# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2016

####################################################################### 
# 
# 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_hydrfe_rt_pna21
_database_code_depnum_ccdc_archive 'CCDC 1506139'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H8 Fe N2 O6'
_chemical_formula_weight         223.96

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'
Fe Fe 0.3463 0.8444 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.811(3)
_cell_length_b                   7.782(3)
_cell_length_c                   11.657(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     799.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    4791
_cell_measurement_theta_min      3.4680
_cell_measurement_theta_max      28.9750

_exptl_crystal_description       block
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.349
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.294
_exptl_absorpt_coefficient_mu    1.884
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.563
_exptl_absorpt_correction_T_max  0.639
_exptl_absorpt_process_details   
;
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            7617
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.147
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1573
_reflns_number_gt                1409
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0287P)²+0.0897P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0164(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 616 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.054(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1573
_refine_ls_number_parameters     111
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0200
_refine_ls_wR_factor_ref         0.0510
_refine_ls_wR_factor_gt          0.0494
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe -0.52617(4) -0.49974(6) -0.11111(11) 0.01869(15) Uani 1 1 d . . . . .
O1 O -0.3112(2) -0.4188(3) -0.1774(2) 0.0311(5) Uani 1 1 d . . . . .
O2 O -0.1244(2) -0.2292(3) -0.1785(2) 0.0299(5) Uani 1 1 d . . . . .
O3 O -0.4261(3) -0.7264(3) -0.04228(19) 0.0305(5) Uani 1 1 d . . . . .
O4 O -0.2384(2) -0.9159(3) -0.0405(2) 0.0292(5) Uani 1 1 d . . . . .
O5 O -0.5547(3) -0.6402(3) -0.26797(18) 0.0301(6) Uani 1 1 d . . . . .
O6 O -0.5155(3) -0.6360(3) -0.4555(2) 0.0336(6) Uani 1 1 d . . . . .
C1 C -0.2543(4) -0.2786(4) -0.1510(3) 0.0312(8) Uani 1 1 d . . . . .
H1 H -0.3130 -0.2042 -0.1072 0.037 Uiso 1 1 calc R U . . .
C2 C -0.3080(4) -0.7900(4) -0.0808(3) 0.0310(8) Uani 1 1 d . . . . .
H2 H -0.2672 -0.7392 -0.1461 0.037 Uiso 1 1 calc R U . . .
C3 C -0.5315(4) -0.5645(4) -0.3617(4) 0.0286(8) Uani 1 1 d . . . . .
H3 H -0.5260 -0.4452 -0.3603 0.034 Uiso 1 1 calc R U . . .
N1 N -0.0688(6) -0.5065(3) -0.3444(4) 0.0363(11) Uani 1 1 d . . . . .
H1A H -0.1345 -0.5132 -0.4023 0.044 Uiso 1 1 calc R U . . .
H1B H -0.0905 -0.4153 -0.3015 0.044 Uiso 1 1 calc R U . . .
H1C H -0.0752 -0.6012 -0.3019 0.044 Uiso 1 1 calc R U . . .
N2 N 0.0816(7) -0.4905(4) -0.3888(5) 0.0557(16) Uani 1 1 d . . . . .
H2A H 0.1028 -0.5798 -0.4296 0.067 Uiso 1 1 d R U . . .
H2B H 0.0881 -0.3998 -0.4311 0.067 Uiso 1 1 d R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O3 2.129(2) . ?
Fe1 O2 2.131(2) 4_445 ?
Fe1 O6 2.131(3) 2_445 ?
Fe1 O1 2.140(2) . ?
Fe1 O5 2.145(3) . ?
Fe1 O4 2.146(2) 4_435 ?
O1 C1 1.240(4) . ?
O2 C1 1.249(4) . ?
O2 Fe1 2.131(2) 4_545 ?
O3 C2 1.236(4) . ?
O4 C2 1.248(4) . ?
O4 Fe1 2.146(2) 4_535 ?
O5 C3 1.258(5) . ?
O6 C3 1.235(5) . ?
O6 Fe1 2.131(3) 2_444 ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
N1 N2 1.428(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 H2A 0.8623 . ?
N2 H2B 0.8625 . ?

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
O3 Fe1 O2 179.21(11) . 4_445 ?
O3 Fe1 O6 91.07(11) . 2_445 ?
O2 Fe1 O6 88.23(10) 4_445 2_445 ?
O3 Fe1 O1 90.77(9) . . ?
O2 Fe1 O1 88.87(9) 4_445 . ?
O6 Fe1 O1 90.51(9) 2_445 . ?
O3 Fe1 O5 87.00(10) . . ?
O2 Fe1 O5 93.68(11) 4_445 . ?
O6 Fe1 O5 176.75(11) 2_445 . ?
O1 Fe1 O5 86.91(10) . . ?
O3 Fe1 O4 87.87(9) . 4_435 ?
O2 Fe1 O4 92.48(9) 4_445 4_435 ?
O6 Fe1 O4 88.58(10) 2_445 4_435 ?
O1 Fe1 O4 178.34(12) . 4_435 ?
O5 Fe1 O4 93.96(10) . 4_435 ?
C1 O1 Fe1 121.9(2) . . ?
C1 O2 Fe1 122.4(2) . 4_545 ?
C2 O3 Fe1 122.9(2) . . ?
C2 O4 Fe1 121.6(2) . 4_535 ?
C3 O5 Fe1 118.9(2) . . ?
C3 O6 Fe1 123.4(2) . 2_444 ?
O1 C1 O2 125.3(3) . . ?
O1 C1 H1 117.3 . . ?
O2 C1 H1 117.3 . . ?
O3 C2 O4 126.2(3) . . ?
O3 C2 H2 116.9 . . ?
O4 C2 H2 116.9 . . ?
O6 C3 O5 125.2(3) . . ?
O6 C3 H3 117.4 . . ?
O5 C3 H3 117.4 . . ?
N2 N1 H1A 109.5 . . ?
N2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
N2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N1 N2 H2A 109.3 . . ?
N1 N2 H2B 109.9 . . ?
H2A N2 H2B 109.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 O1 C1 O2 173.7(3) . . . . ?
Fe1 O2 C1 O1 -171.9(3) 4_545 . . . ?
Fe1 O3 C2 O4 175.3(3) . . . . ?
Fe1 O4 C2 O3 -175.8(3) 4_535 . . . ?
Fe1 O6 C3 O5 -179.3(3) 2_444 . . . ?
Fe1 O5 C3 O6 165.4(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
N1 H1B O1 0.89 2.42 2.970(6) 119.9 .
N1 H1B O2 0.89 2.06 2.940(5) 169.8 .
N1 H1A O4 0.89 2.10 2.933(6) 154.9 3_454
N1 H1C O5 0.89 2.06 2.893(4) 155.6 4_535
N2 H2B O3 0.86 2.35 3.049(5) 138.0 3_454
N2 H2A O6 0.86 2.46 3.128(5) 134.4 4_535

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_hydrfe_360k
_database_code_depnum_ccdc_archive 'CCDC 1506140'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H8 Fe N2 O6'
_chemical_formula_weight         223.96

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'
Fe Fe 0.3463 0.8444 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   8.736(3)
_cell_length_b                   11.763(4)
_cell_length_c                   7.871(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     808.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    360(2)
_cell_measurement_reflns_used    2161
_cell_measurement_theta_min      3.4690
_cell_measurement_theta_max      28.8540

_exptl_crystal_description       block
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.154
_exptl_absorpt_coefficient_mu    1.861
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_T_max  0.813
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.34a (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      360(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            4861
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.114
_diffrn_reflns_theta_max         25.990
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             842
_reflns_number_gt                655
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+0.1378P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         842
_refine_ls_number_parameters     74
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0788
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.5000 0.0000 0.5000 0.02852(19) Uani 1 2 d S . P . .
O1 O 0.46464(18) 0.15617(13) 0.36613(19) 0.0445(4) Uani 1 1 d . . . . .
O2 O 0.40243(18) 0.06791(12) 0.72685(17) 0.0430(4) Uani 1 1 d . . . . .
O3 O 0.21747(17) 0.06654(13) 0.91839(17) 0.0427(4) Uani 1 1 d . . . . .
C1 C 0.4724(4) 0.2500 0.4378(4) 0.0383(7) Uani 1 2 d S T P . .
H1 H 0.4851 0.2500 0.5551 0.046 Uiso 1 2 calc R U P . .
C2 C 0.2804(3) 0.0324(2) 0.7858(3) 0.0469(6) Uani 1 1 d . . . . .
H2 H 0.2311 -0.0251 0.7258 0.056 Uiso 1 1 calc R U . . .
N1 N 0.4310(6) 0.2500 1.0119(4) 0.0596(10) Uani 1 2 d DS T P . .
N2 N 0.5801(7) 0.2835(7) 0.9823(7) 0.089(3) Uani 0.5 1 d D . P . .
H1B H 0.382(4) 0.190(2) 0.970(4) 0.107 Uiso 1 1 d D U . . .
H1A H 0.407(6) 0.2500 1.120(3) 0.107 Uiso 1 2 d DS U P . .
H2B H 0.574(9) 0.306(5) 0.876(4) 0.107 Uiso 0.5 1 d D U P . .
H2A H 0.635(5) 0.2500 1.056(5) 0.107 Uiso 1 2 d DS U 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
Fe1 O2 2.1337(15) . ?
Fe1 O2 2.1337(15) 5_656 ?
Fe1 O1 2.1402(16) . ?
Fe1 O1 2.1402(16) 5_656 ?
Fe1 O3 2.1528(15) 6_657 ?
Fe1 O3 2.1528(15) 2_554 ?
O1 C1 1.241(2) . ?
O2 C2 1.235(3) . ?
O3 C2 1.246(3) . ?
O3 Fe1 2.1528(15) 2 ?
C1 O1 1.241(2) 8_565 ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
N1 N2 1.380(9) . ?
N1 N2 1.380(9) 8_565 ?
N1 H1B 0.886(19) . ?
N1 H1A 0.878(19) . ?
N2 N2 0.788(16) 8_565 ?
N2 H2B 0.88(2) . ?
N2 H2A 0.852(19) . ?

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 Fe1 O2 180.0 . 5_656 ?
O2 Fe1 O1 91.89(6) . . ?
O2 Fe1 O1 88.11(6) 5_656 . ?
O2 Fe1 O1 88.11(6) . 5_656 ?
O2 Fe1 O1 91.89(6) 5_656 5_656 ?
O1 Fe1 O1 180.0 . 5_656 ?
O2 Fe1 O3 88.09(6) . 6_657 ?
O2 Fe1 O3 91.91(6) 5_656 6_657 ?
O1 Fe1 O3 87.83(6) . 6_657 ?
O1 Fe1 O3 92.17(6) 5_656 6_657 ?
O2 Fe1 O3 91.91(6) . 2_554 ?
O2 Fe1 O3 88.09(6) 5_656 2_554 ?
O1 Fe1 O3 92.17(6) . 2_554 ?
O1 Fe1 O3 87.83(6) 5_656 2_554 ?
O3 Fe1 O3 180.0 6_657 2_554 ?
C1 O1 Fe1 122.13(17) . . ?
C2 O2 Fe1 122.17(14) . . ?
C2 O3 Fe1 121.47(15) . 2 ?
O1 C1 O1 125.6(3) 8_565 . ?
O1 C1 H1 117.2 8_565 . ?
O1 C1 H1 117.2 . . ?
O2 C2 O3 125.9(2) . . ?
O2 C2 H2 117.1 . . ?
O3 C2 H2 117.1 . . ?
N2 N1 N2 33.2(7) . 8_565 ?
N2 N1 H1B 128(3) . . ?
N2 N1 H1B 100(3) 8_565 . ?
N2 N1 H1A 113(4) . . ?
N2 N1 H1A 113(4) 8_565 . ?
H1B N1 H1A 104(3) . . ?
N2 N2 N1 73.4(3) 8_565 . ?
N2 N2 H2B 108(4) 8_565 . ?
N1 N2 H2B 101(5) . . ?
N2 N2 H2A 62.4(9) 8_565 . ?
N1 N2 H2A 107(4) . . ?
H2B N2 H2A 145(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 O1 C1 O1 174.3(2) . . . 8_565 ?
Fe1 O2 C2 O3 178.98(18) . . . . ?
Fe1 O3 C2 O2 177.76(19) 2 . . . ?

