# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ap1242
_database_code_depnum_ccdc_archive 'CCDC 1478545'
_audit_update_record             
;
2016-05-06 deposited with the CCDC.
2016-07-07 downloaded from the CCDC.
;
_audit_creation_date             2014-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.5(C24 H44 Ca2 Cl4 N4 O8)'
_chemical_formula_sum            'C12 H22 Ca Cl2 N2 O4'
_chemical_formula_weight         369.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         CaCl2C7H11NO2
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.9663(3)
_cell_length_b                   11.8541(3)
_cell_length_c                   11.4866(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.407(3)
_cell_angle_gamma                90.00
_cell_volume                     1702.08(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.3144
_cell_measurement_theta_min      3.2472
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94741
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.4869
_exptl_crystal_size_mid          0.3517
_exptl_crystal_size_min          0.3486
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15388
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.25
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 16.1511
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0326836000
_diffrn_orient_matrix_UB_12      0.0116412000
_diffrn_orient_matrix_UB_13      0.0392423000
_diffrn_orient_matrix_UB_21      0.0112816000
_diffrn_orient_matrix_UB_22      -0.0543392000
_diffrn_orient_matrix_UB_23      0.0260522000
_diffrn_orient_matrix_UB_31      0.0449951000
_diffrn_orient_matrix_UB_32      0.0221264000
_diffrn_orient_matrix_UB_33      0.0434298000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1603
_reflns_number_total             1675
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     99
_refine_ls_number_reflns         1675
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0218
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0321P)²+1.0715P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0582
_refine_ls_wR_factor_ref         0.0591
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O1-H1
 0.85 with sigma of 0.01
 C6-H1
 1.887149 with sigma of 0.02
 Ca1-H1
 2.982527 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C6(H6A,H6B), C4(H4A,H4B), C5(H5A,H5B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Ca1 Ca 0.0000 0.56265(3) 0.7500 0.01364(10) Uani 1 2 d . . DS T
Cl1 Cl 0.07573(3) 0.70576(3) 0.61025(3) 0.02530(11) Uani 1 1 d . . . .
O2 O 0.16062(7) 0.54994(7) 0.89190(8) 0.0205(2) Uani 1 1 d . . . .
O1 O 0.04062(7) 0.40958(7) 0.63337(8) 0.0205(2) Uani 1 1 d . . D .
H1 H 0.0018(10) 0.3866(12) 0.5672(10) 0.031 Uiso 1 1 d . . DR .
C1 C 0.38908(11) 0.54298(13) 0.61945(12) 0.0293(3) Uani 1 1 d . . . .
H1A H 0.4159 0.6098 0.6701 0.035 Uiso 1 1 calc . . R .
H1B H 0.4494 0.5070 0.5959 0.035 Uiso 1 1 calc . . R .
N1 N 0.25228(8) 0.40904(9) 0.58639(9) 0.0171(2) Uani 1 1 d . . . .
C2 C 0.29990(11) 0.57523(11) 0.50881(11) 0.0227(3) Uani 1 1 d . . . .
H2A H 0.2605 0.6424 0.5251 0.027 Uiso 1 1 calc . . R .
H2B H 0.3286 0.5909 0.4387 0.027 Uiso 1 1 calc . . R .
C6 C 0.11883(10) 0.32514(10) 0.68043(11) 0.0207(3) Uani 1 1 d . . D .
H6A H 0.0822 0.2531 0.6872 0.025 Uiso 1 1 calc . . R .
H6B H 0.1605 0.3474 0.7625 0.025 Uiso 1 1 calc . . R .
C4 C 0.33475(11) 0.45964(12) 0.68580(11) 0.0256(3) Uani 1 1 d . . . .
H4A H 0.3858 0.4021 0.7295 0.031 Uiso 1 1 calc . . R .
H4B H 0.3025 0.4989 0.7436 0.031 Uiso 1 1 calc . . R .
C3 C 0.22928(9) 0.47267(10) 0.48700(10) 0.0166(2) Uani 1 1 d . . . .
C5 C 0.19491(10) 0.30730(10) 0.60168(11) 0.0187(3) Uani 1 1 d . . . .
H5A H 0.2473 0.2481 0.6384 0.022 Uiso 1 1 calc . . R .
H5B H 0.1537 0.2801 0.5213 0.022 Uiso 1 1 calc . . R .


_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 Cl1 2.6938(4) . ?
Ca1 Cl1 2.6938(3) 2_556 ?
Ca1 O2 2.2832(9) . ?
Ca1 O2 2.2832(9) 2_556 ?
Ca1 O1 2.3957(9) 2_556 ?
Ca1 O1 2.3957(9) . ?
O2 C3 1.2414(15) 6_566 ?
O1 C6 1.4253(15) . ?
C1 C2 1.5224(18) . ?
C1 C4 1.5292(19) . ?
N1 C4 1.4691(16) . ?
N1 C3 1.3343(16) . ?
N1 C5 1.4519(16) . ?
C2 C3 1.5025(17) . ?
C6 C5 1.5200(17) . ?
C3 O2 1.2414(15) 6_565 ?

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
Cl1 Ca1 Cl1 101.937(17) 2_556 . ?
O2 Ca1 Cl1 91.37(2) 2_556 . ?
O2 Ca1 Cl1 93.39(2) . . ?
O2 Ca1 Cl1 91.37(2) . 2_556 ?
O2 Ca1 Cl1 93.39(2) 2_556 2_556 ?
O2 Ca1 O2 172.43(5) . 2_556 ?
O2 Ca1 O1 81.09(3) . 2_556 ?
O2 Ca1 O1 93.14(3) 2_556 2_556 ?
O2 Ca1 O1 81.09(3) 2_556 . ?
O2 Ca1 O1 93.15(3) . . ?
O1 Ca1 Cl1 168.32(2) . 2_556 ?
O1 Ca1 Cl1 88.55(2) 2_556 2_556 ?
O1 Ca1 Cl1 88.55(2) . . ?
O1 Ca1 Cl1 168.32(2) 2_556 . ?
O1 Ca1 O1 81.53(4) . 2_556 ?
C3 O2 Ca1 161.32(8) 6_566 . ?
C6 O1 Ca1 124.05(7) . . ?
C2 C1 C4 103.30(10) . . ?
C3 N1 C4 112.66(10) . . ?
C3 N1 C5 124.59(10) . . ?
C5 N1 C4 122.39(10) . . ?
C3 C2 C1 103.30(10) . . ?
O1 C6 C5 112.39(10) . . ?
N1 C4 C1 102.30(10) . . ?
O2 C3 N1 125.16(11) 6_565 . ?
O2 C3 C2 125.75(11) 6_565 . ?
N1 C3 C2 109.09(10) . . ?
N1 C5 C6 113.00(10) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-13 6 12 0.1723 -13.0001 6.0000 12.0000 0.9656 -0.1601 0.0690
15 -4 -11 0.1539 15.0001 -4.0000 -11.0000 -0.9685 0.1000 0.1087
11 6 8 0.1820 11.0000 6.0000 8.0000 0.0243 0.0065 0.9751
-2 -8 -13 0.2001 -1.9999 -8.0000 -13.0000 -0.5379 0.0735 -0.8316
-16 -4 -2 0.2025 -16.0000 -4.0000 -2.0000 0.3979 -0.0153 -0.8953
13 -9 3 0.1541 12.9999 -9.0000 3.0000 -0.4119 0.7139 0.5161
0 -16 -5 0.1715 -0.0000 -16.0000 -5.0000 -0.3825 0.7392 -0.5712
-7 15 2 0.1548 -7.0000 15.0000 2.0000 0.4819 -0.8420 0.1038
-6 -11 12 0.1950 -6.0001 -11.0000 12.0000 0.5390 0.8427 0.0078
3 16 -5 0.1268 3.0001 16.0000 -5.0000 -0.1080 -0.9658 0.2719

