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

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

data_1_mbox2CH2
_database_code_depnum_ccdc_archive 'CCDC 1429338'
_audit_update_record             
;
2015-10-03 deposited with the CCDC.
2015-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        bis-(4-methylbenzoxazol-2-yl)-methane
_chemical_name_common            (4-Me-NCOC6H3)2CH2
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 N2 O2'
_chemical_formula_sum            'C17 H14 N2 O2'
_chemical_formula_weight         278.30

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      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                   4.741(2)
_cell_length_b                   11.471(3)
_cell_length_c                   13.084(3)
_cell_angle_alpha                79.15(2)
_cell_angle_beta                 85.84(2)
_cell_angle_gamma                78.19(2)
_cell_volume                     683.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5428
_cell_measurement_theta_min      3.3745
_cell_measurement_theta_max      26.3255

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8714
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_process_details   SADABS-2014/4

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'INCOATEC Microsource'
_diffrn_measurement_device_type  'Bruker Smart APEX II Quazar'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23615
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.586
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2495
_reflns_number_gt                2135
_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       'APEX2 v2012.2'
_computing_cell_refinement       'SAINT V7.68A'
_computing_data_reduction        'SAINT V7.68A'
_computing_structure_solution    'SHELXS-2012 (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'

_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)+(0.0385P)²+0.2479P] 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       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2495
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0938
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 -0.1061(3) 0.84083(13) 0.10266(11) 0.0299(3) Uani 1 1 d . . . . .
H1'A H -0.2787 0.8033 0.1114 0.036 Uiso 1 1 calc R U . . .
H1'B H -0.1710 0.9296 0.0841 0.036 Uiso 1 1 calc R U . . .
C1 C 0.0476(3) 0.81106(12) 0.20239(10) 0.0272(3) Uani 1 1 d . . . . .
O1 O -0.0832(2) 0.86989(9) 0.28075(7) 0.0312(3) Uani 1 1 d . . . . .
C2 C 0.0970(3) 0.82293(13) 0.36359(11) 0.0311(3) Uani 1 1 d . . . . .
C3 C 0.0647(3) 0.84933(15) 0.46286(12) 0.0394(4) Uani 1 1 d . . . . .
H3 H -0.0920 0.9070 0.4837 0.047 Uiso 1 1 calc R U . . .
C4 C 0.2800(4) 0.78476(16) 0.53002(12) 0.0428(4) Uani 1 1 d . . . . .
H4 H 0.2725 0.7995 0.5993 0.051 Uiso 1 1 calc R U . . .
C5 C 0.5055(3) 0.69933(15) 0.49857(12) 0.0389(4) Uani 1 1 d . . . . .
H5 H 0.6461 0.6573 0.5476 0.047 Uiso 1 1 calc R U . . .
C6 C 0.5347(3) 0.67254(14) 0.39863(11) 0.0323(3) Uani 1 1 d . . . . .
C7 C 0.3221(3) 0.73947(13) 0.33052(10) 0.0286(3) Uani 1 1 d . . . . .
C15 C 0.7724(3) 0.57719(14) 0.36631(12) 0.0368(4) Uani 1 1 d . . . . .
H15A H 0.8111 0.5965 0.2911 0.055 Uiso 1 1 calc R U . . .
H15B H 0.7144 0.4984 0.3835 0.055 Uiso 1 1 calc R U . . .
H15C H 0.9470 0.5743 0.4032 0.055 Uiso 1 1 calc R U . . .
N1 N 0.2849(2) 0.73515(10) 0.22530(8) 0.0275(3) Uani 1 1 d . . . . .
C8 C 0.0852(3) 0.79619(12) 0.01752(11) 0.0276(3) Uani 1 1 d . . . . .
O2 O 0.0909(2) 0.68000(9) 0.00421(7) 0.0305(3) Uani 1 1 d . . . . .
C9 C 0.2924(3) 0.66413(13) -0.07665(10) 0.0290(3) Uani 1 1 d . . . . .
C10 C 0.3861(3) 0.56195(14) -0.12069(11) 0.0355(4) Uani 1 1 d . . . . .
H10 H 0.3117 0.4900 -0.0991 0.043 Uiso 1 1 calc R U . . .
C11 C 0.5971(3) 0.57272(15) -0.19885(12) 0.0374(4) Uani 1 1 d . . . . .
H11 H 0.6740 0.5050 -0.2314 0.045 Uiso 1 1 calc R U . . .
C12 C 0.7006(3) 0.67983(14) -0.23151(11) 0.0350(4) Uani 1 1 d . . . . .
H12 H 0.8454 0.6822 -0.2856 0.042 Uiso 1 1 calc R U . . .
C13 C 0.6007(3) 0.78292(14) -0.18831(11) 0.0309(3) Uani 1 1 d . . . . .
C14 C 0.3925(3) 0.77094(12) -0.10728(10) 0.0273(3) Uani 1 1 d . . . . .
C16 C 0.7037(3) 0.89936(14) -0.22515(12) 0.0378(4) Uani 1 1 d . . . . .
H16A H 0.8959 0.8826 -0.2585 0.057 Uiso 1 1 calc R U . . .
H16B H 0.7129 0.9389 -0.1656 0.057 Uiso 1 1 calc R U . . .
H16C H 0.5697 0.9527 -0.2754 0.057 Uiso 1 1 calc R U . . .
N2 N 0.2537(2) 0.85441(10) -0.04492(9) 0.0279(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1' C8 1.484(2) . ?
C1' C1 1.489(2) . ?
C1 N1 1.2896(19) . ?
C1 O1 1.3740(17) . ?
O1 C2 1.3859(18) . ?
C2 C3 1.379(2) . ?
C2 C7 1.383(2) . ?
C3 C4 1.392(2) . ?
C4 C5 1.390(2) . ?
C5 C6 1.390(2) . ?
C6 C7 1.398(2) . ?
C6 C15 1.498(2) . ?
C7 N1 1.4119(18) . ?
C8 N2 1.2924(18) . ?
C8 O2 1.3709(17) . ?
O2 C9 1.3858(17) . ?
C9 C10 1.381(2) . ?
C9 C14 1.383(2) . ?
C10 C11 1.384(2) . ?
C11 C12 1.397(2) . ?
C12 C13 1.388(2) . ?
C13 C14 1.402(2) . ?
C13 C16 1.499(2) . ?
C14 N2 1.4049(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C1' C1 110.79(12) . . ?
N1 C1 O1 115.82(12) . . ?
N1 C1 C1' 128.23(13) . . ?
O1 C1 C1' 115.93(12) . . ?
C1 O1 C2 103.76(11) . . ?
C3 C2 C7 124.20(15) . . ?
C3 C2 O1 128.21(14) . . ?
C7 C2 O1 107.58(12) . . ?
C2 C3 C4 114.72(15) . . ?
C5 C4 C3 121.87(15) . . ?
C6 C5 C4 122.99(15) . . ?
C5 C6 C7 115.10(15) . . ?
C5 C6 C15 122.73(14) . . ?
C7 C6 C15 122.16(13) . . ?
C2 C7 C6 121.10(13) . . ?
C2 C7 N1 108.80(13) . . ?
C6 C7 N1 130.07(14) . . ?
C1 N1 C7 104.04(12) . . ?
N2 C8 O2 115.73(12) . . ?
N2 C8 C1' 126.95(13) . . ?
O2 C8 C1' 117.30(12) . . ?
C8 O2 C9 103.66(11) . . ?
C10 C9 C14 124.23(14) . . ?
C10 C9 O2 128.10(13) . . ?
C14 C9 O2 107.67(12) . . ?
C9 C10 C11 114.65(14) . . ?
C10 C11 C12 122.17(15) . . ?
C13 C12 C11 122.76(14) . . ?
C12 C13 C14 115.03(14) . . ?
C12 C13 C16 123.11(14) . . ?
C14 C13 C16 121.86(14) . . ?
C9 C14 C13 121.12(13) . . ?
C9 C14 N2 108.77(12) . . ?
C13 C14 N2 130.10(13) . . ?
C8 N2 C14 104.17(12) . . ?

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 C1' C1 N1 -15.3(2) . . . . ?
C8 C1' C1 O1 166.26(11) . . . . ?
N1 C1 O1 C2 -0.61(15) . . . . ?
C1' C1 O1 C2 177.99(11) . . . . ?
C1 O1 C2 C3 -178.84(14) . . . . ?
C1 O1 C2 C7 -0.14(13) . . . . ?
C7 C2 C3 C4 0.0(2) . . . . ?
O1 C2 C3 C4 178.54(13) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 C7 1.0(2) . . . . ?
C4 C5 C6 C15 -177.73(14) . . . . ?
C3 C2 C7 C6 1.5(2) . . . . ?
O1 C2 C7 C6 -177.30(11) . . . . ?
C3 C2 C7 N1 179.52(13) . . . . ?
O1 C2 C7 N1 0.76(14) . . . . ?
C5 C6 C7 C2 -1.90(19) . . . . ?
C15 C6 C7 C2 176.84(12) . . . . ?
C5 C6 C7 N1 -179.50(13) . . . . ?
C15 C6 C7 N1 -0.8(2) . . . . ?
O1 C1 N1 C7 1.06(15) . . . . ?
C1' C1 N1 C7 -177.33(13) . . . . ?
C2 C7 N1 C1 -1.09(14) . . . . ?
C6 C7 N1 C1 176.74(14) . . . . ?
C1 C1' C8 N2 -90.34(17) . . . . ?
C1 C1' C8 O2 88.09(14) . . . . ?
N2 C8 O2 C9 0.70(15) . . . . ?
C1' C8 O2 C9 -177.91(11) . . . . ?
C8 O2 C9 C10 178.83(14) . . . . ?
C8 O2 C9 C14 -0.53(13) . . . . ?
C14 C9 C10 C11 1.1(2) . . . . ?
O2 C9 C10 C11 -178.18(13) . . . . ?
C9 C10 C11 C12 -1.4(2) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C11 C12 C13 C14 1.5(2) . . . . ?
C11 C12 C13 C16 -178.00(13) . . . . ?
C10 C9 C14 C13 0.6(2) . . . . ?
O2 C9 C14 C13 179.94(12) . . . . ?
C10 C9 C14 N2 -179.14(13) . . . . ?
O2 C9 C14 N2 0.25(14) . . . . ?
C12 C13 C14 C9 -1.83(19) . . . . ?
C16 C13 C14 C9 177.73(13) . . . . ?
C12 C13 C14 N2 177.79(13) . . . . ?
C16 C13 C14 N2 -2.7(2) . . . . ?
O2 C8 N2 C14 -0.54(15) . . . . ?
C1' C8 N2 C14 177.91(13) . . . . ?
C9 C14 N2 C8 0.16(14) . . . . ?
C13 C14 N2 C8 -179.49(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1' H1'A N1 0.99 2.62 3.523(2) 150.9 1_455
C1' H1'B N2 0.99 2.39 3.371(2) 171.1 2_575

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-4


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

data_4_mbox2CHInMe2
_database_code_depnum_ccdc_archive 'CCDC 1429339'
_audit_update_record             
;
2015-10-03 deposited with the CCDC.
2015-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'Dimethyl indium bis-(4-methylbenzoxazol-2-yl)-methanide'
_chemical_name_common            '[Me2In{(4-Me-NCOC6H3)2CH}]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 In N2 O2'
_chemical_formula_sum            'C19 H19 In N2 O2'
_chemical_formula_weight         422.18

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'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
In In -1.2843 0.8542 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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'

_cell_length_a                   15.629(3)
_cell_length_b                   7.894(2)
_cell_length_c                   15.631(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.04(2)
_cell_angle_gamma                90
_cell_volume                     1717.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    106(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.109
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.081
_exptl_absorpt_coefficient_mu    0.741
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6620
_exptl_absorpt_correction_T_max  0.7447
_exptl_absorpt_process_details   SADABS-2014/4

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      106(2)
_diffrn_radiation_wavelength     0.56086
_diffrn_radiation_type           AgK\a
_diffrn_source                   'INCOATEC Microsource'
_diffrn_measurement_device_type  'Bruker Smart APEX II Quazar'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49033
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.154
_diffrn_reflns_theta_max         21.987
_diffrn_reflns_theta_full        19.665
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8534
_reflns_number_gt                8046
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_max     0.996
_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       'APEX2 v2012.2'
_computing_cell_refinement       'SAINT V8.34A'
_computing_data_reduction        'SAINT V8.34A'
_computing_structure_solution    'SHELXT (Sheldrick,Acta Cryst.(2015)A71,3-8)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'

