# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1496609'
_audit_update_record             
;
2016-07-29 deposited with the CCDC.
2016-10-03 downloaded from the CCDC.
;
_audit_creation_date             2016-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.25(C32 H16 Br8 Ca4 O20)'
_chemical_formula_sum            'C8 H4 Br2 Ca O5'
_chemical_formula_weight         380.01
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 N1 O1 Zn1'
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'
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                   15.6300(11)
_cell_length_b                   12.6171(7)
_cell_length_c                   5.4481(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.926(7)
_cell_angle_gamma                90
_cell_volume                     1072.99(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    677
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.6340
_cell_measurement_theta_min      4.1550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.033
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            1829
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.610
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.5095
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0325639000
_diffrn_orient_matrix_UB_12      0.0390026000
_diffrn_orient_matrix_UB_13      0.0147978000
_diffrn_orient_matrix_UB_21      -0.0295548000
_diffrn_orient_matrix_UB_22      0.0395423000
_diffrn_orient_matrix_UB_23      -0.0415175000
_diffrn_orient_matrix_UB_31      -0.0114484000
_diffrn_orient_matrix_UB_32      0.0086909000
_diffrn_orient_matrix_UB_33      0.1226839000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                811
_reflns_number_total             944
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.733
_refine_diff_density_min         -1.364
_refine_diff_density_rms         0.130
_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     75
_refine_ls_number_reflns         944
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.096
_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)+(0.0370P)²+3.6780P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0896
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: H3A(0.5) H3B(0.5)
3.a Rotating group:
 O3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.64020(4) 0.60436(4) 0.86798(11) 0.0418(3) Uani 1 1 d . . . . .
Ca1 Ca 0.5000 1.08987(10) 0.7500 0.0130(3) Uani 1 2 d S T P . .
O1 O 0.58026(19) 0.9356(2) 0.6226(5) 0.0150(7) Uani 1 1 d . . . . .
O2 O 0.6021(2) 0.8424(2) 0.9701(5) 0.0213(8) Uani 1 1 d . . . . .
C3 C 0.7032(3) 0.6934(4) 0.6612(8) 0.0171(10) Uani 1 1 d . . . . .
C2 C 0.6843(3) 0.8005(4) 0.6257(8) 0.0141(9) Uani 1 1 d . . . . .
C1 C 0.6163(3) 0.8627(3) 0.7523(8) 0.0134(9) Uani 1 1 d . . . . .
C4 C 0.7325(3) 0.8553(4) 0.4617(8) 0.0178(10) Uani 1 1 d . . . . .
H4 H 0.7213 0.9268 0.4334 0.021 Uiso 1 1 calc R U . . .
O3 O 0.5000 1.2775(4) 0.7500 0.065(2) Uani 1 2 d S T P . .
H3A H 0.4604 1.3164 0.8019 0.098 Uiso 0.5 1 d R U P . .
H3B H 0.5396 1.3164 0.6981 0.098 Uiso 0.5 1 d R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.901(4) . ?
Ca1 Ca1 3.5445(16) 5_676 ?
Ca1 Ca1 3.5445(16) 5_677 ?
Ca1 O1 2.436(3) . ?
Ca1 O1 2.353(3) 6_576 ?
Ca1 O1 2.353(3) 5_676 ?
Ca1 O1 2.436(3) 2_656 ?
Ca1 O2 2.419(3) 6_575 ?
Ca1 O2 2.419(3) 5_677 ?
Ca1 O3 2.368(5) . ?
O1 Ca1 2.353(3) 5_676 ?
O1 C1 1.273(5) . ?
O2 Ca1 2.419(3) 5_677 ?
O2 C1 1.245(5) . ?
C3 C2 1.394(6) . ?
C3 C4 1.380(6) 7_666 ?
C2 C1 1.516(6) . ?
C2 C4 1.383(6) . ?
C4 C3 1.380(6) 7_666 ?

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
Ca1 Ca1 Ca1 100.44(6) 5_676 5_677 ?
O1 Ca1 Ca1 74.22(8) . 5_677 ?
O1 Ca1 Ca1 123.68(9) 5_676 5_677 ?
O1 Ca1 Ca1 43.16(7) 6_576 5_677 ?
O1 Ca1 Ca1 41.37(7) 2_656 5_677 ?
O1 Ca1 Ca1 43.16(7) 5_676 5_676 ?
O1 Ca1 Ca1 123.68(9) 6_576 5_676 ?
O1 Ca1 Ca1 41.37(7) . 5_676 ?
O1 Ca1 Ca1 74.22(8) 2_656 5_676 ?
O1 Ca1 O1 84.52(11) 5_676 . ?
O1 Ca1 O1 73.92(14) 2_656 . ?
O1 Ca1 O1 82.93(10) 6_576 . ?
O1 Ca1 O1 82.93(10) 5_676 2_656 ?
O1 Ca1 O1 84.52(11) 6_576 2_656 ?
O1 Ca1 O1 164.28(16) 5_676 6_576 ?
O1 Ca1 O2 81.04(10) 5_676 6_575 ?
O1 Ca1 O2 104.61(11) 6_576 6_575 ?
O1 Ca1 O2 104.61(11) 5_676 5_677 ?
O1 Ca1 O2 81.04(10) 6_576 5_677 ?
O1 Ca1 O3 97.86(8) 5_676 . ?
O1 Ca1 O3 97.86(8) 6_576 . ?
O2 Ca1 Ca1 137.42(8) 5_677 5_676 ?
O2 Ca1 Ca1 73.47(7) 5_677 5_677 ?
O2 Ca1 Ca1 137.42(8) 6_575 5_677 ?
O2 Ca1 Ca1 73.47(7) 6_575 5_676 ?
O2 Ca1 O1 145.88(11) 6_575 2_656 ?
O2 Ca1 O1 74.72(10) 5_677 2_656 ?
O2 Ca1 O1 145.88(11) 5_677 . ?
