# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_al_st4f_0m
_database_code_depnum_ccdc_archive 'CCDC 2032124'
loop_
_audit_author_name
_audit_author_address
'Lise-Marie Chamoreau'
;Sorbonne Universite, CNRS, IPCM 
France
;
_audit_update_record             
;
2020-11-19 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;
_audit_creation_date             2019-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H21 Co Cu N3 O8'
_chemical_formula_sum            'C16 H21 Co Cu N3 O8'
_chemical_formula_weight         505.83
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.3056(4)
_cell_length_b                   8.3802(2)
_cell_length_c                   15.8983(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.2040(10)
_cell_angle_gamma                90
_cell_volume                     2018.31(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9422
_cell_measurement_temperature    200
_cell_measurement_theta_max      67.68
_cell_measurement_theta_min      5.62
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.180
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.4152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption 
correction. wR2(int) was 0.1084 before and 0.0449 after 
correction. The Ratio of minimum to maximum transmission is 0.5514. 
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27128
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.725
_diffrn_reflns_theta_min         5.841
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   micro-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3541
_reflns_number_total             3637
_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 (BRUKER)'
_computing_data_collection       'APEX2 (BRUKER)'
_computing_data_reduction        'SAINT (BRUKER)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3637
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0267
_refine_ls_restrained_S_all      1.018
_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)+(0.0456P)²+1.2413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0719
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C14(H14)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual-space
_atom_sites_solution_secondary   difmap
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
Co1 Co 0.22561(2) 0.67035(4) 0.45835(2) 0.01613(10) Uani 1 1 d . . . . .
Cu1 Cu 0.21453(2) 0.88121(3) 0.62260(2) 0.01814(9) Uani 1 1 d . . . . .
O1 O 0.14424(8) 0.95625(16) 0.71227(8) 0.0218(3) Uani 1 1 d . . . . .
O2 O 0.15177(8) 0.94536(16) 0.85334(8) 0.0205(3) Uani 1 1 d . . . . .
O3 O 0.30901(8) 0.79415(17) 0.86526(8) 0.0202(3) Uani 1 1 d . . . . .
O4 O 0.30116(8) 0.78999(16) 0.55617(8) 0.0194(3) Uani 1 1 d . . . . .
O5 O 0.14663(10) 1.00976(17) 0.53891(8) 0.0270(3) Uani 1 1 d . . . . .
O6 O 0.15969(9) 0.87894(16) 0.41815(8) 0.0242(3) Uani 1 1 d . . . . .
O7 O 0.13536(10) 0.63646(17) 0.54742(9) 0.0263(3) Uani 1 1 d . . . . .
O8 O 0.27831(9) 0.44750(17) 0.49735(9) 0.0270(3) Uani 1 1 d . . . . .
N1 N 0.29170(10) 0.79959(19) 0.71749(9) 0.0181(3) Uani 1 1 d . . . . .
N2 N 0.07818(11) 0.4612(2) 0.63418(11) 0.0245(4) Uani 1 1 d . . . . .
N3 N 0.34395(12) 0.2109(2) 0.48010(13) 0.0349(4) Uani 1 1 d . . . . .
C1 C 0.18102(11) 0.9164(2) 0.78593(11) 0.0169(4) Uani 1 1 d . . . . .
C2 C 0.26953(12) 0.8276(2) 0.79262(12) 0.0164(4) Uani 1 1 d . . . . .
C3 C 0.36658(12) 0.7213(2) 0.69626(11) 0.0183(4) Uani 1 1 d . . . . .
C4 C 0.43380(13) 0.6507(2) 0.75159(13) 0.0257(4) Uani 1 1 d . . . . .
H4 H 0.4327 0.6538 0.8112 0.031 Uiso 1 1 calc R . . . .
C5 C 0.50257(13) 0.5757(3) 0.71926(14) 0.0303(5) Uani 1 1 d . . . . .
H5 H 0.5483 0.5254 0.7567 0.036 Uiso 1 1 calc R . . . .
C6 C 0.50482(13) 0.5739(3) 0.63228(14) 0.0293(5) Uani 1 1 d . . . . .
H6 H 0.5522 0.5221 0.6107 0.035 Uiso 1 1 calc R . . . .
C7 C 0.43880(13) 0.6467(3) 0.57644(13) 0.0261(4) Uani 1 1 d . . . . .
H7 H 0.4417 0.6468 0.5172 0.031 Uiso 1 1 calc R . . . .
C8 C 0.36843(12) 0.7196(2) 0.60762(11) 0.0185(4) Uani 1 1 d . . . . .
C9 C 0.13100(12) 0.9896(2) 0.45887(12) 0.0217(4) Uani 1 1 d . . . . .
C10 C 0.07199(16) 1.1130(3) 0.41103(13) 0.0337(5) Uani 1 1 d . . . . .