_refine_special_details          'Twin, disorder of whole molecule'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0261P)²+0.1318P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3818 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.11(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8534
_refine_ls_number_parameters     744
_refine_ls_number_restraints     3149
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.0546
_refine_ls_wR_factor_gt          0.0533
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      0.911
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 0.2340(11) 1.1556(6) 0.2947(9) 0.0207(16) Uani 0.971(3) 1 d D U P A 1
H1' H 0.2435 1.2741 0.2927 0.025 Uiso 0.971(3) 1 calc R U P A 1
C1 C 0.1797(10) 1.0725(15) 0.2097(7) 0.0204(14) Uani 0.971(3) 1 d D U P A 1
O1 O 0.1300(7) 1.1723(13) 0.1291(6) 0.0224(15) Uani 0.971(3) 1 d D U P A 1
C2 C 0.0889(9) 1.0611(16) 0.0553(7) 0.0200(14) Uani 0.971(3) 1 d D U P A 1
C3 C 0.0312(9) 1.0985(16) -0.0408(8) 0.0235(16) Uani 0.971(3) 1 d D U P A 1
H3 H 0.0120 1.2103 -0.0641 0.028 Uiso 0.971(3) 1 calc R U P A 1
C4 C 0.0043(8) 0.9554(14) -0.0999(7) 0.0258(18) Uani 0.971(3) 1 d D U P A 1
H4 H -0.0342 0.9725 -0.1669 0.031 Uiso 0.971(3) 1 calc R U P A 1
C5 C 0.0292(9) 0.7928(14) -0.0686(8) 0.0237(18) Uani 0.971(3) 1 d D U P A 1
H5 H 0.0096 0.7029 -0.1139 0.028 Uiso 0.971(3) 1 calc R U P A 1
C6 C 0.0827(9) 0.7568(15) 0.0283(7) 0.0212(17) Uani 0.971(3) 1 d D U P A 1
C7 C 0.1121(10) 0.8963(14) 0.0883(7) 0.0176(14) Uani 0.971(3) 1 d D U P A 1
N1 N 0.1706(8) 0.9073(13) 0.1882(7) 0.0182(13) Uani 0.971(3) 1 d D U P A 1
C15 C 0.1053(13) 0.5774(17) 0.0616(11) 0.030(3) Uani 0.971(3) 1 d D U P A 1
H15A H 0.0701 0.5008 0.0075 0.046 Uiso 0.971(3) 1 calc R U P A 1
H15B H 0.0863 0.5561 0.1123 0.046 Uiso 0.971(3) 1 calc R U P A 1
H15C H 0.1745 0.5577 0.0868 0.046 Uiso 0.971(3) 1 calc R U P A 1
In1 In 0.22843(13) 0.70466(9) 0.29749(14) 0.01725(11) Uani 0.971(3) 1 d D U P A
1
C1M C 0.1104(9) 0.5917(18) 0.3123(9) 0.025(3) Uani 0.971(3) 1 d D U P A 1
H1MA H 0.0790 0.5073 0.2616 0.037 Uiso 0.971(3) 1 calc R U P A 1
H1MB H 0.0640 0.6798 0.3069 0.037 Uiso 0.971(3) 1 calc R U P A 1
H1MC H 0.1346 0.5367 0.3752 0.037 Uiso 0.971(3) 1 calc R U P A 1
C2M C 0.3487(9) 0.5878(18) 0.2890(10) 0.025(3) Uani 0.971(3) 1 d D U P A 1
H2MA H 0.3268 0.4872 0.2479 0.038 Uiso 0.971(3) 1 calc R U P A 1
H2MB H 0.3968 0.5546 0.3535 0.038 Uiso 0.971(3) 1 calc R U P A 1
H2MC H 0.3774 0.6684 0.2617 0.038 Uiso 0.971(3) 1 calc R U P A 1
C8 C 0.2758(10) 1.0745(15) 0.3837(7) 0.0188(14) Uani 0.971(3) 1 d D U P A 1
O2 O 0.3196(7) 1.1748(13) 0.4633(6) 0.0215(15) Uani 0.971(3) 1 d D U P A 1
C9 C 0.3634(9) 1.0653(15) 0.5410(7) 0.0188(14) Uani 0.971(3) 1 d D U P A 1
C10 C 0.4182(9) 1.1111(16) 0.6358(8) 0.0231(17) Uani 0.971(3) 1 d D U P A 1
H10 H 0.4286 1.2265 0.6551 0.028 Uiso 0.971(3) 1 calc R U P A 1
C11 C 0.4572(7) 0.9806(14) 0.7010(7) 0.0225(17) Uani 0.971(3) 1 d D U P A 1
H11 H 0.4981 1.0041 0.7668 0.027 Uiso 0.971(3) 1 calc R U P A 1
C12 C 0.4358(8) 0.8145(14) 0.6692(7) 0.0225(18) Uani 0.971(3) 1 d D U P A 1
H12 H 0.4619 0.7265 0.7154 0.027 Uiso 0.971(3) 1 calc R U P A 1
C13 C 0.3777(8) 0.7679(15) 0.5724(7) 0.0214(18) Uani 0.971(3) 1 d D U P A 1
C14 C 0.3424(10) 0.9018(14) 0.5065(7) 0.0179(14) Uani 0.971(3) 1 d D U P A 1
N2 N 0.2867(8) 0.9095(12) 0.4057(6) 0.0173(13) Uani 0.971(3) 1 d D U P A 1
C16 C 0.3546(12) 0.5854(17) 0.5397(11) 0.031(3) Uani 0.971(3) 1 d D U P A 1
H16A H 0.2852 0.5732 0.4997 0.046 Uiso 0.971(3) 1 calc R U P A 1
H16B H 0.3754 0.5114 0.5960 0.046 Uiso 0.971(3) 1 calc R U P A 1
H16C H 0.3883 0.5537 0.5024 0.046 Uiso 0.971(3) 1 calc R U P A 1
C1'A C 0.7301(10) 1.1893(7) 0.2901(12) 0.0212(19) Uani 0.938(3) 1 d D U P B 1
H1'A H 0.7316 1.3072 0.2786 0.025 Uiso 0.938(3) 1 calc R U P B 1
C1A C 0.8155(8) 1.1088(15) 0.3447(12) 0.0221(15) Uani 0.938(3) 1 d D U P B 1
O1A O 0.8952(6) 1.2075(15) 0.3880(7) 0.0252(15) Uani 0.938(3) 1 d D U P B 1
C2A C 0.9723(7) 1.0975(16) 0.4322(11) 0.0229(15) Uani 0.938(3) 1 d D U P B 1
C3A C 1.0705(7) 1.1276(14) 0.4840(9) 0.0253(17) Uani 0.938(3) 1 d D U P B 1
H3A H 1.0964 1.2385 0.4905 0.030 Uiso 0.938(3) 1 calc R U P B 1
C4A C 1.1290(7) 0.9874(13) 0.5260(7) 0.0240(17) Uani 0.938(3) 1 d D U P B 1
H4A H 1.1955 1.0046 0.5669 0.029 Uiso 0.938(3) 1 calc R U P B 1
C5A C 1.0939(8) 0.8281(14) 0.5100(9) 0.0223(18) Uani 0.938(3) 1 d D U P B 1
H5A H 1.1367 0.7364 0.5394 0.027 Uiso 0.938(3) 1 calc R U P B 1
C6A C 0.9962(7) 0.7932(15) 0.4514(9) 0.0221(18) Uani 0.938(3) 1 d D U P B 1
C7A C 0.9356(7) 0.9331(15) 0.4156(9) 0.0200(15) Uani 0.938(3) 1 d D U P B 1
N1A N 0.8340(6) 0.9431(13) 0.3595(8) 0.0189(13) Uani 0.938(3) 1 d D U P B 1
C15A C 0.9614(12) 0.6133(17) 0.4402(13) 0.036(3) Uani 0.938(3) 1 d D U P B 1
H15D H 0.9377 0.5781 0.3732 0.054 Uiso 0.938(3) 1 calc R U P B 1
H15E H 0.9092 0.6053 0.4585 0.054 Uiso 0.938(3) 1 calc R U P B 1
H15F H 1.0144 0.5393 0.4817 0.054 Uiso 0.938(3) 1 calc R U P B 1
In1A In 0.72596(15) 0.73930(11) 0.29521(15) 0.01830(13) Uani 0.938(3) 1 d D U P
B 1
C1MA C 0.7511(10) 0.6164(17) 0.1862(9) 0.026(3) Uani 0.938(3) 1 d D U P B 1
H1MD H 0.7050 0.5236 0.1580 0.040 Uiso 0.938(3) 1 calc R U P B 1
H1ME H 0.8166 0.5711 0.2148 0.040 Uiso 0.938(3) 1 calc R U P B 1
H1MF H 0.7431 0.6985 0.1360 0.040 Uiso 0.938(3) 1 calc R U P B 1
C2MA C 0.7007(9) 0.6181(17) 0.4056(9) 0.025(3) Uani 0.938(3) 1 d D U P B 1
H2MD H 0.6609 0.5170 0.3790 0.037 Uiso 0.938(3) 1 calc R U P B 1
H2ME H 0.6674 0.6970 0.4288 0.037 Uiso 0.938(3) 1 calc R U P B 1
H2MF H 0.7622 0.5851 0.4591 0.037 Uiso 0.938(3) 1 calc R U P B 1
C8A C 0.6397(8) 1.1068(15) 0.2498(12) 0.0232(15) Uani 0.938(3) 1 d D U P B 1
O2A O 0.5586(6) 1.2099(15) 0.2107(7) 0.0255(15) Uani 0.938(3) 1 d D U P B 1
C9A C 0.4835(7) 1.1007(16) 0.1658(11) 0.0241(15) Uani 0.938(3) 1 d D U P B 1
C10A C 0.3885(7) 1.1537(14) 0.1128(10) 0.0259(17) Uani 0.938(3) 1 d D U P B 1
H10A H 0.3699 1.2694 0.1012 0.031 Uiso 0.938(3) 1 calc R U P B 1
C11A C 0.3247(7) 1.0211(13) 0.0789(7) 0.0261(18) Uani 0.938(3) 1 d D U P B 1
H11A H 0.2578 1.0440 0.0478 0.031 Uiso 0.938(3) 1 calc R U P B 1
C12A C 0.3563(8) 0.8530(15) 0.0895(9) 0.0268(19) Uani 0.938(3) 1 d D U P B 1
H12A H 0.3092 0.7666 0.0624 0.032 Uiso 0.938(3) 1 calc R U P B 1
C13A C 0.4522(8) 0.8043(16) 0.1369(10) 0.0253(19) Uani 0.938(3) 1 d D U P B 1
C14A C 0.5161(7) 0.9353(15) 0.1797(10) 0.0211(15) Uani 0.938(3) 1 d D U P B 1
N2A N 0.6162(6) 0.9433(13) 0.2356(8) 0.0205(13) Uani 0.938(3) 1 d D U P B 1
C16A C 0.4869(10) 0.6215(17) 0.1543(12) 0.027(3) Uani 0.938(3) 1 d D U P B 1
H16D H 0.4322 0.5453 0.1207 0.041 Uiso 0.938(3) 1 calc R U P B 1
H16E H 0.5167 0.5973 0.2233 0.041 Uiso 0.938(3) 1 calc R U P B 1
H16F H 0.5341 0.6040 0.1301 0.041 Uiso 0.938(3) 1 calc R U P B 1
C1'B C 0.258(4) 0.833(3) 0.296(3) 0.018(2) Uani 0.029(3) 1 d G U P A 2
H1'B H 0.2787 0.7205 0.2961 0.022 Uiso 0.029(3) 1 d G U P A 2
C1B C 0.195(4) 0.903(4) 0.211(3) 0.020(2) Uani 0.029(3) 1 d G U P A 2
O1B O 0.162(5) 0.799(5) 0.131(4) 0.021(2) Uani 0.029(3) 1 d G U P A 2
C2B C 0.113(4) 0.903(6) 0.057(3) 0.0211(19) Uani 0.029(3) 1 d G U P A 2
C3B C 0.064(6) 0.860(8) -0.040(3) 0.022(2) Uani 0.029(3) 1 d G U P A 2
H3B H 0.0654 0.7484 -0.0632 0.026 Uiso 0.029(3) 1 d G U P A 2
C4B C 0.014(5) 0.991(9) -0.101(2) 0.023(3) Uani 0.029(3) 1 d G U P A 2
H4B H -0.0202 0.9684 -0.1676 0.027 Uiso 0.029(3) 1 d G U P A 2
C5B C 0.010(5) 1.153(8) -0.070(2) 0.023(3) Uani 0.029(3) 1 d G U P A 2
H5B H -0.0278 1.2360 -0.1154 0.028 Uiso 0.029(3) 1 d G U P A 2
C6B C 0.061(4) 1.197(6) 0.0267(19) 0.022(3) Uani 0.029(3) 1 d G U P A 2
C7B C 0.110(3) 1.067(5) 0.088(2) 0.020(2) Uani 0.029(3) 1 d G U P A 2
N1B N 0.166(3) 1.064(4) 0.188(2) 0.0206(19) Uani 0.029(3) 1 d G U P A 2
C15B C 0.061(4) 1.378(6) 0.054(2) 0.022(8) Uani 0.029(3) 1 d G U P A 2
H15G H 0.0295 1.4470 -0.0042 0.032 Uiso 0.029(3) 1 d G U P A 2
H15H H 0.1273 1.4162 0.0918 0.032 Uiso 0.029(3) 1 d G U P A 2
H15I H 0.0261 1.3892 0.0923 0.032 Uiso 0.029(3) 1 d G U P A 2
In1B In 0.209(2) 1.274(2) 0.2930(19) 0.025(3) Uani 0.029(3) 1 d G U P A 2
C1MB C 0.311(3) 1.429(6) 0.271(3) 0.026(8) Uani 0.029(3) 1 d G U P A 2
H1MG H 0.2766 1.5082 0.2183 0.039 Uiso 0.029(3) 1 d G U P A 2
H1MH H 0.3527 1.3563 0.2552 0.039 Uiso 0.029(3) 1 d G U P A 2
H1MI H 0.3503 1.4923 0.3300 0.039 Uiso 0.029(3) 1 d G U P A 2
C2MB C 0.088(3) 1.346(5) 0.315(3) 0.026(8) Uani 0.029(3) 1 d G U P A 2
H2MG H 0.0547 1.4420 0.2737 0.038 Uiso 0.029(3) 1 d G U P A 2
H2MH H 0.1100 1.3782 0.3827 0.038 Uiso 0.029(3) 1 d G U P A 2
H2MI H 0.0433 1.2500 0.2998 0.038 Uiso 0.029(3) 1 d G U P A 2
C8B C 0.293(3) 0.918(4) 0.384(3) 0.019(2) Uani 0.029(3) 1 d G U P A 2
O2B O 0.346(4) 0.827(5) 0.466(3) 0.020(2) Uani 0.029(3) 1 d G U P A 2
C9B C 0.381(4) 0.941(6) 0.542(3) 0.0203(18) Uani 0.029(3) 1 d G U P A 2
C10B C 0.435(5) 0.901(8) 0.638(3) 0.021(2) Uani 0.029(3) 1 d G U P A 2
H10B H 0.4562 0.7891 0.6589 0.025 Uiso 0.029(3) 1 d G U P A 2
C11B C 0.458(5) 1.037(10) 0.701(2) 0.022(3) Uani 0.029(3) 1 d G U P A 2
H11B H 0.4942 1.0196 0.7685 0.026 Uiso 0.029(3) 1 d G U P A 2
C12B C 0.427(5) 1.199(9) 0.666(2) 0.022(3) Uani 0.029(3) 1 d G U P A 2
H12B H 0.4452 1.2897 0.7104 0.026 Uiso 0.029(3) 1 d G U P A 2
C13B C 0.371(4) 1.238(7) 0.567(2) 0.021(3) Uani 0.029(3) 1 d G U P A 2
C14B C 0.347(3) 1.098(6) 0.505(2) 0.020(2) Uani 0.029(3) 1 d G U P A 2
N2B N 0.292(2) 1.083(4) 0.404(2) 0.0198(19) Uani 0.029(3) 1 d G U P A 2
C16B C 0.343(4) 1.417(6) 0.527(2) 0.022(8) Uani 0.029(3) 1 d G U P A 2
H16G H 0.3602 1.4336 0.4744 0.033 Uiso 0.029(3) 1 d G U P A 2
H16H H 0.3774 1.4996 0.5777 0.033 Uiso 0.029(3) 1 d G U P A 2
H16I H 0.2738 1.4317 0.5025 0.033 Uiso 0.029(3) 1 d G U P A 2
C1'C C 0.7155(19) 0.8426(9) 0.310(2) 0.020(3) Uani 0.062(3) 1 d G U P B 2
H1'C H 0.7143 0.7260 0.3243 0.024 Uiso 0.062(3) 1 d G U P B 2
C1C C 0.8026(16) 0.9224(15) 0.347(2) 0.021(2) Uani 0.062(3) 1 d G U P B 2
O1C O 0.883(2) 0.823(3) 0.397(3) 0.022(2) Uani 0.062(3) 1 d G U P B 2
C2C C 0.9556(16) 0.934(3) 0.435(2) 0.022(2) Uani 0.062(3) 1 d G U P B 2
C3C C 1.0527(17) 0.898(5) 0.492(3) 0.023(2) Uani 0.062(3) 1 d G U P B 2
H3C H 1.0757 0.7864 0.5124 0.027 Uiso 0.062(3) 1 d G U P B 2
C4C C 1.1128(14) 1.037(6) 0.515(3) 0.024(3) Uani 0.062(3) 1 d G U P B 2
H4C H 1.1796 1.0195 0.5540 0.029 Uiso 0.062(3) 1 d G U P B 2
C5C C 1.0819(12) 1.200(5) 0.486(2) 0.024(3) Uani 0.062(3) 1 d G U P B 2
H5C H 1.1276 1.2888 0.5027 0.029 Uiso 0.062(3) 1 d G U P B 2
C6C C 0.9846(12) 1.236(4) 0.4310(19) 0.025(3) Uani 0.062(3) 1 d G U P B 2
C7C C 0.9237(12) 1.099(3) 0.4058(17) 0.023(2) Uani 0.062(3) 1 d G U P B 2
N1C N 0.8240(12) 1.0875(17) 0.3511(14) 0.0222(19) Uani 0.062(3) 1 d G U P B 2
C15C C 0.9551(15) 1.417(3) 0.409(2) 0.030(7) Uani 0.062(3) 1 d G U P B 2
H15J H 1.0107 1.4902 0.4445 0.045 Uiso 0.062(3) 1 d G U P B 2
H15K H 0.9050 1.4423 0.4286 0.045 Uiso 0.062(3) 1 d G U P B 2
H15L H 0.9300 1.4369 0.3401 0.045 Uiso 0.062(3) 1 d G U P B 2
In1C In 0.7159(12) 1.2908(8) 0.2866(13) 0.0263(16) Uani 0.062(3) 1 d G U P B 2
C1MC C 0.7049(18) 1.422(3) 0.4020(18) 0.025(8) Uani 0.062(3) 1 d G U P B 2
H1MJ H 0.7563 1.5064 0.4296 0.037 Uiso 0.062(3) 1 d G U P B 2
H1MK H 0.7109 1.3406 0.4517 0.037 Uiso 0.062(3) 1 d G U P B 2
H1ML H 0.6424 1.4789 0.3772 0.037 Uiso 0.062(3) 1 d G U P B 2
C2MC C 0.7238(17) 1.389(3) 0.1617(17) 0.030(8) Uani 0.062(3) 1 d G U P B 2
H2MJ H 0.7646 1.4896 0.1794 0.044 Uiso 0.062(3) 1 d G U P B 2
H2MK H 0.6591 1.4183 0.1125 0.044 Uiso 0.062(3) 1 d G U P B 2
H2ML H 0.7511 1.3021 0.1363 0.044 Uiso 0.062(3) 1 d G U P B 2
C8C C 0.6284(16) 0.9222(14) 0.252(2) 0.022(2) Uani 0.062(3) 1 d G U P B 2
O2C O 0.548(2) 0.824(2) 0.211(3) 0.023(2) Uani 0.062(3) 1 d G U P B 2
C9C C 0.4698(16) 0.933(3) 0.166(2) 0.0239(19) Uani 0.062(3) 1 d G U P B 2
C10C C 0.3751(17) 0.884(5) 0.113(3) 0.025(2) Uani 0.062(3) 1 d G U P B 2
H10C H 0.3555 0.7692 0.1052 0.030 Uiso 0.062(3) 1 d G U P B 2
C11C C 0.3103(14) 1.017(6) 0.072(3) 0.026(3) Uani 0.062(3) 1 d G U P B 2
H11C H 0.2440 0.9940 0.0327 0.031 Uiso 0.062(3) 1 d G U P B 2
C12C C 0.3432(12) 1.183(5) 0.087(2) 0.026(3) Uani 0.062(3) 1 d G U P B 2
H12C H 0.2973 1.2708 0.0597 0.031 Uiso 0.062(3) 1 d G U P B 2
C13C C 0.4407(12) 1.230(4) 0.142(2) 0.026(3) Uani 0.062(3) 1 d G U P B 2
C14C C 0.5048(12) 1.094(3) 0.1799(18) 0.023(2) Uani 0.062(3) 1 d G U P B 2
N2C N 0.6062(12) 1.0876(17) 0.2368(15) 0.0231(19) Uani 0.062(3) 1 d G U P B 2
C16C C 0.4766(15) 1.412(3) 0.166(2) 0.032(8) Uani 0.062(3) 1 d G U P B 2
H16J H 0.5172 1.4235 0.2349 0.048 Uiso 0.062(3) 1 d G U P B 2
H16K H 0.4216 1.4891 0.1453 0.048 Uiso 0.062(3) 1 d G U P B 2
H16L H 0.5140 1.4409 0.1315 0.048 Uiso 0.062(3) 1 d G U P B 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' C1 1.375(13) . ?
C1' C8 1.396(12) . ?
C1 N1 1.338(11) . ?
C1 O1 1.386(11) . ?
O1 C2 1.356(12) . ?
C2 C7 1.386(12) . ?
C2 C3 1.388(12) . ?
C3 C4 1.398(12) . ?
C4 C5 1.367(11) . ?
C5 C6 1.386(12) . ?
C6 C7 1.382(12) . ?
C6 C15 1.495(12) . ?
C7 N1 1.409(11) . ?
N1 In1 2.211(9) . ?
In1 C2M 2.152(10) . ?
In1 C1M 2.154(10) . ?
In1 N2 2.215(9) . ?
C8 N2 1.338(11) . ?
C8 O2 1.367(12) . ?
O2 C9 1.391(11) . ?
C9 C14 1.379(12) . ?
C9 C10 1.380(12) . ?
C10 C11 1.382(12) . ?
C11 C12 1.388(11) . ?
C12 C13 1.414(12) . ?
C13 C14 1.402(11) . ?
C13 C16 1.516(13) . ?
C14 N2 1.412(11) . ?
C1'A C1A 1.370(13) . ?
C1'A C8A 1.417(13) . ?
C1A N1A 1.337(12) . ?
C1A O1A 1.360(12) . ?
O1A C2A 1.389(12) . ?
C2A C3A 1.391(12) . ?
C2A C7A 1.395(12) . ?
C3A C4A 1.396(11) . ?
C4A C5A 1.349(12) . ?
C5A C6A 1.405(12) . ?
C6A C7A 1.396(12) . ?
C6A C15A 1.503(13) . ?
C7A N1A 1.425(11) . ?
N1A In1A 2.215(9) . ?
In1A C1MA 2.147(9) . ?
In1A C2MA 2.161(11) . ?
In1A N2A 2.225(9) . ?
C8A N2A 1.333(12) . ?
C8A O2A 1.392(12) . ?
O2A C9A 1.365(12) . ?
C9A C14A 1.383(13) . ?
C9A C10A 1.395(12) . ?
C10A C11A 1.375(12) . ?
C11A C12A 1.399(12) . ?
C12A C13A 1.391(12) . ?
C13A C14A 1.380(12) . ?
C13A C16A 1.522(13) . ?
C14A N2A 1.405(11) . ?
C1'B C1B 1.3668 . ?
C1'B C8B 1.3944 . ?
C1B N1B 1.3396 . ?
C1B O1B 1.3825 . ?
O1B C2B 1.3471 . ?
C2B C7B 1.3922 . ?
C2B C3B 1.3959 . ?
C3B C4B 1.3834 . ?
C4B C5B 1.3745 . ?
C5B C6B 1.3940 . ?
C6B C7B 1.3774 . ?
C6B C15B 1.4905 . ?
C7B N1B 1.3981 . ?
N1B In1B 2.2131 . ?
In1B C1MB 2.1540 . ?
In1B C2MB 2.1545 . ?
In1B N2B 2.2144 . ?
C8B N2B 1.3441 . ?
C8B O2B 1.3643 . ?
O2B C9B 1.3940 . ?
C9B C14B 1.3666 . ?
C9B C10B 1.3811 . ?
C10B C11B 1.3943 . ?
C11B C12B 1.3867 . ?
C12B C13B 1.4166 . ?
C13B C14B 1.4016 . ?
C13B C16B 1.5259 . ?
C14B N2B 1.4225 . ?
C1'C C1C 1.3669 . ?
C1'C C8C 1.3944 . ?
C1C N1C 1.3396 . ?
C1C O1C 1.3825 . ?
O1C C2C 1.3472 . ?
C2C C7C 1.3922 . ?
C2C C3C 1.3958 . ?
C3C C4C 1.3835 . ?
C4C C5C 1.3744 . ?
C5C C6C 1.3940 . ?
C6C C7C 1.3774 . ?
C6C C15C 1.4904 . ?
C7C N1C 1.3981 . ?
N1C In1C 2.2131 . ?
In1C C1MC 2.1540 . ?
In1C C2MC 2.1545 . ?
In1C N2C 2.2144 . ?
C8C N2C 1.3441 . ?
C8C O2C 1.3643 . ?
O2C C9C 1.3940 . ?
C9C C14C 1.3666 . ?
C9C C10C 1.3810 . ?
C10C C11C 1.3943 . ?
C11C C12C 1.3867 . ?
C12C C13C 1.4166 . ?
C13C C14C 1.4015 . ?
C13C C16C 1.5259 . ?
C14C N2C 1.4225 . ?

