# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_ddauer_1

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 N2 O2'
_chemical_formula_sum            'C15 H10 N2 O2'
_chemical_formula_weight         250.25

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'

_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                   9.0660(10)
_cell_length_b                   9.4570(10)
_cell_length_c                   14.172(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.230(10)
_cell_angle_gamma                90
_cell_volume                     1177.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6088
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      29.65

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6934
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS-2008/2

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'INCOATEC Mo Microsource'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Bruker Smart Apex II Quazar'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18686
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.318
_diffrn_reflns_theta_max         29.687
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3321
_reflns_number_gt                2852
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0453P)²+0.4674P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3321
_refine_ls_number_parameters     245
_refine_ls_number_restraints     422
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.016
_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 0.38674(12) 0.85900(12) 0.55212(8) 0.0211(2) Uani 1 1 d D . . . .
H1A H 0.3525 0.8030 0.6018 0.025 Uiso 1 1 calc R U . . .
H1B H 0.4548 0.9348 0.5861 0.025 Uiso 1 1 calc R U . . .
C9 C 0.25249(12) 0.92349(12) 0.48391(8) 0.0215(2) Uani 1 1 d D U . . .
O2 O 0.1218(4) 0.8450(5) 0.4552(4) 0.0184(6) Uani 0.797(10) 1 d D U P A 1
N2 N 0.2497(6) 1.0476(7) 0.4468(7) 0.0216(7) Uani 0.797(10) 1 d D U P A 1
C10 C 0.0235(5) 0.9347(6) 0.3916(5) 0.0176(6) Uani 0.797(10) 1 d D U P A 1
C11 C -0.1252(6) 0.9087(6) 0.3409(4) 0.0226(7) Uani 0.797(10) 1 d D U P A 1
H11 H -0.1754 0.8222 0.3471 0.027 Uiso 0.797(10) 1 calc R U P A 1
C12 C -0.1964(5) 1.0177(5) 0.2802(3) 0.0235(7) Uani 0.797(10) 1 d D U P A 1
H12 H -0.2983 1.0059 0.2433 0.028 Uiso 0.797(10) 1 calc R U P A 1
C13 C -0.1197(5) 1.1444(4) 0.2730(3) 0.0238(7) Uani 0.797(10) 1 d D U P A 1
H13 H -0.1708 1.2161 0.2303 0.029 Uiso 0.797(10) 1 calc R U P A 1
C14 C 0.0289(5) 1.1687(4) 0.3263(4) 0.0221(6) Uani 0.797(10) 1 d D U P A 1
H14 H 0.0789 1.2559 0.3219 0.027 Uiso 0.797(10) 1 calc R U P A 1
C15 C 0.1010(5) 1.0602(4) 0.3862(4) 0.0165(5) Uani 0.797(10) 1 d D U P A 1
O2' O 0.235(2) 1.050(2) 0.440(2) 0.0190(18) Uani 0.203(10) 1 d D U P A 2
N2' N 0.132(2) 0.842(2) 0.468(2) 0.0185(18) Uani 0.203(10) 1 d D U P A 2
C10' C 0.087(2) 1.0434(19) 0.3826(18) 0.0181(17) Uani 0.203(10) 1 d D U P A 2
C11' C 0.010(2) 1.1494(18) 0.3185(17) 0.0220(19) Uani 0.203(10) 1 d D U P A 2
H11' H 0.0570 1.2353 0.3069 0.026 Uiso 0.203(10) 1 calc R U P A 2
C12' C -0.1398(18) 1.1166(17) 0.2744(14) 0.0200(18) Uani 0.203(10) 1 d D U P A
2
H12' H -0.2015 1.1829 0.2320 0.024 Uiso 0.203(10) 1 calc R U P A 2
C13' C -0.199(2) 0.9887(17) 0.2916(14) 0.0194(18) Uani 0.203(10) 1 d D U P A 2
H13' H -0.3013 0.9690 0.2572 0.023 Uiso 0.203(10) 1 calc R U P A 2
C14' C -0.126(2) 0.888(2) 0.3534(17) 0.0170(18) Uani 0.203(10) 1 d D U P A 2
H14' H -0.1731 0.8024 0.3640 0.020 Uiso 0.203(10) 1 calc R U P A 2
C15' C 0.025(2) 0.919(2) 0.4008(19) 0.0137(15) Uani 0.203(10) 1 d D U P A 2
C2 C 0.47259(12) 0.76569(11) 0.49953(8) 0.0189(2) Uani 1 1 d D . . . .
O1 O 0.57856(9) 0.67805(8) 0.55649(5) 0.01991(17) Uani 1 1 d D . . . .
N1 N 0.46113(10) 0.76135(10) 0.40711(7) 0.02011(19) Uani 1 1 d D . . . .
C3 C 0.64439(12) 0.61181(11) 0.49005(8) 0.0184(2) Uani 1 1 d D . . . .
C4 C 0.76086(13) 0.51346(12) 0.50729(9) 0.0229(2) Uani 1 1 d D . . . .
H4 H 0.8089 0.4815 0.5710 0.027 Uiso 1 1 calc R U . . .
C5 C 0.80297(14) 0.46435(12) 0.42508(9) 0.0251(2) Uani 1 1 d D . . . .
H5 H 0.8829 0.3971 0.4327 0.030 Uiso 1 1 calc R U . . .
C6 C 0.73051(14) 0.51157(13) 0.33125(9) 0.0259(2) Uani 1 1 d D . . . .
H6 H 0.7614 0.4744 0.2768 0.031 Uiso 1 1 calc R U . . .
C7 C 0.61445(13) 0.61157(13) 0.31613(8) 0.0242(2) Uani 1 1 d D . . . .
H7 H 0.5665 0.6444 0.2526 0.029 Uiso 1 1 calc R U . . .
C8 C 0.57162(12) 0.66153(11) 0.39776(8) 0.0193(2) Uani 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C9 1.4864(15) . ?
C1 C2 1.4917(15) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C9 N2 1.284(5) . ?
C9 N2' 1.309(15) . ?
C9 O2' 1.335(13) . ?
C9 O2 1.372(3) . ?
O2 C10 1.390(3) . ?
N2 C15 1.414(4) . ?
C10 C11 1.385(4) . ?
C10 C15 1.391(3) . ?
C11 C12 1.396(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.402(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(4) . ?
C14 H14 0.9500 . ?
O2' C10' 1.393(13) . ?
N2' C15' 1.385(14) . ?
C10' C15' 1.353(12) . ?
C10' C11' 1.416(14) . ?
C11' C12' 1.384(13) . ?
C11' H11' 0.9500 . ?
C12' C13' 1.371(10) . ?
C12' H12' 0.9500 . ?
C13' C14' 1.352(12) . ?
C13' H13' 0.9500 . ?
C14' C15' 1.396(14) . ?
C14' H14' 0.9500 . ?
C2 N1 1.2888(14) . ?
C2 O1 1.3712(13) . ?
O1 C3 1.3826(13) . ?
N1 C8 1.4062(14) . ?
C3 C4 1.3831(15) . ?
C3 C8 1.3938(15) . ?
C4 C5 1.3920(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.4035(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.3916(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3904(16) . ?
C7 H7 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C1 C2 111.23(9) . . ?
C9 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
C9 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
N2' C9 O2' 116.5(10) . . ?
N2 C9 O2 116.4(3) . . ?
N2 C9 C1 124.9(2) . . ?
N2' C9 C1 112.9(8) . . ?
O2' C9 C1 130.6(7) . . ?
O2 C9 C1 118.69(18) . . ?
C9 O2 C10 103.4(3) . . ?
C9 N2 C15 104.2(4) . . ?
C11 C10 O2 127.9(3) . . ?
C11 C10 C15 124.4(3) . . ?
O2 C10 C15 107.7(3) . . ?
C10 C11 C12 115.6(3) . . ?
C10 C11 H11 122.2 . . ?
C12 C11 H11 122.2 . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 122.2(3) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C15 C14 C13 117.2(3) . . ?
C15 C14 H14 121.4 . . ?
C13 C14 H14 121.4 . . ?
C14 C15 C10 119.7(3) . . ?
C14 C15 N2 132.0(3) . . ?
C10 C15 N2 108.3(3) . . ?
C9 O2' C10' 102.7(11) . . ?
C9 N2' C15' 103.1(13) . . ?
C15' C10' O2' 108.1(13) . . ?
C15' C10' C11' 125.0(13) . . ?
O2' C10' C11' 126.8(12) . . ?
C12' C11' C10' 113.9(12) . . ?
C12' C11' H11' 123.1 . . ?
C10' C11' H11' 123.1 . . ?
C13' C12' C11' 120.3(13) . . ?
C13' C12' H12' 119.9 . . ?
C11' C12' H12' 119.9 . . ?
C14' C13' C12' 125.4(13) . . ?
C14' C13' H13' 117.3 . . ?
C12' C13' H13' 117.3 . . ?
C13' C14' C15' 115.8(13) . . ?
C13' C14' H14' 122.1 . . ?
C15' C14' H14' 122.1 . . ?
C10' C15' N2' 109.4(13) . . ?
C10' C15' C14' 119.5(13) . . ?
N2' C15' C14' 131.1(13) . . ?
N1 C2 O1 116.67(10) . . ?
N1 C2 C1 127.22(10) . . ?
O1 C2 C1 116.07(9) . . ?
C2 O1 C3 103.31(8) . . ?
C2 N1 C8 103.63(9) . . ?
O1 C3 C4 128.54(10) . . ?
O1 C3 C8 107.59(9) . . ?
C4 C3 C8 123.87(10) . . ?
C3 C4 C5 115.53(11) . . ?
C3 C4 H4 122.2 . . ?
C5 C4 H4 122.2 . . ?
C4 C5 C6 121.74(11) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C5 121.48(11) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C8 C7 C6 117.26(11) . . ?
C8 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
C7 C8 C3 120.10(10) . . ?
C7 C8 N1 131.11(10) . . ?
C3 C8 N1 108.78(9) . . ?

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
C2 C1 C9 N2 -96.7(7) . . . . ?
C2 C1 C9 N2' 86.1(17) . . . . ?
C2 C1 C9 O2' -96(2) . . . . ?
C2 C1 C9 O2 81.3(4) . . . . ?
N2 C9 O2 C10 -0.6(8) . . . . ?
N2' C9 O2 C10 144(14) . . . . ?
O2' C9 O2 C10 -0.8(17) . . . . ?
C1 C9 O2 C10 -178.8(4) . . . . ?
N2' C9 N2 C15 -4(2) . . . . ?
O2' C9 N2 C15 2(20) . . . . ?
O2 C9 N2 C15 0.9(10) . . . . ?
C1 C9 N2 C15 178.9(4) . . . . ?
C9 O2 C10 C11 179.9(7) . . . . ?
C9 O2 C10 C15 0.1(7) . . . . ?
O2 C10 C11 C12 -178.7(7) . . . . ?
C15 C10 C11 C12 1.1(10) . . . . ?
C10 C11 C12 C13 -0.4(8) . . . . ?
C11 C12 C13 C14 -0.9(7) . . . . ?
C12 C13 C14 C15 1.5(8) . . . . ?
C13 C14 C15 C10 -0.8(9) . . . . ?
C13 C14 C15 N2 177.9(8) . . . . ?
C11 C10 C15 C14 -0.5(11) . . . . ?
O2 C10 C15 C14 179.3(6) . . . . ?
C11 C10 C15 N2 -179.5(8) . . . . ?
O2 C10 C15 N2 0.4(9) . . . . ?
C9 N2 C15 C14 -179.5(7) . . . . ?
C9 N2 C15 C10 -0.7(10) . . . . ?
N2 C9 O2' C10' -179(100) . . . . ?
N2' C9 O2' C10' -5(3) . . . . ?
O2 C9 O2' C10' 0(3) . . . . ?
C1 C9 O2' C10' 177.3(14) . . . . ?
N2 C9 N2' C15' 5(3) . . . . ?
O2' C9 N2' C15' 4(3) . . . . ?
O2 C9 N2' C15' -33(12) . . . . ?
C1 C9 N2' C15' -177.7(18) . . . . ?
C9 O2' C10' C15' 4(3) . . . . ?
C9 O2' C10' C11' -179(3) . . . . ?
C15' C10' C11' C12' 1(4) . . . . ?
O2' C10' C11' C12' -177(3) . . . . ?
C10' C11' C12' C13' -2(3) . . . . ?
C11' C12' C13' C14' 3(3) . . . . ?
C12' C13' C14' C15' -2(3) . . . . ?
O2' C10' C15' N2' -1(4) . . . . ?
C11' C10' C15' N2' -179(3) . . . . ?
O2' C10' C15' C14' 178(3) . . . . ?
C11' C10' C15' C14' 1(5) . . . . ?
C9 N2' C15' C10' -1(3) . . . . ?
C9 N2' C15' C14' 179(3) . . . . ?
C13' C14' C15' C10' 0(4) . . . . ?
C13' C14' C15' N2' 180(3) . . . . ?
C9 C1 C2 N1 15.40(16) . . . . ?
C9 C1 C2 O1 -166.73(9) . . . . ?
N1 C2 O1 C3 1.31(12) . . . . ?
C1 C2 O1 C3 -176.80(9) . . . . ?
O1 C2 N1 C8 -0.73(12) . . . . ?
C1 C2 N1 C8 177.13(10) . . . . ?
C2 O1 C3 C4 178.83(11) . . . . ?
C2 O1 C3 C8 -1.28(11) . . . . ?
O1 C3 C4 C5 179.62(10) . . . . ?
C8 C3 C4 C5 -0.26(17) . . . . ?
C3 C4 C5 C6 -0.42(17) . . . . ?
C4 C5 C6 C7 1.00(18) . . . . ?
C5 C6 C7 C8 -0.85(17) . . . . ?
C6 C7 C8 C3 0.19(16) . . . . ?
C6 C7 C8 N1 179.60(11) . . . . ?
O1 C3 C8 C7 -179.53(9) . . . . ?
C4 C3 C8 C7 0.38(17) . . . . ?
O1 C3 C8 N1 0.94(12) . . . . ?
C4 C3 C8 N1 -179.16(10) . . . . ?
C2 N1 C8 C7 -179.62(12) . . . . ?
C2 N1 C8 C3 -0.16(12) . . . . ?

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-2



_database_code_depnum_ccdc_archive 'CCDC 995110'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ddauer_2

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 N2 S2'
_chemical_formula_sum            'C15 H10 N2 S2'
_chemical_formula_weight         282.37

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   25.412(3)
_cell_length_b                   4.5360(10)
_cell_length_c                   11.165(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.76(2)
_cell_angle_gamma                90
_cell_volume                     1255.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9992
_cell_measurement_theta_min      3.288
_cell_measurement_theta_max      30.509

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.409
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7084
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS-2008/2

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'INCOATEC Mo Microsource'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Bruker Smart Apex II Quazar'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24628
_diffrn_reflns_av_unetI/netI     0.0082
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.643
_diffrn_reflns_theta_max         27.097
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1379
_reflns_number_gt                1347
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0267P)²+1.6801P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1379
_refine_ls_number_parameters     87
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0245
_refine_ls_wR_factor_ref         0.0634
_refine_ls_wR_factor_gt          0.0631
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_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
S1 S 0.44222(2) 0.56950(7) 0.38774(3) 0.01586(11) Uani 1 1 d . . . . .
N1 N 0.41694(4) 0.6464(2) 0.15093(9) 0.0160(2) Uani 1 1 d . . . . .
C1 C 0.5000 0.9141(4) 0.2500 0.0182(3) Uani 1 2 d S T P . .
H00A H 0.5071 1.0420 0.3237 0.022 Uiso 0.5 1 calc R U P . .
H00B H 0.4929 1.0420 0.1763 0.022 Uiso 0.5 1 calc R U P . .
C2 C 0.45142(5) 0.7221(3) 0.24988(11) 0.0151(2) Uani 1 1 d . . . . .
C8 C 0.37928(5) 0.4506(3) 0.17975(11) 0.0146(2) Uani 1 1 d . . . . .
C3 C 0.38651(5) 0.3809(3) 0.30514(10) 0.0142(2) Uani 1 1 d . . . . .
C4 C 0.35266(5) 0.1831(3) 0.34771(11) 0.0174(2) Uani 1 1 d . . . . .
H4 H 0.3580 0.1371 0.4326 0.021 Uiso 1 1 calc R U . . .
C5 C 0.31100(5) 0.0561(3) 0.26201(12) 0.0191(3) Uani 1 1 d . . . . .
H5 H 0.2874 -0.0792 0.2885 0.023 Uiso 1 1 calc R U . . .
C7 C 0.33669(5) 0.3204(3) 0.09483(11) 0.0178(3) Uani 1 1 d . . . . .
H7 H 0.3310 0.3661 0.0099 0.021 Uiso 1 1 calc R U . . .
C6 C 0.30318(5) 0.1244(3) 0.13672(12) 0.0195(3) Uani 1 1 d . . . . .
H00C H 0.2743 0.0344 0.0797 0.023 Uiso 1 1 calc R 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
S1 C3 1.7349(12) . ?
S1 C2 1.7498(12) . ?
N1 C2 1.2955(16) . ?
N1 C8 1.3943(16) . ?
C1 C2 1.5106(15) . ?
C1 C2 1.5106(15) 2_655 ?
C1 H00A 0.9900 . ?
C1 H00B 0.9900 . ?
C8 C7 1.4022(17) . ?
C8 C3 1.4072(16) . ?
C3 C4 1.3970(17) . ?
C4 C5 1.3859(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.4034(18) . ?
C5 H5 0.9500 . ?
C7 C6 1.3821(18) . ?
C7 H7 0.9500 . ?
C6 H00C 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C2 88.82(6) . . ?
C2 N1 C8 109.96(10) . . ?
C2 C1 C2 109.59(14) . 2_655 ?
C2 C1 H00A 109.8 . . ?
C2 C1 H00A 109.8 2_655 . ?
C2 C1 H00B 109.8 . . ?
C2 C1 H00B 109.8 2_655 . ?
H00A C1 H00B 108.2 . . ?
N1 C2 C1 123.51(10) . . ?
N1 C2 S1 116.67(9) . . ?
C1 C2 S1 119.68(7) . . ?
N1 C8 C7 125.38(11) . . ?
N1 C8 C3 115.30(10) . . ?
C7 C8 C3 119.31(11) . . ?
C4 C3 C8 121.87(11) . . ?
C4 C3 S1 128.86(9) . . ?
C8 C3 S1 109.26(9) . . ?
C5 C4 C3 117.77(11) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C4 C5 C6 120.98(12) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C6 C7 C8 118.92(11) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C7 C6 C5 121.14(11) . . ?
C7 C6 H00C 119.4 . . ?
C5 C6 H00C 119.4 . . ?

