# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_L1
_database_code_depnum_ccdc_archive 'CCDC 1440881'
_audit_update_record             
;
2016-04-02 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;
_audit_creation_date             2015-09-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.21 svn.r3230 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            L1
_chemical_name_systematic        L1
_chemical_formula_moiety         'C36 H40 N6 O4, 6(C H Cl3)'
_chemical_formula_sum            'C42 H46 Cl18 N6 O4'
_chemical_formula_weight         1336.95
_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'
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'

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

_cell_length_a                   9.824(2)
_cell_length_b                   10.344(2)
_cell_length_c                   15.141(3)
_cell_angle_alpha                88.40(3)
_cell_angle_beta                 73.13(3)
_cell_angle_gamma                88.03(3)
_cell_volume                     1471.2(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5736
_cell_measurement_temperature    153.1500
_cell_measurement_theta_max      31.4919
_cell_measurement_theta_min      1.9704
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9062
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Higashi, T. (1995).'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             678
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_exptl_special_details           
;
 Higashi, T. (1995). Program for Absorption Correction.
  Rigaku Corporation, Tokyo, Japan.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22025
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.526
_diffrn_reflns_theta_min         2.216
_diffrn_ambient_temperature      153.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -115.0000 - 65.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.0592
	          2theta: -25.2012
scan:
	Number of images: 360
	           Slice: -115.0000 - 65.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.0592
	          2theta: -25.2012
scan:
	Number of images: 360
	           Slice: -115.0000 - 65.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 45.0592
	          2theta: -25.2012
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             9627
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0012
_diffrn_orient_matrix_UB_12      0.1016
_diffrn_orient_matrix_UB_13      -0.0315
_diffrn_orient_matrix_UB_21      -0.0964
_diffrn_orient_matrix_UB_22      -0.0058
_diffrn_orient_matrix_UB_23      -0.0062
_diffrn_orient_matrix_UB_31      -0.0031
_diffrn_orient_matrix_UB_32      0.0004
_diffrn_orient_matrix_UB_33      0.0690
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           90.0000
_diffrn_source_power             4.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7954
_reflns_number_total             9618
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.018
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         9618
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.073
_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)+(0.0610P)²+0.8820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1405
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19), C20(H20), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O -0.75853(13) 0.19544(15) 0.21468(9) 0.0297(3) Uani 1 1 d . . . . .
O2 O -0.67642(13) 0.22325(14) -0.09256(9) 0.0255(3) Uani 1 1 d . . . . .
N1 N -0.58745(15) 0.21889(16) 0.28561(10) 0.0233(3) Uani 1 1 d . . . . .
N2 N -0.56705(14) 0.19305(14) 0.04760(9) 0.0188(3) Uani 1 1 d . . . . .
N3 N -0.46211(16) 0.19718(16) -0.19988(10) 0.0243(3) Uani 1 1 d . . . . .
C1 C -0.7323(3) 0.3657(3) 0.40464(19) 0.0491(6) Uani 1 1 d . . . . .
H1A H -0.6555 0.3708 0.4337 0.074 Uiso 1 1 calc GR . . . .
H1B H -0.8244 0.3768 0.4516 0.074 Uiso 1 1 calc GR . . . .
H1C H -0.7220 0.4341 0.3573 0.074 Uiso 1 1 calc GR . . . .
C2 C -0.7341(3) 0.1254(3) 0.43019(19) 0.0561(8) Uani 1 1 d . . . . .
H2A H -0.7323 0.0424 0.4001 0.084 Uiso 1 1 calc GR . . . .
H2B H -0.8230 0.1350 0.4802 0.084 Uiso 1 1 calc GR . . . .
H2C H -0.6532 0.1279 0.4556 0.084 Uiso 1 1 calc GR . . . .
C3 C -0.72444(18) 0.23450(19) 0.36038(12) 0.0246(3) Uani 1 1 d . . . . .
C4 C -0.8374(2) 0.2275(3) 0.30816(14) 0.0399(5) Uani 1 1 d . . . . .
H4A H -0.9070 0.1601 0.3360 0.048 Uiso 1 1 calc R . . . .
H4B H -0.8890 0.3117 0.3097 0.048 Uiso 1 1 calc R . . . .
C5 C -0.61934(17) 0.19685(16) 0.21199(11) 0.0194(3) Uani 1 1 d . . . . .
C6 C -0.51672(17) 0.17152(16) 0.12004(11) 0.0184(3) Uani 1 1 d . . . . .
C7 C -0.37897(17) 0.12559(16) 0.11250(11) 0.0186(3) Uani 1 1 d . . . . .
