# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1539792'
_audit_update_record             
;
2017-03-23 deposited with the CCDC.
2017-05-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H30 N8 O10 Sr, H2 O'
_chemical_formula_sum            'C28 H32 N8 O11 Sr'
_chemical_formula_weight         744.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Sr Sr -1.5307 3.2498 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'

_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'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   14.200(2)
_cell_length_b                   14.200(2)
_cell_length_c                   17.207(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3469.4(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2254
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      18.82

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             1528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.621
_shelx_estimated_absorpt_T_min   0.660
_shelx_estimated_absorpt_T_max   0.738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6597
_exptl_absorpt_correction_T_max  0.7376
_exptl_absorpt_process_details   'SADABS(sheldrick, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18907
_diffrn_reflns_av_unetI/netI     0.0823
_diffrn_reflns_av_R_equivalents  0.0919
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.859
_diffrn_reflns_theta_max         25.993
_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             3421
_reflns_number_gt                2529
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_max     0.999
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0752P)²] 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 827 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3421
_refine_ls_number_parameters     221
_refine_ls_number_restraints     162
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.089
_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
Sr1 Sr 0.61013(4) 0.61013(4) 0.0000 0.0356(3) Uani 1 2 d S T P . .
C1 C 0.6602(5) 0.7766(5) 0.1441(4) 0.0385(17) Uani 1 1 d . U . . .
C3 C 0.8385(5) 0.7603(5) 0.1674(5) 0.0424(17) Uani 1 1 d . U . . .
C2 C 0.7550(5) 0.7356(5) 0.1330(4) 0.0354(16) Uani 1 1 d . U . . .
C4 C 0.8643(5) 0.8238(6) 0.2327(5) 0.053(2) Uani 1 1 d . U . . .
C5 C 0.8618(5) 0.6487(5) 0.0826(4) 0.0386(17) Uani 1 1 d . U . . .
N1 N 0.7708(4) 0.6664(4) 0.0797(3) 0.0367(14) Uani 1 1 d . . . . .
N2 N 0.9046(4) 0.7048(4) 0.1338(3) 0.0430(15) Uani 1 1 d . . . . .
H2 H 0.9639 0.7055 0.1438 0.052 Uiso 1 1 calc R U . . .
C6 C 0.9137(6) 0.5738(6) 0.0363(5) 0.049(2) Uani 1 1 d . U . . .
H6A H 0.8776 0.5582 -0.0098 0.059 Uiso 1 1 calc R U . . .
H6B H 0.9741 0.5985 0.0196 0.059 Uiso 1 1 calc R U . . .
C7 C 0.9291(6) 0.4861(6) 0.0835(5) 0.056(2) Uani 1 1 d . U . . .
C9 C 1.0279(9) 0.3638(8) 0.1329(7) 0.093(3) Uani 1 1 d . U . . .
H9 H 1.0872 0.3363 0.1369 0.111 Uiso 1 1 calc R U . . .
N3 N 0.8626(7) 0.3609(7) 0.1670(6) 0.103(3) Uani 1 1 d . . . . .
C11 C 0.8566(7) 0.4414(7) 0.1240(6) 0.072(3) Uani 1 1 d . U . . .
H11 H 0.7975 0.4695 0.1213 0.087 Uiso 1 1 calc R U . . .
C8 C 1.0159(7) 0.4464(8) 0.0899(6) 0.076(3) Uani 1 1 d . U . . .
H8 H 1.0674 0.4742 0.0657 0.092 Uiso 1 1 calc R U . . .
C10 C 0.9520(10) 0.3236(9) 0.1690(7) 0.097(3) Uani 1 1 d . U . . .
H10 H 0.9613 0.2679 0.1965 0.116 Uiso 1 1 calc R U . . .
O3 O 0.7988(4) 0.8798(6) 0.2576(5) 0.092(3) Uani 1 1 d . . . . .
H3 H 0.7506 0.8713 0.2324 0.138 Uiso 1 1 calc R U . . .
O4 O 0.9457(4) 0.8249(5) 0.2582(4) 0.0634(16) Uani 1 1 d . . . . .
O1 O 0.5949(3) 0.7442(4) 0.1043(3) 0.0456(13) Uani 1 1 d . . . . .
O2 O 0.6492(3) 0.8412(4) 0.1930(4) 0.0636(17) Uani 1 1 d . . . . .
O5 O 0.5106(6) 0.5327(6) 0.1047(5) 0.113(3) Uani 1 1 d . . . . .
N4 N 0.4257(11) 0.4301(10) 0.1814(8) 0.147(4) Uani 1 1 d . U . . .
C12 C 0.5086(13) 0.4568(11) 0.1429(9) 0.139(5) Uani 1 1 d . U . . .
H12 H 0.5618 0.4188 0.1456 0.167 Uiso 1 1 calc R U . . .
C13 C 0.4376(13) 0.3424(13) 0.2293(10) 0.176(6) Uani 1 1 d . U . . .
H13A H 0.4029 0.2918 0.2060 0.263 Uiso 1 1 calc R U . . .
H13B H 0.4144 0.3535 0.2809 0.263 Uiso 1 1 calc R U . . .
H13C H 0.5031 0.3260 0.2317 0.263 Uiso 1 1 calc R U . . .
C14 C 0.3406(14) 0.4935(14) 0.1856(12) 0.191(8) Uani 1 1 d . U . . .
H14A H 0.3249 0.5050 0.2391 0.286 Uiso 1 1 calc R U . . .
H14B H 0.2884 0.4636 0.1601 0.286 Uiso 1 1 calc R U . . .
H14C H 0.3543 0.5522 0.1603 0.286 Uiso 1 1 calc R U . . .
O1W O 0.6788(11) 0.3212(11) 0.2500 0.280(13) Uani 1 2 d S T P . .
H1WB H 0.7356 0.3411 0.2617 0.336 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
Sr1 O4 2.515(5) 6_465 ?
Sr1 O4 2.515(5) 3_644 ?
Sr1 O5 2.539(7) . ?
Sr1 O5 2.539(7) 7 ?
Sr1 O1 2.625(5) . ?
Sr1 O1 2.625(5) 7 ?
Sr1 N1 2.779(5) . ?
Sr1 N1 2.779(5) 7 ?
C1 O1 1.241(8) . ?
C1 O2 1.254(8) . ?
C1 C2 1.479(10) . ?
C3 N2 1.355(9) . ?
C3 C2 1.372(10) . ?
C3 C4 1.486(11) . ?
C2 N1 1.363(9) . ?
C4 O4 1.236(9) . ?
C4 O3 1.296(9) . ?
C5 N1 1.318(9) . ?
C5 N2 1.335(9) . ?
C5 C6 1.520(10) . ?
N2 H2 0.8600 . ?
C6 C7 1.502(12) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.361(13) . ?
C7 C11 1.397(13) . ?
C9 C10 1.370(17) . ?
C9 C8 1.396(14) . ?
C9 H9 0.9300 . ?
N3 C11 1.365(13) . ?
N3 C10 1.375(14) . ?
C11 H11 0.9300 . ?
C8 H8 0.9300 . ?
C10 H10 0.9300 . ?
O3 H3 0.8200 . ?
O4 Sr1 2.515(5) 4_565 ?
O5 C12 1.263(15) . ?
N4 C12 1.402(18) . ?
N4 C13 1.50(2) . ?
N4 C14 1.51(2) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O1W H1WB 0.8778 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Sr1 O4 133.2(3) 6_465 3_644 ?
O4 Sr1 O5 71.5(3) 6_465 . ?
O4 Sr1 O5 76.2(2) 3_644 . ?
O4 Sr1 O5 76.2(2) 6_465 7 ?
O4 Sr1 O5 71.5(3) 3_644 7 ?
O5 Sr1 O5 91.2(4) . 7 ?
O4 Sr1 O1 72.30(17) 6_465 . ?
O4 Sr1 O1 131.69(18) 3_644 . ?
O5 Sr1 O1 77.5(2) . . ?
O5 Sr1 O1 148.5(2) 7 . ?
O4 Sr1 O1 131.69(18) 6_465 7 ?
O4 Sr1 O1 72.30(17) 3_644 7 ?
O5 Sr1 O1 148.5(2) . 7 ?
O5 Sr1 O1 77.5(2) 7 7 ?
O1 Sr1 O1 125.9(2) . 7 ?
O4 Sr1 N1 133.18(17) 6_465 . ?
O4 Sr1 N1 86.4(2) 3_644 . ?
O5 Sr1 N1 103.4(3) . . ?
O5 Sr1 N1 149.9(2) 7 . ?
O1 Sr1 N1 61.42(16) . . ?
O1 Sr1 N1 76.46(17) 7 . ?
O4 Sr1 N1 86.4(2) 6_465 7 ?
O4 Sr1 N1 133.18(17) 3_644 7 ?
O5 Sr1 N1 149.9(2) . 7 ?
O5 Sr1 N1 103.4(3) 7 7 ?
O1 Sr1 N1 76.46(17) . 7 ?
O1 Sr1 N1 61.42(16) 7 7 ?
N1 Sr1 N1 76.8(3) . 7 ?
O1 C1 O2 123.3(7) . . ?
O1 C1 C2 117.5(6) . . ?
O2 C1 C2 119.2(7) . . ?
N2 C3 C2 105.4(6) . . ?
N2 C3 C4 120.3(7) . . ?
C2 C3 C4 134.0(7) . . ?
N1 C2 C3 109.4(6) . . ?
N1 C2 C1 121.4(6) . . ?
C3 C2 C1 129.1(7) . . ?
O4 C4 O3 123.1(8) . . ?
O4 C4 C3 120.4(7) . . ?
O3 C4 C3 116.4(7) . . ?
N1 C5 N2 111.0(6) . . ?
N1 C5 C6 126.2(7) . . ?
N2 C5 C6 122.9(6) . . ?
C5 N1 C2 105.9(6) . . ?
C5 N1 Sr1 140.2(5) . . ?
C2 N1 Sr1 113.9(4) . . ?
C5 N2 C3 108.3(6) . . ?
C5 N2 H2 125.8 . . ?
C3 N2 H2 125.8 . . ?
C7 C6 C5 111.6(7) . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C11 116.0(9) . . ?
C8 C7 C6 121.3(9) . . ?
C11 C7 C6 122.6(8) . . ?
C10 C9 C8 119.6(11) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 N3 C10 113.3(11) . . ?
N3 C11 C7 127.2(9) . . ?
N3 C11 H11 116.4 . . ?
C7 C11 H11 116.4 . . ?
C7 C8 C9 120.1(11) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C9 C10 N3 123.6(11) . . ?
C9 C10 H10 118.2 . . ?
N3 C10 H10 118.2 . . ?
C4 O3 H3 109.5 . . ?
C4 O4 Sr1 148.5(6) . 4_565 ?
C1 O1 Sr1 125.8(4) . . ?
C12 O5 Sr1 138.8(10) . . ?
C12 N4 C13 112.9(16) . . ?
C12 N4 C14 122.3(14) . . ?
C13 N4 C14 123.9(13) . . ?
O5 C12 N4 119.7(16) . . ?
O5 C12 H12 120.1 . . ?
N4 C12 H12 120.1 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
N2 C3 C2 N1 0.0(8) . . . . ?
C4 C3 C2 N1 -173.9(9) . . . . ?
N2 C3 C2 C1 -176.5(7) . . . . ?
C4 C3 C2 C1 9.7(15) . . . . ?
O1 C1 C2 N1 1.6(10) . . . . ?
O2 C1 C2 N1 -178.9(7) . . . . ?
O1 C1 C2 C3 177.7(7) . . . . ?
O2 C1 C2 C3 -2.8(12) . . . . ?
N2 C3 C4 O4 -1.8(13) . . . . ?
C2 C3 C4 O4 171.3(9) . . . . ?
N2 C3 C4 O3 174.9(8) . . . . ?
C2 C3 C4 O3 -12.0(15) . . . . ?
N2 C5 N1 C2 -1.4(8) . . . . ?
C6 C5 N1 C2 177.3(7) . . . . ?
N2 C5 N1 Sr1 177.3(5) . . . . ?
C6 C5 N1 Sr1 -4.1(13) . . . . ?
C3 C2 N1 C5 0.9(8) . . . . ?
C1 C2 N1 C5 177.6(7) . . . . ?
C3 C2 N1 Sr1 -178.2(5) . . . . ?
C1 C2 N1 Sr1 -1.4(8) . . . . ?
N1 C5 N2 C3 1.4(9) . . . . ?
C6 C5 N2 C3 -177.3(7) . . . . ?
C2 C3 N2 C5 -0.8(8) . . . . ?
C4 C3 N2 C5 174.0(7) . . . . ?
N1 C5 C6 C7 -98.0(9) . . . . ?
N2 C5 C6 C7 80.5(9) . . . . ?
C5 C6 C7 C8 -128.7(9) . . . . ?
C5 C6 C7 C11 50.4(11) . . . . ?
C10 N3 C11 C7 0.6(17) . . . . ?
C8 C7 C11 N3 -2.3(16) . . . . ?
C6 C7 C11 N3 178.6(9) . . . . ?
C11 C7 C8 C9 2.2(14) . . . . ?
C6 C7 C8 C9 -178.7(9) . . . . ?
C10 C9 C8 C7 -0.6(17) . . . . ?
C8 C9 C10 N3 -1(2) . . . . ?
C11 N3 C10 C9 1.2(18) . . . . ?
O3 C4 O4 Sr1 -89.3(13) . . . 4_565 ?
C3 C4 O4 Sr1 87.2(12) . . . 4_565 ?
O2 C1 O1 Sr1 179.6(6) . . . . ?
C2 C1 O1 Sr1 -0.9(9) . . . . ?
Sr1 O5 C12 N4 -162.4(10) . . . . ?
C13 N4 C12 O5 -175.3(14) . . . . ?
C14 N4 C12 O5 -6(3) . . . . ?

_refine_diff_density_max         0.431
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1539789'
_audit_update_record             
;
2017-03-23 deposited with the CCDC.
2017-05-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 Ca2 N6 O10, H2 O'
_chemical_formula_sum            'C22 H20 Ca2 N6 O11'
_chemical_formula_weight         624.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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'

_cell_length_a                   8.860(5)
_cell_length_b                   11.293(6)
_cell_length_c                   12.717(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.088(7)
_cell_angle_gamma                90
_cell_volume                     1252.8(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2168
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.05

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.530
_shelx_estimated_absorpt_T_min   0.832
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8321
_exptl_absorpt_correction_T_max  0.9247
_exptl_absorpt_process_details   'SADABS(sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4636
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.803
_diffrn_reflns_theta_max         25.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.772
_diffrn_reflns_point_group_measured_fraction_full 0.772
_reflns_number_total             3510
_reflns_number_gt                3274
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.559
_reflns_Friedel_fraction_max     0.555
_reflns_Friedel_fraction_full    0.555