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method Ethanol
_chemical_properties_physical    Hygroscopic
####################################################################### 
# 
# 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_AP74
_database_code_depnum_ccdc_archive 'CCDC 1478546'
_audit_update_record             
;
2016-05-06 deposited with the CCDC.
2016-07-07 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            'C24 H58 Ca2 Cl4 N4 O15'
_chemical_formula_weight         864.70

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'
O O 0.0106 0.0060 '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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.9178(3)
_cell_length_b                   16.3074(7)
_cell_length_c                   16.3501(6)
_cell_angle_alpha                116.158(4)
_cell_angle_beta                 97.927(3)
_cell_angle_gamma                99.693(4)
_cell_volume                     2042.37(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7260
_cell_measurement_theta_max      32.5373
_cell_measurement_theta_min      2.5117

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             916
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5267
_exptl_crystal_size_mid          0.2548
_exptl_crystal_size_min          0.1614
_exptl_absorpt_coefficient_mu    0.604
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_T_max  0.838
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24682
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.517
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7994
_reflns_number_gt                6303
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+0.0794P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7994
_refine_ls_number_parameters     514
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0898
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.002
_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
Ca1 Ca 0.42266(5) 0.52691(3) 0.26738(3) 0.01247(10) Uani 1 1 d . . . . .
Ca2 Ca -0.58037(5) 0.01444(3) -0.23593(3) 0.01402(10) Uani 1 1 d . . . . .
Cl3 Cl 0.32400(6) 0.34944(3) -0.10260(3) 0.01634(12) Uani 1 1 d . . . . .
Cl4 Cl -0.64139(6) -0.15905(3) -0.60450(3) 0.01870(12) Uani 1 1 d . . . . .
O2 O -0.21834(15) 0.30240(9) -0.07224(9) 0.0158(3) Uani 1 1 d . . . . .
O3S O 0.4803(2) 0.47437(12) 0.11509(11) 0.0206(4) Uani 1 1 d . . . . .
O5 O -1.09759(16) -0.13661(9) -0.53767(9) 0.0177(3) Uani 1 1 d . . . . .
O4 O -0.84304(16) 0.00111(10) -0.27917(10) 0.0230(3) Uani 1 1 d . . . . .
N3 N -1.10478(19) -0.06356(11) -0.34570(11) 0.0163(4) Uani 1 1 d . . . . .
O7S O -0.54554(19) -0.01438(13) -0.38480(11) 0.0232(4) Uani 1 1 d . . . . .
O9S O -0.62183(19) -0.00005(13) -0.10289(11) 0.0232(4) Uani 1 1 d . . . . .
O2S O 0.43164(19) 0.65792(11) 0.23237(12) 0.0205(3) Uani 1 1 d . . . . .
N1 N -0.10233(19) 0.40978(11) 0.13319(11) 0.0159(4) Uani 1 1 d . . . . .
O3 O -0.31298(16) 0.05685(10) -0.18149(10) 0.0222(3) Uani 1 1 d . . . . .
O1 O 0.15825(17) 0.47818(11) 0.19551(10) 0.0263(4) Uani 1 1 d . . . . .
O6S O -0.5258(2) 0.17881(11) -0.16068(12) 0.0282(4) Uani 1 1 d . . . . .
O5S O 0.36881(19) 0.48689(12) 0.39019(11) 0.0218(4) Uani 1 1 d . . . . .
O6 O -1.30760(16) -0.43406(10) -0.68209(10) 0.0223(3) Uani 1 1 d . . . . .
O8S O -0.6004(2) -0.14650(11) -0.28054(13) 0.0237(4) Uani 1 1 d . . . . .
O4S O 0.4135(2) 0.36120(11) 0.21895(13) 0.0243(4) Uani 1 1 d . . . . .
C5 C -0.1200(2) 0.45468(14) 0.07419(14) 0.0182(5) Uani 1 1 d . . . . .
H5A H -0.0178 0.4709 0.0604 0.022 Uiso 1 1 calc R U . . .
H5B H -0.1492 0.5144 0.1094 0.022 Uiso 1 1 calc R U . . .
N2 N -0.06852(19) 0.15756(11) -0.11371(11) 0.0153(4) Uani 1 1 d . . . . .
C17 C -1.1218(2) -0.01071(14) -0.39680(14) 0.0198(5) Uani 1 1 d . . . . .
H17A H -1.0176 0.0288 -0.3881 0.024 Uiso 1 1 calc R U . . .
H17B H -1.1890 0.0321 -0.3703 0.024 Uiso 1 1 calc R U . . .
N4 N -1.07082(19) -0.32705(11) -0.60275(11) 0.0165(4) Uani 1 1 d . . . . .
C20 C -1.0736(2) -0.27953(14) -0.66035(14) 0.0194(5) Uani 1 1 d . . . . .
H20A H -1.1178 -0.3272 -0.7271 0.023 Uiso 1 1 calc R U . . .
H20B H -0.9651 -0.2471 -0.6541 0.023 Uiso 1 1 calc R U . . .
C7 C -0.0894(2) 0.30483(14) -0.11564(15) 0.0188(5) Uani 1 1 d . . . . .
H7A H 0.0090 0.3439 -0.0671 0.023 Uiso 1 1 calc R U . . .
H7B H -0.1070 0.3329 -0.1578 0.023 Uiso 1 1 calc R U . . .
C6 C -0.2421(2) 0.39374(14) -0.01779(14) 0.0180(4) Uani 1 1 d . . . . .
H6A H -0.3468 0.3856 -0.0042 0.022 Uiso 1 1 calc R U . . .
H6B H -0.2417 0.4273 -0.0556 0.022 Uiso 1 1 calc R U . . .
C18 C -1.1927(2) -0.07382(15) -0.50041(14) 0.0207(5) Uani 1 1 d . . . . .
H18A H -1.3003 -0.1103 -0.5104 0.025 Uiso 1 1 calc R U . . .
H18B H -1.1985 -0.0350 -0.5327 0.025 Uiso 1 1 calc R U . . .
O1S O 0.4408(3) 0.67006(12) 0.40956(13) 0.0431(5) Uani 1 1 d . . . . .
C8 C -0.0773(2) 0.20462(14) -0.17113(14) 0.0192(5) Uani 1 1 d . . . . .
H8A H -0.1699 0.1686 -0.2249 0.023 Uiso 1 1 calc R U . . .
H8B H 0.0172 0.2055 -0.1965 0.023 Uiso 1 1 calc R U . . .
C19 C -1.1699(2) -0.20830(14) -0.63195(14) 0.0203(5) Uani 1 1 d . . . . .
H19A H -1.1750 -0.1799 -0.6744 0.024 Uiso 1 1 calc R U . . .