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
C8 N1 C2 C1 175.28(11) . . . . ?
C8 N1 C2 S1 -0.42(13) . . . . ?
C2 C1 C2 N1 -94.49(12) 2_655 . . . ?
C2 C1 C2 S1 81.08(8) 2_655 . . . ?
C3 S1 C2 N1 0.46(10) . . . . ?
C3 S1 C2 C1 -175.41(10) . . . . ?
C2 N1 C8 C7 -178.97(11) . . . . ?
C2 N1 C8 C3 0.14(15) . . . . ?
N1 C8 C3 C4 -178.61(10) . . . . ?
C7 C8 C3 C4 0.55(18) . . . . ?
N1 C8 C3 S1 0.20(13) . . . . ?
C7 C8 C3 S1 179.36(9) . . . . ?
C2 S1 C3 C4 178.36(12) . . . . ?
C2 S1 C3 C8 -0.34(9) . . . . ?
C8 C3 C4 C5 -0.25(18) . . . . ?
S1 C3 C4 C5 -178.80(10) . . . . ?
C3 C4 C5 C6 0.00(18) . . . . ?
N1 C8 C7 C6 178.48(11) . . . . ?
C3 C8 C7 C6 -0.59(18) . . . . ?
C8 C7 C6 C5 0.35(19) . . . . ?
C4 C5 C6 C7 -0.05(19) . . . . ?

_refine_diff_density_max         0.343
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-2



_database_code_depnum_ccdc_archive 'CCDC 995111'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ddauer_3

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 Al N2 O2'
_chemical_formula_sum            'C17 H15 Al N2 O2'
_chemical_formula_weight         306.29

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

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.998(2)
_cell_length_b                   8.336(2)
_cell_length_c                   13.294(3)
_cell_angle_alpha                93.54(2)
_cell_angle_beta                 103.31(2)
_cell_angle_gamma                117.86(3)
_cell_volume                     747.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3877
_cell_measurement_theta_min      2.819
_cell_measurement_theta_max      25.31

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8155
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_process_details   SADABS-2008/2

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Mo rotating-anode'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Bruker SMART APEXII Ultra'
_diffrn_measurement_method       omega-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12679
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.605
_diffrn_reflns_theta_max         25.415
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2745
_reflns_number_gt                2094
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0610P)²+0.3249P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2745
_refine_ls_number_parameters     201
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.021
_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 0.6677(3) 0.3520(3) 0.13834(17) 0.0232(5) Uani 1 1 d D . . . .
H1 H 0.7128 0.4603 0.1089 0.028 Uiso 1 1 calc R U . . .
Al1 Al 0.47875(10) -0.00349(9) 0.25929(5) 0.0214(2) Uani 1 1 d D . . . .
C2 C 0.4882(3) 0.1974(3) 0.08728(17) 0.0216(5) Uani 1 1 d D . . . .
O1 O 0.3848(2) 0.1911(2) -0.01183(11) 0.0232(4) Uani 1 1 d D . . . .
C3 C 0.2157(3) 0.0176(3) -0.04206(17) 0.0215(5) Uani 1 1 d D . . . .
C4 C 0.0647(3) -0.0541(3) -0.13443(17) 0.0243(5) Uani 1 1 d D . . . .
H4 H 0.0656 0.0130 -0.1897 0.029 Uiso 1 1 calc R U . . .
C5 C -0.0896(3) -0.2305(3) -0.14234(18) 0.0259(6) Uani 1 1 d D . . . .
H5 H -0.1977 -0.2869 -0.2050 0.031 Uiso 1 1 calc R U . . .
C6 C -0.0895(3) -0.3269(3) -0.06034(18) 0.0255(5) Uani 1 1 d D . . . .
H6 H -0.1982 -0.4471 -0.0681 0.031 Uiso 1 1 calc R U . . .
C7 C 0.0664(3) -0.2510(3) 0.03269(18) 0.0233(5) Uani 1 1 d D . . . .
H7 H 0.0667 -0.3167 0.0886 0.028 Uiso 1 1 calc R U . . .
C8 C 0.2203(3) -0.0763(3) 0.03981(17) 0.0201(5) Uani 1 1 d D . . . .
N1 N 0.3942(3) 0.0391(3) 0.12143(14) 0.0203(4) Uani 1 1 d D . . . .
C9 C 0.7817(3) 0.3484(3) 0.23280(17) 0.0217(5) Uani 1 1 d D . . . .
O2 O 0.9690(2) 0.4928(2) 0.27858(11) 0.0230(4) Uani 1 1 d D . . . .
C10 C 1.0464(3) 0.4423(3) 0.36826(17) 0.0220(5) Uani 1 1 d D . . . .
C11 C 1.2290(3) 0.5410(3) 0.44089(18) 0.0251(5) Uani 1 1 d D . . . .
H11 H 1.3252 0.6595 0.4348 0.030 Uiso 1 1 calc R U . . .
C12 C 1.2652(3) 0.4575(3) 0.52405(18) 0.0274(6) Uani 1 1 d D . . . .
H12 H 1.3902 0.5196 0.5763 0.033 Uiso 1 1 calc R U . . .
C13 C 1.1221(3) 0.2848(3) 0.53234(18) 0.0251(5) Uani 1 1 d D . . . .
H13 H 1.1510 0.2326 0.5909 0.030 Uiso 1 1 calc R U . . .
C14 C 0.9381(3) 0.1867(3) 0.45738(17) 0.0228(5) Uani 1 1 d D . . . .
H14 H 0.8410 0.0681 0.4628 0.027 Uiso 1 1 calc R U . . .
C15 C 0.9029(3) 0.2698(3) 0.37453(17) 0.0210(5) Uani 1 1 d D . . . .
N2 N 0.7341(3) 0.2127(3) 0.28859(14) 0.0210(4) Uani 1 1 d D . . . .
C16 C 0.3309(3) 0.0260(3) 0.35089(18) 0.0268(6) Uani 1 1 d D . . . .
H16A H 0.3223 0.1383 0.3435 0.040 Uiso 1 1 calc R U . . .
H16B H 0.3991 0.0360 0.4244 0.040 Uiso 1 1 calc R U . . .
H16C H 0.1974 -0.0817 0.3307 0.040 Uiso 1 1 calc R U . . .
C17 C 0.4928(3) -0.2311(3) 0.25317(18) 0.0267(6) Uani 1 1 d D . . . .
H17A H 0.3587 -0.3379 0.2329 0.040 Uiso 1 1 calc R U . . .
H17B H 0.5673 -0.2325 0.3226 0.040 Uiso 1 1 calc R U . . .
H17C H 0.5595 -0.2374 0.2010 0.040 Uiso 1 1 calc R 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 C2 1.377(3) . ?
C1 C9 1.383(3) . ?
C1 H1 0.9500 . ?
Al1 N1 1.9171(19) . ?
Al1 N2 1.918(2) . ?
Al1 C17 1.951(2) . ?
Al1 C16 1.959(2) . ?
C2 N1 1.348(3) . ?
C2 O1 1.368(3) . ?
O1 C3 1.390(3) . ?
C3 C4 1.369(3) . ?
C3 C8 1.383(3) . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(3) . ?
C7 H7 0.9500 . ?
C8 N1 1.401(3) . ?
C9 N2 1.344(3) . ?
C9 O2 1.367(3) . ?
O2 C10 1.395(3) . ?
C10 C11 1.368(3) . ?
C10 C15 1.382(3) . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 N2 1.406(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 119.5(2) . . ?
C2 C1 H1 120.3 . . ?
C9 C1 H1 120.3 . . ?
N1 Al1 N2 91.67(9) . . ?
N1 Al1 C17 111.92(10) . . ?
N2 Al1 C17 112.35(10) . . ?
N1 Al1 C16 111.56(10) . . ?
N2 Al1 C16 110.97(10) . . ?
C17 Al1 C16 115.89(11) . . ?
N1 C2 O1 111.75(19) . . ?
N1 C2 C1 128.2(2) . . ?
O1 C2 C1 120.1(2) . . ?
C2 O1 C3 106.06(17) . . ?
C4 C3 C8 123.7(2) . . ?
C4 C3 O1 128.3(2) . . ?
C8 C3 O1 108.03(19) . . ?
C3 C4 C5 115.9(2) . . ?
C3 C4 H4 122.0 . . ?
C5 C4 H4 122.0 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 121.5(2) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C8 C7 C6 116.9(2) . . ?
C8 C7 H7 121.6 . . ?
C6 C7 H7 121.6 . . ?
C7 C8 C3 120.6(2) . . ?
C7 C8 N1 131.3(2) . . ?
C3 C8 N1 108.09(19) . . ?
C2 N1 C8 106.07(18) . . ?
C2 N1 Al1 125.22(15) . . ?
C8 N1 Al1 128.54(15) . . ?
N2 C9 O2 112.05(19) . . ?
N2 C9 C1 127.8(2) . . ?
O2 C9 C1 120.1(2) . . ?
C9 O2 C10 105.89(17) . . ?
C11 C10 C15 123.6(2) . . ?
C11 C10 O2 128.4(2) . . ?
C15 C10 O2 108.01(19) . . ?
C10 C11 C12 116.0(2) . . ?
C10 C11 H11 122.0 . . ?
C12 C11 H11 122.0 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 121.8(2) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C15 C14 C13 116.7(2) . . ?
C15 C14 H14 121.6 . . ?
C13 C14 H14 121.6 . . ?
C14 C15 C10 120.6(2) . . ?
C14 C15 N2 131.4(2) . . ?
C10 C15 N2 108.01(19) . . ?
C9 N2 C15 106.02(18) . . ?
C9 N2 Al1 125.50(15) . . ?
C15 N2 Al1 128.32(15) . . ?
Al1 C16 H16A 109.5 . . ?
Al1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Al1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Al1 C17 H17A 109.5 . . ?
Al1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Al1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C9 C1 C2 N1 6.2(4) . . . . ?
C9 C1 C2 O1 -172.3(2) . . . . ?
N1 C2 O1 C3 -0.3(2) . . . . ?
C1 C2 O1 C3 178.4(2) . . . . ?
C2 O1 C3 C4 179.3(2) . . . . ?
C2 O1 C3 C8 0.4(2) . . . . ?
C8 C3 C4 C5 0.5(3) . . . . ?
O1 C3 C4 C5 -178.3(2) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C7 -0.6(4) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C3 0.8(3) . . . . ?
C6 C7 C8 N1 178.6(2) . . . . ?
C4 C3 C8 C7 -1.1(4) . . . . ?
O1 C3 C8 C7 177.9(2) . . . . ?
C4 C3 C8 N1 -179.4(2) . . . . ?
O1 C3 C8 N1 -0.4(2) . . . . ?
O1 C2 N1 C8 0.1(2) . . . . ?
C1 C2 N1 C8 -178.5(2) . . . . ?
O1 C2 N1 Al1 -175.45(13) . . . . ?
C1 C2 N1 Al1 6.0(3) . . . . ?
C7 C8 N1 C2 -177.8(2) . . . . ?
C3 C8 N1 C2 0.2(2) . . . . ?
C7 C8 N1 Al1 -2.5(4) . . . . ?
C3 C8 N1 Al1 175.50(16) . . . . ?
C2 C1 C9 N2 -5.2(4) . . . . ?
C2 C1 C9 O2 172.8(2) . . . . ?
N2 C9 O2 C10 1.5(2) . . . . ?
C1 C9 O2 C10 -176.9(2) . . . . ?
C9 O2 C10 C11 -179.6(2) . . . . ?
C9 O2 C10 C15 -0.5(2) . . . . ?
C15 C10 C11 C12 -0.1(3) . . . . ?
O2 C10 C11 C12 178.9(2) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C14 1.0(4) . . . . ?
C12 C13 C14 C15 -0.7(3) . . . . ?
C13 C14 C15 C10 0.0(3) . . . . ?
C13 C14 C15 N2 -177.8(2) . . . . ?
C11 C10 C15 C14 0.4(4) . . . . ?
O2 C10 C15 C14 -178.74(19) . . . . ?
C11 C10 C15 N2 178.6(2) . . . . ?
O2 C10 C15 N2 -0.5(2) . . . . ?
O2 C9 N2 C15 -1.8(2) . . . . ?
C1 C9 N2 C15 176.4(2) . . . . ?
O2 C9 N2 Al1 174.03(14) . . . . ?
C1 C9 N2 Al1 -7.8(3) . . . . ?
C14 C15 N2 C9 179.3(2) . . . . ?
C10 C15 N2 C9 1.3(2) . . . . ?
C14 C15 N2 Al1 3.7(4) . . . . ?
C10 C15 N2 Al1 -174.27(16) . . . . ?