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
N1 H1A O1 0.878(19) 2.29(3) 3.013(3) 140(3) 1_556
N1 H1A O1 0.878(19) 2.29(3) 3.013(3) 140(3) 8_566
N1 H1B O3 0.886(19) 2.09(2) 2.946(3) 163(4) .
N1 H1B O2 0.886(19) 2.40(3) 3.112(3) 137(3) .
N2 H2B O2 0.88(2) 2.42(6) 3.083(6) 133(6) 8_565

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_hydrfe_p63_360k
_database_code_depnum_ccdc_archive 'CCDC 1506141'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H8 Fe N2 O6'
_chemical_formula_weight         223.96

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'
Fe Fe 0.3463 0.8444 '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'

_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_H-M_alt        'P 63'
_space_group_name_Hall           'P 6c'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/2'
'-y, x-y, z'
'-x, -y, z+1/2'
'-x+y, -x, z'
'y, -x+y, z+1/2'

_cell_length_a                   7.946(3)
_cell_length_b                   7.946(3)
_cell_length_c                   7.618(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     416.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    360(2)
_cell_measurement_reflns_used    1818
_cell_measurement_theta_min      2.9460
_cell_measurement_theta_max      24.7960

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_F_000             228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.349
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.168
_exptl_absorpt_coefficient_mu    1.807
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_T_max  0.796
_exptl_absorpt_process_details   
;
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      360(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            3723
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.960
_diffrn_reflns_theta_max         29.402
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             711
_reflns_number_gt                617
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_max     0.880
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²+0.0177P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 256 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.030(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         711
_refine_ls_number_parameters     50
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0628
_refine_ls_wR_factor_gt          0.0595
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe -0.3333 -0.6667 -0.2682(4) 0.0262(2) Uani 1 3 d S T P . .
O1 O -0.3154(4) -0.4357(4) -0.4224(3) 0.0502(8) Uani 1 1 d . . . . .
O2 O -0.4356(4) -0.3158(4) -0.6145(3) 0.0502(8) Uani 1 1 d . . . . .
C1 C -0.4443(6) -0.4439(5) -0.5182(9) 0.0436(9) Uani 1 1 d . . . . .
H1 H -0.5617 -0.5605 -0.5174 0.052 Uiso 1 1 calc R U . . .
N1 N -0.076(6) -0.026(8) -0.336(4) 0.121(14) Uani 0.3333 1 d D U P . .
H1A H -0.1854 -0.1313 -0.3505 0.145 Uiso 0.3333 1 d R U P . .
H1B H -0.0957 0.0628 -0.2912 0.145 Uiso 0.3333 1 d R U P . .
N2 N 0.047(4) -0.028(5) -0.214(3) 0.098(11) Uani 0.3333 1 d D U P . .
H2A H 0.1401 -0.0401 -0.2669 0.117 Uiso 0.3333 1 calc R U P . .
H2B H -0.0183 -0.1278 -0.1410 0.117 Uiso 0.3333 1 calc R U P . .
H2C H 0.1002 0.0824 -0.1528 0.117 Uiso 0.3333 1 calc R U 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
Fe1 O2 2.122(3) 6_545 ?
Fe1 O2 2.122(3) 2 ?
Fe1 O2 2.122(3) 4_445 ?
Fe1 O1 2.123(3) 5_545 ?
Fe1 O1 2.123(3) 3_445 ?
Fe1 O1 2.123(3) . ?
O1 C1 1.232(6) . ?
O2 C1 1.228(6) . ?
O2 Fe1 2.122(3) 2_454 ?
C1 H1 0.9300 . ?
N1 N2 0.946(15) 5 ?
N1 N2 1.24(4) 3 ?
N1 N2 1.358(12) . ?
N1 H1A 0.8599 . ?
N1 H1B 0.8610 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?

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 Fe1 O2 92.51(14) 6_545 2 ?
O2 Fe1 O2 92.51(14) 6_545 4_445 ?
O2 Fe1 O2 92.51(14) 2 4_445 ?
O2 Fe1 O1 83.02(9) 6_545 5_545 ?
O2 Fe1 O1 92.52(10) 2 5_545 ?
O2 Fe1 O1 173.41(9) 4_445 5_545 ?
O2 Fe1 O1 92.52(10) 6_545 3_445 ?
O2 Fe1 O1 173.41(9) 2 3_445 ?
O2 Fe1 O1 83.02(9) 4_445 3_445 ?
O1 Fe1 O1 92.32(14) 5_545 3_445 ?
O2 Fe1 O1 173.41(9) 6_545 . ?
O2 Fe1 O1 83.02(9) 2 . ?
O2 Fe1 O1 92.52(10) 4_445 . ?
O1 Fe1 O1 92.32(14) 5_545 . ?
O1 Fe1 O1 92.32(14) 3_445 . ?
C1 O1 Fe1 126.0(3) . . ?
C1 O2 Fe1 125.9(3) . 2_454 ?
O2 C1 O1 127.5(4) . . ?
O2 C1 H1 116.2 . . ?
O1 C1 H1 116.2 . . ?
N2 N1 N2 47(4) 5 3 ?
N2 N1 N2 42(4) 5 . ?
N2 N1 N2 40(3) 3 . ?
N2 N1 H1A 92.9 5 . ?
N2 N1 H1A 138.8 3 . ?
N2 N1 H1A 117.4 . . ?
N2 N1 H1B 77.4 5 . ?
N2 N1 H1B 60.7 3 . ?
N2 N1 H1B 99.6 . . ?
H1A N1 H1B 110.1 . . ?
N1 N2 H2A 109.5 . . ?
N1 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
N1 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 O2 C1 O1 -177.0(4) 2_454 . . . ?
Fe1 O1 C1 O2 -176.6(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
N1 H1A O1 0.86 2.17 2.91(6) 143.6 .
N1 H1B O1 0.86 2.34 2.98(5) 131.3 5
N1 H1B O2 0.86 2.42 3.16(5) 144.3 6
N2 H2A O1 0.89 2.36 3.13(3) 145.9 3
N2 H2B O2 0.89 2.17 2.92(4) 141.7 2
N2 H2C O2 0.89 2.38 3.02(3) 128.7 4
N2 H2B N1 0.89 2.40 2.96(3) 121.0 2

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_hydrmn_p63_310k
_database_code_depnum_ccdc_archive 'CCDC 1506142'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H8 Mn N2 O6'
_chemical_formula_weight         223.05

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'
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'

_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_H-M_alt        'P 63'
_space_group_name_Hall           'P 6c'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/2'
'-y, x-y, z'
'-x, -y, z+1/2'
'-x+y, -x, z'
'y, -x+y, z+1/2'

_cell_length_a                   7.988(3)
_cell_length_b                   7.988(3)
_cell_length_c                   7.807(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     431.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    310(2)
_cell_measurement_reflns_used    5005
_cell_measurement_theta_min      2.9220
_cell_measurement_theta_max      27.5860

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             226
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.135
_exptl_absorpt_coefficient_mu    1.527
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_process_details   
;
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      310(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            8258
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.936
_diffrn_reflns_theta_max         25.957
_diffrn_reflns_theta_full        25.957
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             567
_reflns_number_gt                544
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0222P)²+0.0711P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 244 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         567
_refine_ls_number_parameters     50
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0171
_refine_ls_wR_factor_ref         0.0419
_refine_ls_wR_factor_gt          0.0415
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn -0.3333 -0.6667 -0.27200(19) 0.02482(18) Uani 1 3 d S T P . .
O1 O -0.3130(3) -0.4305(3) -0.4260(3) 0.0491(6) Uani 1 1 d . . . . .
O2 O -0.4303(3) -0.3131(3) -0.6181(3) 0.0489(6) Uani 1 1 d . . . . .
C1 C -0.4401(4) -0.4397(4) -0.5222(6) 0.0451(7) Uani 1 1 d . . . . .
H1 H -0.5567 -0.5560 -0.5221 0.054 Uiso 1 1 calc R U . . .
N1 N -0.065(6) -0.024(9) -0.343(4) 0.120(13) Uani 0.3333 1 d D . P . .
H1A H -0.1650 -0.1322 -0.3705 0.144 Uiso 0.3333 1 d R U P . .
H1B H -0.1010 0.0535 -0.3035 0.144 Uiso 0.3333 1 d R U P . .
N2 N 0.042(4) -0.030(8) -0.214(3) 0.131(15) Uani 0.3333 1 d D . P . .
H2A H 0.1485 -0.0245 -0.2554 0.157 Uiso 0.3333 1 calc R U P . .
H2B H -0.0257 -0.1399 -0.1555 0.157 Uiso 0.3333 1 calc R U P . .
H2C H 0.0748 0.0697 -0.1440 0.157 Uiso 0.3333 1 calc R U 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 O1 2.174(2) 5_545 ?
Mn1 O1 2.174(2) 3_445 ?
Mn1 O1 2.174(2) . ?
Mn1 O2 2.174(2) 6_545 ?
Mn1 O2 2.174(2) 4_445 ?
Mn1 O2 2.174(2) 2 ?
O1 C1 1.235(4) . ?
O2 C1 1.230(4) . ?
O2 Mn1 2.174(2) 2_454 ?
C1 H1 0.9300 . ?
N1 N2 1.015(17) 5 ?
N1 N2 1.27(5) 3 ?
N1 N2 1.338(18) . ?
N1 H1A 0.8599 . ?
N1 H1B 0.8605 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 O1 92.35(10) 5_545 3_445 ?
O1 Mn1 O1 92.35(10) 5_545 . ?
O1 Mn1 O1 92.35(10) 3_445 . ?
O1 Mn1 O2 82.51(7) 5_545 6_545 ?
O1 Mn1 O2 93.18(8) 3_445 6_545 ?
O1 Mn1 O2 172.60(7) . 6_545 ?
O1 Mn1 O2 172.60(7) 5_545 4_445 ?
O1 Mn1 O2 82.52(7) 3_445 4_445 ?
O1 Mn1 O2 93.18(8) . 4_445 ?
O2 Mn1 O2 92.42(10) 6_545 4_445 ?
O1 Mn1 O2 93.18(8) 5_545 2 ?
O1 Mn1 O2 172.60(7) 3_445 2 ?
O1 Mn1 O2 82.52(7) . 2 ?
O2 Mn1 O2 92.42(10) 6_545 2 ?
O2 Mn1 O2 92.42(10) 4_445 2 ?
C1 O1 Mn1 125.6(2) . . ?
C1 O2 Mn1 125.4(2) . 2_454 ?
O2 C1 O1 127.5(3) . . ?
O2 C1 H1 116.2 . . ?
O1 C1 H1 116.2 . . ?
N2 N1 N2 43(4) 5 3 ?
N2 N1 N2 41(4) 5 . ?
N2 N1 N2 39(3) 3 . ?
N2 N1 H1A 98.7 5 . ?
N2 N1 H1A 141.9 3 . ?
N2 N1 H1A 116.4 . . ?
N2 N1 H1B 74.5 5 . ?
N2 N1 H1B 66.0 3 . ?
N2 N1 H1B 102.1 . . ?
H1A N1 H1B 109.6 . . ?
N1 N2 H2A 109.5 . . ?
N1 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
N1 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 O2 C1 O1 -175.8(3) 2_454 . . . ?
Mn1 O1 C1 O2 -175.7(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
N1 H1A O1 0.86 2.11 2.91(6) 154.1 .
N1 H1B O1 0.86 2.35 3.00(6) 132.9 5
N1 H1B O2 0.86 2.47 3.24(4) 150.3 6
N2 H2A O1 0.89 2.36 3.18(3) 152.7 3
N2 H2B O2 0.89 2.07 2.88(5) 150.8 2
N2 H2C N1 0.89 2.46 3.049(17) 124.3 6