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 C1' C8 123.3(5) . . ?
N1 C1 C1' 131.0(9) . . ?
N1 C1 O1 112.0(9) . . ?
C1' C1 O1 116.8(10) . . ?
C2 O1 C1 105.0(9) . . ?
O1 C2 C7 110.4(9) . . ?
O1 C2 C3 127.3(10) . . ?
C7 C2 C3 122.3(10) . . ?
C2 C3 C4 113.3(10) . . ?
C5 C4 C3 124.8(10) . . ?
C4 C5 C6 121.1(10) . . ?
C7 C6 C5 115.3(9) . . ?
C7 C6 C15 124.5(10) . . ?
C5 C6 C15 120.3(11) . . ?
C6 C7 C2 123.1(9) . . ?
C6 C7 N1 130.5(10) . . ?
C2 C7 N1 106.4(8) . . ?
C1 N1 C7 106.2(8) . . ?
C1 N1 In1 123.5(7) . . ?
C7 N1 In1 130.0(7) . . ?
C2M In1 C1M 130.10(19) . . ?
C2M In1 N1 108.9(5) . . ?
C1M In1 N1 108.3(5) . . ?
C2M In1 N2 107.0(5) . . ?
C1M In1 N2 107.1(5) . . ?
N1 In1 N2 86.77(13) . . ?
N2 C8 O2 112.2(9) . . ?
N2 C8 C1' 130.5(10) . . ?
O2 C8 C1' 117.1(10) . . ?
C8 O2 C9 106.2(9) . . ?
C14 C9 C10 125.9(10) . . ?
C14 C9 O2 107.7(8) . . ?
C10 C9 O2 126.4(10) . . ?
C9 C10 C11 116.6(10) . . ?
C10 C11 C12 119.1(9) . . ?
C11 C12 C13 124.2(10) . . ?
C14 C13 C12 115.9(10) . . ?
C14 C13 C16 121.0(10) . . ?
C12 C13 C16 123.1(10) . . ?
C9 C14 C13 118.2(9) . . ?
C9 C14 N2 108.2(8) . . ?
C13 C14 N2 133.5(10) . . ?
C8 N2 C14 105.7(8) . . ?
C8 N2 In1 123.7(7) . . ?
C14 N2 In1 130.6(7) . . ?
C1A C1'A C8A 123.8(6) . . ?
N1A C1A O1A 113.4(10) . . ?
N1A C1A C1'A 129.4(10) . . ?
O1A C1A C1'A 117.2(10) . . ?
C1A O1A C2A 106.3(10) . . ?
O1A C2A C3A 131.4(11) . . ?
O1A C2A C7A 107.3(9) . . ?
C3A C2A C7A 121.3(10) . . ?
C2A C3A C4A 116.9(10) . . ?
C5A C4A C3A 121.8(9) . . ?
C4A C5A C6A 122.2(10) . . ?
C7A C6A C5A 116.4(10) . . ?
C7A C6A C15A 123.8(10) . . ?
C5A C6A C15A 119.4(11) . . ?
C2A C7A C6A 120.9(9) . . ?
C2A C7A N1A 108.2(9) . . ?
C6A C7A N1A 130.9(10) . . ?
C1A N1A C7A 104.7(9) . . ?
C1A N1A In1A 124.9(7) . . ?
C7A N1A In1A 130.2(8) . . ?
C1MA In1A C2MA 126.85(18) . . ?
C1MA In1A N1A 108.1(5) . . ?
C2MA In1A N1A 109.8(5) . . ?
C1MA In1A N2A 112.3(5) . . ?
C2MA In1A N2A 105.6(5) . . ?
N1A In1A N2A 87.01(14) . . ?
N2A C8A O2A 111.5(9) . . ?
N2A C8A C1'A 131.5(10) . . ?
O2A C8A C1'A 116.9(10) . . ?
C9A O2A C8A 104.8(10) . . ?
O2A C9A C14A 110.2(9) . . ?
O2A C9A C10A 123.4(11) . . ?
C14A C9A C10A 126.4(10) . . ?
C11A C10A C9A 112.9(9) . . ?
C10A C11A C12A 121.4(9) . . ?
C13A C12A C11A 124.2(10) . . ?
C14A C13A C12A 114.7(10) . . ?
C14A C13A C16A 120.3(10) . . ?
C12A C13A C16A 124.6(11) . . ?
C13A C14A C9A 119.9(9) . . ?
C13A C14A N2A 133.7(10) . . ?
C9A C14A N2A 106.4(9) . . ?
C8A N2A C14A 107.0(9) . . ?
C8A N2A In1A 122.0(8) . . ?
C14A N2A In1A 131.1(8) . . ?
C1B C1'B C8B 123.9 . . ?
N1B C1B C1'B 130.4 . . ?
N1B C1B O1B 112.7 . . ?
C1'B C1B O1B 116.5 . . ?
C2B O1B C1B 104.1 . . ?
O1B C2B C7B 111.2 . . ?
O1B C2B C3B 127.1 . . ?
C7B C2B C3B 121.6 . . ?
C4B C3B C2B 114.6 . . ?
C5B C4B C3B 124.1 . . ?
C4B C5B C6B 121.1 . . ?
C7B C6B C5B 115.6 . . ?
C7B C6B C15B 125.9 . . ?
C5B C6B C15B 118.4 . . ?
C6B C7B C2B 122.9 . . ?
C6B C7B N1B 131.2 . . ?
C2B C7B N1B 106.0 . . ?
C1B N1B C7B 106.0 . . ?
C1B N1B In1B 124.1 . . ?
C7B N1B In1B 129.8 . . ?
C1MB In1B C2MB 130.2 . . ?
C1MB In1B N1B 107.6 . . ?
C2MB In1B N1B 109.0 . . ?
C1MB In1B N2B 107.4 . . ?
C2MB In1B N2B 107.2 . . ?
N1B In1B N2B 86.8 . . ?
N2B C8B O2B 111.2 . . ?
N2B C8B C1'B 130.6 . . ?
O2B C8B C1'B 117.9 . . ?
C8B O2B C9B 107.2 . . ?
C14B C9B C10B 126.4 . . ?
C14B C9B O2B 107.4 . . ?
C10B C9B O2B 126.1 . . ?
C9B C10B C11B 115.3 . . ?
C12B C11B C10B 119.5 . . ?
C11B C12B C13B 124.5 . . ?
C14B C13B C12B 114.8 . . ?
C14B C13B C16B 120.4 . . ?
C12B C13B C16B 124.7 . . ?
C9B C14B C13B 119.3 . . ?
C9B C14B N2B 108.5 . . ?
C13B C14B N2B 132.2 . . ?
C8B N2B C14B 105.7 . . ?
C8B N2B In1B 123.0 . . ?
C14B N2B In1B 131.1 . . ?
C1C C1'C C8C 123.9 . . ?
N1C C1C C1'C 130.4 . . ?
N1C C1C O1C 112.7 . . ?
C1'C C1C O1C 116.5 . . ?
C2C O1C C1C 104.1 . . ?
O1C C2C C7C 111.2 . . ?
O1C C2C C3C 127.1 . . ?
C7C C2C C3C 121.6 . . ?
C4C C3C C2C 114.6 . . ?
C5C C4C C3C 124.1 . . ?
C4C C5C C6C 121.1 . . ?
C7C C6C C5C 115.6 . . ?
C7C C6C C15C 125.9 . . ?
C5C C6C C15C 118.4 . . ?
C6C C7C C2C 122.9 . . ?
C6C C7C N1C 131.2 . . ?
C2C C7C N1C 106.0 . . ?
C1C N1C C7C 106.0 . . ?
C1C N1C In1C 124.1 . . ?
C7C N1C In1C 129.8 . . ?
C1MC In1C C2MC 130.2 . . ?
C1MC In1C N1C 107.6 . . ?
C2MC In1C N1C 109.0 . . ?
C1MC In1C N2C 107.4 . . ?
C2MC In1C N2C 107.2 . . ?
N1C In1C N2C 86.8 . . ?
N2C C8C O2C 111.2 . . ?
N2C C8C C1'C 130.6 . . ?
O2C C8C C1'C 117.9 . . ?
C8C O2C C9C 107.2 . . ?
C14C C9C C10C 126.4 . . ?
C14C C9C O2C 107.4 . . ?
C10C C9C O2C 126.1 . . ?
C9C C10C C11C 115.3 . . ?
C12C C11C C10C 119.5 . . ?
C11C C12C C13C 124.5 . . ?
C14C C13C C12C 114.8 . . ?
C14C C13C C16C 120.4 . . ?
C12C C13C C16C 124.7 . . ?
C9C C14C C13C 119.3 . . ?
C9C C14C N2C 108.5 . . ?
C13C C14C N2C 132.2 . . ?
C8C N2C C14C 105.7 . . ?
C8C N2C In1C 123.0 . . ?
C14C N2C In1C 131.1 . . ?