_refine_diff_density_max         0.412
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-2



_database_code_depnum_ccdc_archive 'CCDC 995112'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ddauer_4

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 Al N2 S2'
_chemical_formula_sum            'C17 H15 Al N2 S2'
_chemical_formula_weight         338.41

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'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1260(10)
_cell_length_b                   7.6960(10)
_cell_length_c                   14.730(2)
_cell_angle_alpha                90.500(10)
_cell_angle_beta                 93.120(10)
_cell_angle_gamma                93.44(2)
_cell_volume                     805.11(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3319
_cell_measurement_theta_min      2.652
_cell_measurement_theta_max      26.381

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.382
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.683677
_exptl_absorpt_correction_T_max  0.745381
_exptl_absorpt_process_details   TWINABS-2008/2

_exptl_special_details           twin


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Mo rotating-anode'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Bruker SMART APEXII Ultra'
_diffrn_measurement_method       omega-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34844
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.385
_diffrn_reflns_theta_max         26.471
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3313
_reflns_number_gt                2997
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component perfect twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0545P)²+0.1787P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3313
_refine_ls_number_parameters     201
_refine_ls_number_restraints     231
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0897
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_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 0.2295(2) -0.1921(2) 0.21667(10) 0.0174(3) Uani 1 1 d D U . . .
H1 H 0.2171 -0.3148 0.2080 0.021 Uiso 1 1 calc R U . . .
Al1 Al 0.25120(6) 0.23352(6) 0.24643(3) 0.01375(12) Uani 1 1 d D U . . .
C2 C 0.2358(2) -0.12639(19) 0.30512(10) 0.0167(3) Uani 1 1 d D U . . .
S1 S 0.22714(6) -0.26741(5) 0.39730(3) 0.01978(12) Uani 1 1 d D U . . .
C3 C 0.2416(2) -0.0916(2) 0.47281(11) 0.0189(3) Uani 1 1 d D U . . .
C4 C 0.2427(2) -0.0934(2) 0.56691(11) 0.0241(3) Uani 1 1 d D U . . .
H4 H 0.2355 -0.2002 0.5988 0.029 Uiso 1 1 calc R U . . .
C5 C 0.2547(2) 0.0648(2) 0.61341(11) 0.0261(4) Uani 1 1 d D U . . .
H5 H 0.2565 0.0665 0.6780 0.031 Uiso 1 1 calc R U . . .
C6 C 0.2642(2) 0.2209(2) 0.56645(11) 0.0245(4) Uani 1 1 d D U . . .
H6 H 0.2717 0.3280 0.5994 0.029 Uiso 1 1 calc R U . . .
C7 C 0.2627(2) 0.2225(2) 0.47241(11) 0.0205(3) Uani 1 1 d D U . . .
H7 H 0.2690 0.3296 0.4408 0.025 Uiso 1 1 calc R U . . .
C8 C 0.2518(2) 0.0644(2) 0.42501(10) 0.0168(3) Uani 1 1 d D U . . .
N1 N 0.24846(17) 0.04323(16) 0.33025(9) 0.0158(3) Uani 1 1 d D U . . .
C9 C 0.2404(2) -0.08799(19) 0.14035(10) 0.0157(3) Uani 1 1 d D U . . .
S2 S 0.23265(5) -0.18123(5) 0.03172(3) 0.01793(12) Uani 1 1 d D U . . .
C10 C 0.2529(2) 0.0239(2) -0.01661(10) 0.0166(3) Uani 1 1 d D U . . .
C11 C 0.2564(2) 0.0667(2) -0.10838(11) 0.0202(3) Uani 1 1 d D U . . .
H11 H 0.2491 -0.0213 -0.1543 0.024 Uiso 1 1 calc R U . . .
C12 C 0.2708(2) 0.2417(2) -0.13056(11) 0.0215(3) Uani 1 1 d D U . . .
H12 H 0.2722 0.2742 -0.1926 0.026 Uiso 1 1 calc R U . . .
C13 C 0.2832(2) 0.3702(2) -0.06321(11) 0.0201(3) Uani 1 1 d D U . . .
H13 H 0.2936 0.4891 -0.0800 0.024 Uiso 1 1 calc R U . . .
C14 C 0.2807(2) 0.3278(2) 0.02798(10) 0.0178(3) Uani 1 1 d D U . . .
H14 H 0.2898 0.4166 0.0735 0.021 Uiso 1 1 calc R U . . .
C15 C 0.2645(2) 0.15265(19) 0.05177(10) 0.0153(3) Uani 1 1 d D U . . .
N2 N 0.25703(17) 0.08809(16) 0.13991(8) 0.0150(3) Uani 1 1 d D U . . .
C16 C 0.4832(2) 0.3829(2) 0.26415(11) 0.0197(3) Uani 1 1 d D U . . .
H16A H 0.5882 0.3238 0.2400 0.029 Uiso 1 1 calc R U . . .
H16B H 0.5093 0.4069 0.3292 0.029 Uiso 1 1 calc R U . . .
H16C H 0.4680 0.4927 0.2321 0.029 Uiso 1 1 calc R U . . .
C17 C 0.0103(2) 0.3448(2) 0.24345(11) 0.0199(3) Uani 1 1 d D U . . .
H17A H -0.0059 0.4088 0.1866 0.030 Uiso 1 1 calc R U . . .
H17B H 0.0094 0.4258 0.2951 0.030 Uiso 1 1 calc R U . . .
H17C H -0.0929 0.2555 0.2471 0.030 Uiso 1 1 calc R 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 C9 1.389(2) . ?
C1 C2 1.391(2) . ?
C1 H1 0.9500 . ?
Al1 N2 1.9231(13) . ?
Al1 N1 1.9235(14) . ?
Al1 C16 1.9602(16) . ?
Al1 C17 1.9625(16) . ?
C2 N1 1.3502(19) . ?
C2 S1 1.7471(16) . ?
S1 C3 1.7384(16) . ?
C3 C4 1.386(2) . ?
C3 C8 1.398(2) . ?
C4 C5 1.387(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(2) . ?
C7 H7 0.9500 . ?
C8 N1 1.4027(19) . ?
C9 N2 1.3533(19) . ?
C9 S2 1.7446(15) . ?
S2 C10 1.7387(16) . ?
C10 C11 1.395(2) . ?
C10 C15 1.403(2) . ?
C11 C12 1.388(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.396(2) . ?
C14 H14 0.9500 . ?
C15 N2 1.3966(19) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
C9 C1 C2 123.53(14) . . ?
C9 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
N2 Al1 N1 94.79(6) . . ?
N2 Al1 C16 111.16(6) . . ?
N1 Al1 C16 111.26(7) . . ?
N2 Al1 C17 108.76(6) . . ?
N1 Al1 C17 110.46(7) . . ?
C16 Al1 C17 117.96(7) . . ?
N1 C2 C1 126.48(14) . . ?
N1 C2 S1 113.12(12) . . ?
C1 C2 S1 120.40(12) . . ?
C3 S1 C2 90.72(7) . . ?
C4 C3 C8 121.50(15) . . ?
C4 C3 S1 128.48(13) . . ?
C8 C3 S1 110.02(11) . . ?
C3 C4 C5 118.30(16) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 120.66(15) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 120.98(15) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 118.85(15) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C7 C8 C3 119.70(14) . . ?
C7 C8 N1 126.02(14) . . ?
C3 C8 N1 114.28(13) . . ?
C2 N1 C8 111.86(12) . . ?
C2 N1 Al1 124.26(11) . . ?
C8 N1 Al1 123.84(10) . . ?
N2 C9 C1 126.23(14) . . ?
N2 C9 S2 113.19(11) . . ?
C1 C9 S2 120.58(12) . . ?
C10 S2 C9 90.72(7) . . ?
C11 C10 C15 121.51(14) . . ?
C11 C10 S2 128.59(12) . . ?
C15 C10 S2 109.90(11) . . ?
C12 C11 C10 117.98(15) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C11 C12 C13 120.89(15) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 121.19(15) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 118.87(14) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C15 N2 126.12(14) . . ?
C14 C15 C10 119.55(14) . . ?
N2 C15 C10 114.32(13) . . ?
C9 N2 C15 111.87(12) . . ?
C9 N2 Al1 124.35(10) . . ?
C15 N2 Al1 123.62(10) . . ?
Al1 C16 H16A 109.5 . . ?
Al1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Al1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Al1 C17 H17A 109.5 . . ?
Al1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Al1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C9 C1 C2 N1 1.6(3) . . . . ?
C9 C1 C2 S1 -178.36(12) . . . . ?
N1 C2 S1 C3 -0.10(12) . . . . ?
C1 C2 S1 C3 179.90(13) . . . . ?
C2 S1 C3 C4 179.81(16) . . . . ?
C2 S1 C3 C8 0.10(12) . . . . ?
C8 C3 C4 C5 -0.1(2) . . . . ?
S1 C3 C4 C5 -179.78(12) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C6 C7 C8 C3 0.4(2) . . . . ?
C6 C7 C8 N1 179.84(14) . . . . ?
C4 C3 C8 C7 -0.3(2) . . . . ?
S1 C3 C8 C7 179.45(11) . . . . ?
C4 C3 C8 N1 -179.81(14) . . . . ?
S1 C3 C8 N1 -0.08(16) . . . . ?
C1 C2 N1 C8 -179.93(14) . . . . ?
S1 C2 N1 C8 0.07(16) . . . . ?
C1 C2 N1 Al1 2.5(2) . . . . ?
S1 C2 N1 Al1 -177.54(7) . . . . ?
C7 C8 N1 C2 -179.48(14) . . . . ?
C3 C8 N1 C2 0.01(18) . . . . ?
C7 C8 N1 Al1 -1.9(2) . . . . ?
C3 C8 N1 Al1 177.63(10) . . . . ?
C2 C1 C9 N2 -0.4(3) . . . . ?
C2 C1 C9 S2 179.67(12) . . . . ?
N2 C9 S2 C10 0.10(12) . . . . ?
C1 C9 S2 C10 180.00(13) . . . . ?
C9 S2 C10 C11 -179.36(15) . . . . ?
C9 S2 C10 C15 -0.02(11) . . . . ?
C15 C10 C11 C12 -0.3(2) . . . . ?
S2 C10 C11 C12 178.98(12) . . . . ?
C10 C11 C12 C13 0.6(2) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C13 C14 C15 N2 -179.00(14) . . . . ?
C13 C14 C15 C10 0.6(2) . . . . ?
C11 C10 C15 C14 -0.3(2) . . . . ?
S2 C10 C15 C14 -179.69(11) . . . . ?
C11 C10 C15 N2 179.33(13) . . . . ?
S2 C10 C15 N2 -0.06(16) . . . . ?
C1 C9 N2 C15 179.95(14) . . . . ?
S2 C9 N2 C15 -0.15(16) . . . . ?
C1 C9 N2 Al1 -4.7(2) . . . . ?
S2 C9 N2 Al1 175.24(7) . . . . ?
C14 C15 N2 C9 179.73(14) . . . . ?
C10 C15 N2 C9 0.14(19) . . . . ?
C14 C15 N2 Al1 4.3(2) . . . . ?
C10 C15 N2 Al1 -175.29(10) . . . . ?

_refine_diff_density_max         0.435
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-2



_database_code_depnum_ccdc_archive 'CCDC 995113'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ddauer_5

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15.67 H12.67 Al0.83 Cl0.83 N1.67 O1.67'
_chemical_formula_sum            'C15.67 H12.67 Al0.83 Cl0.83 N1.67 O1.67'
_chemical_formula_weight         302.97

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'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

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

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

_cell_length_a                   21.226(3)
_cell_length_b                   15.558(2)
_cell_length_c                   14.163(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.76(2)
_cell_angle_gamma                90
_cell_volume                     4312.9(12)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.08

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             1880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.086
_exptl_absorpt_coefficient_mu    0.287
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7066
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS-2008/2

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'INCOATEC Mo Microsource'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Smart APEX II Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49655
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.559
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4564
_reflns_number_gt                4130
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0262P)²+10.6027P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00031(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4564
_refine_ls_number_parameters     449
_refine_ls_number_restraints     729
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1025
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.048
_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 0.34960(14) 0.5000 0.1333(2) 0.0228(6) Uani 1 2 d DS TU P . .
H1 H 0.3957 0.5000 0.1389 0.027 Uiso 1 2 calc R U P . .
C2 C 0.31580(9) 0.42308(13) 0.12917(14) 0.0203(4) Uani 1 1 d D U . . .
C3 C 0.30352(10) 0.28328(13) 0.13478(15) 0.0223(4) Uani 1 1 d D U . . .
C4 C 0.31421(11) 0.19563(14) 0.14061(16) 0.0276(5) Uani 1 1 d D U . . .
H4 H 0.3572 0.1709 0.1507 0.033 Uiso 1 1 calc R U . . .
C5 C 0.25732(12) 0.14600(14) 0.13069(16) 0.0295(5) Uani 1 1 d D U . . .
H5 H 0.2616 0.0852 0.1343 0.035 Uiso 1 1 calc R U . . .
C6 C 0.19443(12) 0.18276(14) 0.11562(16) 0.0289(5) Uani 1 1 d D U . . .
H6 H 0.1570 0.1464 0.1090 0.035 Uiso 1 1 calc R U . . .
C7 C 0.18487(11) 0.27195(13) 0.10987(15) 0.0246(4) Uani 1 1 d D U . . .
H7 H 0.1419 0.2972 0.0994 0.030 Uiso 1 1 calc R U . . .
C8 C 0.24139(10) 0.32132(12) 0.12024(14) 0.0204(4) Uani 1 1 d D U . . .
O1 O 0.35044(7) 0.34740(9) 0.14121(11) 0.0239(3) Uani 1 1 d D U . . .
N1 N 0.25005(8) 0.41094(10) 0.11648(12) 0.0189(3) Uani 1 1 d D U . . .
Al1 Al 0.18464(4) 0.5000 0.09205(6) 0.01825(18) Uani 1 2 d DS TU P . .
Cl1 Cl 0.11813(17) 0.5000 -0.0656(2) 0.0215(4) Uani 0.821(4) 2 d DS TU P A 1
C9 C 0.1366(10) 0.5000 0.1841(13) 0.0270(9) Uani 0.821(4) 2 d DS TU P A 1
H9A H 0.1691 0.5106 0.2543 0.040 Uiso 0.4105(18) 1 calc R U P A 1
H9B H 0.1146 0.4441 0.1809 0.040 Uiso 0.4105(18) 1 calc R U P A 1
H9C H 0.1018 0.5453 0.1637 0.040 Uiso 0.4105(18) 1 calc R U P A 1
Cl1' Cl 0.1352(11) 0.5000 0.1919(15) 0.0270(9) Uani 0.179(4) 2 d S TU P A 2
C9' C 0.124(4) 0.5000 -0.056(5) 0.0215(4) Uani 0.179(4) 2 d S TU P A 2
H9'A H 0.0898 0.5455 -0.0691 0.032 Uiso 0.0895(18) 1 calc R U P A 2
H9'B H 0.1011 0.4442 -0.0742 0.032 Uiso 0.0895(18) 1 calc R U P A 2
H9'C H 0.1514 0.5103 -0.0967 0.032 Uiso 0.0895(18) 1 calc R U P A 2
C10 C 0.32333(16) 0.5000 0.3787(2) 0.0261(6) Uani 1 2 d DS TU P . .
H10 H 0.3158 0.5000 0.3081 0.031 Uiso 1 2 calc R U P . .
C11 C 0.32871(10) 0.42296(13) 0.42932(15) 0.0223(4) Uani 1 1 d D U . . .
C12 C 0.32868(10) 0.28316(14) 0.44875(17) 0.0280(5) Uani 1 1 d D U . . .
C13 C 0.32520(11) 0.19555(15) 0.4322(2) 0.0391(6) Uani 1 1 d D U . . .
H13 H 0.3164 0.1713 0.3667 0.047 Uiso 1 1 calc R U . . .
C14 C 0.33536(12) 0.14560(15) 0.5174(2) 0.0441(7) Uani 1 1 d D U . . .
H14 H 0.3336 0.0848 0.5106 0.053 Uiso 1 1 calc R U . . .
C15 C 0.34802(13) 0.18155(15) 0.6124(2) 0.0419(6) Uani 1 1 d D U . . .
H15 H 0.3549 0.1447 0.6690 0.050 Uiso 1 1 calc R U . . .
C16 C 0.35099(12) 0.27065(15) 0.6276(2) 0.0335(5) Uani 1 1 d D U . . .
H16 H 0.3592 0.2953 0.6927 0.040 Uiso 1 1 calc R U . . .
C17 C 0.34134(10) 0.32070(13) 0.54254(17) 0.0238(4) Uani 1 1 d D U . . .
O2 O 0.32046(8) 0.34758(10) 0.37683(11) 0.0296(3) Uani 1 1 d D U . . .
N2 N 0.34118(8) 0.41062(10) 0.52904(12) 0.0201(3) Uani 1 1 d D U . . .
Al2 Al 0.36168(4) 0.5000 0.62673(6) 0.02055(19) Uani 1 2 d DS TU P . .
Cl2 Cl 0.47036(6) 0.5000 0.71281(8) 0.0344(4) Uani 0.803(4) 2 d DS TU P B 1
C18 C 0.3116(4) 0.5000 0.7160(8) 0.0310(18) Uani 0.803(4) 2 d DS TU P B 1
H18A H 0.3397 0.5265 0.7816 0.046 Uiso 0.402(2) 1 calc R U P B 1
H18B H 0.3007 0.4407 0.7275 0.046 Uiso 0.402(2) 1 calc R U P B 1
H18C H 0.2692 0.5328 0.6838 0.046 Uiso 0.402(2) 1 calc R U P B 1
Cl2' Cl 0.2908(5) 0.5000 0.6988(8) 0.0310(18) Uani 0.197(4) 2 d DS TU P B 2
C18' C 0.4538(8) 0.5000 0.7295(16) 0.0344(4) Uani 0.197(4) 2 d DS TU P B 2
H18D H 0.4587 0.5463 0.7788 0.052 Uiso 0.098(2) 1 calc R U P B 2
H18E H 0.4862 0.5091 0.6965 0.052 Uiso 0.098(2) 1 calc R U P B 2
H18F H 0.4632 0.4446 0.7653 0.052 Uiso 0.098(2) 1 calc R U P B 2
C19 C 0.5242(4) 0.0005(11) 0.6628(5) 0.0353(15) Uani 0.25 1 d D U P C -1
H19A H 0.5362 0.0005 0.7355 0.042 Uiso 0.25 1 d R U P C -1
C20 C 0.5155(2) 0.0769(3) 0.6100(3) 0.0295(9) Uani 0.5 1 d D U P C -1
C21 C 0.5118(12) 0.2173(6) 0.5888(10) 0.028(2) Uani 0.5 1 d D U P C -1
C22 C 0.5167(7) 0.3048(5) 0.6062(8) 0.031(2) Uani 0.5 1 d D U P C -1
H22 H 0.5289 0.3292 0.6725 0.037 Uiso 0.5 1 calc R U P C -1
C23 C 0.5022(7) 0.3539(3) 0.5192(6) 0.030(2) Uani 0.5 1 d D U P C -1
H23 H 0.5049 0.4147 0.5255 0.036 Uiso 0.5 1 calc R U P C -1
C24 C 0.4839(7) 0.3175(5) 0.4231(8) 0.031(2) Uani 0.5 1 d D U P C -1
H24 H 0.4744 0.3542 0.3657 0.037 Uiso 0.5 1 calc R U P C -1
C25 C 0.4789(12) 0.2284(6) 0.4073(10) 0.032(3) Uani 0.5 1 d D U P C -1
H25 H 0.4632 0.2038 0.3408 0.038 Uiso 0.5 1 calc R U P C -1
C26 C 0.498(2) 0.1791(2) 0.4942(12) 0.0279(11) Uani 0.5 1 d D U P C -1
O3 O 0.52602(16) 0.1528(2) 0.6619(2) 0.0357(7) Uani 0.5 1 d D U P C -1
N3 N 0.4984(11) 0.0888(2) 0.5089(8) 0.0245(14) Uani 0.5 1 d D U P C -1
Al3 Al 0.47456(9) 0.0003(7) 0.40986(17) 0.0224(5) Uani 0.25 1 d D U P C -1
Cl3 Cl 0.36665(9) 0.0007(12) 0.3281(2) 0.0233(7) Uani 0.2034(18) 1 d D U P C -1
C27 C 0.5242(12) -0.001(4) 0.3205(19) 0.024(3) Uani 0.2034(18) 1 d D U P C -1
H27A H 0.5257 0.0575 0.2953 0.036 Uiso 0.2034(18) 1 calc R U P C -1
H27B H 0.5011 -0.0392 0.2624 0.036 Uiso 0.2034(18) 1 calc R U P C -1
H27C H 0.5708 -0.0214 0.3585 0.036 Uiso 0.2034(18) 1 calc R U P C -1
Cl3' Cl 0.5348(13) 0.008(3) 0.322(2) 0.024(3) Uani 0.0466(18) 1 d D U P C -1
C27' C 0.3779(10) -0.011(5) 0.326(4) 0.0233(7) Uani 0.0466(18) 1 d D U P C -1
H27D H 0.3520 -0.0104 0.3707 0.035 Uiso 0.0466(18) 1 calc R U P C -1
H27E H 0.3696 -0.0651 0.2884 0.035 Uiso 0.0466(18) 1 calc R U P C -1
H27F H 0.3631 0.0373 0.2782 0.035 Uiso 0.0466(18) 1 calc R U P C -1
C1T C 0.502(3) 0.3293(3) 0.002(3) 0.032(3) Uani 0.259(4) 1 d DG U P D -2
C2T C 0.503(3) 0.2801(10) -0.080(3) 0.029(5) Uani 0.259(4) 1 d DG U P D -2
H2T H 0.5052 0.3073 -0.1383 0.035 Uiso 0.259(4) 1 calc R U P D -2
C3T C 0.501(2) 0.1909(9) -0.075(2) 0.024(4) Uani 0.259(4) 1 d DG U P D -2
H3T H 0.5017 0.1573 -0.1305 0.029 Uiso 0.259(4) 1 calc R U P D -2
C4T C 0.498(3) 0.1510(3) 0.011(2) 0.027(4) Uani 0.259(4) 1 d DG U P D -2
H4T H 0.4962 0.0901 0.0140 0.032 Uiso 0.259(4) 1 calc R U P D -2
C5T C 0.497(2) 0.2003(10) 0.092(2) 0.035(5) Uani 0.259(4) 1 d DG U P D -2
H5T H 0.4944 0.1730 0.1507 0.042 Uiso 0.259(4) 1 calc R U P D -2
C6T C 0.499(3) 0.2895(10) 0.087(3) 0.036(5) Uani 0.259(4) 1 d DG U P D -2
H6T H 0.4980 0.3231 0.1429 0.044 Uiso 0.259(4) 1 calc R U P D -2
C7T C 0.502(4) 0.4272(5) -0.004(4) 0.047(4) Uani 0.259(4) 1 d D U P D -2
H7T1 H 0.5090 0.4451 -0.0656 0.070 Uiso 0.259(4) 1 calc R U P D -2
H7T2 H 0.5380 0.4505 0.0567 0.070 Uiso 0.259(4) 1 calc R U P D -2
H7T3 H 0.4573 0.4490 -0.0083 0.070 Uiso 0.259(4) 1 calc R U P D -2
C1A C 0.4978(5) 0.2353(7) 0.0528(6) 0.032(2) Uani 0.241(4) 1 d DG U P D -3
C2A C 0.4995(6) 0.3202(5) 0.0233(7) 0.034(5) Uani 0.241(4) 1 d DG U P D -3
H2A H 0.4992 0.3657 0.0679 0.041 Uiso 0.241(4) 1 calc R U P D -3
C3A C 0.5016(6) 0.3386(4) -0.0715(8) 0.039(3) Uani 0.241(4) 1 d DG U P D -3
H3A H 0.5028 0.3966 -0.0916 0.047 Uiso 0.241(4) 1 calc R U P D -3
C4A C 0.5021(5) 0.2721(6) -0.1367(5) 0.036(3) Uani 0.241(4) 1 d DG U P D -3
H4A H 0.5036 0.2846 -0.2015 0.043 Uiso 0.241(4) 1 calc R U P D -3
C5A C 0.5004(8) 0.1872(5) -0.1072(8) 0.031(4) Uani 0.241(4) 1 d DG U P D -3
H5A H 0.5008 0.1417 -0.1518 0.037 Uiso 0.241(4) 1 calc R U P D -3
C6A C 0.4983(8) 0.1688(5) -0.0124(8) 0.034(3) Uani 0.241(4) 1 d DG U P D -3
H6A H 0.4972 0.1108 0.0077 0.041 Uiso 0.241(4) 1 calc R U P D -3
C7A C 0.4960(6) 0.2171(9) 0.1556(9) 0.045(3) Uani 0.241(4) 1 d D U P D -3
H7A1 H 0.4967 0.1548 0.1663 0.068 Uiso 0.241(4) 1 calc R U P D -3
H7A2 H 0.4542 0.2413 0.1585 0.068 Uiso 0.241(4) 1 calc R U P D -3
H7A3 H 0.5359 0.2432 0.2091 0.068 Uiso 0.241(4) 1 calc R U P D -3