H7 H -0.3477 0.1136 0.1660 0.022 Uiso 1 1 calc R . . . .
C8 C -0.28719(17) 0.09737(16) 0.02516(11) 0.0179(3) Uani 1 1 d . . . . .
C9 C -0.33953(17) 0.11908(16) -0.05058(11) 0.0193(3) Uani 1 1 d . . . . .
H9 H -0.2815 0.1007 -0.1112 0.023 Uiso 1 1 calc R . . . .
C10 C -0.47776(17) 0.16800(16) -0.03612(11) 0.0188(3) Uani 1 1 d . . . . .
C11 C -0.53481(17) 0.19573(16) -0.11523(11) 0.0198(3) Uani 1 1 d . . . . .
C12 C -0.7096(2) 0.2326(2) -0.17996(13) 0.0303(4) Uani 1 1 d . . . . .
H12A H -0.7669 0.3122 -0.1834 0.036 Uiso 1 1 calc R . . . .
H12B H -0.7628 0.1567 -0.1884 0.036 Uiso 1 1 calc R . . . .
C13 C -0.5633(2) 0.23674(18) -0.25328(12) 0.0246(3) Uani 1 1 d . . . . .
C14 C -0.5279(2) 0.3728(2) -0.29173(14) 0.0333(4) Uani 1 1 d . . . . .
H14A H -0.5412 0.4326 -0.2406 0.050 Uiso 1 1 calc GR . . . .
H14B H -0.5909 0.3995 -0.3290 0.050 Uiso 1 1 calc GR . . . .
H14C H -0.4288 0.3740 -0.3303 0.050 Uiso 1 1 calc GR . . . .
C15 C -0.5504(3) 0.1423(2) -0.33098(14) 0.0350(4) Uani 1 1 d . . . . .
H15A H -0.4560 0.1484 -0.3758 0.053 Uiso 1 1 calc GR . . . .
H15B H -0.6236 0.1637 -0.3617 0.053 Uiso 1 1 calc GR . . . .
H15C H -0.5632 0.0539 -0.3054 0.053 Uiso 1 1 calc GR . . . .
C16 C -0.14000(17) 0.04695(16) 0.01249(11) 0.0189(3) Uani 1 1 d . . . . .
C17 C -0.05662(17) 0.09494(17) 0.06422(11) 0.0211(3) Uani 1 1 d . . . . .
H17 H -0.0953 0.1599 0.1083 0.025 Uiso 1 1 calc R . . . .
C18 C -0.08207(17) -0.04899(17) -0.05207(11) 0.0213(3) Uani 1 1 d . . . . .
H18 H -0.1375 -0.0827 -0.0876 0.026 Uiso 1 1 calc R . . . .
Cl1 Cl 0.05862(6) 0.45261(10) 0.09823(5) 0.0627(2) Uani 1 1 d . . . . .
Cl2 Cl 0.29011(7) 0.54916(6) -0.04938(4) 0.04292(14) Uani 1 1 d . . . . .
Cl3 Cl 0.31891(7) 0.52307(6) 0.13508(4) 0.04377(14) Uani 1 1 d . . . . .
C19 C 0.2436(2) 0.45760(19) 0.05436(13) 0.0274(4) Uani 1 1 d . . . . .
H19 H 0.2822 0.3673 0.0410 0.033 Uiso 1 1 calc R . . . .
Cl4 Cl 0.80727(7) 0.34144(7) 0.26639(4) 0.04817(15) Uani 1 1 d . . . . .
Cl5 Cl 0.74444(9) 0.12314(6) 0.39209(6) 0.05667(19) Uani 1 1 d . . . . .
Cl6 Cl 0.63718(7) 0.37812(6) 0.45409(4) 0.04636(15) Uani 1 1 d . . . . .
C20 C 0.6796(2) 0.2725(2) 0.36033(13) 0.0290(4) Uani 1 1 d . . . . .
H20 H 0.5916 0.2578 0.3419 0.035 Uiso 1 1 calc R . . . .
Cl7 Cl 0.86951(7) 0.23433(9) 0.58019(5) 0.0585(2) Uani 1 1 d . . . . .
Cl8 Cl 1.02703(10) 0.38021(8) 0.67324(6) 0.0651(2) Uani 1 1 d . . . . .
Cl9 Cl 0.97952(8) 0.11159(8) 0.72024(6) 0.0623(2) Uani 1 1 d . . . . .
C21 C 0.9082(2) 0.2542(2) 0.68442(15) 0.0380(5) Uani 1 1 d . . . . .