H10A H 0.1082 1.1933 0.3874 0.051 Uiso 1 1 calc GR . . . .
H10B H 0.0364 1.1648 0.4498 0.051 Uiso 1 1 calc GR . . . .
H10C H 0.0329 1.0614 0.3647 0.051 Uiso 1 1 calc GR . . . .
C11 C 0.11301(14) 0.4999(3) 0.56623(13) 0.0280(4) Uani 1 1 d . . . . .
H11 H 0.1219 0.4162 0.5280 0.034 Uiso 1 1 calc R . . . .
C12 C 0.06199(15) 0.5804(3) 0.69668(13) 0.0292(4) Uani 1 1 d . . . . .
H12A H 0.1068 0.5709 0.7470 0.044 Uiso 1 1 calc GR . . . .
H12B H 0.0033 0.5634 0.7130 0.044 Uiso 1 1 calc GR . . . .
H12C H 0.0649 0.6872 0.6721 0.044 Uiso 1 1 calc GR . . . .
C13 C 0.05677(17) 0.2964(3) 0.65206(17) 0.0400(6) Uani 1 1 d . . . . .
H13A H 0.0742 0.2267 0.6079 0.060 Uiso 1 1 calc GR . . . .
H13B H -0.0069 0.2867 0.6529 0.060 Uiso 1 1 calc GR . . . .
H13C H 0.0886 0.2650 0.7075 0.060 Uiso 1 1 calc GR . . . .
C14 C 0.29946(14) 0.3386(2) 0.45191(14) 0.0270(4) Uani 1 1 d . . . . .
H14 H 0.2823 0.3480 0.3923 0.032 Uiso 1 1 calc R . . . .
C15 C 0.3745(2) 0.1920(3) 0.5702(2) 0.0574(8) Uani 1 1 d . . . . .
H15A H 0.4380 0.2138 0.5816 0.086 Uiso 1 1 calc GR . . . .
H15B H 0.3632 0.0825 0.5875 0.086 Uiso 1 1 calc GR . . . .
H15C H 0.3430 0.2669 0.6025 0.086 Uiso 1 1 calc GR . . . .
C16 C 0.36707(19) 0.0875(3) 0.4225(2) 0.0532(7) Uani 1 1 d . . . . .
H16A H 0.3384 0.1104 0.3647 0.080 Uiso 1 1 calc GR . . . .
H16B H 0.3471 -0.0165 0.4406 0.080 Uiso 1 1 calc GR . . . .
H16C H 0.4312 0.0855 0.4236 0.080 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
Co1 O2 2.1133(13) 4_575 ?
Co1 O3 2.1089(13) 4_575 ?
Co1 O4 2.0611(13) . ?
Co1 O6 2.0731(14) . ?
Co1 O7 2.1335(14) . ?
Co1 O8 2.0930(14) . ?
Cu1 O1 2.0058(13) . ?
Cu1 O4 1.9639(13) . ?
Cu1 O5 1.9016(13) . ?
Cu1 N1 1.9053(15) . ?
O1 C1 1.269(2) . ?
O2 Co1 2.1133(13) 4_576 ?
O2 C1 1.243(2) . ?
O3 Co1 2.1089(13) 4_576 ?
O3 C2 1.256(2) . ?
O4 C8 1.355(2) . ?
O5 C9 1.272(2) . ?
O6 C9 1.246(2) . ?
O7 C11 1.243(3) . ?
O8 C14 1.235(3) . ?
N1 C2 1.309(2) . ?
N1 C3 1.403(2) . ?
N2 C11 1.312(3) . ?
N2 C12 1.455(3) . ?
N2 C13 1.457(3) . ?
N3 C14 1.313(3) . ?
N3 C15 1.451(3) . ?
N3 C16 1.458(3) . ?
C1 C2 1.536(2) . ?
C3 C4 1.387(3) . ?
C3 C8 1.414(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(3) . ?
C9 C10 1.506(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 0.9500 . ?
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 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Co1 O7 98.01(5) 4_575 . ?
O3 Co1 O2 79.59(5) 4_575 4_575 ?
O3 Co1 O7 176.96(5) 4_575 . ?
O4 Co1 O2 176.88(5) . 4_575 ?
O4 Co1 O3 97.49(5) . 4_575 ?
O4 Co1 O6 91.06(5) . . ?
O4 Co1 O7 84.87(5) . . ?
O4 Co1 O8 93.41(5) . . ?
O6 Co1 O2 87.79(5) . 4_575 ?
O6 Co1 O3 88.94(5) . 4_575 ?
O6 Co1 O7 89.10(6) . . ?
O6 Co1 O8 173.60(6) . . ?
O8 Co1 O2 87.98(5) . 4_575 ?
O8 Co1 O3 95.02(6) . 4_575 ?
O8 Co1 O7 86.74(6) . . ?