_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 C2 1.385(2) . ?
C1 C2 1.385(2) 6_565 ?
C1 H1 0.9500 . ?
C2 N1 1.350(2) . ?
C2 O1 1.363(2) . ?
C3 C4 1.380(3) . ?
C3 C8 1.386(3) . ?
C3 O1 1.388(2) . ?
C4 C5 1.394(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.400(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(3) . ?
C7 H7 0.9500 . ?
C8 N1 1.410(2) . ?
N1 Al1 1.8961(17) . ?
Al1 N1 1.8961(17) 6_565 ?
Al1 C9 1.942(12) . ?
Al1 C9' 1.99(6) . ?
Al1 Cl1' 2.061(14) . ?
Al1 Cl1 2.130(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9' H9'A 0.9800 . ?
C9' H9'B 0.9800 . ?
C9' H9'C 0.9800 . ?
C10 C11 1.378(2) 6_565 ?
C10 C11 1.378(2) . ?
C10 H10 0.9500 . ?
C11 N2 1.346(3) . ?
C11 O2 1.363(2) . ?
C12 C17 1.379(3) . ?
C12 C13 1.380(3) . ?
C12 O2 1.391(3) . ?
C13 C14 1.380(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.401(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9500 . ?
C17 N2 1.412(3) . ?
N2 Al2 1.8899(17) . ?
Al2 N2 1.8899(17) 6_565 ?
Al2 C18' 1.934(14) . ?
Al2 C18 1.940(9) . ?
Al2 Cl2' 2.120(9) . ?
Al2 Cl2 2.1522(15) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18' H18D 0.9800 . ?
C18' H18E 0.9800 . ?
C18' H18F 0.9800 . ?
C19 C20 1.378(15) . ?
C19 H19A 0.9603 . ?
C20 N3 1.348(10) . ?
C20 O3 1.363(5) . ?
C21 C22 1.381(10) . ?
C21 O3 1.388(11) . ?
C21 C26 1.390(12) . ?
C22 C23 1.379(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(9) . ?
C23 H23 0.9500 . ?
C24 C25 1.401(10) . ?
C24 H24 0.9500 . ?
C25 C26 1.372(11) . ?
C25 H25 0.9500 . ?
C26 N3 1.419(5) . ?
N3 Al3 1.890(10) . ?
Al3 C27 1.935(12) . ?
Al3 C27' 1.939(17) . ?
Al3 Cl3' 2.105(13) . ?
Al3 Cl3 2.129(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C27' H27D 0.9800 . ?
C27' H27E 0.9800 . ?
C27' H27F 0.9800 . ?
C1T C2T 1.3900 . ?
C1T C6T 1.3900 . ?
C1T C7T 1.525(9) . ?
C2T C3T 1.3900 . ?
C2T H2T 0.9500 . ?
C3T C4T 1.3900 . ?
C3T H3T 0.9500 . ?
C4T C5T 1.3900 . ?
C4T H4T 0.9500 . ?
C5T C6T 1.3900 . ?
C5T H5T 0.9500 . ?
C6T H6T 0.9500 . ?
C7T H7T1 0.9800 . ?
C7T H7T2 0.9800 . ?
C7T H7T3 0.9800 . ?
C1A C2A 1.3900 . ?
C1A C6A 1.3900 . ?
C1A C7A 1.498(11) . ?
C2A C3A 1.3900 . ?
C2A H2A 0.9500 . ?
C3A C4A 1.3900 . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3900 . ?
C4A H4A 0.9500 . ?
C5A C6A 1.3900 . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A H7A1 0.9800 . ?
C7A H7A2 0.9800 . ?
C7A H7A3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C2 119.6(3) . 6_565 ?
C2 C1 H1 120.2 . . ?
C2 C1 H1 120.2 6_565 . ?
N1 C2 O1 112.06(17) . . ?
N1 C2 C1 128.21(19) . . ?
O1 C2 C1 119.71(18) . . ?
C4 C3 C8 123.8(2) . . ?
C4 C3 O1 127.55(19) . . ?
C8 C3 O1 108.68(17) . . ?
C3 C4 C5 115.2(2) . . ?
C3 C4 H4 122.4 . . ?
C5 C4 H4 122.4 . . ?
C6 C5 C4 122.0(2) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 121.7(2) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 116.34(19) . . ?
C8 C7 H7 121.8 . . ?
C6 C7 H7 121.8 . . ?
C7 C8 C3 120.98(18) . . ?
C7 C8 N1 131.70(18) . . ?
C3 C8 N1 107.30(17) . . ?
C2 O1 C3 105.91(15) . . ?
C2 N1 C8 106.05(16) . . ?
C2 N1 Al1 124.64(13) . . ?
C8 N1 Al1 129.24(13) . . ?
N1 Al1 N1 93.90(10) 6_565 . ?
N1 Al1 C9 114.5(4) 6_565 . ?
N1 Al1 C9 114.5(4) . . ?
N1 Al1 C9' 108.8(16) 6_565 . ?
N1 Al1 C9' 108.8(16) . . ?
N1 Al1 Cl1' 113.9(4) 6_565 . ?
N1 Al1 Cl1' 113.9(4) . . ?
C9' Al1 Cl1' 115(3) . . ?
N1 Al1 Cl1 109.44(9) 6_565 . ?
N1 Al1 Cl1 109.44(9) . . ?
C9 Al1 Cl1 113.3(6) . . ?
Al1 C9 H9A 109.5 . . ?
Al1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Al1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Al1 C9' H9'A 109.5 . . ?
Al1 C9' H9'B 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
Al1 C9' H9'C 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
C11 C10 C11 120.8(3) 6_565 . ?
C11 C10 H10 119.6 6_565 . ?
C11 C10 H10 119.6 . . ?
N2 C11 O2 112.40(17) . . ?
N2 C11 C10 127.78(19) . . ?
O2 C11 C10 119.81(18) . . ?
C17 C12 C13 124.0(2) . . ?
C17 C12 O2 108.82(18) . . ?
C13 C12 O2 127.1(2) . . ?
C12 C13 C14 115.3(2) . . ?
C12 C13 H13 122.4 . . ?
C14 C13 H13 122.4 . . ?
C13 C14 C15 121.9(2) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C16 122.0(2) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C17 C16 C15 116.2(2) . . ?
C17 C16 H16 121.9 . . ?
C15 C16 H16 121.9 . . ?
C12 C17 C16 120.6(2) . . ?
C12 C17 N2 107.45(18) . . ?
C16 C17 N2 131.9(2) . . ?
C11 O2 C12 105.51(16) . . ?
C11 N2 C17 105.82(17) . . ?
C11 N2 Al2 124.01(14) . . ?
C17 N2 Al2 129.95(14) . . ?
N2 Al2 N2 94.75(11) . 6_565 ?
N2 Al2 C18' 115.5(4) . . ?
N2 Al2 C18' 115.5(4) 6_565 . ?
N2 Al2 C18 116.61(18) . . ?
N2 Al2 C18 116.61(18) 6_565 . ?
N2 Al2 Cl2' 110.32(19) . . ?
N2 Al2 Cl2' 110.32(19) 6_565 . ?
C18' Al2 Cl2' 109.7(7) . . ?
N2 Al2 Cl2 107.91(6) . . ?
N2 Al2 Cl2 107.91(6) 6_565 . ?
C18 Al2 Cl2 111.6(3) . . ?
Al2 C18 H18A 109.5 . . ?
Al2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Al2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Al2 C18' H18D 109.5 . . ?
Al2 C18' H18E 109.5 . . ?
H18D C18' H18E 109.5 . . ?
Al2 C18' H18F 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?
C20 C19 H19A 120.3 . . ?
N3 C20 O3 112.0(4) . . ?
N3 C20 C19 128.3(6) . . ?
O3 C20 C19 119.7(6) . . ?
C22 C21 O3 126.8(10) . . ?
C22 C21 C26 124.6(9) . . ?
O3 C21 C26 108.3(8) . . ?
C23 C22 C21 114.3(9) . . ?
C23 C22 H22 122.9 . . ?
C21 C22 H22 122.9 . . ?
C22 C23 C24 122.2(4) . . ?
C22 C23 H23 118.9 . . ?
C24 C23 H23 118.9 . . ?
C23 C24 C25 122.5(9) . . ?
C23 C24 H24 118.8 . . ?
C25 C24 H24 118.8 . . ?
C26 C25 C24 115.6(9) . . ?
C26 C25 H25 122.2 . . ?
C24 C25 H25 122.2 . . ?
C25 C26 C21 120.2(5) . . ?
C25 C26 N3 131.9(11) . . ?
C21 C26 N3 107.1(10) . . ?
C20 O3 C21 106.3(5) . . ?
C20 N3 C26 106.0(7) . . ?
C20 N3 Al3 124.9(4) . . ?
C26 N3 Al3 128.9(9) . . ?
N3 Al3 C27 115.7(15) . . ?
N3 Al3 C27' 115.7(17) . . ?
C27 Al3 C27' 108(2) . . ?
N3 Al3 Cl3' 110.2(11) . . ?
C27 Al3 Cl3' 5.6(18) . . ?
C27' Al3 Cl3' 112.7(16) . . ?
N3 Al3 Cl3 108.9(8) . . ?
C27 Al3 Cl3 112.8(8) . . ?
C27' Al3 Cl3 6.8(18) . . ?
Cl3' Al3 Cl3 116.7(8) . . ?
Al3 C27 H27A 109.5 . . ?
Al3 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
Al3 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
Al3 C27' H27D 109.5 . . ?
Al3 C27' H27E 109.5 . . ?
H27D C27' H27E 109.5 . . ?
Al3 C27' H27F 109.5 . . ?
H27D C27' H27F 109.5 . . ?
H27E C27' H27F 109.5 . . ?
C2T C1T C6T 120.0 . . ?
C2T C1T C7T 120.4(15) . . ?
C6T C1T C7T 119.6(15) . . ?
C1T C2T C3T 120.0 . . ?
C1T C2T H2T 120.0 . . ?
C3T C2T H2T 120.0 . . ?
C4T C3T C2T 120.0 . . ?
C4T C3T H3T 120.0 . . ?
C2T C3T H3T 120.0 . . ?
C3T C4T C5T 120.0 . . ?
C3T C4T H4T 120.0 . . ?
C5T C4T H4T 120.0 . . ?
C6T C5T C4T 120.0 . . ?
C6T C5T H5T 120.0 . . ?
C4T C5T H5T 120.0 . . ?
C5T C6T C1T 120.0 . . ?
C5T C6T H6T 120.0 . . ?
C1T C6T H6T 120.0 . . ?
C1T C7T H7T1 109.5 . . ?
C1T C7T H7T2 109.5 . . ?
H7T1 C7T H7T2 109.5 . . ?
C1T C7T H7T3 109.5 . . ?
H7T1 C7T H7T3 109.5 . . ?
H7T2 C7T H7T3 109.5 . . ?
C2A C1A C6A 120.0 . . ?
C2A C1A C7A 119.0(9) . . ?
C6A C1A C7A 121.0(9) . . ?
C3A C2A C1A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C2A C3A C4A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C5A C4A C3A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C4A C5A C6A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C5A C6A C1A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C1A C6A H6A 120.0 . . ?
C1A C7A H7A1 109.5 . . ?
C1A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C1A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?

