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

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

data_compound1
_database_code_depnum_ccdc_archive 'CCDC 1414630'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 N4'
_chemical_formula_sum            'C19 H16 N4'
_chemical_formula_weight         300.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.5221(9)
_cell_length_b                   14.646(2)
_cell_length_c                   9.6251(15)
_cell_angle_alpha                90
_cell_angle_beta                 97.844(6)
_cell_angle_gamma                90
_cell_volume                     771.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    45
_cell_measurement_theta_min      7.94
_cell_measurement_theta_max      40.72

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.252
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         microsource
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11094
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.782
_diffrn_reflns_theta_max         27.163
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3402
_reflns_number_gt                2439
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'Bruker Instrument Service v3.0.31'
_computing_cell_refinement       'APEX2 v2013.10-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    Superflip
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_special_details          
;
 The compound is a weak anomalous scatterer with respect to Mo radiation, thus
 no absolute configuration was determined.
 The N-H proton H1 is located between the two nitrogen atoms N2 and N4. Within
 the accuracy of the measurement, no clear decision can be made as to whether
 a rather symmetric configuration or a superposition of two "normal" N-H...H
 configurations is present. As the former is the natural interpretation of the
 electron density map, it was arbitrarily chosen in this case.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0883P)²+0.0658P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 928 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3402
_refine_ls_number_parameters     211
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1582
_refine_ls_wR_factor_gt          0.1403
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0103(7) 0.7542(2) -0.1624(4) 0.0275(9) Uani 1 1 d . . . . .
C2 C 0.9270(7) 0.8165(3) -0.2776(4) 0.0272(9) Uani 1 1 d . . . . .
C3 C 1.0584(8) 0.8268(3) -0.3911(5) 0.0360(11) Uani 1 1 d . . . . .
H3 H 1.2011 0.7912 -0.3950 0.043 Uiso 1 1 calc R U . . .
C4 C 0.9834(9) 0.8878(3) -0.4971(5) 0.0411(11) Uani 1 1 d . . . . .
H4 H 1.0761 0.8943 -0.5727 0.049 Uiso 1 1 calc R U . . .
C5 C 0.7771(8) 0.9392(3) -0.4949(5) 0.0368(11) Uani 1 1 d . . . . .
H5 H 0.7257 0.9809 -0.5687 0.044 Uiso 1 1 calc R U . . .
C6 C 0.6447(8) 0.9299(3) -0.3844(5) 0.0373(11) Uani 1 1 d . . . . .
H6 H 0.5018 0.9656 -0.3818 0.045 Uiso 1 1 calc R U . . .
C7 C 0.7182(8) 0.8691(3) -0.2777(5) 0.0346(10) Uani 1 1 d . . . . .
H7 H 0.6239 0.8631 -0.2027 0.042 Uiso 1 1 calc R U . . .
C8 C 1.4696(7) 0.5823(2) -0.0935(4) 0.0262(9) Uani 1 1 d . . . . .
C9 C 1.5968(7) 0.5850(3) -0.2077(4) 0.0266(9) Uani 1 1 d . . . . .
H9 H 1.5497 0.6267 -0.2821 0.032 Uiso 1 1 calc R U . . .
C10 C 1.7924(8) 0.5269(3) -0.2135(5) 0.0314(10) Uani 1 1 d . . . . .
H10 H 1.8811 0.5299 -0.2913 0.038 Uiso 1 1 calc R U . . .
C11 C 1.8608(8) 0.4643(3) -0.1075(5) 0.0342(10) Uani 1 1 d . . . . .
H11 H 1.9934 0.4237 -0.1130 0.041 Uiso 1 1 calc R U . . .
C12 C 1.7330(8) 0.4619(3) 0.0067(5) 0.0366(11) Uani 1 1 d . . . . .
H12 H 1.7798 0.4199 0.0807 0.044 Uiso 1 1 calc R U . . .
C13 C 1.5385(8) 0.5199(3) 0.0138(5) 0.0316(10) Uani 1 1 d . . . . .
H13 H 1.4512 0.5174 0.0922 0.038 Uiso 1 1 calc R U . . .
C14 C 0.8219(7) 0.7058(3) 0.1734(4) 0.0256(8) Uani 1 1 d . . . . .
C15 C 0.6226(7) 0.7634(3) 0.1779(4) 0.0299(9) Uani 1 1 d . . . . .
H15 H 0.5745 0.8048 0.1033 0.036 Uiso 1 1 calc R U . . .
C16 C 0.4954(8) 0.7598(3) 0.2916(5) 0.0375(10) Uani 1 1 d . . . . .
H16 H 0.3577 0.7984 0.2941 0.045 Uiso 1 1 calc R U . . .
C17 C 0.5653(8) 0.7012(3) 0.4014(5) 0.0390(10) Uani 1 1 d . . . . .
H17 H 0.4769 0.6998 0.4794 0.047 Uiso 1 1 calc R U . . .
C18 C 0.7654(8) 0.6441(3) 0.3981(5) 0.0361(10) Uani 1 1 d . . . . .
H18 H 0.8132 0.6034 0.4737 0.043 Uiso 1 1 calc R U . . .
C19 C 0.8947(8) 0.6465(3) 0.2852(4) 0.0302(9) Uani 1 1 d . . . . .
H19 H 1.0327 0.6080 0.2834 0.036 Uiso 1 1 calc R U . . .
N1 N 1.1987(6) 0.6986(2) -0.1786(3) 0.0300(8) Uani 1 1 d . . . . .
N2 N 1.2781(6) 0.6408(2) -0.0762(3) 0.0293(8) Uani 1 1 d . . . . .
N3 N 0.8894(6) 0.7571(2) -0.0458(4) 0.0353(9) Uani 1 1 d . . . . .
N4 N 0.9543(6) 0.7039(2) 0.0589(3) 0.0257(7) Uani 1 1 d . . . . .
H1 H 1.136(8) 0.650(3) 0.039(4) 0.031 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.347(5) . ?
C1 N3 1.383(5) . ?
C1 C2 1.461(6) . ?
C2 C7 1.387(6) . ?
C2 C3 1.400(6) . ?
C3 C4 1.377(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.368(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(6) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.384(6) . ?
C8 N2 1.389(5) . ?
C8 C13 1.392(6) . ?
C9 C10 1.382(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.392(5) . ?
C14 C19 1.398(6) . ?
C14 N4 1.403(4) . ?
C15 C16 1.380(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N1 N2 1.328(5) . ?
N2 H1 1.45(4) . ?
N3 N4 1.286(5) . ?
N4 H1 1.31(4) . ?