O4 Cu1 O1 167.41(5) . . ?
O5 Cu1 O1 91.41(6) . . ?
O5 Cu1 O4 100.83(6) . . ?
O5 Cu1 N1 166.53(7) . . ?
N1 Cu1 O1 83.37(6) . . ?
N1 Cu1 O4 84.04(6) . . ?
C1 O1 Cu1 111.17(11) . . ?
C1 O2 Co1 111.96(11) . 4_576 ?
C2 O3 Co1 110.72(11) . 4_576 ?
Cu1 O4 Co1 104.24(6) . . ?
C8 O4 Co1 122.68(11) . . ?
C8 O4 Cu1 110.97(10) . . ?
C9 O5 Cu1 129.08(13) . . ?
C9 O6 Co1 131.24(12) . . ?
C11 O7 Co1 120.58(13) . . ?
C14 O8 Co1 127.43(14) . . ?
C2 N1 Cu1 116.50(13) . . ?
C2 N1 C3 129.08(16) . . ?
C3 N1 Cu1 114.38(11) . . ?
C11 N2 C12 121.42(17) . . ?
C11 N2 C13 121.63(18) . . ?
C12 N2 C13 116.92(17) . . ?
C14 N3 C15 120.3(2) . . ?
C14 N3 C16 121.7(2) . . ?
C15 N3 C16 118.0(2) . . ?
O1 C1 C2 117.51(16) . . ?
O2 C1 O1 125.27(16) . . ?
O2 C1 C2 117.22(16) . . ?
O3 C2 N1 130.23(17) . . ?
O3 C2 C1 118.39(16) . . ?
N1 C2 C1 111.38(15) . . ?
N1 C3 C8 112.18(16) . . ?
C4 C3 N1 127.18(17) . . ?
C4 C3 C8 120.64(17) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.48(19) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.15(19) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.87(18) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.73(19) . . ?
C8 C7 H7 120.1 . . ?
O4 C8 C3 118.42(16) . . ?
O4 C8 C7 122.46(17) . . ?
C7 C8 C3 119.12(18) . . ?
O5 C9 C10 115.29(18) . . ?
O6 C9 O5 126.08(18) . . ?
O6 C9 C10 118.63(17) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O7 C11 N2 125.73(19) . . ?
O7 C11 H11 117.1 . . ?
N2 C11 H11 117.1 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 C14 N3 124.7(2) . . ?
O8 C14 H14 117.7 . . ?
N3 C14 H14 117.7 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_al_st232_c_0m-desordrecomn
_database_code_depnum_ccdc_archive 'CCDC 2032126'
loop_
_audit_author_name
_audit_author_address
'Lise-Marie Chamoreau'
;Sorbonne Universite, CNRS, IPCM 
France
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;
_audit_creation_date             2019-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H21 Co0.78 Cu Mn0.22 N3 O8'
_chemical_formula_sum            'C16 H21 Co0.78 Cu Mn0.22 N3 O8'
_chemical_formula_weight         504.94
_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 0.0181 0.0091 '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'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.2626(4)
_cell_length_b                   8.4325(2)
_cell_length_c                   16.0027(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.2690(10)
_cell_angle_gamma                90
_cell_volume                     2038.17(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    200
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      2.93
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.803
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1058 before and 0.0416 after correction. The Ratio of minimum to maximum transmission is 0.5427. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1030
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17152
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.294
_diffrn_reflns_theta_min         5.859
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   microfocus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3437
_reflns_number_total             3725
_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 (Bruker)'
_computing_data_collection       'APEX2 (Bruker)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_molecular_graphics    'DIAMOND (Brandenburg)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXt (Sheldrick, 2015)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3725
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.047
_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)+(0.0357P)²+1.4664P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0723
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{Co1, Mn1}
3. Uiso/Uaniso restraints and constraints
Uanis(Co1) = Uanis(Mn1)
4. Others
 Sof(Mn1)=1-FVAR(1)
 Sof(Co1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C14(H14)
5.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Cu1 Cu 0.78443(2) 0.88297(4) 0.37825(2) 0.02230(10) Uani 1 1 d . . . . .
Co1 Co 0.77504(2) 0.66957(4) 0.54249(2) 0.02009(11) Uani 0.78(3) 1 d . . P A 1
O1 O 0.85532(9) 0.95747(19) 0.28965(9) 0.0262(3) Uani 1 1 d . . . . .
O2 O 0.84868(9) 0.94662(19) 0.14953(8) 0.0254(3) Uani 1 1 d . . . . .
O3 O 0.69112(9) 0.79461(19) 0.13699(8) 0.0239(3) Uani 1 1 d . . . . .
O4 O 0.69794(9) 0.79008(19) 0.44406(8) 0.0236(3) Uani 1 1 d . . . . .