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
C2 C1 C2 N1 3.4(4) 6_565 . . . ?
C2 C1 C2 O1 -174.91(16) 6_565 . . . ?
C8 C3 C4 C5 0.0(3) . . . . ?
O1 C3 C4 C5 -179.44(18) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 C3 0.4(3) . . . . ?
C6 C7 C8 N1 178.5(2) . . . . ?
C4 C3 C8 C7 -0.4(3) . . . . ?
O1 C3 C8 C7 179.18(17) . . . . ?
C4 C3 C8 N1 -178.90(19) . . . . ?
O1 C3 C8 N1 0.7(2) . . . . ?
N1 C2 O1 C3 0.6(2) . . . . ?
C1 C2 O1 C3 179.1(2) . . . . ?
C4 C3 O1 C2 178.8(2) . . . . ?
C8 C3 O1 C2 -0.8(2) . . . . ?
O1 C2 N1 C8 -0.2(2) . . . . ?
C1 C2 N1 C8 -178.6(2) . . . . ?
O1 C2 N1 Al1 -177.39(12) . . . . ?
C1 C2 N1 Al1 4.2(3) . . . . ?
C7 C8 N1 C2 -178.6(2) . . . . ?
C3 C8 N1 C2 -0.3(2) . . . . ?
C7 C8 N1 Al1 -1.6(3) . . . . ?
C3 C8 N1 Al1 176.73(13) . . . . ?
C2 N1 Al1 N1 -8.62(19) . . . 6_565 ?
C8 N1 Al1 N1 174.86(12) . . . 6_565 ?
C2 N1 Al1 C9 -127.9(6) . . . . ?
C8 N1 Al1 C9 55.6(6) . . . . ?
C2 N1 Al1 C9' 103(2) . . . . ?
C8 N1 Al1 C9' -74(2) . . . . ?
C2 N1 Al1 Cl1' -127.0(6) . . . . ?
C8 N1 Al1 Cl1' 56.5(6) . . . . ?
C2 N1 Al1 Cl1 103.58(17) . . . . ?
C8 N1 Al1 Cl1 -72.94(19) . . . . ?
C11 C10 C11 N2 -2.1(5) 6_565 . . . ?
C11 C10 C11 O2 177.34(17) 6_565 . . . ?
C17 C12 C13 C14 0.0(3) . . . . ?
O2 C12 C13 C14 180.0(2) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C13 C12 C17 C16 -0.5(3) . . . . ?
O2 C12 C17 C16 179.52(18) . . . . ?
C13 C12 C17 N2 179.8(2) . . . . ?
O2 C12 C17 N2 -0.1(2) . . . . ?
C15 C16 C17 C12 0.8(3) . . . . ?
C15 C16 C17 N2 -179.6(2) . . . . ?
N2 C11 O2 C12 -0.3(2) . . . . ?
C10 C11 O2 C12 -179.8(2) . . . . ?
C17 C12 O2 C11 0.3(2) . . . . ?
C13 C12 O2 C11 -179.7(2) . . . . ?
O2 C11 N2 C17 0.2(2) . . . . ?
C10 C11 N2 C17 179.7(2) . . . . ?
O2 C11 N2 Al2 175.29(13) . . . . ?
C10 C11 N2 Al2 -5.3(3) . . . . ?
C12 C17 N2 C11 -0.1(2) . . . . ?
C16 C17 N2 C11 -179.7(2) . . . . ?
C12 C17 N2 Al2 -174.71(14) . . . . ?
C16 C17 N2 Al2 5.7(3) . . . . ?
C11 N2 Al2 N2 9.2(2) . . . 6_565 ?
C17 N2 Al2 N2 -177.01(13) . . . 6_565 ?
C11 N2 Al2 C18' -112.0(7) . . . . ?
C17 N2 Al2 C18' 61.8(7) . . . . ?
C11 N2 Al2 C18 132.2(3) . . . . ?
C17 N2 Al2 C18 -54.0(3) . . . . ?
C11 N2 Al2 Cl2' 122.9(3) . . . . ?
C17 N2 Al2 Cl2' -63.3(3) . . . . ?
C11 N2 Al2 Cl2 -101.33(16) . . . . ?
C17 N2 Al2 Cl2 72.44(18) . . . . ?
O3 C21 C22 C23 177.3(16) . . . . ?
C26 C21 C22 C23 4(3) . . . . ?
C21 C22 C23 C24 1(2) . . . . ?
C22 C23 C24 C25 0(2) . . . . ?
C23 C24 C25 C26 -5(3) . . . . ?
C24 C25 C26 C21 9(5) . . . . ?
C24 C25 C26 N3 178(3) . . . . ?
C22 C21 C26 C25 -9(5) . . . . ?
O3 C21 C26 C25 176(2) . . . . ?
C22 C21 C26 N3 179(2) . . . . ?
O3 C21 C26 N3 5(3) . . . . ?
N3 C20 O3 C21 2.7(15) . . . . ?
C19 C20 O3 C21 -178.6(11) . . . . ?
C22 C21 O3 C20 -178.8(17) . . . . ?
C26 C21 O3 C20 -5(2) . . . . ?
O3 C20 N3 C26 0(2) . . . . ?
C19 C20 N3 C26 -178.3(19) . . . . ?
O3 C20 N3 Al3 -176.1(11) . . . . ?
C19 C20 N3 Al3 5(2) . . . . ?
C25 C26 N3 C20 -173(3) . . . . ?
C21 C26 N3 C20 -3(3) . . . . ?
C25 C26 N3 Al3 3(6) . . . . ?
C21 C26 N3 Al3 173.0(18) . . . . ?
C20 N3 Al3 C27 -128(2) . . . . ?
C26 N3 Al3 C27 56(3) . . . . ?
C20 N3 Al3 C27' 104(3) . . . . ?
C26 N3 Al3 C27' -72(4) . . . . ?
C20 N3 Al3 Cl3' -127.1(18) . . . . ?
C26 N3 Al3 Cl3' 57(3) . . . . ?
C20 N3 Al3 Cl3 103.7(16) . . . . ?
C26 N3 Al3 Cl3 -72(3) . . . . ?
C6T C1T C2T C3T 0.0 . . . . ?
C7T C1T C2T C3T -178(5) . . . . ?
C1T C2T C3T C4T 0.0 . . . . ?
C2T C3T C4T C5T 0.0 . . . . ?
C3T C4T C5T C6T 0.0 . . . . ?
C4T C5T C6T C1T 0.0 . . . . ?
C2T C1T C6T C5T 0.0 . . . . ?
C7T C1T C6T C5T 178(5) . . . . ?
C6A C1A C2A C3A 0.0 . . . . ?
C7A C1A C2A C3A 179.6(9) . . . . ?
C1A C2A C3A C4A 0.0 . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
C4A C5A C6A C1A 0.0 . . . . ?
C2A C1A C6A C5A 0.0 . . . . ?
C7A C1A C6A C5A -179.6(9) . . . . ?

_refine_diff_density_max         0.384
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-2



_database_code_depnum_ccdc_archive 'CCDC 995114'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ddauer_6

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 Al Cl N2 S2'
_chemical_formula_sum            'C16 H12 Al Cl N2 S2'
_chemical_formula_weight         358.83

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.074(2)
_cell_length_b                   7.694(2)
_cell_length_c                   14.664(3)
_cell_angle_alpha                89.97(2)
_cell_angle_beta                 85.29(2)
_cell_angle_gamma                85.89(2)
_cell_volume                     793.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4677
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      25.31

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.555
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.754357
_exptl_absorpt_correction_T_max  0.914277
_exptl_absorpt_process_details   TWINABS-2008/2

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'INCOATEC Mo Microsource'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Smart APEX II Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21727
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.393
_diffrn_reflns_theta_max         25.376
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2882
_reflns_number_gt                2502
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0326P)²+0.6194P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2882
_refine_ls_number_parameters     209
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0761
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_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 0.2244(3) 1.2014(3) 0.28509(16) 0.0160(5) Uani 1 1 d D . . . .
H1 H 0.2099 1.3241 0.2939 0.019 Uiso 1 1 calc R U . . .
C2 C 0.2387(3) 1.0971(3) 0.36176(16) 0.0145(5) Uani 1 1 d D . . . .
S1 S 0.22903(9) 1.18816(7) 0.47090(4) 0.01635(15) Uani 1 1 d D . . . .
C3 C 0.2527(4) 0.9811(3) 0.51940(16) 0.0147(5) Uani 1 1 d D . . . .
C4 C 0.2550(4) 0.9383(3) 0.61156(16) 0.0181(5) Uani 1 1 d D . . . .
H4 H 0.2466 1.0263 0.6574 0.022 Uiso 1 1 calc R U . . .
C5 C 0.2698(4) 0.7626(3) 0.63454(17) 0.0191(5) Uani 1 1 d D . . . .
H5 H 0.2695 0.7298 0.6970 0.023 Uiso 1 1 calc R U . . .
C6 C 0.2851(4) 0.6342(3) 0.56689(16) 0.0179(5) Uani 1 1 d D . . . .
H6 H 0.2965 0.5150 0.5839 0.021 Uiso 1 1 calc R U . . .
C7 C 0.2841(3) 0.6774(3) 0.47499(16) 0.0158(5) Uani 1 1 d D . . . .
H7 H 0.2942 0.5892 0.4292 0.019 Uiso 1 1 calc R U . . .
C8 C 0.2677(3) 0.8533(3) 0.45135(15) 0.0132(5) Uani 1 1 d D . . . .
N1 N 0.2599(3) 0.9193(2) 0.36198(13) 0.0135(4) Uani 1 1 d D . . . .
C9 C 0.2301(3) 1.1377(3) 0.19627(16) 0.0147(5) Uani 1 1 d D . . . .
S2 S 0.21083(9) 1.27896(7) 0.10365(4) 0.01934(16) Uani 1 1 d D . . . .
C10 C 0.2343(3) 1.1033(3) 0.02753(16) 0.0167(5) Uani 1 1 d D . . . .
C11 C 0.2324(4) 1.1064(3) -0.06724(16) 0.0209(6) Uani 1 1 d D . . . .
H11 H 0.2166 1.2135 -0.0990 0.025 Uiso 1 1 calc R U . . .
C12 C 0.2541(4) 0.9493(3) -0.11390(17) 0.0237(6) Uani 1 1 d D . . . .
H12 H 0.2551 0.9484 -0.1787 0.028 Uiso 1 1 calc R U . . .
C13 C 0.2747(4) 0.7918(3) -0.06709(17) 0.0215(6) Uani 1 1 d D . . . .
H13 H 0.2890 0.6853 -0.1006 0.026 Uiso 1 1 calc R U . . .
C14 C 0.2744(3) 0.7885(3) 0.02728(16) 0.0183(5) Uani 1 1 d D . . . .
H14 H 0.2878 0.6810 0.0588 0.022 Uiso 1 1 calc R U . . .
C15 C 0.2542(3) 0.9463(3) 0.07520(15) 0.0151(5) Uani 1 1 d D . . . .
N2 N 0.2515(3) 0.9666(2) 0.17069(13) 0.0134(4) Uani 1 1 d D . . . .
Al1 Al 0.25990(10) 0.78067(8) 0.25539(5) 0.01404(17) Uani 1 1 d D . . . .
C16 C 0.488(2) 0.618(2) 0.2331(13) 0.0195(7) Uani 0.705(3) 1 d D . P A 1
H16A H 0.5069 0.5883 0.1678 0.029 Uiso 0.705(3) 1 calc R U P A 1
H16B H 0.4714 0.5120 0.2688 0.029 Uiso 0.705(3) 1 calc R U P A 1
H16C H 0.5998 0.6737 0.2514 0.029 Uiso 0.705(3) 1 calc R U P A 1
Cl1 Cl 0.0021(4) 0.6550(4) 0.2610(3) 0.0179(3) Uani 0.705(3) 1 d D . P A 1
Cl1' Cl 0.5003(13) 0.6119(13) 0.2370(7) 0.0195(7) Uani 0.295(3) 1 d D . P A 2
C16' C 0.015(4) 0.662(5) 0.261(3) 0.0179(3) Uani 0.295(3) 1 d D . P A 2
H16D H 0.0029 0.5930 0.3176 0.027 Uiso 0.295(3) 1 calc R U P A 2
H16E H 0.0149 0.5847 0.2082 0.027 Uiso 0.295(3) 1 calc R U P A 2
H16F H -0.0925 0.7496 0.2614 0.027 Uiso 0.295(3) 1 calc R U P A 2


_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 C2 1.387(3) . ?
C1 C9 1.388(3) . ?
C1 H1 0.9500 . ?
C2 N1 1.365(3) . ?
C2 S1 1.742(2) . ?
S1 C3 1.747(2) . ?
C3 C4 1.392(3) . ?
C3 C8 1.394(3) . ?
C4 C5 1.392(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.395(3) . ?
C7 H7 0.9500 . ?
C8 N1 1.409(3) . ?
N1 Al1 1.893(2) . ?
C9 N2 1.364(3) . ?
C9 S2 1.747(2) . ?
S2 C10 1.743(2) . ?
C10 C11 1.391(3) . ?
C10 C15 1.399(3) . ?
C11 C12 1.382(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.397(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.396(3) . ?
C14 H14 0.9500 . ?
C15 N2 1.407(3) . ?
N2 Al1 1.895(2) . ?
Al1 C16 1.976(14) . ?
Al1 C16' 2.01(2) . ?
Al1 Cl1' 2.064(8) . ?
Al1 Cl1 2.120(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16' H16D 0.9800 . ?
C16' H16E 0.9800 . ?
C16' H16F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 124.1(2) . . ?
C2 C1 H1 118.0 . . ?
C9 C1 H1 118.0 . . ?
N1 C2 C1 125.9(2) . . ?
N1 C2 S1 113.05(16) . . ?
C1 C2 S1 121.02(17) . . ?
C2 S1 C3 90.81(11) . . ?
C4 C3 C8 121.6(2) . . ?
C4 C3 S1 128.10(18) . . ?
C8 C3 S1 110.27(17) . . ?
C3 C4 C5 118.0(2) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 118.6(2) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C3 C8 C7 120.0(2) . . ?
C3 C8 N1 114.15(19) . . ?
C7 C8 N1 125.8(2) . . ?
C2 N1 C8 111.72(18) . . ?
C2 N1 Al1 123.45(15) . . ?
C8 N1 Al1 124.68(14) . . ?
N2 C9 C1 126.1(2) . . ?
N2 C9 S2 112.96(17) . . ?
C1 C9 S2 120.98(17) . . ?
C10 S2 C9 90.84(11) . . ?
C11 C10 C15 121.5(2) . . ?
C11 C10 S2 128.24(19) . . ?
C15 C10 S2 110.25(18) . . ?
C12 C11 C10 118.1(2) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C11 C12 C13 120.9(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 118.6(2) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C14 C15 C10 119.8(2) . . ?
C14 C15 N2 126.0(2) . . ?
C10 C15 N2 114.1(2) . . ?
C9 N2 C15 111.80(19) . . ?
C9 N2 Al1 123.29(16) . . ?
C15 N2 Al1 124.80(15) . . ?
N1 Al1 N2 96.84(9) . . ?
N1 Al1 C16 113.9(6) . . ?
N2 Al1 C16 113.1(6) . . ?
N1 Al1 C16' 108.3(11) . . ?
N2 Al1 C16' 110.1(12) . . ?
N1 Al1 Cl1' 111.9(3) . . ?
N2 Al1 Cl1' 114.4(3) . . ?
C16' Al1 Cl1' 113.9(10) . . ?
N1 Al1 Cl1 108.57(12) . . ?
N2 Al1 Cl1 109.98(13) . . ?
C16 Al1 Cl1 113.2(5) . . ?
Al1 C16 H16A 109.5 . . ?
Al1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Al1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Al1 C16' H16D 109.5 . . ?
Al1 C16' H16E 109.5 . . ?
H16D C16' H16E 109.5 . . ?
Al1 C16' H16F 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?