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 C1 N3 125.4(4) . . ?
N1 C1 C2 117.3(3) . . ?
N3 C1 C2 117.4(3) . . ?
C7 C2 C3 117.3(4) . . ?
C7 C2 C1 121.5(4) . . ?
C3 C2 C1 121.1(3) . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 120.8(5) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.2(4) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C7 120.5(4) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C2 121.3(4) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
C9 C8 N2 123.7(3) . . ?
C9 C8 C13 119.4(4) . . ?
N2 C8 C13 116.8(4) . . ?
C10 C9 C8 119.9(4) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.9(4) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C12 119.0(4) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 120.6(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 120.2(4) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C15 C14 C19 119.9(3) . . ?
C15 C14 N4 122.3(3) . . ?
C19 C14 N4 117.8(3) . . ?
C16 C15 C14 119.5(4) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C15 120.9(4) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 119.9(4) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 119.7(4) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
N2 N1 C1 118.8(3) . . ?
N1 N2 C8 119.0(3) . . ?
N1 N2 H1 110.5(18) . . ?
C8 N2 H1 130.5(18) . . ?
N4 N3 C1 120.3(3) . . ?
N3 N4 C14 119.0(3) . . ?
N3 N4 H1 112.7(18) . . ?
C14 N4 H1 128.2(18) . . ?

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
N1 C1 C2 C7 172.8(4) . . . . ?
N3 C1 C2 C7 -7.2(5) . . . . ?
N1 C1 C2 C3 -8.5(5) . . . . ?
N3 C1 C2 C3 171.5(3) . . . . ?
C7 C2 C3 C4 0.9(6) . . . . ?
C1 C2 C3 C4 -177.9(4) . . . . ?
C2 C3 C4 C5 -0.7(7) . . . . ?
C3 C4 C5 C6 0.5(7) . . . . ?
C4 C5 C6 C7 -0.4(7) . . . . ?
C5 C6 C7 C2 0.6(7) . . . . ?
C3 C2 C7 C6 -0.8(6) . . . . ?
C1 C2 C7 C6 177.9(4) . . . . ?
N2 C8 C9 C10 177.1(3) . . . . ?
C13 C8 C9 C10 -0.9(5) . . . . ?
C8 C9 C10 C11 1.3(6) . . . . ?
C9 C10 C11 C12 -1.3(6) . . . . ?
C10 C11 C12 C13 0.9(6) . . . . ?
C11 C12 C13 C8 -0.5(6) . . . . ?
C9 C8 C13 C12 0.5(6) . . . . ?
N2 C8 C13 C12 -177.6(3) . . . . ?
C19 C14 C15 C16 -1.4(6) . . . . ?
N4 C14 C15 C16 177.9(4) . . . . ?
C14 C15 C16 C17 1.0(6) . . . . ?
C15 C16 C17 C18 -0.5(7) . . . . ?
C16 C17 C18 C19 0.3(7) . . . . ?
C17 C18 C19 C14 -0.8(6) . . . . ?
C15 C14 C19 C18 1.3(6) . . . . ?
N4 C14 C19 C18 -178.1(3) . . . . ?
N3 C1 N1 N2 0.3(6) . . . . ?
C2 C1 N1 N2 -179.7(3) . . . . ?
C1 N1 N2 C8 178.9(3) . . . . ?
C9 C8 N2 N1 5.0(5) . . . . ?
C13 C8 N2 N1 -177.0(3) . . . . ?
N1 C1 N3 N4 0.0(6) . . . . ?
C2 C1 N3 N4 180.0(3) . . . . ?
C1 N3 N4 C14 -177.5(3) . . . . ?
C15 C14 N4 N3 -0.1(5) . . . . ?
C19 C14 N4 N3 179.3(4) . . . . ?

_refine_diff_density_max         0.653
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.053

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_compound2
_database_code_depnum_ccdc_archive 'CCDC 1414631'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 Al N4'
_chemical_formula_sum            'C21 H21 Al N4'
_chemical_formula_weight         356.40

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'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P c a n'
_space_group_name_Hall           '-P 2n 2c'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x, y, z-1/2'
'x-1/2, -y-1/2, z'

_cell_length_a                   7.1385(3)
_cell_length_b                   12.8158(5)
_cell_length_c                   40.238(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3681.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6315
_cell_measurement_theta_min      1.88
_cell_measurement_theta_max      27.15