O5 O 0.85288(11) 1.0113(2) 0.46147(9) 0.0313(4) Uani 1 1 d . . . . .
O6 O 0.84257(11) 0.8802(2) 0.58130(9) 0.0295(4) Uani 1 1 d . . . . .
O7 O 0.86601(11) 0.6334(2) 0.45262(10) 0.0313(4) Uani 1 1 d . . . . .
O8 O 0.72180(11) 0.4432(2) 0.50465(10) 0.0330(4) Uani 1 1 d . . . . .
N1 N 0.70756(11) 0.8015(2) 0.28380(10) 0.0211(4) Uani 1 1 d . . . . .
N2 N 0.92033(13) 0.4602(2) 0.36422(12) 0.0300(4) Uani 1 1 d . . . . .
N3 N 0.65546(14) 0.2080(3) 0.52187(15) 0.0411(5) Uani 1 1 d . . . . .
C1 C 0.81909(13) 0.9180(3) 0.21661(12) 0.0212(4) Uani 1 1 d . . . . .
C2 C 0.73018(13) 0.8289(2) 0.20900(12) 0.0198(4) Uani 1 1 d . . . . .
C3 C 0.63267(13) 0.7223(3) 0.30454(13) 0.0220(4) Uani 1 1 d . . . . .
C4 C 0.56538(15) 0.6514(3) 0.24925(14) 0.0310(5) Uani 1 1 d . . . . .
H4 H 0.5664 0.6550 0.1913 0.037 Uiso 1 1 calc R . . . .
C5 C 0.49675(15) 0.5753(3) 0.28094(16) 0.0356(6) Uani 1 1 d . . . . .
H5 H 0.4522 0.5258 0.2443 0.043 Uiso 1 1 calc R . . . .
C6 C 0.49443(15) 0.5729(3) 0.36720(16) 0.0341(5) Uani 1 1 d . . . . .
H6 H 0.4480 0.5220 0.3880 0.041 Uiso 1 1 calc R . . . .
C7 C 0.56015(15) 0.6453(3) 0.42269(14) 0.0307(5) Uani 1 1 d . . . . .
H7 H 0.5572 0.6442 0.4803 0.037 Uiso 1 1 calc R . . . .
C8 C 0.63071(14) 0.7197(3) 0.39244(13) 0.0227(4) Uani 1 1 d . . . . .
C9 C 0.87010(14) 0.9914(3) 0.54080(13) 0.0259(5) Uani 1 1 d . . . . .
C10 C 0.92935(18) 1.1145(3) 0.58768(15) 0.0376(6) Uani 1 1 d . . . . .
H10A H 0.9663 1.1605 0.5504 0.056 Uiso 1 1 calc GR . . . .
H10B H 0.9658 1.0658 0.6346 0.056 Uiso 1 1 calc GR . . . .
H10C H 0.8938 1.1958 0.6080 0.056 Uiso 1 1 calc GR . . . .
C11 C 0.88724(16) 0.4980(3) 0.43243(15) 0.0345(6) Uani 1 1 d . . . . .
H11 H 0.8788 0.4159 0.4693 0.041 Uiso 1 1 calc R . . . .
C12 C 0.93672(17) 0.5799(3) 0.30285(15) 0.0339(5) Uani 1 1 d . . . . .
H12A H 0.8930 0.5711 0.2536 0.051 Uiso 1 1 calc GR . . . .
H12B H 0.9945 0.5642 0.2873 0.051 Uiso 1 1 calc GR . . . .
H12C H 0.9335 0.6834 0.3272 0.051 Uiso 1 1 calc GR . . . .
C13 C 0.9411(2) 0.2972(3) 0.3451(2) 0.0471(7) Uani 1 1 d . . . . .
H13A H 1.0036 0.2873 0.3442 0.071 Uiso 1 1 calc GR . . . .
H13B H 0.9096 0.2684 0.2910 0.071 Uiso 1 1 calc GR . . . .
H13C H 0.9238 0.2283 0.3876 0.071 Uiso 1 1 calc GR . . . .
C14 C 0.70103(16) 0.3351(3) 0.54919(16) 0.0349(6) Uani 1 1 d . . . . .
H14 H 0.7189 0.3435 0.6071 0.042 Uiso 1 1 calc R . . . .
C15 C 0.6232(3) 0.1909(4) 0.4325(2) 0.0685(10) Uani 1 1 d . . . . .
H15A H 0.5605 0.2089 0.4228 0.103 Uiso 1 1 calc GR . . . .
H15B H 0.6357 0.0857 0.4145 0.103 Uiso 1 1 calc GR . . . .
H15C H 0.6522 0.2668 0.4011 0.103 Uiso 1 1 calc GR . . . .
C16 C 0.6323(2) 0.0858(4) 0.5784(2) 0.0627(9) Uani 1 1 d . . . . .