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
C9 C1 C2 N1 -0.1(4) . . . . ?
C9 C1 C2 S1 -179.67(19) . . . . ?
N1 C2 S1 C3 -0.36(19) . . . . ?
C1 C2 S1 C3 179.3(2) . . . . ?
C2 S1 C3 C4 -178.9(2) . . . . ?
C2 S1 C3 C8 0.28(19) . . . . ?
C8 C3 C4 C5 -1.0(4) . . . . ?
S1 C3 C4 C5 178.1(2) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
C5 C6 C7 C8 0.2(4) . . . . ?
C4 C3 C8 C7 0.5(4) . . . . ?
S1 C3 C8 C7 -178.72(19) . . . . ?
C4 C3 C8 N1 179.1(2) . . . . ?
S1 C3 C8 N1 -0.2(3) . . . . ?
C6 C7 C8 C3 -0.1(4) . . . . ?
C6 C7 C8 N1 -178.5(2) . . . . ?
C1 C2 N1 C8 -179.3(2) . . . . ?
S1 C2 N1 C8 0.3(3) . . . . ?
C1 C2 N1 Al1 -3.6(3) . . . . ?
S1 C2 N1 Al1 176.06(11) . . . . ?
C3 C8 N1 C2 -0.1(3) . . . . ?
C7 C8 N1 C2 178.4(2) . . . . ?
C3 C8 N1 Al1 -175.78(17) . . . . ?
C7 C8 N1 Al1 2.7(3) . . . . ?
C2 C1 C9 N2 -0.5(4) . . . . ?
C2 C1 C9 S2 179.96(19) . . . . ?
N2 C9 S2 C10 -0.47(18) . . . . ?
C1 C9 S2 C10 179.1(2) . . . . ?
C9 S2 C10 C11 179.6(2) . . . . ?
C9 S2 C10 C15 0.39(19) . . . . ?
C15 C10 C11 C12 -1.1(4) . . . . ?
S2 C10 C11 C12 179.8(2) . . . . ?
C10 C11 C12 C13 0.9(4) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C13 C14 C15 C10 0.2(4) . . . . ?
C13 C14 C15 N2 -179.8(2) . . . . ?
C11 C10 C15 C14 0.5(4) . . . . ?
S2 C10 C15 C14 179.78(19) . . . . ?
C11 C10 C15 N2 -179.5(2) . . . . ?
S2 C10 C15 N2 -0.2(3) . . . . ?
C1 C9 N2 C15 -179.1(2) . . . . ?
S2 C9 N2 C15 0.4(2) . . . . ?
C1 C9 N2 Al1 4.7(3) . . . . ?
S2 C9 N2 Al1 -175.81(11) . . . . ?
C14 C15 N2 C9 179.9(2) . . . . ?
C10 C15 N2 C9 -0.1(3) . . . . ?
C14 C15 N2 Al1 -4.0(3) . . . . ?
C10 C15 N2 Al1 176.04(16) . . . . ?
C2 N1 Al1 N2 5.7(2) . . . . ?
C8 N1 Al1 N2 -179.10(18) . . . . ?
C2 N1 Al1 C16 124.8(6) . . . . ?
C8 N1 Al1 C16 -60.1(6) . . . . ?
C2 N1 Al1 C16' -108.1(13) . . . . ?
C8 N1 Al1 C16' 67.0(13) . . . . ?
C2 N1 Al1 Cl1' 125.5(4) . . . . ?
C8 N1 Al1 Cl1' -59.3(4) . . . . ?
C2 N1 Al1 Cl1 -108.0(2) . . . . ?
C8 N1 Al1 Cl1 67.1(2) . . . . ?
C9 N2 Al1 N1 -6.2(2) . . . . ?
C15 N2 Al1 N1 178.03(19) . . . . ?
C9 N2 Al1 C16 -125.9(6) . . . . ?
C15 N2 Al1 C16 58.4(6) . . . . ?
C9 N2 Al1 C16' 106.1(11) . . . . ?
C15 N2 Al1 C16' -69.6(11) . . . . ?
C9 N2 Al1 Cl1' -124.1(4) . . . . ?
C15 N2 Al1 Cl1' 60.2(4) . . . . ?
C9 N2 Al1 Cl1 106.4(2) . . . . ?
C15 N2 Al1 Cl1 -69.3(2) . . . . ?

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-2



_database_code_depnum_ccdc_archive 'CCDC 995115'
#######################################################################
#
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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  to carry out CIF format checking respectively.
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data_ddauer_7

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 Ga N2 O2'
_chemical_formula_sum            'C17 H15 Ga N2 O2'
_chemical_formula_weight         349.03

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'
Ga Ga 0.2307 1.6083 '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                   8.386(2)
_cell_length_b                   13.944(3)
_cell_length_c                   13.838(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.60(2)
_cell_angle_gamma                90
_cell_volume                     1542.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9921
_cell_measurement_theta_min      2.548
_cell_measurement_theta_max      26.031

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.089
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.792
_shelx_estimated_absorpt_T_min   0.857
_shelx_estimated_absorpt_T_max   0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7031
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS-2008/2

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'INCOATEC Mo Microsource'
_diffrn_measurement_device_type  'Bruker Smart Apex II Quazar'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46102
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.460
_diffrn_reflns_theta_max         28.321
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7674
_reflns_number_gt                7502
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0369P)²+2.0037P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3495 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.551(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7674
_refine_ls_number_parameters     402
_refine_ls_number_restraints     176
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.016
_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 -0.1625(8) 0.1659(5) 0.4649(5) 0.0176(13) Uani 1 1 d D . . . .
H1 H -0.2444 0.1405 0.4925 0.021 Uiso 1 1 calc R U . . .
C2 C 0.0076(9) 0.1510(5) 0.5147(5) 0.0152(15) Uani 1 1 d D . . . .
O1 O 0.0541(6) 0.1021(4) 0.6047(4) 0.0166(10) Uani 1 1 d D . . . .
C3 C 0.2281(9) 0.0969(5) 0.6329(5) 0.0158(15) Uani 1 1 d D . . . .
C4 C 0.3355(8) 0.0517(5) 0.7147(5) 0.0171(13) Uani 1 1 d D . . . .
H4 H 0.2978 0.0196 0.7642 0.020 Uiso 1 1 calc R U . . .
C5 C 0.5043(8) 0.0562(5) 0.7201(5) 0.0180(13) Uani 1 1 d D . . . .
H5 H 0.5843 0.0253 0.7749 0.022 Uiso 1 1 calc R U . . .
C6 C 0.5596(9) 0.1047(5) 0.6475(6) 0.0183(14) Uani 1 1 d D . . . .
H6 H 0.6759 0.1061 0.6546 0.022 Uiso 1 1 calc R U . . .
C7 C 0.4488(8) 0.1506(5) 0.5656(5) 0.0169(13) Uani 1 1 d D . . . .
H7 H 0.4865 0.1838 0.5167 0.020 Uiso 1 1 calc R U . . .
C8 C 0.2793(8) 0.1459(5) 0.5585(5) 0.0144(14) Uani 1 1 d D . . . .
N1 N 0.1382(7) 0.1792(4) 0.4862(4) 0.0148(12) Uani 1 1 d D . . . .
C9 C -0.2119(7) 0.2181(5) 0.3749(4) 0.0172(12) Uani 1 1 d D . . . .
O2 O -0.3774(5) 0.2378(5) 0.3314(3) 0.0191(9) Uani 1 1 d D . . . .
C10 C -0.3866(9) 0.2904(5) 0.2446(5) 0.0178(15) Uani 1 1 d D . . . .
C11 C -0.5260(9) 0.3254(5) 0.1732(6) 0.0192(15) Uani 1 1 d D . . . .
H11 H -0.6355 0.3161 0.1782 0.023 Uiso 1 1 calc R U . . .
C12 C -0.4974(11) 0.3753(5) 0.0930(6) 0.0230(16) Uani 1 1 d D . . . .
H12 H -0.5892 0.4029 0.0426 0.028 Uiso 1 1 calc R U . . .
C13 C -0.3358(10) 0.3857(5) 0.0854(5) 0.0207(15) Uani 1 1 d D . . . .
H13 H -0.3208 0.4184 0.0285 0.025 Uiso 1 1 calc R U . . .
C14 C -0.1967(9) 0.3495(5) 0.1586(5) 0.0179(13) Uani 1 1 d D . . . .
H14 H -0.0869 0.3578 0.1538 0.021 Uiso 1 1 calc R U . . .
C15 C -0.2259(9) 0.3005(5) 0.2395(5) 0.0151(14) Uani 1 1 d D . . . .
N2 N -0.1168(7) 0.2531(5) 0.3238(4) 0.0175(12) Uani 1 1 d D . . . .
Ga1 Ga 0.13062(8) 0.24129(4) 0.35476(5) 0.01563(15) Uani 1 1 d D . . . .
C16 C 0.2365(10) 0.3684(5) 0.3783(6) 0.0269(14) Uani 1 1 d D . . . .
H16A H 0.1716 0.4134 0.3270 0.040 Uiso 1 1 calc R U . . .
H16B H 0.3506 0.3640 0.3738 0.040 Uiso 1 1 calc R U . . .
H16C H 0.2400 0.3913 0.4459 0.040 Uiso 1 1 calc R U . . .
C17 C 0.1858(10) 0.1420(5) 0.2685(5) 0.0227(14) Uani 1 1 d D . . . .
H17A H 0.1250 0.1549 0.1973 0.034 Uiso 1 1 calc R U . . .
H17B H 0.1536 0.0789 0.2876 0.034 Uiso 1 1 calc R U . . .
H17C H 0.3064 0.1428 0.2779 0.034 Uiso 1 1 calc R U . . .
C18 C 0.5918(8) 0.7903(5) 0.2090(5) 0.0194(15) Uani 1 1 d D . . . .
H18 H 0.5084 0.8156 0.2355 0.023 Uiso 1 1 calc R U . . .
C19 C 0.7592(9) 0.8111(5) 0.2553(5) 0.0171(15) Uani 1 1 d D . . . .
O3 O 0.8016(6) 0.8641(3) 0.3441(4) 0.0197(11) Uani 1 1 d D . . . .
C20 C 0.9756(9) 0.8711(5) 0.3726(6) 0.0170(15) Uani 1 1 d D . . . .
C21 C 1.0792(9) 0.9149(5) 0.4568(5) 0.0196(13) Uani 1 1 d D . . . .
H21 H 1.0376 0.9461 0.5052 0.024 Uiso 1 1 calc R U . . .
C22 C 1.2499(9) 0.9108(5) 0.4671(5) 0.0213(15) Uani 1 1 d D . . . .
H22 H 1.3277 0.9388 0.5249 0.026 Uiso 1 1 calc R U . . .
C23 C 1.3085(9) 0.8662(6) 0.3936(6) 0.0232(16) Uani 1 1 d D . . . .
H23 H 1.4253 0.8659 0.4022 0.028 Uiso 1 1 calc R U . . .
C24 C 1.2006(9) 0.8226(5) 0.3083(5) 0.0206(14) Uani 1 1 d D . . . .
H24 H 1.2402 0.7927 0.2582 0.025 Uiso 1 1 calc R U . . .
C25 C 1.0313(9) 0.8250(5) 0.3005(5) 0.0181(15) Uani 1 1 d D . . . .
N3 N 0.8917(7) 0.7876(5) 0.2275(4) 0.0173(13) Uani 1 1 d D . . . .
C26 C 0.5469(7) 0.7317(5) 0.1231(4) 0.0172(13) Uani 1 1 d D . . . .
O4 O 0.3825(6) 0.7081(5) 0.0832(3) 0.0198(9) Uani 1 1 d D . . . .
C27 C 0.3749(9) 0.6487(5) 0.0004(5) 0.0182(15) Uani 1 1 d D . . . .
C28 C 0.2367(10) 0.6064(6) -0.0660(6) 0.0236(17) Uani 1 1 d D . . . .
H28 H 0.1278 0.6133 -0.0593 0.028 Uiso 1 1 calc R U . . .
C29 C 0.2672(10) 0.5527(5) -0.1439(6) 0.0252(16) Uani 1 1 d D . . . .
H29 H 0.1769 0.5202 -0.1908 0.030 Uiso 1 1 calc R U . . .
C30 C 0.4280(8) 0.5458(5) -0.1545(6) 0.0227(15) Uani 1 1 d D . . . .
H30 H 0.4436 0.5108 -0.2098 0.027 Uiso 1 1 calc R U . . .
C31 C 0.5651(9) 0.5892(5) -0.0856(5) 0.0193(14) Uani 1 1 d D . . . .
H31 H 0.6746 0.5832 -0.0916 0.023 Uiso 1 1 calc R U . . .
C32 C 0.5348(9) 0.6414(5) -0.0079(5) 0.0167(14) Uani 1 1 d D . . . .
N4 N 0.6434(6) 0.6947(4) 0.0720(4) 0.0139(11) Uani 1 1 d D . . . .
Ga2 Ga 0.88892(9) 0.71350(4) 0.10315(5) 0.01590(15) Uani 1 1 d D . . . .
C33 C 0.9471(10) 0.8039(5) 0.0099(5) 0.0232(14) Uani 1 1 d D . . . .
H33A H 0.9195 0.7754 -0.0579 0.035 Uiso 1 1 calc R U . . .
H33B H 1.0672 0.8180 0.0344 0.035 Uiso 1 1 calc R U . . .
H33C H 0.8837 0.8635 0.0067 0.035 Uiso 1 1 calc R U . . .
C34 C 1.0057(9) 0.5899(4) 0.1383(5) 0.0213(12) Uani 1 1 d D . . . .
H34A H 0.9609 0.5441 0.0831 0.032 Uiso 1 1 calc R U . . .
H34B H 0.9887 0.5651 0.2007 0.032 Uiso 1 1 calc R U . . .
H34C H 1.1256 0.5991 0.1487 0.032 Uiso 1 1 calc R 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 C9 1.393(8) . ?
C1 C2 1.399(9) . ?
C1 H1 0.9500 . ?
C2 N1 1.331(9) . ?
C2 O1 1.369(8) . ?
O1 C3 1.394(8) . ?
C3 C4 1.368(9) . ?
C3 C8 1.406(9) . ?
C4 C5 1.396(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(9) . ?
C7 H7 0.9500 . ?
C8 N1 1.379(8) . ?
N1 Ga1 1.998(5) . ?
C9 N2 1.310(7) . ?
C9 O2 1.363(7) . ?
O2 C10 1.389(8) . ?
C10 C11 1.372(9) . ?
C10 C15 1.378(10) . ?
C11 C12 1.391(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.398(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(9) . ?
C14 H14 0.9500 . ?
C15 N2 1.411(8) . ?
N2 Ga1 1.994(5) . ?
Ga1 C16 1.965(7) . ?
Ga1 C17 1.972(7) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.386(9) . ?
C18 C26 1.397(8) . ?
C18 H18 0.9500 . ?
C19 N3 1.322(9) . ?
C19 O3 1.386(8) . ?
O3 C20 1.395(8) . ?
C20 C21 1.368(9) . ?
C20 C25 1.382(9) . ?
C21 C22 1.396(9) . ?
C21 H21 0.9500 . ?
C22 C23 1.402(9) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(9) . ?
C23 H23 0.9500 . ?
C24 C25 1.391(9) . ?
C24 H24 0.9500 . ?
C25 N3 1.396(9) . ?
N3 Ga2 2.001(6) . ?
C26 N4 1.328(7) . ?
C26 O4 1.362(7) . ?
O4 C27 1.400(8) . ?
C27 C28 1.375(10) . ?
C27 C32 1.383(9) . ?
C28 C29 1.399(10) . ?
C28 H28 0.9500 . ?
C29 C30 1.403(11) . ?
C29 H29 0.9500 . ?
C30 C31 1.390(9) . ?
C30 H30 0.9500 . ?
C31 C32 1.384(9) . ?
C31 H31 0.9500 . ?
C32 N4 1.413(8) . ?
N4 Ga2 1.990(5) . ?
Ga2 C33 1.968(7) . ?
Ga2 C34 1.969(6) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?