H19B H -1.2780 -0.2396 -0.6361 0.024 Uiso 1 1 calc R U . . .
C1 C 0.0334(2) 0.42713(15) 0.19043(14) 0.0196(5) Uani 1 1 d . . . . .
C13 C -0.9692(2) -0.05537(14) -0.29354(14) 0.0170(4) Uani 1 1 d . . . . .
C12 C 0.0593(3) 0.19276(16) -0.03010(15) 0.0242(5) Uani 1 1 d . . . . .
H12A H 0.0559 0.2549 0.0196 0.029 Uiso 1 1 calc R U . . .
H12B H 0.1628 0.1983 -0.0455 0.029 Uiso 1 1 calc R U . . .
C9 C -0.1901(2) 0.09295(14) -0.11944(14) 0.0172(4) Uani 1 1 d . . . . .
C21 C -1.1901(2) -0.39640(14) -0.61538(14) 0.0172(4) Uani 1 1 d . . . . .
C24 C -0.9504(3) -0.29211(16) -0.51605(15) 0.0239(5) Uani 1 1 d . . . . .
H24A H -0.9606 -0.2320 -0.4662 0.029 Uiso 1 1 calc R U . . .
H24B H -0.8438 -0.2827 -0.5269 0.029 Uiso 1 1 calc R U . . .
C16 C -1.2337(2) -0.13895(15) -0.35536(15) 0.0226(5) Uani 1 1 d . . . . .
H16A H -1.2578 -0.1950 -0.4181 0.027 Uiso 1 1 calc R U . . .
H16B H -1.3296 -0.1166 -0.3455 0.027 Uiso 1 1 calc R U . . .
C10 C -0.1538(3) 0.07471(16) -0.03769(16) 0.0267(5) Uani 1 1 d . . . . .
H10A H -0.1831 0.0061 -0.0579 0.032 Uiso 1 1 calc R U . . .
H10B H -0.2095 0.1071 0.0107 0.032 Uiso 1 1 calc R U . . .
C14 C -0.9933(3) -0.12439(16) -0.25556(15) 0.0246(5) Uani 1 1 d . . . . .
H14A H -0.9485 -0.0924 -0.1870 0.029 Uiso 1 1 calc R U . . .
H14B H -0.9436 -0.1764 -0.2863 0.029 Uiso 1 1 calc R U . . .
C4 C -0.2349(2) 0.35384(16) 0.14588(15) 0.0229(5) Uani 1 1 d . . . . .
H4A H -0.2931 0.2981 0.0855 0.028 Uiso 1 1 calc R U . . .
H4B H -0.3077 0.3924 0.1725 0.028 Uiso 1 1 calc R U . . .
C23 C -0.9860(3) -0.37210(17) -0.49070(17) 0.0306(6) Uani 1 1 d . . . . .
H23A H -0.9226 -0.4177 -0.5165 0.037 Uiso 1 1 calc R U . . .
H23B H -0.9643 -0.3468 -0.4218 0.037 Uiso 1 1 calc R U . . .
C22 C -1.1608(3) -0.41888(16) -0.53596(15) 0.0261(5) Uani 1 1 d . . . . .
H22A H -1.1842 -0.4880 -0.5593 0.031 Uiso 1 1 calc R U . . .
H22B H -1.2250 -0.3919 -0.4909 0.031 Uiso 1 1 calc R U . . .
C11 C 0.0247(3) 0.11602(17) -0.00057(17) 0.0317(6) Uani 1 1 d . . . . .
H11A H 0.0554 0.1434 0.0685 0.038 Uiso 1 1 calc R U . . .
H11B H 0.0809 0.0670 -0.0292 0.038 Uiso 1 1 calc R U . . .
C15 C -1.1704(3) -0.16177(17) -0.27848(16) 0.0294(6) Uani 1 1 d . . . . .
H15A H -1.2116 -0.1301 -0.2225 0.035 Uiso 1 1 calc R U . . .
H15B H -1.1999 -0.2308 -0.3010 0.035 Uiso 1 1 calc R U . . .
C3 C -0.1603(3) 0.32395(19) 0.21349(17) 0.0370(7) Uani 1 1 d . . . . .
H3A H -0.2114 0.3393 0.2666 0.044 Uiso 1 1 calc R U . . .
H3B H -0.1703 0.2550 0.1813 0.044 Uiso 1 1 calc R U . . .
C2 C 0.0095(3) 0.37779(19) 0.24812(17) 0.0351(6) Uani 1 1 d . . . . .
H2A H 0.0334 0.4242 0.3156 0.042 Uiso 1 1 calc R U . . .
H2B H 0.0780 0.3341 0.2392 0.042 Uiso 1 1 calc R U . . .
Cl2 Cl 0.46029(7) 0.15801(3) 0.09979(3) 0.02351(13) Uani 1 1 d . . . . .
Cl1 Cl 0.55219(7) 0.34321(3) 0.40492(3) 0.02259(13) Uani 1 1 d . . . . .
H2SA H 0.419(3) 0.707(2) 0.268(2) 0.054(10) Uiso 1 1 d . . . . .
H3SA H 0.530(3) 0.5175(18) 0.1142(17) 0.033(8) Uiso 1 1 d . . . . .
H5SB H 0.409(3) 0.446(2) 0.398(2) 0.056(10) Uiso 1 1 d . . . . .
H4SA H 0.452(3) 0.353(2) 0.258(2) 0.052(11) Uiso 1 1 d . . . . .
H8SA H -0.561(3) -0.150(2) -0.239(2) 0.053(11) Uiso 1 1 d . . . . .
H3SB H 0.430(3) 0.4357(18) 0.0622(19) 0.037(8) Uiso 1 1 d . . . . .
H9SB H -0.581(3) -0.0429(19) -0.0964(18) 0.043(8) Uiso 1 1 d . . . . .
H8SB H -0.598(3) -0.198(2) -0.3285(19) 0.044(8) Uiso 1 1 d . . . . .
H7SB H -0.578(3) -0.0524(18) -0.4356(18) 0.035(8) Uiso 1 1 d . . . . .
H7SA H -0.498(3) 0.036(2) -0.3854(18) 0.044(8) Uiso 1 1 d . . . . .
H4SB H 0.426(3) 0.3175(19) 0.1749(19) 0.041(9) Uiso 1 1 d . . . . .
H5SA H 0.384(3) 0.526(2) 0.443(2) 0.044(9) Uiso 1 1 d . . . . .
H1SA H 0.409(4) 0.721(2) 0.409(2) 0.069(10) Uiso 1 1 d . . . . .
H2SB H 0.485(3) 0.6614(19) 0.1966(19) 0.046(9) Uiso 1 1 d . . . . .
H9SA H -0.602(3) 0.041(2) -0.051(2) 0.051(10) Uiso 1 1 d . . . . .
H6SA H -0.428(5) 0.209(3) -0.149(3) 0.111(15) Uiso 1 1 d . . . . .
H1SB H 0.443(4) 0.673(2) 0.460(2) 0.068(11) Uiso 1 1 d . . . . .
H6SB H -0.589(5) 0.222(3) -0.132(3) 0.106(14) Uiso 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 O6 2.3122(14) 1_766 ?
Ca1 O1 2.3138(14) . ?
Ca1 O3S 2.4121(15) . ?
Ca1 O1S 2.4217(18) . ?
Ca1 O2S 2.4355(16) . ?
Ca1 O4S 2.4408(17) . ?
Ca1 O5S 2.4503(16) . ?
Ca2 O4 2.2957(15) . ?
Ca2 O3 2.2964(14) . ?
Ca2 O6S 2.3288(16) . ?
Ca2 O7S 2.3433(16) . ?
Ca2 O8S 2.3601(16) . ?
Ca2 O9S 2.3601(16) . ?
O2 C6 1.430(2) . ?
O2 C7 1.436(2) . ?
O5 C18 1.423(3) . ?
O5 C19 1.429(2) . ?
O4 C13 1.248(2) . ?
N3 C13 1.329(3) . ?
N3 C17 1.452(3) . ?
N3 C16 1.470(2) . ?
N1 C1 1.326(3) . ?
N1 C5 1.453(2) . ?
N1 C4 1.464(2) . ?
O3 C9 1.235(2) . ?
O1 C1 1.242(2) . ?
O6 C21 1.242(2) . ?
O6 Ca1 2.3122(14) 1_344 ?
C5 C6 1.517(3) . ?
N2 C9 1.340(2) . ?
N2 C8 1.453(2) . ?
N2 C12 1.468(2) . ?
C17 C18 1.509(3) . ?
N4 C21 1.335(2) . ?
N4 C20 1.460(2) . ?
N4 C24 1.466(2) . ?
C20 C19 1.508(3) . ?
C7 C8 1.511(3) . ?
C1 C2 1.500(3) . ?
C13 C14 1.507(3) . ?
C12 C11 1.529(3) . ?
C9 C10 1.498(3) . ?
C21 C22 1.499(3) . ?
C24 C23 1.532(3) . ?
C16 C15 1.525(3) . ?
C10 C11 1.539(3) . ?
C14 C15 1.522(3) . ?
C4 C3 1.511(3) . ?
C23 C22 1.531(3) . ?
C3 C2 1.504(3) . ?

