# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1480574'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H31 Al Cl2 N2'
_chemical_formula_sum            'C33 H31 Al Cl2 N2'
_chemical_formula_weight         553.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           34
_space_group_name_H-M_alt        'P n n 2'
_space_group_name_Hall           'P 2 -2n'

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

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

_cell_length_a                   10.0003(6)
_cell_length_b                   11.7787(7)
_cell_length_c                   12.3391(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1453.43(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6473
_cell_measurement_theta_min      2.390
_cell_measurement_theta_max      32.079

_exptl_crystal_description       chunk
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             580
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.278
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.718668
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'twinabs (Sheldrick, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Platform with 4k CCD'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9029
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.390
_diffrn_reflns_theta_max         33.300
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9029
_reflns_number_gt                8189
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_max     0.940
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin with an HKLF 5 file
 containing single reflections from the major component
 and composite reflections
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0559P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2136 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         9029
_refine_ls_number_parameters     178
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0890
_refine_ls_wR_factor_gt          0.0877
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.014
_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
Cl1 Cl 0.85179(5) 0.92481(4) 0.13556(4) 0.03085(11) Uani 1 1 d . . . . .
Al1 Al 1.0000 1.0000 0.03550(6) 0.02053(15) Uani 1 2 d S T P . .
N1 N 1.07616(16) 0.90099(13) -0.06688(12) 0.0213(3) Uani 1 1 d . . . . .
C1 C 1.0000 1.0000 -0.2331(2) 0.0201(4) Uani 1 2 d S T P . .
C2 C 1.07425(19) 0.91557(14) -0.17992(14) 0.0214(3) Uani 1 1 d . . . . .
C3 C 1.1523(2) 0.82816(17) -0.22678(17) 0.0300(4) Uani 1 1 d . . . . .
H3 H 1.1676 0.8167 -0.3020 0.036 Uiso 1 1 calc R U . . .
C4 C 1.2019(2) 0.76275(18) -0.14356(18) 0.0348(5) Uani 1 1 d . . . . .
H4 H 1.2597 0.6992 -0.1508 0.042 Uiso 1 1 calc R U . . .
C5 C 1.15183(19) 0.80687(16) -0.04639(16) 0.0257(4) Uani 1 1 d . . . . .
C6 C 1.16032(19) 0.76033(15) 0.06505(15) 0.0241(3) Uani 1 1 d . . . . .
C7 C 1.26802(17) 0.78629(16) 0.13366(19) 0.0274(3) Uani 1 1 d . . . . .
C8 C 1.2662(2) 0.7451(2) 0.23898(17) 0.0305(4) Uani 1 1 d . . . . .
H8 H 1.3384 0.7629 0.2860 0.037 Uiso 1 1 calc R U . . .
C9 C 1.1622(2) 0.67855(19) 0.27756(17) 0.0311(4) Uani 1 1 d . . . . .
C10 C 1.0590(2) 0.65068(18) 0.20693(18) 0.0306(4) Uani 1 1 d . . . . .
H10 H 0.9882 0.6037 0.2320 0.037 Uiso 1 1 calc R U . . .
C11 C 1.05668(19) 0.68967(16) 0.10077(16) 0.0267(4) Uani 1 1 d . . . . .
C12 C 1.3864(2) 0.8531(2) 0.0935(3) 0.0469(6) Uani 1 1 d . . . . .
H12A H 1.4259 0.8954 0.1539 0.070 Uiso 1 1 calc R U . . .
H12B H 1.3572 0.9063 0.0373 0.070 Uiso 1 1 calc R U . . .
H12C H 1.4531 0.8010 0.0633 0.070 Uiso 1 1 calc R U . . .
C13 C 1.1625(3) 0.6356(3) 0.3922(2) 0.0520(7) Uani 1 1 d . . . . .
H13A H 1.0908 0.5797 0.4013 0.078 Uiso 1 1 calc R U . . .
H13B H 1.1480 0.6992 0.4420 0.078 Uiso 1 1 calc R U . . .
H13C H 1.2489 0.5999 0.4080 0.078 Uiso 1 1 calc R U . . .
C14 C 0.9442(2) 0.65453(19) 0.0264(2) 0.0397(5) Uani 1 1 d . . . . .
H14A H 0.8993 0.5875 0.0563 0.060 Uiso 1 1 calc R U . . .
H14B H 0.9804 0.6364 -0.0453 0.060 Uiso 1 1 calc R U . . .
