# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1833035'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-05-17 downloaded from the CCDC.
;
_audit_creation_date             2016-12-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 Cl2 N6 O8'
_chemical_formula_sum            'C22 H24 Cl2 N6 O8'
_chemical_formula_weight         571.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.0185(10)
_cell_length_b                   11.602(2)
_cell_length_c                   13.015(3)
_cell_angle_alpha                70.854(3)
_cell_angle_beta                 81.101(2)
_cell_angle_gamma                89.578(3)
_cell_volume                     1269.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3731
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4797
_cell_measurement_theta_min      1.8602
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11556
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_min         2.288
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 98.1000
_diffrn_measured_fraction_theta_max 27.4797
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9054
	          2theta: -19.7635
scan:
	Number of images: 270
	           Slice: -110.0000 - 25.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.9054
	          2theta: -19.7635
scan:
	Number of images: 196
	           Slice: -35.0000 - 63.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 44.9054
	          2theta: -19.7635
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             5684
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0195
_diffrn_orient_matrix_UB_12      0.1046
_diffrn_orient_matrix_UB_13      -0.0361
_diffrn_orient_matrix_UB_21      -0.0288
_diffrn_orient_matrix_UB_22      0.0276
_diffrn_orient_matrix_UB_23      0.0822
_diffrn_orient_matrix_UB_31      0.0614
_diffrn_orient_matrix_UB_32      0.0391
_diffrn_orient_matrix_UB_33      0.0387
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710747
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5024
_reflns_number_total             5684
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5684
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0285P)²+0.8471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1002
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,
 H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B),
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.68050(5) 0.43688(5) 0.38648(4) 0.03081(12) Uani 1 1 d . . . . .
Cl2 Cl 0.55067(6) 1.17887(5) 0.31948(5) 0.03752(14) Uani 1 1 d . . . . .
O1 O 0.13356(15) 0.45446(11) 0.40995(12) 0.0280(3) Uani 1 1 d . . . . .
O2 O 0.31668(15) 0.87444(11) 0.21232(11) 0.0239(3) Uani 1 1 d . . . . .
O3 O 0.13186(15) 0.91329(11) 0.54837(11) 0.0241(3) Uani 1 1 d . . . . .
O4 O 0.07731(15) 0.71911(12) 0.74940(11) 0.0292(3) Uani 1 1 d . . . . .
O5 O 0.20591(16) 0.51444(13) 0.88974(12) 0.0321(3) Uani 1 1 d . . . . .
O6 O 0.27029(17) 0.26580(13) 0.98385(12) 0.0351(3) Uani 1 1 d . . . . .
O7 O 0.17851(16) 0.06905(13) 0.90614(12) 0.0328(3) Uani 1 1 d . . . . .
O8 O 0.32340(15) 0.15488(12) 0.66891(11) 0.0283(3) Uani 1 1 d . . . . .
N1 N 0.39240(18) 0.44561(14) 0.39579(13) 0.0242(3) Uani 1 1 d . . . . .
N2 N 0.48554(18) 0.29119(14) 0.53983(13) 0.0249(3) Uani 1 1 d . . . . .
N3 N 0.22124(17) 0.30313(14) 0.53765(13) 0.0239(3) Uani 1 1 d . . . . .
N4 N 0.32529(18) 1.03505(14) 0.44046(13) 0.0251(3) Uani 1 1 d . . . . .
N5 N 0.21202(17) 0.88679(13) 0.38159(13) 0.0212(3) Uani 1 1 d . . . . .
N6 N 0.41926(17) 1.01507(13) 0.26567(13) 0.0231(3) Uani 1 1 d . . . . .
C1 C 0.1416(2) 0.56551(16) 0.32238(16) 0.0231(4) Uani 1 1 d . . . . .
C2 C 0.0419(2) 0.57235(17) 0.24992(16) 0.0243(4) Uani 1 1 d . . . . .
H2 H -0.0184 0.5046 0.2572 0.029 Uiso 1 1 calc R . . . .
C3 C 0.0337(2) 0.68167(18) 0.16661(16) 0.0259(4) Uani 1 1 d . . . . .
H3 H -0.0336 0.6875 0.1179 0.031 Uiso 1 1 calc R . . . .
C4 C 0.1246(2) 0.78296(17) 0.15475(16) 0.0246(4) Uani 1 1 d . . . . .
H4 H 0.1206 0.8561 0.0979 0.029 Uiso 1 1 calc R . . . .
C5 C 0.2205(2) 0.77192(16) 0.22961(15) 0.0211(4) Uani 1 1 d . . . . .
C6 C 0.2326(2) 0.66470(16) 0.31490(16) 0.0230(4) Uani 1 1 d . . . . .
H6 H 0.2983 0.6596 0.3645 0.028 Uiso 1 1 calc R . . . .
C7 C 0.3141(2) 0.92555(15) 0.29173(15) 0.0209(4) Uani 1 1 d . . . . .
C8 C 0.4162(2) 1.06338(16) 0.34473(16) 0.0234(4) Uani 1 1 d . . . . .
C9 C 0.2250(2) 0.94412(16) 0.45332(15) 0.0213(4) Uani 1 1 d . . . . .
C10 C 0.0219(2) 0.81346(16) 0.57107(16) 0.0241(4) Uani 1 1 d . . . . .
H10A H 0.0689 0.7458 0.5525 0.029 Uiso 1 1 calc R . . . .
H10B H -0.0583 0.8402 0.5281 0.029 Uiso 1 1 calc R . . . .
C11 C -0.0386(2) 0.77532(17) 0.69169(16) 0.0267(4) Uani 1 1 d . . . . .
H11A H -0.0704 0.8460 0.7121 0.032 Uiso 1 1 calc R . . . .
H11B H -0.1244 0.7185 0.7094 0.032 Uiso 1 1 calc R . . . .
C12 C 0.0327(2) 0.67323(18) 0.86554(16) 0.0312(5) Uani 1 1 d . . . . .
H12A H -0.0469 0.6105 0.8849 0.037 Uiso 1 1 calc R . . . .
H12B H -0.0044 0.7385 0.8924 0.037 Uiso 1 1 calc R . . . .
C13 C 0.1668(3) 0.62112(18) 0.91613(17) 0.0341(5) Uani 1 1 d . . . . .
H13A H 0.2506 0.6809 0.8885 0.041 Uiso 1 1 calc R . . . .
H13B H 0.1442 0.6012 0.9955 0.041 Uiso 1 1 calc R . . . .
C14 C 0.3484(3) 0.4753(2) 0.9167(2) 0.0447(6) Uani 1 1 d . . . . .
H14A H 0.3527 0.4702 0.9921 0.054 Uiso 1 1 calc R . . . .
H14B H 0.4264 0.5340 0.8686 0.054 Uiso 1 1 calc R . . . .
C15 C 0.3745(3) 0.3527(2) 0.9039(2) 0.0431(6) Uani 1 1 d . . . . .
H15A H 0.3613 0.3556 0.8305 0.052 Uiso 1 1 calc R . . . .
H15B H 0.4763 0.3298 0.9140 0.052 Uiso 1 1 calc R . . . .
C16 C 0.3177(3) 0.14406(19) 1.01355(18) 0.0366(5) Uani 1 1 d . . . . .
H16A H 0.2488 0.0943 1.0774 0.044 Uiso 1 1 calc R . . . .
H16B H 0.4160 0.1430 1.0352 0.044 Uiso 1 1 calc R . . . .
C17 C 0.3265(2) 0.0865(2) 0.9250(2) 0.0370(5) Uani 1 1 d . . . . .
H17A H 0.3867 0.1390 0.8577 0.044 Uiso 1 1 calc R . . . .
H17B H 0.3734 0.0086 0.9479 0.044 Uiso 1 1 calc R . . . .
C18 C 0.1729(2) 0.01074(18) 0.82615(17) 0.0315(4) Uani 1 1 d . . . . .