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 C1' C1 N1 -15(4) . . . . ?
C8 C1' C1 O1 169.8(11) . . . . ?
N1 C1 O1 C2 0.0(19) . . . . ?
C1' C1 O1 C2 175.7(14) . . . . ?
C1 O1 C2 C7 -0.2(16) . . . . ?
C1 O1 C2 C3 179.9(15) . . . . ?
O1 C2 C3 C4 176.7(13) . . . . ?
C7 C2 C3 C4 -3(2) . . . . ?
C2 C3 C4 C5 1(2) . . . . ?
C3 C4 C5 C6 2(2) . . . . ?
C4 C5 C6 C7 -3(2) . . . . ?
C4 C5 C6 C15 177.1(14) . . . . ?
C5 C6 C7 C2 1(2) . . . . ?
C15 C6 C7 C2 -179.1(16) . . . . ?
C5 C6 C7 N1 -176.3(14) . . . . ?
C15 C6 C7 N1 3(3) . . . . ?
O1 C2 C7 C6 -177.8(13) . . . . ?
C3 C2 C7 C6 2(3) . . . . ?
O1 C2 C7 N1 0.3(17) . . . . ?
C3 C2 C7 N1 -179.8(12) . . . . ?
C1' C1 N1 C7 -174.8(17) . . . . ?
O1 C1 N1 C7 0(2) . . . . ?
C1' C1 N1 In1 10(3) . . . . ?
O1 C1 N1 In1 -174.7(8) . . . . ?
C6 C7 N1 C1 177.6(16) . . . . ?
C2 C7 N1 C1 -0.3(19) . . . . ?
C6 C7 N1 In1 -8(2) . . . . ?
C2 C7 N1 In1 174.2(11) . . . . ?
C1 C1' C8 N2 12(4) . . . . ?
C1 C1' C8 O2 -173.5(11) . . . . ?
N2 C8 O2 C9 1.5(19) . . . . ?
C1' C8 O2 C9 -174.2(14) . . . . ?
C8 O2 C9 C14 -1.7(16) . . . . ?
C8 O2 C9 C10 178.1(15) . . . . ?
C14 C9 C10 C11 2(2) . . . . ?
O2 C9 C10 C11 -178.1(13) . . . . ?
C9 C10 C11 C12 -3.0(19) . . . . ?
C10 C11 C12 C13 2(2) . . . . ?
C11 C12 C13 C14 1(2) . . . . ?
C11 C12 C13 C16 -179.4(14) . . . . ?
C10 C9 C14 C13 1(3) . . . . ?
O2 C9 C14 C13 -178.9(13) . . . . ?
C10 C9 C14 N2 -178.5(13) . . . . ?
O2 C9 C14 N2 1.3(17) . . . . ?
C12 C13 C14 C9 -3(2) . . . . ?
C16 C13 C14 C9 178.0(15) . . . . ?
C12 C13 C14 N2 177.1(15) . . . . ?
C16 C13 C14 N2 -2(3) . . . . ?
O2 C8 N2 C14 -1(2) . . . . ?
C1' C8 N2 C14 174.2(16) . . . . ?
O2 C8 N2 In1 -179.1(8) . . . . ?
C1' C8 N2 In1 -4(3) . . . . ?
C9 C14 N2 C8 -0.4(19) . . . . ?
C13 C14 N2 C8 179.9(17) . . . . ?
C9 C14 N2 In1 177.9(11) . . . . ?
C13 C14 N2 In1 -2(3) . . . . ?
C8A C1'A C1A N1A 11(4) . . . . ?
C8A C1'A C1A O1A -172.5(12) . . . . ?
N1A C1A O1A C2A 2(2) . . . . ?
C1'A C1A O1A C2A -175.5(15) . . . . ?
C1A O1A C2A C3A 177.8(17) . . . . ?
C1A O1A C2A C7A -1.3(18) . . . . ?
O1A C2A C3A C4A 175.1(15) . . . . ?
C7A C2A C3A C4A -6(2) . . . . ?
C2A C3A C4A C5A 6.0(19) . . . . ?
C3A C4A C5A C6A -0.8(19) . . . . ?
C4A C5A C6A C7A -4(2) . . . . ?
C4A C5A C6A C15A -177.4(14) . . . . ?
O1A C2A C7A C6A 179.9(13) . . . . ?
C3A C2A C7A C6A 1(3) . . . . ?
O1A C2A C7A N1A 0.5(19) . . . . ?
C3A C2A C7A N1A -178.8(13) . . . . ?
C5A C6A C7A C2A 4(2) . . . . ?
C15A C6A C7A C2A 177.1(17) . . . . ?
C5A C6A C7A N1A -176.2(13) . . . . ?
C15A C6A C7A N1A -4(3) . . . . ?
O1A C1A N1A C7A -1(2) . . . . ?
C1'A C1A N1A C7A 175.5(18) . . . . ?
O1A C1A N1A In1A -176.4(8) . . . . ?
C1'A C1A N1A In1A 1(3) . . . . ?
C2A C7A N1A C1A 0.6(19) . . . . ?
C6A C7A N1A C1A -178.8(17) . . . . ?
C2A C7A N1A In1A 175.1(11) . . . . ?
C6A C7A N1A In1A -4(2) . . . . ?
C1A C1'A C8A N2A -16(4) . . . . ?
C1A C1'A C8A O2A 169.0(11) . . . . ?
N2A C8A O2A C9A -4(2) . . . . ?
C1'A C8A O2A C9A 171.8(16) . . . . ?
C8A O2A C9A C14A 2.3(19) . . . . ?
C8A O2A C9A C10A -176.6(16) . . . . ?
O2A C9A C10A C11A -176.5(14) . . . . ?
C14A C9A C10A C11A 5(3) . . . . ?
C9A C10A C11A C12A -6.6(19) . . . . ?
C10A C11A C12A C13A 3(2) . . . . ?
C11A C12A C13A C14A 4(2) . . . . ?
C11A C12A C13A C16A 175.9(14) . . . . ?
C12A C13A C14A C9A -6(2) . . . . ?
C16A C13A C14A C9A -178.0(16) . . . . ?
C12A C13A C14A N2A 178.0(15) . . . . ?
C16A C13A C14A N2A 6(3) . . . . ?
O2A C9A C14A C13A -177.3(14) . . . . ?
C10A C9A C14A C13A 2(3) . . . . ?
O2A C9A C14A N2A 0(2) . . . . ?
C10A C9A C14A N2A 178.7(15) . . . . ?
O2A C8A N2A C14A 4(2) . . . . ?
C1'A C8A N2A C14A -171.0(18) . . . . ?
O2A C8A N2A In1A -176.4(8) . . . . ?
C1'A C8A N2A In1A 9(3) . . . . ?
C13A C14A N2A C8A 174.4(18) . . . . ?
C9A C14A N2A C8A -2(2) . . . . ?
C13A C14A N2A In1A -5(3) . . . . ?
C9A C14A N2A In1A 177.9(11) . . . . ?
C8B C1'B C1B N1B 12.1 . . . . ?
C8B C1'B C1B O1B -176.1 . . . . ?
N1B C1B O1B C2B 0.7 . . . . ?
C1'B C1B O1B C2B -172.5 . . . . ?
C1B O1B C2B C7B -2.4 . . . . ?
C1B O1B C2B C3B -179.1 . . . . ?
O1B C2B C3B C4B 176.0 . . . . ?
C7B C2B C3B C4B -0.4 . . . . ?
C2B C3B C4B C5B -0.5 . . . . ?
C3B C4B C5B C6B 2.1 . . . . ?
C4B C5B C6B C7B -2.8 . . . . ?
C4B C5B C6B C15B 174.3 . . . . ?
C5B C6B C7B C2B 2.0 . . . . ?
C15B C6B C7B C2B -174.9 . . . . ?
C5B C6B C7B N1B -178.8 . . . . ?
C15B C6B C7B N1B 4.4 . . . . ?
O1B C2B C7B C6B -177.3 . . . . ?
C3B C2B C7B C6B -0.4 . . . . ?
O1B C2B C7B N1B 3.3 . . . . ?
C3B C2B C7B N1B -179.8 . . . . ?
C1'B C1B N1B C7B 173.3 . . . . ?
O1B C1B N1B C7B 1.3 . . . . ?
C1'B C1B N1B In1B -4.5 . . . . ?
O1B C1B N1B In1B -176.5 . . . . ?
C6B C7B N1B C1B 178.0 . . . . ?
C2B C7B N1B C1B -2.7 . . . . ?
C6B C7B N1B In1B -4.4 . . . . ?
C2B C7B N1B In1B 175.0 . . . . ?
C1B C1'B C8B N2B -15.2 . . . . ?
C1B C1'B C8B O2B 172.5 . . . . ?
N2B C8B O2B C9B 0.3 . . . . ?
C1'B C8B O2B C9B 174.1 . . . . ?
C8B O2B C9B C14B 0.9 . . . . ?
C8B O2B C9B C10B 177.7 . . . . ?
C14B C9B C10B C11B -1.2 . . . . ?
O2B C9B C10B C11B -177.4 . . . . ?
C9B C10B C11B C12B -1.4 . . . . ?
C10B C11B C12B C13B 1.5 . . . . ?
C11B C12B C13B C14B 1.0 . . . . ?
C11B C12B C13B C16B -175.7 . . . . ?
C10B C9B C14B C13B 3.8 . . . . ?
O2B C9B C14B C13B -179.4 . . . . ?
C10B C9B C14B N2B -178.5 . . . . ?
O2B C9B C14B N2B -1.7 . . . . ?
C12B C13B C14B C9B -3.4 . . . . ?
C16B C13B C14B C9B 173.4 . . . . ?
C12B C13B C14B N2B 179.4 . . . . ?
C16B C13B C14B N2B -3.7 . . . . ?
O2B C8B N2B C14B -1.3 . . . . ?
C1'B C8B N2B C14B -174.1 . . . . ?
O2B C8B N2B In1B -177.6 . . . . ?
C1'B C8B N2B In1B 9.6 . . . . ?
C9B C14B N2B C8B 1.8 . . . . ?
C13B C14B N2B C8B 179.2 . . . . ?
C9B C14B N2B In1B 177.8 . . . . ?
C13B C14B N2B In1B -4.9 . . . . ?
C8C C1'C C1C N1C 12.1 . . . . ?
C8C C1'C C1C O1C -176.1 . . . . ?
N1C C1C O1C C2C 0.7 . . . . ?
C1'C C1C O1C C2C -172.5 . . . . ?
C1C O1C C2C C7C -2.4 . . . . ?
C1C O1C C2C C3C -179.1 . . . . ?
O1C C2C C3C C4C 176.0 . . . . ?
C7C C2C C3C C4C -0.4 . . . . ?
C2C C3C C4C C5C -0.4 . . . . ?
C3C C4C C5C C6C 2.1 . . . . ?
C4C C5C C6C C7C -2.8 . . . . ?
C4C C5C C6C C15C 174.3 . . . . ?
C5C C6C C7C C2C 2.0 . . . . ?
C15C C6C C7C C2C -174.9 . . . . ?
C5C C6C C7C N1C -178.8 . . . . ?
C15C C6C C7C N1C 4.4 . . . . ?
O1C C2C C7C C6C -177.3 . . . . ?
C3C C2C C7C C6C -0.4 . . . . ?
O1C C2C C7C N1C 3.3 . . . . ?
C3C C2C C7C N1C -179.8 . . . . ?
C1'C C1C N1C C7C 173.3 . . . . ?
O1C C1C N1C C7C 1.3 . . . . ?
C1'C C1C N1C In1C -4.5 . . . . ?
O1C C1C N1C In1C -176.5 . . . . ?
C6C C7C N1C C1C 178.0 . . . . ?
C2C C7C N1C C1C -2.7 . . . . ?
C6C C7C N1C In1C -4.4 . . . . ?
C2C C7C N1C In1C 175.0 . . . . ?
C1C C1'C C8C N2C -15.2 . . . . ?
C1C C1'C C8C O2C 172.4 . . . . ?
N2C C8C O2C C9C 0.3 . . . . ?
C1'C C8C O2C C9C 174.1 . . . . ?
C8C O2C C9C C14C 0.9 . . . . ?
C8C O2C C9C C10C 177.7 . . . . ?
C14C C9C C10C C11C -1.2 . . . . ?
O2C C9C C10C C11C -177.4 . . . . ?
C9C C10C C11C C12C -1.4 . . . . ?
C10C C11C C12C C13C 1.5 . . . . ?
C11C C12C C13C C14C 1.0 . . . . ?
C11C C12C C13C C16C -175.7 . . . . ?
C10C C9C C14C C13C 3.8 . . . . ?
O2C C9C C14C C13C -179.4 . . . . ?
C10C C9C C14C N2C -178.4 . . . . ?
O2C C9C C14C N2C -1.7 . . . . ?
C12C C13C C14C C9C -3.4 . . . . ?
C16C C13C C14C C9C 173.4 . . . . ?
C12C C13C C14C N2C 179.4 . . . . ?
C16C C13C C14C N2C -3.7 . . . . ?
O2C C8C N2C C14C -1.3 . . . . ?
C1'C C8C N2C C14C -174.1 . . . . ?
O2C C8C N2C In1C -177.6 . . . . ?
C1'C C8C N2C In1C 9.6 . . . . ?
C9C C14C N2C C8C 1.8 . . . . ?
C13C C14C N2C C8C 179.2 . . . . ?
C9C C14C N2C In1C 177.8 . . . . ?
C13C C14C N2C In1C -4.9 . . . . ?

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.065

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Oxygen-sensitive'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5_mbox2CHAlMeCl
_database_code_depnum_ccdc_archive 'CCDC 1429341'
_audit_update_record             
;
2015-10-03 deposited with the CCDC.
2015-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'Chloro methyl aluminium bis-(4-methylbenzoxazol-2-yl)-methanide'
_chemical_name_common            '[ClMeAl{(4-Me-NCOC6H3)2CH}]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C18.11 H16.32 Al Cl0.89 N2 O2'
_chemical_formula_sum            'C18.11 H16.32 Al Cl0.89 N2 O2'
_chemical_formula_weight         352.59

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'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Al Al 0.0406 0.0313 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.0998 0.0984 '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                   7.982(2)
_cell_length_b                   14.727(3)
_cell_length_c                   13.890(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.73(2)
_cell_angle_gamma                90
_cell_volume                     1632.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5105
_cell_measurement_theta_min      2.291
_cell_measurement_theta_max      19.367

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             733
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    0.153
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7112
_exptl_absorpt_correction_T_max  0.7444
_exptl_absorpt_process_details   SADABS-2014/4

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.56086
_diffrn_radiation_type           AgK\a
_diffrn_source                   'INCOATEC Microsource'
_diffrn_measurement_device_type  'Bruker Smart APEX II Quazar'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20579
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.591
_diffrn_reflns_theta_max         19.579
_diffrn_reflns_theta_full        19.665
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2904
_reflns_number_gt                2398
_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       'APEX2 v2012.2'
_computing_cell_refinement       'SAINT V8.34A'
_computing_data_reduction        'SAINT V8.34A'
_computing_structure_solution    'SHELXS-2012 (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'