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1506143'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;
_publcif_datablock.id            {2e42d879-90b7-44d5-a162-a7a61bfa7a8e}

#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H19 Br N7 O3 Zn, C H4 O, Br'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C13 H23 Br2 N7 O4 Zn1'
_chemical_formula_weight         566.6
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ycb'
_symmetry_Int_Tables_number      14

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2

_cell_length_a                   11.1965(4)
_cell_length_b                   13.5143(5)
_cell_length_c                   12.9627(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.488(3)
_cell_angle_gamma                90
_cell_volume                     1952.43(13)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            4

_cell_measurement_reflns_used    5888
_cell_measurement_theta_min      3.55
_cell_measurement_theta_max      28.92
_cell_measurement_temperature    120
_cell_special_details            ?

_exptl_crystal_density_diffrn    1.9268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1128

_exptl_absorpt_coefficient_mu    5.387
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.113
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            colourless
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
   CrysAlisPro, Agilent Technologies, Version 1.171.37.33a	
   Analytical numeric absorption correction based on crystal shape
;
_exptl_absorpt_correction_T_min  0.408
_exptl_absorpt_correction_T_max  0.617
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      120
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1892
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            12408
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         29.45
_diffrn_reflns_theta_full        27.31
_diffrn_measured_fraction_theta_max 0.86
_diffrn_measured_fraction_theta_full 0.98
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          x-ray

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          ?

_reflns_number_total             4681
_reflns_number_gt                3949
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_gt          0.0712
_refine_ls_R_factor_all          0.0394
_refine_ls_wR_factor_ref         0.0737
_refine_ls_goodness_of_fit_ref   1.65
_refine_ls_goodness_of_fit_gt    1.75
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         4681
_refine_ls_number_parameters     268
_refine_ls_number_restraints     8
_refine_ls_number_constraints    68
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0004I²)
_refine_ls_hydrogen_treatment    mixed
_refine_ls_shift/su_max          0.0227
_refine_ls_shift/su_mean         0.0015
_refine_diff_density_max         0.68
_refine_diff_density_min         -0.74
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
Br -0.2901 2.4595 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0106 0.0060 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
Zn 0.2839 1.4301 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
;
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_restr_distance_atom_site_label_1
_restr_distance_site_symmetry_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
N24 . H1n24 . 0.88 0.001
N27 . H1n27 . 0.88 0.001
N27 . H2n27 . 0.88 0.001
N64 . H1n64 . 0.88 0.001
N67 . H1n67 . 0.88 0.001
N67 . H2n67 . 0.88 0.001
O1m . H1o1m . 0.84 0.001
O3m . H1o3m . 0.84 0.001

loop_
_restr_angle_atom_site_label_1
_restr_angle_site_symmetry_1
_restr_angle_atom_site_label_2
_restr_angle_site_symmetry_2
_restr_angle_atom_site_label_3
_restr_angle_site_symmetry_3
_restr_angle_target
_restr_angle_target_weight_param
? ? ? ? ? ? ? ?

loop_
_restr_torsion_atom_site_label_1
_restr_torsion_site_symmetry_1
_restr_torsion_atom_site_label_2
_restr_torsion_site_symmetry_2
_restr_torsion_atom_site_label_3
_restr_torsion_site_symmetry_3
_restr_torsion_atom_site_label_4
_restr_torsion_site_symmetry_4
_restr_torsion_angle_target
_restr_torsion_weight_param
? ? ? ? ? ? ? ? ? ?

loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_site_symmetry_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
? ? ? ? ? ?

loop_
_restr_equal_angle_atom_site_label_1
_restr_equal_angle_site_symmetry_1
_restr_equal_angle_atom_site_label_2
_restr_equal_angle_site_symmetry_2
_restr_equal_angle_atom_site_label_3
_restr_equal_angle_site_symmetry_3
_restr_equal_angle_class_class_id
_restr_equal_angle_class_target_weight_param
? ? ? ? ? ? ? ?

loop_
_restr_equal_torsion_atom_site_label_1
_restr_equal_torsion_site_symmetry_1
_restr_equal_torsion_atom_site_label_2
_restr_equal_torsion_site_symmetry_2
_restr_equal_torsion_atom_site_label_3
_restr_equal_torsion_site_symmetry_3
_restr_equal_torsion_atom_site_label_4
_restr_equal_torsion_site_symmetry_4
_restr_equal_torsion_class_class_id
_restr_equal_torsion_class_target_weight_param
? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.47448(3) 0.36846(2) 0.34875(2) Uani 0.01838(9) 4 1 d . . .
Br2 Br 0.06160(3) 0.29509(2) 0.24512(3) Uani 0.02263(10) 4 1 d . . .
Zn1 Zn 0.66491(3) 0.40372(2) 0.25484(2) Uani 0.01153(9) 4 1 d . . .
N1 N 0.77114(19) 0.43339(16) 0.40374(17) Uani 0.0123(7) 4 1 d . . .
C2 C 0.8314(2) 0.3588(2) 0.4529(2) Uani 0.0140(8) 4 1 d . . .
C3 C 0.8990(2) 0.3731(2) 0.5474(2) Uani 0.0182(9) 4 1 d . . .
C4 C 0.9013(2) 0.4671(2) 0.5905(2) Uani 0.0205(9) 4 1 d . . .
C5 C 0.8381(2) 0.5436(2) 0.5403(2) Uani 0.0180(9) 4 1 d . . .
C6 C 0.7738(2) 0.5240(2) 0.4456(2) Uani 0.0137(8) 4 1 d . . .
C21 C 0.8181(2) 0.2620(2) 0.3993(2) Uani 0.0155(8) 4 1 d . . .
C22 C 0.8829(3) 0.1732(2) 0.4449(3) Uani 0.0276(10) 4 1 d . . .
N23 N 0.74694(19) 0.26432(16) 0.31543(18) Uani 0.0122(7) 4 1 d . . .
N24 N 0.7208(2) 0.18225(16) 0.25705(19) Uani 0.0147(7) 4 1 d . . .
C25 C 0.6471(2) 0.19855(19) 0.1673(2) Uani 0.0128(8) 4 1 d . . .
O26 O 0.61634(17) 0.28321(13) 0.14028(15) Uani 0.0147(6) 4 1 d . . .
N27 N 0.6126(2) 0.11721(17) 0.1138(2) Uani 0.0157(7) 4 1 d . . .
C61 C 0.7055(2) 0.59955(19) 0.3812(2) Uani 0.0125(8) 4 1 d . . .
C62 C 0.6975(3) 0.70444(19) 0.4159(2) Uani 0.0176(9) 4 1 d . . .
N63 N 0.6592(2) 0.56563(16) 0.29451(18) Uani 0.0126(7) 4 1 d . . .
N64 N 0.5967(2) 0.62373(16) 0.22236(18) Uani 0.0138(7) 4 1 d . . .
C65 C 0.5564(2) 0.5758(2) 0.1328(2) Uani 0.0152(8) 4 1 d . . .
O66 O 0.57291(18) 0.48472(13) 0.12474(15) Uani 0.0167(6) 4 1 d . . .
N67 N 0.5001(3) 0.63047(17) 0.0584(2) Uani 0.0205(8) 4 1 d . . .
O1m O 0.82567(18) 0.42468(14) 0.18000(16) Uani 0.0185(6) 4 1 d . . .
C2m C 0.8733(3) 0.5170(2) 0.1523(3) Uani 0.0285(11) 4 1 d . . .
O3m O 0.2291(3) 0.48526(16) 0.1989(2) Uani 0.0387(9) 4 1 d . . .
C4m C 0.2778(4) 0.4550(3) 0.1141(4) Uani 0.0503(16) 4 1 d . . .
H1c3 H 0.942742 0.319481 0.581838 Uiso 0.0218 4 1 d . . .
H1c4 H 0.947167 0.479123 0.655703 Uiso 0.0245 4 1 d . . .
H1c5 H 0.83865 0.608611 0.570031 Uiso 0.0215 4 1 d . . .
H1c22 H 0.96027 0.192695 0.476856 Uiso 0.0331 4 1 d . . .
H2c22 H 0.837299 0.14394 0.496084 Uiso 0.0331 4 1 d . . .
H3c22 H 0.892884 0.125874 0.39119 Uiso 0.0331 4 1 d . . .
H1c62 H 0.707282 0.707099 0.490208 Uiso 0.0211 4 1 d . . .
H2c62 H 0.759616 0.742625 0.388563 Uiso 0.0211 4 1 d . . .
H3c62 H 0.620613 0.731076 0.391135 Uiso 0.0211 4 1 d . . .
H1c2m H 0.943078 0.506123 0.116132 Uiso 0.0342 4 1 d . . .
H2c2m H 0.814074 0.552281 0.10823 Uiso 0.0342 4 1 d . . .
H3c2m H 0.895055 0.555023 0.213762 Uiso 0.0342 4 1 d . . .
H1c4m H 0.218594 0.420535 0.069278 Uiso 0.0603 4 1 d . . .
H2c4m H 0.306124 0.511321 0.078444 Uiso 0.0603 4 1 d . . .
H3c4m H 0.343833 0.411458 0.133859 Uiso 0.0603 4 1 d . . .
H1n67 H 0.490(3) 0.6949(4) 0.062(3) Uiso 0.0246 4 1 d . . .
H1n27 H 0.631(3) 0.0579(9) 0.138(2) Uiso 0.0189 4 1 d . . .
H2n27 H 0.570(2) 0.125(2) 0.0535(12) Uiso 0.0189 4 1 d . . .
H1n64 H 0.592(3) 0.6882(4) 0.230(2) Uiso 0.0166 4 1 d . . .
H1o1m H 0.8840(19) 0.3887(19) 0.201(2) Uiso 0.0222 4 1 d . . .
H1n24 H 0.743(3) 0.1216(8) 0.274(2) Uiso 0.0176 4 1 d . . .
H2n67 H 0.475(3) 0.605(2) -0.0021(12) Uiso 0.0246 4 1 d . . .
H1o3m H 0.188(3) 0.440(2) 0.221(3) Uiso 0.0464 4 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_type_symbol
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 Br 0.01936(16) 0.01587(15) 0.01995(17) -0.00020(11) 0.00203(12) 0.00208(12)
Br2 Br 0.01878(16) 0.02400(17) 0.02522(18) -0.00452(12) 0.00274(13)
-0.00917(13)
Zn1 Zn 0.01460(16) 0.01039(16) 0.00902(17) 0.00057(12) -0.00196(13) 0.00054(12)
N1 N 0.0115(11) 0.0154(11) 0.0100(12) -0.0008(9) 0.0005(9) 0.0015(10)
C2 C 0.0118(13) 0.0204(14) 0.0099(14) 0.0002(11) 0.0014(11) 0.0028(12)
C3 C 0.0117(14) 0.0284(16) 0.0140(15) 0.0043(12) -0.0004(12) 0.0046(13)
C4 C 0.0164(15) 0.0323(17) 0.0116(15) -0.0019(13) -0.0040(12) -0.0018(13)
C5 C 0.0181(14) 0.0221(15) 0.0135(15) -0.0038(12) 0.0005(12) -0.0032(12)
C6 C 0.0118(13) 0.0181(14) 0.0116(14) -0.0012(11) 0.0026(11) -0.0018(12)
C21 C 0.0171(14) 0.0172(14) 0.0127(15) 0.0051(11) 0.0030(12) 0.0046(12)
C22 C 0.0339(19) 0.0255(17) 0.0220(18) 0.0136(14) -0.0049(15) 0.0024(14)
N23 N 0.0137(11) 0.0116(11) 0.0114(12) 0.0012(9) 0.0012(9) -0.0001(9)
N24 N 0.0220(13) 0.0095(11) 0.0119(12) 0.0050(9) -0.0015(10) 0.0010(10)
C25 C 0.0108(13) 0.0135(13) 0.0147(15) 0.0001(10) 0.0047(11) -0.0013(11)
O26 O 0.0209(10) 0.0095(9) 0.0125(10) 0.0013(8) -0.0041(8) 0.0008(8)
N27 N 0.0212(13) 0.0098(11) 0.0161(14) -0.0004(10) 0.0013(11) -0.0013(10)
C61 C 0.0135(13) 0.0139(13) 0.0107(14) -0.0029(10) 0.0047(11) -0.0003(11)
C62 C 0.0217(15) 0.0166(14) 0.0144(15) -0.0036(11) 0.0017(12) -0.0028(12)
N63 N 0.0160(12) 0.0119(11) 0.0096(12) -0.0001(9) -0.0005(9) 0.0006(9)
N64 N 0.0240(13) 0.0071(10) 0.0098(12) 0.0033(9) -0.0019(10) 0.0010(9)
C65 C 0.0181(14) 0.0143(14) 0.0128(15) 0.0015(11) -0.0008(12) 0.0021(11)
O66 O 0.0271(11) 0.0097(9) 0.0117(10) 0.0021(8) -0.0060(9) -0.0004(8)
N67 N 0.0391(16) 0.0086(11) 0.0123(13) 0.0042(11) -0.0063(12) 0.0005(10)
O1m O 0.0193(11) 0.0190(11) 0.0181(11) -0.0005(8) 0.0060(9) 0.0018(9)
C2m C 0.0275(18) 0.0254(17) 0.033(2) -0.0080(14) 0.0042(15) 0.0033(15)
O3m O 0.0698(19) 0.0190(12) 0.0269(14) -0.0173(12) 0.0029(13) -0.0008(11)
C4m C 0.046(3) 0.037(2) 0.068(3) -0.0021(19) 0.006(2) 0.005(2)

loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zn1 N1 . . 2.205(2) ?
Zn1 N23 . . 2.207(2) ?
N1 C2 . . 1.340(3) ?
N1 C6 . . 1.339(3) ?
C2 C3 . . 1.391(4) ?
C2 C21 . . 1.481(4) ?
C3 C4 . . 1.388(4) ?
C3 H1c3 . . 0.96 ?
C4 C5 . . 1.379(4) ?
C4 H1c4 . . 0.96 ?
C5 C6 . . 1.387(4) ?
C5 H1c5 . . 0.96 ?
C6 C61 . . 1.484(4) ?
C21 C22 . . 1.495(4) ?
C21 N23 . . 1.286(3) ?
C22 H1c22 . . 0.96 ?
C22 H2c22 . . 0.96 ?
C22 H3c22 . . 0.96 ?
N23 N24 . . 1.359(3) ?
N24 C25 . . 1.378(4) ?
N24 H1n24 . . 0.880(15) ?
C25 O26 . . 1.236(3) ?
C25 N27 . . 1.337(4) ?
N27 H1n27 . . 0.880(16) ?
N27 H2n27 . . 0.880(18) ?
C61 C62 . . 1.492(4) ?
C61 N63 . . 1.277(3) ?
C62 H1c62 . . 0.96 ?
C62 H2c62 . . 0.96 ?
C62 H3c62 . . 0.96 ?
N63 N64 . . 1.362(3) ?
N64 C65 . . 1.368(4) ?
N64 H1n64 . . 0.880(7) ?
C65 O66 . . 1.251(3) ?
C65 N67 . . 1.325(4) ?
N67 H1n67 . . 0.880(7) ?
N67 H2n67 . . 0.880(19) ?
O1m C2m . . 1.416(4) ?
O1m H1o1m . . 0.84(2) ?
C2m H1c2m . . 0.96 ?
C2m H2c2m . . 0.96 ?
C2m H3c2m . . 0.96 ?
O3m C4m . . 1.337(5) ?
O3m H1o3m . . 0.84(3) ?
C4m H1c4m . . 0.96 ?
C4m H2c4m . . 0.96 ?
C4m H3c4m . . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 Zn1 N23 . . . 70.88(8) ?
Br1 N1 C2 . . . 109.78(16) ?
Br1 N1 C6 . . . 107.48(16) ?
Zn1 N1 C2 . . . 118.97(18) ?
Zn1 N1 C6 . . . 120.70(17) ?
C2 N1 C6 . . . 120.3(2) ?
N1 C2 C3 . . . 121.4(3) ?
N1 C2 C21 . . . 114.7(2) ?
C3 C2 C21 . . . 123.9(2) ?
C2 C3 C4 . . . 118.0(3) ?
C2 C3 H1c3 . . . 121.01 ?
C4 C3 H1c3 . . . 121.01 ?
C3 C4 C5 . . . 120.5(3) ?
C3 C4 H1c4 . . . 119.77 ?
C5 C4 H1c4 . . . 119.77 ?
C4 C5 C6 . . . 118.3(3) ?
C4 C5 H1c5 . . . 120.84 ?
C6 C5 H1c5 . . . 120.84 ?
N1 C6 C5 . . . 121.5(2) ?
N1 C6 C61 . . . 114.3(2) ?
C5 C6 C61 . . . 124.2(2) ?
C2 C21 C22 . . . 120.0(2) ?
C2 C21 N23 . . . 113.7(2) ?
C22 C21 N23 . . . 126.3(3) ?
C21 C22 H1c22 . . . 109.47 ?
C21 C22 H2c22 . . . 109.47 ?
C21 C22 H3c22 . . . 109.47 ?
H1c22 C22 H2c22 . . . 109.47 ?
H1c22 C22 H3c22 . . . 109.47 ?
H2c22 C22 H3c22 . . . 109.47 ?
Br1 N23 C21 . . . 113.01(18) ?
Br1 N23 N24 . . . 104.99(15) ?
Zn1 N23 C21 . . . 121.66(18) ?
Zn1 N23 N24 . . . 116.00(16) ?
C21 N23 N24 . . . 122.3(2) ?
N23 N24 C25 . . . 114.8(2) ?
N23 N24 H1n24 . . . 125.4(18) ?
C25 N24 H1n24 . . . 119.7(18) ?
N24 C25 O26 . . . 121.0(2) ?
N24 C25 N27 . . . 115.2(2) ?
O26 C25 N27 . . . 123.7(2) ?
C25 N27 H1n27 . . . 120.9(17) ?
C25 N27 H2n27 . . . 118(2) ?
H1n27 N27 H2n27 . . . 121(3) ?
C6 C61 C62 . . . 121.8(2) ?
C6 C61 N63 . . . 113.1(2) ?
C62 C61 N63 . . . 125.1(2) ?
C61 C62 H1c62 . . . 109.47 ?
C61 C62 H2c62 . . . 109.47 ?
C61 C62 H3c62 . . . 109.47 ?
H1c62 C62 H2c62 . . . 109.47 ?
H1c62 C62 H3c62 . . . 109.47 ?
H2c62 C62 H3c62 . . . 109.47 ?
Br1 N63 C61 . . . 107.21(17) ?
Br1 N63 N64 . . . 107.66(14) ?
C61 N63 N64 . . . 122.4(2) ?
N63 N64 C65 . . . 114.6(2) ?
N63 N64 H1n64 . . . 121.8(19) ?
C65 N64 H1n64 . . . 123.1(19) ?
N64 C65 O66 . . . 119.8(2) ?
N64 C65 N67 . . . 116.7(2) ?
O66 C65 N67 . . . 123.5(3) ?
C65 N67 H1n67 . . . 125(2) ?
C65 N67 H2n67 . . . 121.2(19) ?
H1n67 N67 H2n67 . . . 114(3) ?
C2m O1m H1o1m . . . 107.1(17) ?
O1m C2m H1c2m . . . 109.47 ?
O1m C2m H2c2m . . . 109.47 ?
O1m C2m H3c2m . . . 109.47 ?
H1c2m C2m H2c2m . . . 109.47 ?
H1c2m C2m H3c2m . . . 109.47 ?
H2c2m C2m H3c2m . . . 109.47 ?
C4m O3m H1o3m . . . 110(2) ?
O3m C4m H1c4m . . . 109.47 ?
O3m C4m H2c4m . . . 109.47 ?
O3m C4m H3c4m . . . 109.47 ?
H1c4m C4m H2c4m . . . 109.47 ?
H1c4m C4m H3c4m . . . 109.47 ?
H2c4m C4m H3c4m . . . 109.47 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1m H1o1m Br2 . . 1_655 0.84(2) 2.38(2) 3.214(2) 173(3) ?
N24 H1n24 O3m . . 2_645 0.880(15) 1.895(13) 2.769(3) 172(3) ?
N67 H2n67 O66 . . 3_665 0.880(19) 2.03(2) 2.891(3) 167(3) ?
O3m H1o3m Br2 . . . 0.84(3) 2.45(3) 3.270(3) 167(3) ?

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1506144'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;
_publcif_datablock.id            {dde0ed06-88f2-4c4a-986b-74b61a3a1d4a}

#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C13 H23 N7 O4 Zn, Br2 Cl2 Zn'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C13 H23 Br2 Cl2 N7 O4 Zn2'
_chemical_formula_weight         702.8
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
_cell_length_a                   7.5332(4)
_cell_length_b                   11.2812(5)
_cell_length_c                   15.5208(6)
_cell_angle_alpha                101.693(4)
_cell_angle_beta                 98.883(4)
_cell_angle_gamma                105.224(4)
_cell_volume                     1215.85(11)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            2

_cell_measurement_reflns_used    7479
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      29.33
_cell_measurement_temperature    120.00(14)
_cell_special_details            ?