_exptl_crystal_description       needle
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9625
_exptl_absorpt_correction_T_max  1.0024
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            16826
_diffrn_reflns_av_unetI/netI     0.0935
_diffrn_reflns_av_R_equivalents  0.0862
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         1.884
_diffrn_reflns_theta_max         26.712
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3888
_reflns_number_gt                1978
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0336P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3888
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.0848
_refine_ls_wR_factor_gt          0.0742
_refine_ls_goodness_of_fit_ref   0.763
_refine_ls_restrained_S_all      0.763
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2999(3) 0.20035(16) 0.14023(5) 0.0317(5) Uani 1 1 d . . . . .
C2 C 0.3022(3) 0.29899(15) 0.15983(5) 0.0307(5) Uani 1 1 d . . . . .
C3 C 0.2558(3) 0.30040(17) 0.19337(5) 0.0368(6) Uani 1 1 d . . . . .
H3 H 0.2243 0.2370 0.2042 0.044 Uiso 1 1 calc R U . . .
C4 C 0.2548(3) 0.39335(17) 0.21126(5) 0.0383(6) Uani 1 1 d . . . . .
H4 H 0.2214 0.3935 0.2341 0.046 Uiso 1 1 calc R U . . .
C5 C 0.3030(3) 0.48565(18) 0.19552(5) 0.0378(5) Uani 1 1 d . . . . .
H5 H 0.3038 0.5493 0.2076 0.045 Uiso 1 1 calc R U . . .
C6 C 0.3494(3) 0.48532(17) 0.16248(5) 0.0359(5) Uani 1 1 d . . . . .
H6 H 0.3814 0.5490 0.1518 0.043 Uiso 1 1 calc R U . . .
C7 C 0.3502(3) 0.39331(16) 0.14439(5) 0.0333(5) Uani 1 1 d . . . . .
H7 H 0.3832 0.3942 0.1215 0.040 Uiso 1 1 calc R U . . .
C8 C 0.3680(3) -0.06023(15) 0.16790(5) 0.0310(5) Uani 1 1 d . . . . .
C9 C 0.3097(3) -0.04947(16) 0.20071(5) 0.0348(5) Uani 1 1 d . . . . .
H9 H 0.2444 0.0115 0.2075 0.042 Uiso 1 1 calc R U . . .
C10 C 0.3473(4) -0.12809(16) 0.22330(5) 0.0369(5) Uani 1 1 d . . . . .
H10 H 0.3094 -0.1207 0.2458 0.044 Uiso 1 1 calc R U . . .
C11 C 0.4405(3) -0.21801(17) 0.21313(5) 0.0353(5) Uani 1 1 d . . . . .
H11 H 0.4678 -0.2713 0.2288 0.042 Uiso 1 1 calc R U . . .
C12 C 0.4932(3) -0.22988(16) 0.18043(6) 0.0354(5) Uani 1 1 d . . . . .
H12 H 0.5544 -0.2920 0.1735 0.042 Uiso 1 1 calc R U . . .
C13 C 0.4573(3) -0.15150(16) 0.15746(6) 0.0339(5) Uani 1 1 d . . . . .
H13 H 0.4931 -0.1599 0.1349 0.041 Uiso 1 1 calc R U . . .
C14 C 0.2125(3) 0.16553(16) 0.05395(5) 0.0311(5) Uani 1 1 d . . . . .
C15 C 0.1945(3) 0.27009(16) 0.04475(5) 0.0349(5) Uani 1 1 d . . . . .
H15 H 0.2089 0.3234 0.0609 0.042 Uiso 1 1 calc R U . . .
C16 C 0.1562(3) 0.29593(18) 0.01237(5) 0.0375(5) Uani 1 1 d . . . . .
H16 H 0.1446 0.3673 0.0064 0.045 Uiso 1 1 calc R U . . .
C17 C 0.1341(3) 0.21921(18) -0.01186(6) 0.0377(6) Uani 1 1 d . . . . .
H17 H 0.1081 0.2378 -0.0342 0.045 Uiso 1 1 calc R U . . .
C18 C 0.1507(4) 0.11538(17) -0.00274(5) 0.0374(6) Uani 1 1 d . . . . .
H18 H 0.1350 0.0623 -0.0190 0.045 Uiso 1 1 calc R U . . .
C19 C 0.1901(3) 0.08821(17) 0.02992(5) 0.0343(5) Uani 1 1 d . . . . .
H19 H 0.2019 0.0168 0.0359 0.041 Uiso 1 1 calc R U . . .
C20 C 0.1192(3) -0.11083(16) 0.09036(6) 0.0386(6) Uani 1 1 d . . . . .
H20A H 0.1136 -0.1585 0.1094 0.058 Uiso 1 1 calc R U . . .
H20B H 0.1419 -0.1509 0.0700 0.058 Uiso 1 1 calc R U . . .
H20C H 0.0002 -0.0732 0.0884 0.058 Uiso 1 1 calc R U . . .
C21 C 0.5634(4) -0.04319(17) 0.07615(6) 0.0407(6) Uani 1 1 d . . . . .
H21A H 0.6633 -0.0042 0.0873 0.061 Uiso 1 1 calc R U . . .
H21B H 0.5593 -0.0235 0.0526 0.061 Uiso 1 1 calc R U . . .
H21C H 0.5880 -0.1182 0.0781 0.061 Uiso 1 1 calc R U . . .
N1 N 0.3290(3) 0.11348(12) 0.15844(4) 0.0314(4) Uani 1 1 d . . . . .
N2 N 0.3418(3) 0.02182(13) 0.14384(4) 0.0320(4) Uani 1 1 d . . . . .
N3 N 0.2650(3) 0.21305(13) 0.10777(4) 0.0324(4) Uani 1 1 d . . . . .
N4 N 0.2580(3) 0.13386(13) 0.08703(4) 0.0314(4) Uani 1 1 d . . . . .
Al1 Al 0.32336(10) -0.01063(5) 0.09695(2) 0.03247(16) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N3 1.340(3) . ?
C1 N1 1.349(2) . ?
C1 C2 1.490(3) . ?
C2 C3 1.389(3) . ?
C2 C7 1.402(3) . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.370(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.391(3) . ?
C8 C13 1.397(3) . ?
C8 N2 1.442(3) . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.394(3) . ?
C14 C15 1.396(3) . ?
C14 N4 1.429(3) . ?
C15 C16 1.372(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.394(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 Al1 1.960(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 Al1 1.952(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N1 N2 1.317(2) . ?
N2 Al1 1.9366(17) . ?
N3 N4 1.315(2) . ?
N4 Al1 1.9507(18) . ?

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
N3 C1 N1 131.18(19) . . ?
N3 C1 C2 114.52(18) . . ?
N1 C1 C2 114.27(17) . . ?
C3 C2 C7 118.52(19) . . ?
C3 C2 C1 121.49(18) . . ?
C7 C2 C1 119.99(19) . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C2 120.0(2) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C9 C8 C13 120.3(2) . . ?
C9 C8 N2 121.75(19) . . ?
C13 C8 N2 117.90(19) . . ?
C10 C9 C8 119.6(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 119.3(2) . . ?
C12 C13 H13 120.3 . . ?
C8 C13 H13 120.3 . . ?
C19 C14 C15 119.2(2) . . ?
C19 C14 N4 118.05(18) . . ?
C15 C14 N4 122.71(18) . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 121.1(2) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 118.9(2) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C17 C18 C19 120.6(2) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 120.1(2) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
Al1 C20 H20A 109.5 . . ?
Al1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Al1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Al1 C21 H21A 109.5 . . ?
Al1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
Al1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 N1 C1 120.31(17) . . ?
N1 N2 C8 111.10(16) . . ?
N1 N2 Al1 128.43(13) . . ?
C8 N2 Al1 120.44(13) . . ?
N4 N3 C1 122.16(18) . . ?
N3 N4 C14 112.38(16) . . ?
N3 N4 Al1 126.42(14) . . ?
C14 N4 Al1 120.97(13) . . ?
N2 Al1 N4 90.68(7) . . ?
N2 Al1 C21 113.82(10) . . ?
N4 Al1 C21 108.97(9) . . ?
N2 Al1 C20 108.84(9) . . ?
N4 Al1 C20 114.61(9) . . ?
C21 Al1 C20 117.03(10) . . ?