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0479P)²+0.0800P] 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 1094 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3510
_refine_ls_number_parameters     370
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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
C1 C 0.1436(6) 0.1705(4) 1.0373(4) 0.0324(12) Uani 1 1 d . . . . .
C2 C 0.1044(5) 0.1417(4) 1.1446(4) 0.0276(10) Uani 1 1 d . . . . .
C3 C 0.0118(5) 0.0645(4) 1.1871(4) 0.0256(10) Uani 1 1 d . . . . .
C4 C -0.0879(5) -0.0353(4) 1.1417(4) 0.0273(10) Uani 1 1 d . . . . .
C5 C 0.1283(6) 0.1712(4) 1.3178(4) 0.0294(11) Uani 1 1 d . . . . .
C6 C 0.1791(6) 0.2261(5) 1.4255(4) 0.0366(12) Uani 1 1 d . . . . .
H6A H 0.2360 0.2977 1.4165 0.044 Uiso 1 1 calc R U . . .
H6B H 0.0888 0.2491 1.4540 0.044 Uiso 1 1 calc R U . . .
C7 C 0.2756(6) 0.1497(5) 1.5051(4) 0.0343(12) Uani 1 1 d . . . . .
C8 C 0.3875(7) 0.0755(6) 1.4803(5) 0.0497(16) Uani 1 1 d . . . . .
H8 H 0.4051 0.0696 1.4105 0.060 Uiso 1 1 calc R U . . .
C9 C 0.2579(7) 0.1525(5) 1.6113(4) 0.0447(14) Uani 1 1 d . . . . .
H9 H 0.1834 0.2007 1.6323 0.054 Uiso 1 1 calc R U . . .
C10 C 0.4729(8) 0.0102(6) 1.5609(6) 0.0588(18) Uani 1 1 d . . . . .
H10 H 0.5471 -0.0403 1.5427 0.071 Uiso 1 1 calc R U . . .
C11 C 0.3504(8) 0.0842(6) 1.6856(5) 0.0537(17) Uani 1 1 d . . . . .
H11 H 0.3365 0.0879 1.7563 0.064 Uiso 1 1 calc R U . . .
C12 C 0.6097(5) 0.2735(4) 0.8815(4) 0.0281(11) Uani 1 1 d . . . . .
C13 C 0.5752(5) 0.3291(4) 0.7713(4) 0.0246(10) Uani 1 1 d . . . . .
C14 C 0.4933(5) 0.4235(4) 0.7252(4) 0.0228(10) Uani 1 1 d . . . . .
C15 C 0.4017(5) 0.5192(4) 0.7658(4) 0.0250(10) Uani 1 1 d . . . . .
C16 C 0.5987(5) 0.3428(4) 0.6026(4) 0.0240(10) Uani 1 1 d . . . . .
C17 C 0.6628(6) 0.3217(4) 0.5035(4) 0.0293(11) Uani 1 1 d . . . . .
H17A H 0.5878 0.3452 0.4421 0.035 Uiso 1 1 calc R U . . .
H17B H 0.6823 0.2377 0.4971 0.035 Uiso 1 1 calc R U . . .
C18 C 0.8084(6) 0.3887(4) 0.5031(4) 0.0304(11) Uani 1 1 d . . . . .
C19 C 0.9140(7) 0.4038(7) 0.5943(5) 0.0598(19) Uani 1 1 d . . . . .
H19 H 0.8951 0.3731 0.6585 0.072 Uiso 1 1 calc R U . . .
C20 C 0.8455(7) 0.4348(6) 0.4115(5) 0.0518(17) Uani 1 1 d . . . . .
H20 H 0.7772 0.4277 0.3474 0.062 Uiso 1 1 calc R U . . .
C21 C 1.0462(8) 0.4630(7) 0.5916(5) 0.0617(19) Uani 1 1 d . . . . .
H21 H 1.1141 0.4730 0.6555 0.074 Uiso 1 1 calc R U . . .
C22 C 0.9828(7) 0.4914(6) 0.4138(5) 0.0538(17) Uani 1 1 d . . . . .
H22 H 1.0058 0.5198 0.3498 0.065 Uiso 1 1 calc R U . . .
Ca1 Ca 0.85193(10) 0.03180(8) 0.88145(7) 0.0272(2) Uani 1 1 d . . . . .
Ca2 Ca 0.35408(10) 0.40897(8) 1.00772(7) 0.0270(2) Uani 1 1 d . . . . .
N1 N 0.0279(5) 0.0842(3) 1.2957(3) 0.0287(9) Uani 1 1 d . . . . .
N2 N 0.1767(5) 0.2073(3) 1.2290(3) 0.0290(9) Uani 1 1 d . . . . .
H2 H 0.2424 0.2625 1.2257 0.035 Uiso 1 1 calc R U . . .
N3 N 0.4571(6) 0.0141(5) 1.6616(5) 0.0551(14) Uani 1 1 d . . . . .
N4 N 0.6391(4) 0.2794(3) 0.6919(3) 0.0277(9) Uani 1 1 d . . . . .
H4 H 0.6961 0.2173 0.6982 0.033 Uiso 1 1 calc R U . . .
N5 N 0.5087(4) 0.4303(3) 0.6184(3) 0.0261(9) Uani 1 1 d . . . . .
N6 N 1.0853(5) 0.5081(4) 0.5027(4) 0.0422(11) Uani 1 1 d . . . . .
O1 O 0.2636(4) 0.2269(3) 1.0400(3) 0.0434(10) Uani 1 1 d . . . . .
O2 O 0.0563(5) 0.1414(4) 0.9546(3) 0.0501(10) Uani 1 1 d . . . . .
O3 O -0.1138(4) -0.0536(3) 1.0441(3) 0.0353(9) Uani 1 1 d . . . . .
O4 O -0.1410(4) -0.0967(3) 1.2082(3) 0.0362(9) Uani 1 1 d . . . . .
O5 O 0.6847(5) 0.1807(3) 0.8879(3) 0.0466(10) Uani 1 1 d . . . . .
O6 O 0.5616(4) 0.3219(3) 0.9571(3) 0.0382(9) Uani 1 1 d . . . . .
O7 O 0.3767(4) 0.5193(3) 0.8584(3) 0.0397(10) Uani 1 1 d . . . . .
O8 O 0.3557(4) 0.5981(3) 0.6979(3) 0.0358(9) Uani 1 1 d . . . . .
O1W O 0.1895(7) 0.3084(5) 0.8312(4) 0.0830(16) Uani 1 1 d . . . . .
H1WA H 0.0925 0.3136 0.8151 0.100 Uiso 1 1 d R U . . .
H1WB H 0.2105 0.2436 0.8646 0.100 Uiso 1 1 d R U . . .
O2W O 0.6657(5) -0.1062(4) 0.8049(3) 0.0514(11) Uani 1 1 d . . . . .
H2WA H 0.5942 -0.0922 0.7525 0.062 Uiso 1 1 d R U . . .
H2WB H 0.6634 -0.1796 0.8190 0.062 Uiso 1 1 d R U . . .
O3W O 0.7503(8) 0.7173(5) 0.6596(4) 0.0975(19) Uani 1 1 d . . . . .
H3WA H 0.6611 0.7089 0.6801 0.117 Uiso 1 1 d R U . . .
H3WB H 0.7824 0.7796 0.6931 0.117 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
C1 O1 1.234(6) . ?
C1 O2 1.236(6) . ?
C1 C2 1.502(7) . ?
C2 N2 1.368(6) . ?
C2 C3 1.372(7) . ?
C3 N1 1.380(6) . ?
C3 C4 1.486(7) . ?
C4 O3 1.240(6) . ?
C4 O4 1.247(6) . ?
C4 Ca1 3.186(5) 2_455 ?
C5 N1 1.322(6) . ?
C5 N2 1.340(6) . ?
C5 C6 1.498(7) . ?
C6 C7 1.482(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.376(8) . ?
C7 C9 1.388(8) . ?
C8 C10 1.376(9) . ?
C8 H8 0.9300 . ?
C9 C11 1.374(8) . ?
C9 H9 0.9300 . ?
C10 N3 1.314(9) . ?
C10 H10 0.9300 . ?
C11 N3 1.309(9) . ?
C11 H11 0.9300 . ?
C12 O5 1.236(6) . ?
C12 O6 1.245(6) . ?
C12 C13 1.517(7) . ?
C13 N4 1.362(6) . ?
C13 C14 1.363(6) . ?
C14 N5 1.391(6) . ?
C14 C15 1.496(6) . ?
C15 O7 1.236(6) . ?
C15 O8 1.258(6) . ?
C16 N5 1.307(6) . ?
C16 N4 1.337(6) . ?
C16 C17 1.489(6) . ?
C17 C18 1.496(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.367(8) . ?
C18 C20 1.368(8) . ?
C19 C21 1.354(9) . ?
C19 H19 0.9300 . ?
C20 C22 1.370(9) . ?
C20 H20 0.9300 . ?
C21 N6 1.339(8) . ?
C21 H21 0.9300 . ?
C22 N6 1.334(7) . ?
C22 H22 0.9300 . ?
Ca1 O5 2.252(4) . ?
Ca1 O3 2.254(3) 1_655 ?
Ca1 O2 2.255(4) 1_655 ?
Ca1 O4 2.333(4) 2_654 ?
Ca1 O2W 2.352(4) . ?
Ca1 N1 2.436(4) 2_654 ?
Ca1 C4 3.186(5) 2_654 ?
Ca2 O1 2.270(4) . ?
Ca2 O6 2.276(4) . ?
Ca2 O7 2.309(4) . ?
Ca2 O8 2.418(4) 2_565 ?
Ca2 N5 2.546(4) 2_565 ?
Ca2 N6 2.549(5) 2_465 ?
Ca2 O1W 2.703(6) . ?
Ca2 H1WB 2.7580 . ?
N1 Ca1 2.436(4) 2_455 ?
N2 H2 0.8600 . ?
N4 H4 0.8600 . ?
N5 Ca2 2.546(4) 2_564 ?
N6 Ca2 2.549(5) 2_664 ?
O2 Ca1 2.255(4) 1_455 ?
O3 Ca1 2.254(3) 1_455 ?
O4 Ca1 2.333(4) 2_455 ?
O8 Ca2 2.418(4) 2_564 ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8500 . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8501 . ?
O3W H3WA 0.8797 . ?
O3W H3WB 0.8462 . ?

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 C1 O2 124.7(5) . . ?
O1 C1 C2 114.9(5) . . ?
O2 C1 C2 120.4(4) . . ?
N2 C2 C3 105.3(4) . . ?
N2 C2 C1 116.5(4) . . ?
C3 C2 C1 138.2(5) . . ?
C2 C3 N1 109.2(4) . . ?
C2 C3 C4 133.2(4) . . ?
N1 C3 C4 117.4(4) . . ?
O3 C4 O4 124.1(4) . . ?
O3 C4 C3 120.6(4) . . ?
O4 C4 C3 115.3(4) . . ?
O3 C4 Ca1 158.1(3) . 2_455 ?
O4 C4 Ca1 38.0(2) . 2_455 ?
C3 C4 Ca1 78.8(3) . 2_455 ?
N1 C5 N2 110.4(4) . . ?
N1 C5 C6 125.8(4) . . ?
N2 C5 C6 123.7(4) . . ?
C7 C6 C5 115.4(4) . . ?
C7 C6 H6A 108.4 . . ?
C5 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
C5 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
C8 C7 C9 116.5(5) . . ?
C8 C7 C6 123.4(5) . . ?
C9 C7 C6 120.1(5) . . ?
C7 C8 C10 118.7(6) . . ?
C7 C8 H8 120.6 . . ?
C10 C8 H8 120.6 . . ?
C11 C9 C7 120.1(6) . . ?
C11 C9 H9 120.0 . . ?
C7 C9 H9 120.0 . . ?
N3 C10 C8 124.7(7) . . ?
N3 C10 H10 117.6 . . ?
C8 C10 H10 117.6 . . ?
N3 C11 C9 123.2(6) . . ?
N3 C11 H11 118.4 . . ?
C9 C11 H11 118.4 . . ?
O5 C12 O6 125.1(5) . . ?
O5 C12 C13 115.6(4) . . ?
O6 C12 C13 119.4(4) . . ?
N4 C13 C14 105.2(4) . . ?
N4 C13 C12 118.1(4) . . ?
C14 C13 C12 136.6(4) . . ?
C13 C14 N5 109.1(4) . . ?
C13 C14 C15 134.2(4) . . ?
N5 C14 C15 116.7(4) . . ?
O7 C15 O8 124.2(4) . . ?
O7 C15 C14 121.9(4) . . ?
O8 C15 C14 113.9(4) . . ?
N5 C16 N4 110.7(4) . . ?
N5 C16 C17 125.8(4) . . ?
N4 C16 C17 123.2(4) . . ?
C16 C17 C18 112.3(4) . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C20 116.3(5) . . ?
C19 C18 C17 121.5(5) . . ?
C20 C18 C17 122.1(5) . . ?
C21 C19 C18 120.5(6) . . ?
C21 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C18 C20 C22 120.3(6) . . ?
C18 C20 H20 119.8 . . ?
C22 C20 H20 119.8 . . ?
N6 C21 C19 124.2(6) . . ?
N6 C21 H21 117.9 . . ?
C19 C21 H21 117.9 . . ?
N6 C22 C20 123.6(6) . . ?
N6 C22 H22 118.2 . . ?
C20 C22 H22 118.2 . . ?
O5 Ca1 O3 105.63(14) . 1_655 ?
O5 Ca1 O2 93.49(17) . 1_655 ?
O3 Ca1 O2 83.52(14) 1_655 1_655 ?
O5 Ca1 O4 85.80(13) . 2_654 ?
O3 Ca1 O4 168.35(14) 1_655 2_654 ?
O2 Ca1 O4 93.70(14) 1_655 2_654 ?
O5 Ca1 O2W 95.24(17) . . ?
O3 Ca1 O2W 93.92(14) 1_655 . ?
O2 Ca1 O2W 171.26(17) 1_655 . ?
O4 Ca1 O2W 87.13(15) 2_654 . ?
O5 Ca1 N1 153.48(14) . 2_654 ?
O3 Ca1 N1 100.79(14) 1_655 2_654 ?
O2 Ca1 N1 87.09(16) 1_655 2_654 ?
O4 Ca1 N1 67.71(13) 2_654 2_654 ?
O2W Ca1 N1 85.18(15) . 2_654 ?
O5 Ca1 C4 104.31(13) . 2_654 ?
O3 Ca1 C4 149.92(13) 1_655 2_654 ?
O2 Ca1 C4 97.52(14) 1_655 2_654 ?
O4 Ca1 C4 19.22(12) 2_654 2_654 ?
O2W Ca1 C4 80.50(14) . 2_654 ?
N1 Ca1 C4 49.50(12) 2_654 2_654 ?
O1 Ca2 O6 89.35(14) . . ?
O1 Ca2 O7 136.19(14) . . ?
O6 Ca2 O7 79.02(13) . . ?
O1 Ca2 O8 74.30(13) . 2_565 ?
O6 Ca2 O8 113.92(13) . 2_565 ?
O7 Ca2 O8 148.70(13) . 2_565 ?
O1 Ca2 N5 135.95(13) . 2_565 ?
O6 Ca2 N5 94.67(14) . 2_565 ?
O7 Ca2 N5 87.38(14) . 2_565 ?
O8 Ca2 N5 64.02(12) 2_565 2_565 ?
O1 Ca2 N6 88.79(15) . 2_465 ?
O6 Ca2 N6 161.69(15) . 2_465 ?
O7 Ca2 N6 89.81(14) . 2_465 ?
O8 Ca2 N6 83.03(15) 2_565 2_465 ?
N5 Ca2 N6 99.31(14) 2_565 2_465 ?
O1 Ca2 O1W 67.26(15) . . ?
O6 Ca2 O1W 85.91(17) . . ?
O7 Ca2 O1W 69.86(15) . . ?
O8 Ca2 O1W 136.43(15) 2_565 . ?
N5 Ca2 O1W 156.74(14) 2_565 . ?
N6 Ca2 O1W 76.58(17) 2_465 . ?
O1 Ca2 H1WB 50.9 . . ?
O6 Ca2 H1WB 79.8 . . ?
O7 Ca2 H1WB 85.4 . . ?
O8 Ca2 H1WB 124.0 2_565 . ?
N5 Ca2 H1WB 171.6 2_565 . ?
N6 Ca2 H1WB 84.9 2_465 . ?
O1W Ca2 H1WB 17.9 . . ?
C5 N1 C3 106.3(4) . . ?
C5 N1 Ca1 139.8(3) . 2_455 ?
C3 N1 Ca1 113.5(3) . 2_455 ?
C5 N2 C2 108.8(4) . . ?
C5 N2 H2 125.6 . . ?
C2 N2 H2 125.6 . . ?
C11 N3 C10 116.9(6) . . ?
C16 N4 C13 109.0(4) . . ?
C16 N4 H4 125.5 . . ?
C13 N4 H4 125.5 . . ?
C16 N5 C14 106.0(4) . . ?
C16 N5 Ca2 137.5(3) . 2_564 ?
C14 N5 Ca2 116.3(3) . 2_564 ?
C22 N6 C21 115.0(5) . . ?
C22 N6 Ca2 124.6(4) . 2_664 ?
C21 N6 Ca2 119.8(4) . 2_664 ?
C1 O1 Ca2 142.4(4) . . ?
C1 O2 Ca1 146.6(3) . 1_455 ?
C4 O3 Ca1 145.0(3) . 1_455 ?
C4 O4 Ca1 122.8(3) . 2_455 ?
C12 O5 Ca1 168.6(4) . . ?
C12 O6 Ca2 144.2(4) . . ?
C15 O7 Ca2 147.0(3) . . ?
C15 O8 Ca2 127.4(3) . 2_564 ?
Ca2 O1W H1WA 123.1 . . ?
Ca2 O1W H1WB 84.7 . . ?
H1WA O1W H1WB 107.7 . . ?
Ca1 O2W H2WA 125.0 . . ?
Ca1 O2W H2WB 126.9 . . ?
H2WA O2W H2WB 107.7 . . ?
H3WA O3W H3WB 100.4 . . ?

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
O1 C1 C2 N2 18.1(7) . . . . ?
O2 C1 C2 N2 -159.6(5) . . . . ?
O1 C1 C2 C3 -161.9(6) . . . . ?
O2 C1 C2 C3 20.4(9) . . . . ?
N2 C2 C3 N1 0.3(5) . . . . ?
C1 C2 C3 N1 -179.6(6) . . . . ?
N2 C2 C3 C4 -175.0(5) . . . . ?
C1 C2 C3 C4 5.1(10) . . . . ?
C2 C3 C4 O3 -9.0(9) . . . . ?
N1 C3 C4 O3 176.0(4) . . . . ?
C2 C3 C4 O4 171.0(5) . . . . ?
N1 C3 C4 O4 -4.0(7) . . . . ?
C2 C3 C4 Ca1 -178.1(6) . . . 2_455 ?
N1 C3 C4 Ca1 6.9(4) . . . 2_455 ?
N1 C5 C6 C7 69.9(7) . . . . ?
N2 C5 C6 C7 -112.1(5) . . . . ?
C5 C6 C7 C8 39.3(7) . . . . ?
C5 C6 C7 C9 -142.1(5) . . . . ?
C9 C7 C8 C10 0.0(8) . . . . ?
C6 C7 C8 C10 178.6(5) . . . . ?
C8 C7 C9 C11 0.5(8) . . . . ?
C6 C7 C9 C11 -178.2(5) . . . . ?
C7 C8 C10 N3 -0.8(10) . . . . ?
C7 C9 C11 N3 -0.3(9) . . . . ?
O5 C12 C13 N4 -5.5(7) . . . . ?
O6 C12 C13 N4 175.0(4) . . . . ?
O5 C12 C13 C14 175.8(5) . . . . ?
O6 C12 C13 C14 -3.7(9) . . . . ?
N4 C13 C14 N5 -0.1(5) . . . . ?
C12 C13 C14 N5 178.7(5) . . . . ?
N4 C13 C14 C15 -176.8(5) . . . . ?
C12 C13 C14 C15 2.1(10) . . . . ?
C13 C14 C15 O7 -6.1(8) . . . . ?
N5 C14 C15 O7 177.5(4) . . . . ?
C13 C14 C15 O8 173.2(5) . . . . ?
N5 C14 C15 O8 -3.3(6) . . . . ?
N5 C16 C17 C18 85.9(6) . . . . ?
N4 C16 C17 C18 -87.3(6) . . . . ?
C16 C17 C18 C19 37.2(7) . . . . ?
C16 C17 C18 C20 -145.1(5) . . . . ?
C20 C18 C19 C21 0.9(10) . . . . ?
C17 C18 C19 C21 178.8(6) . . . . ?
C19 C18 C20 C22 0.6(9) . . . . ?
C17 C18 C20 C22 -177.3(6) . . . . ?
C18 C19 C21 N6 -1.5(12) . . . . ?
C18 C20 C22 N6 -1.8(11) . . . . ?
N2 C5 N1 C3 -0.2(5) . . . . ?
C6 C5 N1 C3 178.0(5) . . . . ?
N2 C5 N1 Ca1 -172.0(4) . . . 2_455 ?
C6 C5 N1 Ca1 6.3(8) . . . 2_455 ?
C2 C3 N1 C5 -0.1(5) . . . . ?
C4 C3 N1 C5 176.0(4) . . . . ?
C2 C3 N1 Ca1 174.1(3) . . . 2_455 ?
C4 C3 N1 Ca1 -9.7(5) . . . 2_455 ?
N1 C5 N2 C2 0.4(6) . . . . ?
C6 C5 N2 C2 -177.9(5) . . . . ?
C3 C2 N2 C5 -0.4(6) . . . . ?
C1 C2 N2 C5 179.5(4) . . . . ?
C9 C11 N3 C10 -0.5(10) . . . . ?
C8 C10 N3 C11 1.1(10) . . . . ?
N5 C16 N4 C13 -1.4(5) . . . . ?
C17 C16 N4 C13 172.7(4) . . . . ?
C14 C13 N4 C16 0.9(5) . . . . ?
C12 C13 N4 C16 -178.2(4) . . . . ?
N4 C16 N5 C14 1.2(5) . . . . ?
C17 C16 N5 C14 -172.7(4) . . . . ?
N4 C16 N5 Ca2 -174.7(3) . . . 2_564 ?
C17 C16 N5 Ca2 11.4(7) . . . 2_564 ?
C13 C14 N5 C16 -0.7(5) . . . . ?
C15 C14 N5 C16 176.6(4) . . . . ?
C13 C14 N5 Ca2 176.2(3) . . . 2_564 ?
C15 C14 N5 Ca2 -6.4(5) . . . 2_564 ?
C20 C22 N6 C21 1.3(10) . . . . ?
C20 C22 N6 Ca2 172.5(5) . . . 2_664 ?
C19 C21 N6 C22 0.3(11) . . . . ?
C19 C21 N6 Ca2 -171.3(6) . . . 2_664 ?
O2 C1 O1 Ca2 69.5(8) . . . . ?
C2 C1 O1 Ca2 -108.2(6) . . . . ?
O1 C1 O2 Ca1 169.4(5) . . . 1_455 ?
C2 C1 O2 Ca1 -13.1(10) . . . 1_455 ?
O4 C4 O3 Ca1 146.2(4) . . . 1_455 ?
C3 C4 O3 Ca1 -33.9(9) . . . 1_455 ?
Ca1 C4 O3 Ca1 116.2(8) 2_455 . . 1_455 ?
O3 C4 O4 Ca1 -162.4(4) . . . 2_455 ?
C3 C4 O4 Ca1 17.7(6) . . . 2_455 ?
O6 C12 O5 Ca1 -132.7(17) . . . . ?
C13 C12 O5 Ca1 48(2) . . . . ?
O5 C12 O6 Ca2 -134.2(5) . . . . ?
C13 C12 O6 Ca2 45.3(8) . . . . ?
O8 C15 O7 Ca2 155.8(5) . . . . ?
C14 C15 O7 Ca2 -25.1(9) . . . . ?
O7 C15 O8 Ca2 -167.4(4) . . . 2_564 ?
C14 C15 O8 Ca2 13.3(6) . . . 2_564 ?