O2 Ca1 O1 74.72(10) 6_575 . ?
O2 Ca1 O2 138.64(16) 6_575 5_677 ?
O3 Ca1 Ca1 129.78(3) . 5_677 ?
O3 Ca1 Ca1 129.78(3) . 5_676 ?
O3 Ca1 O1 143.04(7) . . ?
O3 Ca1 O1 143.04(7) . 2_656 ?
O3 Ca1 O2 69.32(8) . 6_575 ?
O3 Ca1 O2 69.32(8) . 5_677 ?
Ca1 O1 Ca1 95.48(11) 5_676 . ?
C1 O1 Ca1 129.7(3) . . ?
C1 O1 Ca1 125.5(3) . 5_676 ?
C1 O2 Ca1 133.1(3) . 5_677 ?
C2 C3 Br1 122.9(3) . . ?
C4 C3 Br1 115.8(3) 7_666 . ?
C4 C3 C2 121.2(4) 7_666 . ?
C3 C2 C1 125.9(4) . . ?
C4 C2 C3 117.1(4) . . ?
C4 C2 C1 117.0(4) . . ?
O1 C1 C2 115.0(3) . . ?
O2 C1 O1 125.6(4) . . ?
O2 C1 C2 119.4(4) . . ?
C3 C4 C2 121.7(4) 7_666 . ?

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1496610'
_audit_update_record             
;
2016-07-29 deposited with the CCDC.
2016-10-03 downloaded from the CCDC.
;
_audit_creation_date             2016-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.5(C80 H60 Br8 Ca2 N8 O16)'
_chemical_formula_sum            'C40 H30 Br4 Ca N4 O8'
_chemical_formula_weight         1054.40
_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'
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           48
_space_group_name_H-M_alt        'P n n n'
_space_group_name_Hall           '-P 2ab 2bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y, -z+1/2'
'x, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x-1/2, -y, z-1/2'
'-x, y-1/2, z-1/2'

_cell_length_a                   11.0693(5)
_cell_length_b                   12.9647(3)
_cell_length_c                   13.6267(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1955.57(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2386
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8700
_cell_measurement_theta_min      3.6730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.306
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86799
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5704
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.168
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1392
_reflns_number_total             1736
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.787
_refine_diff_density_min         -0.821
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1736
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.035
_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)+(0.0331P)²+3.3151P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0864
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_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
Br1 Br 0.55011(6) 0.11477(3) 0.70840(3) 0.0680(2) Uani 1 1 d . . . . .
Ca1 Ca 0.2500 0.2500 0.2500 0.0274(3) Uani 1 4 d S T P . .
O1 O 0.4143(2) 0.13491(17) 0.27406(17) 0.0390(6) Uani 1 1 d . . . . .
N1 N 0.2089(3) 0.3474(2) 0.0778(2) 0.0352(7) Uani 1 1 d . . . . .
C3 C 0.5278(3) 0.1029(2) 0.5040(3) 0.0313(8) Uani 1 1 d . . . . .
H3 H 0.5468 0.1727 0.5080 0.038 Uiso 1 1 calc R U . . .
O2 O 0.6004(2) 0.1837(2) 0.3153(2) 0.0526(7) Uani 1 1 d . . . . .
C4 C 0.5235(3) 0.0448(2) 0.5887(2) 0.0315(7) Uani 1 1 d . . . . .
C1 C 0.5048(3) 0.1303(2) 0.3259(2) 0.0312(7) Uani 1 1 d . . . . .
C6 C 0.1694(3) 0.5096(3) -0.0015(3) 0.0404(9) Uani 1 1 d . . . . .
C8 C 0.2314(3) 0.3053(2) -0.0094(2) 0.0290(7) Uani 1 1 d . . . . .
C2 C 0.5045(3) 0.0598(2) 0.4137(2) 0.0275(7) Uani 1 1 d . . . . .
C7 C 0.1792(3) 0.4477(3) 0.0800(3) 0.0423(9) Uani 1 1 d . . . . .
H7 H 0.1642 0.4774 0.1410 0.051 Uiso 1 1 calc R U . . .
C9 C 0.2216(4) 0.3617(3) -0.0950(3) 0.0507(10) Uani 1 1 d . . . . .
H9 H 0.2357 0.3306 -0.1554 0.061 Uiso 1 1 calc R U . . .
C10 C 0.1905(4) 0.4648(3) -0.0901(3) 0.0514(10) Uani 1 1 d . . . . .
H10 H 0.1841 0.5036 -0.1473 0.062 Uiso 1 1 calc R U . . .
C5 C 0.1384(4) 0.6226(3) 0.0082(4) 0.0609(12) Uani 1 1 d . . . . .
H5A H 0.0525 0.6303 0.0147 0.091 Uiso 1 1 calc R U . . .
H5B H 0.1655 0.6589 -0.0491 0.091 Uiso 1 1 calc R U . . .
H5C H 0.1776 0.6505 0.0652 0.091 Uiso 1 1 calc R U . . .
H2 H 0.603(9) 0.2500 0.2500 0.15(3) Uiso 1 2 d S . 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
Br1 C4 1.889(3) . ?
Ca1 O1 2.375(2) 4 ?
Ca1 O1 2.375(2) 2 ?
Ca1 O1 2.375(2) . ?
Ca1 O1 2.375(2) 3 ?
Ca1 N1 2.703(3) 2 ?
Ca1 N1 2.703(3) 4 ?
Ca1 N1 2.703(3) . ?
Ca1 N1 2.703(3) 3 ?
O1 C1 1.227(4) . ?
N1 C8 1.332(4) . ?
N1 C7 1.341(4) . ?
C3 C4 1.379(4) . ?
C3 C2 1.376(5) . ?
O2 C1 1.273(4) . ?
C4 C2 1.392(4) 5_656 ?
C1 C2 1.507(4) . ?
C6 C7 1.375(5) . ?