H16A H 0.6608 0.1074 0.6347 0.094 Uiso 1 1 calc GR . . . .
H16B H 0.6515 -0.0154 0.5604 0.094 Uiso 1 1 calc GR . . . .
H16C H 0.5693 0.0844 0.5775 0.094 Uiso 1 1 calc GR . . . .
Mn1 Mn 0.77504(2) 0.66957(4) 0.54249(2) 0.02009(11) Uani 0.22(3) 1 d . . P A 2


_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
Cu1 O1 2.0042(14) . ?
Cu1 O4 1.9660(14) . ?
Cu1 O5 1.9066(15) . ?
Cu1 N1 1.9034(17) . ?
Co1 O2 2.1456(15) 4_576 ?
Co1 O3 2.1391(14) 4_576 ?
Co1 O4 2.0894(15) . ?
Co1 O6 2.1021(16) . ?
Co1 O7 2.1596(15) . ?
Co1 O8 2.1279(17) . ?
O1 C1 1.264(2) . ?
O2 Co1 2.1457(15) 4_575 ?
O2 C1 1.247(2) . ?
O2 Mn1 2.1457(15) 4_575 ?
O3 Co1 2.1391(14) 4_575 ?
O3 C2 1.253(2) . ?
O3 Mn1 2.1391(14) 4_575 ?
O4 C8 1.358(3) . ?
O4 Mn1 2.0894(15) . ?
O5 C9 1.270(3) . ?
O6 C9 1.246(3) . ?
O6 Mn1 2.1021(16) . ?
O7 C11 1.243(3) . ?
O7 Mn1 2.1596(15) . ?
O8 C14 1.227(3) . ?
O8 Mn1 2.1279(17) . ?
N1 C2 1.313(3) . ?
N1 C3 1.404(3) . ?
N2 C11 1.306(3) . ?
N2 C12 1.455(3) . ?
N2 C13 1.452(3) . ?
N3 C14 1.317(3) . ?
N3 C15 1.451(4) . ?
N3 C16 1.448(4) . ?
C1 C2 1.540(3) . ?
C3 C4 1.391(3) . ?
C3 C8 1.411(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.382(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.392(3) . ?
C9 C10 1.505(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
Mn1 O2 2.1456(15) 4_576 ?
Mn1 O3 2.1391(14) 4_576 ?

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
O4 Cu1 O1 167.48(6) . . ?
O5 Cu1 O1 91.08(6) . . ?
O5 Cu1 O4 101.22(6) . . ?
N1 Cu1 O1 83.41(6) . . ?
N1 Cu1 O4 84.08(6) . . ?
N1 Cu1 O5 166.59(8) . . ?
O2 Co1 O7 98.86(6) 4_576 . ?
O3 Co1 O2 78.36(5) 4_576 4_576 ?
O3 Co1 O7 176.81(6) 4_576 . ?
O4 Co1 O2 175.99(5) . 4_576 ?
O4 Co1 O3 97.74(5) . 4_576 ?
O4 Co1 O6 90.62(6) . . ?
O4 Co1 O7 85.00(6) . . ?
O4 Co1 O8 94.07(6) . . ?
O6 Co1 O2 88.38(6) . 4_576 ?
O6 Co1 O3 89.42(6) . 4_576 ?
O6 Co1 O7 88.92(6) . . ?
O6 Co1 O8 173.16(7) . . ?
O8 Co1 O2 87.27(6) . 4_576 ?
O8 Co1 O3 94.87(6) . 4_576 ?
O8 Co1 O7 86.54(6) . . ?
C1 O1 Cu1 111.27(13) . . ?
C1 O2 Co1 112.70(13) . 4_575 ?
C1 O2 Mn1 112.70(13) . 4_575 ?
C2 O3 Co1 111.31(13) . 4_575 ?
C2 O3 Mn1 111.31(13) . 4_575 ?
Cu1 O4 Co1 104.41(6) . . ?
Cu1 O4 Mn1 104.41(6) . . ?
C8 O4 Cu1 110.80(11) . . ?
C8 O4 Co1 122.71(13) . . ?
C8 O4 Mn1 122.71(13) . . ?
C9 O5 Cu1 129.58(16) . . ?
C9 O6 Co1 132.03(14) . . ?
C9 O6 Mn1 132.03(14) . . ?
C11 O7 Co1 121.30(15) . . ?
C11 O7 Mn1 121.30(15) . . ?
C14 O8 Co1 128.41(16) . . ?
C14 O8 Mn1 128.41(16) . . ?
C2 N1 Cu1 116.57(14) . . ?
C2 N1 C3 128.98(18) . . ?
C3 N1 Cu1 114.44(13) . . ?
C11 N2 C12 121.3(2) . . ?
C11 N2 C13 121.9(2) . . ?
C13 N2 C12 116.78(19) . . ?