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1539788'
_audit_update_record             
;
2017-03-23 deposited with the CCDC.
2017-05-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 Ca2 N6 O10'
_chemical_formula_sum            'C22 H18 Ca2 N6 O10'
_chemical_formula_weight         606.58

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'
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'
Ca Ca 0.2262 0.3064 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   14.991(5)
_cell_length_b                   6.826(3)
_cell_length_c                   25.261(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2585.0(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1300
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      22.29

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.509
_shelx_estimated_absorpt_T_min   0.892
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8920
_exptl_absorpt_correction_T_max  0.9415
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11981
_diffrn_reflns_av_unetI/netI     0.1062
_diffrn_reflns_av_R_equivalents  0.1089
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.612
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        24.993
_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             3422
_reflns_number_gt                2324
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.949
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion 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)+(0.0080P)²+68.2999P] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.22(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3422
_refine_ls_number_parameters     338
_refine_ls_number_restraints     415
_refine_ls_R_factor_all          0.1605
_refine_ls_R_factor_gt           0.1244
_refine_ls_wR_factor_ref         0.3064
_refine_ls_wR_factor_gt          0.2848
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.064
_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
C1 C 0.7659(7) 0.7384(16) 0.4489(5) 0.0289(12) Uani 1 1 d . U . . .
C2 C 0.6848(6) 0.7567(15) 0.4176(5) 0.027(2) Uani 1 1 d . U . . .
C3 C 0.6250(7) 0.8992(12) 0.4059(5) 0.0274(14) Uani 1 1 d D U . . .
C4 C 0.6191(7) 1.1146(11) 0.4192(5) 0.0273(15) Uani 1 1 d D U . . .
C5 C 0.5706(7) 0.6384(17) 0.3689(5) 0.033(2) Uani 1 1 d . U . . .
C6 C 0.5122(8) 0.4968(17) 0.3400(5) 0.0340(19) Uani 1 1 d . U . . .
H6A H 0.4503 0.5257 0.3480 0.041 Uiso 1 1 calc R U . . .
H6B H 0.5247 0.3652 0.3525 0.041 Uiso 1 1 calc R U . . .
C7 C 0.5255(5) 0.5041(12) 0.2810(3) 0.055(3) Uani 1 1 d G U . . .
C8 C 0.5652(7) 0.3418(13) 0.2576(4) 0.092(3) Uani 1 1 d G U . . .
H8 H 0.5842 0.2376 0.2784 0.110 Uiso 1 1 calc R U . . .
C9 C 0.5764(8) 0.3352(18) 0.2030(4) 0.109(3) Uani 1 1 d G U . . .
H9 H 0.6030 0.2265 0.1873 0.131 Uiso 1 1 calc R U . . .
N3 N 0.5480(8) 0.491(2) 0.1718(4) 0.092(3) Uani 1 1 d G U . . .
C11 C 0.5082(9) 0.6532(18) 0.1952(4) 0.101(3) Uani 1 1 d G U . . .
H11 H 0.4892 0.7573 0.1744 0.121 Uiso 1 1 calc R U . . .
C10 C 0.4970(7) 0.6598(13) 0.2498(4) 0.091(3) Uani 1 1 d G U . . .
H10 H 0.4704 0.7684 0.2655 0.109 Uiso 1 1 calc R U . . .
C12 C 0.9896(5) 1.2419(15) 0.5144(4) 0.027(2) Uani 1 1 d D U . . .
C13 C 1.0753(5) 1.2541(15) 0.5464(4) 0.0234(14) Uani 1 1 d D U . . .
C14 C 1.1381(6) 1.4070(15) 0.5586(5) 0.0240(12) Uani 1 1 d . U . . .
C15 C 1.1400(6) 1.6057(15) 0.5453(5) 0.0258(15) Uani 1 1 d . U . . .
C16 C 1.1870(7) 1.1370(18) 0.5936(6) 0.039(2) Uani 1 1 d . U . . .
C17 C 1.2391(11) 0.994(2) 0.6255(7) 0.0657(16) Uani 1 1 d . U . . .
H17A H 1.3019 1.0145 0.6182 0.079 Uiso 1 1 calc R U . . .
H17B H 1.2239 0.8634 0.6136 0.079 Uiso 1 1 calc R U . . .
C18 C 1.2259(6) 1.0029(13) 0.6842(4) 0.0706(15) Uani 1 1 d G U . . .
C19 C 1.1447(7) 0.9389(18) 0.7043(5) 0.103(3) Uani 1 1 d G U . . .
H19 H 1.0992 0.9016 0.6814 0.123 Uiso 1 1 calc R U . . .
C20 C 1.1314(9) 0.931(2) 0.7587(5) 0.117(4) Uani 1 1 d G U . . .
H20 H 1.0771 0.8880 0.7722 0.140 Uiso 1 1 calc R U . . .
N6 N 1.1994(11) 0.987(2) 0.7930(4) 0.115(4) Uani 1 1 d G U . . .
C22 C 1.2806(10) 1.051(2) 0.7728(5) 0.123(4) Uani 1 1 d G U . . .
H22 H 1.3261 1.0880 0.7958 0.148 Uiso 1 1 calc R U . . .
C21 C 1.2939(7) 1.0588(18) 0.7184(5) 0.110(3) Uani 1 1 d G U . . .
H21 H 1.3482 1.1016 0.7049 0.132 Uiso 1 1 calc R U . . .
Ca1 Ca 0.81810(12) 1.2379(3) 0.46808(10) 0.0304(6) Uani 1 1 d . . . . .
Ca2 Ca 0.94181(12) 1.7379(3) 0.49459(10) 0.0297(6) Uani 1 1 d . . . . .
N1 N 0.6545(6) 0.5855(14) 0.3929(4) 0.035(2) Uani 1 1 d . U . . .
H1 H 0.6804 0.4730 0.3922 0.041 Uiso 1 1 calc R U . . .
N2 N 0.5545(6) 0.8201(13) 0.3741(4) 0.034(2) Uani 1 1 d . U . . .
N4 N 1.1112(5) 1.0844(14) 0.5689(4) 0.031(2) Uani 1 1 d . U . . .
H4 H 1.0891 0.9683 0.5674 0.037 Uiso 1 1 calc R U . . .
N5 N 1.2066(5) 1.3262(13) 0.5885(4) 0.030(2) Uani 1 1 d . U . . .
O1 O 0.8087(5) 0.5861(11) 0.4481(3) 0.0320(14) Uani 1 1 d . U . . .
O2 O 0.7927(4) 0.8787(10) 0.4739(3) 0.0267(13) Uani 1 1 d . U . . .
O3 O 0.6896(5) 1.2060(11) 0.4168(4) 0.039(2) Uani 1 1 d . . . . .
O4 O 0.5452(5) 1.1812(11) 0.4301(4) 0.043(3) Uani 1 1 d . . . . .
O5 O 0.9479(4) 1.0860(10) 0.5167(4) 0.033(2) Uani 1 1 d . . . . .
O6 O 0.9662(5) 1.3893(11) 0.4892(4) 0.0409(19) Uani 1 1 d . U . . .
O7 O 1.0688(5) 1.7157(12) 0.5472(4) 0.040(2) Uani 1 1 d . . . . .
O8 O 1.2154(5) 1.6820(12) 0.5338(4) 0.041(3) Uani 1 1 d . . . . .
O1W O 0.8821(5) 1.621(2) 0.5738(4) 0.083(4) Uani 1 1 d . . . . .
H1WA H 0.8831 1.6408 0.6070 0.099 Uiso 1 1 d R U . . .
H1WB H 0.8871 1.4987 0.5686 0.099 Uiso 1 1 d R U . . .
O2W O 0.8759(6) 1.1346(17) 0.3892(5) 0.072(4) Uani 1 1 d . . . . .
H2WA H 0.9153 1.0939 0.3677 0.086 Uiso 1 1 d R U . . .
H2WB H 0.8271 1.1446 0.3723 0.086 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
C1 O2 1.216(13) . ?
C1 O1 1.222(13) . ?
C1 C2 1.455(15) . ?
C1 Ca2 2.879(11) 1_545 ?
C2 C3 1.356(13) . ?
C2 N1 1.400(14) . ?
C3 N2 1.433(14) . ?
C3 C4 1.511(10) . ?
C4 O4 1.228(12) . ?
C4 O3 1.229(12) . ?
C5 N2 1.270(15) . ?
C5 N1 1.442(14) . ?
C5 C6 1.495(17) . ?
C6 C7 1.505(16) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.3900 . ?
C7 C10 1.3900 . ?
C8 C9 1.3900 . ?
C8 H8 0.9300 . ?
C9 N3 1.3900 . ?
C9 H9 0.9300 . ?
N3 C11 1.3900 . ?
C11 C10 1.3900 . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C12 O5 1.235(12) . ?
C12 O6 1.241(13) . ?
C12 C13 1.520(11) . ?
C13 N4 1.399(13) . ?
C13 C14 1.440(13) . ?
C14 N5 1.388(14) . ?
C14 C15 1.397(15) . ?
C15 O8 1.278(12) . ?
C15 O7 1.306(12) . ?
C16 N5 1.331(15) . ?
C16 N4 1.344(15) . ?
C16 C17 1.49(2) . ?
C17 C18 1.50(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.3900 . ?
C18 C21 1.3900 . ?
C19 C20 1.3900 . ?
C19 H19 0.9300 . ?
C20 N6 1.3900 . ?
C20 H20 0.9300 . ?
N6 C22 1.3900 . ?
C22 C21 1.3900 . ?
C22 H22 0.9300 . ?
C21 H21 0.9300 . ?
Ca1 O2W 2.284(11) . ?
Ca1 O8 2.329(9) 3_485 ?
Ca1 O3 2.332(8) . ?
Ca1 O1 2.434(8) 1_565 ?
Ca1 O2 2.486(7) . ?
Ca1 O6 2.506(8) . ?
Ca1 O5 2.524(8) . ?
Ca1 Ca2 3.942(3) 1_545 ?
Ca1 H2WB 2.5046 . ?
Ca2 O4 2.316(9) 3_585 ?
Ca2 O7 2.327(8) . ?
Ca2 O1W 2.331(11) . ?
Ca2 O6 2.411(8) . ?
Ca2 O5 2.442(7) 1_565 ?
Ca2 O2 2.489(7) 1_565 ?
Ca2 O1 2.537(8) 1_565 ?
Ca2 C1 2.879(11) 1_565 ?
Ca2 Ca1 3.942(3) 1_565 ?
Ca2 H1WB 2.6138 . ?
N1 H1 0.8600 . ?
N4 H4 0.8600 . ?
O1 Ca1 2.434(8) 1_545 ?
O1 Ca2 2.537(8) 1_545 ?
O2 Ca2 2.489(7) 1_545 ?
O4 Ca2 2.316(9) 3_485 ?
O5 Ca2 2.442(7) 1_545 ?
O8 Ca1 2.329(9) 3_585 ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8501 . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8499 . ?

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 C1 O1 120.4(10) . . ?
O2 C1 C2 119.4(9) . . ?
O1 C1 C2 120.2(10) . . ?
O2 C1 Ca2 59.3(5) . 1_545 ?
O1 C1 Ca2 61.6(6) . 1_545 ?
C2 C1 Ca2 169.5(8) . 1_545 ?
C3 C2 N1 106.7(9) . . ?
C3 C2 C1 137.1(10) . . ?
N1 C2 C1 116.2(9) . . ?
C2 C3 N2 109.9(8) . . ?
C2 C3 C4 133.5(10) . . ?
N2 C3 C4 116.6(8) . . ?
O4 C4 O3 126.7(8) . . ?
O4 C4 C3 117.6(9) . . ?
O3 C4 C3 115.6(9) . . ?
N2 C5 N1 111.5(10) . . ?
N2 C5 C6 124.8(10) . . ?
N1 C5 C6 123.7(10) . . ?
C5 C6 C7 112.6(10) . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C10 120.0 . . ?
C8 C7 C6 116.8(6) . . ?
C10 C7 C6 123.1(6) . . ?
C9 C8 C7 120.0 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 N3 120.0 . . ?
C8 C9 H9 120.0 . . ?
N3 C9 H9 120.0 . . ?
C11 N3 C9 120.0 . . ?
C10 C11 N3 120.0 . . ?
C10 C11 H11 120.0 . . ?
N3 C11 H11 120.0 . . ?
C11 C10 C7 120.0 . . ?
C11 C10 H10 120.0 . . ?
C7 C10 H10 120.0 . . ?
O5 C12 O6 125.4(9) . . ?
O5 C12 C13 116.7(9) . . ?
O6 C12 C13 117.8(9) . . ?
N4 C13 C14 105.1(8) . . ?
N4 C13 C12 119.8(8) . . ?
C14 C13 C12 135.0(9) . . ?
N5 C14 C15 120.1(9) . . ?
N5 C14 C13 108.2(9) . . ?
C15 C14 C13 131.7(10) . . ?
O8 C15 O7 119.8(9) . . ?
O8 C15 C14 117.9(9) . . ?
O7 C15 C14 122.2(9) . . ?
N5 C16 N4 113.6(11) . . ?
N5 C16 C17 125.0(12) . . ?
N4 C16 C17 121.3(12) . . ?
C16 C17 C18 116.3(13) . . ?
C16 C17 H17A 108.2 . . ?
C18 C17 H17A 108.2 . . ?
C16 C17 H17B 108.2 . . ?
C18 C17 H17B 108.2 . . ?
H17A C17 H17B 107.4 . . ?
C19 C18 C21 120.0 . . ?
C19 C18 C17 117.8(8) . . ?
C21 C18 C17 122.1(9) . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
N6 C20 C19 120.0 . . ?
N6 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 N6 C22 120.0 . . ?
N6 C22 C21 120.0 . . ?
N6 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C21 C18 120.0 . . ?
C22 C21 H21 120.0 . . ?
C18 C21 H21 120.0 . . ?
O2W Ca1 O8 160.9(3) . 3_485 ?
O2W Ca1 O3 78.4(3) . . ?
O8 Ca1 O3 82.6(3) 3_485 . ?
O2W Ca1 O1 98.2(4) . 1_565 ?
O8 Ca1 O1 83.1(3) 3_485 1_565 ?
O3 Ca1 O1 85.9(3) . 1_565 ?
O2W Ca1 O2 78.8(3) . . ?
O8 Ca1 O2 95.0(3) 3_485 . ?
O3 Ca1 O2 79.3(3) . . ?
O1 Ca1 O2 165.2(3) 1_565 . ?
O2W Ca1 O6 88.7(3) . . ?
O8 Ca1 O6 109.7(3) 3_485 . ?
O3 Ca1 O6 152.7(3) . . ?
O1 Ca1 O6 72.1(3) 1_565 . ?
O2 Ca1 O6 122.0(2) . . ?
O2W Ca1 O5 90.3(3) . . ?
O8 Ca1 O5 105.1(3) 3_485 . ?
O3 Ca1 O5 150.3(3) . . ?
O1 Ca1 O5 123.2(3) 1_565 . ?
O2 Ca1 O5 71.6(2) . . ?
O6 Ca1 O5 51.9(2) . . ?
O2W Ca1 Ca2 72.7(3) . 1_545 ?
O8 Ca1 Ca2 113.1(2) 3_485 1_545 ?
O3 Ca1 Ca2 113.7(2) . 1_545 ?
O1 Ca1 Ca2 155.25(19) 1_565 1_545 ?
O2 Ca1 Ca2 37.61(15) . 1_545 ?
O6 Ca1 Ca2 84.50(19) . 1_545 ?
O5 Ca1 Ca2 36.74(17) . 1_545 ?
O2W Ca1 H2WB 19.8 . . ?
O8 Ca1 H2WB 141.6 3_485 . ?
O3 Ca1 H2WB 58.9 . . ?
O1 Ca1 H2WB 92.9 1_565 . ?
O2 Ca1 H2WB 79.3 . . ?
O6 Ca1 H2WB 105.2 . . ?
O5 Ca1 H2WB 108.9 . . ?
Ca2 Ca1 H2WB 85.3 1_545 . ?
O4 Ca2 O7 82.5(3) 3_585 . ?
O4 Ca2 O1W 160.4(3) 3_585 . ?
O7 Ca2 O1W 78.6(3) . . ?
O4 Ca2 O6 95.4(3) 3_585 . ?
O7 Ca2 O6 81.0(3) . . ?
O1W Ca2 O6 76.7(4) . . ?
O4 Ca2 O5 84.5(3) 3_585 1_565 ?
O7 Ca2 O5 84.4(3) . 1_565 ?
O1W Ca2 O5 98.7(4) . 1_565 ?
O6 Ca2 O5 165.3(3) . 1_565 ?
O4 Ca2 O2 111.2(3) 3_585 1_565 ?
O7 Ca2 O2 151.6(3) . 1_565 ?
O1W Ca2 O2 88.1(3) . 1_565 ?
O6 Ca2 O2 120.4(3) . 1_565 ?
O5 Ca2 O2 72.9(2) 1_565 1_565 ?
O4 Ca2 O1 107.4(3) 3_585 1_565 ?
O7 Ca2 O1 151.8(3) . 1_565 ?
O1W Ca2 O1 87.5(3) . 1_565 ?
O6 Ca2 O1 72.0(3) . 1_565 ?
O5 Ca2 O1 122.2(3) 1_565 1_565 ?
O2 Ca2 O1 49.8(2) 1_565 1_565 ?
O4 Ca2 C1 109.3(3) 3_585 1_565 ?
O7 Ca2 C1 168.1(3) . 1_565 ?
O1W Ca2 C1 89.6(3) . 1_565 ?
O6 Ca2 C1 96.8(3) . 1_565 ?
O5 Ca2 C1 97.2(3) 1_565 1_565 ?
O2 Ca2 C1 24.9(3) 1_565 1_565 ?
O1 Ca2 C1 25.1(3) 1_565 1_565 ?
O4 Ca2 Ca1 89.4(2) 3_585 1_565 ?
O7 Ca2 Ca1 122.6(2) . 1_565 ?
O1W Ca2 Ca1 105.1(3) . 1_565 ?
O6 Ca2 Ca1 156.4(2) . 1_565 ?
O5 Ca2 Ca1 38.19(18) 1_565 1_565 ?
O2 Ca2 Ca1 37.56(16) 1_565 1_565 ?
O1 Ca2 Ca1 84.54(18) 1_565 1_565 ?
C1 Ca2 Ca1 60.0(2) 1_565 1_565 ?
O4 Ca2 H1WB 149.6 3_585 . ?
O7 Ca2 H1WB 78.9 . . ?
O1W Ca2 H1WB 18.7 . . ?
O6 Ca2 H1WB 58.1 . . ?
O5 Ca2 H1WB 117.1 1_565 . ?
O2 Ca2 H1WB 96.3 1_565 . ?
O1 Ca2 H1WB 80.2 1_565 . ?
C1 Ca2 H1WB 90.0 1_565 . ?
Ca1 Ca2 H1WB 121.0 1_565 . ?
C2 N1 C5 105.1(9) . . ?
C2 N1 H1 127.4 . . ?
C5 N1 H1 127.4 . . ?
C5 N2 C3 106.6(9) . . ?
C16 N4 C13 107.1(9) . . ?
C16 N4 H4 126.5 . . ?
C13 N4 H4 126.5 . . ?
C16 N5 C14 106.0(9) . . ?
C1 O1 Ca1 149.1(7) . 1_545 ?
C1 O1 Ca2 93.3(6) . 1_545 ?
Ca1 O1 Ca2 104.9(3) 1_545 1_545 ?
C1 O2 Ca1 142.8(8) . . ?
C1 O2 Ca2 95.8(6) . 1_545 ?
Ca1 O2 Ca2 104.8(2) . 1_545 ?
C4 O3 Ca1 136.9(8) . . ?
C4 O4 Ca2 148.1(9) . 3_485 ?
C12 O5 Ca2 147.9(7) . 1_545 ?
C12 O5 Ca1 90.8(6) . . ?
Ca2 O5 Ca1 105.1(3) 1_545 . ?
C12 O6 Ca2 144.5(8) . . ?
C12 O6 Ca1 91.4(6) . . ?
Ca2 O6 Ca1 106.5(3) . . ?
C15 O7 Ca2 133.2(8) . . ?
C15 O8 Ca1 147.4(8) . 3_585 ?
Ca2 O1W H1WA 141.9 . . ?
Ca2 O1W H1WB 99.8 . . ?
H1WA O1W H1WB 107.7 . . ?
Ca1 O2W H2WA 157.3 . . ?
Ca1 O2W H2WB 95.0 . . ?
H2WA O2W H2WB 107.7 . . ?