H21 H 0.8178 0.2778 0.7327 0.046 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
O1 C4 1.444(2) . ?
O1 C5 1.357(2) . ?
O2 C11 1.355(2) . ?
O2 C12 1.452(2) . ?
N1 C3 1.493(2) . ?
N1 C5 1.271(2) . ?
N2 C6 1.338(2) . ?
N2 C10 1.342(2) . ?
N3 C11 1.273(2) . ?
N3 C13 1.493(2) . ?
C1 C3 1.520(3) . ?
C2 C3 1.511(3) . ?
C3 C4 1.543(3) . ?
C5 C6 1.487(2) . ?
C6 C7 1.393(2) . ?
C7 C8 1.399(2) . ?
C8 C9 1.396(2) . ?
C8 C16 1.481(2) . ?
C9 C10 1.391(2) . ?
C10 C11 1.480(2) . ?
C12 C13 1.541(3) . ?
C13 C14 1.520(3) . ?
C13 C15 1.525(3) . ?
C16 C17 1.397(2) . ?
C16 C18 1.399(2) . ?
C17 C18 1.390(2) 2 ?
C18 C17 1.390(2) 2 ?
Cl1 C19 1.747(2) . ?
Cl2 C19 1.762(2) . ?
Cl3 C19 1.762(2) . ?
Cl4 C20 1.753(2) . ?
Cl5 C20 1.758(2) . ?
Cl6 C20 1.759(2) . ?
Cl7 C21 1.746(2) . ?
Cl8 C21 1.752(3) . ?
Cl9 C21 1.751(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
C5 O1 C4 105.57(14) . . ?
C11 O2 C12 105.06(13) . . ?
C5 N1 C3 106.79(14) . . ?
C6 N2 C10 116.91(14) . . ?
C11 N3 C13 106.16(14) . . ?
N1 C3 C1 110.02(16) . . ?
N1 C3 C2 108.57(17) . . ?
N1 C3 C4 103.11(14) . . ?
C1 C3 C4 110.57(19) . . ?
C2 C3 C1 111.5(2) . . ?
C2 C3 C4 112.8(2) . . ?
O1 C4 C3 105.15(15) . . ?
O1 C5 C6 115.08(14) . . ?
N1 C5 O1 119.01(15) . . ?
N1 C5 C6 125.91(15) . . ?
N2 C6 C5 115.63(14) . . ?
N2 C6 C7 123.62(14) . . ?
C7 C6 C5 120.73(14) . . ?
C6 C7 C8 119.20(14) . . ?
C7 C8 C16 121.89(14) . . ?
C9 C8 C7 117.35(14) . . ?
C9 C8 C16 120.75(14) . . ?
C10 C9 C8 119.15(14) . . ?
N2 C10 C9 123.73(14) . . ?
N2 C10 C11 115.85(14) . . ?
C9 C10 C11 120.42(14) . . ?
O2 C11 C10 115.15(14) . . ?
N3 C11 O2 119.31(15) . . ?
N3 C11 C10 125.54(15) . . ?
O2 C12 C13 104.45(14) . . ?
N3 C13 C12 103.20(14) . . ?
N3 C13 C14 108.10(16) . . ?
N3 C13 C15 109.99(16) . . ?
C14 C13 C12 111.98(17) . . ?
C14 C13 C15 110.78(16) . . ?
C15 C13 C12 112.43(17) . . ?
C17 C16 C8 120.63(14) . . ?
C17 C16 C18 119.03(15) . . ?
C18 C16 C8 120.34(14) . . ?
C18 C17 C16 120.96(15) 2 . ?
C17 C18 C16 120.01(15) 2 . ?
Cl1 C19 Cl2 109.88(11) . . ?
Cl1 C19 Cl3 110.99(11) . . ?
Cl2 C19 Cl3 110.33(11) . . ?
Cl4 C20 Cl5 110.01(11) . . ?
Cl4 C20 Cl6 109.93(12) . . ?
Cl5 C20 Cl6 110.17(11) . . ?
Cl7 C21 Cl8 109.90(14) . . ?
Cl7 C21 Cl9 111.59(14) . . ?