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
N3 C1 C2 C3 151.9(2) . . . . ?
N1 C1 C2 C3 -26.7(3) . . . . ?
N3 C1 C2 C7 -27.5(3) . . . . ?
N1 C1 C2 C7 154.0(2) . . . . ?
C7 C2 C3 C4 0.7(4) . . . . ?
C1 C2 C3 C4 -178.7(2) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C5 C6 C7 -0.4(4) . . . . ?
C5 C6 C7 C2 0.3(4) . . . . ?
C3 C2 C7 C6 -0.4(4) . . . . ?
C1 C2 C7 C6 178.9(2) . . . . ?
C13 C8 C9 C10 2.6(3) . . . . ?
N2 C8 C9 C10 -176.4(2) . . . . ?
C8 C9 C10 C11 -1.0(3) . . . . ?
C9 C10 C11 C12 -1.0(4) . . . . ?
C10 C11 C12 C13 1.3(4) . . . . ?
C11 C12 C13 C8 0.3(3) . . . . ?
C9 C8 C13 C12 -2.3(3) . . . . ?
N2 C8 C13 C12 176.8(2) . . . . ?
C19 C14 C15 C16 -0.3(4) . . . . ?
N4 C14 C15 C16 178.0(2) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C14 0.3(4) . . . . ?
C15 C14 C19 C18 0.1(4) . . . . ?
N4 C14 C19 C18 -178.3(2) . . . . ?
N3 C1 N1 N2 6.0(4) . . . . ?
C2 C1 N1 N2 -175.8(2) . . . . ?
C1 N1 N2 C8 -178.5(2) . . . . ?
C1 N1 N2 Al1 -0.3(3) . . . . ?
C9 C8 N2 N1 24.4(3) . . . . ?
C13 C8 N2 N1 -154.6(2) . . . . ?
C9 C8 N2 Al1 -153.99(18) . . . . ?
C13 C8 N2 Al1 27.0(3) . . . . ?
N1 C1 N3 N4 -1.8(4) . . . . ?
C2 C1 N3 N4 -179.97(19) . . . . ?
C1 N3 N4 C14 178.0(2) . . . . ?
C1 N3 N4 Al1 -7.7(3) . . . . ?
C19 C14 N4 N3 -176.4(2) . . . . ?
C15 C14 N4 N3 5.3(3) . . . . ?
C19 C14 N4 Al1 8.9(3) . . . . ?
C15 C14 N4 Al1 -169.43(18) . . . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.042

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_compound3
_database_code_depnum_ccdc_archive 'CCDC 1414632'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 Ga1 N4'
_chemical_formula_sum            'C21 H21 Ga N4'
_chemical_formula_weight         399.14

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'
Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P c a n'
_space_group_name_Hall           '-P 2n 2c'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x, y, z-1/2'
'x-1/2, -y-1/2, z'

_cell_length_a                   7.1385(3)
_cell_length_b                   12.8158(5)
_cell_length_c                   40.238(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3681.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9020
_cell_measurement_theta_min      4.46
_cell_measurement_theta_max      27.2