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
O2 C1 C2 C3 2(2) . . . . ?
O1 C1 C2 C3 -174.8(13) . . . . ?
Ca2 C1 C2 C3 -78(5) 1_545 . . . ?
O2 C1 C2 N1 -175.6(10) . . . . ?
O1 C1 C2 N1 7.6(16) . . . . ?
Ca2 C1 C2 N1 104(4) 1_545 . . . ?
N1 C2 C3 N2 0.9(13) . . . . ?
C1 C2 C3 N2 -176.9(13) . . . . ?
N1 C2 C3 C4 -178.9(12) . . . . ?
C1 C2 C3 C4 3(2) . . . . ?
C2 C3 C4 O4 -140.2(14) . . . . ?
N2 C3 C4 O4 40.0(15) . . . . ?
C2 C3 C4 O3 41.3(19) . . . . ?
N2 C3 C4 O3 -138.5(11) . . . . ?
N2 C5 C6 C7 80.5(15) . . . . ?
N1 C5 C6 C7 -97.2(13) . . . . ?
C5 C6 C7 C8 111.3(9) . . . . ?
C5 C6 C7 C10 -71.3(11) . . . . ?
C10 C7 C8 C9 0.0 . . . . ?
C6 C7 C8 C9 177.5(7) . . . . ?
C7 C8 C9 N3 0.0 . . . . ?
C8 C9 N3 C11 0.0 . . . . ?
C9 N3 C11 C10 0.0 . . . . ?
N3 C11 C10 C7 0.0 . . . . ?
C8 C7 C10 C11 0.0 . . . . ?
C6 C7 C10 C11 -177.3(7) . . . . ?
O5 C12 C13 N4 10.9(14) . . . . ?
O6 C12 C13 N4 -170.6(9) . . . . ?
O5 C12 C13 C14 -173.4(11) . . . . ?
O6 C12 C13 C14 5.1(17) . . . . ?
N4 C13 C14 N5 -1.5(12) . . . . ?
C12 C13 C14 N5 -177.6(11) . . . . ?
N4 C13 C14 C15 177.7(12) . . . . ?
C12 C13 C14 C15 2(2) . . . . ?
N5 C14 C15 O8 38.0(17) . . . . ?
C13 C14 C15 O8 -141.1(12) . . . . ?
N5 C14 C15 O7 -138.1(12) . . . . ?
C13 C14 C15 O7 42.8(19) . . . . ?
N5 C16 C17 C18 76.9(18) . . . . ?
N4 C16 C17 C18 -99.6(16) . . . . ?
C16 C17 C18 C19 70.8(14) . . . . ?
C16 C17 C18 C21 -113.9(12) . . . . ?
C21 C18 C19 C20 0.0 . . . . ?
C17 C18 C19 C20 175.4(9) . . . . ?
C18 C19 C20 N6 0.0 . . . . ?
C19 C20 N6 C22 0.0 . . . . ?
C20 N6 C22 C21 0.0 . . . . ?
N6 C22 C21 C18 0.0 . . . . ?
C19 C18 C21 C22 0.0 . . . . ?
C17 C18 C21 C22 -175.2(10) . . . . ?
C3 C2 N1 C5 -3.2(12) . . . . ?
C1 C2 N1 C5 175.1(10) . . . . ?
N2 C5 N1 C2 4.8(14) . . . . ?
C6 C5 N1 C2 -177.2(11) . . . . ?
N1 C5 N2 C3 -4.2(14) . . . . ?
C6 C5 N2 C3 177.9(11) . . . . ?
C2 C3 N2 C5 2.1(14) . . . . ?
C4 C3 N2 C5 -178.1(10) . . . . ?
N5 C16 N4 C13 -1.7(14) . . . . ?
C17 C16 N4 C13 175.2(12) . . . . ?
C14 C13 N4 C16 1.8(12) . . . . ?
C12 C13 N4 C16 178.6(10) . . . . ?
N4 C16 N5 C14 0.7(15) . . . . ?
C17 C16 N5 C14 -176.0(13) . . . . ?
C15 C14 N5 C16 -178.8(11) . . . . ?
C13 C14 N5 C16 0.5(13) . . . . ?
O2 C1 O1 Ca1 118.0(13) . . . 1_545 ?
C2 C1 O1 Ca1 -65(2) . . . 1_545 ?
Ca2 C1 O1 Ca1 126.7(15) 1_545 . . 1_545 ?
O2 C1 O1 Ca2 -8.7(11) . . . 1_545 ?
C2 C1 O1 Ca2 168.1(9) . . . 1_545 ?
O1 C1 O2 Ca1 133.0(10) . . . . ?
C2 C1 O2 Ca1 -43.9(17) . . . . ?
Ca2 C1 O2 Ca1 124.1(10) 1_545 . . . ?
O1 C1 O2 Ca2 8.9(12) . . . 1_545 ?
C2 C1 O2 Ca2 -168.0(9) . . . 1_545 ?
O4 C4 O3 Ca1 105.8(13) . . . . ?
C3 C4 O3 Ca1 -75.9(14) . . . . ?
O3 C4 O4 Ca2 -87.5(17) . . . 3_485 ?
C3 C4 O4 Ca2 94.2(15) . . . 3_485 ?
O6 C12 O5 Ca2 113.2(13) . . . 1_545 ?
C13 C12 O5 Ca2 -68.5(17) . . . 1_545 ?
O6 C12 O5 Ca1 -7.5(11) . . . . ?
C13 C12 O5 Ca1 170.9(8) . . . . ?
O5 C12 O6 Ca2 129.2(11) . . . . ?
C13 C12 O6 Ca2 -49.2(15) . . . . ?
O5 C12 O6 Ca1 7.5(11) . . . . ?
C13 C12 O6 Ca1 -170.8(8) . . . . ?
O8 C15 O7 Ca2 111.0(11) . . . . ?
C14 C15 O7 Ca2 -73.0(15) . . . . ?
O7 C15 O8 Ca1 -91.7(16) . . . 3_585 ?
C14 C15 O8 Ca1 92.1(16) . . . 3_585 ?

_refine_diff_density_max         1.349
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.188

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1539790'
_audit_update_record             
;
2017-03-23 deposited with the CCDC.
2017-05-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H9 Ba N3 O5'
_chemical_formula_sum            'C11 H9 Ba N3 O5'
_chemical_formula_weight         400.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ba Ba -0.3244 2.2819 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   13.996(3)
_cell_length_b                   7.1157(18)
_cell_length_c                   13.539(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.205(4)
_cell_angle_gamma                90
_cell_volume                     1248.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1999
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      25.94

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.131
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    3.205
_shelx_estimated_absorpt_T_min   0.467
_shelx_estimated_absorpt_T_max   0.539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4672
_exptl_absorpt_correction_T_max  0.5390
_exptl_absorpt_process_details   'SADABS(sheldrick, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6537
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.571
_diffrn_reflns_theta_max         25.989
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2429
_reflns_number_gt                1978
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0464P)²+0.0500P] 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_number_reflns         2429
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
Ba1 Ba 0.45967(2) 0.46468(4) 0.31925(2) 0.02352(13) Uani 1 1 d . . . . .
C1 C 0.3839(4) 0.2843(6) 0.0307(4) 0.0239(10) Uani 1 1 d . . . . .
C2 C 0.3418(4) 0.4674(6) -0.0218(4) 0.0234(10) Uani 1 1 d . . . . .
C3 C 0.3459(3) 0.5768(6) -0.1046(4) 0.0221(10) Uani 1 1 d . . . . .
C4 C 0.4000(4) 0.5490(6) -0.1794(4) 0.0222(10) Uani 1 1 d . . . . .
C5 C 0.2627(4) 0.7398(7) -0.0285(4) 0.0273(11) Uani 1 1 d . . . . .
C6 C 0.2046(4) 0.8882(8) 0.0026(5) 0.0349(13) Uani 1 1 d . . . . .
H6A H 0.2369 1.0087 0.0025 0.042 Uiso 1 1 calc R U . . .
H6B H 0.2095 0.8640 0.0749 0.042 Uiso 1 1 calc R U . . .
C7 C 0.0928(4) 0.9004(8) -0.0690(4) 0.0330(12) Uani 1 1 d . . . . .
C8 C 0.0492(6) 1.0622(9) -0.1211(6) 0.0555(18) Uani 1 1 d . . . . .
H8 H 0.0894 1.1692 -0.1140 0.067 Uiso 1 1 calc R U . . .
C9 C -0.0555(6) 1.0663(14) -0.1849(6) 0.075(3) Uani 1 1 d . . . . .
H9 H -0.0868 1.1752 -0.2204 0.090 Uiso 1 1 calc R U . . .
C10 C -0.1103(6) 0.9049(17) -0.1934(6) 0.080(3) Uani 1 1 d . . . . .
H10 H -0.1800 0.9067 -0.2370 0.096 Uiso 1 1 calc R U . . .
C11 C 0.0280(4) 0.7508(8) -0.0836(5) 0.0461(16) Uani 1 1 d . . . . .
H11 H 0.0563 0.6405 -0.0475 0.055 Uiso 1 1 calc R U . . .
N1 N 0.2956(3) 0.7466(5) -0.1079(3) 0.0276(10) Uani 1 1 d . . . . .
N2 N 0.2874(3) 0.5750(6) 0.0241(3) 0.0270(10) Uani 1 1 d . . . . .
H2 H 0.2718 0.5422 0.0773 0.032 Uiso 1 1 calc R U . . .
N3 N -0.0721(4) 0.7486(10) -0.1449(5) 0.0662(18) Uani 1 1 d . . . . .
O1 O 0.3799(3) 0.2610(5) 0.1211(3) 0.0316(8) Uani 1 1 d . . . . .
O2 O 0.4208(3) 0.1667(5) -0.0127(3) 0.0359(9) Uani 1 1 d . . . . .
O3 O 0.4569(2) 0.4084(5) -0.1680(3) 0.0275(8) Uani 1 1 d . . . . .
O4 O 0.3894(3) 0.6747(5) -0.2483(3) 0.0305(8) Uani 1 1 d . . . . .
O1W O 0.2381(3) 0.5087(5) 0.2097(4) 0.0473(11) Uani 1 1 d . . . . .
H1WA H 0.2313 0.5808 0.2567 0.057 Uiso 1 1 d R U . . .
H1WB H 0.1884 0.4307 0.1912 0.057 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
Ba1 O3 2.662(4) 4_566 ?
Ba1 O2 2.699(3) 4_566 ?
Ba1 O4 2.776(3) 4_576 ?
Ba1 O4 2.811(3) 3_665 ?
Ba1 O3 2.860(3) 3_665 ?
Ba1 O1 2.878(4) . ?
Ba1 O2 2.900(4) 2_655 ?
Ba1 O1W 2.905(4) . ?
Ba1 O1 2.961(3) 2_655 ?
Ba1 C4 3.204(5) 3_665 ?
Ba1 C1 3.276(5) 2_655 ?
C1 O2 1.241(6) . ?
C1 O1 1.257(6) . ?
C1 C2 1.495(6) . ?
C1 Ba1 3.276(5) 2_645 ?
C2 N2 1.381(6) . ?
C2 C3 1.384(7) . ?
C3 N1 1.390(6) . ?
C3 C4 1.489(6) . ?
C4 O3 1.252(6) . ?
C4 O4 1.261(6) . ?
C4 Ba1 3.204(5) 3_665 ?
C5 N1 1.321(6) . ?
C5 N2 1.348(6) . ?
C5 C6 1.488(7) . ?
C6 C7 1.499(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C11 1.364(7) . ?
C7 C8 1.368(8) . ?
C8 C9 1.391(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.361(13) . ?
C9 H9 0.9300 . ?
C10 N3 1.300(11) . ?
C10 H10 0.9300 . ?
C11 N3 1.332(8) . ?
C11 H11 0.9300 . ?
N2 H2 0.8600 . ?
O1 Ba1 2.961(3) 2_645 ?
O2 Ba1 2.699(3) 4_565 ?
O2 Ba1 2.900(4) 2_645 ?
O3 Ba1 2.662(4) 4_565 ?
O3 Ba1 2.860(3) 3_665 ?
O4 Ba1 2.776(3) 4_575 ?
O4 Ba1 2.811(3) 3_665 ?
O1W H1WA 0.8501 . ?
O1W H1WB 0.8500 . ?