H14C H 0.8798 0.7169 0.0200 0.060 Uiso 1 1 calc R U . . .
C15 C 1.0000 1.0000 -0.3541(2) 0.0214(4) Uani 1 2 d S T P . .
C16 C 0.8796(2) 0.99100(16) -0.41144(17) 0.0257(4) Uani 1 1 d . . . . .
H16 H 0.7974 0.9842 -0.3735 0.031 Uiso 1 1 calc R U . . .
C17 C 0.8809(2) 0.99201(18) -0.52401(18) 0.0316(4) Uani 1 1 d . . . . .
H17 H 0.7989 0.9872 -0.5626 0.038 Uiso 1 1 calc R U . . .
C18 C 1.0000 1.0000 -0.5808(2) 0.0356(7) Uani 1 2 d S T P . .
H18 H 1.0000 1.0000 -0.6577 0.043 Uiso 1 2 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 Al1 2.1226(6) . ?
Al1 N1 1.8804(16) 2_775 ?
Al1 N1 1.8804(16) . ?
Al1 Cl1 2.1226(6) 2_775 ?
N1 C5 1.366(2) . ?
N1 C2 1.405(2) . ?
C1 C2 1.404(2) . ?
C1 C2 1.404(2) 2_775 ?
C1 C15 1.493(4) . ?
C2 C3 1.415(3) . ?
C3 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.483(3) . ?
C6 C11 1.400(3) . ?
C6 C7 1.404(3) . ?
C7 C8 1.387(3) . ?
C7 C12 1.505(3) . ?
C8 C9 1.386(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(3) . ?
C9 C13 1.502(3) . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C14 1.509(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.400(2) . ?
C15 C16 1.400(2) 2_775 ?
C16 C17 1.389(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(3) . ?
C17 H17 0.9500 . ?
C18 C17 1.385(3) 2_775 ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Al1 N1 95.59(10) 2_775 . ?
N1 Al1 Cl1 114.51(5) 2_775 2_775 ?
N1 Al1 Cl1 111.51(5) . 2_775 ?
N1 Al1 Cl1 111.51(5) 2_775 . ?
N1 Al1 Cl1 114.51(5) . . ?
Cl1 Al1 Cl1 108.86(5) 2_775 . ?
C5 N1 C2 106.88(15) . . ?
C5 N1 Al1 127.11(13) . . ?
C2 N1 Al1 125.83(12) . . ?
C2 C1 C2 124.2(2) . 2_775 ?
C2 C1 C15 117.88(11) . . ?
C2 C1 C15 117.88(11) 2_775 . ?
C1 C2 N1 123.90(16) . . ?
C1 C2 C3 128.01(17) . . ?
N1 C2 C3 108.00(16) . . ?
C4 C3 C2 107.53(18) . . ?
C4 C3 H3 126.2 . . ?
C2 C3 H3 126.2 . . ?
C3 C4 C5 107.58(17) . . ?
C3 C4 H4 126.2 . . ?
C5 C4 H4 126.2 . . ?
N1 C5 C4 109.95(17) . . ?
N1 C5 C6 120.23(17) . . ?
C4 C5 C6 129.55(17) . . ?
C11 C6 C7 120.50(18) . . ?
C11 C6 C5 117.98(17) . . ?
C7 C6 C5 121.52(17) . . ?
C8 C7 C6 118.60(18) . . ?
C8 C7 C12 120.08(19) . . ?
C6 C7 C12 121.3(2) . . ?
C9 C8 C7 121.96(19) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C10 118.37(18) . . ?
C8 C9 C13 120.8(2) . . ?
C10 C9 C13 120.8(2) . . ?
C11 C10 C9 121.71(19) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C6 118.77(18) . . ?
C10 C11 C14 119.68(19) . . ?
C6 C11 C14 121.55(19) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C16 119.3(2) . 2_775 ?
C16 C15 C1 120.35(12) . . ?
C16 C15 C1 120.35(12) 2_775 . ?
C17 C16 C15 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 120.9(2) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C17 119.3(3) . 2_775 ?
C17 C18 H18 120.4 . . ?
C17 C18 H18 120.4 2_775 . ?