C14 N3 C15 119.7(3) . . ?
C14 N3 C16 122.4(3) . . ?
C16 N3 C15 117.8(3) . . ?
O1 C1 C2 117.70(17) . . ?
O2 C1 O1 125.52(19) . . ?
O2 C1 C2 116.77(18) . . ?
O3 C2 N1 130.16(19) . . ?
O3 C2 C1 118.86(17) . . ?
N1 C2 C1 110.98(17) . . ?
N1 C3 C8 112.19(18) . . ?
C4 C3 N1 127.29(19) . . ?
C4 C3 C8 120.52(19) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.1(2) . . ?
C8 C7 H7 119.9 . . ?
O4 C8 C3 118.49(18) . . ?
O4 C8 C7 122.70(19) . . ?
C7 C8 C3 118.8(2) . . ?
O5 C9 C10 115.5(2) . . ?
O6 C9 O5 125.6(2) . . ?
O6 C9 C10 118.89(19) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O7 C11 N2 126.0(2) . . ?
O7 C11 H11 117.0 . . ?
N2 C11 H11 117.0 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 C14 N3 125.4(2) . . ?
O8 C14 H14 117.3 . . ?
N3 C14 H14 117.3 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 Mn1 O7 98.86(6) 4_576 . ?
O3 Mn1 O2 78.36(5) 4_576 4_576 ?
O3 Mn1 O7 176.81(6) 4_576 . ?
O4 Mn1 O2 175.99(5) . 4_576 ?
O4 Mn1 O3 97.74(5) . 4_576 ?
O4 Mn1 O6 90.62(6) . . ?
O4 Mn1 O7 85.00(6) . . ?
O4 Mn1 O8 94.07(6) . . ?
O6 Mn1 O2 88.38(6) . 4_576 ?
O6 Mn1 O3 89.42(6) . 4_576 ?
O6 Mn1 O7 88.92(6) . . ?
O6 Mn1 O8 173.16(7) . . ?
O8 Mn1 O2 87.27(6) . 4_576 ?
O8 Mn1 O3 94.87(6) . 4_576 ?
O8 Mn1 O7 86.54(6) . . ?

_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_al_st233_c_0m
_database_code_depnum_ccdc_archive 'CCDC 2032125'
loop_
_audit_author_name
_audit_author_address
'Lise-Marie Chamoreau'
;Sorbonne Universite, CNRS, IPCM 
France
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;
_audit_creation_date             2019-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H21 Cu Mn N3 O8'
_chemical_formula_sum            'C16 H21 Cu Mn N3 O8'
_chemical_formula_weight         501.84
_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'
Cu Cu 0.3201 1.2651 '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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.1715(7)
_cell_length_b                   8.4796(4)
_cell_length_c                   16.1749(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.443(3)
_cell_angle_gamma                90
_cell_volume                     2058.32(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2722
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.70
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.694
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0552 before and 0.0459 after correction. The Ratio of minimum to maximum transmission is 0.8720. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17547
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.095
_diffrn_reflns_theta_min         1.357
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3797
_reflns_number_total             6040
_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 (Bruker)'
_computing_data_collection       'APEX2 (Bruker)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_molecular_graphics    'DIAMOND (Brandenburg)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         6040
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      0.969
_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)+(0.0425P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0971
_refine_special_details          ?
# start Validation Reply Form
_vrf_PLAT230_al_st233_c_0m       
;
PROBLEM: Hirshfeld Test Diff for    O8       --C14      .        7.5 s.u.  
RESPONSE: This alert concerns a C-O bond in a coordinated solvent molecule.
The ADPs of these atoms are low and in good agreement with the rest 
of the structure. No sign of alarm is detected. 
;
# end Validation Reply Form
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C14(H14)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Cu1 Cu 0.21716(2) 0.11405(4) 0.62042(2) 0.02467(10) Uani 1 1 d . . . . .
Mn1 Mn 0.22376(3) 0.33128(5) 0.45607(2) 0.02361(11) Uani 1 1 d . . . . .
O1 O 0.14546(13) 0.0409(2) 0.70689(10) 0.0282(4) Uani 1 1 d . . . . .
O2 O 0.15037(13) 0.0515(2) 0.84550(10) 0.0283(4) Uani 1 1 d . . . . .
O3 O 0.30915(13) 0.2056(2) 0.85951(10) 0.0268(4) Uani 1 1 d . . . . .
O4 O 0.30337(13) 0.2096(2) 0.55573(10) 0.0259(4) Uani 1 1 d . . . . .
O5 O 0.14833(14) -0.0142(2) 0.53827(10) 0.0336(5) Uani 1 1 d . . . . .
O6 O 0.15399(15) 0.1182(2) 0.42014(11) 0.0341(5) Uani 1 1 d . . . . .