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 Ba1 O2 65.63(10) 4_566 4_566 ?
O3 Ba1 O4 158.61(10) 4_566 4_576 ?
O2 Ba1 O4 116.03(10) 4_566 4_576 ?
O3 Ba1 O4 72.62(9) 4_566 3_665 ?
O2 Ba1 O4 125.63(10) 4_566 3_665 ?
O4 Ba1 O4 115.60(8) 4_576 3_665 ?
O3 Ba1 O3 112.41(9) 4_566 3_665 ?
O2 Ba1 O3 168.52(10) 4_566 3_665 ?
O4 Ba1 O3 70.24(10) 4_576 3_665 ?
O4 Ba1 O3 45.89(10) 3_665 3_665 ?
O3 Ba1 O1 63.13(10) 4_566 . ?
O2 Ba1 O1 118.75(10) 4_566 . ?
O4 Ba1 O1 101.18(10) 4_576 . ?
O4 Ba1 O1 65.20(10) 3_665 . ?
O3 Ba1 O1 67.10(10) 3_665 . ?
O3 Ba1 O2 116.96(10) 4_566 2_655 ?
O2 Ba1 O2 68.99(11) 4_566 2_655 ?
O4 Ba1 O2 81.44(10) 4_576 2_655 ?
O4 Ba1 O2 103.41(10) 3_665 2_655 ?
O3 Ba1 O2 103.76(10) 3_665 2_655 ?
O1 Ba1 O2 168.41(10) . 2_655 ?
O3 Ba1 O1W 95.85(10) 4_566 . ?
O2 Ba1 O1W 87.23(12) 4_566 . ?
O4 Ba1 O1W 63.57(10) 4_576 . ?
O4 Ba1 O1W 131.20(11) 3_665 . ?
O3 Ba1 O1W 104.25(11) 3_665 . ?
O1 Ba1 O1W 67.36(11) . . ?
O2 Ba1 O1W 123.21(11) 2_655 . ?
O3 Ba1 O1 136.11(10) 4_566 2_655 ?
O2 Ba1 O1 112.96(10) 4_566 2_655 ?
O4 Ba1 O1 64.51(10) 4_576 2_655 ?
O4 Ba1 O1 75.78(10) 3_665 2_655 ?
O3 Ba1 O1 59.86(10) 3_665 2_655 ?
O1 Ba1 O1 126.87(6) . 2_655 ?
O2 Ba1 O1 44.08(9) 2_655 2_655 ?
O1W Ba1 O1 127.99(10) . 2_655 ?
O3 Ba1 C4 92.01(10) 4_566 3_665 ?
O2 Ba1 C4 148.40(12) 4_566 3_665 ?
O4 Ba1 C4 93.06(11) 4_576 3_665 ?
O4 Ba1 C4 23.02(10) 3_665 3_665 ?
O3 Ba1 C4 22.93(11) 3_665 3_665 ?
O1 Ba1 C4 62.74(11) . 3_665 ?
O2 Ba1 C4 106.01(11) 2_655 3_665 ?
O1W Ba1 C4 118.42(12) . 3_665 ?
O1 Ba1 C4 67.18(11) 2_655 3_665 ?
O3 Ba1 C1 132.45(11) 4_566 2_655 ?
O2 Ba1 C1 91.02(12) 4_566 2_655 ?
O4 Ba1 C1 68.49(11) 4_576 2_655 ?
O4 Ba1 C1 92.55(11) 3_665 2_655 ?
O3 Ba1 C1 82.35(11) 3_665 2_655 ?
O1 Ba1 C1 149.40(10) . 2_655 ?
O2 Ba1 C1 22.13(10) 2_655 2_655 ?
O1W Ba1 C1 125.17(11) . 2_655 ?
O1 Ba1 C1 22.53(10) 2_655 2_655 ?
C4 Ba1 C1 88.43(12) 3_665 2_655 ?
O3 Ba1 Ba1 148.58(7) 4_566 2_655 ?
O2 Ba1 Ba1 144.28(7) 4_566 2_655 ?
O4 Ba1 Ba1 38.93(7) 4_576 2_655 ?
O4 Ba1 Ba1 77.94(7) 3_665 2_655 ?
O3 Ba1 Ba1 36.20(7) 3_665 2_655 ?
O1 Ba1 Ba1 94.71(7) . 2_655 ?
O2 Ba1 Ba1 80.18(7) 2_655 2_655 ?
O1W Ba1 Ba1 95.28(8) . 2_655 ?
O1 Ba1 Ba1 40.91(7) 2_655 2_655 ?
C4 Ba1 Ba1 56.98(8) 3_665 2_655 ?
C1 Ba1 Ba1 58.66(9) 2_655 2_655 ?
O2 C1 O1 123.4(5) . . ?
O2 C1 C2 121.6(4) . . ?
O1 C1 C2 115.0(4) . . ?
O2 C1 Ba1 61.7(3) . 2_645 ?
O1 C1 Ba1 64.5(3) . 2_645 ?
C2 C1 Ba1 162.0(3) . 2_645 ?
N2 C2 C3 104.6(4) . . ?
N2 C2 C1 117.1(4) . . ?
C3 C2 C1 138.2(4) . . ?
C2 C3 N1 109.8(4) . . ?
C2 C3 C4 131.6(4) . . ?
N1 C3 C4 118.3(4) . . ?
O3 C4 O4 123.4(4) . . ?
O3 C4 C3 119.1(4) . . ?
O4 C4 C3 117.5(4) . . ?
O3 C4 Ba1 62.9(2) . 3_665 ?
O4 C4 Ba1 60.7(2) . 3_665 ?
C3 C4 Ba1 171.5(3) . 3_665 ?
N1 C5 N2 111.3(4) . . ?
N1 C5 C6 126.9(5) . . ?
N2 C5 C6 121.8(5) . . ?
C5 C6 C7 114.0(4) . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.6 . . ?
C11 C7 C8 116.1(6) . . ?
C11 C7 C6 121.5(5) . . ?
C8 C7 C6 122.4(6) . . ?
C7 C8 C9 119.9(7) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 117.5(7) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
N3 C10 C9 124.6(7) . . ?
N3 C10 H10 117.7 . . ?
C9 C10 H10 117.7 . . ?
N3 C11 C7 125.8(6) . . ?
N3 C11 H11 117.1 . . ?
C7 C11 H11 117.1 . . ?
C5 N1 C3 105.6(4) . . ?
C5 N2 C2 108.6(4) . . ?
C5 N2 H2 125.7 . . ?
C2 N2 H2 125.7 . . ?
C10 N3 C11 116.1(7) . . ?
C1 O1 Ba1 134.2(3) . . ?
C1 O1 Ba1 93.0(3) . 2_645 ?
Ba1 O1 Ba1 96.73(10) . 2_645 ?
C1 O2 Ba1 152.2(3) . 4_565 ?
C1 O2 Ba1 96.2(3) . 2_645 ?
Ba1 O2 Ba1 111.01(11) 4_565 2_645 ?
C4 O3 Ba1 144.5(3) . 4_565 ?
C4 O3 Ba1 94.2(3) . 3_665 ?
Ba1 O3 Ba1 104.40(10) 4_565 3_665 ?
C4 O4 Ba1 118.9(3) . 4_575 ?
C4 O4 Ba1 96.3(3) . 3_665 ?
Ba1 O4 Ba1 102.72(11) 4_575 3_665 ?
Ba1 O1W H1WA 94.7 . . ?
Ba1 O1W H1WB 132.5 . . ?
H1WA O1W H1WB 107.7 . . ?

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
O2 C1 C2 N2 169.7(4) . . . . ?
O1 C1 C2 N2 -11.1(6) . . . . ?
Ba1 C1 C2 N2 -95.3(11) 2_645 . . . ?
O2 C1 C2 C3 -15.9(9) . . . . ?
O1 C1 C2 C3 163.3(6) . . . . ?
Ba1 C1 C2 C3 79.2(13) 2_645 . . . ?
N2 C2 C3 N1 0.4(5) . . . . ?
C1 C2 C3 N1 -174.5(5) . . . . ?
N2 C2 C3 C4 174.6(5) . . . . ?
C1 C2 C3 C4 -0.3(10) . . . . ?
C2 C3 C4 O3 -3.3(8) . . . . ?
N1 C3 C4 O3 170.5(4) . . . . ?
C2 C3 C4 O4 179.9(5) . . . . ?
N1 C3 C4 O4 -6.3(7) . . . . ?
N1 C5 C6 C7 76.3(7) . . . . ?
N2 C5 C6 C7 -103.0(6) . . . . ?
C5 C6 C7 C11 58.8(7) . . . . ?
C5 C6 C7 C8 -122.9(6) . . . . ?
C11 C7 C8 C9 -0.4(9) . . . . ?
C6 C7 C8 C9 -178.7(6) . . . . ?
C7 C8 C9 C10 -0.7(11) . . . . ?
C8 C9 C10 N3 1.1(12) . . . . ?
C8 C7 C11 N3 1.3(9) . . . . ?
C6 C7 C11 N3 179.6(6) . . . . ?
N2 C5 N1 C3 -1.0(5) . . . . ?
C6 C5 N1 C3 179.6(5) . . . . ?
C2 C3 N1 C5 0.4(5) . . . . ?
C4 C3 N1 C5 -174.7(4) . . . . ?
N1 C5 N2 C2 1.3(6) . . . . ?
C6 C5 N2 C2 -179.3(4) . . . . ?
C3 C2 N2 C5 -1.0(5) . . . . ?
C1 C2 N2 C5 175.2(4) . . . . ?
C9 C10 N3 C11 -0.3(12) . . . . ?
C7 C11 N3 C10 -0.9(10) . . . . ?
O2 C1 O1 Ba1 121.4(5) . . . . ?
C2 C1 O1 Ba1 -57.8(6) . . . . ?
Ba1 C1 O1 Ba1 102.3(4) 2_645 . . . ?
O2 C1 O1 Ba1 19.1(5) . . . 2_645 ?
C2 C1 O1 Ba1 -160.1(3) . . . 2_645 ?
O1 C1 O2 Ba1 171.8(4) . . . 4_565 ?
C2 C1 O2 Ba1 -9.0(10) . . . 4_565 ?
Ba1 C1 O2 Ba1 -168.6(7) 2_645 . . 4_565 ?
O1 C1 O2 Ba1 -19.6(5) . . . 2_645 ?
C2 C1 O2 Ba1 159.6(4) . . . 2_645 ?
O4 C4 O3 Ba1 -116.0(5) . . . 4_565 ?
C3 C4 O3 Ba1 67.4(7) . . . 4_565 ?
Ba1 C4 O3 Ba1 -122.1(5) 3_665 . . 4_565 ?
O4 C4 O3 Ba1 6.1(5) . . . 3_665 ?
C3 C4 O3 Ba1 -170.6(4) . . . 3_665 ?
O3 C4 O4 Ba1 -114.5(4) . . . 4_575 ?
C3 C4 O4 Ba1 62.2(5) . . . 4_575 ?
Ba1 C4 O4 Ba1 -108.3(2) 3_665 . . 4_575 ?
O3 C4 O4 Ba1 -6.2(5) . . . 3_665 ?
C3 C4 O4 Ba1 170.5(4) . . . 3_665 ?

_refine_diff_density_max         0.883
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.147

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1539787'
_audit_update_record             
;
2017-03-23 deposited with the CCDC.
2017-05-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H9 N3 O5 Sr'
_chemical_formula_sum            'C11 H9 N3 O5 Sr'
_chemical_formula_weight         350.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sr Sr -1.5307 3.2498 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.696(6)
_cell_length_b                   6.854(3)
_cell_length_c                   13.000(6)
_cell_angle_alpha                90
_cell_angle_beta                 112.606(7)
_cell_angle_gamma                90
_cell_volume                     1208.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1788
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      25.60

_exptl_crystal_description       Plate-like
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.928
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    4.485
_shelx_estimated_absorpt_T_min   0.346
_shelx_estimated_absorpt_T_max   0.400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3464
_exptl_absorpt_correction_T_max  0.4002
_exptl_absorpt_process_details   'SADABS(sheldrick, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6223
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.003
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2355
_reflns_number_gt                1815
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0380P)²] 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_number_reflns         2355
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9051(3) 0.5604(6) 0.5949(3) 0.0214(9) Uani 1 1 d . . . . .
C2 C 0.8433(3) 0.5717(6) 0.4729(3) 0.0221(9) Uani 1 1 d . . . . .
C3 C 0.8410(3) 0.4529(6) 0.3847(3) 0.0220(9) Uani 1 1 d . . . . .
C4 C 0.8876(3) 0.2649(6) 0.3702(3) 0.0219(9) Uani 1 1 d . . . . .
C5 C 0.7575(3) 0.7285(6) 0.3204(3) 0.0263(10) Uani 1 1 d . . . . .
C6 C 0.7030(3) 0.8872(7) 0.2404(4) 0.0353(11) Uani 1 1 d . . . . .
H6A H 0.7349 0.9083 0.1884 0.042 Uiso 1 1 calc R U . . .
H6B H 0.7086 1.0072 0.2819 0.042 Uiso 1 1 calc R U . . .
C7 C 0.5952(3) 0.8458(7) 0.1751(4) 0.0345(11) Uani 1 1 d . . . . .
C8 C 0.5618(4) 0.7722(7) 0.0675(4) 0.0473(13) Uani 1 1 d . . . . .
H8 H 0.6060 0.7453 0.0339 0.057 Uiso 1 1 calc R U . . .
C9 C 0.4627(5) 0.7394(8) 0.0111(5) 0.0592(16) Uani 1 1 d . . . . .
H9 H 0.4425 0.6851 -0.0598 0.071 Uiso 1 1 calc R U . . .
C10 C 0.5245(4) 0.8892(8) 0.2172(5) 0.0493(14) Uani 1 1 d . . . . .
H10 H 0.5430 0.9416 0.2884 0.059 Uiso 1 1 calc R U . . .
C11 C 0.4253(4) 0.8544(9) 0.1528(5) 0.0585(16) Uani 1 1 d . . . . .
H11 H 0.3791 0.8851 0.1830 0.070 Uiso 1 1 calc R U . . .
N1 N 0.7894(3) 0.7413(5) 0.4308(3) 0.0265(8) Uani 1 1 d . . . . .
N2 N 0.7855(3) 0.5559(5) 0.2895(3) 0.0252(8) Uani 1 1 d . . . . .
H2 H 0.7711 0.5173 0.2222 0.030 Uiso 1 1 calc R U . . .
N3 N 0.3933(4) 0.7797(7) 0.0506(4) 0.0593(13) Uani 1 1 d . . . . .
O1 O 0.8976(2) 0.7003(4) 0.6563(2) 0.0261(7) Uani 1 1 d . . . . .
O2 O 0.9667(2) 0.4228(4) 0.6321(2) 0.0241(6) Uani 1 1 d . . . . .
O3 O 0.9278(2) 0.1506(4) 0.4503(2) 0.0331(7) Uani 1 1 d . . . . .
O4 O 0.8845(2) 0.2319(4) 0.2735(2) 0.0306(7) Uani 1 1 d . . . . .
O1W O 1.2277(2) 0.5392(4) 0.9319(2) 0.0311(7) Uani 1 1 d . . . . .
H1WA H 1.2420 0.4251 0.9589 0.037 Uiso 1 1 d R U . . .
H1WB H 1.2744 0.6147 0.9699 0.037 Uiso 1 1 d R U . . .
Sr1 Sr 1.03144(3) 0.55588(5) 0.84580(3) 0.02144(15) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.268(5) . ?
C1 O1 1.279(4) . ?
C1 C2 1.496(5) . ?
C2 N1 1.394(5) . ?
C2 C3 1.396(5) . ?
C3 N2 1.385(5) . ?
C3 C4 1.505(6) . ?
C4 O3 1.255(5) . ?
C4 O4 1.260(5) . ?
C4 Sr1 3.149(4) 4_565 ?
C5 N1 1.330(5) . ?
C5 N2 1.363(5) . ?
C5 C6 1.505(6) . ?
C6 C7 1.509(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C10 1.382(7) . ?
C7 C8 1.387(7) . ?
C8 C9 1.375(9) . ?
C8 H8 0.9300 . ?
C9 N3 1.336(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.394(8) . ?
C10 H10 0.9300 . ?
C11 N3 1.329(7) . ?
C11 H11 0.9300 . ?
N2 H2 0.8600 . ?
O1 Sr1 2.655(3) 2_756 ?
O1 Sr1 2.682(3) . ?
O2 Sr1 2.530(3) 2_746 ?
O2 Sr1 2.725(3) . ?
O3 Sr1 2.567(3) 2_746 ?
O3 Sr1 2.785(3) 4_565 ?
O4 Sr1 2.742(3) 3_766 ?
O4 Sr1 2.807(3) 4_565 ?
O1W Sr1 2.665(3) . ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8499 . ?
Sr1 O2 2.530(3) 2_756 ?
Sr1 O3 2.567(3) 2_756 ?
Sr1 O1 2.655(3) 2_746 ?
Sr1 O4 2.742(3) 3_766 ?
Sr1 O3 2.785(3) 4_566 ?
Sr1 O4 2.807(3) 4_566 ?
Sr1 C4 3.149(4) 4_566 ?
Sr1 Sr1 4.1270(14) 2_756 ?
Sr1 Sr1 4.1270(14) 2_746 ?

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 C1 O1 122.7(4) . . ?
O2 C1 C2 119.8(3) . . ?
O1 C1 C2 117.4(3) . . ?
N1 C2 C3 109.5(3) . . ?
N1 C2 C1 118.7(3) . . ?
C3 C2 C1 130.8(4) . . ?
N2 C3 C2 104.9(3) . . ?
N2 C3 C4 117.7(3) . . ?
C2 C3 C4 137.2(4) . . ?
O3 C4 O4 122.7(4) . . ?
O3 C4 C3 121.5(3) . . ?
O4 C4 C3 115.8(3) . . ?
O3 C4 Sr1 61.8(2) . 4_565 ?
O4 C4 Sr1 62.8(2) . 4_565 ?
C3 C4 Sr1 165.0(3) . 4_565 ?
N1 C5 N2 110.7(3) . . ?
N1 C5 C6 124.8(4) . . ?
N2 C5 C6 124.3(4) . . ?
C5 C6 C7 114.7(4) . . ?
C5 C6 H6A 108.6 . . ?
C7 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
C7 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C10 C7 C8 116.7(5) . . ?
C10 C7 C6 121.6(4) . . ?
C8 C7 C6 121.6(5) . . ?
C9 C8 C7 119.3(5) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
N3 C9 C8 124.8(5) . . ?
N3 C9 H9 117.6 . . ?
C8 C9 H9 117.6 . . ?
C7 C10 C11 119.8(5) . . ?
C7 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
N3 C11 C10 123.5(6) . . ?
N3 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
C5 N1 C2 106.2(3) . . ?
C5 N2 C3 108.7(3) . . ?
C5 N2 H2 125.7 . . ?
C3 N2 H2 125.7 . . ?
C11 N3 C9 115.8(5) . . ?
C1 O1 Sr1 123.6(2) . 2_756 ?
C1 O1 Sr1 95.1(2) . . ?
Sr1 O1 Sr1 101.31(9) 2_756 . ?
C1 O2 Sr1 139.3(3) . 2_746 ?
C1 O2 Sr1 93.3(2) . . ?
Sr1 O2 Sr1 103.46(9) 2_746 . ?
C4 O3 Sr1 149.7(2) . 2_746 ?
C4 O3 Sr1 94.8(2) . 4_565 ?
Sr1 O3 Sr1 114.90(11) 2_746 4_565 ?
C4 O4 Sr1 128.1(3) . 3_766 ?
C4 O4 Sr1 93.7(2) . 4_565 ?
Sr1 O4 Sr1 96.10(10) 3_766 4_565 ?
Sr1 O1W H1WA 105.5 . . ?
Sr1 O1W H1WB 136.0 . . ?
H1WA O1W H1WB 107.7 . . ?
O2 Sr1 O3 69.11(9) 2_756 2_756 ?
O2 Sr1 O1 157.88(9) 2_756 2_746 ?
O3 Sr1 O1 107.82(9) 2_756 2_746 ?
O2 Sr1 O1W 91.84(9) 2_756 . ?
O3 Sr1 O1W 78.00(10) 2_756 . ?
O1 Sr1 O1W 66.37(9) 2_746 . ?
O2 Sr1 O1 73.12(9) 2_756 . ?
O3 Sr1 O1 130.79(9) 2_756 . ?
O1 Sr1 O1 118.78(7) 2_746 . ?
O1W Sr1 O1 133.99(9) . . ?
O2 Sr1 O2 115.65(7) 2_756 . ?
O3 Sr1 O2 171.59(9) 2_756 . ?
O1 Sr1 O2 70.54(8) 2_746 . ?
O1W Sr1 O2 108.13(9) . . ?
O1 Sr1 O2 48.81(8) . . ?
O2 Sr1 O4 63.22(9) 2_756 3_766 ?
O3 Sr1 O4 118.24(9) 2_756 3_766 ?
O1 Sr1 O4 102.53(9) 2_746 3_766 ?
O1W Sr1 O4 67.05(9) . 3_766 ?
O1 Sr1 O4 67.37(9) . 3_766 ?
O2 Sr1 O4 69.97(9) . 3_766 ?
O2 Sr1 O3 115.70(9) 2_756 4_566 ?
O3 Sr1 O3 65.10(11) 2_756 4_566 ?
O1 Sr1 O3 80.16(9) 2_746 4_566 ?
O1W Sr1 O3 118.69(9) . 4_566 ?
O1 Sr1 O3 106.87(9) . 4_566 ?
O2 Sr1 O3 106.56(8) . 4_566 ?
O4 Sr1 O3 174.24(9) 3_766 4_566 ?
O2 Sr1 O4 135.24(10) 2_756 4_566 ?
O3 Sr1 O4 111.57(9) 2_756 4_566 ?
O1 Sr1 O4 66.79(9) 2_746 4_566 ?
O1W Sr1 O4 132.82(9) . 4_566 ?
O1 Sr1 O4 75.74(9) . 4_566 ?
O2 Sr1 O4 60.07(8) . 4_566 ?
O4 Sr1 O4 129.73(5) 3_766 4_566 ?
O3 Sr1 O4 46.50(8) 4_566 4_566 ?
O2 Sr1 C4 131.37(10) 2_756 4_566 ?
O3 Sr1 C4 88.39(10) 2_756 4_566 ?
O1 Sr1 C4 69.00(10) 2_746 4_566 ?
O1W Sr1 C4 126.01(10) . 4_566 ?
O1 Sr1 C4 93.82(10) . 4_566 ?
O2 Sr1 C4 83.33(9) . 4_566 ?
O4 Sr1 C4 153.23(10) 3_766 4_566 ?
O3 Sr1 C4 23.40(9) 4_566 4_566 ?
O4 Sr1 C4 23.54(9) 4_566 4_566 ?
O2 Sr1 Sr1 39.95(6) 2_756 2_756 ?
O3 Sr1 Sr1 108.83(7) 2_756 2_756 ?
O1 Sr1 Sr1 138.91(6) 2_746 2_756 ?
O1W Sr1 Sr1 104.12(6) . 2_756 ?
O1 Sr1 Sr1 39.11(6) . 2_756 ?
O2 Sr1 Sr1 75.71(6) . 2_756 ?
O4 Sr1 Sr1 42.55(6) 3_766 2_756 ?
O3 Sr1 Sr1 132.74(7) 4_566 2_756 ?
O4 Sr1 Sr1 114.62(7) 4_566 2_756 ?
C4 Sr1 Sr1 129.58(8) 4_566 2_756 ?
O2 Sr1 Sr1 152.13(6) 2_756 2_746 ?
O3 Sr1 Sr1 137.95(6) 2_756 2_746 ?
O1 Sr1 Sr1 39.58(6) 2_746 2_746 ?
O1W Sr1 Sr1 99.96(6) . 2_746 ?
O1 Sr1 Sr1 80.62(6) . 2_746 ?
O2 Sr1 Sr1 36.60(6) . 2_746 ?
O4 Sr1 Sr1 98.28(6) 3_766 2_746 ?
O3 Sr1 Sr1 80.50(6) 4_566 2_746 ?
O4 Sr1 Sr1 41.35(6) 4_566 2_746 ?
C4 Sr1 Sr1 58.52(7) 4_566 2_746 ?
Sr1 Sr1 Sr1 112.27(4) 2_756 2_746 ?

