 109.2 . . ?
N2 C11 H11B 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N2 C12 C12 108.21(15) . 2_655 ?
N2 C12 H12A 110.1 . . ?
N2 C12 H12B 110.1 . . ?
C12 C12 H12A 110.1 2_655 . ?
C12 C12 H12B 110.1 2_655 . ?
H12A C12 H12B 108.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 Cl1 0.98 2.42 3.1909(16) 134.7 1_545
C6 H6 Cl1 0.93 2.68 3.555(2) 157.1 .

_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_test_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1954217'
loop_
_audit_author_name
_audit_author_address
'David Villaman'
;Pontificia Universidad Catolica de Valparaiso
Chile
;
_audit_update_record             
;
2019-09-17 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT934_test                
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          3 Check
RESPONSE: We checked the reflections visually in the experimental frames, there are no systematic errors. This error is due to fact that with increasing temperature, the scattering factor decreases.
;
# Added during the CSD deposition process: Tuesday 17 September 2019 03:27 PM
# end Validation Reply Form

_audit_creation_date             2019-05-22
_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         'C24 H32 Mn N4 O4, Cl'
_chemical_formula_sum            'C24 H32 Cl Mn N4 O4'
_chemical_formula_weight         530.92
_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 0.0015 0.0009 '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 0.0998 0.0984 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.2704 0.4681 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   8.1041(17)
_cell_length_b                   8.3084(17)
_cell_length_c                   19.127(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.843(5)
_cell_angle_gamma                90
_cell_volume                     1287.7(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    400
_cell_measurement_theta_max      21.44
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.343
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1411 before and 0.0588 after correction.
The Ratio of minimum to maximum transmission is 0.9433.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            72579
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_min         2.563
_diffrn_ambient_temperature      400
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2548
_reflns_number_total             5846
_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       ?
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         5846
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1389
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+0.7127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1641
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C8(H8)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.500000 0.59485(6) 0.250000 0.05896(17) Uani 1 2 d S T P . .
O1 O 0.7941(4) 1.1262(4) 0.01471(12) 0.1236(10) Uani 1 1 d . . . . .
O2 O 0.5923(2) 0.5933(2) 0.16064(9) 0.0707(5) Uani 1 1 d . . . . .
N1 N 0.6943(3) 0.7466(2) 0.27994(10) 0.0614(5) Uani 1 1 d . . . . .
N2 N 0.6533(3) 0.3976(3) 0.28725(12) 0.0720(6) Uani 1 1 d . . . . .
H2 H 0.741836 0.382829 0.253491 0.086 Uiso 1 1 calc R . . . .
C1 C 0.8690(7) 1.2565(6) 0.0485(2) 0.177(3) Uani 1 1 d . . . . .
H1A H 0.905814 1.332590 0.014314 0.266 Uiso 1 1 calc GR . . . .
H1B H 0.961707 1.219246 0.075761 0.266 Uiso 1 1 calc GR . . . .
H1C H 0.790869 1.307333 0.078605 0.266 Uiso 1 1 calc GR . . . .
C2 C 0.7499(4) 0.9969(4) 0.05514(14) 0.0841(9) Uani 1 1 d . . . . .
C3 C 0.6773(5) 0.8704(5) 0.02013(15) 0.0959(10) Uani 1 1 d . . . . .
H3 H 0.662238 0.875973 -0.028108 0.115 Uiso 1 1 calc R . . . .
C4 C 0.6269(4) 0.7363(4) 0.05537(14) 0.0879(9) Uani 1 1 d . . . . .
H4 H 0.580142 0.651100 0.030529 0.106 Uiso 1 1 calc R . . . .
C5 C 0.6443(3) 0.7249(3) 0.12838(12) 0.0631(6) Uani 1 1 d . . . . .