H18A H 0.0831 -0.0426 0.8479 0.038 Uiso 1 1 calc R . . . .
H18B H 0.2590 -0.0398 0.8251 0.038 Uiso 1 1 calc R . . . .
C19 C 0.1726(2) 0.09876(18) 0.71153(17) 0.0289(4) Uani 1 1 d . . . . .
H19A H 0.1442 0.0558 0.6644 0.035 Uiso 1 1 calc R . . . .
H19B H 0.1008 0.1610 0.7134 0.035 Uiso 1 1 calc R . . . .
C20 C 0.3401(2) 0.25251(16) 0.57940(15) 0.0230(4) Uani 1 1 d . . . . .
C21 C 0.4992(2) 0.38484(16) 0.44841(16) 0.0231(4) Uani 1 1 d . . . . .
C22 C 0.2555(2) 0.40113(16) 0.44796(16) 0.0233(4) 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
Cl1 C21 1.7249(19) . ?
Cl2 C8 1.7279(18) . ?
O1 C1 1.406(2) . ?
O1 C22 1.339(2) . ?
O2 C5 1.413(2) . ?
O2 C7 1.347(2) . ?
O3 C9 1.326(2) . ?
O3 C10 1.454(2) . ?
O4 C11 1.412(2) . ?
O4 C12 1.420(2) . ?
O5 C13 1.417(2) . ?
O5 C14 1.417(3) . ?
O6 C15 1.416(3) . ?
O6 C16 1.418(2) . ?
O7 C17 1.422(3) . ?
O7 C18 1.422(2) . ?
O8 C19 1.458(2) . ?
O8 C20 1.321(2) . ?
N1 C21 1.331(2) . ?
N1 C22 1.331(2) . ?
N2 C20 1.354(2) . ?
N2 C21 1.311(2) . ?
N3 C20 1.323(2) . ?
N3 C22 1.332(2) . ?
N4 C8 1.324(2) . ?
N4 C9 1.345(2) . ?
N5 C7 1.321(2) . ?
N5 C9 1.330(2) . ?
N6 C7 1.333(2) . ?
N6 C8 1.320(2) . ?
C1 C2 1.384(3) . ?
C1 C6 1.386(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(3) . ?
C5 C6 1.386(3) . ?
C6 H6 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.497(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.495(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.499(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.502(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.507(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 O1 C1 122.75(15) . . ?
C7 O2 C5 120.12(14) . . ?
C9 O3 C10 117.50(14) . . ?
C11 O4 C12 113.63(15) . . ?
C14 O5 C13 111.65(17) . . ?
C15 O6 C16 114.52(17) . . ?
C17 O7 C18 113.53(16) . . ?
C20 O8 C19 117.46(15) . . ?
C21 N1 C22 111.88(16) . . ?
C21 N2 C20 111.91(16) . . ?
C20 N3 C22 113.53(16) . . ?
C8 N4 C9 111.78(16) . . ?
C7 N5 C9 112.94(15) . . ?
C8 N6 C7 111.73(16) . . ?
C2 C1 O1 115.01(16) . . ?
C2 C1 C6 122.32(17) . . ?
C6 C1 O1 122.41(16) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.84(17) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.85(17) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.09(17) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 O2 116.79(16) . . ?
C4 C5 C6 123.34(17) . . ?
C6 C5 O2 119.75(16) . . ?
C1 C6 H6 121.7 . . ?
C5 C6 C1 116.56(17) . . ?
C5 C6 H6 121.7 . . ?
N5 C7 O2 119.73(16) . . ?
N5 C7 N6 127.77(17) . . ?
N6 C7 O2 112.48(16) . . ?
N4 C8 Cl2 115.84(14) . . ?
N6 C8 Cl2 115.18(14) . . ?
N6 C8 N4 128.98(17) . . ?
O3 C9 N4 113.49(16) . . ?
O3 C9 N5 119.75(16) . . ?
N5 C9 N4 126.76(17) . . ?
O3 C10 H10A 110.4 . . ?
O3 C10 H10B 110.4 . . ?
O3 C10 C11 106.56(15) . . ?
H10A C10 H10B 108.6 . . ?
C11 C10 H10A 110.4 . . ?
C11 C10 H10B 110.4 . . ?
O4 C11 C10 107.70(15) . . ?
O4 C11 H11A 110.2 . . ?
O4 C11 H11B 110.2 . . ?
C10 C11 H11A 110.2 . . ?
C10 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
O4 C12 H12A 110.1 . . ?
O4 C12 H12B 110.1 . . ?
O4 C12 C13 107.98(17) . . ?
H12A C12 H12B 108.4 . . ?
C13 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
O5 C13 C12 109.53(17) . . ?
O5 C13 H13A 109.8 . . ?
O5 C13 H13B 109.8 . . ?
C12 C13 H13A 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
O5 C14 H14A 109.7 . . ?
O5 C14 H14B 109.7 . . ?
O5 C14 C15 109.70(19) . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
O6 C15 C14 108.66(19) . . ?
O6 C15 H15A 110.0 . . ?
O6 C15 H15B 110.0 . . ?
C14 C15 H15A 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.3 . . ?
O6 C16 H16A 108.5 . . ?
O6 C16 H16B 108.5 . . ?
O6 C16 C17 115.20(18) . . ?
H16A C16 H16B 107.5 . . ?
C17 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
O7 C17 C16 108.68(18) . . ?
O7 C17 H17A 110.0 . . ?
O7 C17 H17B 110.0 . . ?
C16 C17 H17A 110.0 . . ?
C16 C17 H17B 110.0 . . ?
H17A C17 H17B 108.3 . . ?
O7 C18 H18A 108.9 . . ?
O7 C18 H18B 108.9 . . ?
O7 C18 C19 113.55(16) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
O8 C19 C18 108.04(16) . . ?
O8 C19 H19A 110.1 . . ?
O8 C19 H19B 110.1 . . ?
C18 C19 H19A 110.1 . . ?
C18 C19 H19B 110.1 . . ?
H19A C19 H19B 108.4 . . ?
O8 C20 N2 113.25(16) . . ?
O8 C20 N3 120.31(17) . . ?
N3 C20 N2 126.43(17) . . ?
N1 C21 Cl1 114.94(14) . . ?
N2 C21 Cl1 115.98(14) . . ?
N2 C21 N1 129.08(18) . . ?
N1 C22 O1 120.37(17) . . ?
N1 C22 N3 126.95(17) . . ?
N3 C22 O1 112.66(16) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mx6601a
_database_code_depnum_ccdc_archive 'CCDC 1833036'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-05-17 downloaded from the CCDC.
;
_audit_creation_date             2017-12-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 Cl2 N6 O8'
_chemical_formula_sum            'C22 H24 Cl2 N6 O8'
_chemical_formula_weight         571.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.245(2)
_cell_length_b                   17.678(3)
_cell_length_c                   13.048(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.709(2)
_cell_angle_gamma                90
_cell_volume                     2580.7(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3968
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4836
_cell_measurement_theta_min      1.5685
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.922
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.102
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10750
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.154
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2841
_reflns_number_total             2953
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2953
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+3.4937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1184
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6B,H6A), C7(H7B,H7A), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.92278(5) 0.43214(3) 0.55111(4) 0.04251(17) Uani 1 1 d . . . . .
O1 O 0.54686(12) 0.33209(8) 0.40039(10) 0.0331(3) Uani 1 1 d . . . . .
N1 N 0.80435(13) 0.32715(8) 0.63408(11) 0.0260(3) Uani 1 1 d . . . . .
C1 C 0.70609(14) 0.28433(9) 0.63104(12) 0.0227(3) Uani 1 1 d . . . . .
C2 C 0.80046(15) 0.37312(10) 0.55382(14) 0.0270(4) Uani 1 1 d . . . . .