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
C9 C1 C2 120.1(6) . . ?
C9 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
N1 C2 O1 112.5(6) . . ?
N1 C2 C1 128.2(6) . . ?
O1 C2 C1 119.3(6) . . ?
C2 O1 C3 105.4(5) . . ?
C4 C3 O1 128.8(6) . . ?
C4 C3 C8 124.0(7) . . ?
O1 C3 C8 107.2(6) . . ?
C3 C4 C5 115.3(7) . . ?
C3 C4 H4 122.4 . . ?
C5 C4 H4 122.4 . . ?
C4 C5 C6 122.2(6) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C7 C6 C5 121.6(6) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 116.9(6) . . ?
C6 C7 H7 121.5 . . ?
C8 C7 H7 121.5 . . ?
N1 C8 C7 131.9(6) . . ?
N1 C8 C3 108.0(6) . . ?
C7 C8 C3 120.0(6) . . ?
C2 N1 C8 106.8(5) . . ?
C2 N1 Ga1 126.5(4) . . ?
C8 N1 Ga1 126.2(4) . . ?
N2 C9 O2 113.1(5) . . ?
N2 C9 C1 127.8(6) . . ?
O2 C9 C1 119.2(6) . . ?
C9 O2 C10 105.7(5) . . ?
C11 C10 C15 124.0(7) . . ?
C11 C10 O2 128.5(7) . . ?
C15 C10 O2 107.4(6) . . ?
C10 C11 C12 115.9(7) . . ?
C10 C11 H11 122.0 . . ?
C12 C11 H11 122.0 . . ?
C11 C12 C13 121.2(7) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 121.8(7) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 116.8(7) . . ?
C13 C14 H14 121.6 . . ?
C15 C14 H14 121.6 . . ?
C10 C15 C14 120.2(7) . . ?
C10 C15 N2 108.0(6) . . ?
C14 C15 N2 131.8(7) . . ?
C9 N2 C15 105.8(5) . . ?
C9 N2 Ga1 128.1(5) . . ?
C15 N2 Ga1 126.1(5) . . ?
C16 Ga1 C17 123.8(3) . . ?
C16 Ga1 N2 110.5(3) . . ?
C17 Ga1 N2 110.3(3) . . ?
C16 Ga1 N1 110.6(3) . . ?
C17 Ga1 N1 107.4(3) . . ?
N2 Ga1 N1 88.6(2) . . ?
Ga1 C16 H16A 109.5 . . ?
Ga1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Ga1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Ga1 C17 H17A 109.5 . . ?
Ga1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Ga1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C26 119.3(6) . . ?
C19 C18 H18 120.3 . . ?
C26 C18 H18 120.3 . . ?
N3 C19 O3 112.2(6) . . ?
N3 C19 C18 129.5(6) . . ?
O3 C19 C18 118.3(6) . . ?
C19 O3 C20 104.7(5) . . ?
C21 C20 C25 123.8(7) . . ?
C21 C20 O3 127.8(7) . . ?
C25 C20 O3 108.5(6) . . ?
C20 C21 C22 115.9(7) . . ?
C20 C21 H21 122.1 . . ?
C22 C21 H21 122.1 . . ?
C21 C22 C23 121.2(7) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C24 C23 C22 121.9(7) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C25 C24 C23 116.2(7) . . ?
C25 C24 H24 121.9 . . ?
C23 C24 H24 121.9 . . ?
C20 C25 C24 121.0(7) . . ?
C20 C25 N3 107.7(6) . . ?
C24 C25 N3 131.3(7) . . ?
C19 N3 C25 107.0(6) . . ?
C19 N3 Ga2 125.9(5) . . ?
C25 N3 Ga2 127.2(5) . . ?
N4 C26 O4 113.3(5) . . ?
N4 C26 C18 129.0(6) . . ?
O4 C26 C18 117.7(5) . . ?
C26 O4 C27 105.3(5) . . ?
C28 C27 C32 123.7(7) . . ?
C28 C27 O4 128.4(7) . . ?
C32 C27 O4 107.8(6) . . ?
C27 C28 C29 115.5(7) . . ?
C27 C28 H28 122.2 . . ?
C29 C28 H28 122.2 . . ?
C28 C29 C30 121.5(7) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 H29 119.3 . . ?
C31 C30 C29 121.4(7) . . ?
C31 C30 H30 119.3 . . ?
C29 C30 H30 119.3 . . ?
C32 C31 C30 116.9(7) . . ?
C32 C31 H31 121.5 . . ?
C30 C31 H31 121.5 . . ?
C27 C32 C31 120.9(7) . . ?
C27 C32 N4 107.9(6) . . ?
C31 C32 N4 131.2(7) . . ?
C26 N4 C32 105.6(5) . . ?
C26 N4 Ga2 126.2(5) . . ?
C32 N4 Ga2 128.2(5) . . ?
C33 Ga2 C34 121.3(3) . . ?
C33 Ga2 N4 112.8(3) . . ?
C34 Ga2 N4 110.1(3) . . ?
C33 Ga2 N3 107.0(3) . . ?
C34 Ga2 N3 111.3(3) . . ?
N4 Ga2 N3 89.8(2) . . ?
Ga2 C33 H33A 109.5 . . ?
Ga2 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
Ga2 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
Ga2 C34 H34A 109.5 . . ?
Ga2 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
Ga2 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

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
C9 C1 C2 N1 -1.5(12) . . . . ?
C9 C1 C2 O1 178.0(6) . . . . ?
N1 C2 O1 C3 -2.1(8) . . . . ?
C1 C2 O1 C3 178.4(7) . . . . ?
C2 O1 C3 C4 -176.8(7) . . . . ?
C2 O1 C3 C8 1.5(8) . . . . ?
O1 C3 C4 C5 177.5(7) . . . . ?
C8 C3 C4 C5 -0.6(11) . . . . ?
C3 C4 C5 C6 0.8(11) . . . . ?
C4 C5 C6 C7 -0.3(12) . . . . ?
C5 C6 C7 C8 -0.4(11) . . . . ?
C6 C7 C8 N1 -176.9(7) . . . . ?
C6 C7 C8 C3 0.6(10) . . . . ?
C4 C3 C8 N1 177.9(7) . . . . ?
O1 C3 C8 N1 -0.5(8) . . . . ?
C4 C3 C8 C7 -0.1(11) . . . . ?
O1 C3 C8 C7 -178.6(6) . . . . ?
O1 C2 N1 C8 1.8(8) . . . . ?
C1 C2 N1 C8 -178.7(7) . . . . ?
O1 C2 N1 Ga1 173.7(5) . . . . ?
C1 C2 N1 Ga1 -6.8(12) . . . . ?
C7 C8 N1 C2 177.0(8) . . . . ?
C3 C8 N1 C2 -0.7(8) . . . . ?
C7 C8 N1 Ga1 5.0(11) . . . . ?
C3 C8 N1 Ga1 -172.7(5) . . . . ?
C2 C1 C9 N2 4.3(11) . . . . ?
C2 C1 C9 O2 -175.4(7) . . . . ?
N2 C9 O2 C10 -0.1(8) . . . . ?
C1 C9 O2 C10 179.6(6) . . . . ?
C9 O2 C10 C11 178.3(8) . . . . ?
C9 O2 C10 C15 -0.2(8) . . . . ?
C15 C10 C11 C12 -1.3(12) . . . . ?
O2 C10 C11 C12 -179.5(7) . . . . ?
C10 C11 C12 C13 2.0(11) . . . . ?
C11 C12 C13 C14 -2.1(12) . . . . ?
C12 C13 C14 C15 1.2(11) . . . . ?
C11 C10 C15 C14 0.6(13) . . . . ?
O2 C10 C15 C14 179.1(6) . . . . ?
C11 C10 C15 N2 -178.2(7) . . . . ?
O2 C10 C15 N2 0.4(9) . . . . ?
C13 C14 C15 C10 -0.5(11) . . . . ?
C13 C14 C15 N2 177.9(7) . . . . ?
O2 C9 N2 C15 0.3(8) . . . . ?
C1 C9 N2 C15 -179.4(7) . . . . ?
O2 C9 N2 Ga1 -178.7(5) . . . . ?
C1 C9 N2 Ga1 1.7(11) . . . . ?
C10 C15 N2 C9 -0.4(8) . . . . ?
C14 C15 N2 C9 -178.9(8) . . . . ?
C10 C15 N2 Ga1 178.6(5) . . . . ?
C14 C15 N2 Ga1 0.1(12) . . . . ?
C26 C18 C19 N3 4.1(12) . . . . ?
C26 C18 C19 O3 -175.9(6) . . . . ?
N3 C19 O3 C20 -1.2(8) . . . . ?
C18 C19 O3 C20 178.8(7) . . . . ?
C19 O3 C20 C21 -178.4(7) . . . . ?
C19 O3 C20 C25 1.3(8) . . . . ?
C25 C20 C21 C22 0.0(12) . . . . ?
O3 C20 C21 C22 179.7(7) . . . . ?
C20 C21 C22 C23 1.4(12) . . . . ?
C21 C22 C23 C24 -1.2(13) . . . . ?
C22 C23 C24 C25 -0.4(12) . . . . ?
C21 C20 C25 C24 -1.7(13) . . . . ?
O3 C20 C25 C24 178.5(7) . . . . ?
C21 C20 C25 N3 178.8(7) . . . . ?
O3 C20 C25 N3 -1.0(9) . . . . ?
C23 C24 C25 C20 1.8(12) . . . . ?
C23 C24 C25 N3 -178.7(7) . . . . ?
O3 C19 N3 C25 0.6(8) . . . . ?
C18 C19 N3 C25 -179.4(8) . . . . ?
O3 C19 N3 Ga2 -178.9(4) . . . . ?
C18 C19 N3 Ga2 1.2(12) . . . . ?
C20 C25 N3 C19 0.3(9) . . . . ?
C24 C25 N3 C19 -179.2(9) . . . . ?
C20 C25 N3 Ga2 179.7(5) . . . . ?
C24 C25 N3 Ga2 0.2(13) . . . . ?
C19 C18 C26 N4 -4.3(11) . . . . ?
C19 C18 C26 O4 176.1(7) . . . . ?
N4 C26 O4 C27 1.4(8) . . . . ?
C18 C26 O4 C27 -179.0(6) . . . . ?
C26 O4 C27 C28 -179.2(8) . . . . ?
C26 O4 C27 C32 -1.8(9) . . . . ?
C32 C27 C28 C29 1.1(12) . . . . ?
O4 C27 C28 C29 178.1(7) . . . . ?
C27 C28 C29 C30 -2.0(12) . . . . ?
C28 C29 C30 C31 2.4(12) . . . . ?
C29 C30 C31 C32 -1.7(11) . . . . ?
C28 C27 C32 C31 -0.4(13) . . . . ?
O4 C27 C32 C31 -178.0(6) . . . . ?
C28 C27 C32 N4 179.1(7) . . . . ?
O4 C27 C32 N4 1.6(9) . . . . ?
C30 C31 C32 C27 0.7(11) . . . . ?
C30 C31 C32 N4 -178.8(7) . . . . ?
O4 C26 N4 C32 -0.4(8) . . . . ?
C18 C26 N4 C32 180.0(7) . . . . ?
O4 C26 N4 Ga2 178.8(5) . . . . ?
C18 C26 N4 Ga2 -0.8(11) . . . . ?
C27 C32 N4 C26 -0.8(8) . . . . ?
C31 C32 N4 C26 178.8(8) . . . . ?
C27 C32 N4 Ga2 -180.0(5) . . . . ?
C31 C32 N4 Ga2 -0.5(11) . . . . ?

_refine_diff_density_max         1.298
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.064

_shelxl_version_number           2013-2



_database_code_depnum_ccdc_archive 'CCDC 995116'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ddauer_8

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 Ga N2 S2'
_chemical_formula_sum            'C17 H15 Ga N2 S2'
_chemical_formula_weight         381.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.0826 0.0763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga 0.3179 1.0589 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   15.446(3)
_cell_length_b                   15.177(3)
_cell_length_c                   6.929(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1624.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      2.335
_cell_measurement_theta_max      23.647

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    1.023
_shelx_estimated_absorpt_T_min   0.673
_shelx_estimated_absorpt_T_max   0.777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6769
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_process_details   SADABS-2008/2

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.56086
_diffrn_radiation_type           AgK\a
_diffrn_source                   'INCOATEC Ag Microsource'
_diffrn_measurement_device_type  'Bruker Smart Apex II with D8-Goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40129
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.081
_diffrn_reflns_theta_max         23.681
_diffrn_reflns_theta_full        19.665
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2580
_reflns_number_gt                2463
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0070P)²+2.2382P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2580
_refine_ls_number_parameters     108
_refine_ls_number_restraints     103
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0602
_refine_ls_wR_factor_gt          0.0596
_refine_ls_goodness_of_fit_ref   1.268
_refine_ls_restrained_S_all      1.245
_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
Ga1 Ga 0.32913(2) 0.7500 0.44953(3) 0.00983(6) Uani 1 2 d DS TU P . .
C1 C 0.49487(14) 0.7500 0.7591(3) 0.0147(4) Uani 1 2 d S TU P . .
H1 H 0.5466 0.7500 0.8333 0.018 Uiso 1 2 calc R U P . .
S1 S 0.50162(3) 0.57195(3) 0.80688(6) 0.01752(9) Uani 1 1 d . U . . .
N1 N 0.39173(8) 0.65468(8) 0.59023(18) 0.0122(2) Uani 1 1 d . U . . .
C2 C 0.45934(9) 0.66907(10) 0.7081(2) 0.0125(3) Uani 1 1 d . U . . .
C3 C 0.42500(11) 0.50973(11) 0.6830(2) 0.0164(3) Uani 1 1 d . U . . .
C4 C 0.41384(12) 0.41881(11) 0.6820(3) 0.0219(3) Uani 1 1 d . U . . .
H4 H 0.4508 0.3815 0.7550 0.026 Uiso 1 1 calc R U . . .
C5 C 0.34733(13) 0.38425(11) 0.5717(3) 0.0247(4) Uani 1 1 d . U . . .
H5 H 0.3382 0.3224 0.5697 0.030 Uiso 1 1 calc R U . . .
C9 C 0.20776(14) 0.7500 0.5365(3) 0.0154(4) Uani 1 2 d DS TU P . .
H9A H 0.1728 0.7857 0.4481 0.023 Uiso 0.5 1 calc R U P . .
H9B H 0.2043 0.7748 0.6668 0.023 Uiso 0.5 1 calc R U P . .
H9C H 0.1857 0.6894 0.5378 0.023 Uiso 0.5 1 calc R U P . .
C8 C 0.37174(10) 0.56543(10) 0.5739(2) 0.0138(3) Uani 1 1 d . U . . .
C7 C 0.30521(11) 0.52969(11) 0.4623(2) 0.0176(3) Uani 1 1 d . U . . .
H7 H 0.2687 0.5667 0.3873 0.021 Uiso 1 1 calc R U . . .
C6 C 0.29339(12) 0.43906(11) 0.4630(3) 0.0216(3) Uani 1 1 d . U . . .
H6 H 0.2480 0.4139 0.3887 0.026 Uiso 1 1 calc R U . . .
C10 C 0.36790(16) 0.7500 0.1796(3) 0.0186(4) Uani 1 2 d DS TU P . .
H10A H 0.3313 0.7101 0.1040 0.028 Uiso 0.5 1 calc R U P . .
H10B H 0.4282 0.7301 0.1731 0.028 Uiso 0.5 1 calc R U P . .
H10C H 0.3635 0.8098 0.1269 0.028 Uiso 0.5 1 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ga1 C10 1.964(2) . ?
Ga1 C9 1.969(2) . ?
Ga1 N1 1.9945(13) 7_575 ?
Ga1 N1 1.9945(13) . ?
C1 C2 1.3909(19) . ?
C1 C2 1.3909(19) 7_575 ?
C1 H1 0.9500 . ?
S1 C3 1.7404(18) . ?
S1 C2 1.7514(16) . ?
N1 C2 1.3436(19) . ?
N1 C8 1.3938(19) . ?
C3 C4 1.391(2) . ?
C3 C8 1.401(2) . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 C7 1.396(2) . ?
C7 C6 1.388(2) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
C10 Ga1 C9 125.57(10) . . ?
C10 Ga1 N1 108.52(6) . 7_575 ?
C9 Ga1 N1 108.18(6) . 7_575 ?
C10 Ga1 N1 108.52(6) . . ?
C9 Ga1 N1 108.18(6) . . ?
N1 Ga1 N1 92.99(8) 7_575 . ?
C2 C1 C2 124.0(2) . 7_575 ?
C2 C1 H1 118.0 . . ?
C2 C1 H1 118.0 7_575 . ?
C3 S1 C2 90.60(8) . . ?
C2 N1 C8 112.29(13) . . ?
C2 N1 Ga1 123.78(11) . . ?
C8 N1 Ga1 123.92(10) . . ?
N1 C2 C1 127.20(15) . . ?
N1 C2 S1 112.99(11) . . ?
C1 C2 S1 119.78(12) . . ?
C4 C3 C8 121.55(16) . . ?
C4 C3 S1 128.70(14) . . ?
C8 C3 S1 109.75(12) . . ?
C5 C4 C3 118.08(16) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C4 C5 C6 120.98(16) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
Ga1 C9 H9A 109.5 . . ?
Ga1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Ga1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C8 C7 125.84(14) . . ?
N1 C8 C3 114.38(14) . . ?
C7 C8 C3 119.79(15) . . ?
C6 C7 C8 118.69(16) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C7 C6 C5 120.90(17) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
Ga1 C10 H10A 109.5 . . ?
Ga1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
Ga1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
C8 N1 C2 C1 -178.60(17) . . . . ?
Ga1 N1 C2 C1 2.9(2) . . . . ?
C8 N1 C2 S1 -0.36(16) . . . . ?
Ga1 N1 C2 S1 -178.90(7) . . . . ?
C2 C1 C2 N1 6.5(3) 7_575 . . . ?
C2 C1 C2 S1 -171.60(13) 7_575 . . . ?
C3 S1 C2 N1 0.19(12) . . . . ?
C3 S1 C2 C1 178.58(15) . . . . ?
C2 S1 C3 C4 179.46(17) . . . . ?
C2 S1 C3 C8 0.02(12) . . . . ?
C8 C3 C4 C5 -0.9(3) . . . . ?
S1 C3 C4 C5 179.70(14) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C2 N1 C8 C7 -179.91(15) . . . . ?
Ga1 N1 C8 C7 -1.4(2) . . . . ?
C2 N1 C8 C3 0.38(19) . . . . ?
Ga1 N1 C8 C3 178.93(10) . . . . ?
C4 C3 C8 N1 -179.72(15) . . . . ?
S1 C3 C8 N1 -0.23(17) . . . . ?
C4 C3 C8 C7 0.6(2) . . . . ?
S1 C3 C8 C7 -179.96(12) . . . . ?
N1 C8 C7 C6 -179.48(16) . . . . ?
C3 C8 C7 C6 0.2(2) . . . . ?
C8 C7 C6 C5 -0.6(3) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-2