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
O2 C1 C2 N1 -168.5(4) . . . . ?
O1 C1 C2 N1 6.7(6) . . . . ?
O2 C1 C2 C3 -1.3(7) . . . . ?
O1 C1 C2 C3 174.0(4) . . . . ?
N1 C2 C3 N2 0.5(5) . . . . ?
C1 C2 C3 N2 -167.6(4) . . . . ?
N1 C2 C3 C4 174.3(5) . . . . ?
C1 C2 C3 C4 6.1(8) . . . . ?
N2 C3 C4 O3 -170.5(4) . . . . ?
C2 C3 C4 O3 16.3(8) . . . . ?
N2 C3 C4 O4 10.3(6) . . . . ?
C2 C3 C4 O4 -162.9(5) . . . . ?
N2 C3 C4 Sr1 91.2(10) . . . 4_565 ?
C2 C3 C4 Sr1 -82.0(11) . . . 4_565 ?
N1 C5 C6 C7 -108.7(5) . . . . ?
N2 C5 C6 C7 75.0(6) . . . . ?
C5 C6 C7 C10 85.9(6) . . . . ?
C5 C6 C7 C8 -97.7(5) . . . . ?
C10 C7 C8 C9 -2.5(7) . . . . ?
C6 C7 C8 C9 -179.2(5) . . . . ?
C7 C8 C9 N3 2.5(9) . . . . ?
C8 C7 C10 C11 1.3(8) . . . . ?
C6 C7 C10 C11 178.0(5) . . . . ?
C7 C10 C11 N3 0.1(9) . . . . ?
N2 C5 N1 C2 2.1(5) . . . . ?
C6 C5 N1 C2 -174.6(4) . . . . ?
C3 C2 N1 C5 -1.6(5) . . . . ?
C1 C2 N1 C5 168.2(4) . . . . ?
N1 C5 N2 C3 -1.8(5) . . . . ?
C6 C5 N2 C3 174.9(4) . . . . ?
C2 C3 N2 C5 0.7(5) . . . . ?
C4 C3 N2 C5 -174.5(4) . . . . ?
C10 C11 N3 C9 -0.4(9) . . . . ?
C8 C9 N3 C11 -1.0(9) . . . . ?
O2 C1 O1 Sr1 103.4(4) . . . 2_756 ?
C2 C1 O1 Sr1 -71.7(4) . . . 2_756 ?
O2 C1 O1 Sr1 -3.8(4) . . . . ?
C2 C1 O1 Sr1 -178.9(3) . . . . ?
O1 C1 O2 Sr1 118.9(4) . . . 2_746 ?
C2 C1 O2 Sr1 -66.1(5) . . . 2_746 ?
O1 C1 O2 Sr1 3.7(4) . . . . ?
C2 C1 O2 Sr1 178.7(3) . . . . ?
O4 C4 O3 Sr1 -174.8(4) . . . 2_746 ?
C3 C4 O3 Sr1 6.0(8) . . . 2_746 ?
Sr1 C4 O3 Sr1 169.2(6) 4_565 . . 2_746 ?
O4 C4 O3 Sr1 16.0(5) . . . 4_565 ?
C3 C4 O3 Sr1 -163.1(3) . . . 4_565 ?
O3 C4 O4 Sr1 -116.6(4) . . . 3_766 ?
C3 C4 O4 Sr1 62.6(5) . . . 3_766 ?
Sr1 C4 O4 Sr1 -100.7(3) 4_565 . . 3_766 ?
O3 C4 O4 Sr1 -15.9(4) . . . 4_565 ?
C3 C4 O4 Sr1 163.3(3) . . . 4_565 ?

_refine_diff_density_max         0.844
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.111

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1539791'
_audit_update_record             
;
2017-03-23 deposited with the CCDC.
2017-05-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H78 Mg10 N18 O61 S'
_chemical_formula_weight         2374.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mg Mg 0.0486 0.0363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c :H'
_space_group_name_Hall           'R 3 -2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   19.642(5)
_cell_length_b                   19.642(5)
_cell_length_c                   49.236(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     16451(10)
_cell_formula_units_Z            6
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1727
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      17.74

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             7344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9531
_exptl_absorpt_correction_T_max  0.9640
_exptl_absorpt_process_details   'SADABS(sheldrick, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20136
_diffrn_reflns_av_unetI/netI     0.1544
_diffrn_reflns_av_R_equivalents  0.1091
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_theta_min         1.455
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_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 0.890
_diffrn_reflns_point_group_measured_fraction_full 0.890
_reflns_number_total             5748
_reflns_number_gt                2948
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_max     0.779
_reflns_Friedel_fraction_full    0.779

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1830P)²+0.5073P] 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 742 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5748
_refine_ls_number_parameters     475
_refine_ls_number_restraints     201
_refine_ls_R_factor_all          0.1893
_refine_ls_R_factor_gt           0.1140
_refine_ls_wR_factor_ref         0.3394
_refine_ls_wR_factor_gt          0.2866
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6071(3) 0.0485(4) 0.96675(12) 0.060(2) Uani 1 1 d . U . . .
C2 C 0.6080(3) -0.0238(3) 0.97477(11) 0.0532(17) Uani 1 1 d . U . . .
C3 C 0.6267(3) -0.0752(3) 0.96190(11) 0.0529(18) Uani 1 1 d . U . . .
C4 C 0.6644(3) -0.0755(3) 0.93652(11) 0.058(2) Uani 1 1 d . U . . .
C5 C 0.5876(3) -0.1159(4) 1.00256(12) 0.063(2) Uani 1 1 d . U . . .
C6 C 0.5660(4) -0.1621(4) 1.02910(12) 0.074(2) Uani 1 1 d . U . . .
H6A H 0.5322 -0.1492 1.0396 0.089 Uiso 1 1 calc R U . . .
H6B H 0.5364 -0.2178 1.0250 0.089 Uiso 1 1 calc R U . . .
C7 C 0.6304(4) -0.1473(4) 1.04474(14) 0.075(2) Uani 1 1 d . U . . .
C8 C 0.6891(4) -0.0703(4) 1.05115(16) 0.086(2) Uani 1 1 d . U . . .
H8 H 0.6818 -0.0293 1.0454 0.103 Uiso 1 1 calc R U . . .
C9 C 0.7606(4) -0.0499(4) 1.06612(14) 0.080(3) Uani 1 1 d . U . . .
H9 H 0.7994 0.0020 1.0691 0.096 Uiso 1 1 calc R U . . .
C10 C 0.7671(4) -0.1107(4) 1.07534(15) 0.082(2) Uani 1 1 d . U . . .
H10 H 0.8119 -0.0991 1.0853 0.098 Uiso 1 1 calc R U . . .
C11 C 0.6452(4) -0.2064(4) 1.05617(13) 0.081(3) Uani 1 1 d . U . . .
H11 H 0.6078 -0.2589 1.0533 0.097 Uiso 1 1 calc R U . . .
C12 C 0.6273(3) 0.1774(3) 0.87589(12) 0.0525(18) Uani 1 1 d . U . . .
C13 C 0.6736(3) 0.1874(3) 0.85170(10) 0.0472(16) Uani 1 1 d . U . . .
C14 C 0.7019(3) 0.1402(3) 0.83954(11) 0.0574(19) Uani 1 1 d . U . . .
C15 C 0.6991(3) 0.0666(3) 0.84563(11) 0.0499(18) Uani 1 1 d . U . . .
C16 C 0.7397(3) 0.2478(3) 0.81572(9) 0.0406(15) Uani 1 1 d . U . . .
C17 C 0.7747(4) 0.3076(3) 0.79364(12) 0.061(2) Uani 1 1 d . U . . .
H17A H 0.7386 0.3263 0.7892 0.073 Uiso 1 1 calc R U . . .
H17B H 0.7812 0.2830 0.7775 0.073 Uiso 1 1 calc R U . . .
C18 C 0.8542(4) 0.3778(3) 0.80147(14) 0.071(2) Uani 1 1 d . U . . .
C19 C 0.9036(4) 0.3808(4) 0.82064(16) 0.087(3) Uani 1 1 d . U . . .
H19 H 0.8883 0.3353 0.8307 0.104 Uiso 1 1 calc R U . . .
C20 C 0.9756(5) 0.4453(5) 0.8268(2) 0.117(4) Uani 1 1 d . U . . .
H20 H 1.0093 0.4468 0.8404 0.141 Uiso 1 1 calc R U . . .
C21 C 0.9913(4) 0.5120(4) 0.80869(19) 0.090(3) Uani 1 1 d . U . . .
H21 H 1.0388 0.5581 0.8116 0.108 Uiso 1 1 calc R U . . .
C22 C 0.8826(4) 0.4477(4) 0.78619(16) 0.089(3) Uani 1 1 d . U . . .
H22 H 0.8516 0.4474 0.7719 0.107 Uiso 1 1 calc R U . . .
Mg1 Mg 0.80001(10) 0.12391(10) 0.79727(3) 0.0484(5) Uani 1 1 d . . . . .
Mg2 Mg 0.64230(11) 0.04873(10) 0.90512(4) 0.0557(6) Uani 1 1 d . . . . .
Mg3 Mg 0.6667 0.3333 0.85592(6) 0.0459(8) Uani 1 3 d S T P . .
Mg4 Mg 0.52711(11) 0.00993(13) 1.01874(4) 0.0717(7) Uani 1 1 d . . . . .
N1 N 0.5792(2) -0.0522(3) 1.00055(9) 0.0613(15) Uani 1 1 d . U . . .
N2 N 0.6151(2) -0.1327(3) 0.98108(10) 0.0572(16) Uani 1 1 d . U . . .
N3 N 0.7123(3) -0.1896(3) 1.07124(10) 0.0633(17) Uani 1 1 d . U . . .
N4 N 0.6955(2) 0.2528(2) 0.83593(8) 0.0462(13) Uani 1 1 d . U . . .
N5 N 0.7450(3) 0.1814(2) 0.81635(9) 0.0521(15) Uani 1 1 d . U . . .
N6 N 0.9507(4) 0.5146(4) 0.79058(17) 0.103(3) Uani 1 1 d . U . . .
O1 O 0.5852(2) 0.0805(2) 0.98569(9) 0.0858(16) Uani 1 1 d . . . . .
O2 O 0.6304(2) 0.0801(2) 0.94391(8) 0.0681(13) Uani 1 1 d . . . . .
O3 O 0.6765(2) -0.0259(2) 0.91753(8) 0.0677(13) Uani 1 1 d . . . . .
O4 O 0.6825(2) -0.1288(2) 0.93335(8) 0.0612(13) Uani 1 1 d . . . . .
O5 O 0.6143(2) 0.23417(18) 0.88112(7) 0.0528(12) Uani 1 1 d . . . . .
O6 O 0.6035(2) 0.1193(2) 0.89156(8) 0.0661(13) Uani 1 1 d . . . . .
O7 O 0.6578(2) 0.02456(19) 0.86459(8) 0.0591(13) Uani 1 1 d . . . . .
O8 O 0.7353(2) 0.04798(19) 0.82922(8) 0.0548(12) Uani 1 1 d . . . . .
O1W O 0.7036(3) 0.0600(3) 0.77047(9) 0.0836(19) Uani 1 1 d . . . . .
H1WA H 0.6650 0.0209 0.7639 0.100 Uiso 1 1 d R U . . .
H1WB H 0.7188 0.0988 0.7599 0.100 Uiso 1 1 d R U . . .
O2W O 0.8397(3) 0.0505(2) 0.78378(12) 0.101(2) Uani 1 1 d . . . . .
H2WA H 0.8643 0.0309 0.7763 0.121 Uiso 1 1 d R U . . .
H2WB H 0.8017 0.0156 0.7927 0.121 Uiso 1 1 d R U . . .
O3W O 0.5257(3) -0.0424(3) 0.90463(12) 0.090(2) Uani 1 1 d . . . . .
H3WA H 0.4885 -0.0747 0.8948 0.108 Uiso 1 1 d R U . . .
H3WB H 0.5215 -0.0603 0.9203 0.108 Uiso 1 1 d R U . . .
O4W O 0.6156(3) 0.0814(4) 1.04510(14) 0.183(3) Uani 1 1 d . . . . .
H4WA H 0.6413 0.1041 1.0593 0.219 Uiso 1 1 d R U . . .
H4WB H 0.6439 0.0977 1.0316 0.219 Uiso 1 1 d R U . . .
O5W O 0.4814(4) -0.0651(3) 1.05243(12) 0.144(2) Uani 1 1 d . . . . .
H5WA H 0.4478 -0.1004 1.0629 0.173 Uiso 1 1 d R U . . .
H5WB H 0.5256 -0.0449 1.0594 0.173 Uiso 1 1 d R U . . .
O6W O 0.4242(3) -0.0647(3) 0.99771(13) 0.107(2) Uani 1 1 d . . . . .
H6WA H 0.3838 -0.0602 0.9954 0.129 Uiso 1 1 d R U . . .
H6WB H 0.4166 -0.1066 0.9907 0.129 Uiso 1 1 d R U . . .
O7W O 0.4723(3) 0.0730(3) 1.02751(11) 0.0949(19) Uani 1 1 d . . . . .
H7WA H 0.4507 0.0972 1.0212 0.114 Uiso 1 1 d R U . . .
H7WB H 0.4745 0.0772 1.0447 0.114 Uiso 1 1 d R U . . .
O8W O 0.4336(5) 0.0051(7) 0.9409(2) 0.245(5) Uani 1 1 d . . . . .
O10W O 0.3792(14) 0.7757(13) 0.9749(6) 0.412(9) Uani 1 1 d . U . . .
O11W O 0.3557(15) 0.7506(12) 0.0458(7) 0.409(9) Uani 1 1 d . U . . .
O9W O 0.5612(5) 0.2444(5) 0.0483(3) 0.450(5) Uani 1 1 d . . . . .
S1 S 0.6667 0.3333 0.96050(9) 0.1229(16) Uani 1 3 d DS TU P . .
O9 O 0.6144(3) 0.2359(3) 0.93702(11) 0.065(2) Uani 0.6667 1 d D U P . .
O10 O 0.6772(4) 0.2581(4) 0.98561(14) 0.085(3) Uani 0.6667 1 d D 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
C1 O2 1.255(7) . ?
C1 O1 1.313(8) . ?
C1 C2 1.483(10) . ?
C2 C3 1.388(10) . ?
C2 N1 1.388(7) . ?
C3 N2 1.401(8) . ?
C3 C4 1.453(8) . ?
C4 O4 1.274(9) . ?
C4 O3 1.283(7) . ?
C5 N2 1.303(8) . ?
C5 N1 1.346(10) . ?
C5 C6 1.525(9) . ?
C6 C7 1.382(10) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.404(8) . ?
C7 C11 1.445(12) . ?
C8 C9 1.453(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.342(12) . ?
C9 H9 0.9300 . ?
C10 N3 1.391(8) . ?
C10 H10 0.9300 . ?
C11 N3 1.402(9) . ?
C11 H11 0.9300 . ?
C12 O6 1.259(7) . ?
C12 O5 1.287(8) . ?
C12 C13 1.452(8) . ?
C13 N4 1.373(7) . ?
C13 C14 1.430(10) . ?
C14 N5 1.411(7) . ?
C14 C15 1.449(9) . ?
C15 O7 1.241(6) . ?
C15 O8 1.246(7) . ?
C16 N4 1.356(7) . ?
C16 N5 1.360(8) . ?
C16 C17 1.492(7) . ?
C17 C18 1.528(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.335(11) . ?
C18 C22 1.412(10) . ?
C19 C20 1.381(10) . ?
C19 H19 0.9300 . ?
C20 C21 1.485(14) . ?
C20 H20 0.9300 . ?
C21 N6 1.214(12) . ?
C21 H21 0.9300 . ?
C22 N6 1.343(8) . ?
C22 H22 0.9300 . ?
Mg1 O4 2.057(4) 11_654 ?
Mg1 O2W 2.062(6) . ?
Mg1 O8 2.102(4) . ?
Mg1 O1W 2.128(5) . ?
Mg1 N5 2.132(6) . ?
Mg1 N2 2.217(6) 11_654 ?
Mg1 H1WB 2.3217 . ?
Mg1 H2WB 2.1569 . ?
Mg2 O3 1.989(5) . ?
Mg2 O6 2.001(5) . ?
Mg2 O2 2.055(4) . ?
Mg2 O3W 2.086(4) . ?
Mg2 O7 2.109(4) . ?
Mg2 N3 2.185(7) 11_654 ?
Mg2 H3WB 2.3858 . ?
Mg3 O5 2.095(4) 2_655 ?
Mg3 O5 2.095(4) 3_665 ?
Mg3 O5 2.095(4) . ?
Mg3 N4 2.165(5) . ?
Mg3 N4 2.165(5) 2_655 ?
Mg3 N4 2.165(5) 3_665 ?
Mg4 O7W 2.052(7) . ?
Mg4 O4W 2.058(6) . ?
Mg4 O1 2.071(5) . ?
Mg4 O6W 2.084(5) . ?
Mg4 O5W 2.099(6) . ?
Mg4 N1 2.141(6) . ?
Mg4 H4WB 2.1629 . ?
Mg4 H5WB 2.2670 . ?
Mg4 H7WB 2.4103 . ?
N2 Mg1 2.217(6) 17_644 ?
N3 Mg2 2.186(6) 17_644 ?
O4 Mg1 2.058(4) 17_644 ?
O1W H1WA 0.8285 . ?
O1W H1WB 0.8462 . ?
O2W H2WA 0.8393 . ?
O2W H2WB 0.8407 . ?
O3W H3WA 0.8402 . ?
O3W H3WB 0.8334 . ?
O4W H4WA 0.8455 . ?
O4W H4WB 0.8227 . ?
O5W H5WA 0.8499 . ?
O5W H5WB 0.8276 . ?
O6W H6WA 0.8479 . ?
O6W H6WB 0.8340 . ?
O7W H7WA 0.8377 . ?
O7W H7WB 0.8476 . ?
S1 O10 2.015(8) . ?
S1 O10 2.015(8) 2_655 ?
S1 O10 2.015(8) 3_665 ?
S1 O9 2.022(6) 2_655 ?
S1 O9 2.022(6) . ?
S1 O9 2.022(6) 3_665 ?