_refine_special_details          'Cl Me disorder'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.4255P] 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         2904
_refine_ls_number_parameters     243
_refine_ls_number_restraints     290
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.018
_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 -0.1564(2) 0.22933(11) 0.38146(13) 0.0235(4) Uani 1 1 d D U . . .
H1' H -0.2746 0.2220 0.3827 0.028 Uiso 1 1 calc R U . . .
C1 C -0.0552(2) 0.15340(11) 0.38149(12) 0.0203(4) Uani 1 1 d D U . . .
O1 O -0.12815(14) 0.07024(7) 0.38088(8) 0.0233(3) Uani 1 1 d D U . . .
C2 C 0.0016(2) 0.00754(11) 0.37862(11) 0.0198(4) Uani 1 1 d D U . . .
C3 C -0.0148(2) -0.08517(11) 0.37513(12) 0.0241(4) Uani 1 1 d D U . . .
H3 H -0.1207 -0.1146 0.3752 0.029 Uiso 1 1 calc R U . . .
C4 C 0.1353(2) -0.13264(11) 0.37149(12) 0.0257(4) Uani 1 1 d D U . . .
H4 H 0.1334 -0.1971 0.3686 0.031 Uiso 1 1 calc R U . . .
C5 C 0.2879(2) -0.08756(12) 0.37206(12) 0.0232(4) Uani 1 1 d D U . . .
H5 H 0.3874 -0.1228 0.3696 0.028 Uiso 1 1 calc R U . . .
C6 C 0.3031(2) 0.00722(11) 0.37607(11) 0.0195(4) Uani 1 1 d D U . . .
C7 C 0.1519(2) 0.05430(10) 0.37873(11) 0.0179(4) Uani 1 1 d D U . . .
C15 C 0.4727(2) 0.05108(12) 0.37697(13) 0.0265(4) Uani 1 1 d D U . . .
H15A H 0.4817 0.0899 0.3201 0.040 Uiso 1 1 calc R U . . .
H15B H 0.5594 0.0040 0.3761 0.040 Uiso 1 1 calc R U . . .
H15C H 0.4877 0.0880 0.4353 0.040 Uiso 1 1 calc R U . . .
N1 N 0.11360(17) 0.14858(9) 0.38097(9) 0.0179(3) Uani 1 1 d D U . . .
Al1 Al 0.25152(6) 0.25458(3) 0.37963(3) 0.01718(16) Uani 1 1 d D U . . .
Cl1 Cl 0.3710(5) 0.2612(3) 0.2478(3) 0.0211(6) Uani 0.452(5) 1 d D U P A 1
C1M C 0.3987(19) 0.2640(9) 0.4969(9) 0.025(3) Uani 0.552(11) 1 d D U P A 1
H1MA H 0.5128 0.2792 0.4785 0.037 Uiso 0.552(11) 1 calc R U P A 1
H1MB H 0.3997 0.2058 0.5312 0.037 Uiso 0.552(11) 1 calc R U P A 1
H1MC H 0.3562 0.3115 0.5391 0.037 Uiso 0.552(11) 1 calc R U P A 1
C1M' C 0.3835(19) 0.2638(10) 0.2611(9) 0.025(3) Uani 0.554(11) 1 d D U P A 2
H1MD H 0.3758 0.2064 0.2254 0.037 Uiso 0.554(11) 1 calc R U P A 2
H1ME H 0.5011 0.2763 0.2787 0.037 Uiso 0.554(11) 1 calc R U P A 2
H1MF H 0.3388 0.3132 0.2206 0.037 Uiso 0.554(11) 1 calc R U P A 2
Cl1' Cl 0.3904(6) 0.2612(3) 0.5099(3) 0.0208(6) Uani 0.441(5) 1 d D U P A 2
C8 C -0.0896(2) 0.31574(11) 0.37969(11) 0.0193(4) Uani 1 1 d D U . . .
O2 O -0.19483(14) 0.38794(7) 0.37784(8) 0.0220(3) Uani 1 1 d D U . . .
C9 C -0.0939(2) 0.46431(11) 0.37484(11) 0.0198(4) Uani 1 1 d D U . . .
C10 C -0.1478(2) 0.55283(11) 0.37088(12) 0.0258(4) Uani 1 1 d D U . . .
H10 H -0.2633 0.5686 0.3697 0.031 Uiso 1 1 calc R U . . .
C11 C -0.0217(2) 0.61753(11) 0.36873(12) 0.0260(4) Uani 1 1 d D U . . .
H11 H -0.0506 0.6801 0.3663 0.031 Uiso 1 1 calc R U . . .
C12 C 0.1461(2) 0.59252(11) 0.37004(12) 0.0241(4) Uani 1 1 d D U . . .
H12 H 0.2285 0.6390 0.3683 0.029 Uiso 1 1 calc R U . . .
C13 C 0.1995(2) 0.50209(11) 0.37381(11) 0.0201(4) Uani 1 1 d D U . . .
C14 C 0.0717(2) 0.43714(11) 0.37571(11) 0.0181(4) Uani 1 1 d D U . . .
C16 C 0.3830(2) 0.47896(12) 0.37518(13) 0.0288(4) Uani 1 1 d D U . . .
H16A H 0.4092 0.4464 0.3160 0.043 Uiso 1 1 calc R U . . .
H16B H 0.4101 0.4405 0.4310 0.043 Uiso 1 1 calc R U . . .
H16C H 0.4492 0.5349 0.3794 0.043 Uiso 1 1 calc R U . . .
N2 N 0.07303(17) 0.34084(9) 0.37885(9) 0.0176(3) Uani 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1' C1 1.379(2) . ?
C1' C8 1.380(2) . ?
C1 N1 1.349(2) . ?
C1 O1 1.3560(19) . ?
O1 C2 1.389(2) . ?
C2 C3 1.372(2) . ?
C2 C7 1.383(2) . ?
C3 C4 1.390(3) . ?
C4 C5 1.387(2) . ?
C5 C6 1.402(2) . ?
C6 C7 1.394(2) . ?
C6 C15 1.499(2) . ?
C7 N1 1.422(2) . ?
N1 Al1 1.9107(14) . ?
Al1 N2 1.9086(14) . ?
Al1 C1M 1.984(11) . ?
Al1 C1M' 1.986(11) . ?
Al1 Cl1 2.092(4) . ?
Al1 Cl1' 2.096(4) . ?
C8 N2 1.350(2) . ?
C8 O2 1.3548(19) . ?
O2 C9 1.385(2) . ?
C9 C10 1.373(2) . ?
C9 C14 1.381(2) . ?
C10 C11 1.387(2) . ?
C11 C12 1.389(3) . ?
C12 C13 1.399(2) . ?
C13 C14 1.399(2) . ?
C13 C16 1.503(2) . ?
C14 N2 1.419(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C1' C8 121.39(16) . . ?
N1 C1 O1 112.40(14) . . ?
N1 C1 C1' 128.86(15) . . ?
O1 C1 C1' 118.73(15) . . ?
C1 O1 C2 106.27(12) . . ?
C3 C2 C7 125.26(16) . . ?
C3 C2 O1 126.29(15) . . ?
C7 C2 O1 108.44(14) . . ?
C2 C3 C4 114.85(16) . . ?
C5 C4 C3 121.13(16) . . ?
C4 C5 C6 123.49(17) . . ?
C7 C6 C5 114.99(16) . . ?
C7 C6 C15 124.61(15) . . ?
C5 C6 C15 120.41(16) . . ?
C2 C7 C6 120.27(15) . . ?
C2 C7 N1 107.42(14) . . ?
C6 C7 N1 132.31(15) . . ?
C1 N1 C7 105.47(13) . . ?
C1 N1 Al1 122.19(11) . . ?
C7 N1 Al1 132.32(11) . . ?
N2 Al1 N1 96.52(6) . . ?
N2 Al1 C1M 112.4(4) . . ?
N1 Al1 C1M 112.1(4) . . ?
N2 Al1 C1M' 111.4(4) . . ?
N1 Al1 C1M' 112.6(4) . . ?
N2 Al1 Cl1 108.91(13) . . ?
N1 Al1 Cl1 108.93(13) . . ?
C1M Al1 Cl1 116.2(5) . . ?
N2 Al1 Cl1' 110.45(13) . . ?
N1 Al1 Cl1' 108.63(13) . . ?
C1M' Al1 Cl1' 115.6(5) . . ?
N2 C8 O2 112.37(14) . . ?
N2 C8 C1' 128.65(15) . . ?
O2 C8 C1' 118.98(15) . . ?
C8 O2 C9 106.09(12) . . ?
C10 C9 C14 125.05(16) . . ?
C10 C9 O2 126.16(15) . . ?
C14 C9 O2 108.79(14) . . ?
C9 C10 C11 115.21(17) . . ?
C10 C11 C12 121.19(16) . . ?
C11 C12 C13 123.09(16) . . ?
C12 C13 C14 115.45(16) . . ?
C12 C13 C16 120.80(15) . . ?
C14 C13 C16 123.75(15) . . ?
C9 C14 C13 120.01(15) . . ?
C9 C14 N2 107.23(14) . . ?
C13 C14 N2 132.77(16) . . ?
C8 N2 C14 105.53(13) . . ?
C8 N2 Al1 122.38(11) . . ?
C14 N2 Al1 132.09(11) . . ?

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 C1' C1 N1 0.8(3) . . . . ?
C8 C1' C1 O1 -178.40(15) . . . . ?
N1 C1 O1 C2 -0.77(18) . . . . ?
C1' C1 O1 C2 178.53(15) . . . . ?
C1 O1 C2 C3 -178.44(16) . . . . ?
C1 O1 C2 C7 0.51(17) . . . . ?
C7 C2 C3 C4 0.0(3) . . . . ?
O1 C2 C3 C4 178.76(15) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
C4 C5 C6 C15 179.67(16) . . . . ?
C3 C2 C7 C6 -0.6(3) . . . . ?
O1 C2 C7 C6 -179.59(14) . . . . ?
C3 C2 C7 N1 178.87(15) . . . . ?
O1 C2 C7 N1 -0.09(17) . . . . ?
C5 C6 C7 C2 0.8(2) . . . . ?
C15 C6 C7 C2 -179.33(15) . . . . ?
C5 C6 C7 N1 -178.51(15) . . . . ?
C15 C6 C7 N1 1.3(3) . . . . ?
O1 C1 N1 C7 0.71(18) . . . . ?
C1' C1 N1 C7 -178.51(17) . . . . ?
O1 C1 N1 Al1 179.02(10) . . . . ?
C1' C1 N1 Al1 -0.2(2) . . . . ?
C2 C7 N1 C1 -0.36(17) . . . . ?
C6 C7 N1 C1 179.06(17) . . . . ?
C2 C7 N1 Al1 -178.43(11) . . . . ?
C6 C7 N1 Al1 1.0(3) . . . . ?
C1 C1' C8 N2 -0.8(3) . . . . ?
C1 C1' C8 O2 178.73(15) . . . . ?
N2 C8 O2 C9 0.50(17) . . . . ?
C1' C8 O2 C9 -179.09(15) . . . . ?
C8 O2 C9 C10 179.05(16) . . . . ?
C8 O2 C9 C14 -0.48(17) . . . . ?
C14 C9 C10 C11 -0.7(3) . . . . ?
O2 C9 C10 C11 179.83(15) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C11 C12 C13 C16 -179.93(16) . . . . ?
C10 C9 C14 C13 0.9(3) . . . . ?
O2 C9 C14 C13 -179.55(14) . . . . ?
C10 C9 C14 N2 -179.24(15) . . . . ?
O2 C9 C14 N2 0.30(17) . . . . ?
C12 C13 C14 C9 -0.7(2) . . . . ?
C16 C13 C14 C9 179.61(16) . . . . ?
C12 C13 C14 N2 179.54(16) . . . . ?
C16 C13 C14 N2 -0.2(3) . . . . ?
O2 C8 N2 C14 -0.32(17) . . . . ?
C1' C8 N2 C14 179.22(16) . . . . ?
O2 C8 N2 Al1 -179.32(10) . . . . ?
C1' C8 N2 Al1 0.2(2) . . . . ?
C9 C14 N2 C8 0.00(17) . . . . ?
C13 C14 N2 C8 179.82(17) . . . . ?
C9 C14 N2 Al1 178.87(11) . . . . ?
C13 C14 N2 Al1 -1.3(3) . . . . ?

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Oxygen-sensitive'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6_mbox2CHAlMeI
_database_code_depnum_ccdc_archive 'CCDC 1429342'
_audit_update_record             
;
2015-10-03 deposited with the CCDC.
2015-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'Iodo methyl aluminium bis-(4-methylbenzoxazol-2-yl)-methanide'
_chemical_name_common            '[MeIAl{(4-Me-NCOC6H3)2CH}]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 Al I N2 O2'
_chemical_formula_sum            'C18 H16 Al I N2 O2'
_chemical_formula_weight         446.21

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'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Al Al 0.0406 0.0313 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.8919 1.1868 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_H-M_alt        'P b c m'
_space_group_name_Hall           '-P 2c 2b'

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

_cell_length_a                   8.015(2)
_cell_length_b                   13.868(2)
_cell_length_c                   15.566(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1730.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7344
_cell_measurement_theta_min      2.316
_cell_measurement_theta_max      20.487

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.069
_exptl_absorpt_coefficient_mu    1.019
_shelx_estimated_absorpt_T_min   0.855
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6987
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_process_details   SADABS-2014/4

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.56086
_diffrn_radiation_type           AgK\a
_diffrn_source                   'INCOATEC Microsource'
_diffrn_measurement_device_type  'Bruker Smart APEX II Quazar'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25400
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.005
_diffrn_reflns_theta_max         20.793
_diffrn_reflns_theta_full        19.665
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1915
_reflns_number_gt                1665
_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       'APEX2 v2012.2'
_computing_cell_refinement       'SAINT V8.34A'
_computing_data_reduction        'SAINT V8.34A'
_computing_structure_solution    'SHELXT (Sheldrick,Acta Cryst.(2015)A71,3-8)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'

_refine_special_details          'I Me disorder'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0241P)²+2.0659P] 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         1915
_refine_ls_number_parameters     118
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0222
_refine_ls_wR_factor_ref         0.0542
_refine_ls_wR_factor_gt          0.0516
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.147
_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 0.6627(4) 0.6317(2) 0.2500 0.0167(7) Uani 1 2 d S T P . .
H1' H 0.7812 0.6337 0.2500 0.020 Uiso 1 2 calc R U P . .
C1 C 0.5781(3) 0.63028(16) 0.32754(14) 0.0141(5) Uani 1 1 d . . . . .
O1 O 0.6693(2) 0.63133(12) 0.40130(10) 0.0166(3) Uani 1 1 d . . . . .
C2 C 0.5546(3) 0.62719(16) 0.46775(14) 0.0156(5) Uani 1 1 d . . . . .
C3 C 0.5906(3) 0.62434(17) 0.55420(15) 0.0202(5) Uani 1 1 d . . . . .
H3 H 0.7017 0.6266 0.5754 0.024 Uiso 1 1 calc R U . . .
C4 C 0.4533(3) 0.61789(18) 0.60803(15) 0.0236(6) Uani 1 1 d . . . . .
H4 H 0.4700 0.6151 0.6684 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2929(3) 0.61545(17) 0.57574(15) 0.0209(5) Uani 1 1 d . . . . .
H5 H 0.2029 0.6106 0.6152 0.025 Uiso 1 1 calc R U . . .
C6 C 0.2558(3) 0.61972(16) 0.48755(14) 0.0162(5) Uani 1 1 d . . . . .
C7 C 0.3945(3) 0.62498(15) 0.43348(14) 0.0139(5) Uani 1 1 d . . . . .
C15 C 0.0775(3) 0.62082(19) 0.45784(16) 0.0234(6) Uani 1 1 d . . . . .
H15A H 0.0485 0.6856 0.4377 0.035 Uiso 1 1 calc R U . . .
H15B H 0.0043 0.6029 0.5057 0.035 Uiso 1 1 calc R U . . .
H15C H 0.0634 0.5746 0.4108 0.035 Uiso 1 1 calc R U . . .
N1 N 0.4125(2) 0.62729(13) 0.34243(12) 0.0129(4) Uani 1 1 d D . . . .
Al1 Al 0.25617(12) 0.62289(7) 0.2500 0.0122(2) Uani 1 2 d DS T P . .
I1 I 0.12718(3) 0.45514(2) 0.2500 0.01691(8) Uani 0.9718(7) 2 d DS T P A 1
C1M C 0.1047(6) 0.7294(3) 0.2500 0.01691(8) Uani 0.9718(7) 2 d DS T P A 1
H1MA H 0.0537 0.7357 0.3069 0.025 Uiso 0.4859(4) 1 calc R U P A 1
H1MB H 0.0174 0.7184 0.2070 0.025 Uiso 0.4859(4) 1 calc R U P A 1
H1MC H 0.1654 0.7887 0.2360 0.025 Uiso 0.4859(4) 1 calc R U P A 1
I1' I 0.0763(12) 0.7481(6) 0.2500 0.01691(8) Uani 0.0282(7) 2 d DS T P A 2
C1M' C 0.177(7) 0.4894(18) 0.2500 0.01691(8) Uani 0.0282(7) 2 d DS T P A 2
H1M1 H 0.0953 0.4807 0.2961 0.025 Uiso 0.0141(4) 1 calc R U P A 2
H1M2 H 0.2717 0.4458 0.2593 0.025 Uiso 0.0141(4) 1 calc R U P A 2
H1M3 H 0.1249 0.4748 0.1946 0.025 Uiso 0.0141(4) 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' C1 1.384(3) 6_556 ?
C1' C1 1.384(3) . ?
C1 N1 1.348(3) . ?
C1 O1 1.361(3) . ?
O1 C2 1.385(3) . ?
C2 C3 1.377(3) . ?
C2 C7 1.390(3) . ?
C3 C4 1.386(4) . ?
C4 C5 1.381(4) . ?
C5 C6 1.406(3) . ?
C6 C7 1.396(3) . ?
C6 C15 1.502(3) . ?
C7 N1 1.425(3) . ?
N1 Al1 1.909(2) . ?
Al1 N1 1.909(2) 6_556 ?
Al1 C1M 1.912(4) . ?
Al1 C1M' 1.957(18) . ?
Al1 I1' 2.256(8) . ?
Al1 I1 2.5458(11) . ?

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 C1' C1 121.4(3) 6_556 . ?
N1 C1 O1 112.58(19) . . ?
N1 C1 C1' 129.2(2) . . ?
O1 C1 C1' 118.2(2) . . ?
C1 O1 C2 105.85(17) . . ?
C3 C2 O1 126.3(2) . . ?
C3 C2 C7 124.6(2) . . ?
O1 C2 C7 109.09(18) . . ?
C2 C3 C4 115.2(2) . . ?
C5 C4 C3 121.4(2) . . ?
C4 C5 C6 123.4(2) . . ?
C7 C6 C5 115.0(2) . . ?
C7 C6 C15 124.8(2) . . ?
C5 C6 C15 120.1(2) . . ?
C2 C7 C6 120.3(2) . . ?
C2 C7 N1 106.75(19) . . ?
C6 C7 N1 132.9(2) . . ?
C1 N1 C7 105.73(18) . . ?
C1 N1 Al1 121.18(15) . . ?
C7 N1 Al1 133.06(16) . . ?
N1 Al1 N1 97.84(12) . 6_556 ?
N1 Al1 C1M 113.08(10) . . ?
N1 Al1 C1M 113.08(10) 6_556 . ?
N1 Al1 C1M' 104.0(11) . . ?
N1 Al1 C1M' 104.0(11) 6_556 . ?
N1 Al1 I1' 113.25(16) . . ?
N1 Al1 I1' 113.25(16) 6_556 . ?
C1M' Al1 I1' 121.4(17) . . ?
N1 Al1 I1 107.20(6) . . ?
N1 Al1 I1 107.20(6) 6_556 . ?
C1M Al1 I1 116.63(14) . . ?

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
C1 C1' C1 N1 0.2(5) 6_556 . . . ?
C1 C1' C1 O1 179.68(19) 6_556 . . . ?
N1 C1 O1 C2 1.0(2) . . . . ?
C1' C1 O1 C2 -178.6(2) . . . . ?
C1 O1 C2 C3 178.4(2) . . . . ?
C1 O1 C2 C7 -0.8(2) . . . . ?
O1 C2 C3 C4 -178.4(2) . . . . ?
C7 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C4 C5 C6 C15 -177.5(2) . . . . ?
C3 C2 C7 C6 0.2(4) . . . . ?
O1 C2 C7 C6 179.3(2) . . . . ?
C3 C2 C7 N1 -178.9(2) . . . . ?
O1 C2 C7 N1 0.3(2) . . . . ?
C5 C6 C7 C2 -1.0(3) . . . . ?
C15 C6 C7 C2 177.5(2) . . . . ?
C5 C6 C7 N1 177.7(2) . . . . ?
C15 C6 C7 N1 -3.8(4) . . . . ?
O1 C1 N1 C7 -0.8(3) . . . . ?
C1' C1 N1 C7 178.8(3) . . . . ?
O1 C1 N1 Al1 -178.86(14) . . . . ?
C1' C1 N1 Al1 0.7(4) . . . . ?
C2 C7 N1 C1 0.2(2) . . . . ?
C6 C7 N1 C1 -178.6(2) . . . . ?
C2 C7 N1 Al1 178.00(17) . . . . ?
C6 C7 N1 Al1 -0.8(4) . . . . ?