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
O6 Ca1 O1 171.87(6) 1_766 . ?
O6 Ca1 O3S 82.75(6) 1_766 . ?
O1 Ca1 O3S 89.17(6) . . ?
O6 Ca1 O1S 84.47(7) 1_766 . ?
O1 Ca1 O1S 102.51(7) . . ?
O3S Ca1 O1S 141.21(6) . . ?
O6 Ca1 O2S 92.35(5) 1_766 . ?
O1 Ca1 O2S 86.15(5) . . ?
O3S Ca1 O2S 73.59(6) . . ?
O1S Ca1 O2S 70.53(6) . . ?
O6 Ca1 O4S 89.88(6) 1_766 . ?
O1 Ca1 O4S 87.58(6) . . ?
O3S Ca1 O4S 77.94(6) . . ?
O1S Ca1 O4S 138.52(7) . . ?
O2S Ca1 O4S 150.91(6) . . ?
O6 Ca1 O5S 95.40(5) 1_766 . ?
O1 Ca1 O5S 90.92(5) . . ?
O3S Ca1 O5S 147.15(6) . . ?
O1S Ca1 O5S 70.46(6) . . ?
O2S Ca1 O5S 139.19(6) . . ?
O4S Ca1 O5S 69.24(6) . . ?
O4 Ca2 O3 169.55(5) . . ?
O4 Ca2 O6S 91.29(6) . . ?
O3 Ca2 O6S 78.28(6) . . ?
O4 Ca2 O7S 92.28(6) . . ?
O3 Ca2 O7S 89.03(6) . . ?
O6S Ca2 O7S 100.16(6) . . ?
O4 Ca2 O8S 97.19(6) . . ?
O3 Ca2 O8S 93.19(6) . . ?
O6S Ca2 O8S 167.16(6) . . ?
O7S Ca2 O8S 89.17(6) . . ?
O4 Ca2 O9S 89.22(6) . . ?
O3 Ca2 O9S 92.24(6) . . ?
O6S Ca2 O9S 94.97(6) . . ?
O7S Ca2 O9S 164.75(6) . . ?
O8S Ca2 O9S 75.59(6) . . ?
C6 O2 C7 113.39(14) . . ?
C18 O5 C19 111.98(15) . . ?
C13 O4 Ca2 137.22(14) . . ?
C13 N3 C17 123.71(17) . . ?
C13 N3 C16 113.51(17) . . ?
C17 N3 C16 122.47(16) . . ?
C1 N1 C5 122.25(16) . . ?
C1 N1 C4 113.80(17) . . ?
C5 N1 C4 123.30(16) . . ?
C9 O3 Ca2 154.04(14) . . ?
C1 O1 Ca1 141.17(14) . . ?
C21 O6 Ca1 148.20(14) . 1_344 ?
N1 C5 C6 113.75(16) . . ?
C9 N2 C8 122.80(16) . . ?
C9 N2 C12 113.49(16) . . ?
C8 N2 C12 122.13(16) . . ?
N3 C17 C18 112.72(17) . . ?
C21 N4 C20 122.93(16) . . ?
C21 N4 C24 113.35(17) . . ?
C20 N4 C24 122.86(16) . . ?
N4 C20 C19 111.72(17) . . ?
O2 C7 C8 108.18(15) . . ?
O2 C6 C5 114.01(17) . . ?
O5 C18 C17 108.78(16) . . ?
N2 C8 C7 111.69(16) . . ?
O5 C19 C20 108.27(16) . . ?
O1 C1 N1 124.26(19) . . ?
O1 C1 C2 126.48(19) . . ?
N1 C1 C2 109.25(18) . . ?
O4 C13 N3 124.48(19) . . ?
O4 C13 C14 126.21(19) . . ?
N3 C13 C14 109.30(17) . . ?
N2 C12 C11 102.19(16) . . ?
O3 C9 N2 124.62(19) . . ?
O3 C9 C10 126.38(19) . . ?
N2 C9 C10 108.98(17) . . ?
O6 C21 N4 124.35(19) . . ?
O6 C21 C22 126.23(18) . . ?
N4 C21 C22 109.40(17) . . ?
N4 C24 C23 102.38(16) . . ?
N3 C16 C15 103.46(16) . . ?
C9 C10 C11 103.34(17) . . ?
C13 C14 C15 104.55(18) . . ?
N1 C4 C3 104.21(17) . . ?
C22 C23 C24 104.08(18) . . ?
C21 C22 C23 103.31(17) . . ?
C12 C11 C10 103.77(18) . . ?
C14 C15 C16 104.92(17) . . ?
C2 C3 C4 106.41(18) . . ?
C1 C2 C3 105.50(18) . . ?

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
O2S H2SA Cl4 0.80(3) 2.47(3) 3.2498(18) 167(3) 1_666
O3S H3SA Cl3 0.78(3) 2.43(3) 3.2048(17) 176(2) 2_665
O5S H5SB Cl1 0.85(3) 2.30(3) 3.1467(19) 169(3) .
O4S H4SA Cl1 0.76(3) 2.52(3) 3.2760(19) 170(3) .
O3S H3SB Cl3 0.82(3) 2.37(3) 3.1691(17) 165(2) .
O8S H8SB Cl1 0.86(3) 2.28(3) 3.0927(17) 156(2) 2
O7S H7SB Cl4 0.76(3) 2.44(3) 3.1941(18) 169(3) .
O7S H7SA Cl4 0.87(3) 2.26(3) 3.1204(17) 174(3) 2_454
O4S H4SB Cl2 0.80(3) 2.43(3) 3.1538(18) 151(2) .
O5S H5SA Cl1 0.79(3) 2.36(3) 3.1470(17) 173(3) 2_666
O1S H1SA Cl4 0.93(3) 2.17(3) 3.092(2) 172(3) 1_666
O2S H2SB Cl3 0.82(3) 2.43(3) 3.2255(18) 166(3) 2_665
O9S H9SA Cl2 0.79(3) 2.26(3) 3.0538(17) 178(3) 1_455
O6S H6SA O2 0.88(4) 2.03(4) 2.854(2) 157(4) .
O1S H1SB Cl1 0.80(3) 2.34(3) 3.1275(19) 171(3) 2_666
O6S H6SB Cl3 0.97(4) 2.22(4) 3.1169(18) 153(3) 1_455

_refine_diff_density_max         0.691
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.059