_exptl_crystal_density_diffrn    1.9192
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             692

_exptl_absorpt_coefficient_mu    5.506
_exptl_crystal_description       ?
_exptl_crystal_size_max          0.724
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.104
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
analytical: 
   CrysAlisPro, Agilent Technologies, Version 1.171.35.19
   Analytical numeric absorption correction based on crystal shape
;
_exptl_absorpt_correction_T_min  0.18
_exptl_absorpt_correction_T_max  0.591

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      120
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean 10.3784
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            19188
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         29.39
_diffrn_reflns_theta_full        27.77
_diffrn_measured_fraction_theta_max 0.89
_diffrn_measured_fraction_theta_full 0.98
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          x-ray

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          ?

_reflns_number_total             5995
_reflns_number_gt                4829
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_gt          0.1118
_refine_ls_R_factor_all          0.0532
_refine_ls_wR_factor_ref         0.1190
_refine_ls_goodness_of_fit_ref   1.65
_refine_ls_goodness_of_fit_gt    1.74
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         5995
_refine_ls_number_parameters     302
_refine_ls_number_restraints     9
_refine_ls_number_constraints    69
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0016I²)
_refine_ls_hydrogen_treatment    mixed
_refine_ls_shift/su_max          0.0408
_refine_ls_shift/su_mean         0.0049
_refine_diff_density_max         0.90
_refine_diff_density_min         -1.18
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
Br -0.2901 2.4595 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
Cl 0.1484 0.1585 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0106 0.0060 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
Zn 0.2839 1.4301 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.32516(6) 0.58243(4) 0.28257(3) Uani 0.01644(15) 2 1 d . . .
O26 O 0.4254(4) 0.5056(2) 0.38920(17) Uani 0.0222(9) 2 1 d . . .
O66 O 0.3037(4) 0.7145(2) 0.40205(17) Uani 0.0225(10) 2 1 d . . .
O1m O 0.6113(4) 0.6867(3) 0.29863(18) Uani 0.0247(10) 2 1 d . . .
N1 N 0.2813(4) 0.5484(3) 0.13453(19) Uani 0.0167(10) 2 1 d . . .
N27 N 0.5366(5) 0.3532(3) 0.4318(2) Uani 0.0229(12) 2 1 d . . .
O3m O 0.0427(4) 0.4735(3) 0.27402(20) Uani 0.0273(10) 2 1 d . . .
N67 N 0.2512(5) 0.9009(3) 0.4591(2) Uani 0.0246(12) 2 1 d . . .
N64 N 0.2202(5) 0.8293(3) 0.3073(2) Uani 0.0208(11) 2 1 d . . .
N23 N 0.3791(4) 0.4006(3) 0.22182(19) Uani 0.0158(10) 2 1 d . . .
N63 N 0.2365(4) 0.7380(3) 0.2391(2) Uani 0.0182(10) 2 1 d . . .
C22 C 0.3636(6) 0.2257(4) 0.0937(3) Uani 0.0260(14) 2 1 d . . .
N24 N 0.4334(5) 0.3387(3) 0.2824(2) Uani 0.0195(11) 2 1 d . . .
C5 C 0.2160(5) 0.6212(4) 0.0024(2) Uani 0.0212(13) 2 1 d . . .
C2 C 0.2962(5) 0.4408(3) 0.0842(2) Uani 0.0164(12) 2 1 d . . .
C65 C 0.2612(5) 0.8111(3) 0.3918(2) Uani 0.0199(13) 2 1 d . . .
C3 C 0.2673(5) 0.4179(4) -0.0086(2) Uani 0.0215(13) 2 1 d . . .
C21 C 0.3490(5) 0.3545(3) 0.1365(2) Uani 0.0177(12) 2 1 d . . .
C6 C 0.2410(5) 0.6369(3) 0.0956(2) Uani 0.0173(12) 2 1 d . . .
C25 C 0.4636(5) 0.4028(3) 0.3708(2) Uani 0.0174(12) 2 1 d . . .
C4 C 0.2274(5) 0.5088(4) -0.0495(3) Uani 0.0221(13) 2 1 d . . .
C62 C 0.1956(6) 0.8609(4) 0.1259(3) Uani 0.0247(14) 2 1 d . . .
C2m C 0.7313(7) 0.7605(5) 0.3839(3) Uani 0.0391(18) 2 1 d . . .
C61 C 0.2226(5) 0.7490(3) 0.1584(2) Uani 0.0186(12) 2 1 d . . .
C4m C -0.0366(8) 0.4599(5) 0.3503(4) Uani 0.054(2) 2 1 d . . .
H1c22 H 0.352162 0.215766 0.029974 Uiso 0.0312 2 1 d . . .
H2c22 H 0.483474 0.218932 0.119767 Uiso 0.0312 2 1 d . . .
H3c22 H 0.26435 0.160633 0.104112 Uiso 0.0312 2 1 d . . .
H1c5 H 0.191683 0.686081 -0.02483 Uiso 0.0254 2 1 d . . .
H1c3 H 0.274906 0.339938 -0.044218 Uiso 0.0258 2 1 d . . .
H1c4 H 0.207618 0.494236 -0.113895 Uiso 0.0266 2 1 d . . .
H1c2m H 0.835512 0.822917 0.374439 Uiso 0.047 2 1 d . . .
H2c2m H 0.661032 0.802242 0.419413 Uiso 0.047 2 1 d . . .
H3c2m H 0.777856 0.705685 0.415111 Uiso 0.047 2 1 d . . .
H1c4m H -0.159765 0.398644 0.330827 Uiso 0.0647 2 1 d . . .
H2c4m H 0.042839 0.431733 0.390861 Uiso 0.0647 2 1 d . . .
H3c4m H -0.046535 0.540286 0.380566 Uiso 0.0647 2 1 d . . .
H1n27 H 0.544(6) 0.384(4) 0.4888(7) Uiso 0.0275 2 1 d . . .
H1n67 H 0.278(6) 0.897(4) 0.5148(9) Uiso 0.0296 2 1 d . . .
H2n27 H 0.560(6) 0.281(2) 0.420(3) Uiso 0.0275 2 1 d . . .
H2n67 H 0.213(6) 0.966(3) 0.454(3) Uiso 0.0296 2 1 d . . .
H1n24 H 0.447(6) 0.2653(18) 0.260(2) Uiso 0.0234 2 1 d . . .
H1n64 H 0.192(6) 0.896(2) 0.298(3) Uiso 0.025 2 1 d . . .
H1o1m H 0.634(5) 0.726(3) 0.2608(17) Uiso 0.0296 2 1 d . . .
H1o3m H 0.011(6) 0.4036(15) 0.2381(19) Uiso 0.0328 2 1 d . . .
H1c62 H 0.298603 0.89436 0.099411 Uiso 0.0297 2 1 d . . .
H2c62 H 0.07936 0.834626 0.08169 Uiso 0.0297 2 1 d . . .
H3c62 H 0.191554 0.925367 0.175902 Uiso 0.0297 2 1 d . . .
Zn2a Zn 0.8210(3) 0.05931(18) 0.24819(8) Uani 0.01886(19) 2 0.7616(15) d . . .
Br1a Br 1.0939(4) 0.1072(2) 0.36370(12) Uani 0.0311(3) 2 0.7616(15) d . . .
Br2a Br 0.8786(4) 0.1867(2) 0.14626(12) Uani 0.0388(3) 2 0.7616(15) d . . .
Cl1a Cl 0.5824(5) 0.0840(3) 0.3144(2) Uani 0.0216(7) 2 0.7616(15) d . . .
Cl2a Cl 0.7088(5) -0.1442(3) 0.1666(2) Uani 0.0279(7) 2 0.7616(15) d . . .
Zn2b Zn 0.8151(9) 0.0599(5) 0.2482(2) Uani 0.0189(3) 2 0.2383(15) d . . .
Br1b Br 0.5682(9) 0.0992(6) 0.3162(3) Uani 0.0311(3) 2 0.2383(15) d . . .
Br2b Br 0.7315(9) -0.1546(6) 0.1667(3) Uani 0.0388(4) 2 0.2383(15) d . . .
Cl1b Cl 1.0786(10) 0.1186(6) 0.3578(3) Uani 0.0216(7) 2 0.2383(15) d . . .
Cl2b Cl 0.9024(10) 0.1797(6) 0.1534(3) Uani 0.0279(8) 2 0.2383(15) d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zn1 N1 . . 2.209(3) ?
O26 C25 . . 1.255(5) ?
O66 C65 . . 1.246(5) ?
O1m C2m . . 1.432(4) ?
O1m H1o1m . . 0.82(3) ?
N1 C2 . . 1.346(5) ?
N1 C6 . . 1.342(5) ?
N27 C25 . . 1.315(5) ?
N27 H1n27 . . 0.870(15) ?
N27 H2n27 . . 0.87(3) ?
O3m C4m . . 1.423(7) ?
O3m H1o3m . . 0.820(19) ?
N67 C65 . . 1.326(5) ?
N67 H1n67 . . 0.87(2) ?
N67 H2n67 . . 0.87(4) ?
N64 N63 . . 1.364(4) ?
N64 C65 . . 1.369(5) ?
N64 H1n64 . . 0.87(3) ?
N23 N24 . . 1.355(5) ?
N23 C21 . . 1.282(4) ?
N63 C61 . . 1.275(5) ?
C22 C21 . . 1.509(6) ?
C22 H1c22 . . 0.96 ?
C22 H2c22 . . 0.96 ?
C22 H3c22 . . 0.96 ?
N24 C25 . . 1.368(4) ?
N24 H1n24 . . 0.87(3) ?
C5 C6 . . 1.396(5) ?
C5 C4 . . 1.389(6) ?
C5 H1c5 . . 0.96 ?
C2 C3 . . 1.383(5) ?
C2 C21 . . 1.479(6) ?
C3 C4 . . 1.382(6) ?
C3 H1c3 . . 0.96 ?
C6 C61 . . 1.485(5) ?
C4 H1c4 . . 0.96 ?
C62 C61 . . 1.500(6) ?
C62 H1c62 . . 0.96 ?
C62 H2c62 . . 0.96 ?
C62 H3c62 . . 0.96 ?
C2m H1c2m . . 0.96 ?
C2m H2c2m . . 0.96 ?
C2m H3c2m . . 0.96 ?
C4m H1c4m . . 0.96 ?
C4m H2c4m . . 0.96 ?
C4m H3c4m . . 0.96 ?
Zn2a Br1a . . 2.370(3) ?
Zn2a Br2a . . 2.359(3) ?
Zn2a Cl1a . . 2.255(5) ?
Zn2a Cl2a . . 2.250(3) ?
Zn2b Br1b . . 2.370(10) ?
Zn2b Br2b . . 2.359(8) ?
Zn2b Cl1b . . 2.255(8) ?
Zn2b Cl2b . . 2.250(8) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2m O1m H1o1m . . . 108.3(18) ?
Zn1 N1 C2 . . . 120.4(3) ?
Zn1 N1 C6 . . . 119.1(2) ?
C2 N1 C6 . . . 120.5(3) ?
C25 N27 H1n27 . . . 121(3) ?
C25 N27 H2n27 . . . 124(3) ?
H1n27 N27 H2n27 . . . 114(4) ?
C4m O3m H1o3m . . . 108(2) ?
C65 N67 H1n67 . . . 121(3) ?
C65 N67 H2n67 . . . 126(3) ?
H1n67 N67 H2n67 . . . 113(4) ?
N63 N64 C65 . . . 115.1(3) ?
N63 N64 H1n64 . . . 122(3) ?
C65 N64 H1n64 . . . 123(3) ?
N24 N23 C21 . . . 122.5(3) ?
N64 N63 C61 . . . 122.1(4) ?
C21 C22 H1c22 . . . 109.47 ?
C21 C22 H2c22 . . . 109.47 ?
C21 C22 H3c22 . . . 109.47 ?
H1c22 C22 H2c22 . . . 109.47 ?
H1c22 C22 H3c22 . . . 109.47 ?
H2c22 C22 H3c22 . . . 109.47 ?
N23 N24 C25 . . . 114.8(3) ?
N23 N24 H1n24 . . . 116(3) ?
C25 N24 H1n24 . . . 129(3) ?
C6 C5 C4 . . . 118.0(4) ?
C6 C5 H1c5 . . . 120.98 ?
C4 C5 H1c5 . . . 120.98 ?
N1 C2 C3 . . . 120.9(4) ?
N1 C2 C21 . . . 114.6(3) ?
C3 C2 C21 . . . 124.5(3) ?
O66 C65 N67 . . . 123.8(4) ?
O66 C65 N64 . . . 120.3(3) ?
N67 C65 N64 . . . 115.8(4) ?
C2 C3 C4 . . . 119.2(4) ?
C2 C3 H1c3 . . . 120.41 ?
C4 C3 H1c3 . . . 120.41 ?
N23 C21 C22 . . . 123.9(4) ?
N23 C21 C2 . . . 112.6(3) ?
C22 C21 C2 . . . 123.5(3) ?
N1 C6 C5 . . . 121.3(3) ?
N1 C6 C61 . . . 115.0(3) ?
C5 C6 C61 . . . 123.6(4) ?
O26 C25 N27 . . . 123.8(3) ?
O26 C25 N24 . . . 119.2(4) ?
N27 C25 N24 . . . 117.0(4) ?
C5 C4 C3 . . . 120.0(4) ?
C5 C4 H1c4 . . . 119.99 ?
C3 C4 H1c4 . . . 119.99 ?
C61 C62 H1c62 . . . 109.47 ?
C61 C62 H2c62 . . . 109.47 ?
C61 C62 H3c62 . . . 109.47 ?
H1c62 C62 H2c62 . . . 109.47 ?
H1c62 C62 H3c62 . . . 109.47 ?
H2c62 C62 H3c62 . . . 109.47 ?
O1m C2m H1c2m . . . 109.47 ?
O1m C2m H2c2m . . . 109.47 ?
O1m C2m H3c2m . . . 109.47 ?
H1c2m C2m H2c2m . . . 109.47 ?
H1c2m C2m H3c2m . . . 109.47 ?
H2c2m C2m H3c2m . . . 109.47 ?
N63 C61 C6 . . . 112.5(4) ?
N63 C61 C62 . . . 126.5(3) ?
C6 C61 C62 . . . 121.0(3) ?
O3m C4m H1c4m . . . 109.47 ?
O3m C4m H2c4m . . . 109.47 ?
O3m C4m H3c4m . . . 109.47 ?
H1c4m C4m H2c4m . . . 109.47 ?
H1c4m C4m H3c4m . . . 109.47 ?
H2c4m C4m H3c4m . . . 109.47 ?
Br1a Zn2a Br2a . . . 110.67(11) ?
Br1a Zn2a Cl1a . . . 107.88(12) ?
Br1a Zn2a Cl2a . . . 115.31(15) ?
Br2a Zn2a Cl1a . . . 112.98(16) ?
Br2a Zn2a Cl2a . . . 107.23(11) ?
Cl1a Zn2a Cl2a . . . 102.64(15) ?
Br1b Zn2b Br2b . . . 110.7(3) ?
Br1b Zn2b Cl1b . . . 107.9(3) ?
Br1b Zn2b Cl2b . . . 115.3(4) ?
Br2b Zn2b Cl1b . . . 113.0(4) ?
Br2b Zn2b Cl2b . . . 107.2(2) ?
Cl1b Zn2b Cl2b . . . 102.6(3) ?