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.057

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1480575'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H31 Al I2 N2'
_chemical_formula_sum            'C33 H31 Al I2 N2'
_chemical_formula_weight         736.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   21.089(4)
_cell_length_b                   13.041(3)
_cell_length_c                   23.489(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.897(3)
_cell_angle_gamma                90
_cell_volume                     6243(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9996
_cell_measurement_theta_min      2.168
_cell_measurement_theta_max      27.212

_exptl_crystal_description       chunk
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_F_000             2896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    2.067
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.665070
_exptl_absorpt_correction_T_max  0.746156
_exptl_absorpt_process_details   'twinabs (Sheldrick, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Duo with Apex II CCD'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9248
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.794
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             9248
_reflns_number_gt                8073
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin with an HKLF 5 file
 containing single reflections from the both components
 and composite reflections
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+14.2504P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9248
_refine_ls_number_parameters     350
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
Al1 Al 0.23140(6) 0.42861(9) 0.19176(5) 0.0162(2) Uani 1 1 d . . . . .
I1 I 0.20239(2) 0.33344(2) 0.09588(2) 0.02751(8) Uani 1 1 d . . . . .
I2 I 0.23297(2) 0.62059(2) 0.17864(2) 0.03781(10) Uani 1 1 d . . . . .
N1 N 0.17570(16) 0.3998(3) 0.24067(16) 0.0174(8) Uani 1 1 d . . . . .
N2 N 0.31182(17) 0.3940(3) 0.24493(16) 0.0173(8) Uani 1 1 d . . . . .
C1 C 0.2672(2) 0.4068(3) 0.33260(17) 0.0182(8) Uani 1 1 d . . . . .
C2 C 0.2002(2) 0.4022(3) 0.3024(2) 0.0186(9) Uani 1 1 d . . . . .
C4 C 0.0911(2) 0.3865(5) 0.2832(2) 0.0388(14) Uani 1 1 d . . . . .
H4 H 0.0478 0.3786 0.2875 0.047 Uiso 1 1 calc R U . . .
C5 C 0.1086(2) 0.3920(4) 0.2293(2) 0.0249(10) Uani 1 1 d . . . . .
C6 C 0.0629(2) 0.3895(4) 0.1693(2) 0.0232(10) Uani 1 1 d . . . . .
C7 C 0.0322(2) 0.4797(4) 0.1443(2) 0.0282(11) Uani 1 1 d . . . . .
C8 C -0.0143(2) 0.4750(4) 0.0900(2) 0.0327(11) Uani 1 1 d . . . . .
H8 H -0.0334 0.5369 0.0722 0.039 Uiso 1 1 calc R U . . .
C9 C -0.0335(2) 0.3828(4) 0.0612(2) 0.0347(12) Uani 1 1 d . . . . .
C10 C -0.0033(2) 0.2935(4) 0.0880(2) 0.0314(11) Uani 1 1 d . . . . .
H10 H -0.0163 0.2296 0.0692 0.038 Uiso 1 1 calc R U . . .
C11 C 0.0453(2) 0.2942(4) 0.1413(2) 0.0277(11) Uani 1 1 d . . . . .
C12 C 0.0469(3) 0.5820(4) 0.1752(3) 0.0428(14) Uani 1 1 d . . . . .
H12A H 0.0387 0.6372 0.1459 0.064 Uiso 1 1 calc R U . . .
H12B H 0.0930 0.5839 0.1977 0.064 Uiso 1 1 calc R U . . .
H12C H 0.0186 0.5913 0.2020 0.064 Uiso 1 1 calc R U . . .
C13 C -0.0855(3) 0.3798(5) 0.0033(3) 0.0532(17) Uani 1 1 d . . . . .
H13A H -0.0786 0.4369 -0.0216 0.080 Uiso 1 1 calc R U . . .
H13B H -0.1290 0.3858 0.0107 0.080 Uiso 1 1 calc R U . . .
H13C H -0.0825 0.3148 -0.0168 0.080 Uiso 1 1 calc R U . . .
C14 C 0.0771(3) 0.1962(4) 0.1672(2) 0.0402(13) Uani 1 1 d . . . . .
H14A H 0.0572 0.1386 0.1421 0.060 Uiso 1 1 calc R U . . .
H14B H 0.0706 0.1870 0.2067 0.060 Uiso 1 1 calc R U . . .
H14C H 0.1241 0.1990 0.1696 0.060 Uiso 1 1 calc R U . . .
C15 C 0.3191(2) 0.4002(3) 0.30610(19) 0.0184(9) Uani 1 1 d . . . . .
C16 C 0.3873(2) 0.3942(4) 0.3349(2) 0.0307(11) Uani 1 1 d . . . . .