C6 C10 1.360(5) . ?
C6 C5 1.511(5) . ?
C8 C8 1.492(6) 2 ?
C8 C9 1.381(5) . ?
C2 C4 1.391(4) 5_656 ?
C9 C10 1.382(5) . ?

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 O1 164.13(12) . 2 ?
O1 Ca1 O1 80.05(12) 3 2 ?
O1 Ca1 O1 102.17(11) 4 2 ?
O1 Ca1 O1 102.17(11) . 3 ?
O1 Ca1 O1 80.05(12) . 4 ?
O1 Ca1 O1 164.13(12) 3 4 ?
O1 Ca1 N1 92.56(8) 4 2 ?
O1 Ca1 N1 122.83(8) 2 2 ?
O1 Ca1 N1 73.48(9) 3 2 ?
O1 Ca1 N1 72.38(8) . 2 ?
O1 Ca1 N1 92.56(8) 2 4 ?
O1 Ca1 N1 122.83(8) 4 4 ?
O1 Ca1 N1 72.39(8) 3 4 ?
O1 Ca1 N1 73.48(9) . 4 ?
O1 Ca1 N1 92.56(8) . 3 ?
O1 Ca1 N1 92.56(8) 3 . ?
O1 Ca1 N1 73.48(9) 4 . ?
O1 Ca1 N1 72.38(8) 2 . ?
O1 Ca1 N1 122.83(8) . . ?
O1 Ca1 N1 73.48(9) 2 3 ?
O1 Ca1 N1 72.39(8) 4 3 ?
O1 Ca1 N1 122.83(8) 3 3 ?
N1 Ca1 N1 124.30(11) 2 4 ?
N1 Ca1 N1 59.55(11) 3 4 ?
N1 Ca1 N1 160.61(12) . 4 ?
N1 Ca1 N1 124.30(11) . 3 ?
N1 Ca1 N1 59.55(11) . 2 ?
N1 Ca1 N1 160.61(12) 3 2 ?
C1 O1 Ca1 137.3(2) . . ?
C8 N1 Ca1 123.50(19) . . ?
C8 N1 C7 117.6(3) . . ?
C7 N1 Ca1 118.3(2) . . ?
C2 C3 C4 121.3(3) . . ?
C3 C4 Br1 117.1(2) . . ?
C3 C4 C2 121.3(3) . 5_656 ?
C2 C4 Br1 121.6(2) 5_656 . ?
O1 C1 O2 126.0(3) . . ?
O1 C1 C2 119.0(3) . . ?
O2 C1 C2 114.9(3) . . ?
C7 C6 C5 120.9(4) . . ?
C10 C6 C7 117.0(3) . . ?
C10 C6 C5 122.1(4) . . ?
N1 C8 C8 116.46(17) . 2 ?
N1 C8 C9 121.5(3) . . ?
C9 C8 C8 122.1(2) . 2 ?
C3 C2 C4 117.3(3) . 5_656 ?
C3 C2 C1 117.6(3) . . ?
C4 C2 C1 125.0(3) 5_656 . ?
N1 C7 C6 124.6(3) . . ?
C8 C9 C10 119.4(4) . . ?
C6 C10 C9 119.9(3) . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_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_4
_database_code_depnum_ccdc_archive 'CCDC 1496611'
_audit_update_record             
;
2016-07-29 deposited with the CCDC.
2016-10-03 downloaded from the CCDC.
;
_audit_creation_date             2016-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C32 H16 Br8 Ca3 O20, C12 H12 N4, 2(H2 O)'
_chemical_formula_sum            'C44 H32 Br8 Ca3 N4 O22'
_chemical_formula_weight         1728.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 N1 O1 Zn1'
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'
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                   10.0545(6)
_cell_length_b                   11.5943(6)
_cell_length_c                   12.4010(7)
_cell_angle_alpha                74.417(5)
_cell_angle_beta                 84.716(5)
_cell_angle_gamma                83.300(5)
_cell_volume                     1380.20(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4656
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9990
_cell_measurement_theta_min      2.7240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.079
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9646
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.577
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.5095
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0296653000
_diffrn_orient_matrix_UB_12      0.0346896000
_diffrn_orient_matrix_UB_13      -0.0506579000
_diffrn_orient_matrix_UB_21      0.0631222000
_diffrn_orient_matrix_UB_22      -0.0327271000
_diffrn_orient_matrix_UB_23      0.0131891000
_diffrn_orient_matrix_UB_31      -0.0141896000
_diffrn_orient_matrix_UB_32      -0.0423871000
_diffrn_orient_matrix_UB_33      -0.0282851000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4001
_reflns_number_total             4844
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         1.045
_refine_diff_density_min         -0.925
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4844
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.044
_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)+(0.0310P)²+1.3190P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0791
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 N1-H1
 0.86 with sigma of 0.01
3.a Free rotating group:
 O11(H11A,H11B)
3.b Rotating group:
 O9(H9A), O10(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C16(H16), C21(H21), C18(H18), C11(H11), C22(H22), C8(H8), C19(H19),
 C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 1.40344(4) 0.17985(4) 1.16166(4) 0.04004(14) Uani 1 1 d . . . . .
Br2 Br 0.85291(5) 0.55836(4) 0.76398(4) 0.04182(14) Uani 1 1 d . . . . .
Br4 Br 0.60407(5) -0.28477(4) 0.53763(4) 0.04296(14) Uani 1 1 d . . . . .
Br3 Br 0.70450(4) 0.44954(4) 0.44194(5) 0.04360(14) Uani 1 1 d . . . . .
Ca1 Ca 1.04091(7) 0.08577(7) 0.81929(6) 0.01960(18) Uani 1 1 d . . . . .
Ca2 Ca 1.0000 0.0000 0.5000 0.0204(2) Uani 1 2 d S . P . .
O7 O 0.8456(3) -0.0107(3) 0.3773(2) 0.0289(7) Uani 1 1 d . . . . .