_refine_diff_density_max         0.502
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.083

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Oxygen-sensitive'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_7_mbox2CHAlEtI
_database_code_depnum_ccdc_archive 'CCDC 1429343'
_audit_update_record             
;
2015-10-03 deposited with the CCDC.
2015-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'Iodo ethyl aluminium bis-(4-methylbenzoxazol-2-yl)-methanide'
_chemical_name_common            '[EtI{(4-Me-NCOC6H3)2CH}]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 Al I N2 O2'
_chemical_formula_sum            'C19 H18 Al I N2 O2'
_chemical_formula_weight         460.23

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'
I I -0.4742 1.8119 '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                   9.102(3)
_cell_length_b                   7.647(2)
_cell_length_c                   26.711(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.59(2)
_cell_angle_gamma                90
_cell_volume                     1846.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9995
_cell_measurement_theta_min      2.2525
_cell_measurement_theta_max      27.85

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.796
_shelx_estimated_absorpt_T_min   0.772
_shelx_estimated_absorpt_T_max   0.855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6996
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS-2014/4

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'INCOATEC Microsource'
_diffrn_measurement_device_type  'Bruker Smart APEX II Quazar'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38660
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.535
_diffrn_reflns_theta_max         27.884
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4398
_reflns_number_gt                4066
_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       'APEX2 v2012.2'
_computing_cell_refinement       'SAINT V8.34A'
_computing_data_reduction        'SAINT V8.34A'
_computing_structure_solution    'SHELXT (Sheldrick,Acta Cryst.(2015)A71,3-8)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'

_refine_special_details          'I Et disorder'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0255P)²+1.2530P] 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         4398
_refine_ls_number_parameters     257
_refine_ls_number_restraints     349
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0210
_refine_ls_wR_factor_ref         0.0534
_refine_ls_wR_factor_gt          0.0520
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1' C 0.3154(2) 0.8674(2) 0.46033(6) 0.0222(3) Uani 1 1 d D U . . .
H1' H 0.3419 0.9335 0.4901 0.027 Uiso 1 1 calc R U . . .
C1 C 0.41330(19) 0.8571(2) 0.42457(6) 0.0192(3) Uani 1 1 d D U . . .
O1 O 0.54146(13) 0.94856(16) 0.43220(4) 0.0218(2) Uani 1 1 d D U . . .
C2 C 0.61419(19) 0.9205(2) 0.39031(6) 0.0207(3) Uani 1 1 d D U . . .
C3 C 0.7480(2) 0.9902(2) 0.38200(7) 0.0259(4) Uani 1 1 d D U . . .
H3 H 0.8032 1.0645 0.4057 0.031 Uiso 1 1 calc R U . . .
C4 C 0.7973(2) 0.9444(3) 0.33636(7) 0.0271(4) Uani 1 1 d D U . . .
H4 H 0.8886 0.9897 0.3280 0.032 Uiso 1 1 calc R U . . .
C5 C 0.71483(19) 0.8332(2) 0.30266(7) 0.0237(4) Uani 1 1 d D U . . .
H5 H 0.7525 0.8053 0.2719 0.028 Uiso 1 1 calc R U . . .
C6 C 0.57913(18) 0.7604(2) 0.31189(6) 0.0200(3) Uani 1 1 d D U . . .
C7 C 0.52919(18) 0.8095(2) 0.35744(6) 0.0179(3) Uani 1 1 d D U . . .
N1 N 0.39983(15) 0.76868(19) 0.38045(5) 0.0174(3) Uani 1 1 d D U . . .
C15 C 0.4992(2) 0.6367(3) 0.27455(7) 0.0260(4) Uani 1 1 d D U . . .
H15A H 0.3967 0.6757 0.2663 0.039 Uiso 1 1 calc R U . . .
H15B H 0.5001 0.5190 0.2891 0.039 Uiso 1 1 calc R U . . .
H15C H 0.5485 0.6345 0.2438 0.039 Uiso 1 1 calc R U . . .
Al1 Al 0.22974(5) 0.62851(7) 0.35981(2) 0.01660(11) Uani 1 1 d D U . . .
C1M C 0.1270(2) 0.7057(3) 0.29599(7) 0.0199(4) Uani 0.9229(7) 1 d D U P A 1
H1MA H 0.1576 0.6321 0.2685 0.024 Uiso 0.9229(7) 1 calc R U P A 1
H1MB H 0.0191 0.6907 0.2965 0.024 Uiso 0.9229(7) 1 calc R U P A 1
C2M C 0.1610(3) 0.9008(4) 0.28541(9) 0.0310(5) Uani 0.9229(7) 1 d D U P A 1
H2MA H 0.1426 0.9721 0.3145 0.046 Uiso 0.9229(7) 1 calc R U P A 1
H2MB H 0.0969 0.9405 0.2556 0.046 Uiso 0.9229(7) 1 calc R U P A 1
H2MC H 0.2647 0.9126 0.2794 0.046 Uiso 0.9229(7) 1 calc R U P A 1
I1 I 0.31991(2) 0.31044(2) 0.36725(2) 0.02534(5) Uani 0.9229(7) 1 d D U P A 1
C1M' C 0.248(2) 0.3787(18) 0.3518(8) 0.022(2) Uani 0.0771(7) 1 d D U P A 2
H1MC H 0.1857 0.3206 0.3748 0.027 Uiso 0.0771(7) 1 calc R U P A 2
H1MD H 0.2074 0.3480 0.3169 0.027 Uiso 0.0771(7) 1 calc R U P A 2
C2M' C 0.407(3) 0.301(3) 0.3617(11) 0.036(3) Uani 0.0771(7) 1 d D U P A 2
H2MD H 0.4024 0.1740 0.3565 0.055 Uiso 0.0771(7) 1 calc R U P A 2
H2ME H 0.4480 0.3260 0.3965 0.055 Uiso 0.0771(7) 1 calc R U P A 2
H2MF H 0.4697 0.3535 0.3384 0.055 Uiso 0.0771(7) 1 calc R U P A 2
I1' I 0.1136(2) 0.8068(3) 0.28035(6) 0.0298(7) Uani 0.0771(7) 1 d D U P A 2
C8 C 0.1801(2) 0.7840(2) 0.45382(6) 0.0206(3) Uani 1 1 d D U . . .
O2 O 0.08692(14) 0.80763(16) 0.48944(4) 0.0241(3) Uani 1 1 d D U . . .
C9 C -0.0380(2) 0.7104(2) 0.47379(7) 0.0236(4) Uani 1 1 d D U . . .
C10 C -0.1611(2) 0.6949(3) 0.49915(7) 0.0292(4) Uani 1 1 d D U . . .
H10 H -0.1697 0.7538 0.5300 0.035 Uiso 1 1 calc R U . . .
C11 C -0.2712(2) 0.5871(3) 0.47636(8) 0.0320(4) Uani 1 1 d D U . . .
H11 H -0.3588 0.5703 0.4919 0.038 Uiso 1 1 calc R U . . .
C12 C -0.2558(2) 0.5023(3) 0.43078(8) 0.0304(4) Uani 1 1 d D U . . .
H12 H -0.3342 0.4297 0.4164 0.036 Uiso 1 1 calc R U . . .
C13 C -0.1297(2) 0.5198(2) 0.40538(7) 0.0251(4) Uani 1 1 d D U . . .
C14 C -0.01958(19) 0.6283(2) 0.42855(6) 0.0203(3) Uani 1 1 d D U . . .
N2 N 0.12273(16) 0.67935(18) 0.41582(5) 0.0185(3) Uani 1 1 d D U . . .
C16 C -0.1205(2) 0.4265(3) 0.35649(8) 0.0329(4) Uani 1 1 d D U . . .
H16A H -0.2054 0.3478 0.3496 0.049 Uiso 1 1 calc R U . . .
H16B H -0.0288 0.3584 0.3587 0.049 Uiso 1 1 calc R U . . .
H16C H -0.1213 0.5122 0.3292 0.049 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' C8 1.380(3) . ?
C1' C1 1.381(2) . ?
C1 N1 1.352(2) . ?
C1 O1 1.355(2) . ?
O1 C2 1.381(2) . ?
C2 C3 1.371(2) . ?
C2 C7 1.390(2) . ?
C3 C4 1.391(3) . ?
C4 C5 1.394(3) . ?
C5 C6 1.402(2) . ?
C6 C7 1.398(2) . ?
C6 C15 1.501(2) . ?
C7 N1 1.424(2) . ?
N1 Al1 1.9115(16) . ?
Al1 N2 1.9164(15) . ?
Al1 C1M' 1.932(14) . ?
Al1 C1M 1.940(2) . ?
Al1 I1 2.5674(8) . ?
Al1 I1' 2.639(2) . ?
C1M C2M 1.556(4) . ?
C1M' C2M' 1.555(18) . ?
C8 N2 1.350(2) . ?
C8 O2 1.357(2) . ?
O2 C9 1.383(2) . ?
C9 C10 1.379(3) . ?
C9 C14 1.389(2) . ?
C10 C11 1.383(3) . ?
C11 C12 1.401(3) . ?
C12 C13 1.406(2) . ?
C13 C14 1.390(3) . ?
C13 C16 1.499(3) . ?
C14 N2 1.431(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C1' C1 121.56(15) . . ?
N1 C1 O1 112.30(14) . . ?
N1 C1 C1' 129.08(16) . . ?
O1 C1 C1' 118.60(15) . . ?
C1 O1 C2 106.39(13) . . ?
C3 C2 O1 126.02(16) . . ?
C3 C2 C7 125.14(16) . . ?
O1 C2 C7 108.83(14) . . ?
C2 C3 C4 115.17(17) . . ?
C3 C4 C5 121.07(17) . . ?
C4 C5 C6 123.27(17) . . ?
C7 C6 C5 115.30(16) . . ?
C7 C6 C15 124.49(15) . . ?
C5 C6 C15 120.20(15) . . ?
C2 C7 C6 120.02(15) . . ?
C2 C7 N1 106.80(14) . . ?
C6 C7 N1 133.18(15) . . ?
C1 N1 C7 105.66(14) . . ?
C1 N1 Al1 121.41(12) . . ?
C7 N1 Al1 132.91(11) . . ?
N1 Al1 N2 97.38(7) . . ?
N1 Al1 C1M' 120.6(6) . . ?
N2 Al1 C1M' 110.2(6) . . ?
N1 Al1 C1M 112.07(8) . . ?
N2 Al1 C1M 112.79(8) . . ?
N1 Al1 I1 105.53(5) . . ?
N2 Al1 I1 108.56(5) . . ?
C1M Al1 I1 118.28(7) . . ?
N1 Al1 I1' 100.29(7) . . ?
N2 Al1 I1' 109.30(6) . . ?
C1M' Al1 I1' 117.0(6) . . ?
C2M C1M Al1 111.44(14) . . ?
C2M' C1M' Al1 116.8(14) . . ?
N2 C8 O2 112.77(15) . . ?
N2 C8 C1' 129.16(15) . . ?
O2 C8 C1' 118.07(15) . . ?
C8 O2 C9 105.96(13) . . ?
C10 C9 O2 125.75(17) . . ?
C10 C9 C14 125.06(18) . . ?
O2 C9 C14 109.19(15) . . ?
C9 C10 C11 115.04(18) . . ?
C10 C11 C12 121.28(17) . . ?
C11 C12 C13 122.94(19) . . ?
C14 C13 C12 115.41(17) . . ?
C14 C13 C16 124.24(16) . . ?
C12 C13 C16 120.35(18) . . ?
C9 C14 C13 120.28(16) . . ?
C9 C14 N2 106.65(15) . . ?
C13 C14 N2 133.07(16) . . ?
C8 N2 C14 105.41(14) . . ?
C8 N2 Al1 121.33(12) . . ?
C14 N2 Al1 133.26(12) . . ?

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 C1' C1 N1 -1.4(3) . . . . ?
C8 C1' C1 O1 177.00(16) . . . . ?
N1 C1 O1 C2 1.04(18) . . . . ?
C1' C1 O1 C2 -177.64(15) . . . . ?
C1 O1 C2 C3 179.24(17) . . . . ?
C1 O1 C2 C7 -0.56(18) . . . . ?
O1 C2 C3 C4 -178.96(16) . . . . ?
C7 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C4 C5 C6 C15 -177.90(17) . . . . ?
C3 C2 C7 C6 0.3(3) . . . . ?
O1 C2 C7 C6 -179.92(14) . . . . ?
C3 C2 C7 N1 -179.88(16) . . . . ?
O1 C2 C7 N1 -0.07(18) . . . . ?
C5 C6 C7 C2 -1.2(2) . . . . ?
C15 C6 C7 C2 177.75(16) . . . . ?
C5 C6 C7 N1 179.01(17) . . . . ?
C15 C6 C7 N1 -2.1(3) . . . . ?
O1 C1 N1 C7 -1.08(18) . . . . ?
C1' C1 N1 C7 177.43(17) . . . . ?
O1 C1 N1 Al1 -179.92(10) . . . . ?
C1' C1 N1 Al1 -1.4(3) . . . . ?
C2 C7 N1 C1 0.68(17) . . . . ?
C6 C7 N1 C1 -179.50(18) . . . . ?
C2 C7 N1 Al1 179.32(12) . . . . ?
C6 C7 N1 Al1 -0.9(3) . . . . ?
C1 C1' C8 N2 2.7(3) . . . . ?
C1 C1' C8 O2 -176.72(16) . . . . ?
N2 C8 O2 C9 0.72(18) . . . . ?
C1' C8 O2 C9 -179.80(15) . . . . ?
C8 O2 C9 C10 179.18(17) . . . . ?
C8 O2 C9 C14 -0.03(18) . . . . ?
O2 C9 C10 C11 -178.77(16) . . . . ?
C14 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C11 C12 C13 C16 -179.57(18) . . . . ?
C10 C9 C14 C13 -0.3(3) . . . . ?
O2 C9 C14 C13 178.92(15) . . . . ?
C10 C9 C14 N2 -179.82(16) . . . . ?
O2 C9 C14 N2 -0.60(18) . . . . ?
C12 C13 C14 C9 0.2(2) . . . . ?
C16 C13 C14 C9 179.61(18) . . . . ?
C12 C13 C14 N2 179.54(17) . . . . ?
C16 C13 C14 N2 -1.0(3) . . . . ?
O2 C8 N2 C14 -1.08(18) . . . . ?
C1' C8 N2 C14 179.51(18) . . . . ?
O2 C8 N2 Al1 178.65(10) . . . . ?
C1' C8 N2 Al1 -0.8(2) . . . . ?
C9 C14 N2 C8 1.00(18) . . . . ?
C13 C14 N2 C8 -178.44(18) . . . . ?
C9 C14 N2 Al1 -178.68(12) . . . . ?
C13 C14 N2 Al1 1.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1' H1' O1 0.95 2.40 3.326(2) 166.0 3_676
C10 H10 I1 0.95 3.24 4.001(2) 138.3 3_566

_refine_diff_density_max         0.730
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Oxygen-sensitive'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3lambda
_database_code_depnum_ccdc_archive 'CCDC 1429356'
_audit_update_record             
;
2015-10-04 deposited with the CCDC.
2015-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        '4-Methylbenzoxazol-2-yl-carboxamide '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 N2 O2'
_chemical_formula_sum            'C10 H10 N2 O2'
_chemical_formula_weight         190.20

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      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                   7.790(2)
_cell_length_b                   7.974(2)
_cell_length_c                   8.279(3)
_cell_angle_alpha                93.24(2)
_cell_angle_beta                 115.09(3)
_cell_angle_gamma                99.95(2)
_cell_volume                     453.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2385
_cell_measurement_theta_min      2.746
_cell_measurement_theta_max      25.094

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6823
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS-2014/4

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'INCOATEC Microsource'
_diffrn_measurement_device_type  'Bruker Smart APEX II Quazar'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7223
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.621
_diffrn_reflns_theta_max         25.503
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1691
_reflns_number_gt                1389
_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       'APEX2 v2012.2'
_computing_cell_refinement       'SAINT V8.34A'
_computing_data_reduction        'SAINT V8.34A'
_computing_structure_solution    'SHELXT (Sheldrick,Acta Cryst.(2015)A71,3-8)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'