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
9 8 -18 0.1025 9.0000 8.0000 -18.0000 0.9077 -0.4167 0.1320
-9 -12 7 0.0824 -9.0000 -12.0000 7.0000 -0.7448 0.3652 0.5126
-3 1 20 0.1437 -3.0000 1.0000 20.0000 -0.5100 0.2502 -0.8095
-8 18 -12 0.1067 -8.0000 18.0000 -12.0000 -0.3886 -0.8966 0.1658
-6 21 -2 0.0557 -6.0000 21.0000 -2.0000 -0.3946 -0.7991 -0.4764
4 -20 -2 0.1196 4.0000 -20.0000 -2.0000 0.3119 0.6713 0.6970
8 -20 8 0.0691 8.0000 -20.0000 8.0000 0.4477 0.8954 0.0895
2 21 -17 0.0695 2.0000 21.0000 -17.0000 0.3967 -0.9243 -0.1301



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method Ethanol
_chemical_properties_physical    Hygroscopic
####################################################################### 
# 
# 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_AP1347
_database_code_depnum_ccdc_archive 'CCDC 1478547'
_audit_update_record             
;
2016-05-06 deposited with the CCDC.
2016-07-07 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            'C32 H68 Ca4 Cl8 N4 O12'
_chemical_formula_weight         1144.82

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.2400(6)
_cell_length_b                   9.9217(7)
_cell_length_c                   15.7248(10)
_cell_angle_alpha                72.942(6)
_cell_angle_beta                 89.180(5)
_cell_angle_gamma                74.421(6)
_cell_volume                     1324.29(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2378
_cell_measurement_theta_max      32.6813
_cell_measurement_theta_min      2.2298

_exptl_crystal_description       trapezoid
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2903
_exptl_crystal_size_mid          0.2057
_exptl_crystal_size_min          0.0683
_exptl_absorpt_coefficient_mu    0.866
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.838
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0646378000
_diffrn_orient_matrix_UB_12      0.0265005000
_diffrn_orient_matrix_UB_13      -0.0044432000
_diffrn_orient_matrix_UB_21      -0.0458001000
_diffrn_orient_matrix_UB_22      0.0706987000
_diffrn_orient_matrix_UB_23      -0.0014469000
_diffrn_orient_matrix_UB_31      0.0103150000
_diffrn_orient_matrix_UB_32      -0.0188292000
_diffrn_orient_matrix_UB_33      0.0470677000
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11341
_diffrn_reflns_av_unetI/netI     0.1002
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.234
_diffrn_reflns_theta_max         25.997
_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             5215
_reflns_number_gt                3562
_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_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0308P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5215
_refine_ls_number_parameters     293
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_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
Ca1 Ca 0.78315(8) 0.03501(8) 0.04825(5) 0.01639(19) Uani 1 1 d . . . . .
Ca2 Ca 0.98562(9) -0.09871(9) 0.35039(5) 0.0214(2) Uani 1 1 d D . . . .
Cl2 Cl 1.04272(10) -0.19223(10) 0.06317(6) 0.0195(2) Uani 1 1 d . . . . .
Cl1 Cl 0.65292(10) -0.16539(11) 0.15670(6) 0.0215(2) Uani 1 1 d . . . . .
Cl3 Cl 0.86704(10) 0.10422(11) 0.19224(6) 0.0227(2) Uani 1 1 d . . . . .
Cl4 Cl 1.21074(11) 0.01816(12) 0.37426(6) 0.0280(3) Uani 1 1 d . . . . .
O1 O 0.5693(3) 0.2239(3) 0.02197(16) 0.0215(6) Uani 1 1 d . . . . .
O4 O 0.8176(3) 0.0392(3) 0.42744(18) 0.0273(7) Uani 1 1 d . . . . .
O2 O 0.6741(3) 0.0030(3) -0.07598(17) 0.0222(7) Uani 1 1 d . . . . .
O3 O 1.0469(3) -0.2785(3) 0.48497(16) 0.0304(7) Uani 1 1 d . . . . .
O6 O 1.1318(3) -0.2491(3) 0.26912(16) 0.0276(7) Uani 1 1 d D . . . .
H6 H 1.108(3) -0.239(4) 0.2135(11) 0.041 Uiso 1 1 d D U . . .
O5 O 0.7810(3) -0.1956(4) 0.34138(17) 0.0371(8) Uani 1 1 d D . . . .
H5 H 0.751(3) -0.201(5) 0.2907(12) 0.056 Uiso 1 1 d D U . . .
N1 N 0.3335(3) 0.2944(3) 0.06882(18) 0.0185(7) Uani 1 1 d . . . . .
N2 N 1.1805(4) -0.3420(4) 0.61854(19) 0.0234(8) Uani 1 1 d . . . . .
C2 C 0.3777(4) 0.4418(4) -0.0673(2) 0.0210(9) Uani 1 1 d . . . . .
H2A H 0.3895 0.4162 -0.1238 0.025 Uiso 1 1 calc R U . . .
H2B H 0.4299 0.5178 -0.0696 0.025 Uiso 1 1 calc R U . . .
C4 C 0.1899(4) 0.4069(4) 0.0386(2) 0.0262(10) Uani 1 1 d . . . . .
H4A H 0.1649 0.4688 0.0789 0.031 Uiso 1 1 calc R U . . .
H4B H 0.1074 0.3615 0.0364 0.031 Uiso 1 1 calc R U . . .
C1 C 0.4390(4) 0.3089(4) 0.0109(2) 0.0197(9) Uani 1 1 d . . . . .
C5 C 0.3510(4) 0.1742(4) 0.1510(2) 0.0214(9) Uani 1 1 d . . . . .
H5A H 0.3115 0.2144 0.2000 0.026 Uiso 1 1 calc R U . . .
H5B H 0.4595 0.1236 0.1662 0.026 Uiso 1 1 calc R U . . .
C7 C 1.0625(5) -0.3321(4) 0.5672(3) 0.0259(10) Uani 1 1 d . . . . .
C6 C 0.2694(4) 0.0642(4) 0.1436(2) 0.0244(9) Uani 1 1 d . . . . .
H6A H 0.2810 -0.0128 0.2017 0.029 Uiso 1 1 calc R U . . .
H6B H 0.1606 0.1144 0.1294 0.029 Uiso 1 1 calc R U . . .
C12 C 1.3166(4) -0.1559(4) 0.6061(3) 0.0280(10) Uani 1 1 d . . . . .
H12A H 1.3296 -0.1782 0.6716 0.034 Uiso 1 1 calc R U . . .
H12B H 1.4048 -0.1249 0.5798 0.034 Uiso 1 1 calc R U . . .
C11 C 1.3094(4) -0.2918(5) 0.5839(2) 0.0264(10) Uani 1 1 d . . . . .
H11A H 1.3045 -0.2710 0.5183 0.032 Uiso 1 1 calc R U . . .
H11B H 1.4028 -0.3710 0.6088 0.032 Uiso 1 1 calc R U . . .
C10 C 1.1749(4) -0.4177(5) 0.7133(2) 0.0266(10) Uani 1 1 d . . . . .
H10A H 1.1989 -0.3617 0.7513 0.032 Uiso 1 1 calc R U . . .
H10B H 1.2458 -0.5174 0.7310 0.032 Uiso 1 1 calc R U . . .
C8 C 0.9554(5) -0.4033(5) 0.6248(2) 0.0312(10) Uani 1 1 d . . . . .
H8A H 0.9590 -0.4987 0.6157 0.037 Uiso 1 1 calc R U . . .
H8B H 0.8508 -0.3392 0.6112 0.037 Uiso 1 1 calc R U . . .
C9 C 1.0110(5) -0.4243(5) 0.7198(2) 0.0334(11) Uani 1 1 d . . . . .
H9A H 1.0055 -0.5202 0.7600 0.040 Uiso 1 1 calc R U . . .
H9B H 0.9501 -0.3454 0.7426 0.040 Uiso 1 1 calc R U . . .
C15 C 1.2891(5) -0.3287(5) 0.2875(3) 0.0384(11) Uani 1 1 d D . . . .
H15A H 1.3094 -0.3761 0.3526 0.046 Uiso 1 1 calc R U . . .
H15B H 1.3503 -0.2582 0.2692 0.046 Uiso 1 1 calc R U . . .
C14 C 0.6394(6) -0.3482(6) 0.4319(3) 0.0558(15) Uani 1 1 d . . . . .
H14A H 0.6084 -0.3735 0.3806 0.084 Uiso 1 1 calc R U . . .
H14B H 0.5621 -0.3519 0.4752 0.084 Uiso 1 1 calc R U . . .
H14C H 0.7351 -0.4184 0.4600 0.084 Uiso 1 1 calc R U . . .
C16 C 1.3379(5) -0.4427(5) 0.2414(3) 0.0467(14) Uani 1 1 d . . . . .
H16A H 1.3215 -0.3964 0.1767 0.070 Uiso 1 1 calc R U . . .
H16B H 1.2792 -0.5141 0.2599 0.070 Uiso 1 1 calc R U . . .
H16C H 1.4451 -0.4929 0.2570 0.070 Uiso 1 1 calc R U . . .
C3 C 0.2133(6) 0.4951(6) -0.0520(3) 0.082(2) Uani 1 1 d . . . . .
H3A H 0.1864 0.6005 -0.0562 0.098 Uiso 1 1 calc R U . . .
H3B H 0.1495 0.4821 -0.0973 0.098 Uiso 1 1 calc R U . . .
C13 C 0.6585(6) -0.2000(6) 0.4020(3) 0.0444(13) Uani 1 1 d D . . . .
H13A H 0.680(5) -0.177(5) 0.462(3) 0.053 Uiso 1 1 d . U . . .
H13B H 0.558(5) -0.128(5) 0.376(3) 0.053 Uiso 1 1 d . U . . .
H4 H 0.815(5) 0.020(5) 0.483(3) 0.052(15) Uiso 1 1 d . . . . .
H2 H 0.591(4) 0.046(4) -0.091(2) 0.006(10) Uiso 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 O1 2.273(3) . ?
Ca1 O2 2.351(3) . ?
Ca1 Cl3 2.7289(11) . ?
Ca1 Cl1 2.7471(12) . ?
Ca1 Cl2 2.7734(11) . ?
Ca1 Cl2 2.7850(12) 2_755 ?
Ca1 Ca1 4.2182(14) 2_755 ?
Ca2 O3 2.293(3) . ?
Ca2 O4 2.351(3) . ?
Ca2 O5 2.363(3) . ?
Ca2 O6 2.381(2) . ?
Ca2 Cl4 2.7176(13) . ?
Ca2 Cl3 2.7193(12) . ?
Cl2 Ca1 2.7849(12) 2_755 ?
O1 C1 1.251(4) . ?
O4 C12 1.431(4) 2_756 ?
O2 C6 1.435(4) 2_655 ?
O3 C7 1.240(4) . ?
O6 C15 1.443(5) . ?
O5 C13 1.471(5) . ?
N1 C1 1.331(4) . ?
N1 C5 1.455(4) . ?
N1 C4 1.464(4) . ?
N2 C7 1.331(5) . ?
N2 C11 1.452(5) . ?
N2 C10 1.466(4) . ?
C2 C1 1.497(5) . ?
C2 C3 1.509(6) . ?
C4 C3 1.484(6) . ?
C5 C6 1.514(5) . ?
C7 C8 1.507(6) . ?
C6 O2 1.435(4) 2_655 ?
C12 O4 1.431(4) 2_756 ?
C12 C11 1.507(5) . ?
C10 C9 1.534(5) . ?
C8 C9 1.524(5) . ?
C15 C16 1.486(6) . ?
C14 C13 1.465(7) . ?