Cl9 C21 Cl8 109.97(13) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_compound_source        chloroform
####################################################################### 
# 
# 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_L3
_database_code_depnum_ccdc_archive 'CCDC 1471906'
_audit_update_record             
;
2016-04-02 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;
_audit_creation_date             2016-04-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            L3
_chemical_name_systematic        L3
_chemical_formula_moiety         'C48 H48 N6 O4, 2(C H4 O)'
_chemical_formula_sum            'C50 H56 N6 O6'
_chemical_formula_weight         837.02
_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'
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                   10.240(2)
_cell_length_b                   10.250(2)
_cell_length_c                   12.374(3)
_cell_angle_alpha                86.03(3)
_cell_angle_beta                 67.18(3)
_cell_angle_gamma                69.76(3)
_cell_volume                     1120.1(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3588
_cell_measurement_temperature    153.1500
_cell_measurement_theta_max      27.4855
_cell_measurement_theta_min      1.7906
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9212
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Higashi, T. (1995).'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             446
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
  Higashi, T. (1995). Program for Absorption Correction.
  Rigaku Corporation, Tokyo, Japan.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13739
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         2.532
_diffrn_ambient_temperature      153.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.0059
	          2theta: -20.1893
scan:
	Number of images: 342
	           Slice: -110.0000 - 61.0000
	     Image width: 0.5000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 45.0059
	          2theta: -20.1893
scan:
	Number of images: 304
	           Slice: -110.0000 - 42.0000
	     Image width: 0.5000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.0059
	          2theta: -20.1893
scan:
	Number of images: 204
	           Slice: -42.0000 - 60.0000
	     Image width: 0.5000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.0059
	          2theta: -20.1893
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             5121
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0221
_diffrn_orient_matrix_UB_12      0.1040
_diffrn_orient_matrix_UB_13      -0.0382
_diffrn_orient_matrix_UB_21      0.1003
_diffrn_orient_matrix_UB_22      -0.0237
_diffrn_orient_matrix_UB_23      -0.0157
_diffrn_orient_matrix_UB_31      -0.0172
_diffrn_orient_matrix_UB_32      -0.0626
_diffrn_orient_matrix_UB_33      -0.0593
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           90.0000
_diffrn_source_power             4.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4005
_reflns_number_total             4390
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.110
_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)+(0.0620P)²+0.4380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1392
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C),
 C25(H25A,H25B,H25C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O -0.10345(14) 0.73517(15) 0.82892(11) 0.0367(3) Uani 1 1 d . . . . .
O2 O 0.13353(13) 0.54011(13) 0.43914(10) 0.0301(3) Uani 1 1 d . . . . .
N1 N -0.02416(18) 0.88834(18) 0.88557(13) 0.0392(4) Uani 1 1 d . . . . .
N2 N 0.13122(15) 0.68735(14) 0.61185(12) 0.0238(3) Uani 1 1 d . . . . .
N3 N 0.33589(17) 0.57980(16) 0.30442(12) 0.0303(3) Uani 1 1 d . . . . .
C1 C -0.1306(2) 0.8351(2) 1.08946(17) 0.0427(5) Uani 1 1 d . . . . .
H1A H -0.0583 0.7423 1.0664 0.064 Uiso 1 1 calc GR . . . .
H1B H -0.2210 0.8322 1.1525 0.064 Uiso 1 1 calc GR . . . .
H1C H -0.0891 0.8917 1.1153 0.064 Uiso 1 1 calc GR . . . .
C2 C -0.2724(3) 1.0482(2) 1.01522(19) 0.0489(5) Uani 1 1 d . . . . .
H2A H -0.2252 1.1014 1.0382 0.073 Uiso 1 1 calc GR . . . .
H2B H -0.3655 1.0532 1.0789 0.073 Uiso 1 1 calc GR . . . .
H2C H -0.2926 1.0855 0.9477 0.073 Uiso 1 1 calc GR . . . .
C3 C -0.1679(2) 0.8973(2) 0.98501(15) 0.0351(4) Uani 1 1 d . . . . .
C4 C -0.2295(2) 0.8092(2) 0.93489(16) 0.0412(5) Uani 1 1 d . . . . .
H4A H -0.2620 0.7442 0.9906 0.049 Uiso 1 1 calc R . . . .
H4B H -0.3142 0.8684 0.9166 0.049 Uiso 1 1 calc R . . . .
C5 C 0.00015(19) 0.79733(18) 0.80973(14) 0.0270(4) Uani 1 1 d . . . . .
C6 C 0.13539(18) 0.75610(17) 0.69793(14) 0.0240(3) Uani 1 1 d . . . . .
C7 C 0.25615(18) 0.79603(17) 0.68779(14) 0.0250(4) Uani 1 1 d . . . . .
H7 H 0.2532 0.8419 0.7514 0.030 Uiso 1 1 calc R . . . .
C8 C 0.38139(17) 0.76700(17) 0.58198(14) 0.0229(3) Uani 1 1 d . . . . .
C9 C 0.37682(18) 0.69827(17) 0.49068(14) 0.0237(3) Uani 1 1 d . . . . .