H16 H 0.4064 0.3973 0.3761 0.037 Uiso 1 1 calc R U . . .
C18 C 0.3738(2) 0.3844(4) 0.2370(2) 0.0245(10) Uani 1 1 d . . . . .
C17 C 0.4203(2) 0.3833(4) 0.2922(2) 0.0337(12) Uani 1 1 d . . . . .
H17 H 0.4664 0.3762 0.2986 0.040 Uiso 1 1 calc R U . . .
C19 C 0.38851(19) 0.3785(4) 0.17881(19) 0.0222(9) Uani 1 1 d . . . . .
C20 C 0.4112(2) 0.4659(4) 0.1548(2) 0.0258(10) Uani 1 1 d . . . . .
C21 C 0.4299(2) 0.4563(4) 0.1022(2) 0.0340(12) Uani 1 1 d . . . . .
H21 H 0.4453 0.5153 0.0860 0.041 Uiso 1 1 calc R U . . .
C22 C 0.4269(2) 0.3639(5) 0.0729(2) 0.0389(14) Uani 1 1 d . . . . .
C23 C 0.4042(2) 0.2787(4) 0.0969(3) 0.0392(13) Uani 1 1 d . . . . .
H23 H 0.4014 0.2150 0.0768 0.047 Uiso 1 1 calc R U . . .
C24 C 0.3855(2) 0.2837(4) 0.1497(2) 0.0290(11) Uani 1 1 d . . . . .
C25 C 0.4165(3) 0.5689(4) 0.1850(3) 0.0385(13) Uani 1 1 d . . . . .
H25A H 0.4036 0.6231 0.1554 0.058 Uiso 1 1 calc R U . . .
H25B H 0.4620 0.5802 0.2077 0.058 Uiso 1 1 calc R U . . .
H25C H 0.3876 0.5704 0.2116 0.058 Uiso 1 1 calc R U . . .
C26 C 0.4466(3) 0.3572(6) 0.0151(3) 0.070(2) Uani 1 1 d . . . . .
H26A H 0.4408 0.2867 0.0003 0.106 Uiso 1 1 calc R U . . .
H26B H 0.4927 0.3773 0.0216 0.106 Uiso 1 1 calc R U . . .
H26C H 0.4189 0.4034 -0.0138 0.106 Uiso 1 1 calc R U . . .
C27 C 0.3642(3) 0.1880(4) 0.1753(3) 0.0453(14) Uani 1 1 d . . . . .
H27A H 0.3198 0.1976 0.1801 0.068 Uiso 1 1 calc R U . . .
H27B H 0.3945 0.1740 0.2138 0.068 Uiso 1 1 calc R U . . .
H27C H 0.3645 0.1301 0.1488 0.068 Uiso 1 1 calc R U . . .
C28 C 0.28094(19) 0.4217(3) 0.39776(18) 0.0197(9) Uani 1 1 d . . . . .
C29 C 0.2970(4) 0.3428(4) 0.4375(2) 0.060(2) Uani 1 1 d . . . . .
H29 H 0.3051 0.2764 0.4243 0.072 Uiso 1 1 calc R U . . .
C33 C 0.2740(3) 0.5173(5) 0.4192(2) 0.0520(17) Uani 1 1 d . . . . .
H33 H 0.2645 0.5737 0.3927 0.062 Uiso 1 1 calc R U . . .
C32 C 0.2805(4) 0.5336(5) 0.4785(3) 0.0584(18) Uani 1 1 d . . . . .
H32 H 0.2766 0.6011 0.4923 0.070 Uiso 1 1 calc R U . . .
C31 C 0.2924(2) 0.4542(5) 0.5172(2) 0.0381(13) Uani 1 1 d . . . . .
H31 H 0.2943 0.4651 0.5576 0.046 Uiso 1 1 calc R U . . .
C30 C 0.3015(4) 0.3590(5) 0.4972(2) 0.060(2) Uani 1 1 d . . . . .
H30 H 0.3110 0.3031 0.5240 0.072 Uiso 1 1 calc R U . . .
C3 C 0.1469(2) 0.3944(4) 0.3286(2) 0.0319(12) Uani 1 1 d . . . . .
H3 H 0.1493 0.3946 0.3696 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
Al1 N1 1.880(4) . ?
Al1 N2 1.885(4) . ?
Al1 I1 2.5055(13) . ?
Al1 I2 2.5236(13) . ?
N1 C5 1.374(5) . ?