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N27 H1n27 O26 . . 2_666 0.870(15) 1.99(2) 2.838(4) 166(4) ?
N27 H1n27 O66 . . 2_666 0.870(15) 2.50(4) 3.000(5) 117(4) ?
N27 H2n27 Br1b . . . 0.87(3) 2.36(3) 3.146(7) 151(4) ?
N24 H1n24 C22 . . . 0.87(3) 2.48(4) 2.852(5) 107(3) ?
O1m H1o1m Cl2a . . 1_565 0.82(3) 2.30(3) 3.113(5) 174(2) ?
O1m H1o1m Br2b . . 1_565 0.82(3) 2.26(3) 3.071(6) 173(3) ?
O3m H1o3m Br2a . . 1_455 0.820(19) 2.424(17) 3.236(3) 170(4) ?
O3m H1o3m Cl2b . . 1_455 0.820(19) 2.452(18) 3.262(6) 170(3) ?

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
####################################################################### 
# 
# 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_hydrmn_p21_100k
_database_code_depnum_ccdc_archive 'CCDC 1506145'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H32 Mn4 N8 O24'
_chemical_formula_weight         892.21

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   16.137(5)
_cell_length_b                   7.605(3)
_cell_length_c                   16.140(5)
_cell_angle_alpha                90
_cell_angle_beta                 119.984(3)
_cell_angle_gamma                90
_cell_volume                     1715.6(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9085
_cell_measurement_theta_min      2.9010
_cell_measurement_theta_max      29.3500