_exptl_crystal_description       plate
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             1648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.507
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7552
_exptl_absorpt_correction_T_max  0.9713
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            16804
_diffrn_reflns_av_unetI/netI     0.0940
_diffrn_reflns_av_R_equivalents  0.1017
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         4.536
_diffrn_reflns_theta_max         26.924
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3781
_reflns_number_gt                2457
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2004)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0276P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3781
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.0775
_refine_ls_wR_factor_gt          0.0692
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_restrained_S_all      0.894
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2962(4) 0.1984(2) 0.14017(7) 0.0133(7) Uani 1 1 d . . . . .
C2 C 0.2967(4) 0.2972(2) 0.15957(7) 0.0128(7) Uani 1 1 d . . . . .
C3 C 0.2467(5) 0.2985(2) 0.19299(8) 0.0174(7) Uani 1 1 d . . . . .
H3 H 0.2135 0.2352 0.2037 0.021 Uiso 1 1 calc R U . . .
C4 C 0.2447(5) 0.3913(2) 0.21086(9) 0.0216(8) Uani 1 1 d . . . . .
H4 H 0.2085 0.3911 0.2336 0.026 Uiso 1 1 calc R U . . .
C5 C 0.2955(4) 0.4841(2) 0.19566(8) 0.0201(7) Uani 1 1 d . . . . .
H5 H 0.2961 0.5474 0.2080 0.024 Uiso 1 1 calc R U . . .
C6 C 0.3452(4) 0.4838(2) 0.16256(8) 0.0194(7) Uani 1 1 d . . . . .
H6 H 0.3776 0.5474 0.1519 0.023 Uiso 1 1 calc R U . . .
C7 C 0.3481(4) 0.3911(2) 0.14480(8) 0.0175(7) Uani 1 1 d . . . . .
H7 H 0.3858 0.3917 0.1222 0.021 Uiso 1 1 calc R U . . .
C8 C 0.3638(4) -0.0614(2) 0.16838(8) 0.0140(7) Uani 1 1 d . . . . .
C9 C 0.3061(5) -0.0500(2) 0.20110(8) 0.0168(7) Uani 1 1 d . . . . .
H9 H 0.2422 0.0114 0.2079 0.020 Uiso 1 1 calc R U . . .
C10 C 0.3424(5) -0.1291(2) 0.22385(8) 0.0207(7) Uani 1 1 d . . . . .
H10 H 0.3041 -0.1211 0.2463 0.025 Uiso 1 1 calc R U . . .
C11 C 0.4342(4) -0.2195(2) 0.21408(8) 0.0193(8) Uani 1 1 d . . . . .
H11 H 0.4609 -0.2726 0.2299 0.023 Uiso 1 1 calc R U . . .
C12 C 0.4862(4) -0.2318(2) 0.18136(8) 0.0176(7) Uani 1 1 d . . . . .
H12 H 0.5460 -0.2945 0.1745 0.021 Uiso 1 1 calc R U . . .
C13 C 0.4519(4) -0.1533(2) 0.15822(8) 0.0150(7) Uani 1 1 d . . . . .
H13 H 0.4882 -0.1622 0.1357 0.018 Uiso 1 1 calc R U . . .
C14 C 0.2131(4) 0.1656(2) 0.05372(8) 0.0140(7) Uani 1 1 d . . . . .
C15 C 0.1948(4) 0.2714(2) 0.04483(8) 0.0178(7) Uani 1 1 d . . . . .
H15 H 0.2081 0.3245 0.0611 0.021 Uiso 1 1 calc R U . . .
C16 C 0.1576(4) 0.2972(2) 0.01233(8) 0.0197(7) Uani 1 1 d . . . . .
H16 H 0.1472 0.3686 0.0063 0.024 Uiso 1 1 calc R U . . .
C17 C 0.1348(4) 0.2209(2) -0.01173(9) 0.0208(7) Uani 1 1 d . . . . .
H17 H 0.1093 0.2397 -0.0341 0.025 Uiso 1 1 calc R U . . .
C18 C 0.1498(4) 0.1169(2) -0.00284(8) 0.0188(7) Uani 1 1 d . . . . .
H18 H 0.1325 0.0642 -0.0192 0.023 Uiso 1 1 calc R U . . .
C19 C 0.1896(4) 0.0890(2) 0.02953(8) 0.0188(7) Uani 1 1 d . . . . .
H19 H 0.2011 0.0174 0.0353 0.023 Uiso 1 1 calc R U . . .
C20 C 0.1125(4) -0.1131(2) 0.09065(8) 0.0210(8) Uani 1 1 d . . . . .
H20A H 0.1047 -0.1591 0.1101 0.031 Uiso 1 1 calc R U . . .
H20B H 0.1324 -0.1551 0.0706 0.031 Uiso 1 1 calc R U . . .
H20C H -0.0045 -0.0737 0.0885 0.031 Uiso 1 1 calc R U . . .
C21 C 0.5692(4) -0.0433(2) 0.07661(8) 0.0193(7) Uani 1 1 d . . . . .
H21A H 0.6647 -0.0022 0.0882 0.029 Uiso 1 1 calc R U . . .
H21B H 0.5676 -0.0238 0.0531 0.029 Uiso 1 1 calc R U . . .
H21C H 0.5986 -0.1177 0.0787 0.029 Uiso 1 1 calc R U . . .
N1 N 0.3240(4) 0.11178(16) 0.15842(6) 0.0136(5) Uani 1 1 d . . . . .
N2 N 0.3386(3) 0.01988(17) 0.14464(6) 0.0147(5) Uani 1 1 d . . . . .
N3 N 0.2626(3) 0.21222(18) 0.10762(6) 0.0133(6) Uani 1 1 d . . . . .
N4 N 0.2565(3) 0.13377(18) 0.08667(6) 0.0137(6) Uani 1 1 d . . . . .
Ga1 Ga 0.32279(5) -0.01564(2) 0.09629(2) 0.01401(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N3 1.343(4) . ?
C1 N1 1.346(3) . ?
C1 C2 1.487(4) . ?
C2 C3 1.391(4) . ?
C2 C7 1.392(4) . ?
C3 C4 1.390(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.387(4) . ?
C8 C13 1.396(4) . ?
C8 N2 1.425(4) . ?
C9 C10 1.390(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.393(4) . ?
C14 C15 1.409(4) . ?
C14 N4 1.422(4) . ?
C15 C16 1.375(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 Ga1 1.966(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 Ga1 1.962(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N1 N2 1.306(3) . ?
N2 Ga1 2.001(2) . ?
N3 N4 1.313(3) . ?
N4 Ga1 2.010(2) . ?

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
N3 C1 N1 131.8(3) . . ?
N3 C1 C2 113.6(2) . . ?
N1 C1 C2 114.5(3) . . ?
C3 C2 C7 118.0(3) . . ?
C3 C2 C1 121.1(3) . . ?
C7 C2 C1 120.8(3) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 120.3(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 121.1(3) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
C9 C8 C13 120.0(3) . . ?
C9 C8 N2 121.5(3) . . ?
C13 C8 N2 118.5(3) . . ?
C8 C9 C10 119.5(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 119.5(3) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
C19 C14 C15 119.4(3) . . ?
C19 C14 N4 118.4(2) . . ?
C15 C14 N4 122.2(3) . . ?
C16 C15 C14 119.4(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 119.3(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C14 120.1(3) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
Ga1 C20 H20A 109.5 . . ?
Ga1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Ga1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Ga1 C21 H21A 109.5 . . ?
Ga1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
Ga1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 N1 C1 121.6(3) . . ?
N1 N2 C8 112.6(2) . . ?
N1 N2 Ga1 127.84(19) . . ?
C8 N2 Ga1 119.51(18) . . ?
N4 N3 C1 122.1(2) . . ?
N3 N4 C14 112.7(2) . . ?
N3 N4 Ga1 126.73(19) . . ?
C14 N4 Ga1 120.29(18) . . ?
C21 Ga1 C20 121.56(13) . . ?
C21 Ga1 N2 112.51(12) . . ?
C20 Ga1 N2 107.45(12) . . ?
C21 Ga1 N4 107.80(11) . . ?
C20 Ga1 N4 113.77(11) . . ?
N2 Ga1 N4 89.07(10) . . ?