N2 N 0.71726(13) 0.38002(8) 0.47582(12) 0.0288(3) Uani 1 1 d . . . . .
O2 O 0.34900(13) 0.34710(9) 0.52610(11) 0.0423(4) Uani 1 1 d . . . . .
O3 O 0.37330(14) 0.41683(8) 0.72338(11) 0.0391(3) Uani 1 1 d . . . . .
N3 N 0.61665(12) 0.28162(8) 0.55735(11) 0.0237(3) Uani 1 1 d . . . . .
C3 C 0.62746(15) 0.33047(10) 0.48136(13) 0.0257(4) Uani 1 1 d . . . . .
O4 O 0.70529(10) 0.23831(7) 0.71230(9) 0.0266(3) Uani 1 1 d . . . . .
C4 C 0.44326(17) 0.28201(13) 0.39725(15) 0.0354(4) Uani 1 1 d . . . . .
H4A H 0.458959 0.240862 0.448265 0.043 Uiso 1 1 calc R . . . .
H4B H 0.428339 0.258903 0.328046 0.043 Uiso 1 1 calc R . . . .
C5 C 0.33615(19) 0.32620(15) 0.42102(16) 0.0432(5) Uani 1 1 d . . . . .
H5A H 0.328039 0.372064 0.377347 0.052 Uiso 1 1 calc R . . . .
H5B H 0.263196 0.295167 0.406054 0.052 Uiso 1 1 calc R . . . .
C6 C 0.2770(2) 0.41003(14) 0.54491(18) 0.0442(5) Uani 1 1 d . . . . .
H6B H 0.196989 0.404065 0.506608 0.053 Uiso 1 1 calc R . . . .
H6A H 0.313592 0.456727 0.520334 0.053 Uiso 1 1 calc R . . . .
C7 C 0.2647(2) 0.41656(13) 0.65729(17) 0.0422(5) Uani 1 1 d . . . . .
H7B H 0.220845 0.463843 0.669034 0.051 Uiso 1 1 calc R . . . .
H7A H 0.214987 0.373899 0.677560 0.051 Uiso 1 1 calc R . . . .
C8 C 0.4486(2) 0.47907(12) 0.7079(2) 0.0521(6) Uani 1 1 d . . . . .
H8A H 0.403057 0.526872 0.709918 0.063 Uiso 1 1 calc R . . . .
H8B H 0.479612 0.475027 0.639722 0.063 Uiso 1 1 calc R . . . .
C9 C 0.59833(14) 0.19981(10) 0.72745(12) 0.0229(3) Uani 1 1 d . . . . .
C10 C 0.60069(16) 0.12185(10) 0.72607(13) 0.0279(4) Uani 1 1 d . . . . .
H10 H 0.669677 0.095451 0.709129 0.033 Uiso 1 1 calc R . . . .
C11 C 0.500000 0.08282(14) 0.750000 0.0317(5) Uani 1 2 d S T P . .
H11 H 0.500000 0.029079 0.749998 0.038 Uiso 1 2 calc RS T P . .
C12 C 0.500000 0.24114(13) 0.750000 0.0231(5) Uani 1 2 d S T P . .
H12 H 0.500001 0.294878 0.749998 0.028 Uiso 1 2 calc RS T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.7296(18) . ?
O1 C3 1.322(2) . ?
O1 C4 1.460(2) . ?
N1 C1 1.337(2) . ?
N1 C2 1.323(2) . ?
C1 N3 1.321(2) . ?
C1 O4 1.337(2) . ?
C2 N2 1.318(2) . ?
N2 C3 1.344(2) . ?
O2 C5 1.413(3) . ?
O2 C6 1.412(3) . ?
O3 C7 1.423(3) . ?
O3 C8 1.415(3) . ?
N3 C3 1.329(2) . ?
O4 C9 1.4128(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.494(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 C7 1.491(3) . ?
C7 H7B 0.9900 . ?
C7 H7A 0.9900 . ?
C8 C8 1.512(5) 2_656 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.379(2) . ?
C9 C12 1.381(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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
C3 O1 C4 119.40(14) . . ?
C2 N1 C1 111.24(15) . . ?
N1 C1 O4 113.07(14) . . ?
N3 C1 N1 127.53(15) . . ?
N3 C1 O4 119.35(15) . . ?
N1 C2 Cl1 115.03(14) . . ?
N2 C2 Cl1 115.68(13) . . ?
N2 C2 N1 129.29(16) . . ?
C2 N2 C3 112.18(15) . . ?
C6 O2 C5 111.69(16) . . ?
C8 O3 C7 113.96(17) . . ?
C1 N3 C3 113.55(15) . . ?
O1 C3 N2 113.69(15) . . ?
O1 C3 N3 120.24(16) . . ?
N3 C3 N2 126.04(16) . . ?
C1 O4 C9 118.49(13) . . ?
O1 C4 H4A 109.8 . . ?
O1 C4 H4B 109.8 . . ?
O1 C4 C5 109.55(18) . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 H4A 109.8 . . ?
C5 C4 H4B 109.8 . . ?
O2 C5 C4 109.35(16) . . ?
O2 C5 H5A 109.8 . . ?
O2 C5 H5B 109.8 . . ?
C4 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
O2 C6 H6B 109.7 . . ?
O2 C6 H6A 109.7 . . ?
O2 C6 C7 110.05(18) . . ?
H6B C6 H6A 108.2 . . ?
C7 C6 H6B 109.7 . . ?
C7 C6 H6A 109.7 . . ?
O3 C7 C6 115.99(18) . . ?
O3 C7 H7B 108.3 . . ?
O3 C7 H7A 108.3 . . ?
C6 C7 H7B 108.3 . . ?
C6 C7 H7A 108.3 . . ?
H7B C7 H7A 107.4 . . ?
O3 C8 C8 108.75(19) . 2_656 ?
O3 C8 H8A 109.9 . . ?
O3 C8 H8B 109.9 . . ?
C8 C8 H8A 109.9 2_656 . ?
C8 C8 H8B 109.9 2_656 . ?
H8A C8 H8B 108.3 . . ?
C10 C9 O4 117.52(15) . . ?
C10 C9 C12 123.26(16) . . ?
C12 C9 O4 119.06(15) . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C11 118.48(17) . . ?
C11 C10 H10 120.8 . . ?
C10 C11 C10 120.4(2) . 2_656 ?
C10 C11 H11 119.8 . . ?
C10 C11 H11 119.8 2_656 . ?
C9 C12 C9 116.1(2) 2_656 . ?
C9 C12 H12 121.9 . . ?
C9 C12 H12 121.9 2_656 . ?

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
Cl1 C2 N2 C3 177.66(12) . . . . ?
O1 C4 C5 O2 -70.2(2) . . . . ?
N1 C1 N3 C3 -3.1(2) . . . . ?
N1 C1 O4 C9 169.25(14) . . . . ?
N1 C2 N2 C3 -2.0(3) . . . . ?
C1 N1 C2 Cl1 179.16(12) . . . . ?
C1 N1 C2 N2 -1.2(3) . . . . ?
C1 N3 C3 O1 177.40(15) . . . . ?
C1 N3 C3 N2 -0.9(2) . . . . ?
C1 O4 C9 C10 118.83(17) . . . . ?
C1 O4 C9 C12 -65.72(18) . . . . ?
C2 N1 C1 N3 4.0(2) . . . . ?
C2 N1 C1 O4 -178.47(14) . . . . ?
C2 N2 C3 O1 -175.27(15) . . . . ?
C2 N2 C3 N3 3.1(2) . . . . ?
O2 C6 C7 O3 52.4(3) . . . . ?
N3 C1 O4 C9 -13.0(2) . . . . ?
C3 O1 C4 C5 102.95(19) . . . . ?
O4 C1 N3 C3 179.51(14) . . . . ?