N1 C2 1.409(5) . ?
N2 C18 1.372(5) . ?
N2 C15 1.407(5) . ?
C1 C15 1.394(6) . ?
C1 C2 1.411(6) . ?
C1 C28 1.495(5) . ?
C2 C3 1.417(6) . ?
C4 C3 1.374(7) . ?
C4 C5 1.409(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.489(6) . ?
C6 C7 1.398(7) . ?
C6 C11 1.411(7) . ?
C7 C8 1.396(6) . ?
C7 C12 1.511(7) . ?
C8 C9 1.388(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.397(7) . ?
C9 C13 1.513(7) . ?
C10 C11 1.398(7) . ?
C10 H10 0.9500 . ?
C11 C14 1.497(7) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.426(6) . ?
C16 C17 1.366(7) . ?
C16 H16 0.9500 . ?
C18 C17 1.410(6) . ?
C18 C19 1.480(6) . ?
C17 H17 0.9500 . ?
C19 C24 1.407(7) . ?
C19 C20 1.408(6) . ?
C20 C21 1.396(7) . ?
C20 C25 1.511(7) . ?
C21 C22 1.381(8) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(8) . ?
C22 C26 1.519(7) . ?
C23 C24 1.397(7) . ?
C23 H23 0.9500 . ?
C24 C27 1.503(7) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C33 1.366(7) . ?
C28 C29 1.372(7) . ?
C29 C30 1.397(7) . ?
C29 H29 0.9500 . ?
C33 C32 1.380(8) . ?
C33 H33 0.9500 . ?
C32 C31 1.358(9) . ?
C32 H32 0.9500 . ?
C31 C30 1.358(8) . ?
C31 H31 0.9500 . ?
C30 H30 0.9500 . ?
C3 H3 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Al1 N2 98.29(15) . . ?
N1 Al1 I1 113.81(12) . . ?
N2 Al1 I1 116.56(12) . . ?
N1 Al1 I2 107.64(12) . . ?
N2 Al1 I2 106.31(12) . . ?
I1 Al1 I2 112.92(5) . . ?
C5 N1 C2 106.7(3) . . ?
C5 N1 Al1 132.0(3) . . ?
C2 N1 Al1 120.2(3) . . ?
C18 N2 C15 106.6(3) . . ?
C18 N2 Al1 131.2(3) . . ?
C15 N2 Al1 120.4(3) . . ?
C15 C1 C2 125.0(4) . . ?
C15 C1 C28 119.8(4) . . ?
C2 C1 C28 115.2(4) . . ?
N1 C2 C1 124.9(4) . . ?
N1 C2 C3 108.9(4) . . ?
C1 C2 C3 126.1(4) . . ?
C3 C4 C5 108.9(4) . . ?
C3 C4 H4 125.5 . . ?
C5 C4 H4 125.5 . . ?
N1 C5 C4 108.9(4) . . ?
N1 C5 C6 124.7(4) . . ?
C4 C5 C6 126.4(4) . . ?
C7 C6 C11 120.5(4) . . ?
C7 C6 C5 119.7(4) . . ?
C11 C6 C5 119.4(4) . . ?
C8 C7 C6 119.1(5) . . ?
C8 C7 C12 119.1(5) . . ?
C6 C7 C12 121.7(4) . . ?
C9 C8 C7 122.2(5) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C8 C9 C10 117.4(5) . . ?
C8 C9 C13 121.0(5) . . ?
C10 C9 C13 121.6(5) . . ?
C9 C10 C11 122.8(5) . . ?
C9 C10 H10 118.6 . . ?
C11 C10 H10 118.6 . . ?
C10 C11 C6 117.9(5) . . ?
C10 C11 C14 120.4(5) . . ?
C6 C11 C14 121.7(4) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 C15 N2 124.6(4) . . ?
C1 C15 C16 127.2(4) . . ?
N2 C15 C16 108.2(4) . . ?
C17 C16 C15 107.4(4) . . ?
C17 C16 H16 126.3 . . ?
C15 C16 H16 126.3 . . ?
N2 C18 C17 109.7(4) . . ?
N2 C18 C19 124.3(4) . . ?
C17 C18 C19 125.9(4) . . ?
C16 C17 C18 108.0(4) . . ?
C16 C17 H17 126.0 . . ?
C18 C17 H17 126.0 . . ?
C24 C19 C20 119.6(4) . . ?
C24 C19 C18 120.0(4) . . ?