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 Ca1 O2 80.41(9) . . ?
O1 Ca1 Cl3 90.57(7) . . ?
O2 Ca1 Cl3 170.87(8) . . ?
O1 Ca1 Cl1 94.28(7) . . ?
O2 Ca1 Cl1 88.73(8) . . ?
Cl3 Ca1 Cl1 90.53(3) . . ?
O1 Ca1 Cl2 174.59(7) . . ?
O2 Ca1 Cl2 94.87(7) . . ?
Cl3 Ca1 Cl2 94.20(4) . . ?
Cl1 Ca1 Cl2 88.24(4) . . ?
O1 Ca1 Cl2 96.01(7) . 2_755 ?
O2 Ca1 Cl2 90.04(7) . 2_755 ?
Cl3 Ca1 Cl2 92.35(4) . 2_755 ?
Cl1 Ca1 Cl2 169.29(4) . 2_755 ?
Cl2 Ca1 Cl2 81.27(4) . 2_755 ?
O1 Ca1 Ca1 136.35(7) . 2_755 ?
O2 Ca1 Ca1 93.22(7) . 2_755 ?
Cl3 Ca1 Ca1 94.31(3) . 2_755 ?
Cl1 Ca1 Ca1 128.94(4) . 2_755 ?
Cl2 Ca1 Ca1 40.73(2) . 2_755 ?
Cl2 Ca1 Ca1 40.53(2) 2_755 2_755 ?
O3 Ca2 O4 86.03(10) . . ?
O3 Ca2 O5 84.47(10) . . ?
O4 Ca2 O5 82.50(10) . . ?
O3 Ca2 O6 93.98(10) . . ?
O4 Ca2 O6 173.24(10) . . ?
O5 Ca2 O6 90.76(10) . . ?
O3 Ca2 Cl4 93.00(8) . . ?
O4 Ca2 Cl4 92.83(8) . . ?
O5 Ca2 Cl4 174.82(7) . . ?
O6 Ca2 Cl4 93.93(7) . . ?
O3 Ca2 Cl3 170.28(8) . . ?
O4 Ca2 Cl3 90.41(8) . . ?
O5 Ca2 Cl3 86.11(8) . . ?
O6 Ca2 Cl3 88.50(7) . . ?
Cl4 Ca2 Cl3 96.20(4) . . ?
Ca1 Cl2 Ca1 98.73(4) . 2_755 ?
Ca2 Cl3 Ca1 123.61(4) . . ?
C1 O1 Ca1 169.0(3) . . ?
C12 O4 Ca2 129.1(2) 2_756 . ?
C6 O2 Ca1 134.9(2) 2_655 . ?
C7 O3 Ca2 157.5(3) . . ?
C15 O6 Ca2 126.6(2) . . ?
C13 O5 Ca2 126.6(3) . . ?
C1 N1 C5 124.9(3) . . ?
C1 N1 C4 113.1(3) . . ?
C5 N1 C4 121.8(3) . . ?
C7 N2 C11 123.4(3) . . ?
C7 N2 C10 114.3(3) . . ?
C11 N2 C10 122.1(3) . . ?
C1 C2 C3 104.6(3) . . ?
N1 C4 C3 104.9(3) . . ?
O1 C1 N1 124.3(4) . . ?
O1 C1 C2 126.1(3) . . ?
N1 C1 C2 109.6(3) . . ?
N1 C5 C6 112.3(3) . . ?
O3 C7 N2 125.2(4) . . ?
O3 C7 C8 125.8(4) . . ?
N2 C7 C8 108.9(3) . . ?
O2 C6 C5 112.0(3) 2_655 . ?
O4 C12 C11 110.9(3) 2_756 . ?
N2 C11 C12 112.6(3) . . ?
N2 C10 C9 102.9(3) . . ?
C7 C8 C9 104.4(3) . . ?
C8 C9 C10 105.0(3) . . ?
O6 C15 C16 113.6(3) . . ?
C4 C3 C2 107.2(4) . . ?
C14 C13 O5 109.9(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H6 Cl2 0.873(9) 2.328(10) 3.200(3) 176(3) .
O5 H5 Cl1 0.871(9) 2.195(14) 3.053(3) 168(4) .
O4 H4 Cl4 0.83(4) 2.19(4) 3.022(3) 175(4) 2_756
O2 H2 Cl1 0.77(3) 2.34(3) 3.104(3) 171(3) 2_655