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
N3 C1 C2 C3 151.3(3) . . . . ?
N1 C1 C2 C3 -26.9(4) . . . . ?
N3 C1 C2 C7 -29.0(4) . . . . ?
N1 C1 C2 C7 152.8(3) . . . . ?
C7 C2 C3 C4 1.2(5) . . . . ?
C1 C2 C3 C4 -179.0(3) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
C4 C5 C6 C7 -1.3(5) . . . . ?
C5 C6 C7 C2 1.7(5) . . . . ?
C3 C2 C7 C6 -1.6(5) . . . . ?
C1 C2 C7 C6 178.7(3) . . . . ?
C13 C8 C9 C10 2.2(4) . . . . ?
N2 C8 C9 C10 -176.5(3) . . . . ?
C8 C9 C10 C11 -0.6(5) . . . . ?
C9 C10 C11 C12 -1.3(5) . . . . ?
C10 C11 C12 C13 1.7(4) . . . . ?
C11 C12 C13 C8 -0.1(4) . . . . ?
C9 C8 C13 C12 -1.9(4) . . . . ?
N2 C8 C13 C12 176.9(3) . . . . ?
C19 C14 C15 C16 -1.2(5) . . . . ?
N4 C14 C15 C16 178.3(3) . . . . ?
C14 C15 C16 C17 1.0(5) . . . . ?
C15 C16 C17 C18 0.1(5) . . . . ?
C16 C17 C18 C19 -0.9(4) . . . . ?
C17 C18 C19 C14 0.7(5) . . . . ?
C15 C14 C19 C18 0.3(5) . . . . ?
N4 C14 C19 C18 -179.2(3) . . . . ?
N3 C1 N1 N2 6.4(5) . . . . ?
C2 C1 N1 N2 -175.8(3) . . . . ?
C1 N1 N2 C8 -178.8(3) . . . . ?
C1 N1 N2 Ga1 -0.5(4) . . . . ?
C9 C8 N2 N1 23.4(4) . . . . ?
C13 C8 N2 N1 -155.4(3) . . . . ?
C9 C8 N2 Ga1 -155.0(2) . . . . ?
C13 C8 N2 Ga1 26.2(3) . . . . ?
N1 C1 N3 N4 -2.0(5) . . . . ?
C2 C1 N3 N4 -179.8(2) . . . . ?
C1 N3 N4 C14 178.1(3) . . . . ?
C1 N3 N4 Ga1 -7.7(4) . . . . ?
C19 C14 N4 N3 -175.7(3) . . . . ?
C15 C14 N4 N3 4.8(4) . . . . ?
C19 C14 N4 Ga1 9.7(4) . . . . ?
C15 C14 N4 Ga1 -169.8(2) . . . . ?

_refine_diff_density_max         0.469
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.085

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_compound5
_database_code_depnum_ccdc_archive 'CCDC 1414633'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H31 In N6'
_chemical_formula_sum            'C28 H31 In N6'
_chemical_formula_weight         566.41

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'
In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.9585(8)
_cell_length_b                   10.4646(5)
_cell_length_c                   15.2020(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.804(2)
_cell_angle_gamma                90
_cell_volume                     2608.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    234
_cell_measurement_theta_min      9.37
_cell_measurement_theta_max      55.88