O7 O 0.13160(15) 0.3716(2) 0.54750(12) 0.0359(5) Uani 1 1 d . . . . .
O8 O 0.27753(16) 0.5629(2) 0.49231(12) 0.0392(5) Uani 1 1 d . . . . .
N1 N 0.29354(15) 0.1967(3) 0.71423(12) 0.0230(5) Uani 1 1 d . . . . .
N2 N 0.08199(18) 0.5407(3) 0.63902(14) 0.0331(6) Uani 1 1 d . . . . .
N3 N 0.3457(2) 0.7966(3) 0.47608(19) 0.0495(7) Uani 1 1 d . . . . .
C1 C 0.18178(18) 0.0799(3) 0.77979(15) 0.0224(6) Uani 1 1 d . . . . .
C2 C 0.27069(18) 0.1697(3) 0.78806(14) 0.0216(5) Uani 1 1 d . . . . .
C3 C 0.36822(18) 0.2769(3) 0.69437(15) 0.0243(6) Uani 1 1 d . . . . .
C4 C 0.4357(2) 0.3480(3) 0.74907(17) 0.0334(7) Uani 1 1 d . . . . .
H4 H 0.4345 0.3440 0.8076 0.040 Uiso 1 1 calc R . . . .
C5 C 0.5045(2) 0.4246(4) 0.71832(19) 0.0401(8) Uani 1 1 d . . . . .
H5 H 0.5503 0.4745 0.7556 0.048 Uiso 1 1 calc R . . . .
C6 C 0.5064(2) 0.4283(4) 0.63317(19) 0.0387(7) Uani 1 1 d . . . . .
H6 H 0.5538 0.4813 0.6123 0.046 Uiso 1 1 calc R . . . .
C7 C 0.4411(2) 0.3566(3) 0.57823(18) 0.0337(7) Uani 1 1 d . . . . .
H7 H 0.4441 0.3590 0.5200 0.040 Uiso 1 1 calc R . . . .
C8 C 0.37051(18) 0.2805(3) 0.60723(15) 0.0248(6) Uani 1 1 d . . . . .
C9 C 0.1287(2) 0.0066(3) 0.46025(16) 0.0282(6) Uani 1 1 d . . . . .
C10 C 0.0690(2) -0.1169(4) 0.41420(17) 0.0373(7) Uani 1 1 d . . . . .
H10A H 0.1056 -0.1983 0.3929 0.056 Uiso 1 1 calc GR . . . .
H10B H 0.0304 -0.0676 0.3674 0.056 Uiso 1 1 calc GR . . . .
H10C H 0.0322 -0.1649 0.4524 0.056 Uiso 1 1 calc GR . . . .
C11 C 0.1122(2) 0.5059(4) 0.56979(18) 0.0395(8) Uani 1 1 d . . . . .
H11 H 0.1201 0.5906 0.5332 0.047 Uiso 1 1 calc R . . . .
C12 C 0.0655(2) 0.4210(4) 0.69885(18) 0.0374(7) Uani 1 1 d . . . . .
H12A H 0.0709 0.3163 0.6745 0.056 Uiso 1 1 calc GR . . . .
H12B H 0.0053 0.4343 0.7130 0.056 Uiso 1 1 calc GR . . . .
H12C H 0.1092 0.4315 0.7495 0.056 Uiso 1 1 calc GR . . . .
C13 C 0.0623(3) 0.7029(4) 0.6596(2) 0.0521(10) Uani 1 1 d . . . . .
H13A H 0.0803 0.7740 0.6173 0.078 Uiso 1 1 calc GR . . . .
H13B H 0.0952 0.7298 0.7146 0.078 Uiso 1 1 calc GR . . . .
H13C H -0.0018 0.7141 0.6609 0.078 Uiso 1 1 calc GR . . . .
C14 C 0.2987(2) 0.6707(4) 0.4494(2) 0.0445(8) Uani 1 1 d . . . . .
H14 H 0.2793 0.6635 0.3910 0.053 Uiso 1 1 calc R . . . .
C15 C 0.3798(3) 0.8102(5) 0.5645(3) 0.0769(14) Uani 1 1 d . . . . .
H15A H 0.3483 0.7359 0.5962 0.115 Uiso 1 1 calc GR . . . .
H15B H 0.3706 0.9180 0.5833 0.115 Uiso 1 1 calc GR . . . .
H15C H 0.4437 0.7858 0.5736 0.115 Uiso 1 1 calc GR . . . .
C16 C 0.3691(3) 0.9176(5) 0.4208(3) 0.0772(14) Uani 1 1 d . . . . .
H16A H 0.3396 0.8965 0.3639 0.116 Uiso 1 1 calc GR . . . .
H16B H 0.4339 0.9182 0.4217 0.116 Uiso 1 1 calc GR . . . .