O8 O 0.7375(3) -0.1163(3) 0.2978(2) 0.0309(7) Uani 1 1 d . . . . .
O1 O 1.1347(3) 0.0415(3) 0.9942(3) 0.0426(8) Uani 1 1 d . . . . .
O4 O 0.9099(2) 0.2441(2) 0.9094(2) 0.0259(6) Uani 1 1 d . . . . .
O5 O 0.9334(3) 0.1958(3) 0.6603(3) 0.0368(7) Uani 1 1 d . . . . .
O2 O 1.1791(3) -0.0031(3) 1.1697(2) 0.0362(7) Uani 1 1 d . . . . .
O9 O 1.1304(3) -0.1220(3) 0.8600(3) 0.0340(7) Uani 1 1 d . . . . .
H9A H 1.1028 -0.1555 0.8142 0.051 Uiso 1 1 d R U . . .
O6 O 0.9222(3) 0.2047(3) 0.4814(3) 0.0438(8) Uani 1 1 d . . . . .
O3 O 1.1106(3) 0.2876(3) 0.8289(3) 0.0380(8) Uani 1 1 d . . . . .
O10 O 0.8569(4) -0.0898(4) 0.6502(3) 0.0675(12) Uani 1 1 d . . . . .
H2A H 0.7840 -0.1001 0.6258 0.101 Uiso 1 1 d R U . . .
H2B H 0.8401 -0.0440 0.6940 0.101 Uiso 1 1 d R U . . .
N2 N 0.5110(3) 0.3517(3) 0.8524(3) 0.0307(8) Uani 1 1 d . . . . .
O11 O 1.1569(5) -0.2877(4) 0.7369(3) 0.0749(13) Uani 1 1 d G . . . .
H11A H 1.1944 -0.3555 0.7307 0.112 Uiso 1 1 d G U . . .
H11B H 1.1079 -0.2565 0.6823 0.112 Uiso 1 1 d G U . . .
N1 N 0.4473(4) 0.2365(3) 0.7615(3) 0.0341(9) Uani 1 1 d D . . . .
C15 C 0.5450(4) -0.1183(3) 0.5109(3) 0.0247(9) Uani 1 1 d . . . . .
C20 C 0.5066(4) 0.4291(4) 0.9269(4) 0.0322(10) Uani 1 1 d . . . . .
C4 C 1.5911(4) 0.0565(4) 1.0391(3) 0.0235(9) Uani 1 1 d . . . . .
H4 H 1.6517 0.0947 1.0664 0.028 Uiso 1 1 calc R U . . .
C2 C 1.3623(4) 0.0154(3) 1.0326(3) 0.0206(8) Uani 1 1 d . . . . .
C16 C 0.5716(4) 0.0886(4) 0.4286(3) 0.0241(9) Uani 1 1 d . . . . .
H16 H 0.6189 0.1491 0.3815 0.029 Uiso 1 1 calc R U . . .
C13 C 0.7424(4) -0.0561(3) 0.3674(3) 0.0200(8) Uani 1 1 d . . . . .
C21 C 0.6100(4) 0.4165(4) 0.9964(4) 0.0381(11) Uani 1 1 d . . . . .
H21 H 0.6838 0.3609 0.9934 0.046 Uiso 1 1 calc R U . . .
C18 C 0.5837(4) 0.2337(4) 0.7431(4) 0.0379(11) Uani 1 1 d . . . . .
H18 H 0.6378 0.1906 0.6996 0.045 Uiso 1 1 calc R U . . .
C3 C 1.4572(4) 0.0717(3) 1.0700(3) 0.0225(8) Uani 1 1 d . . . . .
C11 C 1.0856(4) 0.4066(3) 0.5584(3) 0.0241(9) Uani 1 1 d . . . . .
H11 H 1.1435 0.3448 0.5985 0.029 Uiso 1 1 calc R U . . .
C22 C 0.3973(4) 0.5129(4) 0.9298(4) 0.0389(11) Uani 1 1 d . . . . .
H22 H 0.3288 0.5215 0.8818 0.047 Uiso 1 1 calc R U . . .
C1 C 1.2142(4) 0.0214(3) 1.0678(3) 0.0214(8) Uani 1 1 d . . . . .
C14 C 0.6177(4) -0.0320(3) 0.4386(3) 0.0216(8) Uani 1 1 d . . . . .
C8 C 0.9346(4) 0.6129(4) 0.9561(3) 0.0272(9) Uani 1 1 d . . . . .
H8 H 0.8912 0.6885 0.9254 0.033 Uiso 1 1 calc R U . . .
C19 C 0.6246(4) 0.3055(4) 0.8000(4) 0.0379(11) Uani 1 1 d . . . . .
H19 H 0.7125 0.3211 0.8036 0.045 Uiso 1 1 calc R U . . .
C6 C 1.0028(3) 0.4095(3) 0.9435(3) 0.0197(8) Uani 1 1 d . . . . .
C10 C 0.9634(4) 0.3812(3) 0.5296(3) 0.0211(8) Uani 1 1 d . . . . .
C9 C 0.9357(4) 0.2505(3) 0.5601(4) 0.0246(9) Uani 1 1 d . . . . .
C5 C 1.0082(4) 0.3060(3) 0.8884(3) 0.0229(9) Uani 1 1 d . . . . .
C7 C 0.9372(4) 0.5219(4) 0.9022(3) 0.0247(9) Uani 1 1 d . . . . .
C17 C 0.4053(4) 0.3077(4) 0.8263(4) 0.0331(10) Uani 1 1 d . . . . .
H17 H 0.3165 0.3246 0.8502 0.040 Uiso 1 1 calc R U . . .
C12 C 0.8790(4) 0.4766(3) 0.4724(3) 0.0227(9) Uani 1 1 d . . . . .
H9B H 1.118(5) -0.160(5) 0.917(5) 0.051(18) Uiso 1 1 d . . . . .