_exptl_crystal_description       block
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.122
_exptl_absorpt_coefficient_mu    0.934
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         microsource
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            81787
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.309
_diffrn_reflns_theta_max         27.966
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6269
_reflns_number_gt                5653
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service v3.0.31'
_computing_cell_refinement       'APEX2 v2013.10-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    Superflip
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0207P)²+1.5288P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6269
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0185
_refine_ls_wR_factor_ref         0.0462
_refine_ls_wR_factor_gt          0.0442
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.31128(8) 0.41556(13) 0.07564(9) 0.0136(2) Uani 1 1 d . . . . .
C2 C 0.37542(8) 0.33006(13) 0.05852(9) 0.0144(3) Uani 1 1 d . . . . .
C3 C 0.38080(9) 0.20271(13) 0.08787(9) 0.0173(3) Uani 1 1 d . . . . .
H3 H 0.3419 0.1699 0.1173 0.021 Uiso 1 1 calc R U . . .
C4 C 0.44250(9) 0.12421(13) 0.07428(10) 0.0210(3) Uani 1 1 d . . . . .
H4 H 0.4462 0.0384 0.0953 0.025 Uiso 1 1 calc R U . . .
C5 C 0.49880(9) 0.17027(14) 0.03013(10) 0.0217(3) Uani 1 1 d . . . . .
H5 H 0.5410 0.1162 0.0209 0.026 Uiso 1 1 calc R U . . .
C6 C 0.49325(9) 0.29580(14) -0.00059(10) 0.0210(3) Uani 1 1 d . . . . .
H6 H 0.5312 0.3273 -0.0317 0.025 Uiso 1 1 calc R U . . .
C7 C 0.43240(8) 0.37508(13) 0.01414(10) 0.0168(3) Uani 1 1 d . . . . .
H7 H 0.4295 0.4612 -0.0063 0.020 Uiso 1 1 calc R U . . .
C8 C 0.12826(8) 0.33346(14) 0.13116(9) 0.0162(3) Uani 1 1 d . . . . .
C9 C 0.12483(9) 0.20164(14) 0.11559(10) 0.0203(3) Uani 1 1 d . . . . .
H9 H 0.1593 0.1631 0.0827 0.024 Uiso 1 1 calc R U . . .
C10 C 0.07084(10) 0.12742(15) 0.14832(11) 0.0255(3) Uani 1 1 d . . . . .
H10 H 0.0680 0.0380 0.1372 0.031 Uiso 1 1 calc R U . . .
C11 C 0.02100(9) 0.18257(16) 0.19715(11) 0.0273(3) Uani 1 1 d . . . . .
H11 H -0.0154 0.1310 0.2200 0.033 Uiso 1 1 calc R U . . .
C12 C 0.02448(9) 0.31287(16) 0.21245(11) 0.0260(3) Uani 1 1 d . . . . .
H12 H -0.0094 0.3507 0.2462 0.031 Uiso 1 1 calc R U . . .
C13 C 0.07729(9) 0.38886(14) 0.17870(10) 0.0214(3) Uani 1 1 d . . . . .
H13 H 0.0785 0.4786 0.1882 0.026 Uiso 1 1 calc R U . . .
C14 C 0.31539(8) 0.73105(13) 0.15596(9) 0.0150(3) Uani 1 1 d . . . . .
C15 C 0.39900(9) 0.74018(13) 0.19784(9) 0.0176(3) Uani 1 1 d . . . . .
H15 H 0.4348 0.6737 0.1903 0.021 Uiso 1 1 calc R U . . .
C16 C 0.42951(9) 0.84618(15) 0.25031(10) 0.0215(3) Uani 1 1 d . . . . .
H16 H 0.4863 0.8519 0.2783 0.026 Uiso 1 1 calc R U . . .
C17 C 0.37798(10) 0.94408(14) 0.26244(10) 0.0235(3) Uani 1 1 d . . . . .
H17 H 0.3993 1.0165 0.2984 0.028 Uiso 1 1 calc R U . . .
C18 C 0.29526(10) 0.93501(14) 0.22165(10) 0.0221(3) Uani 1 1 d . . . . .
H18 H 0.2597 1.0015 0.2298 0.027 Uiso 1 1 calc R U . . .
C19 C 0.26398(9) 0.82950(13) 0.16898(9) 0.0186(3) Uani 1 1 d . . . . .
H19 H 0.2071 0.8242 0.1415 0.022 Uiso 1 1 calc R U . . .
C20 C 0.15441(9) 0.50455(14) -0.10419(10) 0.0214(3) Uani 1 1 d . . . . .
H20A H 0.1194 0.4291 -0.1082 0.032 Uiso 1 1 calc R U . . .
H20B H 0.2106 0.4774 -0.0996 0.032 Uiso 1 1 calc R U . . .
H20C H 0.1350 0.5572 -0.1588 0.032 Uiso 1 1 calc R U . . .
C21 C 0.05905(9) 0.69488(15) 0.07387(11) 0.0235(3) Uani 1 1 d . . . . .
H21A H 0.0418 0.7781 0.0460 0.035 Uiso 1 1 calc R U . . .
H21B H 0.0819 0.7058 0.1395 0.035 Uiso 1 1 calc R U . . .
H21C H 0.0120 0.6373 0.0632 0.035 Uiso 1 1 calc R U . . .
C22 C 0.16171(9) 0.91927(14) -0.05047(10) 0.0196(3) Uani 1 1 d . . . . .
H22 H 0.1172 0.9312 -0.0241 0.024 Uiso 1 1 calc R U . . .
C23 C 0.18951(9) 1.02377(14) -0.08780(10) 0.0202(3) Uani 1 1 d . . . . .
H23 H 0.1644 1.1047 -0.0869 0.024 Uiso 1 1 calc R U . . .
C24 C 0.25588(9) 1.01056(13) -0.12772(9) 0.0173(3) Uani 1 1 d . . . . .
C25 C 0.28786(9) 0.88578(13) -0.12701(9) 0.0186(3) Uani 1 1 d . . . . .
H25 H 0.3318 0.8697 -0.1537 0.022 Uiso 1 1 calc R U . . .
C26 C 0.25541(9) 0.78825(13) -0.08783(9) 0.0191(3) Uani 1 1 d . . . . .
H26 H 0.2784 0.7056 -0.0883 0.023 Uiso 1 1 calc R U . . .
C27 C 0.25586(10) 1.23904(14) -0.15675(11) 0.0272(3) Uani 1 1 d . . . . .
H27A H 0.1977 1.2425 -0.1878 0.041 Uiso 1 1 calc R U . . .
H27B H 0.2857 1.3001 -0.1851 0.041 Uiso 1 1 calc R U . . .
H27C H 0.2636 1.2610 -0.0924 0.041 Uiso 1 1 calc R U . . .
C28 C 0.36141(10) 1.09751(14) -0.19338(10) 0.0240(3) Uani 1 1 d . . . . .
H28A H 0.4075 1.0853 -0.1401 0.036 Uiso 1 1 calc R U . . .
H28B H 0.3702 1.1748 -0.2260 0.036 Uiso 1 1 calc R U . . .
H28C H 0.3569 1.0234 -0.2338 0.036 Uiso 1 1 calc R U . . .
N1 N 0.24618(7) 0.35266(11) 0.09096(7) 0.0146(2) Uani 1 1 d . . . . .
N2 N 0.18318(7) 0.41515(11) 0.10071(8) 0.0151(2) Uani 1 1 d . . . . .
N3 N 0.33375(7) 0.53713(11) 0.09498(7) 0.0140(2) Uani 1 1 d . . . . .
N4 N 0.27922(7) 0.62239(10) 0.10519(8) 0.0138(2) Uani 1 1 d . . . . .
N5 N 0.19306(7) 0.80113(11) -0.04859(8) 0.0178(2) Uani 1 1 d . . . . .
N6 N 0.28651(8) 1.11084(11) -0.16406(9) 0.0217(3) Uani 1 1 d . . . . .
In1 In 0.15040(2) 0.61438(2) 0.01433(2) 0.01442(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N3 1.3390(17) . ?
C1 N1 1.3556(17) . ?
C1 C2 1.4820(18) . ?
C2 C7 1.3941(19) . ?
C2 C3 1.4008(19) . ?
C3 C4 1.387(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.387(2) . ?
C8 C9 1.398(2) . ?
C8 N2 1.4257(17) . ?
C9 C10 1.386(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.3961(19) . ?
C14 C15 1.4013(19) . ?
C14 N4 1.4223(17) . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 In1 2.1528(14) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 In1 2.1552(14) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 N5 1.3431(18) . ?
C22 C23 1.370(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.415(2) . ?
C23 H23 0.9500 . ?
C24 N6 1.3501(18) . ?
C24 C25 1.4128(19) . ?
C25 C26 1.366(2) . ?
C25 H25 0.9500 . ?
C26 N5 1.3469(18) . ?
C26 H26 0.9500 . ?
C27 N6 1.4533(19) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 N6 1.456(2) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N1 N2 1.2931(16) . ?
N2 In1 2.4509(11) . ?
N3 N4 1.3224(15) . ?
N4 In1 2.2683(11) . ?
N5 In1 2.3688(12) . ?