H9 H 0.4569 0.6774 0.4177 0.028 Uiso 1 1 calc R . . . .
C10 C 0.25147(17) 0.66116(16) 0.50964(13) 0.0225(3) Uani 1 1 d . . . . .
C11 C 0.24515(17) 0.59182(16) 0.41092(14) 0.0229(3) Uani 1 1 d . . . . .
C12 C 0.1605(2) 0.4660(2) 0.33158(15) 0.0339(4) Uani 1 1 d . . . . .
H12A H 0.0701 0.4954 0.3146 0.041 Uiso 1 1 calc R . . . .
H12B H 0.1922 0.3660 0.3383 0.041 Uiso 1 1 calc R . . . .
C13 C 0.2875(2) 0.50619(18) 0.23534(14) 0.0290(4) Uani 1 1 d . . . . .
C14 C 0.2295(3) 0.6070(2) 0.15429(19) 0.0493(5) Uani 1 1 d . . . . .
H14A H 0.1440 0.6848 0.2006 0.074 Uiso 1 1 calc GR . . . .
H14B H 0.2000 0.5601 0.1081 0.074 Uiso 1 1 calc GR . . . .
H14C H 0.3080 0.6397 0.1031 0.074 Uiso 1 1 calc GR . . . .
C15 C 0.4208(2) 0.3802(2) 0.16564(17) 0.0402(5) Uani 1 1 d . . . . .
H15A H 0.5016 0.4099 0.1142 0.060 Uiso 1 1 calc GR . . . .
H15B H 0.3909 0.3331 0.1199 0.060 Uiso 1 1 calc GR . . . .
H15C H 0.4543 0.3179 0.2187 0.060 Uiso 1 1 calc GR . . . .
C16 C 0.51074(18) 0.81172(17) 0.56623(14) 0.0230(3) Uani 1 1 d . . . . .
C17 C 0.65551(19) 0.74331(18) 0.48323(15) 0.0277(4) Uani 1 1 d . . . . .
H17 H 0.6729 0.6662 0.4373 0.033 Uiso 1 1 calc R . . . .
C18 C 0.77356(18) 0.78855(18) 0.46819(16) 0.0287(4) Uani 1 1 d . . . . .
H18 H 0.8692 0.7412 0.4123 0.034 Uiso 1 1 calc R . . . .
C19 C 0.75194(18) 0.90413(17) 0.53542(14) 0.0246(3) Uani 1 1 d . . . . .
C20 C 0.60709(18) 0.97202(17) 0.61954(14) 0.0251(3) Uani 1 1 d . . . . .
H20 H 0.5899 1.0482 0.6663 0.030 Uiso 1 1 calc R . . . .
C21 C 0.48885(18) 0.92684(17) 0.63388(14) 0.0251(3) Uani 1 1 d . . . . .
H21 H 0.3931 0.9741 0.6896 0.030 Uiso 1 1 calc R . . . .
C22 C 0.87847(17) 0.95353(17) 0.51767(15) 0.0243(3) Uani 1 1 d . . . . .
C23 C 0.99434(18) 0.93900(18) 0.40659(15) 0.0273(4) Uani 1 1 d . . . . .
H23 H 0.9913 0.8984 0.3431 0.033 Uiso 1 1 calc R . . . .
C24 C 1.11334(18) 0.98395(18) 0.38947(15) 0.0270(4) Uani 1 1 d . . . . .
H24 H 1.1892 0.9723 0.3148 0.032 Uiso 1 1 calc R . . . .
O3 O 0.58849(18) 0.66445(18) 0.18042(16) 0.0584(5) Uani 1 1 d . . . . .
H3 H 0.5089 0.6489 0.2090 0.088 Uiso 1 1 calc GR . . . .
C25 C 0.7083(3) 0.5443(3) 0.1821(2) 0.0604(6) Uani 1 1 d . . . . .
H25A H 0.7356 0.4781 0.1189 0.091 Uiso 1 1 calc GR . . . .
H25B H 0.6769 0.5035 0.2557 0.091 Uiso 1 1 calc GR . . . .
H25C H 0.7938 0.5696 0.1727 0.091 Uiso 1 1 calc GR . . . .


_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
O1 C4 1.452(2) . ?
O1 C5 1.3562(19) . ?
O2 C11 1.3391(19) . ?
O2 C12 1.4611(19) . ?
N1 C3 1.485(2) . ?
N1 C5 1.262(2) . ?
N2 C6 1.339(2) . ?
N2 C10 1.341(2) . ?
N3 C11 1.268(2) . ?