_database_code_depnum_ccdc_archive 'CCDC 995117'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ddauer_9

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H19 N3 O3'
_chemical_formula_sum            'C25 H19 N3 O3'
_chemical_formula_weight         409.43

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   31.997(3)
_cell_length_b                   8.9070(10)
_cell_length_c                   15.673(2)
_cell_angle_alpha                90
_cell_angle_beta                 117.530(10)
_cell_angle_gamma                90
_cell_volume                     3961.0(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6559
_cell_measurement_theta_min      2.397
_cell_measurement_theta_max      27.080

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             1712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9216
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_process_details   SADABS-2008/2

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'INCOATEC Mo Microsource'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Bruker Smart Apex II with D8-Goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19537
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.435
_diffrn_reflns_theta_max         27.122
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4360
_reflns_number_gt                3662
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0338P)²+3.5528P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00067(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4360
_refine_ls_number_parameters     358
_refine_ls_number_restraints     594
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      0.985
_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
C22 C 0.39204(4) 0.81591(13) 0.54273(9) 0.0189(2) Uani 1 1 d D . . . .
O1 O 0.4619(3) 0.8244(11) 0.5173(8) 0.0231(10) Uani 0.629(8) 1 d D U P A 1
N1 N 0.4127(4) 0.6328(12) 0.4438(9) 0.0198(10) Uani 0.629(8) 1 d D U P A 1
C1 C 0.4215(4) 0.7473(16) 0.4994(12) 0.0197(6) Uani 0.629(8) 1 d D U P A 1
C2 C 0.4507(2) 0.6254(9) 0.4223(7) 0.0209(10) Uani 0.629(8) 1 d D U P A 1
C3 C 0.46106(17) 0.5196(5) 0.3689(3) 0.0258(9) Uani 0.629(8) 1 d D U P A 1
H3 H 0.4411 0.4364 0.3388 0.031 Uiso 0.629(8) 1 calc R U P A 1
C4 C 0.50232(18) 0.5438(5) 0.3627(3) 0.0260(9) Uani 0.629(8) 1 d D U P A 1
H4 H 0.5111 0.4743 0.3278 0.031 Uiso 0.629(8) 1 calc R U P A 1
C5 C 0.53147(15) 0.6675(5) 0.4061(3) 0.0264(8) Uani 0.629(8) 1 d D U P A 1
H5 H 0.5590 0.6810 0.3984 0.032 Uiso 0.629(8) 1 calc R U P A 1
C6 C 0.52142(18) 0.7707(6) 0.4600(4) 0.0230(8) Uani 0.629(8) 1 d D U P A 1
H6 H 0.5413 0.8542 0.4902 0.028 Uiso 0.629(8) 1 calc R U P A 1
C7 C 0.4807(2) 0.7441(8) 0.4669(6) 0.0208(10) Uani 0.629(8) 1 d D U P A 1
O1' O 0.4080(5) 0.6316(18) 0.4484(13) 0.0215(15) Uani 0.371(8) 1 d D U P A 2
N1' N 0.4631(6) 0.816(2) 0.5151(15) 0.0198(18) Uani 0.371(8) 1 d D U P A 2
C1' C 0.4242(7) 0.757(3) 0.505(2) 0.0197(6) Uani 0.371(8) 1 d D U P A 2
C2' C 0.4757(4) 0.7225(15) 0.4594(10) 0.0191(14) Uani 0.371(8) 1 d D U P A 2
C3' C 0.5152(3) 0.7334(10) 0.4429(7) 0.0269(15) Uani 0.371(8) 1 d D U P A 2
H3' H 0.5378 0.8116 0.4696 0.032 Uiso 0.371(8) 1 calc R U P A 2
C4' C 0.5190(3) 0.6223(9) 0.3854(5) 0.0253(13) Uani 0.371(8) 1 d D U P A 2
H4' H 0.5452 0.6220 0.3724 0.030 Uiso 0.371(8) 1 calc R U P A 2
C5' C 0.4849(3) 0.5107(8) 0.3462(5) 0.0276(13) Uani 0.371(8) 1 d D U P A 2
H5' H 0.4887 0.4367 0.3067 0.033 Uiso 0.371(8) 1 calc R U P A 2
C6' C 0.4459(3) 0.5020(9) 0.3617(6) 0.0266(13) Uani 0.371(8) 1 d D U P A 2
H6' H 0.4228 0.4253 0.3340 0.032 Uiso 0.371(8) 1 calc R U P A 2
C7' C 0.4426(4) 0.6114(15) 0.4199(11) 0.0181(15) Uani 0.371(8) 1 d D U P A 2
O2 O 0.38472(3) 0.57596(10) 0.60551(6) 0.0224(2) Uani 1 1 d D . . . .
N2 N 0.31562(4) 0.69387(11) 0.51517(7) 0.0201(2) Uani 1 1 d D . . . .
O3 O 0.33131(3) 0.90691(9) 0.38503(6) 0.02064(19) Uani 1 1 d D . . . .
N3 N 0.37546(4) 1.08305(11) 0.49234(7) 0.0208(2) Uani 1 1 d D . . . .
C8 C 0.36053(4) 0.69510(13) 0.54841(9) 0.0191(2) Uani 1 1 d D . . . .
C9 C 0.30689(4) 0.55957(14) 0.55201(9) 0.0202(3) Uani 1 1 d D . . . .
C13 C 0.35419(5) 0.35569(15) 0.65622(10) 0.0276(3) Uani 1 1 d D . . . .
H13 H 0.3839 0.3091 0.6933 0.033 Uiso 1 1 calc R U . . .
C10 C 0.26498(4) 0.49695(15) 0.54268(9) 0.0243(3) Uani 1 1 d D . . . .
H10 H 0.2353 0.5433 0.5048 0.029 Uiso 1 1 calc R U . . .
C12 C 0.31244(5) 0.29482(15) 0.64709(10) 0.0292(3) Uani 1 1 d D . . . .
H12 H 0.3134 0.2037 0.6795 0.035 Uiso 1 1 calc R U . . .
C11 C 0.26887(5) 0.36373(15) 0.59145(10) 0.0277(3) Uani 1 1 d D . . . .
H11 H 0.2411 0.3178 0.5870 0.033 Uiso 1 1 calc R U . . .
C15 C 0.36504(4) 0.94275(14) 0.47575(9) 0.0190(2) Uani 1 1 d D . . . .
C14 C 0.34946(4) 0.48869(14) 0.60765(9) 0.0212(3) Uani 1 1 d D . . . .
C16 C 0.34621(4) 1.15341(14) 0.40458(9) 0.0202(3) Uani 1 1 d D . . . .
C20 C 0.28582(4) 1.07645(15) 0.24578(9) 0.0227(3) Uani 1 1 d D . . . .
H20 H 0.2671 1.0004 0.2026 0.027 Uiso 1 1 calc R U . . .
C17 C 0.34220(5) 1.30390(14) 0.37760(10) 0.0249(3) Uani 1 1 d D . . . .
H17 H 0.3608 1.3797 0.4214 0.030 Uiso 1 1 calc R U . . .
C19 C 0.28175(5) 1.22635(15) 0.21946(10) 0.0254(3) Uani 1 1 d D . . . .
H19 H 0.2594 1.2545 0.1562 0.030 Uiso 1 1 calc R U . . .
C18 C 0.30982(5) 1.33752(15) 0.28383(10) 0.0262(3) Uani 1 1 d D . . . .
H18 H 0.3065 1.4387 0.2625 0.031 Uiso 1 1 calc R U . . .
C21 C 0.31901(4) 1.04504(13) 0.33914(9) 0.0191(2) Uani 1 1 d D . . . .
C23 C 0.42317(4) 0.87802(14) 0.64534(9) 0.0215(3) Uani 1 1 d . . . . .
H23A H 0.4458 0.7994 0.6843 0.026 Uiso 1 1 calc R U . . .
H23B H 0.4415 0.9645 0.6410 0.026 Uiso 1 1 calc R U . . .
C24 C 0.39487(5) 0.92794(15) 0.69655(9) 0.0256(3) Uani 1 1 d . . . . .
H24A H 0.3699 0.9988 0.6549 0.031 Uiso 1 1 calc R U . . .
H24B H 0.3794 0.8395 0.7081 0.031 Uiso 1 1 calc R U . . .
C25 C 0.42632(5) 1.00356(18) 0.79192(10) 0.0352(3) Uani 1 1 d . . . . .
H25A H 0.4071 1.0377 0.8220 0.053 Uiso 1 1 calc R U . . .
H25B H 0.4421 1.0899 0.7807 0.053 Uiso 1 1 calc R U . . .
H25C H 0.4500 0.9318 0.8346 0.053 Uiso 1 1 calc R 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
C22 C1' 1.501(10) . ?
C22 C8 1.5051(16) . ?
C22 C15 1.5120(16) . ?
C22 C1 1.521(6) . ?
C22 C23 1.5504(17) . ?
O1 C1 1.375(8) . ?
O1 C7 1.391(7) . ?
N1 C1 1.285(8) . ?
N1 C2 1.405(8) . ?
C2 C7 1.381(6) . ?
C2 C3 1.398(6) . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(6) . ?
C6 H6 0.9500 . ?
O1' C1' 1.368(13) . ?
O1' C7' 1.382(11) . ?
N1' C1' 1.289(13) . ?
N1' C2' 1.394(12) . ?
C2' C7' 1.371(9) . ?
C2' C3' 1.407(10) . ?
C3' C4' 1.381(8) . ?
C3' H3' 0.9500 . ?
C4' C5' 1.391(7) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.380(7) . ?
C5' H5' 0.9500 . ?
C6' C7' 1.372(10) . ?
C6' H6' 0.9500 . ?
O2 C8 1.3732(14) . ?
O2 C14 1.3830(14) . ?
N2 C8 1.2824(16) . ?
N2 C9 1.4112(15) . ?
O3 C15 1.3674(15) . ?
O3 C21 1.3872(14) . ?
N3 C15 1.2886(16) . ?
N3 C16 1.4039(16) . ?
C9 C14 1.3845(18) . ?
C9 C10 1.3962(17) . ?
C13 C14 1.3781(18) . ?
C13 C12 1.3865(19) . ?
C13 H13 0.9500 . ?
C10 C11 1.3855(19) . ?
C10 H10 0.9500 . ?
C12 C11 1.399(2) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C16 C21 1.3842(17) . ?
C16 C17 1.3935(17) . ?
C20 C21 1.3822(17) . ?
C20 C19 1.3857(18) . ?
C20 H20 0.9500 . ?
C17 C18 1.3839(19) . ?
C17 H17 0.9500 . ?
C19 C18 1.4025(19) . ?
C19 H19 0.9500 . ?
C18 H18 0.9500 . ?
C23 C24 1.5276(18) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.5199(19) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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
C1' C22 C8 111.9(8) . . ?
C1' C22 C15 105.3(14) . . ?
C8 C22 C15 113.07(10) . . ?
C8 C22 C1 108.0(5) . . ?
C15 C22 C1 105.3(8) . . ?
C1' C22 C23 107.8(9) . . ?
C8 C22 C23 108.69(10) . . ?
C15 C22 C23 109.91(10) . . ?
C1 C22 C23 111.9(5) . . ?
C1 O1 C7 103.8(6) . . ?
C1 N1 C2 104.9(6) . . ?
N1 C1 O1 115.2(6) . . ?
N1 C1 C22 129.4(7) . . ?
O1 C1 C22 115.2(6) . . ?
C7 C2 C3 121.1(5) . . ?
C7 C2 N1 108.6(6) . . ?
C3 C2 N1 130.3(6) . . ?
C4 C3 C2 115.8(4) . . ?
C4 C3 H3 122.1 . . ?
C2 C3 H3 122.1 . . ?
C3 C4 C5 122.0(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 122.0(3) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C7 C6 C5 115.4(4) . . ?
C7 C6 H6 122.3 . . ?
C5 C6 H6 122.3 . . ?
C6 C7 C2 123.6(5) . . ?
C6 C7 O1 129.0(5) . . ?
C2 C7 O1 107.5(6) . . ?
C1' O1' C7' 101.2(9) . . ?
C1' N1' C2' 102.7(11) . . ?
N1' C1' O1' 117.9(10) . . ?
N1' C1' C22 127.3(12) . . ?
O1' C1' C22 114.7(11) . . ?
C7' C2' N1' 109.1(10) . . ?
C7' C2' C3' 122.7(9) . . ?
N1' C2' C3' 128.3(9) . . ?
C4' C3' C2' 115.3(7) . . ?
C4' C3' H3' 122.3 . . ?
C2' C3' H3' 122.3 . . ?
C3' C4' C5' 120.9(6) . . ?
C3' C4' H4' 119.6 . . ?
C5' C4' H4' 119.6 . . ?
C6' C5' C4' 123.5(6) . . ?
C6' C5' H5' 118.3 . . ?
C4' C5' H5' 118.3 . . ?
C7' C6' C5' 115.5(7) . . ?
C7' C6' H6' 122.2 . . ?
C5' C6' H6' 122.2 . . ?
C2' C7' C6' 122.2(9) . . ?
C2' C7' O1' 109.0(9) . . ?
C6' C7' O1' 128.8(9) . . ?
C8 O2 C14 103.29(9) . . ?
C8 N2 C9 103.75(10) . . ?
C15 O3 C21 103.33(9) . . ?
C15 N3 C16 104.01(10) . . ?
N2 C8 O2 116.51(11) . . ?
N2 C8 C22 129.61(11) . . ?
O2 C8 C22 113.57(10) . . ?
C14 C9 C10 120.11(12) . . ?
C14 C9 N2 108.72(10) . . ?
C10 C9 N2 131.14(12) . . ?
C14 C13 C12 115.12(13) . . ?
C14 C13 H13 122.4 . . ?
C12 C13 H13 122.4 . . ?
C11 C10 C9 116.57(12) . . ?
C11 C10 H10 121.7 . . ?
C9 C10 H10 121.7 . . ?
C13 C12 C11 121.86(13) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C10 C11 C12 121.95(12) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
N3 C15 O3 116.26(11) . . ?
N3 C15 C22 124.95(11) . . ?
O3 C15 C22 118.07(10) . . ?
C13 C14 O2 127.88(12) . . ?
C13 C14 C9 124.38(12) . . ?
O2 C14 C9 107.73(10) . . ?
C21 C16 C17 120.52(12) . . ?
C21 C16 N3 108.71(10) . . ?
C17 C16 N3 130.76(12) . . ?
C21 C20 C19 115.51(12) . . ?
C21 C20 H20 122.2 . . ?
C19 C20 H20 122.2 . . ?
C18 C17 C16 116.68(12) . . ?
C18 C17 H17 121.7 . . ?
C16 C17 H17 121.7 . . ?
C20 C19 C18 121.69(12) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C17 C18 C19 121.82(12) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C20 C21 C16 123.75(11) . . ?
C20 C21 O3 128.57(11) . . ?
C16 C21 O3 107.69(10) . . ?
C24 C23 C22 113.34(10) . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C25 C24 C23 111.22(11) . . ?
C25 C24 H24A 109.4 . . ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24B 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-2



_database_code_depnum_ccdc_archive 'CCDC 995118'