O4 C9 C10 C11 174.25(12) . . . . ?
O4 C9 C12 C9 -174.66(16) . . . 2_656 ?
C4 O1 C3 N2 -178.91(15) . . . . ?
C4 O1 C3 N3 2.6(2) . . . . ?
C5 O2 C6 C7 163.52(19) . . . . ?
C6 O2 C5 C4 158.20(19) . . . . ?
C7 O3 C8 C8 171.9(2) . . . 2_656 ?
C8 O3 C7 C6 63.0(3) . . . . ?
C9 C10 C11 C10 0.47(11) . . . 2_656 ?
C10 C9 C12 C9 0.51(12) . . . 2_656 ?
C12 C9 C10 C11 -1.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mx6282e
_database_code_depnum_ccdc_archive 'CCDC 1833037'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-05-17 downloaded from the CCDC.
;
_audit_creation_date             2017-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H28 Br2 Ca Cl2 N6 O9, H2 O'
_chemical_formula_sum            'C23 H30 Br2 Ca Cl2 N6 O10'
_chemical_formula_weight         821.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.081(4)
_cell_length_b                   7.8133(15)
_cell_length_c                   23.448(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.521(2)
_cell_angle_gamma                90
_cell_volume                     3220.7(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9821
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4838
_cell_measurement_theta_min      1.1583
_shelx_estimated_absorpt_T_max   0.675
_shelx_estimated_absorpt_T_min   0.552
_exptl_absorpt_coefficient_mu    2.903
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.147
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            21205
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         1.888
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6680
_reflns_number_total             7261
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.189
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         7261
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+2.8904P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0903
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O9-H9
 0.85 with sigma of 0.01
 C23-H9
 1.891852 with sigma of 0.02
 Ca1-H9
 2.823801 with sigma of 0.02
3.a Free rotating group:
 O10(H10C,H10D)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B),
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C20(H20), C22(H22)
3.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.74540(2) 0.61935(3) 0.67532(2) 0.03257(8) Uani 1 1 d . . . . .
Br2 Br 0.53592(2) 1.17657(3) 0.64049(2) 0.03449(8) Uani 1 1 d . . . . .
Ca1 Ca 0.64007(3) 0.89612(6) 0.65280(2) 0.02375(11) Uani 1 1 d D . . . .
Cl1 Cl 0.71696(5) 0.08395(9) 0.38997(3) 0.04189(17) Uani 1 1 d . . . . .
Cl2 Cl 0.87769(5) 0.71436(11) 0.91154(3) 0.04893(19) Uani 1 1 d . . . . .
O1 O 0.90757(11) 0.3713(3) 0.53829(8) 0.0395(5) Uani 1 1 d . . . . .
O2 O 0.67735(11) 0.6345(3) 0.46845(8) 0.0355(4) Uani 1 1 d . . . . .
O3 O 0.59282(11) 0.8525(2) 0.54519(7) 0.0319(4) Uani 1 1 d . . . . .
O4 O 0.54018(10) 0.6865(2) 0.62718(8) 0.0313(4) Uani 1 1 d . . . . .
O5 O 0.59677(11) 0.7928(2) 0.73775(8) 0.0326(4) Uani 1 1 d . . . . .
O6 O 0.70493(10) 1.0329(2) 0.74514(7) 0.0282(4) Uani 1 1 d . . . . .
O7 O 0.85766(11) 1.1241(2) 0.75120(8) 0.0337(4) Uani 1 1 d . . . . .
O8 O 0.94864(11) 0.5934(2) 0.73076(7) 0.0310(4) Uani 1 1 d . . . . .
O9 O 0.73253(12) 1.0498(3) 0.61621(9) 0.0409(5) Uani 1 1 d D . . . .
H9 H 0.7180(12) 1.151(2) 0.6055(16) 0.061 Uiso 1 1 d DR . . . .
N1 N 0.81760(13) 0.2420(3) 0.46987(9) 0.0352(5) Uani 1 1 d . . . . .
N2 N 0.69842(13) 0.3785(3) 0.43392(9) 0.0335(5) Uani 1 1 d . . . . .
N3 N 0.79495(12) 0.5165(3) 0.50670(9) 0.0301(5) Uani 1 1 d . . . . .
N4 N 0.86433(12) 0.9299(3) 0.82620(9) 0.0323(5) Uani 1 1 d . . . . .
N5 N 0.91652(13) 0.6571(3) 0.81392(9) 0.0318(5) Uani 1 1 d . . . . .
N6 N 0.90546(12) 0.8678(3) 0.73906(9) 0.0278(4) Uani 1 1 d . . . . .
C1 C 0.83689(15) 0.3799(4) 0.50401(10) 0.0315(5) Uani 1 1 d . . . . .
C2 C 0.74823(16) 0.2549(4) 0.43687(10) 0.0328(6) Uani 1 1 d . . . . .
C3 C 0.72569(15) 0.5071(3) 0.47053(10) 0.0297(5) Uani 1 1 d . . . . .
C4 C 0.70273(15) 0.7810(4) 0.50535(11) 0.0323(5) Uani 1 1 d . . . . .
H4A H 0.742951 0.842926 0.491433 0.039 Uiso 1 1 calc R . . . .
H4B H 0.723823 0.743845 0.546286 0.039 Uiso 1 1 calc R . . . .
C5 C 0.63485(16) 0.8964(3) 0.50235(10) 0.0326(6) Uani 1 1 d . . . . .
H5A H 0.652513 1.016328 0.508629 0.039 Uiso 1 1 calc R . . . .
H5B H 0.600764 0.888546 0.462700 0.039 Uiso 1 1 calc R . . . .
C6 C 0.54046(16) 0.7140(4) 0.52728(12) 0.0380(6) Uani 1 1 d . . . . .
H6A H 0.568483 0.605162 0.527183 0.046 Uiso 1 1 calc R . . . .
H6B H 0.509210 0.734716 0.487209 0.046 Uiso 1 1 calc R . . . .
C7 C 0.49089(16) 0.7042(4) 0.56993(12) 0.0385(6) Uani 1 1 d . . . . .
H7A H 0.459840 0.809356 0.567863 0.046 Uiso 1 1 calc R . . . .
H7B H 0.456236 0.604637 0.560952 0.046 Uiso 1 1 calc R . . . .
C8 C 0.50094(16) 0.6421(4) 0.67139(13) 0.0380(6) Uani 1 1 d . . . . .
H8A H 0.474031 0.531757 0.661787 0.046 Uiso 1 1 calc R . . . .
H8B H 0.463097 0.731363 0.674263 0.046 Uiso 1 1 calc R . . . .
C9 C 0.55934(17) 0.6284(4) 0.72791(13) 0.0382(6) Uani 1 1 d . . . . .
H9A H 0.534915 0.600541 0.760400 0.046 Uiso 1 1 calc R . . . .
H9B H 0.596548 0.537357 0.725413 0.046 Uiso 1 1 calc R . . . .
C10 C 0.65420(17) 0.8040(4) 0.79092(11) 0.0383(6) Uani 1 1 d . . . . .
H10A H 0.696859 0.725979 0.789447 0.046 Uiso 1 1 calc R . . . .
H10B H 0.633114 0.771178 0.824713 0.046 Uiso 1 1 calc R . . . .
C11 C 0.68144(16) 0.9858(4) 0.79719(11) 0.0375(6) Uani 1 1 d . . . . .
H11A H 0.639980 1.062156 0.802737 0.045 Uiso 1 1 calc R . . . .
H11B H 0.724625 0.997033 0.831813 0.045 Uiso 1 1 calc R . . . .
C12 C 0.72861(16) 1.2080(3) 0.74521(12) 0.0340(6) Uani 1 1 d . . . . .
H12A H 0.695147 1.279684 0.763316 0.041 Uiso 1 1 calc R . . . .
H12B H 0.722858 1.246883 0.704216 0.041 Uiso 1 1 calc R . . . .