N3 C13 1.491(2) . ?
C1 C3 1.524(3) . ?
C2 C3 1.517(3) . ?
C3 C4 1.540(2) . ?
C5 C6 1.483(2) . ?
C6 C7 1.391(2) . ?
C7 C8 1.391(2) . ?
C8 C9 1.396(2) . ?
C8 C16 1.487(2) . ?
C9 C10 1.393(2) . ?
C10 C11 1.488(2) . ?
C12 C13 1.543(2) . ?
C13 C14 1.524(3) . ?
C13 C15 1.515(3) . ?
C16 C17 1.394(2) . ?
C16 C21 1.397(2) . ?
C17 C18 1.383(2) . ?
C18 C19 1.399(2) . ?
C19 C20 1.399(2) . ?
C19 C22 1.484(2) . ?
C20 C21 1.386(2) . ?
C22 C23 1.400(2) . ?
C22 C24 1.397(2) 2_776 ?
C23 C24 1.384(2) . ?
C24 C22 1.397(2) 2_776 ?
O3 C25 1.411(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
C5 O1 C4 104.69(13) . . ?
C11 O2 C12 105.72(12) . . ?
C5 N1 C3 107.21(14) . . ?
C6 N2 C10 115.79(13) . . ?
C11 N3 C13 107.20(13) . . ?
N1 C3 C1 108.13(16) . . ?
N1 C3 C2 109.86(17) . . ?
N1 C3 C4 102.48(14) . . ?
C1 C3 C4 112.76(17) . . ?
C2 C3 C1 111.05(16) . . ?
C2 C3 C4 112.14(17) . . ?
O1 C4 C3 104.81(14) . . ?
O1 C5 C6 117.47(14) . . ?
N1 C5 O1 119.01(15) . . ?
N1 C5 C6 123.50(15) . . ?
N2 C6 C5 117.93(14) . . ?
N2 C6 C7 124.23(15) . . ?
C7 C6 C5 117.79(14) . . ?
C6 C7 C8 119.67(15) . . ?
C7 C8 C9 116.62(14) . . ?
C7 C8 C16 121.40(14) . . ?
C9 C8 C16 121.95(15) . . ?
C10 C9 C8 119.54(15) . . ?
N2 C10 C9 124.12(14) . . ?
N2 C10 C11 116.57(13) . . ?
C9 C10 C11 119.29(14) . . ?
O2 C11 C10 116.11(13) . . ?
N3 C11 O2 118.99(14) . . ?
N3 C11 C10 124.89(14) . . ?
O2 C12 C13 104.23(13) . . ?
N3 C13 C12 102.86(13) . . ?
N3 C13 C14 108.75(15) . . ?
N3 C13 C15 109.00(14) . . ?
C14 C13 C12 112.06(17) . . ?
C15 C13 C12 112.64(16) . . ?
C15 C13 C14 111.11(16) . . ?
C17 C16 C8 121.84(15) . . ?
C17 C16 C21 117.98(15) . . ?
C21 C16 C8 120.16(15) . . ?
C18 C17 C16 120.91(15) . . ?
C17 C18 C19 121.27(16) . . ?
C18 C19 C22 121.05(15) . . ?
C20 C19 C18 117.88(15) . . ?
C20 C19 C22 121.07(15) . . ?
C21 C20 C19 120.67(15) . . ?
C20 C21 C16 121.28(15) . . ?
C23 C22 C19 120.91(15) . . ?
C24 C22 C19 121.52(15) 2_776 . ?
C24 C22 C23 117.57(15) 2_776 . ?
C24 C23 C22 121.27(16) . . ?
C23 C24 C22 121.16(16) . 2_776 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method chloroform/methanol
####################################################################### 
# 
# 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_C1
_database_code_depnum_ccdc_archive 'CCDC 1478955'
_audit_update_record             
;
2016-05-10 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;
_audit_creation_date             2016-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            C1
_chemical_name_systematic        C1
_chemical_formula_moiety         'C30 H36 Br2 N6 O4 Zn, Cl2 O8'
_chemical_formula_sum            'C30 H36 Br2 Cl2 N6 O12 Zn'
_chemical_formula_weight         968.74
_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'
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'
Zn Zn 0.2839 1.4301 '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           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'

_cell_length_a                   11.337(4)
_cell_length_b                   19.412(7)
_cell_length_c                   33.776(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7433(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5403
_cell_measurement_temperature    293.1500
_cell_measurement_theta_max      27.4778
_cell_measurement_theta_min      1.2058
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.023
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5933
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3904
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7208
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         2.166
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.1231
	          2theta: -20.1757
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   ?