H1 H 0.394(4) 0.198(5) 0.737(5) 0.08(2) Uiso 1 1 d 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
Br1 C3 1.911(3) . ?
Br2 C7 1.905(4) . ?
Br4 C15 1.900(4) . ?
Br3 C12 1.907(4) . ?
Ca1 O7 2.898(3) 2_756 ?
Ca1 O8 2.551(3) 2_756 ?
Ca1 O1 2.944(3) 2_757 ?
Ca1 O1 2.350(3) . ?
Ca1 O4 2.572(2) . ?
Ca1 O5 2.325(3) . ?
Ca1 O2 2.490(3) 2_757 ?
Ca1 O9 2.407(3) . ?
Ca1 O3 2.555(3) . ?
Ca1 C13 3.090(3) 2_756 ?
Ca1 C1 3.038(4) 2_757 ?
Ca1 C5 2.880(4) . ?
Ca2 Ca1 4.3986(7) 2_756 ?
Ca2 O7 2.307(3) . ?
Ca2 O7 2.307(3) 2_756 ?
Ca2 O6 2.367(3) . ?
Ca2 O6 2.367(3) 2_756 ?
Ca2 O10 2.332(3) . ?
Ca2 O10 2.332(3) 2_756 ?
Ca2 C9 3.169(4) 2_756 ?
Ca2 C9 3.169(4) . ?
O7 Ca1 2.898(3) 2_756 ?
O7 C13 1.247(4) . ?
O8 Ca1 2.551(3) 2_756 ?
O8 C13 1.255(4) . ?
O1 Ca1 2.944(3) 2_757 ?
O1 C1 1.227(5) . ?
O4 C5 1.257(4) . ?
O5 C9 1.233(5) . ?
O2 Ca1 2.490(3) 2_757 ?
O2 C1 1.245(5) . ?
O6 C9 1.253(5) . ?
O3 C5 1.242(4) . ?
N2 C20 1.445(5) . ?
N2 C19 1.386(5) . ?
N2 C17 1.332(5) . ?
N1 C18 1.368(5) . ?
N1 C17 1.311(5) . ?
C15 C16 1.393(5) 2_656 ?
C15 C14 1.381(5) . ?
C20 C21 1.381(6) . ?
C20 C22 1.385(6) . ?
C4 C2 1.391(5) 2_857 ?
C4 C3 1.370(5) . ?
C2 C4 1.391(5) 2_857 ?
C2 C3 1.394(5) . ?
C2 C1 1.511(5) . ?
C16 C15 1.393(5) 2_656 ?
C16 C14 1.397(5) . ?
C13 Ca1 3.090(3) 2_756 ?
C13 C14 1.509(5) . ?
C21 C22 1.374(6) 2_667 ?
C18 C19 1.345(6) . ?
C11 C10 1.395(5) . ?
C11 C12 1.383(5) 2_766 ?
C22 C21 1.374(6) 2_667 ?
C1 Ca1 3.038(4) 2_757 ?
C8 C6 1.395(5) 2_767 ?
C8 C7 1.389(5) . ?
C6 C8 1.395(5) 2_767 ?
C6 C5 1.525(5) . ?
C6 C7 1.378(5) . ?
C10 C9 1.513(5) . ?
C10 C12 1.385(5) . ?
C12 C11 1.383(5) 2_766 ?

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
O7 Ca1 O1 128.57(8) 2_756 2_757 ?
O7 Ca1 C13 23.76(8) 2_756 2_756 ?
O7 Ca1 C1 116.66(9) 2_756 2_757 ?
O8 Ca1 O7 46.94(7) 2_756 2_756 ?
O8 Ca1 O1 154.23(10) 2_756 2_757 ?
O8 Ca1 O4 124.19(9) 2_756 . ?
O8 Ca1 O3 73.22(8) 2_756 . ?
O8 Ca1 C13 23.29(9) 2_756 2_756 ?
O8 Ca1 C1 161.90(9) 2_756 2_757 ?
O8 Ca1 C5 98.74(10) 2_756 . ?
O1 Ca1 O7 126.84(9) . 2_756 ?
O1 Ca1 O8 95.72(10) . 2_756 ?
O1 Ca1 O1 66.84(11) . 2_757 ?
O1 Ca1 O4 77.88(9) . . ?
O1 Ca1 O2 112.93(11) . 2_757 ?
O1 Ca1 O9 73.46(11) . . ?
O1 Ca1 O3 76.20(12) . . ?
O1 Ca1 C13 145.01(9) 2_757 2_756 ?
O1 Ca1 C13 111.04(10) . 2_756 ?
O1 Ca1 C1 90.30(11) . 2_757 ?
O1 Ca1 C1 23.59(9) 2_757 2_757 ?
O1 Ca1 C5 73.52(11) . . ?
O4 Ca1 O7 150.61(9) . 2_756 ?
O4 Ca1 O1 72.45(8) . 2_757 ?
O4 Ca1 C13 142.51(9) . 2_756 ?
O4 Ca1 C1 73.76(9) . 2_757 ?
O4 Ca1 C5 25.87(9) . . ?
O5 Ca1 O7 69.10(9) . 2_756 ?
O5 Ca1 O8 87.61(10) . 2_756 ?
O5 Ca1 O1 115.51(10) . 2_757 ?
O5 Ca1 O1 159.51(11) . . ?
O5 Ca1 O4 83.52(10) . . ?
O5 Ca1 O2 73.60(10) . 2_757 ?
O5 Ca1 O9 127.02(11) . . ?
O5 Ca1 O3 85.51(11) . . ?
O5 Ca1 C13 79.06(11) . 2_756 ?
O5 Ca1 C1 92.70(11) . 2_757 ?
O5 Ca1 C5 86.00(11) . . ?
O2 Ca1 O7 96.51(8) 2_757 2_756 ?
O2 Ca1 O8 143.35(9) 2_757 2_756 ?