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 C1 O1 121.7(6) . . ?
O2 C1 C2 122.4(6) . . ?
O1 C1 C2 115.8(5) . . ?
C3 C2 N1 109.2(5) . . ?
C3 C2 C1 135.2(5) . . ?
N1 C2 C1 115.4(6) . . ?
C2 C3 N2 106.4(5) . . ?
C2 C3 C4 135.7(6) . . ?
N2 C3 C4 117.1(6) . . ?
O4 C4 O3 120.8(5) . . ?
O4 C4 C3 117.4(5) . . ?
O3 C4 C3 121.7(6) . . ?
N2 C5 N1 115.8(5) . . ?
N2 C5 C6 124.9(7) . . ?
N1 C5 C6 119.3(6) . . ?
C7 C6 C5 113.6(5) . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 C8 121.7(7) . . ?
C6 C7 C11 125.3(6) . . ?
C8 C7 C11 113.0(7) . . ?
C7 C8 C9 124.8(8) . . ?
C7 C8 H8 117.6 . . ?
C9 C8 H8 117.6 . . ?
C10 C9 C8 115.8(6) . . ?
C10 C9 H9 122.1 . . ?
C8 C9 H9 122.1 . . ?
C9 C10 N3 125.3(7) . . ?
C9 C10 H10 117.3 . . ?
N3 C10 H10 117.3 . . ?
N3 C11 C7 124.1(6) . . ?
N3 C11 H11 118.0 . . ?
C7 C11 H11 118.0 . . ?
O6 C12 O5 121.3(5) . . ?
O6 C12 C13 123.3(6) . . ?
O5 C12 C13 115.4(5) . . ?
N4 C13 C14 109.2(5) . . ?
N4 C13 C12 118.2(6) . . ?
C14 C13 C12 132.6(5) . . ?
N5 C14 C13 106.4(5) . . ?
N5 C14 C15 116.9(6) . . ?
C13 C14 C15 136.6(5) . . ?
O7 C15 O8 124.8(6) . . ?
O7 C15 C14 120.4(6) . . ?
O8 C15 C14 114.6(5) . . ?
N4 C16 N5 114.3(4) . . ?
N4 C16 C17 122.5(5) . . ?
N5 C16 C17 123.1(5) . . ?
C16 C17 C18 112.8(5) . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 C22 114.1(6) . . ?
C19 C18 C17 127.6(6) . . ?
C22 C18 C17 118.1(6) . . ?
C18 C19 C20 125.7(8) . . ?
C18 C19 H19 117.1 . . ?
C20 C19 H19 117.1 . . ?
C19 C20 C21 110.1(9) . . ?
C19 C20 H20 124.9 . . ?
C21 C20 H20 124.9 . . ?
N6 C21 C20 128.8(6) . . ?
N6 C21 H21 115.6 . . ?
C20 C21 H21 115.6 . . ?
N6 C22 C18 125.5(8) . . ?
N6 C22 H22 117.2 . . ?
C18 C22 H22 117.2 . . ?
O4 Mg1 O2W 93.66(19) 11_654 . ?
O4 Mg1 O8 173.1(2) 11_654 . ?
O2W Mg1 O8 92.9(2) . . ?
O4 Mg1 O1W 88.41(18) 11_654 . ?
O2W Mg1 O1W 85.6(2) . . ?
O8 Mg1 O1W 90.07(16) . . ?
O4 Mg1 N5 97.31(18) 11_654 . ?
O2W Mg1 N5 168.9(2) . . ?
O8 Mg1 N5 76.07(17) . . ?
O1W Mg1 N5 92.8(2) . . ?
O4 Mg1 N2 77.53(19) 11_654 11_654 ?
O2W Mg1 N2 87.71(18) . 11_654 ?
O8 Mg1 N2 104.78(17) . 11_654 ?
O1W Mg1 N2 164.0(2) . 11_654 ?
N5 Mg1 N2 96.46(17) . 11_654 ?
O4 Mg1 H1WB 68.0 11_654 . ?
O2W Mg1 H1WB 93.2 . . ?
O8 Mg1 H1WB 109.6 . . ?
O1W Mg1 H1WB 21.4 . . ?
N5 Mg1 H1WB 89.2 . . ?
N2 Mg1 H1WB 145.5 11_654 . ?
O4 Mg1 H2WB 114.8 11_654 . ?
O2W Mg1 H2WB 22.8 . . ?
O8 Mg1 H2WB 71.4 . . ?
O1W Mg1 H2WB 78.5 . . ?
N5 Mg1 H2WB 146.2 . . ?
N2 Mg1 H2WB 100.4 11_654 . ?
H1WB Mg1 H2WB 93.2 . . ?
O3 Mg2 O6 177.03(17) . . ?
O3 Mg2 O2 93.80(19) . . ?
O6 Mg2 O2 87.9(2) . . ?
O3 Mg2 O3W 90.1(2) . . ?
O6 Mg2 O3W 87.4(2) . . ?
O2 Mg2 O3W 91.6(2) . . ?
O3 Mg2 O7 89.10(19) . . ?
O6 Mg2 O7 89.33(19) . . ?
O2 Mg2 O7 176.17(18) . . ?
O3W Mg2 O7 90.9(2) . . ?
O3 Mg2 N3 90.03(18) . 11_654 ?
O6 Mg2 N3 92.42(17) . 11_654 ?
O2 Mg2 N3 89.83(18) . 11_654 ?
O3W Mg2 N3 178.6(2) . 11_654 ?
O7 Mg2 N3 87.66(17) . 11_654 ?
O3 Mg2 H3WB 78.0 . . ?
O6 Mg2 H3WB 100.0 . . ?
O2 Mg2 H3WB 76.6 . . ?
O3W Mg2 H3WB 20.1 . . ?
O7 Mg2 H3WB 106.5 . . ?
N3 Mg2 H3WB 161.1 11_654 . ?
O5 Mg3 O5 88.51(16) 2_655 3_665 ?
O5 Mg3 O5 88.51(17) 2_655 . ?
O5 Mg3 O5 88.51(16) 3_665 . ?
O5 Mg3 N4 93.67(15) 2_655 . ?
O5 Mg3 N4 165.34(17) 3_665 . ?
O5 Mg3 N4 77.07(15) . . ?
O5 Mg3 N4 77.07(15) 2_655 2_655 ?
O5 Mg3 N4 93.68(15) 3_665 2_655 ?
O5 Mg3 N4 165.34(17) . 2_655 ?
N4 Mg3 N4 100.94(17) . 2_655 ?
O5 Mg3 N4 165.34(17) 2_655 3_665 ?
O5 Mg3 N4 77.07(15) 3_665 3_665 ?
O5 Mg3 N4 93.68(15) . 3_665 ?
N4 Mg3 N4 100.95(17) . 3_665 ?
N4 Mg3 N4 100.94(17) 2_655 3_665 ?
O7W Mg4 O4W 88.6(3) . . ?
O7W Mg4 O1 92.3(2) . . ?
O4W Mg4 O1 92.5(2) . . ?
O7W Mg4 O6W 84.9(2) . . ?
O4W Mg4 O6W 169.9(3) . . ?
O1 Mg4 O6W 95.5(2) . . ?
O7W Mg4 O5W 95.1(3) . . ?
O4W Mg4 O5W 84.2(3) . . ?
O1 Mg4 O5W 171.9(3) . . ?
O6W Mg4 O5W 88.6(2) . . ?
O7W Mg4 N1 167.4(2) . . ?
O4W Mg4 N1 99.8(3) . . ?
O1 Mg4 N1 78.0(2) . . ?
O6W Mg4 N1 87.9(2) . . ?
O5W Mg4 N1 95.1(3) . . ?
O7W Mg4 H4WB 97.2 . . ?
O4W Mg4 H4WB 22.3 . . ?
O1 Mg4 H4WB 71.7 . . ?
O6W Mg4 H4WB 167.1 . . ?
O5W Mg4 H4WB 103.9 . . ?
N1 Mg4 H4WB 87.6 . . ?
O7W Mg4 H5WB 102.4 . . ?
O4W Mg4 H5WB 64.7 . . ?
O1 Mg4 H5WB 152.1 . . ?
O6W Mg4 H5WB 109.1 . . ?
O5W Mg4 H5WB 21.4 . . ?
N1 Mg4 H5WB 89.7 . . ?
H4WB Mg4 H5WB 83.0 . . ?
O7W Mg4 H7WB 19.9 . . ?
O4W Mg4 H7WB 75.0 . . ?
O1 Mg4 H7WB 107.0 . . ?
O6W Mg4 H7WB 96.7 . . ?
O5W Mg4 H7WB 79.4 . . ?
N1 Mg4 H7WB 172.7 . . ?
H4WB Mg4 H7WB 89.0 . . ?
H5WB Mg4 H7WB 83.4 . . ?
C5 N1 C2 103.0(5) . . ?
C5 N1 Mg4 144.6(4) . . ?
C2 N1 Mg4 111.7(4) . . ?
C5 N2 C3 105.3(6) . . ?
C5 N2 Mg1 145.5(5) . 17_644 ?
C3 N2 Mg1 109.0(4) . 17_644 ?
C10 N3 C11 116.9(6) . . ?
C10 N3 Mg2 124.5(5) . 17_644 ?
C11 N3 Mg2 114.2(5) . 17_644 ?
C16 N4 C13 105.1(5) . . ?
C16 N4 Mg3 142.8(3) . . ?
C13 N4 Mg3 110.6(4) . . ?
C16 N5 C14 104.9(5) . . ?
C16 N5 Mg1 143.2(3) . . ?
C14 N5 Mg1 111.7(4) . . ?
C21 N6 C22 115.6(7) . . ?
C1 O1 Mg4 116.1(4) . . ?
C1 O2 Mg2 138.8(4) . . ?
C4 O3 Mg2 141.3(4) . . ?
C4 O4 Mg1 119.0(3) . 17_644 ?
C12 O5 Mg3 117.9(3) . . ?
C12 O6 Mg2 137.4(4) . . ?
C15 O7 Mg2 133.0(3) . . ?
C15 O8 Mg1 120.6(4) . . ?
Mg1 O1W H1WA 157.0 . . ?
Mg1 O1W H1WB 92.4 . . ?
H1WA O1W H1WB 110.1 . . ?
Mg1 O2W H2WA 165.5 . . ?
Mg1 O2W H2WB 84.9 . . ?
H2WA O2W H2WB 109.6 . . ?
Mg2 O3W H3WA 145.3 . . ?
Mg2 O3W H3WB 100.7 . . ?
H3WA O3W H3WB 110.2 . . ?
Mg4 O4W H4WA 163.2 . . ?
Mg4 O4W H4WB 86.0 . . ?
H4WA O4W H4WB 110.7 . . ?
Mg4 O5W H5WA 159.4 . . ?
Mg4 O5W H5WB 90.8 . . ?
H5WA O5W H5WB 109.8 . . ?
Mg4 O6W H6WA 128.5 . . ?
Mg4 O6W H6WB 122.0 . . ?
H6WA O6W H6WB 109.4 . . ?
Mg4 O7W H7WA 146.2 . . ?
Mg4 O7W H7WB 104.6 . . ?
H7WA O7W H7WB 109.1 . . ?
O10 S1 O10 86.3(3) . 2_655 ?
O10 S1 O10 86.3(3) . 3_665 ?
O10 S1 O10 86.3(3) 2_655 3_665 ?
O10 S1 O9 104.6(3) . 2_655 ?
O10 S1 O9 81.2(3) 2_655 2_655 ?
O10 S1 O9 162.7(3) 3_665 2_655 ?
O10 S1 O9 81.2(3) . . ?
O10 S1 O9 162.7(3) 2_655 . ?
O10 S1 O9 104.6(3) 3_665 . ?
O9 S1 O9 90.6(3) 2_655 . ?
O10 S1 O9 162.7(3) . 3_665 ?
O10 S1 O9 104.6(3) 2_655 3_665 ?
O10 S1 O9 81.2(3) 3_665 3_665 ?
O9 S1 O9 90.5(3) 2_655 3_665 ?
O9 S1 O9 90.6(3) . 3_665 ?

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
O2 C1 C2 C3 -4.1(9) . . . . ?
O1 C1 C2 C3 -179.7(5) . . . . ?
O2 C1 C2 N1 -179.0(5) . . . . ?
O1 C1 C2 N1 5.3(7) . . . . ?
N1 C2 C3 N2 -4.9(6) . . . . ?
C1 C2 C3 N2 180.0(5) . . . . ?
N1 C2 C3 C4 -173.6(6) . . . . ?
C1 C2 C3 C4 11.2(11) . . . . ?
C2 C3 C4 O4 169.3(6) . . . . ?
N2 C3 C4 O4 1.4(7) . . . . ?
C2 C3 C4 O3 -13.3(10) . . . . ?
N2 C3 C4 O3 178.9(4) . . . . ?
N2 C5 C6 C7 76.6(8) . . . . ?
N1 C5 C6 C7 -102.6(8) . . . . ?
C5 C6 C7 C8 50.9(10) . . . . ?
C5 C6 C7 C11 -129.2(7) . . . . ?
C6 C7 C8 C9 -176.3(7) . . . . ?
C11 C7 C8 C9 3.9(11) . . . . ?
C7 C8 C9 C10 -3.5(12) . . . . ?
C8 C9 C10 N3 1.2(11) . . . . ?
C6 C7 C11 N3 177.8(7) . . . . ?
C8 C7 C11 N3 -2.3(10) . . . . ?
O6 C12 C13 N4 179.2(5) . . . . ?
O5 C12 C13 N4 -3.5(7) . . . . ?
O6 C12 C13 C14 0.9(9) . . . . ?
O5 C12 C13 C14 178.2(5) . . . . ?
N4 C13 C14 N5 2.6(6) . . . . ?
C12 C13 C14 N5 -179.0(5) . . . . ?
N4 C13 C14 C15 180.0(6) . . . . ?
C12 C13 C14 C15 -1.6(11) . . . . ?
N5 C14 C15 O7 -175.0(5) . . . . ?
C13 C14 C15 O7 7.8(10) . . . . ?
N5 C14 C15 O8 -0.6(7) . . . . ?
C13 C14 C15 O8 -177.7(6) . . . . ?
N4 C16 C17 C18 85.9(7) . . . . ?
N5 C16 C17 C18 -98.5(6) . . . . ?
C16 C17 C18 C19 21.6(11) . . . . ?
C16 C17 C18 C22 -162.0(7) . . . . ?
C22 C18 C19 C20 2.6(14) . . . . ?
C17 C18 C19 C20 179.1(9) . . . . ?
C18 C19 C20 C21 -0.8(15) . . . . ?
C19 C20 C21 N6 -0.3(16) . . . . ?
C19 C18 C22 N6 -3.8(13) . . . . ?
C17 C18 C22 N6 179.3(8) . . . . ?
N2 C5 N1 C2 -2.4(6) . . . . ?
C6 C5 N1 C2 176.8(5) . . . . ?
N2 C5 N1 Mg4 165.9(4) . . . . ?
C6 C5 N1 Mg4 -14.9(9) . . . . ?
C3 C2 N1 C5 4.4(5) . . . . ?
C1 C2 N1 C5 -179.3(4) . . . . ?
C3 C2 N1 Mg4 -168.3(3) . . . . ?
C1 C2 N1 Mg4 7.9(5) . . . . ?
N1 C5 N2 C3 -0.5(6) . . . . ?
C6 C5 N2 C3 -179.7(5) . . . . ?
N1 C5 N2 Mg1 173.6(4) . . . 17_644 ?
C6 C5 N2 Mg1 -5.6(10) . . . 17_644 ?
C2 C3 N2 C5 3.3(5) . . . . ?
C4 C3 N2 C5 174.4(5) . . . . ?
C2 C3 N2 Mg1 -173.2(3) . . . 17_644 ?
C4 C3 N2 Mg1 -2.1(5) . . . 17_644 ?
C9 C10 N3 C11 0.2(11) . . . . ?
C9 C10 N3 Mg2 155.1(6) . . . 17_644 ?
C7 C11 N3 C10 0.4(10) . . . . ?
C7 C11 N3 Mg2 -157.1(6) . . . 17_644 ?
N5 C16 N4 C13 3.2(5) . . . . ?
C17 C16 N4 C13 179.2(4) . . . . ?
N5 C16 N4 Mg3 166.9(4) . . . . ?
C17 C16 N4 Mg3 -17.2(8) . . . . ?
C14 C13 N4 C16 -3.5(5) . . . . ?
C12 C13 N4 C16 177.9(4) . . . . ?
C14 C13 N4 Mg3 -173.0(3) . . . . ?
C12 C13 N4 Mg3 8.3(5) . . . . ?
N4 C16 N5 C14 -1.6(5) . . . . ?
C17 C16 N5 C14 -177.5(5) . . . . ?
N4 C16 N5 Mg1 -175.3(4) . . . . ?
C17 C16 N5 Mg1 8.8(9) . . . . ?
C13 C14 N5 C16 -0.6(5) . . . . ?
C15 C14 N5 C16 -178.6(4) . . . . ?
C13 C14 N5 Mg1 175.3(3) . . . . ?
C15 C14 N5 Mg1 -2.7(6) . . . . ?
C20 C21 N6 C22 -0.7(16) . . . . ?
C18 C22 N6 C21 2.9(14) . . . . ?
O2 C1 O1 Mg4 167.7(4) . . . . ?
C2 C1 O1 Mg4 -16.6(6) . . . . ?
O1 C1 O2 Mg2 -158.7(4) . . . . ?
C2 C1 O2 Mg2 25.9(9) . . . . ?
O4 C4 O3 Mg2 160.0(4) . . . . ?
C3 C4 O3 Mg2 -17.3(8) . . . . ?
O3 C4 O4 Mg1 -177.4(4) . . . 17_644 ?
C3 C4 O4 Mg1 0.1(6) . . . 17_644 ?
O6 C12 O5 Mg3 173.6(4) . . . . ?
C13 C12 O5 Mg3 -3.8(6) . . . . ?
O5 C12 O6 Mg2 -142.6(5) . . . . ?
C13 C12 O6 Mg2 34.5(8) . . . . ?
O8 C15 O7 Mg2 139.8(5) . . . . ?
C14 C15 O7 Mg2 -46.3(8) . . . . ?
O7 C15 O8 Mg1 178.0(4) . . . . ?
C14 C15 O8 Mg1 3.8(6) . . . . ?