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.135
_exptl_absorpt_coefficient_mu    1.536
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87370
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            24249
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.678
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6731
_reflns_number_gt                6380
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component twin., Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0229P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2714 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6731
_refine_ls_number_parameters     477
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0580
_refine_ls_wR_factor_gt          0.0565
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 1.18312(9) 0.3767(2) 0.33396(10) 0.0114(2) Uani 1 1 d . . . . .
Mn2 Mn 1.33400(10) 0.8766(2) 0.15101(9) 0.0117(2) Uani 1 1 d . . . . .
Mn3 Mn 0.84923(9) 0.87659(11) 0.18289(9) 0.0115(2) Uani 1 1 d . . . . .
Mn4 Mn 0.66678(10) 0.35722(10) 0.33332(10) 0.0118(2) Uani 1 1 d . . . . .
C1 C 1.0145(6) 0.6125(10) 0.2890(6) 0.0164(18) Uani 1 1 d . . . . .
H1 H 0.9967 0.5782 0.2256 0.020 Uiso 1 1 calc R U . . .
C2 C 1.2265(6) 0.6319(10) 0.2169(6) 0.0196(18) Uani 1 1 d . . . . .
H2 H 1.2883 0.6246 0.2721 0.024 Uiso 1 1 calc R U . . .
C3 C 0.7397(5) 0.6026(10) 0.2361(5) 0.0172(14) Uani 1 1 d . . . . .
H3 H 0.7968 0.5950 0.2963 0.021 Uiso 1 1 calc R U . . .
C4 C 1.3005(6) 0.6058(10) 0.5075(5) 0.0152(17) Uani 1 1 d . . . . .
H4 H 1.2423 0.5931 0.5083 0.018 Uiso 1 1 calc R U . . .
C5 C 1.2742(5) 0.6118(10) -0.0139(5) 0.0174(19) Uani 1 1 d . . . . .
H5 H 1.2291 0.5773 0.0043 0.021 Uiso 1 1 calc R U . . .
C6 C 0.4957(5) 0.6037(10) 0.2604(6) 0.0169(19) Uani 1 1 d . . . . .
H6 H 0.4976 0.5941 0.2026 0.020 Uiso 1 1 calc R U . . .
C7 C 1.0117(5) 0.1315(9) 0.2279(6) 0.0169(18) Uani 1 1 d . . . . .
H7 H 1.0200 0.1219 0.2903 0.020 Uiso 1 1 calc R U . . .
C8 C 0.7938(5) 1.1055(11) 0.2988(5) 0.0168(15) Uani 1 1 d . . . . .
H8 H 0.7357 1.0950 0.2397 0.020 Uiso 1 1 calc R U . . .
C9 C 0.7829(6) 0.6300(10) 0.0105(6) 0.0182(19) Uani 1 1 d . . . . .
H9 H 0.7288 0.6181 0.0187 0.022 Uiso 1 1 calc R U . . .
C10 C 0.5067(5) 0.1057(10) 0.2074(5) 0.0143(18) Uani 1 1 d . . . . .
H10 H 0.5069 0.0942 0.2661 0.017 Uiso 1 1 calc R U . . .
C11 C 0.7654(6) 0.6032(11) 0.5057(6) 0.021(2) Uani 1 1 d . . . . .
H11 H 0.7063 0.5925 0.5048 0.025 Uiso 1 1 calc R U . . .
C12 C 1.2888(5) 1.1127(9) 0.2740(5) 0.0154(17) Uani 1 1 d . . . . .
H12 H 1.2253 1.0795 0.2280 0.019 Uiso 1 1 calc R U . . .
O1 O 1.2185(4) 0.7240(8) 0.1482(4) 0.0161(12) Uani 1 1 d . . . . .
O2 O 1.0820(4) 0.5306(8) 0.3563(3) 0.0184(12) Uani 1 1 d . . . . .
O3 O 0.7398(3) 0.7057(7) 0.1752(3) 0.0181(12) Uani 1 1 d . . . . .
O4 O 0.9684(3) 0.7366(6) 0.2989(3) 0.0152(11) Uani 1 1 d . . . . .
O5 O 0.6718(3) 0.5103(8) 0.2243(3) 0.0178(13) Uani 1 1 d . . . . .
O6 O 1.1614(4) 0.5507(8) 0.2188(4) 0.0213(13) Uani 1 1 d . . . . .
O7 O 1.0704(4) 0.2238(8) 0.2184(4) 0.0165(13) Uani 1 1 d . . . . .
O8 O 0.7760(3) 0.5115(7) 0.4478(4) 0.0191(12) Uani 1 1 d . . . . .
O9 O 0.8645(4) 1.0218(8) 0.3073(3) 0.0175(12) Uani 1 1 d . . . . .
O10 O 0.5692(4) 0.2037(7) 0.2069(3) 0.0146(12) Uani 1 1 d . . . . .
O11 O 1.3562(4) 1.0308(8) 0.2746(4) 0.0190(12) Uani 1 1 d . . . . .
O12 O 1.3072(4) 0.5224(8) 0.4432(4) 0.0184(13) Uani 1 1 d . . . . .
O13 O 0.8520(4) 0.7240(7) 0.0702(4) 0.0164(12) Uani 1 1 d . . . . .
O14 O 1.3307(4) 0.7368(7) 0.0312(3) 0.0186(12) Uani 1 1 d . . . . .
O15 O 1.2746(4) 0.5309(7) -0.0815(4) 0.0173(13) Uani 1 1 d . . . . .
O16 O 0.7928(3) 0.2029(7) 0.3619(3) 0.0153(12) Uani 1 1 d . . . . .
O17 O 0.4434(3) 0.0211(7) 0.1362(3) 0.0174(12) Uani 1 1 d . . . . .
O18 O 0.5527(4) 0.5121(7) 0.3281(3) 0.0171(13) Uani 1 1 d . . . . .
O19 O 0.9426(4) 0.0502(8) 0.1616(4) 0.0223(13) Uani 1 1 d . . . . .
O20 O 0.7813(3) 0.5531(8) -0.0577(4) 0.0199(13) Uani 1 1 d . . . . .
O21 O 1.3620(3) 0.7021(7) 0.5692(4) 0.0147(11) Uani 1 1 d . . . . .
O22 O 0.8245(3) 0.7065(7) 0.5642(3) 0.0174(12) Uani 1 1 d . . . . .
O23 O 0.4360(4) 0.7075(8) 0.2603(4) 0.0178(12) Uani 1 1 d . . . . .
O24 O 1.2994(3) 1.2367(7) 0.3305(4) 0.0174(12) Uani 1 1 d . . . . .
N1 N 1.0361(3) 0.8564(9) 0.4868(3) 0.0176(12) Uani 1 1 d D . . . .
H1A H 1.0925 0.8271 0.5331 0.021 Uiso 1 1 d R U . . .
H1B H 1.0330 0.8310 0.4326 0.021 Uiso 1 1 d R U . . .
N2 N 0.9602(3) 0.7664(7) 0.4934(3) 0.0199(12) Uani 1 1 d D . . . .
H2A H 0.9566 0.8094 0.5441 0.024 Uiso 1 1 calc R U . . .
H2B H 0.9731 0.6492 0.5017 0.024 Uiso 1 1 calc R U . . .
H2C H 0.9036 0.7843 0.4387 0.024 Uiso 1 1 calc R U . . .
N3 N 0.4863(3) 0.3561(7) 0.4502(3) 0.0164(12) Uani 1 1 d D . . . .
H3A H 0.4273 0.3372 0.3986 0.020 Uiso 1 1 calc R U . . .
H3B H 0.5319 0.3153 0.4377 0.020 Uiso 1 1 calc R U . . .
H3C H 0.4949 0.4734 0.4628 0.020 Uiso 1 1 calc R U . . .
N4 N 0.4937(4) 0.2642(6) 0.5327(3) 0.0179(11) Uani 1 1 d D . . . .
H4A H 0.5466 0.2965 0.5838 0.021 Uiso 1 1 d R U . . .
H4B H 0.4458 0.2841 0.5430 0.021 Uiso 1 1 d R U . . .
N5 N 0.5486(3) 0.3563(7) 0.0349(3) 0.0173(12) Uani 1 1 d D . . . .
H5A H 0.6004 0.3358 0.0280 0.021 Uiso 1 1 calc R U . . .
H5B H 0.5609 0.3175 0.0933 0.021 Uiso 1 1 calc R U . . .
H5C H 0.5361 0.4737 0.0299 0.021 Uiso 1 1 calc R U . . .
N6 N 0.4664(4) 0.2634(7) -0.0393(3) 0.0201(12) Uani 1 1 d D . . . .
H6A H 0.465(4) 0.313(8) -0.084(4) 0.024 Uiso 1 1 d . U . . .
H6B H 0.416(4) 0.324(8) -0.036(4) 0.024 Uiso 1 1 d . U . . .
N7 N 1.0365(12) 0.175(2) 0.0316(11) 0.018(3) Uiso 0.3333 1 d D U P A 1
H7A H 1.0312 0.0756 -0.0024 0.022 Uiso 0.3333 1 calc R U P A 1
H7B H 1.0078 0.1568 0.0672 0.022 Uiso 0.3333 1 calc R U P A 1
H7C H 1.0994 0.2001 0.0710 0.022 Uiso 0.3333 1 calc R U P A 1
N8 N 0.9904(16) 0.320(2) -0.0336(15) 0.022(4) Uani 0.3333 1 d D U P A 1
H8A H 0.9309 0.2948 -0.0757 0.027 Uiso 0.3333 1 d R U P A 1
H8B H 0.9898 0.4112 -0.0010 0.027 Uiso 0.3333 1 d R U P A 1
N9 N 0.9686(11) 0.175(2) 0.0045(13) 0.026(4) Uani 0.3333 1 d D U P B 2
H9A H 0.9318 0.1627 -0.0600 0.032 Uiso 0.3333 1 calc R U P B 2
H9B H 0.9305 0.1987 0.0298 0.032 Uiso 0.3333 1 calc R U P B 2
H9C H 1.0013 0.0733 0.0302 0.032 Uiso 0.3333 1 calc R U P B 2
N10 N 1.0356(14) 0.318(2) 0.0261(14) 0.019(4) Uani 0.3333 1 d D U P B 2
H10A H 1.0726 0.2947 0.0024 0.023 Uiso 0.3333 1 d R U P B 2
H10B H 1.0048 0.4153 0.0000 0.023 Uiso 0.3333 1 d R U P B 2
N11 N 0.9734(16) 0.317(2) 0.0103(15) 0.021(4) Uani 0.3333 1 d D U P C 3
H11A H 0.9126 0.3212 -0.0110 0.025 Uiso 0.3333 1 d R U P C 3
H11B H 1.0029 0.3000 0.0712 0.025 Uiso 0.3333 1 d R U P C 3
N12 N 0.9951(11) 0.177(2) -0.0366(11) 0.016(4) Uani 0.3333 1 d D U P C 3
H12A H 0.9587 0.1895 -0.1012 0.019 Uiso 0.3333 1 calc R U P C 3
H12B H 0.9821 0.0712 -0.0191 0.019 Uiso 0.3333 1 calc R U P C 3
H12C H 1.0581 0.1815 -0.0191 0.019 Uiso 0.3333 1 calc R U P C 3


_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 O22 2.144(5) 2_746 ?
Mn1 O6 2.163(6) . ?
Mn1 O7 2.179(5) . ?
Mn1 O2 2.180(5) . ?
Mn1 O24 2.183(5) 1_545 ?
Mn1 O12 2.195(5) . ?
Mn2 O23 2.139(5) 1_655 ?
Mn2 O20 2.175(5) 2_755 ?
Mn2 O1 2.177(5) . ?
Mn2 O11 2.184(5) . ?
Mn2 O14 2.185(5) . ?
Mn2 O17 2.191(5) 1_665 ?
Mn3 O3 2.145(5) . ?
Mn3 O19 2.157(5) 1_565 ?
Mn3 O4 2.177(4) . ?
Mn3 O13 2.177(5) . ?
Mn3 O15 2.187(5) 2_755 ?
Mn3 O9 2.195(5) . ?
Mn4 O5 2.145(5) . ?
Mn4 O18 2.151(5) . ?
Mn4 O8 2.155(5) . ?
Mn4 O16 2.189(5) . ?
Mn4 O10 2.190(5) . ?
Mn4 O21 2.193(5) 2_746 ?
C1 O2 1.254(9) . ?
C1 O4 1.260(9) . ?
C1 H1 0.9500 . ?
C2 O6 1.232(10) . ?
C2 O1 1.263(9) . ?
C2 H2 0.9500 . ?
C3 O5 1.233(9) . ?
C3 O3 1.258(9) . ?
C3 H3 0.9500 . ?
C4 O21 1.235(9) . ?
C4 O12 1.265(9) . ?
C4 H4 0.9500 . ?
C5 O15 1.255(9) . ?
C5 O14 1.266(9) . ?
C5 H5 0.9500 . ?
C6 O18 1.233(9) . ?
C6 O23 1.245(9) . ?
C6 H6 0.9500 . ?
C7 O7 1.248(9) . ?
C7 O19 1.256(9) . ?
C7 H7 0.9500 . ?
C8 O9 1.251(10) . ?
C8 O16 1.265(10) 1_565 ?
C8 H8 0.9500 . ?
C9 O20 1.236(10) . ?
C9 O13 1.269(9) . ?
C9 H9 0.9500 . ?
C10 O10 1.257(8) . ?
C10 O17 1.266(9) . ?
C10 H10 0.9500 . ?
C11 O22 1.232(9) . ?
C11 O8 1.244(10) . ?
C11 H11 0.9500 . ?
C12 O11 1.250(9) . ?
C12 O24 1.262(9) . ?
C12 H12 0.9500 . ?
O15 Mn3 2.187(5) 2_745 ?
O16 C8 1.265(10) 1_545 ?
O17 Mn2 2.191(5) 1_445 ?
O19 Mn3 2.157(5) 1_545 ?
O20 Mn2 2.175(5) 2_745 ?
O21 Mn4 2.193(5) 2_756 ?
O22 Mn1 2.144(5) 2_756 ?
O23 Mn2 2.139(5) 1_455 ?
O24 Mn1 2.183(5) 1_565 ?
N1 N2 1.452(4) . ?
N1 H1A 0.8698 . ?
N1 H1B 0.8716 . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
N3 N4 1.454(4) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N4 H4A 0.8751 . ?
N4 H4B 0.8819 . ?
N5 N6 1.451(5) . ?
N5 H5A 0.9100 . ?
N5 H5B 0.9100 . ?
N5 H5C 0.9100 . ?
N6 H6A 0.81(6) . ?
N6 H6B 0.96(6) . ?
N7 N8 1.449(6) . ?
N7 H7A 0.9100 . ?
N7 H7B 0.9100 . ?
N7 H7C 0.9100 . ?
N8 H8A 0.8757 . ?
N8 H8B 0.8730 . ?
N9 N10 1.447(6) . ?
N9 H9A 0.9100 . ?
N9 H9B 0.9100 . ?
N9 H9C 0.9100 . ?
N10 H10A 0.8726 . ?
N10 H10B 0.8755 . ?
N11 N12 1.449(6) . ?
N11 H11A 0.8627 . ?
N11 H11B 0.8620 . ?
N12 H12A 0.9100 . ?
N12 H12B 0.9100 . ?
N12 H12C 0.9100 . ?