O2 Ca1 O1 46.23(9) 2_757 2_757 ?
O2 Ca1 O4 85.37(9) 2_757 . ?
O2 Ca1 O3 133.98(10) 2_757 . ?
O2 Ca1 C13 120.26(10) 2_757 2_756 ?
O2 Ca1 C1 23.44(10) 2_757 2_757 ?
O2 Ca1 C5 110.67(11) 2_757 . ?
O9 Ca1 O7 66.41(10) . 2_756 ?
O9 Ca1 O8 82.52(11) . 2_756 ?
O9 Ca1 O1 74.53(10) . 2_757 ?
O9 Ca1 O4 142.66(11) . . ?
O9 Ca1 O2 84.27(11) . 2_757 ?
O9 Ca1 O3 138.65(11) . . ?
O9 Ca1 C13 71.73(11) . 2_756 ?
O9 Ca1 C1 82.88(11) . 2_757 ?
O9 Ca1 C5 146.91(11) . . ?
O3 Ca1 O7 113.85(8) . 2_756 ?
O3 Ca1 O1 117.57(9) . 2_757 ?
O3 Ca1 O4 51.24(8) . . ?
O3 Ca1 C13 94.22(9) . 2_756 ?
O3 Ca1 C1 124.86(9) . 2_757 ?
O3 Ca1 C5 25.53(9) . . ?
C1 Ca1 C13 139.53(10) 2_757 2_756 ?
C5 Ca1 O7 136.21(10) . 2_756 ?
C5 Ca1 O1 94.32(10) . 2_757 ?
C5 Ca1 C13 119.21(10) . 2_756 ?
C5 Ca1 C1 99.33(10) . 2_757 ?
Ca1 Ca2 Ca1 180.0 2_756 . ?
O7 Ca2 Ca1 36.70(6) 2_756 . ?
O7 Ca2 Ca1 143.30(6) . . ?
O7 Ca2 Ca1 143.30(6) 2_756 2_756 ?
O7 Ca2 Ca1 36.70(6) . 2_756 ?
O7 Ca2 O7 180.0 2_756 . ?
O7 Ca2 O6 89.66(10) . . ?
O7 Ca2 O6 90.34(10) 2_756 . ?
O7 Ca2 O6 90.34(10) . 2_756 ?
O7 Ca2 O6 89.66(10) 2_756 2_756 ?
O7 Ca2 O10 89.62(12) 2_756 2_756 ?
O7 Ca2 O10 89.62(12) . . ?
O7 Ca2 O10 90.38(12) . 2_756 ?
O7 Ca2 O10 90.38(12) 2_756 . ?
O7 Ca2 C9 107.80(10) 2_756 2_756 ?
O7 Ca2 C9 72.20(10) . 2_756 ?
O7 Ca2 C9 107.80(10) . . ?
O7 Ca2 C9 72.20(10) 2_756 . ?
O6 Ca2 Ca1 71.41(8) . . ?
O6 Ca2 Ca1 108.59(8) 2_756 . ?
O6 Ca2 Ca1 71.41(8) 2_756 2_756 ?
O6 Ca2 Ca1 108.59(8) . 2_756 ?
O6 Ca2 O6 180.00(16) 2_756 . ?
O6 Ca2 C9 159.74(11) . 2_756 ?
O6 Ca2 C9 20.26(11) 2_756 2_756 ?
O6 Ca2 C9 20.26(11) . . ?
O6 Ca2 C9 159.74(11) 2_756 . ?
O10 Ca2 Ca1 64.18(9) 2_756 2_756 ?
O10 Ca2 Ca1 115.82(9) . 2_756 ?
O10 Ca2 Ca1 115.82(9) 2_756 . ?
O10 Ca2 Ca1 64.18(9) . . ?
O10 Ca2 O6 80.31(13) . 2_756 ?
O10 Ca2 O6 80.31(13) 2_756 . ?
O10 Ca2 O6 99.69(13) . . ?
O10 Ca2 O6 99.69(13) 2_756 2_756 ?
O10 Ca2 O10 180.0 2_756 . ?
O10 Ca2 C9 89.40(12) . 2_756 ?
O10 Ca2 C9 90.60(12) 2_756 2_756 ?
O10 Ca2 C9 89.40(12) 2_756 . ?
O10 Ca2 C9 90.60(12) . . ?
C9 Ca2 Ca1 51.28(8) . . ?
C9 Ca2 Ca1 128.72(8) 2_756 . ?
C9 Ca2 Ca1 128.72(8) . 2_756 ?
C9 Ca2 Ca1 51.28(8) 2_756 2_756 ?
C9 Ca2 C9 180.0 . 2_756 ?
Ca2 O7 Ca1 114.89(10) . 2_756 ?
C13 O7 Ca1 86.8(2) . 2_756 ?
C13 O7 Ca2 144.9(3) . . ?
C13 O8 Ca1 103.2(2) . 2_756 ?
Ca1 O1 Ca1 113.16(11) . 2_757 ?
C1 O1 Ca1 82.5(2) . 2_757 ?
C1 O1 Ca1 163.1(3) . . ?
C5 O4 Ca1 90.9(2) . . ?
C9 O5 Ca1 151.3(3) . . ?
C1 O2 Ca1 103.8(2) . 2_757 ?
C9 O6 Ca2 118.9(3) . . ?
C5 O3 Ca1 92.0(2) . . ?
C19 N2 C20 126.8(3) . . ?
C17 N2 C20 125.3(3) . . ?
C17 N2 C19 107.9(3) . . ?
C17 N1 C18 109.7(4) . . ?
C16 C15 Br4 116.4(3) 2_656 . ?
C14 C15 Br4 121.3(3) . . ?
C14 C15 C16 122.2(3) . 2_656 ?
C21 C20 N2 119.6(4) . . ?
C21 C20 C22 120.7(4) . . ?
C22 C20 N2 119.7(4) . . ?