C13 C 0.81032(16) 1.2329(4) 0.77838(12) 0.0365(6) Uani 1 1 d . . . . .
H13A H 0.825315 1.354280 0.776492 0.044 Uiso 1 1 calc R . . . .
H13B H 0.816392 1.201046 0.820085 0.044 Uiso 1 1 calc R . . . .
C14 C 0.87553(14) 0.9696(3) 0.77357(11) 0.0289(5) Uani 1 1 d . . . . .
C15 C 0.88740(15) 0.7737(4) 0.84255(11) 0.0319(5) Uani 1 1 d . . . . .
C16 C 0.92215(14) 0.7147(3) 0.76127(10) 0.0278(5) Uani 1 1 d . . . . .
C17 C 0.95525(14) 0.6223(3) 0.67311(11) 0.0283(5) Uani 1 1 d . . . . .
C18 C 0.99511(16) 0.7571(4) 0.65764(12) 0.0369(6) Uani 1 1 d . . . . .
H18 H 1.015876 0.843423 0.685302 0.044 Uiso 1 1 calc R . . . .
C19 C 1.00430(19) 0.7643(4) 0.60059(13) 0.0456(7) Uani 1 1 d . . . . .
H19 H 1.031886 0.856458 0.589140 0.055 Uiso 1 1 calc R . . . .
C20 C 0.97400(18) 0.6395(4) 0.56020(12) 0.0415(7) Uani 1 1 d . . . . .
H20 H 0.980546 0.644579 0.521201 0.050 Uiso 1 1 calc R . . . .
C21 C 0.93410(15) 0.5076(4) 0.57778(11) 0.0335(6) Uani 1 1 d . . . . .
C22 C 0.92388(14) 0.4947(3) 0.63379(11) 0.0306(5) Uani 1 1 d . . . . .
H22 H 0.896429 0.402163 0.645149 0.037 Uiso 1 1 calc R . . . .
C23 C 0.80862(19) 1.0286(4) 0.61154(13) 0.0482(8) Uani 1 1 d D . . . .
H23A H 0.812216 1.055225 0.571430 0.072 Uiso 1 1 calc GR . . . .
H23B H 0.824533 0.909981 0.620879 0.072 Uiso 1 1 calc GR . . . .
H23C H 0.841798 1.105937 0.639059 0.072 Uiso 1 1 calc GR . . . .
O10 O 0.66268(17) 1.3515(3) 0.57300(11) 0.0555(6) Uani 1 1 d . . . . .
H10C H 0.686267 1.430548 0.594797 0.083 Uiso 1 1 d G . . . .
H10D H 0.623384 1.335543 0.586310 0.083 Uiso 1 1 d G . . . .


_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
Br1 Ca1 2.8481(7) . ?
Br2 Ca1 2.8595(7) . ?
Ca1 O3 2.4909(18) . ?
Ca1 O4 2.4081(19) . ?
Ca1 O5 2.4415(18) . ?
Ca1 O6 2.4530(17) . ?
Ca1 O9 2.376(2) . ?
Cl1 C2 1.739(3) . ?
Cl2 C15 1.731(3) . ?
O1 C1 1.343(3) . ?
O1 C21 1.419(3) . ?
O2 C3 1.318(3) . ?
O2 C4 1.444(3) . ?
O3 C5 1.436(3) . ?
O3 C6 1.435(3) . ?
O4 C7 1.434(3) . ?
O4 C8 1.429(3) . ?
O5 C9 1.446(3) . ?
O5 C10 1.426(3) . ?
O6 C11 1.431(3) . ?
O6 C12 1.434(3) . ?
O7 C13 1.455(3) . ?
O7 C14 1.326(3) . ?
O8 C16 1.342(3) . ?
O8 C17 1.403(3) . ?
O9 H9 0.854(9) . ?
O9 C23 1.415(4) . ?
N1 C1 1.340(3) . ?
N1 C2 1.315(4) . ?
N2 C2 1.311(4) . ?
N2 C3 1.339(3) . ?
N3 C1 1.319(3) . ?
N3 C3 1.340(3) . ?
N4 C14 1.333(3) . ?
N4 C15 1.318(4) . ?
N5 C15 1.313(3) . ?
N5 C16 1.340(3) . ?
N6 C14 1.336(3) . ?
N6 C16 1.312(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.511(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.493(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.493(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.500(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.513(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C17 C18 1.372(4) . ?
C17 C22 1.386(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.380(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.375(4) . ?
C21 C22 1.372(4) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O10 H10C 0.8500 . ?
O10 H10D 0.8494 . ?

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
Br1 Ca1 Br2 175.246(19) . . ?
O3 Ca1 Br1 98.05(5) . . ?
O3 Ca1 Br2 86.61(4) . . ?
O4 Ca1 Br1 87.69(5) . . ?
O4 Ca1 Br2 93.34(5) . . ?
O4 Ca1 O3 66.08(6) . . ?
O4 Ca1 O5 67.29(6) . . ?
O4 Ca1 O6 133.83(6) . . ?
O5 Ca1 Br1 85.75(5) . . ?
O5 Ca1 Br2 90.37(5) . . ?
O5 Ca1 O3 132.98(7) . . ?
O5 Ca1 O6 66.56(6) . . ?
O6 Ca1 Br1 90.35(4) . . ?
O6 Ca1 Br2 85.58(4) . . ?
O6 Ca1 O3 159.01(6) . . ?
O9 Ca1 Br1 87.38(6) . . ?
O9 Ca1 Br2 94.51(6) . . ?
O9 Ca1 O3 78.87(7) . . ?
O9 Ca1 O4 143.49(7) . . ?
O9 Ca1 O5 148.07(7) . . ?
O9 Ca1 O6 82.35(7) . . ?
C1 O1 C21 118.8(2) . . ?
C3 O2 C4 117.5(2) . . ?
C5 O3 Ca1 124.32(15) . . ?
C6 O3 Ca1 116.51(15) . . ?
C6 O3 C5 113.35(19) . . ?
C7 O4 Ca1 115.70(16) . . ?
C8 O4 Ca1 117.03(16) . . ?
C8 O4 C7 113.4(2) . . ?
C9 O5 Ca1 113.02(15) . . ?
C10 O5 Ca1 112.71(15) . . ?
C10 O5 C9 114.3(2) . . ?
C11 O6 Ca1 117.70(15) . . ?
C11 O6 C12 113.1(2) . . ?
C12 O6 Ca1 119.86(14) . . ?
C14 O7 C13 118.2(2) . . ?
C16 O8 C17 121.4(2) . . ?
Ca1 O9 H9 112.3(12) . . ?
C23 O9 Ca1 138.40(19) . . ?
C23 O9 H9 108.9(12) . . ?
C2 N1 C1 111.7(2) . . ?
C2 N2 C3 111.9(2) . . ?
C1 N3 C3 112.8(2) . . ?
C15 N4 C14 112.2(2) . . ?
C15 N5 C16 111.4(2) . . ?
C16 N6 C14 113.0(2) . . ?
N1 C1 O1 113.3(2) . . ?
N3 C1 O1 119.3(2) . . ?
N3 C1 N1 127.4(2) . . ?
N1 C2 Cl1 115.9(2) . . ?
N2 C2 Cl1 114.5(2) . . ?
N2 C2 N1 129.6(3) . . ?
O2 C3 N2 113.7(2) . . ?
O2 C3 N3 119.7(2) . . ?
N2 C3 N3 126.6(2) . . ?
O2 C4 H4A 110.2 . . ?
O2 C4 H4B 110.2 . . ?
O2 C4 C5 107.7(2) . . ?
H4A C4 H4B 108.5 . . ?
C5 C4 H4A 110.2 . . ?
C5 C4 H4B 110.2 . . ?
O3 C5 C4 112.5(2) . . ?