C20 C19 C18 120.1(4) . . ?
C21 C20 C19 119.1(5) . . ?
C21 C20 C25 119.4(5) . . ?
C19 C20 C25 121.5(4) . . ?
C22 C21 C20 122.1(5) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C21 C22 C23 118.3(5) . . ?
C21 C22 C26 120.4(6) . . ?
C23 C22 C26 121.3(6) . . ?
C22 C23 C24 122.0(5) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 H23 119.0 . . ?
C23 C24 C19 119.0(5) . . ?
C23 C24 C27 120.0(5) . . ?
C19 C24 C27 121.0(4) . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C33 C28 C29 117.7(4) . . ?
C33 C28 C1 119.0(4) . . ?
C29 C28 C1 123.3(4) . . ?
C28 C29 C30 120.7(5) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C28 C33 C32 121.3(6) . . ?
C28 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C31 C32 C33 120.8(6) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C30 C31 C32 118.9(5) . . ?
C30 C31 H31 120.5 . . ?
C32 C31 H31 120.5 . . ?
C31 C30 C29 120.4(5) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C4 C3 C2 106.5(4) . . ?
C4 C3 H3 126.8 . . ?
C2 C3 H3 126.8 . . ?

_refine_diff_density_max         0.669
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.101

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

data_4
_database_code_depnum_ccdc_archive 'CCDC 1480576'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H40 Al Cl N2 O'
_chemical_formula_sum            'C37 H40 Al Cl N2 O'
_chemical_formula_weight         591.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Al Al 0.2130 0.2455 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   15.4551(3)
_cell_length_b                   14.5277(3)
_cell_length_c                   15.9943(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.6960(10)
_cell_angle_gamma                90
_cell_volume                     3288.38(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9721
_cell_measurement_theta_min      3.042
_cell_measurement_theta_max      68.969

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.516
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6469
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_process_details   'sadabs (Sheldrick, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'ImuS microfocus sealed tube'
_diffrn_measurement_device_type  'Duo with Apex II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27612
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.123
_diffrn_reflns_theta_max         68.963
_diffrn_reflns_theta_full        68.963
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             5965
_reflns_number_gt                5032
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²+1.5056P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5965
_refine_ls_number_parameters     544
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.40809(12) 0.47035(12) 0.25141(12) 0.0208(4) Uani 1 1 d . . . . .
N1 N 0.31081(10) 0.39023(10) 0.31998(10) 0.0204(3) Uani 1 1 d . . . . .
O1 O 0.22555(11) 0.50566(11) 0.42470(12) 0.0232(3) Uani 0.95 1 d D U P A 1
Cl1 Cl 0.11650(3) 0.50558(3) 0.20375(3) 0.03062(14) Uani 0.95 1 d D . P A 1
Al1 Al 0.24254(4) 0.49714(4) 0.32697(4) 0.01958(15) Uani 0.95 1 d D . P A 1
N2 N 0.32843(10) 0.58383(10) 0.31249(10) 0.0205(3) Uani 1 1 d . . . . .
O2 O 0.1968(17) 0.518(3) 0.380(2) 0.038(8) Uani 0.05 1 d D U P A 3
Cl2 Cl 0.4231(11) 0.5028(8) 0.5202(7) 0.058(4) Uani 0.05 1 d D . P A 3
Al2 Al 0.3079(8) 0.5058(8) 0.3914(7) 0.028(2) Uani 0.05 1 d D . P A 3
C2 C 0.37452(12) 0.39071(12) 0.27737(12) 0.0208(4) Uani 1 1 d . . . . .
C3 C 0.40135(13) 0.29935(12) 0.27045(12) 0.0225(4) Uani 1 1 d . . . . .
H3 H 0.4423(14) 0.2846(14) 0.2452(13) 0.020(5) Uiso 1 1 d . . . . .
C4 C 0.35545(14) 0.24372(13) 0.30859(13) 0.0251(4) Uani 1 1 d . . . . .
H4 H 0.3609(16) 0.1825(17) 0.3160(15) 0.034(6) Uiso 1 1 d . . . . .
C5 C 0.30014(13) 0.30115(12) 0.33864(12) 0.0217(4) Uani 1 1 d . . . . .
C6 C 0.23680(13) 0.26823(12) 0.38175(12) 0.0225(4) Uani 1 1 d . . . . .
C7 C 0.26625(13) 0.27055(12) 0.47667(13) 0.0239(4) Uani 1 1 d . . . . .