_refine_diff_density_max         1.359
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.134

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1539786'
_audit_update_record             
;
2017-03-23 deposited with the CCDC.
2017-05-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H9 Ba N3 O5'
_chemical_formula_sum            'C11 H9 Ba N3 O5'
_chemical_formula_weight         400.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ba Ba -0.3244 2.2819 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.589(3)
_cell_length_b                   7.0523(16)
_cell_length_c                   13.358(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.582(3)
_cell_angle_gamma                90
_cell_volume                     1259.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2026
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      26.78

_exptl_crystal_description       Plate-like
_exptl_crystal_colour            Pale-brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.112
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   0.427
_exptl_transmission_factor_max   0.621
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    3.177
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4699
_exptl_absorpt_correction_T_max  0.6472
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6515
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.523
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2450
_reflns_number_gt                1979
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0562P)²] 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_number_reflns         2450
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1019
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
Ba1 Ba 0.46758(3) 0.54590(4) -0.34943(2) 0.02668(15) Uani 1 1 d . . . . .
C1 C 0.6002(4) 0.5565(7) -0.0914(4) 0.0246(12) Uani 1 1 d . . . . .
C2 C 0.6570(4) 0.5780(7) 0.0294(4) 0.0265(12) Uani 1 1 d . . . . .
C3 C 0.6604(4) 0.4677(7) 0.1162(4) 0.0237(11) Uani 1 1 d . . . . .
C4 C 0.6163(4) 0.2825(8) 0.1310(4) 0.0278(12) Uani 1 1 d . . . . .
C5 C 0.7393(4) 0.7391(8) 0.1754(5) 0.0327(13) Uani 1 1 d . . . . .
C6 C 0.7935(5) 0.8980(9) 0.2515(5) 0.0436(16) Uani 1 1 d . . . . .
H6A H 0.7600 0.9249 0.2997 0.052 Uiso 1 1 calc R U . . .
H6B H 0.7899 1.0113 0.2089 0.052 Uiso 1 1 calc R U . . .
C7 C 0.9027(5) 0.8528(9) 0.3202(5) 0.0418(15) Uani 1 1 d . . . . .
C8 C 0.9329(6) 0.7772(11) 0.4249(6) 0.063(2) Uani 1 1 d . . . . .
H8 H 0.8868 0.7525 0.4551 0.075 Uiso 1 1 calc R U . . .
C9 C 1.0339(8) 0.7399(12) 0.4827(7) 0.075(3) Uani 1 1 d . . . . .
H9 H 1.0535 0.6878 0.5521 0.090 Uiso 1 1 calc R U . . .
C10 C 0.9756(6) 0.8894(13) 0.2836(7) 0.063(2) Uani 1 1 d . . . . .
H10 H 0.9590 0.9410 0.2145 0.075 Uiso 1 1 calc R U . . .
C11 C 1.0737(7) 0.8501(15) 0.3489(9) 0.082(3) Uani 1 1 d . . . . .
H11 H 1.1221 0.8800 0.3226 0.099 Uiso 1 1 calc R U . . .
N1 N 0.7071(4) 0.7472(7) 0.0676(4) 0.0341(11) Uani 1 1 d . . . . .
N2 N 0.7133(3) 0.5734(6) 0.2075(4) 0.0308(11) Uani 1 1 d . . . . .
H2 H 0.7275 0.5397 0.2739 0.037 Uiso 1 1 calc R U . . .
N3 N 1.1034(5) 0.7727(10) 0.4466(7) 0.073(2) Uani 1 1 d . . . . .
O1 O 0.6105(3) 0.6869(5) -0.1510(3) 0.0323(9) Uani 1 1 d . . . . .
O2 O 0.5412(3) 0.4203(5) -0.1277(3) 0.0309(9) Uani 1 1 d . . . . .
O3 O 0.5801(3) 0.1682(6) 0.0547(3) 0.0396(10) Uani 1 1 d . . . . .
O4 O 0.6196(3) 0.2553(5) 0.2255(3) 0.0347(9) Uani 1 1 d . . . . .
O1W O 0.2581(3) 0.5180(6) -0.4319(3) 0.0399(10) Uani 1 1 d . . . . .
H1WA H 0.2538 0.4186 -0.4696 0.048 Uiso 1 1 d R U . . .
H1WB H 0.2192 0.6007 -0.4739 0.048 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
Ba1 O2 2.655(4) 2_654 ?
Ba1 O3 2.688(4) 2_654 ?
Ba1 O1 2.777(4) 2_644 ?
Ba1 O1W 2.810(4) . ?
Ba1 O1 2.818(4) . ?
Ba1 O4 2.830(4) 3_665 ?
Ba1 O2 2.858(4) . ?
Ba1 O3 2.880(4) 4_565 ?
Ba1 O4 2.942(4) 4_565 ?
Ba1 C4 3.254(5) 4_565 ?
Ba1 Ba1 4.2865(8) 2_654 ?
Ba1 Ba1 4.2865(8) 2_644 ?
C1 O2 1.251(6) . ?
C1 O1 1.264(6) . ?
C1 C2 1.497(7) . ?
C2 C3 1.380(7) . ?
C2 N1 1.386(7) . ?
C3 N2 1.374(7) . ?
C3 C4 1.504(7) . ?
C4 O3 1.239(6) . ?
C4 O4 1.259(6) . ?
C4 Ba1 3.254(5) 4_566 ?
C5 N1 1.325(7) . ?
C5 N2 1.351(7) . ?
C5 C6 1.507(8) . ?
C6 C7 1.520(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C10 1.361(10) . ?
C7 C8 1.393(10) . ?
C8 C9 1.388(12) . ?
C8 H8 0.9300 . ?
C9 N3 1.305(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(12) . ?
C10 H10 0.9300 . ?
C11 N3 1.318(12) . ?
C11 H11 0.9300 . ?
N2 H2 0.8600 . ?
O1 Ba1 2.777(4) 2_654 ?
O2 Ba1 2.655(4) 2_644 ?
O3 Ba1 2.688(4) 2_644 ?
O3 Ba1 2.880(4) 4_566 ?
O4 Ba1 2.830(4) 3_665 ?
O4 Ba1 2.942(4) 4_566 ?
O1W H1WA 0.8503 . ?
O1W H1WB 0.8496 . ?

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 Ba1 O3 65.33(12) 2_654 2_654 ?
O2 Ba1 O1 154.92(11) 2_654 2_644 ?
O3 Ba1 O1 110.83(12) 2_654 2_644 ?
O2 Ba1 O1W 91.69(12) 2_654 . ?
O3 Ba1 O1W 79.95(13) 2_654 . ?
O1 Ba1 O1W 63.53(12) 2_644 . ?
O2 Ba1 O1 74.99(11) 2_654 . ?
O3 Ba1 O1 129.69(12) 2_654 . ?
O1 Ba1 O1 118.01(9) 2_644 . ?
O1W Ba1 O1 132.29(11) . . ?
O2 Ba1 O4 64.03(11) 2_654 3_665 ?
O3 Ba1 O4 116.39(11) 2_654 3_665 ?
O1 Ba1 O4 99.78(11) 2_644 3_665 ?
O1W Ba1 O4 65.88(12) . 3_665 ?
O1 Ba1 O4 67.14(11) . 3_665 ?
O2 Ba1 O2 114.10(10) 2_654 . ?
O3 Ba1 O2 173.56(12) 2_654 . ?
O1 Ba1 O2 72.53(11) 2_644 . ?
O1W Ba1 O2 106.48(12) . . ?
O1 Ba1 O2 45.93(11) . . ?
O4 Ba1 O2 67.54(11) 3_665 . ?
O2 Ba1 O3 118.69(12) 2_654 4_565 ?
O3 Ba1 O3 71.06(13) 2_654 4_565 ?
O1 Ba1 O3 80.23(11) 2_644 4_565 ?
O1W Ba1 O3 120.85(12) . 4_565 ?
O1 Ba1 O3 105.32(12) . 4_565 ?
O4 Ba1 O3 171.58(11) 3_665 4_565 ?
O2 Ba1 O3 104.68(11) . 4_565 ?
O2 Ba1 O4 138.80(12) 2_654 4_565 ?
O3 Ba1 O4 115.54(11) 2_654 4_565 ?
O1 Ba1 O4 66.12(11) 2_644 4_565 ?
O1W Ba1 O4 129.51(12) . 4_565 ?
O1 Ba1 O4 76.19(11) . 4_565 ?
O4 Ba1 O4 127.78(7) 3_665 4_565 ?
O2 Ba1 O4 60.25(10) . 4_565 ?
O3 Ba1 O4 44.50(10) 4_565 4_565 ?
O2 Ba1 C4 134.56(12) 2_654 4_565 ?
O3 Ba1 C4 93.16(12) 2_654 4_565 ?
O1 Ba1 C4 68.81(12) 2_644 4_565 ?
O1W Ba1 C4 125.02(13) . 4_565 ?
O1 Ba1 C4 93.47(12) . 4_565 ?
O4 Ba1 C4 150.41(12) 3_665 4_565 ?
O2 Ba1 C4 82.90(12) . 4_565 ?
O3 Ba1 C4 22.25(11) 4_565 4_565 ?
O4 Ba1 C4 22.73(11) 4_565 4_565 ?
O2 Ba1 Ba1 40.70(8) 2_654 2_654 ?
O3 Ba1 Ba1 105.74(9) 2_654 2_654 ?
O1 Ba1 Ba1 137.53(8) 2_644 2_654 ?
O1W Ba1 Ba1 103.67(8) . 2_654 ?
O1 Ba1 Ba1 39.65(8) . 2_654 ?
O4 Ba1 Ba1 43.05(8) 3_665 2_654 ?
O2 Ba1 Ba1 73.40(8) . 2_654 ?
O3 Ba1 Ba1 133.08(9) 4_565 2_654 ?
O4 Ba1 Ba1 115.70(8) 4_565 2_654 ?
C4 Ba1 Ba1 130.26(10) 4_565 2_654 ?
O2 Ba1 Ba1 151.39(8) 2_654 2_644 ?
O3 Ba1 Ba1 143.05(8) 2_654 2_644 ?
O1 Ba1 Ba1 40.35(8) 2_644 2_644 ?
O1W Ba1 Ba1 96.95(9) . 2_644 ?
O1 Ba1 Ba1 79.08(8) . 2_644 ?
O4 Ba1 Ba1 94.85(8) 3_665 2_644 ?
O2 Ba1 Ba1 37.29(7) . 2_644 ?
O3 Ba1 Ba1 79.66(8) 4_565 2_644 ?
O4 Ba1 Ba1 41.04(8) 4_565 2_644 ?
C4 Ba1 Ba1 58.36(9) 4_565 2_644 ?
Ba1 Ba1 Ba1 110.69(2) 2_654 2_644 ?
O2 C1 O1 123.4(5) . . ?
O2 C1 C2 119.6(5) . . ?
O1 C1 C2 116.8(5) . . ?
C3 C2 N1 109.8(5) . . ?
C3 C2 C1 131.8(5) . . ?
N1 C2 C1 117.9(5) . . ?
N2 C3 C2 105.0(4) . . ?
N2 C3 C4 118.2(5) . . ?
C2 C3 C4 136.6(5) . . ?
O3 C4 O4 123.9(5) . . ?
O3 C4 C3 121.4(5) . . ?
O4 C4 C3 114.7(5) . . ?
O3 C4 Ba1 61.6(3) . 4_566 ?
O4 C4 Ba1 64.5(3) . 4_566 ?
C3 C4 Ba1 164.3(4) . 4_566 ?
N1 C5 N2 111.1(5) . . ?
N1 C5 C6 124.3(5) . . ?
N2 C5 C6 124.6(5) . . ?
C5 C6 C7 113.0(5) . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C10 C7 C8 117.0(7) . . ?
C10 C7 C6 121.6(6) . . ?
C8 C7 C6 121.4(7) . . ?
C9 C8 C7 118.1(8) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
N3 C9 C8 124.7(8) . . ?
N3 C9 H9 117.6 . . ?
C8 C9 H9 117.6 . . ?
C7 C10 C11 119.9(8) . . ?
C7 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
N3 C11 C10 124.0(9) . . ?
N3 C11 H11 118.0 . . ?
C10 C11 H11 118.0 . . ?
C5 N1 C2 105.6(5) . . ?
C5 N2 C3 108.5(5) . . ?
C5 N2 H2 125.8 . . ?
C3 N2 H2 125.8 . . ?
C9 N3 C11 116.3(8) . . ?
C1 O1 Ba1 120.6(3) . 2_654 ?
C1 O1 Ba1 96.1(3) . . ?
Ba1 O1 Ba1 100.01(12) 2_654 . ?
C1 O2 Ba1 143.4(4) . 2_644 ?
C1 O2 Ba1 94.5(3) . . ?
Ba1 O2 Ba1 102.01(12) 2_644 . ?
C4 O3 Ba1 154.0(3) . 2_644 ?
C4 O3 Ba1 96.1(3) . 4_566 ?
Ba1 O3 Ba1 108.94(13) 2_644 4_566 ?
C4 O4 Ba1 131.7(3) . 3_665 ?
C4 O4 Ba1 92.7(3) . 4_566 ?
Ba1 O4 Ba1 95.91(12) 3_665 4_566 ?
Ba1 O1W H1WA 95.8 . . ?
Ba1 O1W H1WB 123.0 . . ?
H1WA O1W H1WB 107.7 . . ?

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
O2 C1 C2 C3 2.1(9) . . . . ?
O1 C1 C2 C3 177.7(6) . . . . ?
O2 C1 C2 N1 -168.4(5) . . . . ?
O1 C1 C2 N1 7.2(7) . . . . ?
N1 C2 C3 N2 0.1(6) . . . . ?
C1 C2 C3 N2 -171.0(5) . . . . ?
N1 C2 C3 C4 174.4(6) . . . . ?
C1 C2 C3 C4 3.3(11) . . . . ?
N2 C3 C4 O3 -169.7(5) . . . . ?
C2 C3 C4 O3 16.5(10) . . . . ?
N2 C3 C4 O4 10.2(7) . . . . ?
C2 C3 C4 O4 -163.6(6) . . . . ?
N2 C3 C4 Ba1 93.8(13) . . . 4_566 ?
C2 C3 C4 Ba1 -80.0(15) . . . 4_566 ?
N1 C5 C6 C7 -111.2(7) . . . . ?
N2 C5 C6 C7 71.9(8) . . . . ?
C5 C6 C7 C10 87.7(8) . . . . ?
C5 C6 C7 C8 -94.3(7) . . . . ?
C10 C7 C8 C9 -1.8(11) . . . . ?
C6 C7 C8 C9 -179.9(7) . . . . ?
C7 C8 C9 N3 0.9(13) . . . . ?
C8 C7 C10 C11 0.6(12) . . . . ?
C6 C7 C10 C11 178.7(7) . . . . ?
C7 C10 C11 N3 1.8(14) . . . . ?
N2 C5 N1 C2 0.7(7) . . . . ?
C6 C5 N1 C2 -176.6(5) . . . . ?
C3 C2 N1 C5 -0.5(6) . . . . ?
C1 C2 N1 C5 172.1(5) . . . . ?
N1 C5 N2 C3 -0.6(7) . . . . ?
C6 C5 N2 C3 176.6(5) . . . . ?
C2 C3 N2 C5 0.3(6) . . . . ?
C4 C3 N2 C5 -175.3(5) . . . . ?
C8 C9 N3 C11 1.3(14) . . . . ?
C10 C11 N3 C9 -2.7(14) . . . . ?
O2 C1 O1 Ba1 106.3(5) . . . 2_654 ?
C2 C1 O1 Ba1 -69.1(6) . . . 2_654 ?
O2 C1 O1 Ba1 0.8(6) . . . . ?
C2 C1 O1 Ba1 -174.6(4) . . . . ?
O1 C1 O2 Ba1 116.4(6) . . . 2_644 ?
C2 C1 O2 Ba1 -68.4(7) . . . 2_644 ?
O1 C1 O2 Ba1 -0.8(6) . . . . ?
C2 C1 O2 Ba1 174.5(4) . . . . ?
O4 C4 O3 Ba1 -177.5(6) . . . 2_644 ?
C3 C4 O3 Ba1 2.4(12) . . . 2_644 ?
Ba1 C4 O3 Ba1 164.6(9) 4_566 . . 2_644 ?
O4 C4 O3 Ba1 17.9(6) . . . 4_566 ?
C3 C4 O3 Ba1 -162.3(4) . . . 4_566 ?
O3 C4 O4 Ba1 -117.8(5) . . . 3_665 ?
C3 C4 O4 Ba1 62.3(6) . . . 3_665 ?
Ba1 C4 O4 Ba1 -100.4(4) 4_566 . . 3_665 ?
O3 C4 O4 Ba1 -17.4(6) . . . 4_566 ?
C3 C4 O4 Ba1 162.7(4) . . . 4_566 ?

_refine_diff_density_max         1.594
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.151