H16C H 0.3499 1.0204 0.4393 0.116 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
Cu1 O1 1.9927(18) . ?
Cu1 O4 1.9656(18) . ?
Cu1 O5 1.9055(18) . ?
Cu1 N1 1.903(2) . ?
Mn1 O2 2.2002(18) 4_565 ?
Mn1 O3 2.1931(18) 4_565 ?
Mn1 O4 2.1333(18) . ?
Mn1 O6 2.131(2) . ?
Mn1 O7 2.206(2) . ?
Mn1 O8 2.174(2) . ?
O1 C1 1.270(3) . ?
O2 Mn1 2.2001(18) 4_566 ?
O2 C1 1.250(3) . ?
O3 Mn1 2.1932(18) 4_566 ?
O3 C2 1.253(3) . ?
O4 C8 1.358(3) . ?
O5 C9 1.266(3) . ?
O6 C9 1.240(3) . ?
O7 C11 1.242(3) . ?
O8 C14 1.219(4) . ?
N1 C2 1.312(3) . ?
N1 C3 1.398(3) . ?
N2 C11 1.305(4) . ?
N2 C12 1.449(4) . ?
N2 C13 1.456(4) . ?
N3 C14 1.321(4) . ?
N3 C15 1.452(5) . ?
N3 C16 1.439(5) . ?
C1 C2 1.537(4) . ?
C3 C4 1.388(4) . ?
C3 C8 1.415(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.372(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.389(4) . ?
C9 C10 1.508(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 0.9500 . ?
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 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Cu1 O1 167.52(7) . . ?
O5 Cu1 O1 90.69(8) . . ?
O5 Cu1 O4 101.73(8) . . ?
N1 Cu1 O1 83.47(8) . . ?
N1 Cu1 O4 84.13(8) . . ?
N1 Cu1 O5 166.80(9) . . ?
O2 Mn1 O7 100.37(7) 4_565 . ?
O3 Mn1 O2 76.52(7) 4_565 4_565 ?
O3 Mn1 O7 176.74(7) 4_565 . ?
O4 Mn1 O2 174.58(7) . 4_565 ?
O4 Mn1 O3 98.11(7) . 4_565 ?
O4 Mn1 O7 84.99(7) . . ?
O4 Mn1 O8 94.86(8) . . ?
O6 Mn1 O2 89.39(7) . 4_565 ?
O6 Mn1 O3 90.38(8) . 4_565 ?
O6 Mn1 O4 89.97(7) . . ?
O6 Mn1 O7 88.62(8) . . ?
O6 Mn1 O8 172.37(9) . . ?
O8 Mn1 O2 86.35(8) . 4_565 ?
O8 Mn1 O3 94.78(8) . 4_565 ?
O8 Mn1 O7 85.92(8) . . ?
C1 O1 Cu1 111.31(17) . . ?
C1 O2 Mn1 113.17(17) . 4_566 ?
C2 O3 Mn1 112.23(17) . 4_566 ?
Cu1 O4 Mn1 104.74(9) . . ?
C8 O4 Cu1 110.72(15) . . ?
C8 O4 Mn1 122.67(16) . . ?
C9 O5 Cu1 129.83(19) . . ?
C9 O6 Mn1 133.16(17) . . ?
C11 O7 Mn1 122.47(19) . . ?
C14 O8 Mn1 130.1(2) . . ?
C2 N1 Cu1 116.76(18) . . ?
C2 N1 C3 128.7(2) . . ?
C3 N1 Cu1 114.52(16) . . ?
C11 N2 C12 122.1(3) . . ?
C11 N2 C13 121.3(3) . . ?
C12 N2 C13 116.6(2) . . ?
C14 N3 C15 118.9(3) . . ?
C14 N3 C16 123.0(3) . . ?
C16 N3 C15 118.1(3) . . ?
O1 C1 C2 117.7(2) . . ?
O2 C1 O1 124.9(3) . . ?
O2 C1 C2 117.4(2) . . ?
O3 C2 N1 130.4(3) . . ?
O3 C2 C1 119.0(2) . . ?
N1 C2 C1 110.7(2) . . ?
N1 C3 C8 112.2(2) . . ?
C4 C3 N1 127.6(2) . . ?
C4 C3 C8 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.4(3) . . ?
C8 C7 H7 119.8 . . ?
O4 C8 C3 118.4(2) . . ?
O4 C8 C7 123.0(2) . . ?
C7 C8 C3 118.6(3) . . ?
O5 C9 C10 115.6(3) . . ?
O6 C9 O5 125.6(3) . . ?
O6 C9 C10 118.8(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O7 C11 N2 125.8(3) . . ?
O7 C11 H11 117.1 . . ?
N2 C11 H11 117.1 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 C14 N3 126.5(3) . . ?
O8 C14 H14 116.7 . . ?
N3 C14 H14 116.7 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