C8 C 0.20772(14) 0.23173(13) 0.51472(13) 0.0270(4) Uani 1 1 d . . . . .
H8 H 0.2274(16) 0.2345(15) 0.5789(16) 0.031(6) Uiso 1 1 d . . . . .
C9 C 0.12107(14) 0.19239(13) 0.46064(13) 0.0273(4) Uani 1 1 d . . . . .
C10 C 0.09389(15) 0.19079(15) 0.36722(14) 0.0328(5) Uani 1 1 d . . . . .
H10 H 0.0350(19) 0.1645(18) 0.3304(17) 0.045(7) Uiso 1 1 d . . . . .
C11 C 0.15022(15) 0.22817(14) 0.32644(13) 0.0308(4) Uani 1 1 d . . . . .
C12 C 0.35835(15) 0.31549(16) 0.53675(14) 0.0323(5) Uani 1 1 d . . . . .
H12C H 0.412(2) 0.286(2) 0.5317(19) 0.056(8) Uiso 1 1 d . . . . .
H12B H 0.3590(19) 0.381(2) 0.5197(18) 0.049(7) Uiso 1 1 d . . . . .
H12A H 0.3686(19) 0.3128(18) 0.603(2) 0.052(7) Uiso 1 1 d . . . . .
H123 H 0.0541(19) 0.6192(18) 0.4563(18) 0.050(7) Uiso 1 1 d . . . . .
H122 H 0.216(2) 0.433(2) 0.5693(19) 0.059(8) Uiso 1 1 d . . . . .
H121 H 0.1043(18) 0.3763(19) 0.4242(17) 0.047(7) Uiso 1 1 d . . . . .
H113 H 0.152(2) 0.660(2) 0.4606(19) 0.057(8) Uiso 1 1 d . . . . .
H112 H 0.143(2) 0.5055(19) 0.578(2) 0.058(8) Uiso 1 1 d . . . . .
H111 H 0.0216(19) 0.4476(19) 0.4327(18) 0.054(8) Uiso 1 1 d . . . . .
C13 C 0.05641(16) 0.15442(15) 0.50210(15) 0.0346(5) Uani 1 1 d . . . . .
H13A H 0.0131 0.1096 0.4602 0.052 Uiso 1 1 calc R U . . .
H13B H 0.0200 0.2048 0.5129 0.052 Uiso 1 1 calc R U . . .
H13C H 0.0942 0.1242 0.5602 0.052 Uiso 1 1 calc R U . . .
C14 C 0.1166(2) 0.2263(2) 0.22387(17) 0.0509(7) Uani 1 1 d . . . . .
H14B H 0.145(3) 0.172(3) 0.210(2) 0.083(11) Uiso 1 1 d . . . . .
H14C H 0.145(3) 0.275(3) 0.204(3) 0.101(13) Uiso 1 1 d . . . . .
H14A H 0.048(3) 0.221(2) 0.193(2) 0.084(11) Uiso 1 1 d . . . . .
C15 C 0.38692(12) 0.56036(12) 0.26726(12) 0.0210(4) Uani 1 1 d . . . . .
C16 C 0.41927(13) 0.64245(12) 0.24171(13) 0.0233(4) Uani 1 1 d . . . . .
H16 H 0.4609(15) 0.6439(14) 0.2086(14) 0.026(5) Uiso 1 1 d . . . . .
C17 C 0.38229(13) 0.71468(13) 0.27174(13) 0.0246(4) Uani 1 1 d . . . . .
H17 H 0.3906(16) 0.7764(17) 0.2676(15) 0.032(6) Uiso 1 1 d . . . . .
C18 C 0.32651(12) 0.67684(12) 0.31488(12) 0.0206(4) Uani 1 1 d . . . . .
C19 C 0.27622(13) 0.73313(12) 0.35870(12) 0.0220(4) Uani 1 1 d . . . . .
C20 C 0.31209(13) 0.74001(14) 0.45406(13) 0.0281(4) Uani 1 1 d . . . . .
C21 C 0.27163(16) 0.80513(16) 0.49218(15) 0.0361(5) Uani 1 1 d . . . . .
H21 H 0.2966(17) 0.8095(17) 0.5566(17) 0.039(6) Uiso 1 1 d . . . . .
C22 C 0.19725(15) 0.86095(14) 0.43867(16) 0.0358(5) Uani 1 1 d . . . . .