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
N3 C1 N1 128.47(12) . . ?
N3 C1 C2 115.58(12) . . ?
N1 C1 C2 113.80(11) . . ?
C7 C2 C3 118.61(12) . . ?
C7 C2 C1 120.76(12) . . ?
C3 C2 C1 120.62(12) . . ?
C4 C3 C2 120.42(13) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 120.35(13) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.72(13) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 120.05(14) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 120.83(13) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
C13 C8 C9 119.73(13) . . ?
C13 C8 N2 117.66(13) . . ?
C9 C8 N2 122.61(13) . . ?
C10 C9 C8 119.65(14) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 120.55(15) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 119.71(14) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.41(15) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 119.94(14) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C19 C14 C15 118.77(13) . . ?
C19 C14 N4 117.94(12) . . ?
C15 C14 N4 123.17(12) . . ?
C16 C15 C14 120.09(13) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.76(14) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 119.32(14) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.48(14) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.57(13) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
In1 C20 H20A 109.5 . . ?
In1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
In1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
In1 C21 H21A 109.5 . . ?
In1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
In1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C22 C23 124.56(13) . . ?
N5 C22 H22 117.7 . . ?
C23 C22 H22 117.7 . . ?
C22 C23 C24 119.68(13) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
N6 C24 C25 122.31(13) . . ?
N6 C24 C23 122.05(13) . . ?
C25 C24 C23 115.64(13) . . ?
C26 C25 C24 119.81(13) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
N5 C26 C25 124.57(13) . . ?
N5 C26 H26 117.7 . . ?
C25 C26 H26 117.7 . . ?
N6 C27 H27A 109.5 . . ?
N6 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N6 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N6 C28 H28A 109.5 . . ?
N6 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N6 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N2 N1 C1 120.47(11) . . ?
N1 N2 C8 111.18(11) . . ?
N1 N2 In1 116.73(8) . . ?
C8 N2 In1 127.34(8) . . ?
N4 N3 C1 119.90(11) . . ?
N3 N4 C14 112.67(11) . . ?
N3 N4 In1 119.82(8) . . ?
C14 N4 In1 125.08(8) . . ?
C22 N5 C26 115.72(12) . . ?
C22 N5 In1 127.44(9) . . ?
C26 N5 In1 116.84(9) . . ?
C24 N6 C27 120.25(13) . . ?
C24 N6 C28 120.50(12) . . ?
C27 N6 C28 117.96(12) . . ?
C20 In1 C21 137.73(6) . . ?
C20 In1 N4 107.33(5) . . ?
C21 In1 N4 114.43(5) . . ?
C20 In1 N5 91.39(5) . . ?
C21 In1 N5 100.00(5) . . ?
N4 In1 N5 82.50(4) . . ?
C20 In1 N2 86.73(5) . . ?
C21 In1 N2 101.33(5) . . ?
N4 In1 N2 69.75(4) . . ?
N5 In1 N2 150.14(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C1 C2 C7 -35.74(18) . . . . ?
N1 C1 C2 C7 159.48(12) . . . . ?
N3 C1 C2 C3 143.29(13) . . . . ?
N1 C1 C2 C3 -21.50(18) . . . . ?
C7 C2 C3 C4 1.1(2) . . . . ?
C1 C2 C3 C4 -177.93(13) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 C7 1.0(2) . . . . ?
C5 C6 C7 C2 -0.9(2) . . . . ?
C3 C2 C7 C6 -0.1(2) . . . . ?
C1 C2 C7 C6 178.93(13) . . . . ?
C13 C8 C9 C10 -0.4(2) . . . . ?
N2 C8 C9 C10 179.00(13) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C9 C10 C11 C12 0.7(2) . . . . ?
C10 C11 C12 C13 0.4(2) . . . . ?
C9 C8 C13 C12 1.5(2) . . . . ?
N2 C8 C13 C12 -177.92(13) . . . . ?
C11 C12 C13 C8 -1.5(2) . . . . ?
C19 C14 C15 C16 -0.7(2) . . . . ?
N4 C14 C15 C16 -176.62(12) . . . . ?
C14 C15 C16 C17 0.3(2) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C17 C18 C19 C14 -0.2(2) . . . . ?
C15 C14 C19 C18 0.7(2) . . . . ?
N4 C14 C19 C18 176.82(12) . . . . ?
N5 C22 C23 C24 -0.1(2) . . . . ?
C22 C23 C24 N6 -178.86(13) . . . . ?
C22 C23 C24 C25 1.1(2) . . . . ?
N6 C24 C25 C26 178.82(13) . . . . ?
C23 C24 C25 C26 -1.2(2) . . . . ?
C24 C25 C26 N5 0.2(2) . . . . ?
N3 C1 N1 N2 22.4(2) . . . . ?
C2 C1 N1 N2 -175.25(11) . . . . ?
C1 N1 N2 C8 -170.18(11) . . . . ?
C1 N1 N2 In1 32.39(15) . . . . ?
C13 C8 N2 N1 154.64(12) . . . . ?
C9 C8 N2 N1 -24.78(18) . . . . ?
C13 C8 N2 In1 -50.90(16) . . . . ?
C9 C8 N2 In1 129.68(12) . . . . ?
N1 C1 N3 N4 -22.4(2) . . . . ?
C2 C1 N3 N4 175.43(11) . . . . ?
C1 N3 N4 C14 158.78(11) . . . . ?
C1 N3 N4 In1 -38.03(15) . . . . ?
C19 C14 N4 N3 178.18(11) . . . . ?
C15 C14 N4 N3 -5.84(18) . . . . ?
C19 C14 N4 In1 16.03(16) . . . . ?
C15 C14 N4 In1 -167.99(10) . . . . ?
C23 C22 N5 C26 -0.8(2) . . . . ?
C23 C22 N5 In1 179.76(11) . . . . ?
C25 C26 N5 C22 0.8(2) . . . . ?
C25 C26 N5 In1 -179.73(11) . . . . ?
C25 C24 N6 C27 -175.10(13) . . . . ?
C23 C24 N6 C27 4.9(2) . . . . ?
C25 C24 N6 C28 -8.3(2) . . . . ?
C23 C24 N6 C28 171.68(13) . . . . ?

_refine_diff_density_max         0.604
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.057

_shelxl_version_number           2014-3