C3 C4 C2 121.0(3) . 2_857 ?
C4 C2 C3 117.1(3) 2_857 . ?
C4 C2 C1 117.5(3) 2_857 . ?
C3 C2 C1 125.4(3) . . ?
C15 C16 C14 120.0(4) 2_656 . ?
O7 C13 Ca1 69.45(19) . 2_756 ?
O7 C13 O8 122.5(3) . . ?
O7 C13 C14 118.1(3) . . ?
O8 C13 Ca1 53.48(17) . 2_756 ?
O8 C13 C14 119.4(3) . . ?
C14 C13 Ca1 168.0(3) . 2_756 ?
C22 C21 C20 119.4(4) 2_667 . ?
C19 C18 N1 106.8(4) . . ?
C4 C3 Br1 117.3(3) . . ?
C4 C3 C2 121.9(3) . . ?
C2 C3 Br1 120.7(3) . . ?
C12 C11 C10 120.3(4) 2_766 . ?
C21 C22 C20 119.9(4) 2_667 . ?
O1 C1 Ca1 73.9(2) . 2_757 ?
O1 C1 O2 123.2(4) . . ?
O1 C1 C2 117.8(3) . . ?
O2 C1 Ca1 52.73(19) . 2_757 ?
O2 C1 C2 118.8(3) . . ?
C2 C1 Ca1 153.9(3) . 2_757 ?
C15 C14 C16 117.7(3) . . ?
C15 C14 C13 125.8(3) . . ?
C16 C14 C13 116.5(3) . . ?
C7 C8 C6 119.8(4) . 2_767 ?
C18 C19 N2 107.1(4) . . ?
C8 C6 C5 117.4(3) 2_767 . ?
C7 C6 C8 118.2(3) . 2_767 ?
C7 C6 C5 124.3(3) . . ?
C11 C10 C9 117.1(3) . . ?
C12 C10 C11 117.7(3) . . ?
C12 C10 C9 125.1(3) . . ?
O5 C9 Ca2 88.7(2) . . ?
O5 C9 O6 125.0(4) . . ?
O5 C9 C10 117.4(3) . . ?
O6 C9 Ca2 40.85(19) . . ?
O6 C9 C10 117.6(4) . . ?
C10 C9 Ca2 145.9(2) . . ?
O4 C5 Ca1 63.28(18) . . ?
O4 C5 C6 117.2(3) . . ?
O3 C5 Ca1 62.44(18) . . ?
O3 C5 O4 125.1(3) . . ?
O3 C5 C6 117.7(3) . . ?
C6 C5 Ca1 169.9(3) . . ?
C8 C7 Br2 118.0(3) . . ?
C6 C7 Br2 120.0(3) . . ?
C6 C7 C8 122.0(4) . . ?
N1 C17 N2 108.6(4) . . ?
C11 C12 Br3 118.3(3) 2_766 . ?
C11 C12 C10 122.0(4) 2_766 . ?
C10 C12 Br3 119.6(3) . . ?

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1496612'
_audit_update_record             
;
2016-07-29 deposited with the CCDC.
2016-10-03 downloaded from the CCDC.
;
_audit_creation_date             2016-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C8 H6 Br2 Ca O6, C5 H4 N'
_chemical_formula_sum            'C13 H10 Br2 Ca N O6'
_chemical_formula_weight         476.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 N1 O1 Zn1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2260 0.3060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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                   7.7834(4)
_cell_length_b                   10.1301(5)
_cell_length_c                   10.3277(8)
_cell_angle_alpha                103.873(5)
_cell_angle_beta                 91.797(5)
_cell_angle_gamma                90.935(4)
_cell_volume                     789.92(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2435
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5040
_cell_measurement_theta_min      3.2330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.484
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.002
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             466
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4940
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.530
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.5095
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0157948000
_diffrn_orient_matrix_UB_12      0.0018613000
_diffrn_orient_matrix_UB_13      0.0676742000
_diffrn_orient_matrix_UB_21      0.0144490000
_diffrn_orient_matrix_UB_22      0.0714927000
_diffrn_orient_matrix_UB_23      0.0169985000
_diffrn_orient_matrix_UB_31      -0.0886541000
_diffrn_orient_matrix_UB_32      0.0094975000
_diffrn_orient_matrix_UB_33      -0.0119329000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2313
_reflns_number_total             2774
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
'L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation (2013)'
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.903
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2774
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.043
_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)+(0.0270P)²+0.3990P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0679
_refine_ls_wR_factor_ref         0.0736
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O5-H5B
 0.85 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C9(H9), C10(H10), C13(H13), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.00374(7) 0.21483(4) 0.09376(5) 0.04781(17) Uani 1 1 d . . . . .
O1 O 0.0107(3) 0.4873(3) 0.3542(2) 0.0232(6) Uani 1 1 d . . . . .
O2 O 0.2692(3) 0.5465(3) 0.3064(3) 0.0287(7) Uani 1 1 d . . . . .
C3 C -0.0029(5) 0.3828(4) 0.0436(4) 0.0221(9) Uani 1 1 d . . . . .
C2 C 0.0578(4) 0.5006(3) 0.1299(3) 0.0171(8) Uani 1 1 d . . . . .
C1 C 0.1165(4) 0.5108(3) 0.2729(3) 0.0166(8) Uani 1 1 d . . . . .
C4 C -0.0604(5) 0.3808(4) -0.0853(4) 0.0245(9) Uani 1 1 d . . . . .
H4 H -0.1008 0.2998 -0.1420 0.029 Uiso 1 1 calc R U . . .
Br2 Br 0.17285(5) -0.01353(4) 0.29075(5) 0.04229(16) Uani 1 1 d . . . . .
C6 C 0.4371(4) 0.1228(3) 0.4776(4) 0.0171(8) Uani 1 1 d . . . . .
O4 O 0.4844(3) 0.3470(2) 0.4514(3) 0.0228(6) Uani 1 1 d . . . . .