O3 C5 H5A 109.1 . . ?
O3 C5 H5B 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
O3 C6 H6A 110.2 . . ?
O3 C6 H6B 110.2 . . ?
O3 C6 C7 107.5(2) . . ?
H6A C6 H6B 108.5 . . ?
C7 C6 H6A 110.2 . . ?
C7 C6 H6B 110.2 . . ?
O4 C7 C6 107.0(2) . . ?
O4 C7 H7A 110.3 . . ?
O4 C7 H7B 110.3 . . ?
C6 C7 H7A 110.3 . . ?
C6 C7 H7B 110.3 . . ?
H7A C7 H7B 108.6 . . ?
O4 C8 H8A 110.3 . . ?
O4 C8 H8B 110.3 . . ?
O4 C8 C9 107.1(2) . . ?
H8A C8 H8B 108.6 . . ?
C9 C8 H8A 110.3 . . ?
C9 C8 H8B 110.3 . . ?
O5 C9 C8 106.6(2) . . ?
O5 C9 H9A 110.4 . . ?
O5 C9 H9B 110.4 . . ?
C8 C9 H9A 110.4 . . ?
C8 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
O5 C10 H10A 110.2 . . ?
O5 C10 H10B 110.2 . . ?
O5 C10 C11 107.4(2) . . ?
H10A C10 H10B 108.5 . . ?
C11 C10 H10A 110.2 . . ?
C11 C10 H10B 110.2 . . ?
O6 C11 C10 108.4(2) . . ?
O6 C11 H11A 110.0 . . ?
O6 C11 H11B 110.0 . . ?
C10 C11 H11A 110.0 . . ?
C10 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
O6 C12 H12A 109.2 . . ?
O6 C12 H12B 109.2 . . ?
O6 C12 C13 112.3(2) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
O7 C13 C12 107.7(2) . . ?
O7 C13 H13A 110.2 . . ?
O7 C13 H13B 110.2 . . ?
C12 C13 H13A 110.2 . . ?
C12 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
O7 C14 N4 120.2(2) . . ?
O7 C14 N6 113.5(2) . . ?
N4 C14 N6 126.4(2) . . ?
N4 C15 Cl2 115.19(19) . . ?
N5 C15 Cl2 115.6(2) . . ?
N5 C15 N4 129.2(2) . . ?
N5 C16 O8 111.6(2) . . ?
N6 C16 O8 120.7(2) . . ?
N6 C16 N5 127.7(2) . . ?
C18 C17 O8 123.1(2) . . ?
C18 C17 C22 122.3(2) . . ?
C22 C17 O8 114.3(2) . . ?
C17 C18 H18 120.8 . . ?
C17 C18 C19 118.3(3) . . ?
C19 C18 H18 120.8 . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.0(3) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.8 . . ?
C21 C20 C19 118.4(3) . . ?
C21 C20 H20 120.8 . . ?
C20 C21 O1 119.2(2) . . ?
C22 C21 O1 118.0(3) . . ?
C22 C21 C20 122.6(3) . . ?
C17 C22 H22 121.4 . . ?
C21 C22 C17 117.3(3) . . ?
C21 C22 H22 121.4 . . ?
O9 C23 H23A 109.5 . . ?
O9 C23 H23B 109.5 . . ?
O9 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
H10C O10 H10D 103.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H9 O10 0.854(9) 1.917(12) 2.753(3) 166(3) .
O10 H10D Br2 0.85 2.57 3.365(3) 156.6 .

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a_c
_database_code_depnum_ccdc_archive 'CCDC 1833038'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-05-17 downloaded from the CCDC.
;
_audit_creation_date             2017-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H31 Ca Cl2 N7 O10, 2(I), C2 H3 N'
_chemical_formula_sum            'C26 H34 Ca Cl2 I2 N8 O10'
_chemical_formula_weight         983.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   17.615(3)
_cell_length_b                   15.703(3)
_cell_length_c                   13.956(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3860.6(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11355
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.3
_shelx_estimated_absorpt_T_max   0.726
_shelx_estimated_absorpt_T_min   0.535
_exptl_absorpt_coefficient_mu    1.959
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       block
_exptl_crystal_F_000             1944
_exptl_crystal_size_max          0.365
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_min          0.175
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13046
_diffrn_reflns_point_group_measured_fraction_full 0.844
_diffrn_reflns_point_group_measured_fraction_max 0.822
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         1.737
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.597
_reflns_Friedel_fraction_full    0.682
_reflns_Friedel_fraction_max     0.641
_reflns_number_gt                6834
_reflns_number_total             7276
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.884
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173(2)
_refine_ls_number_reflns         7276
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0586P)²+2.6361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1148
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Rotating group:
 O9(H9A,H9B), O10(H10A,H10B)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,
 H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
 C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C9(H9)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ca1 Ca 0.28310(7) 0.21669(9) 0.72341(11) 0.0251(3) Uani 1 1 d . . . . .
Cl1 Cl 0.62909(10) -0.14110(10) 0.69521(14) 0.0362(4) Uani 1 1 d . . . . .
Cl2 Cl 0.57711(11) 0.66091(11) 0.63542(15) 0.0429(5) Uani 1 1 d . . . . .
O1 O 0.4031(3) -0.0057(3) 0.5689(4) 0.0338(11) Uani 1 1 d . . . . .
O2 O 0.6362(3) 0.1047(3) 0.4908(4) 0.0312(11) Uani 1 1 d . . . . .
O3 O 0.6112(3) 0.4039(3) 0.4542(4) 0.0300(11) Uani 1 1 d . . . . .
O4 O 0.3819(3) 0.4425(3) 0.5968(4) 0.0308(11) Uani 1 1 d . . . . .
O5 O 0.2915(2) 0.3695(3) 0.7544(3) 0.0227(9) Uani 1 1 d . . . . .
O6 O 0.2806(3) 0.2514(3) 0.8930(5) 0.0339(12) Uani 1 1 d . . . . .
O7 O 0.2763(3) 0.0930(3) 0.8244(7) 0.0479(15) Uani 1 1 d . . . . .
O8 O 0.2674(3) 0.0790(3) 0.6367(5) 0.0429(14) Uani 1 1 d . . . . .
O9 O 0.4148(3) 0.2271(3) 0.7324(5) 0.0468(15) Uani 1 1 d . . . . .
H9A H 0.448361 0.185661 0.747267 0.070 Uiso 1 1 d GR . . . .
H9B H 0.443760 0.273635 0.721592 0.070 Uiso 1 1 d GR . . . .
O10 O 0.1517(3) 0.2356(3) 0.7232(4) 0.0319(10) Uani 1 1 d . . . . .
H10A H 0.116636 0.201342 0.747654 0.048 Uiso 1 1 d GR . . . .
H10B H 0.125587 0.278690 0.698572 0.048 Uiso 1 1 d GR . . . .
N1 N 0.5080(3) -0.0700(4) 0.6234(5) 0.0297(13) Uani 1 1 d . . . . .
N2 N 0.6288(3) -0.0126(3) 0.5811(4) 0.0261(11) Uani 1 1 d . . . . .
N3 N 0.5160(3) 0.0568(4) 0.5279(4) 0.0250(12) Uani 1 1 d . . . . .
N4 N 0.5933(3) 0.5208(4) 0.5409(4) 0.0288(12) Uani 1 1 d . . . . .
N5 N 0.4715(3) 0.5480(3) 0.6103(4) 0.0277(12) Uani 1 1 d . . . . .
N6 N 0.4925(3) 0.4183(3) 0.5256(4) 0.0238(11) Uani 1 1 d . . . . .
N7 N 0.2995(3) 0.2638(4) 0.5533(5) 0.0357(14) Uani 1 1 d . . . . .
C1 C 0.4787(3) -0.0049(4) 0.5722(5) 0.0283(14) Uani 1 1 d . . . . .