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1791
_reflns_number_total             2133
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.00023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.216
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0610
_refine_ls_restrained_S_all      1.216
_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)+(0.0433P)²+39.4377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1394
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: O2(0.5) O3(0.5) O4(0.5) O5(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.3750 0.72081(3) 0.3750 0.0745(3) Uani 1 2 d S T P . .
Zn1 Zn 0.3750 0.3750 0.3750 0.0389(3) Uani 1 4 d S T P . .
O1 O 0.5907(3) 0.50000(15) 0.45041(9) 0.0526(8) Uani 1 1 d . . . . .
N1 N 0.3750 0.4837(2) 0.3750 0.0341(9) Uani 1 2 d S T P . .
N2 N 0.5107(3) 0.40674(16) 0.42120(9) 0.0383(7) Uani 1 1 d . . . . .
C1 C 0.3750 0.6245(3) 0.3750 0.0427(13) Uani 1 2 d S T P . .
C2 C 0.4482(4) 0.5895(2) 0.40070(12) 0.0417(9) Uani 1 1 d . . . . .
H2 H 0.4976 0.6129 0.4181 0.050 Uiso 1 1 calc R . . . .
C3 C 0.4455(3) 0.51809(19) 0.39959(11) 0.0350(8) Uani 1 1 d . . . . .
C4 C 0.5168(3) 0.4721(2) 0.42411(11) 0.0376(8) Uani 1 1 d . . . . .
C5 C 0.6476(5) 0.4423(2) 0.46988(17) 0.0670(15) Uani 1 1 d . . . . .
H5A H 0.6305 0.4426 0.4980 0.080 Uiso 1 1 calc R . . . .
H5B H 0.7324 0.4445 0.4663 0.080 Uiso 1 1 calc R . . . .
C6 C 0.5968(4) 0.3771(2) 0.45024(12) 0.0434(9) Uani 1 1 d . . . . .
C7 C 0.5318(5) 0.3323(3) 0.47939(15) 0.0709(15) Uani 1 1 d . . . . .
H7A H 0.4740 0.3594 0.4931 0.106 Uiso 1 1 calc GR . . . .
H7B H 0.5868 0.3135 0.4981 0.106 Uiso 1 1 calc GR . . . .
H7C H 0.4933 0.2955 0.4655 0.106 Uiso 1 1 calc GR . . . .
C8 C 0.6907(4) 0.3375(3) 0.42850(15) 0.0652(14) Uani 1 1 d . . . . .
H8A H 0.6553 0.2995 0.4147 0.098 Uiso 1 1 calc GR . . . .
H8B H 0.7477 0.3204 0.4471 0.098 Uiso 1 1 calc GR . . . .
H8C H 0.7290 0.3673 0.4098 0.098 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.1250 0.6250 0.45301(5) 0.0607(5) Uani 1 2 d S T P . .
O2 O 0.0792(10) 0.5865(6) 0.4857(3) 0.106(4) Uani 0.5 1 d . . . A -1
O3 O 0.1429(9) 0.5821(5) 0.4189(3) 0.098(3) Uani 0.5 1 d . . . A -1
O4 O 0.0399(9) 0.6757(5) 0.4431(3) 0.092(3) Uani 0.5 1 d . . . A -1
O5 O 0.2341(9) 0.6556(7) 0.4636(3) 0.106(4) Uani 0.5 1 d . . . A -1


_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 C1 1.869(5) . ?
Zn1 N1 2.110(4) . ?
Zn1 N1 2.110(4) 2 ?
Zn1 N2 2.276(3) . ?
Zn1 N2 2.276(3) 3 ?
Zn1 N2 2.276(3) 4 ?
Zn1 N2 2.276(3) 2 ?
O1 C4 1.337(4) . ?
O1 C5 1.449(6) . ?
N1 C3 1.332(4) 3 ?
N1 C3 1.332(4) . ?
N2 C4 1.273(5) . ?
N2 C6 1.499(5) . ?
C1 C2 1.380(5) . ?
C1 C2 1.380(5) 3 ?
C2 H2 0.9300 . ?
C2 C3 1.387(5) . ?
C3 C4 1.462(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.542(6) . ?
C6 C7 1.506(6) . ?
C6 C8 1.504(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
Cl1 O2 1.430(10) . ?
Cl1 O3 1.435(9) . ?
Cl1 O4 1.419(9) . ?
Cl1 O5 1.418(10) . ?

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
N1 Zn1 N1 180.0 . 2 ?
N1 Zn1 N2 105.71(8) . 4 ?