C6 C 0.7740(3) 0.9884(4) 0.12597(13) 0.0712(7) Uani 1 1 d . . . . .
H6 H 0.826450 1.072534 0.149465 0.085 Uiso 1 1 calc R . . . .
C7 C 0.7202(3) 0.8535(3) 0.16336(12) 0.0597(5) Uani 1 1 d . . . . .
C8 C 0.7595(3) 0.8455(3) 0.23730(12) 0.0604(5) Uani 1 1 d . . . . .
H8 H 0.837672 0.917224 0.255003 0.072 Uiso 1 1 calc R . . . .
C9 C 0.7706(4) 0.7292(3) 0.34995(13) 0.0746(7) Uani 1 1 d . . . . .
H9A H 0.687323 0.743142 0.385353 0.090 Uiso 1 1 calc R . . . .
H9B H 0.853955 0.811711 0.356815 0.090 Uiso 1 1 calc R . . . .
C10 C 0.8493(4) 0.5636(4) 0.35756(15) 0.0849(9) Uani 1 1 d . . . . .
H10A H 0.927168 0.549571 0.320010 0.102 Uiso 1 1 calc R . . . .
H10B H 0.911626 0.561080 0.401233 0.102 Uiso 1 1 calc R . . . .
C11 C 0.7318(4) 0.4219(4) 0.35658(15) 0.0842(8) Uani 1 1 d . . . . .
H11A H 0.791782 0.325257 0.369762 0.101 Uiso 1 1 calc R . . . .
H11B H 0.646775 0.439451 0.390920 0.101 Uiso 1 1 calc R . . . .
C12 C 0.5489(4) 0.2530(3) 0.28429(18) 0.0918(9) Uani 1 1 d . . . . .
H12A H 0.474043 0.252433 0.323386 0.110 Uiso 1 1 calc R . . . .
H12B H 0.617235 0.157257 0.287272 0.110 Uiso 1 1 calc R . . . .
Cl1 Cl 1.000000 0.22353(12) 0.250000 0.0750(3) Uani 1 2 d S T 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
Mn1 O2 1.8757(17) . ?
Mn1 O2 1.8757(17) 2_655 ?
Mn1 N1 2.091(2) . ?
Mn1 N1 2.091(2) 2_655 ?
Mn1 N2 2.171(2) . ?
Mn1 N2 2.171(2) 2_655 ?
O1 C1 1.395(5) . ?
O1 C2 1.375(3) . ?
O2 C5 1.327(3) . ?
N1 C8 1.278(3) . ?
N1 C9 1.474(3) . ?
N2 H2 0.9800 . ?
N2 C11 1.476(4) . ?
N2 C12 1.470(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.374(4) . ?
C2 C6 1.368(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.405(3) . ?
C5 C7 1.399(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.403(3) . ?
C7 C8 1.447(3) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.523(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.514(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C12 1.523(7) 2_655 ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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
O2 Mn1 O2 179.19(11) . 2_655 ?
O2 Mn1 N1 86.85(7) 2_655 2_655 ?
O2 Mn1 N1 93.64(8) 2_655 . ?
O2 Mn1 N1 93.64(8) . 2_655 ?
O2 Mn1 N1 86.85(7) . . ?
O2 Mn1 N2 93.43(9) 2_655 2_655 ?
O2 Mn1 N2 85.96(8) 2_655 . ?
O2 Mn1 N2 93.43(8) . . ?
O2 Mn1 N2 85.96(8) . 2_655 ?
N1 Mn1 N1 105.82(11) 2_655 . ?
N1 Mn1 N2 86.58(8) 2_655 2_655 ?
N1 Mn1 N2 86.58(8) . . ?
N1 Mn1 N2 166.04(8) 2_655 . ?
N1 Mn1 N2 166.04(8) . 2_655 ?
N2 Mn1 N2 81.93(13) 2_655 . ?
C2 O1 C1 117.5(3) . . ?
C5 O2 Mn1 123.47(15) . . ?
C8 N1 Mn1 122.00(16) . . ?
C8 N1 C9 118.1(2) . . ?
C9 N1 Mn1 119.60(16) . . ?
Mn1 N2 H2 107.4 . . ?
C11 N2 Mn1 115.37(17) . . ?
C11 N2 H2 107.4 . . ?
C12 N2 Mn1 106.16(17) . . ?
C12 N2 H2 107.4 . . ?
C12 N2 C11 112.8(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 O1 115.9(3) . . ?
C6 C2 O1 124.3(3) . . ?
C6 C2 C3 119.8(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
O2 C5 C4 119.3(2) . . ?
O2 C5 C7 123.2(2) . . ?
C7 C5 C4 117.4(2) . . ?
C2 C6 H6 119.8 . . ?
C2 C6 C7 120.3(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C7 C6 120.3(2) . . ?
C5 C7 C8 121.4(2) . . ?
C6 C7 C8 118.0(2) . . ?
N1 C8 C7 124.5(2) . . ?
N1 C8 H8 117.7 . . ?
C7 C8 H8 117.7 . . ?
N1 C9 H9A 109.6 . . ?
N1 C9 H9B 109.6 . . ?
N1 C9 C10 110.2(2) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C9 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 C9 116.0(3) . . ?
C11 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
N2 C11 C10 112.4(2) . . ?
N2 C11 H11A 109.1 . . ?
N2 C11 H11B 109.1 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
N2 C12 C12 109.0(2) . 2_655 ?
N2 C12 H12A 109.9 . . ?
N2 C12 H12B 109.9 . . ?
C12 C12 H12A 109.9 2_655 . ?
C12 C12 H12B 109.9 2_655 . ?
H12A C12 H12B 108.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 Cl1 0.98 2.48 3.248(2) 135.3 .
C6 H6 Cl1 0.93 2.68 3.559(3) 158.5 1_565

_olex2_submission_special_instructions 'No special instructions were received'