_refine_diff_density_max         0.755
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.090

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4 -2 20 0.0727 -4.0000 -2.0000 20.0000 -0.4004 0.0129 0.9378
10 5 -11 0.0801 10.0000 5.0000 -11.0000 0.8278 -0.0886 -0.5087
11 6 11 0.1521 11.0000 6.0000 11.0000 0.8211 -0.0955 0.5182
-9 -5 -16 0.1090 -9.0000 -5.0000 -16.0000 -0.6432 0.0819 -0.7518
1 13 1 0.0299 1.0000 13.0000 1.0000 0.4047 0.8718 -0.1874
-1 -13 1 0.0254 -1.0000 -13.0000 1.0000 -0.4136 -0.8747 0.2815
-13 -2 5 0.0946 -13.0000 -2.0000 5.0000 -0.9155 0.4468 0.1389



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method Ethanol
####################################################################### 
# 
# 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_ap82_2
_database_code_depnum_ccdc_archive 'CCDC 1478548'
_audit_update_record             
;
2016-07-05 deposited with the CCDC.
2016-07-07 downloaded from the CCDC.
;
_audit_creation_date             2014-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H30 Ca N2 O8, 2(Cl), H2 O'
_chemical_formula_sum            'C12 H32 Ca Cl2 N2 O9'
_chemical_formula_weight         459.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         CaCl2C12H32O9N2
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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.8007(5)
_cell_length_b                   8.9311(5)
_cell_length_c                   14.7500(8)
_cell_angle_alpha                99.325(5)
_cell_angle_beta                 95.103(4)
_cell_angle_gamma                104.163(5)
_cell_volume                     1099.18(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3965
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.4757
_cell_measurement_theta_min      2.6181
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.4521
_exptl_crystal_size_mid          0.3035
_exptl_crystal_size_min          0.1295
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8493
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.62
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 16.1511
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -91.00   42.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429    0.0000 -120.0000 133

#__ type_ start__ end____ width___ exp.time_
  2 omega -100.00  -66.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429 -179.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
  3 omega  -95.00  -14.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429  -38.0000   30.0000 81

#__ type_ start__ end____ width___ exp.time_
  4 omega -100.00  -41.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429 -179.0000  150.0000 59

#__ type_ start__ end____ width___ exp.time_
  5 omega   56.00   81.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679  179.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00   79.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679 -122.0000   34.0000 56

#__ type_ start__ end____ width___ exp.time_
  7 omega   20.00   82.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679 -122.0000 -145.0000 62
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0049377000
_diffrn_orient_matrix_UB_12      0.0786415000
_diffrn_orient_matrix_UB_13      0.0122795000
_diffrn_orient_matrix_UB_21      -0.0034995000
_diffrn_orient_matrix_UB_22      0.0069688000
_diffrn_orient_matrix_UB_23      -0.0473168000
_diffrn_orient_matrix_UB_31      -0.0836655000
_diffrn_orient_matrix_UB_32      -0.0269840000
_diffrn_orient_matrix_UB_33      -0.0053728000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3745
_reflns_number_total             4306
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0395P)²+0.7921P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0954
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O6S(H6SA,H6SB)
2.b Rotating group:
 O1S(H1SA,H1SB), O4S(H4SA,H4SB), O5S(H5SA,H5SB), O2S(H2SA,H2SB), O3S(H3SA,H3SB)
2.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B), C8(H8A,H8B), C7(H7A,H7B), C2(H2A,H2B), C4(H4A,H4B),
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C3(H3A,H3B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Ca1 Ca 0.12529(5) 0.18038(5) 0.29170(3) 0.01196(12) Uani 1 1 d . . .
Cl1 Cl 0.11631(6) 0.71216(6) 0.41166(4) 0.01842(13) Uani 1 1 d . . .
O1S O 0.07608(18) 0.35734(18) 0.41852(10) 0.0198(3) Uani 1 1 d . . .
H1SA H 0.0302 0.3291 0.4684 0.030 Uiso 1 1 d . . GR
H1SB H 0.1001 0.4640 0.4248 0.030 Uiso 1 1 d . . GR
O4S O 0.11292(18) 0.12901(18) 0.12499(10) 0.0185(3) Uani 1 1 d . . .
H4SA H 0.1483 0.0541 0.0917 0.028 Uiso 1 1 d . . GR
H4SB H 0.0722 0.1818 0.0864 0.028 Uiso 1 1 d . . GR
O1 O 0.40281(17) 0.25182(18) 0.30244(11) 0.0188(3) Uani 1 1 d . . .
O2 O 0.64930(16) 0.74651(17) 0.39277(10) 0.0158(3) Uani 1 1 d . . .
O5S O 0.1671(2) 0.43654(19) 0.24858(11) 0.0239(4) Uani 1 1 d . . .
H5SA H 0.1096 0.4913 0.2784 0.036 Uiso 1 1 d . . GR
H5SB H 0.1394 0.4256 0.1884 0.036 Uiso 1 1 d . . GR
O2S O 0.1498(2) 0.07656(19) 0.43426(11) 0.0238(4) Uani 1 1 d . . .
H2SA H 0.0674 -0.0016 0.4338 0.036 Uiso 1 1 d . . GR
H2SB H 0.1556 0.1506 0.4822 0.036 Uiso 1 1 d . . GR
N1 N 0.6361(2) 0.4257(2) 0.29330(12) 0.0157(4) Uani 1 1 d . . .
O6S O 0.2158(2) 0.4866(2) 0.07371(12) 0.0254(4) Uani 1 1 d . . .
H6SA H 0.2031 0.5770 0.0648 0.038 Uiso 1 1 d . . G
H6SB H 0.1409 0.4113 0.0393 0.038 Uiso 1 1 d . . G
N2 N 0.6094(2) 0.9374(2) 0.25846(12) 0.0173(4) Uani 1 1 d . . .
O3S O 0.1034(2) -0.09704(19) 0.24893(11) 0.0307(4) Uani 1 1 d . . .
H3SA H 0.1001 -0.1618 0.2875 0.046 Uiso 1 1 d . . GR
H3SB H 0.0974 -0.1481 0.1925 0.046 Uiso 1 1 d . . GR
O3 O 0.85094(18) 1.1048(2) 0.26196(12) 0.0269(4) Uani 1 1 d . . .
C6 C 0.5908(3) 0.6050(3) 0.42728(15) 0.0171(4) Uani 1 1 d . . .
H6A H 0.4762 0.5619 0.4058 0.021 Uiso 1 1 calc . . R
H6B H 0.6065 0.6282 0.4959 0.021 Uiso 1 1 calc . . R
C1 C 0.5044(2) 0.3148(3) 0.25638(15) 0.0151(4) Uani 1 1 d . . .
C5 C 0.6785(2) 0.4857(3) 0.39254(15) 0.0168(4) Uani 1 1 d . . .
H5A H 0.7937 0.5353 0.4061 0.020 Uiso 1 1 calc . . R
H5B H 0.6539 0.3970 0.4260 0.020 Uiso 1 1 calc . . R
C9 C 0.7369(2) 0.9982(3) 0.22024(15) 0.0187(5) Uani 1 1 d . . .
C8 C 0.5968(3) 0.9830(3) 0.35623(15) 0.0213(5) Uani 1 1 d . . .
H8A H 0.5215 1.0491 0.3626 0.026 Uiso 1 1 calc . . R
H8B H 0.7013 1.0470 0.3890 0.026 Uiso 1 1 calc . . R
C7 C 0.5415(3) 0.8425(3) 0.40104(16) 0.0213(5) Uani 1 1 d . . .
H7A H 0.5349 0.8784 0.4673 0.026 Uiso 1 1 calc . . R
H7B H 0.4347 0.7806 0.3706 0.026 Uiso 1 1 calc . . R
C2 C 0.5012(3) 0.2786(3) 0.15309(16) 0.0233(5) Uani 1 1 d . . .
H2A H 0.4043 0.2944 0.1211 0.028 Uiso 1 1 calc . . R
H2B H 0.5046 0.1685 0.1323 0.028 Uiso 1 1 calc . . R
C4 C 0.7396(3) 0.4769(3) 0.22557(16) 0.0256(5) Uani 1 1 d . . .
H4A H 0.8403 0.4473 0.2353 0.031 Uiso 1 1 calc . . R
H4B H 0.7632 0.5922 0.2300 0.031 Uiso 1 1 calc . . R
C10 C 0.7162(3) 0.9177(3) 0.12037(16) 0.0274(6) Uani 1 1 d . . .
H10A H 0.7877 0.8481 0.1113 0.033 Uiso 1 1 calc . . R
H10B H 0.7384 0.9959 0.0795 0.033 Uiso 1 1 calc . . R
C11 C 0.5430(3) 0.8221(3) 0.10002(16) 0.0280(6) Uani 1 1 d . . .
H11A H 0.5332 0.7159 0.0638 0.034 Uiso 1 1 calc . . R
H11B H 0.4787 0.8755 0.0647 0.034 Uiso 1 1 calc . . R
C12 C 0.4892(3) 0.8116(3) 0.19554(16) 0.0250(5) Uani 1 1 d . . .
H12A H 0.3828 0.8295 0.1974 0.030 Uiso 1 1 calc . . R
H12B H 0.4873 0.7077 0.2115 0.030 Uiso 1 1 calc . . R
C3 C 0.6465(3) 0.3918(4) 0.13318(18) 0.0393(7) Uani 1 1 d . . .
H3A H 0.7103 0.3342 0.0964 0.047 Uiso 1 1 calc . . R
H3B H 0.6160 0.4675 0.0977 0.047 Uiso 1 1 calc . . R
Cl2 Cl 0.09360(7) 0.77948(7) 0.03605(4) 0.02338(14) 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 O1S 2.3886(16) . ?
Ca1 O4S 2.4148(15) . ?
Ca1 O1 2.3523(15) . ?
Ca1 O5S 2.4239(16) . ?
Ca1 O2S 2.4447(16) . ?
Ca1 O3S 2.4108(17) . ?
Ca1 O3 2.3229(16) 1_445 ?
O1 C1 1.250(3) . ?
O2 C6 1.435(3) . ?
O2 C7 1.427(3) . ?
N1 C1 1.332(3) . ?
N1 C5 1.456(3) . ?
N1 C4 1.464(3) . ?
N2 C9 1.336(3) . ?
N2 C8 1.455(3) . ?
N2 C12 1.466(3) . ?
O3 Ca1 2.3229(16) 1_665 ?
O3 C9 1.235(3) . ?
C6 C5 1.512(3) . ?
C1 C2 1.502(3) . ?
C9 C10 1.505(3) . ?
C8 C7 1.509(3) . ?
C2 C3 1.507(3) . ?
C4 C3 1.506(3) . ?
C10 C11 1.530(3) . ?
C11 C12 1.535(3) . ?