N1 Zn1 N2 74.29(8) 2 2 ?
N1 Zn1 N2 105.71(8) 2 3 ?
N1 Zn1 N2 105.71(8) 2 . ?
N1 Zn1 N2 105.71(8) . 2 ?
N1 Zn1 N2 74.29(8) 2 4 ?
N1 Zn1 N2 74.29(8) . . ?
N1 Zn1 N2 74.29(8) . 3 ?
N2 Zn1 N2 93.42(17) 3 4 ?
N2 Zn1 N2 94.98(17) . 4 ?
N2 Zn1 N2 148.59(16) . 3 ?
N2 Zn1 N2 94.98(17) 3 2 ?
N2 Zn1 N2 148.59(16) 4 2 ?
N2 Zn1 N2 93.43(17) . 2 ?
C4 O1 C5 105.5(3) . . ?
C3 N1 Zn1 120.1(2) . . ?
C3 N1 Zn1 120.1(2) 3 . ?
C3 N1 C3 119.8(5) 3 . ?
C4 N2 Zn1 111.0(3) . . ?
C4 N2 C6 107.2(3) . . ?
C6 N2 Zn1 141.7(3) . . ?
C2 C1 Br1 119.5(3) 3 . ?
C2 C1 Br1 119.5(3) . . ?
C2 C1 C2 120.9(5) . 3 ?
C1 C2 H2 121.2 . . ?
C1 C2 C3 117.5(4) . . ?
C3 C2 H2 121.2 . . ?
N1 C3 C2 122.1(4) . . ?
N1 C3 C4 112.2(3) . . ?
C2 C3 C4 125.7(3) . . ?
O1 C4 C3 118.4(3) . . ?
N2 C4 O1 119.3(4) . . ?
N2 C4 C3 122.3(3) . . ?
O1 C5 H5A 110.6 . . ?
O1 C5 H5B 110.6 . . ?
O1 C5 C6 105.8(3) . . ?
H5A C5 H5B 108.7 . . ?
C6 C5 H5A 110.6 . . ?
C6 C5 H5B 110.6 . . ?
N2 C6 C5 102.1(3) . . ?
N2 C6 C7 109.3(3) . . ?
N2 C6 C8 109.7(3) . . ?
C7 C6 C5 112.1(4) . . ?
C8 C6 C5 111.4(4) . . ?
C8 C6 C7 111.7(4) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 Cl1 O3 111.6(7) . . ?
O4 Cl1 O2 107.3(6) . . ?
O4 Cl1 O3 108.0(7) . . ?
O5 Cl1 O2 109.9(7) . . ?
O5 Cl1 O3 108.8(6) . . ?
O5 Cl1 O4 111.2(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C3 -179.8(2) . . . . ?
Zn1 N1 C3 C2 -179.8(3) . . . . ?
Zn1 N1 C3 C4 0.3(4) . . . . ?
Zn1 N2 C4 O1 178.9(3) . . . . ?
Zn1 N2 C4 C3 -1.2(5) . . . . ?
Zn1 N2 C6 C5 -178.2(4) . . . . ?
Zn1 N2 C6 C7 -59.3(6) . . . . ?
Zn1 N2 C6 C8 63.6(6) . . . . ?
O1 C5 C6 N2 -1.4(5) . . . . ?
O1 C5 C6 C7 -118.3(5) . . . . ?
O1 C5 C6 C8 115.7(4) . . . . ?
N1 C3 C4 O1 -179.4(3) . . . . ?
N1 C3 C4 N2 0.6(5) . . . . ?
C1 C2 C3 N1 -0.3(5) . . . . ?
C1 C2 C3 C4 179.5(3) . . . . ?
C2 C1 C2 C3 0.2(2) 3 . . . ?
C2 C3 C4 O1 0.8(6) . . . . ?
C2 C3 C4 N2 -179.2(4) . . . . ?
C3 N1 C3 C2 0.2(3) 3 . . . ?
C3 N1 C3 C4 -179.7(4) 3 . . . ?
C4 O1 C5 C6 1.0(5) . . . . ?
C4 N2 C6 C5 1.3(5) . . . . ?
C4 N2 C6 C7 120.2(4) . . . . ?
C4 N2 C6 C8 -117.0(4) . . . . ?
C5 O1 C4 N2 -0.2(6) . . . . ?
C5 O1 C4 C3 179.9(4) . . . . ?
C6 N2 C4 O1 -0.8(5) . . . . ?
C6 N2 C4 C3 179.2(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method acetonitrile/ether
_chemical_compound_source        none
_exptl_crystal_preparation       Luminescent