C2 C 0.5831(4) -0.0661(4) 0.6252(5) 0.0300(14) Uani 1 1 d . . . . .
C3 C 0.5912(4) 0.0479(4) 0.5342(5) 0.0258(13) Uani 1 1 d . . . . .
C4 C 0.6034(4) 0.1728(4) 0.4387(5) 0.0263(13) Uani 1 1 d . . . . .
C5 C 0.5684(4) 0.1593(4) 0.3525(5) 0.0276(13) Uani 1 1 d . . . . .
H5 H 0.560048 0.103248 0.329270 0.033 Uiso 1 1 calc R . . . .
C6 C 0.5454(4) 0.2297(5) 0.2998(5) 0.0305(15) Uani 1 1 d . . . . .
H6 H 0.521267 0.221493 0.239628 0.037 Uiso 1 1 calc R . . . .
C7 C 0.5572(3) 0.3125(4) 0.3336(5) 0.0278(14) Uani 1 1 d . . . . .
H7 H 0.541963 0.360728 0.297367 0.033 Uiso 1 1 calc R . . . .
C8 C 0.5917(3) 0.3213(4) 0.4212(5) 0.0243(13) Uani 1 1 d . . . . .
C9 C 0.6148(3) 0.2531(4) 0.4763(5) 0.0260(13) Uani 1 1 d . . . . .
H9 H 0.637459 0.260998 0.537385 0.031 Uiso 1 1 calc R . . . .
C10 C 0.5619(3) 0.4475(4) 0.5086(5) 0.0221(12) Uani 1 1 d . . . . .
C11 C 0.5432(4) 0.5651(4) 0.5907(5) 0.0285(14) Uani 1 1 d . . . . .
C12 C 0.4510(4) 0.4714(4) 0.5777(5) 0.0244(13) Uani 1 1 d . . . . .
C13 C 0.3354(4) 0.4920(4) 0.6623(5) 0.0278(13) Uani 1 1 d . . . . .
H13A H 0.317371 0.544761 0.630813 0.033 Uiso 1 1 calc R . . . .
H13B H 0.364993 0.507846 0.719915 0.033 Uiso 1 1 calc R . . . .
C14 C 0.2690(4) 0.4363(4) 0.6896(5) 0.0272(13) Uani 1 1 d . . . . .
H14A H 0.229356 0.471627 0.720233 0.033 Uiso 1 1 calc R . . . .
H14B H 0.247033 0.410680 0.630983 0.033 Uiso 1 1 calc R . . . .
C15 C 0.2870(4) 0.3974(5) 0.8526(5) 0.0299(16) Uani 1 1 d . . . . .
H15A H 0.233465 0.408087 0.870327 0.036 Uiso 1 1 calc R . . . .
H15B H 0.315858 0.450975 0.860837 0.036 Uiso 1 1 calc R . . . .
C16 C 0.3195(4) 0.3297(5) 0.9149(5) 0.0325(15) Uani 1 1 d . . . . .
H16A H 0.374602 0.323478 0.902572 0.039 Uiso 1 1 calc R . . . .
H16B H 0.312311 0.344566 0.983259 0.039 Uiso 1 1 calc R . . . .
C17 C 0.3030(5) 0.1827(6) 0.9534(7) 0.047(2) Uani 1 1 d . . . . .
H17A H 0.292585 0.196599 1.021370 0.056 Uiso 1 1 calc R . . . .
H17B H 0.357923 0.171098 0.946192 0.056 Uiso 1 1 calc R . . . .
C18 C 0.2576(6) 0.1071(6) 0.9231(7) 0.052(2) Uani 1 1 d . . . . .
H18A H 0.271102 0.056672 0.962225 0.063 Uiso 1 1 calc R . . . .
H18B H 0.202654 0.118387 0.930460 0.063 Uiso 1 1 calc R . . . .
C19 C 0.2411(8) 0.0164(6) 0.7913(9) 0.077(4) Uani 1 1 d . . . . .
H19A H 0.254909 -0.032134 0.833028 0.093 Uiso 1 1 calc R . . . .
H19B H 0.185143 0.022548 0.791213 0.093 Uiso 1 1 calc R . . . .
C20 C 0.2682(9) 0.0032(6) 0.6972(10) 0.095(5) Uani 1 1 d . . . . .
H20A H 0.236921 -0.041431 0.666304 0.114 Uiso 1 1 calc R . . . .
H20B H 0.320942 -0.018477 0.700836 0.114 Uiso 1 1 calc R . . . .
C21 C 0.2842(4) 0.0603(5) 0.5376(7) 0.0395(19) Uani 1 1 d . . . . .
H21A H 0.257551 0.101721 0.495971 0.047 Uiso 1 1 calc R . . . .
H21B H 0.265190 0.002704 0.521708 0.047 Uiso 1 1 calc R . . . .
C22 C 0.3683(4) 0.0645(5) 0.5180(6) 0.0317(14) Uani 1 1 d . . . . .
H22A H 0.378119 0.059409 0.448344 0.038 Uiso 1 1 calc R . . . .
H22B H 0.389312 0.119334 0.540645 0.038 Uiso 1 1 calc R . . . .
C23 C 0.3534(5) 0.3147(6) 0.3906(6) 0.051(2) Uani 1 1 d . . . . .
H23A H 0.312741 0.314397 0.342684 0.076 Uiso 1 1 calc GR . . . .
H23B H 0.393768 0.275586 0.370663 0.076 Uiso 1 1 calc GR . . . .
H23C H 0.374079 0.372384 0.396516 0.076 Uiso 1 1 calc GR . . . .
C24 C 0.3232(4) 0.2876(5) 0.4824(5) 0.0333(15) Uani 1 1 d . . . . .
I1 I 0.55074(2) 0.08888(2) 0.81717(4) 0.03511(13) Uani 1 1 d . . . . .
I2 I 0.02442(2) 0.08832(3) 0.81773(4) 0.03854(13) Uani 1 1 d . . . . .
N8 N 0.7220(5) 0.2137(8) 0.1756(11) 0.090(4) Uani 1 1 d . . . . .
C25 C 0.6151(6) 0.2354(6) 0.0482(10) 0.067(3) Uani 1 1 d . . . . .
H25A H 0.638367 0.237836 -0.015510 0.101 Uiso 1 1 calc GR . . . .
H25B H 0.587896 0.288638 0.060799 0.101 Uiso 1 1 calc GR . . . .
H25C H 0.579357 0.187567 0.050838 0.101 Uiso 1 1 calc GR . . . .
C26 C 0.6758(7) 0.2231(6) 0.1225(11) 0.065(3) 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
Ca1 O5 2.442(5) . ?
Ca1 O6 2.429(7) . ?
Ca1 O7 2.403(7) . ?
Ca1 O8 2.493(5) . ?
Ca1 O9 2.328(5) . ?
Ca1 O10 2.334(5) . ?
Ca1 N7 2.504(8) . ?
Cl1 C2 1.732(7) . ?
Cl2 C11 1.735(7) . ?
O1 C1 1.333(7) . ?
O1 C22 1.447(9) . ?
O2 C3 1.338(8) . ?
O2 C4 1.417(7) . ?
O3 C8 1.419(7) . ?
O3 C10 1.341(8) . ?
O4 C12 1.326(8) . ?
O4 C13 1.452(8) . ?
O5 C14 1.441(8) . ?
O5 C15 1.440(9) . ?
O6 C16 1.441(8) . ?
O6 C17 1.425(10) . ?
O7 C18 1.434(13) . ?
O7 C19 1.431(12) . ?
O8 C20 1.460(13) . ?
O8 C21 1.444(10) . ?
O9 H9A 0.9040 . ?
O9 H9B 0.9042 . ?
O10 H10A 0.8878 . ?
O10 H10B 0.8871 . ?
N1 C1 1.351(9) . ?
N1 C2 1.324(9) . ?