C8 C 0.4218(4) -0.1221(3) 0.4356(4) 0.0205(8) Uani 1 1 d . . . . .
H8 H 0.3681 -0.2039 0.3913 0.025 Uiso 1 1 calc R U . . .
O3 O 0.2189(3) 0.2843(2) 0.4819(3) 0.0315(7) Uani 1 1 d . . . . .
C5 C 0.3744(4) 0.2604(3) 0.4672(4) 0.0201(8) Uani 1 1 d . . . . .
C7 C 0.3610(4) -0.0012(3) 0.4149(4) 0.0203(8) Uani 1 1 d . . . . .
C11 C 0.4691(5) 0.0561(4) -0.0297(5) 0.0362(11) Uani 1 1 d . . . . .
C9 C 0.3087(6) 0.1397(5) -0.1931(5) 0.0469(13) Uani 1 1 d . . . . .
H9 H 0.2350 0.1203 -0.2683 0.056 Uiso 1 1 calc R U . . .
N1 N 0.3560(5) 0.2680(4) -0.1428(4) 0.0484(11) Uani 1 1 d . . . . .
C10 C 0.3611(6) 0.0322(5) -0.1419(5) 0.0418(12) Uani 1 1 d . . . . .
H10 H 0.3237 -0.0560 -0.1828 0.050 Uiso 1 1 calc R U . . .
C13 C 0.4571(7) 0.2897(5) -0.0339(6) 0.0680(17) Uani 1 1 d . . . . .
H13 H 0.4915 0.3790 0.0056 0.082 Uiso 1 1 calc R U . . .
C12 C 0.5151(7) 0.1896(5) 0.0253(6) 0.0643(17) Uani 1 1 d . . . . .
H12 H 0.5854 0.2125 0.1023 0.077 Uiso 1 1 calc R U . . .
O5 O 0.1298(4) 0.7564(3) 0.5784(4) 0.0368(8) Uani 1 1 d D . . . .
O6 O 0.3784(4) 0.4979(3) 0.7420(3) 0.0319(7) Uani 1 1 d . . . . .
Ca1 Ca 0.25016(8) 0.53263(7) 0.54032(7) 0.01519(18) Uani 1 1 d . . . . .
H5A H 0.035(7) 0.764(5) 0.574(6) 0.066(19) Uiso 1 1 d . . . . .
H6A H 0.350(6) 0.435(5) 0.772(5) 0.042(15) Uiso 1 1 d . . . . .
H6B H 0.486(6) 0.489(5) 0.734(5) 0.051(15) Uiso 1 1 d . . . . .
H5B H 0.164(7) 0.821(4) 0.550(5) 0.078(19) Uiso 1 1 d 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
Br1 C3 1.894(3) . ?
O1 C1 1.254(4) . ?
O2 C1 1.250(4) . ?
C3 C2 1.373(5) . ?
C3 C4 1.387(5) . ?
C2 C1 1.511(5) . ?
C2 C4 1.386(5) 2_565 ?
C4 C2 1.386(5) 2_565 ?
C4 H4 0.9300 . ?
Br2 C7 1.899(3) . ?
C6 C8 1.397(4) 2_656 ?
C6 C5 1.511(4) . ?
C6 C7 1.382(5) . ?
O4 C5 1.258(4) . ?
C8 C6 1.397(4) 2_656 ?
C8 H8 0.9300 . ?
C8 C7 1.381(5) . ?
O3 C5 1.245(4) . ?
C11 C11 1.494(8) 2_655 ?
C11 C10 1.380(6) . ?
C11 C12 1.372(6) . ?
C9 H9 0.9300 . ?
C9 N1 1.320(6) . ?
C9 C10 1.382(6) . ?
N1 C13 1.325(6) . ?
C10 H10 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.378(7) . ?
C12 H12 0.9300 . ?
O5 H5A 0.75(5) . ?
O5 H5B 0.83(2) . ?
O6 H6A 0.80(5) . ?
O6 H6B 0.84(5) . ?

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
C2 C3 Br1 120.6(2) . . ?
C2 C3 C4 121.5(3) . . ?
C4 C3 Br1 117.7(3) . . ?
C3 C2 C1 124.2(3) . . ?
C3 C2 C4 118.4(3) . 2_565 ?
C4 C2 C1 117.4(3) 2_565 . ?
O1 C1 C2 119.4(3) . . ?
O2 C1 O1 122.4(3) . . ?
O2 C1 C2 118.1(3) . . ?
C3 C4 H4 119.9 . . ?
C2 C4 C3 120.1(3) 2_565 . ?
C2 C4 H4 119.9 2_565 . ?
C8 C6 C5 116.7(3) 2_656 . ?
C7 C6 C8 117.5(3) . 2_656 ?
C7 C6 C5 125.6(3) . . ?
C6 C8 H8 119.7 2_656 . ?
C7 C8 C6 120.7(3) . 2_656 ?
C7 C8 H8 119.7 . . ?
O4 C5 C6 117.8(3) . . ?
O3 C5 C6 118.4(3) . . ?
O3 C5 O4 123.6(3) . . ?
C6 C7 Br2 121.3(2) . . ?
C8 C7 Br2 116.8(3) . . ?
C8 C7 C6 121.8(3) . . ?
C10 C11 C11 122.2(5) . 2_655 ?
C12 C11 C11 121.8(5) . 2_655 ?
C12 C11 C10 116.0(4) . . ?
N1 C9 H9 117.7 . . ?
N1 C9 C10 124.5(4) . . ?
C10 C9 H9 117.7 . . ?
C9 N1 C13 115.0(4) . . ?
C11 C10 C9 119.8(4) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C13 H13 117.6 . . ?
N1 C13 C12 124.8(5) . . ?
C12 C13 H13 117.6 . . ?
C11 C12 C13 119.9(5) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
H5A O5 H5B 102(5) . . ?
H6A O6 H6B 104(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