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
O22 Mn1 O6 169.04(19) 2_746 . ?
O22 Mn1 O7 89.5(2) 2_746 . ?
O6 Mn1 O7 83.3(2) . . ?
O22 Mn1 O2 82.10(17) 2_746 . ?
O6 Mn1 O2 90.0(2) . . ?
O7 Mn1 O2 93.1(2) . . ?
O22 Mn1 O24 96.03(19) 2_746 1_545 ?
O6 Mn1 O24 92.76(18) . 1_545 ?
O7 Mn1 O24 94.5(2) . 1_545 ?
O2 Mn1 O24 172.2(2) . 1_545 ?
O22 Mn1 O12 93.9(2) 2_746 . ?
O6 Mn1 O12 94.2(2) . . ?
O7 Mn1 O12 173.30(16) . . ?
O2 Mn1 O12 93.1(2) . . ?
O24 Mn1 O12 79.4(2) 1_545 . ?
O23 Mn2 O20 169.06(15) 1_655 2_755 ?
O23 Mn2 O1 89.7(2) 1_655 . ?
O20 Mn2 O1 83.5(2) 2_755 . ?
O23 Mn2 O11 82.1(2) 1_655 . ?
O20 Mn2 O11 89.7(2) 2_755 . ?
O1 Mn2 O11 93.07(15) . . ?
O23 Mn2 O14 96.0(2) 1_655 . ?
O20 Mn2 O14 93.1(2) 2_755 . ?
O1 Mn2 O14 94.6(2) . . ?
O11 Mn2 O14 172.1(2) . . ?
O23 Mn2 O17 93.5(2) 1_655 1_665 ?
O20 Mn2 O17 94.2(2) 2_755 1_665 ?
O1 Mn2 O17 173.25(19) . 1_665 ?
O11 Mn2 O17 93.3(2) . 1_665 ?
O14 Mn2 O17 79.17(16) . 1_665 ?
O3 Mn3 O19 169.16(19) . 1_565 ?
O3 Mn3 O4 95.85(19) . . ?
O19 Mn3 O4 92.8(2) 1_565 . ?
O3 Mn3 O13 89.36(19) . . ?
O19 Mn3 O13 83.4(2) 1_565 . ?
O4 Mn3 O13 94.5(2) . . ?
O3 Mn3 O15 82.2(2) . 2_755 ?
O19 Mn3 O15 90.1(2) 1_565 2_755 ?
O4 Mn3 O15 172.1(2) . 2_755 ?
O13 Mn3 O15 93.08(19) . 2_755 ?
O3 Mn3 O9 94.0(2) . . ?
O19 Mn3 O9 94.0(2) 1_565 . ?
O4 Mn3 O9 79.21(19) . . ?
O13 Mn3 O9 173.15(19) . . ?
O15 Mn3 O9 93.27(19) 2_755 . ?
O5 Mn4 O18 93.01(19) . . ?
O5 Mn4 O8 93.3(2) . . ?
O18 Mn4 O8 93.0(2) . . ?
O5 Mn4 O16 93.0(2) . . ?
O18 Mn4 O16 171.46(19) . . ?
O8 Mn4 O16 80.5(2) . . ?
O5 Mn4 O10 80.2(2) . . ?
O18 Mn4 O10 93.0(2) . . ?
O8 Mn4 O10 171.4(2) . . ?
O16 Mn4 O10 94.0(2) . . ?
O5 Mn4 O21 171.3(2) . 2_746 ?
O18 Mn4 O21 80.75(19) . 2_746 ?
O8 Mn4 O21 93.1(2) . 2_746 ?
O16 Mn4 O21 93.9(2) . 2_746 ?
O10 Mn4 O21 94.0(2) . 2_746 ?
O2 C1 O4 125.0(7) . . ?
O2 C1 H1 117.5 . . ?
O4 C1 H1 117.5 . . ?
O6 C2 O1 125.8(7) . . ?
O6 C2 H2 117.1 . . ?
O1 C2 H2 117.1 . . ?
O5 C3 O3 125.7(5) . . ?
O5 C3 H3 117.2 . . ?
O3 C3 H3 117.2 . . ?
O21 C4 O12 126.5(7) . . ?
O21 C4 H4 116.7 . . ?
O12 C4 H4 116.7 . . ?
O15 C5 O14 123.6(7) . . ?
O15 C5 H5 118.2 . . ?
O14 C5 H5 118.2 . . ?
O18 C6 O23 126.4(8) . . ?
O18 C6 H6 116.8 . . ?
O23 C6 H6 116.8 . . ?
O7 C7 O19 125.3(7) . . ?
O7 C7 H7 117.4 . . ?
O19 C7 H7 117.4 . . ?
O9 C8 O16 125.9(6) . 1_565 ?
O9 C8 H8 117.0 . . ?
O16 C8 H8 117.0 1_565 . ?
O20 C9 O13 124.2(8) . . ?
O20 C9 H9 117.9 . . ?
O13 C9 H9 117.9 . . ?
O10 C10 O17 125.6(7) . . ?
O10 C10 H10 117.2 . . ?
O17 C10 H10 117.2 . . ?
O22 C11 O8 126.0(8) . . ?
O22 C11 H11 117.0 . . ?
O8 C11 H11 117.0 . . ?
O11 C12 O24 124.2(6) . . ?
O11 C12 H12 117.9 . . ?
O24 C12 H12 117.9 . . ?
C2 O1 Mn2 124.5(5) . . ?
C1 O2 Mn1 121.4(5) . . ?
C3 O3 Mn3 130.9(5) . . ?
C1 O4 Mn3 125.5(5) . . ?
C3 O5 Mn4 125.3(4) . . ?
C2 O6 Mn1 123.7(5) . . ?
C7 O7 Mn1 123.7(5) . . ?
C11 O8 Mn4 126.1(5) . . ?
C8 O9 Mn3 118.4(5) . . ?
C10 O10 Mn4 121.1(5) . . ?
C12 O11 Mn2 121.0(5) . . ?
C4 O12 Mn1 119.6(5) . . ?
C9 O13 Mn3 123.9(5) . . ?
C5 O14 Mn2 124.5(5) . . ?
C5 O15 Mn3 120.9(4) . 2_745 ?
C8 O16 Mn4 121.9(4) 1_545 . ?
C10 O17 Mn2 119.0(4) . 1_445 ?
C6 O18 Mn4 126.1(5) . . ?
C7 O19 Mn3 124.0(5) . 1_545 ?
C9 O20 Mn2 122.6(5) . 2_745 ?
C4 O21 Mn4 121.7(5) . 2_756 ?
C11 O22 Mn1 130.8(5) . 2_756 ?
C6 O23 Mn2 131.2(5) . 1_455 ?
C12 O24 Mn1 125.1(4) . 1_565 ?
N2 N1 H1A 111.9 . . ?
N2 N1 H1B 109.9 . . ?
H1A N1 H1B 108.5 . . ?
N1 N2 H2A 109.5 . . ?
N1 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
N1 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
N4 N3 H3A 109.5 . . ?
N4 N3 H3B 109.5 . . ?
H3A N3 H3B 109.5 . . ?
N4 N3 H3C 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
N3 N4 H4A 108.9 . . ?
N3 N4 H4B 114.3 . . ?
H4A N4 H4B 107.8 . . ?
N6 N5 H5A 109.5 . . ?
N6 N5 H5B 109.5 . . ?
H5A N5 H5B 109.5 . . ?
N6 N5 H5C 109.5 . . ?
H5A N5 H5C 109.5 . . ?
H5B N5 H5C 109.5 . . ?
N5 N6 H6A 97(4) . . ?
N5 N6 H6B 100(3) . . ?
H6A N6 H6B 100(5) . . ?
N8 N7 H7A 109.5 . . ?
N8 N7 H7B 109.5 . . ?
H7A N7 H7B 109.5 . . ?
N8 N7 H7C 109.5 . . ?
H7A N7 H7C 109.5 . . ?
H7B N7 H7C 109.5 . . ?
N7 N8 H8A 111.3 . . ?
N7 N8 H8B 109.0 . . ?
H8A N8 H8B 107.7 . . ?
N10 N9 H9A 109.5 . . ?
N10 N9 H9B 109.5 . . ?
H9A N9 H9B 109.5 . . ?
N10 N9 H9C 109.5 . . ?
H9A N9 H9C 109.5 . . ?
H9B N9 H9C 109.5 . . ?
N9 N10 H10A 109.7 . . ?
N9 N10 H10B 110.1 . . ?
H10A N10 H10B 107.9 . . ?
N12 N11 H11A 110.0 . . ?
N12 N11 H11B 110.2 . . ?
H11A N11 H11B 109.3 . . ?
N11 N12 H12A 109.5 . . ?
N11 N12 H12B 109.5 . . ?
H12A N12 H12B 109.5 . . ?
N11 N12 H12C 109.5 . . ?
H12A N12 H12C 109.5 . . ?
H12B N12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 C2 O1 Mn2 176.6(6) . . . . ?
O4 C1 O2 Mn1 -161.2(6) . . . . ?
O5 C3 O3 Mn3 179.3(5) . . . . ?
O2 C1 O4 Mn3 -178.6(6) . . . . ?
O3 C3 O5 Mn4 -172.7(6) . . . . ?
O1 C2 O6 Mn1 174.2(6) . . . . ?
O19 C7 O7 Mn1 175.6(6) . . . . ?
O22 C11 O8 Mn4 -171.3(6) . . . . ?
O16 C8 O9 Mn3 -175.9(6) 1_565 . . . ?
O17 C10 O10 Mn4 175.2(6) . . . . ?
O24 C12 O11 Mn2 -161.5(5) . . . . ?
O21 C4 O12 Mn1 -174.9(6) . . . . ?
O20 C9 O13 Mn3 174.7(6) . . . . ?
O15 C5 O14 Mn2 -178.6(5) . . . . ?
O14 C5 O15 Mn3 -161.0(5) . . . 2_745 ?
O10 C10 O17 Mn2 -174.7(6) . . . 1_445 ?
O23 C6 O18 Mn4 -172.1(6) . . . . ?
O7 C7 O19 Mn3 175.2(6) . . . 1_545 ?
O13 C9 O20 Mn2 174.9(5) . . . 2_745 ?
O12 C4 O21 Mn4 173.9(6) . . . 2_756 ?
O8 C11 O22 Mn1 178.5(6) . . . 2_756 ?
O18 C6 O23 Mn2 179.2(6) . . . 1_455 ?
O11 C12 O24 Mn1 -178.0(5) . . . 1_565 ?

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
C4 H4 O2 0.95 2.57 3.181(9) 122.4 .
C7 H7 O22 0.95 2.52 3.115(9) 121.1 2_746
C8 H8 O15 0.95 2.52 3.158(9) 124.5 2_755
C9 H9 O3 0.95 2.53 3.119(10) 120.2 .
C10 H10 O11 0.95 2.55 3.167(9) 122.9 1_445
N1 H1B O4 0.87 2.00 2.813(7) 154.0 .
N1 H1A O16 0.87 2.01 2.865(7) 166.0 2_756
N2 H2B N1 0.91 2.25 3.132(8) 164.6 2_746
N3 H3B O21 0.91 1.97 2.870(7) 170.0 2_746
N3 H3A O24 0.91 1.95 2.798(7) 155.2 1_445
N3 H3C N4 0.91 2.22 3.118(7) 170.4 2_656
N5 H5B O10 0.91 1.97 2.871(7) 169.9 .
N5 H5A O14 0.91 1.94 2.798(7) 155.8 2_745
N5 H5C N6 0.91 2.21 3.110(7) 169.3 2_655
N7 H7B O7 0.91 2.18 2.807(16) 125.0 .
N7 H7C O20 0.91 2.33 2.905(16) 121.3 2_745
N7 H7A N8 0.91 2.11 2.73(2) 125.1 2_745
N8 H8A O1 0.88 2.16 3.01(2) 165.7 2_745
N8 H8B N7 0.87 2.06 2.73(2) 133.9 2_755
N9 H9A O1 0.91 2.16 2.809(17) 127.4 2_745
N9 H9B O19 0.91 2.33 2.927(18) 123.1 .
N9 H9C N10 0.91 2.10 2.76(2) 127.8 2_745
N10 H10A O13 0.87 2.14 3.00(2) 172.9 2_745
N10 H10B N9 0.88 2.03 2.76(2) 139.7 2_755
N11 H11A O1 0.86 2.29 2.95(2) 133.7 2_745
N11 H11B O7 0.86 2.14 3.00(2) 172.7 .
N12 H12A O6 0.91 2.19 2.919(16) 136.6 2_745
N12 H12C O13 0.91 2.02 2.801(16) 142.9 2_745
N12 H12B N11 0.91 2.04 2.78(2) 136.8 2_745

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.062