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
O1S Ca1 O4S 142.76(6) . . ?
O1S Ca1 O5S 72.41(5) . . ?
O1S Ca1 O2S 70.17(5) . . ?
O1S Ca1 O3S 138.01(6) . . ?
O4S Ca1 O5S 75.00(5) . . ?
O4S Ca1 O2S 146.36(6) . . ?
O1 Ca1 O1S 103.00(6) . . ?
O1 Ca1 O4S 88.54(5) . . ?
O1 Ca1 O5S 80.17(6) . . ?
O1 Ca1 O2S 88.66(6) . . ?
O1 Ca1 O3S 93.76(6) . . ?
O5S Ca1 O2S 137.21(6) . . ?
O3S Ca1 O4S 74.67(6) . . ?
O3S Ca1 O5S 149.19(6) . . ?
O3S Ca1 O2S 72.08(6) . . ?
O3 Ca1 O1S 82.52(6) 1_445 . ?
O3 Ca1 O4S 84.60(6) 1_445 . ?
O3 Ca1 O1 173.13(6) 1_445 . ?
O3 Ca1 O5S 97.87(6) 1_445 . ?
O3 Ca1 O2S 97.13(6) 1_445 . ?
O3 Ca1 O3S 84.56(6) 1_445 . ?
C1 O1 Ca1 136.98(14) . . ?
C7 O2 C6 110.49(16) . . ?
C1 N1 C5 123.38(17) . . ?
C1 N1 C4 114.00(18) . . ?
C5 N1 C4 122.54(18) . . ?
C9 N2 C8 122.77(19) . . ?
C9 N2 C12 114.29(19) . . ?
C8 N2 C12 122.74(18) . . ?
C9 O3 Ca1 143.37(16) . 1_665 ?
O2 C6 C5 109.31(16) . . ?
O1 C1 N1 124.1(2) . . ?
O1 C1 C2 126.85(19) . . ?
N1 C1 C2 109.04(18) . . ?
N1 C5 C6 111.98(17) . . ?
N2 C9 C10 109.13(19) . . ?
O3 C9 N2 124.0(2) . . ?
O3 C9 C10 126.8(2) . . ?
N2 C8 C7 112.19(19) . . ?
O2 C7 C8 109.79(17) . . ?
C1 C2 C3 105.37(19) . . ?
N1 C4 C3 104.30(18) . . ?
C9 C10 C11 104.71(19) . . ?
C10 C11 C12 105.13(18) . . ?
N2 C12 C11 103.37(18) . . ?
C4 C3 C2 106.8(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5S H5SB O6S 0.88 1.98 2.741(2) 143.2 .

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-12 -2 3 0.2031 -11.9921 -1.9989 2.9909 -0.0613 -0.1135 1.0412
12 2 -3 0.2031 11.9921 1.9989 -2.9909 0.0613 0.1135 -1.0412
-1 6 -20 0.0919 -1.0012 5.9966 -19.9694 0.2313 0.9902 0.0292
1 -6 20 0.1083 1.0012 -5.9966 19.9694 -0.2313 -0.9902 -0.0292
1 7 15 0.0617 0.9935 6.9963 14.9744 0.7292 -0.6633 -0.3524
-7 6 15 0.0835 -7.0012 5.9968 14.9715 0.6900 -0.6421 0.3435
2 -7 -16 0.0558 2.0048 -6.9963 -15.9716 -0.7562 0.7000 0.1069

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