_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)+(0.0606P)²+0.2790P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1691
_refine_ls_number_parameters     137
_refine_ls_number_restraints     198
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1345
_refine_ls_wR_factor_gt          0.1251
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.033
_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 0.4946(3) 0.5005(3) 0.2676(3) 0.0271(5) Uani 1 1 d . U . . .
H1'A H 0.4412 0.5454 0.3463 0.033 Uiso 1 1 calc R U . . .
H1'B H 0.4703 0.5698 0.1678 0.033 Uiso 1 1 calc R U . . .
H1N H 0.772(4) 0.648(3) 0.211(4) 0.045(7) Uiso 1 1 d . . . . .
C1 C 0.3969(3) 0.3156(3) 0.1932(3) 0.0243(5) Uani 1 1 d . U . . .
O1 O 0.3711(2) 0.21335(19) 0.31268(19) 0.0286(4) Uani 1 1 d . U . . .
C2 C 0.2904(3) 0.0505(3) 0.2113(3) 0.0251(5) Uani 1 1 d . U . . .
H2N H 0.956(4) 0.595(3) 0.369(4) 0.047(8) Uiso 1 1 d . . . . .
C3 C 0.2367(3) -0.1037(3) 0.2642(3) 0.0284(5) Uani 1 1 d . U . . .
H3 H 0.2522 -0.1123 0.3834 0.034 Uiso 1 1 calc R U . . .
C4 C 0.1588(3) -0.2444(3) 0.1297(3) 0.0293(5) Uani 1 1 d . U . . .
H4 H 0.1177 -0.3540 0.1566 0.035 Uiso 1 1 calc R U . . .
C5 C 0.1388(3) -0.2297(3) -0.0447(3) 0.0296(5) Uani 1 1 d . U . . .
H5 H 0.0833 -0.3300 -0.1325 0.036 Uiso 1 1 calc R U . . .
C6 C 0.1967(3) -0.0750(3) -0.0946(3) 0.0294(5) Uani 1 1 d . U . . .
C7 C 0.2720(3) 0.0671(3) 0.0392(3) 0.0248(5) Uani 1 1 d . U . . .
C9 C 0.1820(4) -0.0612(3) -0.2803(3) 0.0388(6) Uani 1 1 d . U . . .
H9A H 0.1526 -0.1768 -0.3457 0.058 Uiso 1 1 calc R U . . .
H9B H 0.3056 0.0039 -0.2706 0.058 Uiso 1 1 calc R U . . .
H9C H 0.0782 -0.0019 -0.3456 0.058 Uiso 1 1 calc R U . . .
N1 N 0.3433(2) 0.2408(2) 0.0335(2) 0.0265(4) Uani 1 1 d . U . . .
C8 C 0.7135(3) 0.5147(3) 0.3762(3) 0.0252(5) Uani 1 1 d . U . . .
O2 O 0.7758(2) 0.4457(2) 0.5139(2) 0.0302(4) Uani 1 1 d . U . . .
N2 N 0.8254(3) 0.5994(2) 0.3117(3) 0.0300(5) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1' C1 1.498(3) . ?
C1' C8 1.533(3) . ?
C1 N1 1.279(3) . ?
C1 O1 1.373(2) . ?
O1 C2 1.390(3) . ?
C2 C3 1.385(3) . ?
C2 C7 1.386(3) . ?
C3 C4 1.385(3) . ?
C4 C5 1.399(3) . ?
C5 C6 1.386(3) . ?
C6 C7 1.390(3) . ?
C6 C9 1.504(3) . ?
C7 N1 1.411(3) . ?
C8 O2 1.237(3) . ?
C8 N2 1.316(3) . ?
N2 H1N 0.90(3) . ?
N2 H2N 0.93(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C1' C8 109.21(17) . . ?
N1 C1 O1 116.43(19) . . ?
N1 C1 C1' 127.30(19) . . ?
O1 C1 C1' 116.18(18) . . ?
C1 O1 C2 103.54(16) . . ?
C3 C2 C7 124.1(2) . . ?
C3 C2 O1 128.78(19) . . ?
C7 C2 O1 107.13(18) . . ?
C4 C3 C2 114.7(2) . . ?
C3 C4 C5 121.9(2) . . ?
C6 C5 C4 122.7(2) . . ?
C5 C6 C7 115.6(2) . . ?
C5 C6 C9 122.4(2) . . ?
C7 C6 C9 122.0(2) . . ?
C2 C7 C6 121.0(2) . . ?
C2 C7 N1 108.98(19) . . ?
C6 C7 N1 129.99(19) . . ?
C1 N1 C7 103.92(17) . . ?
O2 C8 N2 123.7(2) . . ?
O2 C8 C1' 120.16(19) . . ?
N2 C8 C1' 116.16(18) . . ?
H1N N2 H2N 124(2) . . ?
H1N N2 C8 119.9(17) . . ?
H2N N2 C8 115.5(16) . . ?

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 C1' C1 N1 -99.3(2) . . . . ?
C8 C1' C1 O1 77.0(2) . . . . ?
N1 C1 O1 C2 0.4(2) . . . . ?
C1' C1 O1 C2 -176.37(16) . . . . ?
C1 O1 C2 C3 179.1(2) . . . . ?
C1 O1 C2 C7 -0.6(2) . . . . ?
C7 C2 C3 C4 -0.8(3) . . . . ?
O1 C2 C3 C4 179.65(18) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C7 -1.6(3) . . . . ?
C4 C5 C6 C9 177.6(2) . . . . ?
C3 C2 C7 C6 -0.3(3) . . . . ?
O1 C2 C7 C6 179.38(18) . . . . ?
C3 C2 C7 N1 -179.08(18) . . . . ?
O1 C2 C7 N1 0.6(2) . . . . ?
C5 C6 C7 C2 1.4(3) . . . . ?
C9 C6 C7 C2 -177.8(2) . . . . ?
C5 C6 C7 N1 179.97(19) . . . . ?
C9 C6 C7 N1 0.8(3) . . . . ?
O1 C1 N1 C7 0.0(2) . . . . ?
C1' C1 N1 C7 176.30(19) . . . . ?
C2 C7 N1 C1 -0.3(2) . . . . ?
C6 C7 N1 C1 -179.0(2) . . . . ?
C1 C1' C8 O2 -63.8(3) . . . . ?
C1 C1' C8 N2 114.7(2) . . . . ?
O2 C8 N2 H1N -179.3(19) . . . . ?
C1' C8 N2 H1N 2(2) . . . . ?
O2 C8 N2 H2N 6.6(19) . . . . ?
C1' C8 N2 H2N -171.9(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N O2 0.93(3) 1.99(3) 2.917(3) 173(2) 2_766
N2 H1N N1 0.90(3) 2.15(3) 3.053(3) 177(2) 2_665
C1' H1'A O2 0.99 2.43 3.368(3) 158.5 2_666
N2 H1N N1 0.90(3) 2.15(3) 3.053(3) 177(2) 2_665
N2 H2N O2 0.93(3) 1.99(3) 2.917(3) 173(2) 2_766

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4


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

data_2_mbox2CHAlMe2
_database_code_depnum_ccdc_archive 'CCDC 1429357'
_audit_update_record             
;
2015-10-03 deposited with the CCDC.
2015-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'Dimethyl aluminium bis-(4-methylbenzoxazol-2-yl)-methanide'
_chemical_name_common            '[Me2Al{(4-Me-NCOC6H3)2CH}]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 Al N2 O2'
_chemical_formula_sum            'C19 H19 Al N2 O2'
_chemical_formula_weight         334.34

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      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                   8.029(2)
_cell_length_b                   14.773(3)
_cell_length_c                   14.072(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.03(2)
_cell_angle_gamma                90
_cell_volume                     1669.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9761
_cell_measurement_theta_min      2.537
_cell_measurement_theta_max      25.3515

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    0.135
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7119
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS-2014/4

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'INCOATEC Microsource'
_diffrn_measurement_device_type  'Bruker Smart APEX II Quazar'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            57930
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.378
_diffrn_reflns_theta_max         25.351
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3060
_reflns_number_gt                2925
_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       'APEX2 v2012.2'
_computing_cell_refinement       'SAINT V8.34A'
_computing_data_reduction        'SAINT V8.34A'
_computing_structure_solution    'SHELXS-2012 (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'

_refine_special_details          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)+(0.0526P)²+0.4560P] 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       0.0025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3060
_refine_ls_number_parameters     223
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.066
_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
Al1 Al 0.23868(5) 0.24746(3) 0.62014(4) 0.01769(13) Uani 1 1 d D . . . .
C1' C 0.65027(19) 0.27339(10) 0.61932(14) 0.0234(3) Uani 1 1 d D . . . .
H1' H 0.7678 0.2808 0.6184 0.028 Uiso 1 1 calc R U . . .
C1 C 0.54896(19) 0.34909(11) 0.61887(12) 0.0209(3) Uani 1 1 d D . . . .
C2 C 0.4922(2) 0.49408(11) 0.62041(12) 0.0217(3) Uani 1 1 d D . . . .
C3 C 0.5069(2) 0.58709(11) 0.62311(13) 0.0253(4) Uani 1 1 d D . . . .
H3 H 0.6118 0.6169 0.6230 0.030 Uiso 1 1 calc R U . . .
C4 C 0.3563(2) 0.63413(11) 0.62597(14) 0.0277(4) Uani 1 1 d D . . . .
H4 H 0.3573 0.6984 0.6279 0.033 Uiso 1 1 calc R U . . .
C5 C 0.2046(2) 0.58854(11) 0.62603(13) 0.0260(4) Uani 1 1 d D . . . .
H5 H 0.1051 0.6233 0.6279 0.031 Uiso 1 1 calc R U . . .
C6 C 0.1914(2) 0.49421(10) 0.62349(13) 0.0217(3) Uani 1 1 d D . . . .
C7 C 0.3421(2) 0.44723(10) 0.62080(12) 0.0193(3) Uani 1 1 d D . . . .
C15 C 0.0226(2) 0.44924(12) 0.62281(15) 0.0292(4) Uani 1 1 d D . . . .
H15A H -0.0646 0.4956 0.6247 0.044 Uiso 1 1 calc R U . . .
H15B H 0.0123 0.4098 0.6785 0.044 Uiso 1 1 calc R U . . .
H15C H 0.0106 0.4131 0.5648 0.044 Uiso 1 1 calc R U . . .
O1 O 0.62122(14) 0.43218(7) 0.61894(9) 0.0232(3) Uani 1 1 d D . . . .
N1 N 0.38098(16) 0.35363(9) 0.61912(10) 0.0198(3) Uani 1 1 d D . . . .
C8 C 0.5834(2) 0.18709(11) 0.62112(13) 0.0203(3) Uani 1 1 d D . . . .
C9 C 0.5892(2) 0.03916(11) 0.62688(13) 0.0218(3) Uani 1 1 d D . . . .
C10 C 0.6424(2) -0.04922(11) 0.63273(13) 0.0277(4) Uani 1 1 d D . . . .
H10 H 0.7570 -0.0649 0.6353 0.033 Uiso 1 1 calc R U . . .
C11 C 0.5168(2) -0.11384(12) 0.63456(14) 0.0302(4) Uani 1 1 d D . . . .
H11 H 0.5455 -0.1761 0.6380 0.036 Uiso 1 1 calc R U . . .
C12 C 0.3491(2) -0.08900(12) 0.63146(14) 0.0288(4) Uani 1 1 d D . . . .
H12 H 0.2670 -0.1353 0.6329 0.035 Uiso 1 1 calc R U . . .
C13 C 0.2966(2) 0.00129(11) 0.62633(13) 0.0239(3) Uani 1 1 d D . . . .
C14 C 0.4236(2) 0.06599(10) 0.62482(13) 0.0199(3) Uani 1 1 d D . . . .
C16 C 0.1135(2) 0.02434(12) 0.62273(17) 0.0322(4) Uani 1 1 d D . . . .
H16A H 0.0923 0.0653 0.5693 0.048 Uiso 1 1 calc R U . . .
H16B H 0.0807 0.0539 0.6822 0.048 Uiso 1 1 calc R U . . .
H16C H 0.0485 -0.0313 0.6143 0.048 Uiso 1 1 calc R U . . .
O2 O 0.68938(15) 0.11512(7) 0.62394(9) 0.0232(3) Uani 1 1 d D . . . .
N2 N 0.42167(16) 0.16175(9) 0.62106(11) 0.0194(3) Uani 1 1 d D . . . .
C1M C 0.1175(3) 0.23856(12) 0.74065(12) 0.0260(4) Uani 1 1 d . . . . .
H1MA H -0.0009 0.2279 0.7278 0.039 Uiso 1 1 calc R U . . .
H1MB H 0.1304 0.2951 0.7763 0.039 Uiso 1 1 calc R U . . .
H1MC H 0.1623 0.1882 0.7781 0.039 Uiso 1 1 calc R U . . .
C2M C 0.1142(3) 0.24051(12) 0.49973(13) 0.0249(4) Uani 1 1 d . . . . .
H2MA H 0.1224 0.2985 0.4663 0.037 Uiso 1 1 calc R U . . .
H2MB H -0.0031 0.2271 0.5130 0.037 Uiso 1 1 calc R U . . .
H2MC H 0.1612 0.1924 0.4600 0.037 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
Al1 N2 1.9395(14) . ?
Al1 N1 1.9405(14) . ?
Al1 C1M 1.9601(19) . ?
Al1 C2M 1.970(2) . ?
C1' H1' 0.9500 . ?
C1' C1 1.383(2) . ?
C1' C8 1.384(2) . ?
C1 N1 1.350(2) . ?
C1 O1 1.3578(19) . ?
C2 C3 1.380(2) . ?
C2 O1 1.3821(19) . ?
C2 C7 1.390(2) . ?
C3 C4 1.395(2) . ?
C4 C5 1.392(2) . ?
C5 C6 1.398(2) . ?
C6 C7 1.395(2) . ?
C6 C15 1.509(2) . ?
C7 N1 1.418(2) . ?
C8 N2 1.351(2) . ?
C8 O2 1.3624(19) . ?
C9 C10 1.376(2) . ?
C9 O2 1.381(2) . ?
C9 C14 1.387(2) . ?
C10 C11 1.389(2) . ?
C11 C12 1.396(3) . ?
C12 C13 1.401(2) . ?
C13 C14 1.398(2) . ?
C13 C16 1.510(2) . ?
C14 N2 1.416(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Al1 N1 94.68(6) . . ?
N2 Al1 C1M 109.08(8) . . ?
N1 Al1 C1M 110.68(7) . . ?
N2 Al1 C2M 110.85(8) . . ?
N1 Al1 C2M 109.53(8) . . ?
C1M Al1 C2M 119.26(7) . . ?
H1' C1' C1 119.4 . . ?
H1' C1' C8 119.4 . . ?
C1 C1' C8 121.13(14) . . ?
N1 C1 O1 112.45(14) . . ?
N1 C1 C1' 128.88(15) . . ?
O1 C1 C1' 118.67(14) . . ?
C3 C2 O1 126.51(14) . . ?
C3 C2 C7 124.77(15) . . ?
O1 C2 C7 108.71(13) . . ?
C2 C3 C4 114.99(15) . . ?
C5 C4 C3 121.15(15) . . ?
C4 C5 C6 123.28(16) . . ?
C7 C6 C5 115.52(15) . . ?
C7 C6 C15 124.02(14) . . ?
C5 C6 C15 120.46(15) . . ?
C2 C7 C6 120.28(14) . . ?
C2 C7 N1 107.13(14) . . ?
C6 C7 N1 132.58(14) . . ?
C1 O1 C2 106.13(12) . . ?
C1 N1 C7 105.57(13) . . ?
C1 N1 Al1 123.23(12) . . ?
C7 N1 Al1 131.18(11) . . ?
N2 C8 O2 112.59(13) . . ?
N2 C8 C1' 128.91(14) . . ?
O2 C8 C1' 118.50(13) . . ?
C10 C9 O2 126.27(15) . . ?
C10 C9 C14 124.73(15) . . ?
O2 C9 C14 108.98(13) . . ?
C9 C10 C11 115.33(16) . . ?
C10 C11 C12 121.26(16) . . ?
C11 C12 C13 122.81(16) . . ?
C14 C13 C12 115.63(16) . . ?
C14 C13 C16 123.76(15) . . ?
C12 C13 C16 120.61(15) . . ?
C9 C14 C13 120.22(14) . . ?
C9 C14 N2 107.27(13) . . ?
C13 C14 N2 132.51(14) . . ?
C8 O2 C9 105.72(12) . . ?
C8 N2 C14 105.43(12) . . ?
C8 N2 Al1 123.17(10) . . ?
C14 N2 Al1 131.37(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
H1' C1' C1 N1 179.3 . . . . ?
C8 C1' C1 N1 -0.7(3) . . . . ?
H1' C1' C1 O1 -1.3 . . . . ?
C8 C1' C1 O1 178.74(15) . . . . ?
O1 C2 C3 C4 -178.82(17) . . . . ?
C7 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C4 C5 C6 C15 -179.44(19) . . . . ?
C3 C2 C7 C6 0.4(3) . . . . ?
O1 C2 C7 C6 179.16(16) . . . . ?
C3 C2 C7 N1 -179.00(17) . . . . ?
O1 C2 C7 N1 -0.24(19) . . . . ?
C5 C6 C7 C2 -0.2(3) . . . . ?
C15 C6 C7 C2 179.16(17) . . . . ?
C5 C6 C7 N1 178.99(17) . . . . ?
C15 C6 C7 N1 -1.6(3) . . . . ?
N1 C1 O1 C2 0.71(19) . . . . ?
C1' C1 O1 C2 -178.80(16) . . . . ?
C3 C2 O1 C1 178.47(18) . . . . ?
C7 C2 O1 C1 -0.27(18) . . . . ?
O1 C1 N1 C7 -0.9(2) . . . . ?
C1' C1 N1 C7 178.60(18) . . . . ?
O1 C1 N1 Al1 -179.49(10) . . . . ?
C1' C1 N1 Al1 0.0(3) . . . . ?
C2 C7 N1 C1 0.6(2) . . . . ?
C6 C7 N1 C1 -178.65(19) . . . . ?
C2 C7 N1 Al1 179.13(12) . . . . ?
C6 C7 N1 Al1 -0.2(3) . . . . ?
H1' C1' C8 N2 -178.8 . . . . ?
C1 C1' C8 N2 1.2(3) . . . . ?
H1' C1' C8 O2 1.7 . . . . ?
C1 C1' C8 O2 -178.34(16) . . . . ?
O2 C9 C10 C11 -179.94(17) . . . . ?
C14 C9 C10 C11 1.4(3) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C11 C12 C13 C16 179.74(19) . . . . ?
C10 C9 C14 C13 -1.6(3) . . . . ?
O2 C9 C14 C13 179.48(15) . . . . ?
C10 C9 C14 N2 178.53(16) . . . . ?
O2 C9 C14 N2 -0.4(2) . . . . ?
C12 C13 C14 C9 1.0(3) . . . . ?
C16 C13 C14 C9 -179.0(2) . . . . ?
C12 C13 C14 N2 -179.25(18) . . . . ?
C16 C13 C14 N2 0.8(3) . . . . ?
N2 C8 O2 C9 -0.7(2) . . . . ?
C1' C8 O2 C9 178.98(16) . . . . ?
C10 C9 O2 C8 -178.26(17) . . . . ?
C14 C9 O2 C8 0.6(2) . . . . ?
O2 C8 N2 C14 0.4(2) . . . . ?
C1' C8 N2 C14 -179.15(18) . . . . ?
O2 C8 N2 Al1 178.64(10) . . . . ?
C1' C8 N2 Al1 -1.0(3) . . . . ?
C9 C14 N2 C8 0.0(2) . . . . ?
C13 C14 N2 C8 -179.9(2) . . . . ?
C9 C14 N2 Al1 -178.03(13) . . . . ?
C13 C14 N2 Al1 2.2(3) . . . . ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Oxygen-sensitive'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3_mbox2CHGaMe2
_database_code_depnum_ccdc_archive 'CCDC 1429403'
_audit_update_record             
;
2015-10-04 deposited with the CCDC.
2015-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'dimethyl gallium bis-(4-methylbenzoxazol-2-yl)-methanide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 Ga N2 O2'
_chemical_formula_sum            'C19 H19 Ga N2 O2'
_chemical_formula_weight         377.08