N2 C2 1.316(9) . ?
N2 C3 1.332(8) . ?
N3 C1 1.323(9) . ?
N3 C3 1.335(8) . ?
N4 C10 1.354(8) . ?
N4 C11 1.321(9) . ?
N5 C11 1.320(9) . ?
N5 C12 1.337(8) . ?
N6 C10 1.327(8) . ?
N6 C12 1.326(8) . ?
N7 C24 1.136(10) . ?
C4 C5 1.369(10) . ?
C4 C9 1.380(9) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(9) . ?
C6 H6 0.9500 . ?
C6 C7 1.399(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.372(9) . ?
C8 C9 1.380(9) . ?
C9 H9 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.509(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.488(10) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.492(12) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.413(16) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.508(9) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 C24 1.451(11) . ?
N8 C26 1.109(17) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C25 C26 1.503(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Ca1 O8 160.8(2) . . ?
O5 Ca1 N7 82.57(19) . . ?
O6 Ca1 O5 66.94(16) . . ?
O6 Ca1 O8 131.7(2) . . ?
O6 Ca1 N7 149.30(18) . . ?
O7 Ca1 O5 133.9(2) . . ?
O7 Ca1 O6 67.0(2) . . ?
O7 Ca1 O8 65.1(3) . . ?
O7 Ca1 N7 143.2(3) . . ?
O8 Ca1 N7 79.0(2) . . ?
O9 Ca1 O5 82.02(17) . . ?
O9 Ca1 O6 87.1(2) . . ?
O9 Ca1 O7 94.3(2) . . ?
O9 Ca1 O8 101.4(2) . . ?
O9 Ca1 O10 168.3(2) . . ?
O9 Ca1 N7 85.2(2) . . ?
O10 Ca1 O5 86.28(16) . . ?
O10 Ca1 O6 87.41(17) . . ?
O10 Ca1 O7 93.13(19) . . ?
O10 Ca1 O8 89.97(19) . . ?
O10 Ca1 N7 94.3(2) . . ?
C1 O1 C22 115.6(5) . . ?
C3 O2 C4 119.5(5) . . ?
C10 O3 C8 119.6(5) . . ?
C12 O4 C13 117.5(5) . . ?
C14 O5 Ca1 126.0(4) . . ?
C15 O5 Ca1 117.6(4) . . ?
C15 O5 C14 111.2(5) . . ?
C16 O6 Ca1 113.0(4) . . ?
C17 O6 Ca1 113.7(5) . . ?
C17 O6 C16 112.8(6) . . ?
C18 O7 Ca1 116.8(5) . . ?
C19 O7 Ca1 120.8(7) . . ?
C19 O7 C18 109.9(8) . . ?
C20 O8 Ca1 115.2(6) . . ?
C21 O8 Ca1 128.2(5) . . ?
C21 O8 C20 112.7(7) . . ?
Ca1 O9 H9A 127.9 . . ?
Ca1 O9 H9B 127.6 . . ?
H9A O9 H9B 104.5 . . ?
Ca1 O10 H10A 127.8 . . ?
Ca1 O10 H10B 127.7 . . ?
H10A O10 H10B 104.5 . . ?
C2 N1 C1 110.9(6) . . ?
C2 N2 C3 112.4(6) . . ?
C1 N3 C3 112.7(6) . . ?
C11 N4 C10 110.5(6) . . ?
C11 N5 C12 111.8(6) . . ?
C12 N6 C10 112.9(5) . . ?
C24 N7 Ca1 164.7(6) . . ?
O1 C1 N1 113.1(6) . . ?
N3 C1 O1 119.2(6) . . ?
N3 C1 N1 127.7(6) . . ?
N1 C2 Cl1 116.5(5) . . ?
N2 C2 Cl1 114.3(5) . . ?
N2 C2 N1 129.2(7) . . ?
N2 C3 O2 113.7(6) . . ?
N2 C3 N3 126.9(6) . . ?
N3 C3 O2 119.3(6) . . ?
C5 C4 O2 121.2(6) . . ?
C5 C4 C9 122.7(6) . . ?
C9 C4 O2 115.8(6) . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.3(6) . . ?
C6 C5 H5 120.8 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.2(6) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 121.3 . . ?
C8 C7 C6 117.4(6) . . ?
C8 C7 H7 121.3 . . ?
C7 C8 O3 119.3(6) . . ?
C7 C8 C9 123.3(6) . . ?
C9 C8 O3 117.2(6) . . ?
C4 C9 C8 117.0(6) . . ?
C4 C9 H9 121.5 . . ?
C8 C9 H9 121.5 . . ?
O3 C10 N4 111.0(5) . . ?
N6 C10 O3 121.4(5) . . ?
N6 C10 N4 127.6(6) . . ?
N4 C11 Cl2 114.6(5) . . ?
N5 C11 Cl2 115.5(5) . . ?
N5 C11 N4 129.9(7) . . ?
O4 C12 N5 119.2(6) . . ?
O4 C12 N6 113.7(5) . . ?
N6 C12 N5 127.1(6) . . ?
O4 C13 H13A 110.4 . . ?
O4 C13 H13B 110.4 . . ?
O4 C13 C14 106.5(5) . . ?
H13A C13 H13B 108.6 . . ?
C14 C13 H13A 110.4 . . ?
C14 C13 H13B 110.4 . . ?
O5 C14 C13 111.6(5) . . ?
O5 C14 H14A 109.3 . . ?
O5 C14 H14B 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
O5 C15 H15A 110.0 . . ?
O5 C15 H15B 110.0 . . ?
O5 C15 C16 108.5(6) . . ?
H15A C15 H15B 108.4 . . ?
C16 C15 H15A 110.0 . . ?
C16 C15 H15B 110.0 . . ?
O6 C16 C15 107.6(5) . . ?
O6 C16 H16A 110.2 . . ?
O6 C16 H16B 110.2 . . ?
C15 C16 H16A 110.2 . . ?
C15 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
O6 C17 H17A 110.4 . . ?
O6 C17 H17B 110.4 . . ?
O6 C17 C18 106.6(7) . . ?
H17A C17 H17B 108.6 . . ?
C18 C17 H17A 110.4 . . ?
C18 C17 H17B 110.4 . . ?
O7 C18 C17 105.8(8) . . ?
O7 C18 H18A 110.6 . . ?
O7 C18 H18B 110.6 . . ?
C17 C18 H18A 110.6 . . ?
C17 C18 H18B 110.6 . . ?
H18A C18 H18B 108.7 . . ?
O7 C19 H19A 110.5 . . ?
O7 C19 H19B 110.5 . . ?
H19A C19 H19B 108.7 . . ?
C20 C19 O7 106.1(9) . . ?
C20 C19 H19A 110.5 . . ?
C20 C19 H19B 110.5 . . ?
O8 C20 H20A 108.7 . . ?
O8 C20 H20B 108.7 . . ?
C19 C20 O8 114.4(9) . . ?
C19 C20 H20A 108.7 . . ?
C19 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
O8 C21 H21A 109.3 . . ?
O8 C21 H21B 109.3 . . ?
O8 C21 C22 111.5(6) . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
O1 C22 C21 107.1(6) . . ?
O1 C22 H22A 110.3 . . ?
O1 C22 H22B 110.3 . . ?
C21 C22 H22A 110.3 . . ?
C21 C22 H22B 110.3 . . ?
H22A C22 H22B 108.6 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
N7 C24 C23 177.9(8) . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
N8 C26 C25 178.2(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H9A I1 0.90 2.55 3.442(5) 168.3 .
O9 H9B I2 0.90 2.92 3.681(5) 143.0 3
O10 H10A I2 0.89 2.60 3.481(5) 174.0 .
O10 H10B I1 0.89 2.97 3.533(5) 123.3 3_455

_olex2_submission_special_instructions 'No special instructions were received'