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'
O O 0.0056 0.0036 '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      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                   7.9857(2)
_cell_length_b                   14.8521(5)
_cell_length_c                   14.0873(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.1780(10)
_cell_angle_gamma                90
_cell_volume                     1670.81(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9941
_cell_measurement_theta_min      2.285
_cell_measurement_theta_max      19.745

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.065
_exptl_absorpt_coefficient_mu    0.879
_shelx_estimated_absorpt_T_min   0.885
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7051
_exptl_absorpt_correction_T_max  0.7444
_exptl_absorpt_process_details   SADABS-2014/4

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.56086
_diffrn_radiation_type           AgK\a
_diffrn_source                   'INCOATEC Microsource'
_diffrn_measurement_device_type  'Bruker Smart APEX II Quazar'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45271
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.572
_diffrn_reflns_theta_max         19.770
_diffrn_reflns_theta_full        19.665
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3069
_reflns_number_gt                2708
_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       'APEX2 v2012.2'
_computing_cell_refinement       'SAINT V8.34A'
_computing_data_reduction        'SAINT V8.34A'
_computing_structure_solution    'SHELXS-2012 (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'

_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)+(0.0353P)²+1.1047P] 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         3069
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.0672
_refine_ls_wR_factor_gt          0.0641
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1' C 0.6475(2) 0.27171(13) 0.61893(15) 0.0207(4) Uani 1 1 d . . . . .
H1' H 0.7656 0.2789 0.6178 0.025 Uiso 1 1 calc R U . . .
C1 C 0.5804(2) 0.18556(13) 0.62090(13) 0.0175(4) Uani 1 1 d . . . . .
O1 O 0.68794(16) 0.11457(9) 0.62374(10) 0.0199(3) Uani 1 1 d . . . . .
C2 C 0.5886(2) 0.03838(13) 0.62704(13) 0.0190(4) Uani 1 1 d . . . . .
C3 C 0.6419(3) -0.04923(13) 0.63269(14) 0.0237(4) Uani 1 1 d . . . . .
H3 H 0.7573 -0.0647 0.6348 0.028 Uiso 1 1 calc R U . . .
C4 C 0.5160(3) -0.11393(14) 0.63517(15) 0.0271(5) Uani 1 1 d . . . . .
H4 H 0.5452 -0.1758 0.6392 0.032 Uiso 1 1 calc R U . . .
C5 C 0.3482(3) -0.08951(13) 0.63189(15) 0.0248(5) Uani 1 1 d . . . . .
H5 H 0.2660 -0.1357 0.6330 0.030 Uiso 1 1 calc R U . . .
C6 C 0.2948(2) 0.00029(14) 0.62695(14) 0.0209(4) Uani 1 1 d . . . . .
C7 C 0.4220(2) 0.06466(12) 0.62499(13) 0.0171(4) Uani 1 1 d . . . . .
N1 N 0.41957(19) 0.15979(10) 0.62098(11) 0.0160(3) Uani 1 1 d . . . . .
C15 C 0.1112(3) 0.02296(14) 0.62354(17) 0.0292(5) Uani 1 1 d . . . . .
H15A H 0.0886 0.0615 0.5685 0.044 Uiso 1 1 calc R U . . .
H15B H 0.0797 0.0547 0.6818 0.044 Uiso 1 1 calc R U . . .
H15C H 0.0458 -0.0326 0.6181 0.044 Uiso 1 1 calc R U . . .
Ga1 Ga 0.22685(2) 0.24637(2) 0.62002(2) 0.01434(9) Uani 1 1 d . . . . .
C1M C 0.1109(3) 0.23926(13) 0.49696(14) 0.0229(4) Uani 1 1 d . . . . .
H1MA H 0.1238 0.2964 0.4630 0.034 Uiso 1 1 calc R U . . .
H1MB H -0.0084 0.2273 0.5074 0.034 Uiso 1 1 calc R U . . .
H1MC H 0.1593 0.1904 0.4591 0.034 Uiso 1 1 calc R U . . .
C2M C 0.1133(3) 0.23903(13) 0.74313(14) 0.0233(4) Uani 1 1 d . . . . .
H2MA H -0.0067 0.2289 0.7329 0.035 Uiso 1 1 calc R U . . .
H2MB H 0.1296 0.2955 0.7779 0.035 Uiso 1 1 calc R U . . .
H2MC H 0.1602 0.1890 0.7800 0.035 Uiso 1 1 calc R U . . .
C8 C 0.5460(2) 0.34769(13) 0.61856(14) 0.0177(4) Uani 1 1 d . . . . .
O2 O 0.62201(16) 0.42972(9) 0.61873(10) 0.0204(3) Uani 1 1 d . . . . .
C9 C 0.4932(2) 0.49278(13) 0.62062(13) 0.0183(4) Uani 1 1 d . . . . .
C10 C 0.5106(3) 0.58460(13) 0.62312(14) 0.0236(4) Uani 1 1 d . . . . .
H10 H 0.6168 0.6134 0.6230 0.028 Uiso 1 1 calc R U . . .
C11 C 0.3611(3) 0.63243(13) 0.62587(15) 0.0252(5) Uani 1 1 d . . . . .
H11 H 0.3639 0.6964 0.6278 0.030 Uiso 1 1 calc R U . . .
C12 C 0.2074(3) 0.58819(14) 0.62587(14) 0.0227(4) Uani 1 1 d . . . . .
H12 H 0.1084 0.6236 0.6281 0.027 Uiso 1 1 calc R U . . .
C13 C 0.1909(2) 0.49434(13) 0.62283(13) 0.0187(4) Uani 1 1 d . . . . .
C14 C 0.3420(2) 0.44697(12) 0.62067(13) 0.0165(4) Uani 1 1 d . . . . .
N2 N 0.37835(19) 0.35385(10) 0.61884(11) 0.0161(3) Uani 1 1 d . . . . .
C16 C 0.0216(2) 0.45075(14) 0.62253(16) 0.0254(5) Uani 1 1 d . . . . .
H16A H -0.0653 0.4974 0.6227 0.038 Uiso 1 1 calc R U . . .
H16B H 0.0099 0.4129 0.6791 0.038 Uiso 1 1 calc R U . . .
H16C H 0.0094 0.4135 0.5655 0.038 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' H1' 0.9500 . ?
C1' C1 1.387(3) . ?
C1' C8 1.389(3) . ?
C1 N1 1.340(2) . ?
C1 O1 1.360(2) . ?
O1 C2 1.383(2) . ?
C2 C3 1.371(3) . ?
C2 C7 1.387(3) . ?
C3 C4 1.392(3) . ?
C4 C5 1.389(3) . ?
C5 C6 1.402(3) . ?
C6 C7 1.395(3) . ?
C6 C15 1.505(3) . ?
C7 N1 1.414(2) . ?
N1 Ga1 2.0055(15) . ?
Ga1 C2M 1.963(2) . ?
Ga1 C1M 1.966(2) . ?
Ga1 N2 2.0030(15) . ?
C8 N2 1.342(2) . ?
C8 O2 1.361(2) . ?
O2 C9 1.391(2) . ?
C9 C10 1.371(3) . ?
C9 C14 1.386(3) . ?
C10 C11 1.390(3) . ?
C11 C12 1.392(3) . ?
C12 C13 1.401(3) . ?
C13 C14 1.397(3) . ?
C13 C16 1.499(3) . ?
C14 N2 1.413(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1' C1' C1 119.2 . . ?
H1' C1' C8 119.2 . . ?
C1 C1' C8 121.62(18) . . ?
N1 C1 O1 112.55(16) . . ?
N1 C1 C1' 129.28(17) . . ?
O1 C1 C1' 118.17(17) . . ?
C1 O1 C2 105.86(14) . . ?
C3 C2 O1 126.90(18) . . ?
C3 C2 C7 124.46(18) . . ?
O1 C2 C7 108.63(16) . . ?
C2 C3 C4 115.62(19) . . ?
C5 C4 C3 121.08(19) . . ?
C4 C5 C6 122.93(19) . . ?
C7 C6 C5 115.54(18) . . ?
C7 C6 C15 123.74(18) . . ?
C5 C6 C15 120.72(18) . . ?
C2 C7 C6 120.36(18) . . ?
C2 C7 N1 107.16(16) . . ?
C6 C7 N1 132.48(18) . . ?
C1 N1 C7 105.80(15) . . ?
C1 N1 Ga1 123.53(12) . . ?
C7 N1 Ga1 130.64(13) . . ?
C2M Ga1 C1M 123.95(9) . . ?
C2M Ga1 N2 109.42(8) . . ?
C1M Ga1 N2 108.57(8) . . ?
C2M Ga1 N1 108.37(8) . . ?
C1M Ga1 N1 109.32(7) . . ?
N2 Ga1 N1 92.73(6) . . ?
N2 C8 O2 112.58(16) . . ?
N2 C8 C1' 129.58(18) . . ?
O2 C8 C1' 117.83(16) . . ?
C8 O2 C9 105.83(14) . . ?
C10 C9 C14 125.19(18) . . ?
C10 C9 O2 126.52(17) . . ?
C14 C9 O2 108.28(16) . . ?
C9 C10 C11 114.98(19) . . ?
C10 C11 C12 121.07(18) . . ?
C11 C12 C13 123.54(19) . . ?
C14 C13 C12 114.87(18) . . ?
C14 C13 C16 124.16(18) . . ?
C12 C13 C16 120.97(18) . . ?
C9 C14 C13 120.35(18) . . ?
C9 C14 N2 107.53(16) . . ?
C13 C14 N2 132.12(18) . . ?
C8 N2 C14 105.77(15) . . ?
C8 N2 Ga1 123.25(13) . . ?
C14 N2 Ga1 130.96(13) . . ?

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
H1' C1' C1 N1 -178.7 . . . . ?
C8 C1' C1 N1 1.3(3) . . . . ?
H1' C1' C1 O1 1.8 . . . . ?
C8 C1' C1 O1 -178.24(18) . . . . ?
N1 C1 O1 C2 -0.8(2) . . . . ?
C1' C1 O1 C2 178.87(18) . . . . ?
C1 O1 C2 C3 -178.5(2) . . . . ?
C1 O1 C2 C7 0.7(2) . . . . ?
O1 C2 C3 C4 179.91(19) . . . . ?
C7 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C4 C5 C6 C15 180.0(2) . . . . ?
C3 C2 C7 C6 -1.2(3) . . . . ?
O1 C2 C7 C6 179.58(17) . . . . ?
C3 C2 C7 N1 178.81(18) . . . . ?
O1 C2 C7 N1 -0.4(2) . . . . ?
C5 C6 C7 C2 0.6(3) . . . . ?
C15 C6 C7 C2 -179.1(2) . . . . ?
C5 C6 C7 N1 -179.46(19) . . . . ?
C15 C6 C7 N1 0.9(3) . . . . ?
O1 C1 N1 C7 0.5(2) . . . . ?
C1' C1 N1 C7 -179.1(2) . . . . ?
O1 C1 N1 Ga1 178.64(11) . . . . ?
C1' C1 N1 Ga1 -1.0(3) . . . . ?
C2 C7 N1 C1 -0.1(2) . . . . ?
C6 C7 N1 C1 180.0(2) . . . . ?
C2 C7 N1 Ga1 -178.00(13) . . . . ?
C6 C7 N1 Ga1 2.0(3) . . . . ?
H1' C1' C8 N2 179.2 . . . . ?
C1 C1' C8 N2 -0.8(3) . . . . ?
H1' C1' C8 O2 -1.4 . . . . ?
C1 C1' C8 O2 178.55(18) . . . . ?
N2 C8 O2 C9 0.9(2) . . . . ?
C1' C8 O2 C9 -178.60(17) . . . . ?
C8 O2 C9 C10 178.8(2) . . . . ?
C8 O2 C9 C14 -0.5(2) . . . . ?
C14 C9 C10 C11 0.0(3) . . . . ?
O2 C9 C10 C11 -179.20(18) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C11 C12 C13 C16 -179.7(2) . . . . ?
C10 C9 C14 C13 0.4(3) . . . . ?
O2 C9 C14 C13 179.71(17) . . . . ?
C10 C9 C14 N2 -179.28(19) . . . . ?
O2 C9 C14 N2 0.0(2) . . . . ?
C12 C13 C14 C9 -0.7(3) . . . . ?
C16 C13 C14 C9 179.65(19) . . . . ?
C12 C13 C14 N2 178.93(19) . . . . ?
C16 C13 C14 N2 -0.8(3) . . . . ?
O2 C8 N2 C14 -0.9(2) . . . . ?
C1' C8 N2 C14 178.5(2) . . . . ?
O2 C8 N2 Ga1 -179.36(12) . . . . ?
C1' C8 N2 Ga1 0.0(3) . . . . ?
C9 C14 N2 C8 0.5(2) . . . . ?
C13 C14 N2 C8 -179.1(2) . . . . ?
C9 C14 N2 Ga1 178.82(13) . . . . ?
C13 C14 N2 Ga1 -0.8(3) . . . . ?

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Oxygen-sensitive'
_exptl_crystal_preparation       Luminescent