C23 C 0.16066(15) 0.84974(14) 0.34492(16) 0.0341(5) Uani 1 1 d . . . . .
H23 H 0.1098(19) 0.8866(18) 0.3064(17) 0.047(7) Uiso 1 1 d . . . . .
C24 C 0.19927(14) 0.78717(13) 0.30329(14) 0.0270(4) Uani 1 1 d . . . . .
C25 C 0.39230(16) 0.68014(18) 0.51459(15) 0.0393(5) Uani 1 1 d . . . . .
H25C H 0.372(2) 0.611(2) 0.514(2) 0.075(10) Uiso 1 1 d . . . . .
H25B H 0.416(2) 0.698(2) 0.575(2) 0.072(9) Uiso 1 1 d . . . . .
H25A H 0.446(2) 0.680(2) 0.4981(19) 0.059(8) Uiso 1 1 d . . . . .
C26 C 0.1586(2) 0.93422(18) 0.4819(2) 0.0552(7) Uani 1 1 d . . . . .
H26A H 0.0903 0.9403 0.4469 0.083 Uiso 1 1 calc R U . . .
H26B H 0.1894 0.9932 0.4820 0.083 Uiso 1 1 calc R U . . .
H26C H 0.1711 0.9165 0.5448 0.083 Uiso 1 1 calc R U . . .
C27 C 0.15915(17) 0.77960(17) 0.20085(15) 0.0377(5) Uani 1 1 d . . . . .
H27C H 0.099(2) 0.809(2) 0.1759(19) 0.057(8) Uiso 1 1 d . . . . .
H27B H 0.204(2) 0.810(2) 0.178(2) 0.066(9) Uiso 1 1 d . . . . .
H27A H 0.156(2) 0.716(2) 0.1811(19) 0.060(8) Uiso 1 1 d . . . . .
C28 C 0.47375(13) 0.45867(12) 0.20432(13) 0.0225(4) Uani 1 1 d . . . . .
C29 C 0.44116(15) 0.42073(13) 0.11671(13) 0.0281(4) Uani 1 1 d . . . . .
H29 H 0.3799(16) 0.4053(15) 0.0892(14) 0.025(5) Uiso 1 1 d . . . . .
C30 C 0.50251(16) 0.41121(15) 0.07319(14) 0.0341(5) Uani 1 1 d . . . . .
H30 H 0.4798(16) 0.3864(16) 0.0134(16) 0.034(6) Uiso 1 1 d . . . . .
C31 C 0.59590(16) 0.43850(14) 0.11630(15) 0.0342(5) Uani 1 1 d . . . . .
H31 H 0.6353(17) 0.4283(16) 0.0872(15) 0.037(6) Uiso 1 1 d . . . . .
C32 C 0.62858(15) 0.47447(13) 0.20344(16) 0.0325(5) Uani 1 1 d . . . . .
H32 H 0.6927(18) 0.4933(15) 0.2346(16) 0.033(6) Uiso 1 1 d . . . . .
C33 C 0.56797(14) 0.48511(13) 0.24755(14) 0.0270(4) Uani 1 1 d . . . . .
H33 H 0.5904(16) 0.5091(15) 0.3086(16) 0.029(6) Uiso 1 1 d . . . . .
C100 C 0.14955(14) 0.51582(13) 0.45308(14) 0.0274(4) Uani 1 1 d . . . . .
C101 C 0.07399(16) 0.44310(16) 0.40819(16) 0.0371(5) Uani 1 1 d . . . . .
H101 H 0.0415(19) 0.4608(19) 0.3379(19) 0.051(7) Uiso 1 1 d . . . . .
C102 C 0.19220(18) 0.50217(19) 0.55625(16) 0.0406(5) Uani 1 1 d . . . . .
H102 H 0.242(2) 0.551(2) 0.582(2) 0.059(8) Uiso 1 1 d . . . . .
C103 C 0.10777(18) 0.61127(16) 0.4301(2) 0.0415(6) Uani 1 1 d . . . . .
H103 H 0.084(2) 0.616(2) 0.363(2) 0.062(9) Uiso 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 C15 1.396(3) . ?
C1 C2 1.398(2) . ?
C1 C28 1.497(2) . ?
N1 C5 1.353(2) . ?
N1 C2 1.405(2) . ?
N1 Al1 1.9060(15) . ?
N1 Al2 2.041(12) . ?
O1 C100 1.427(2) . ?
O1 Al1 1.6905(17) . ?
Cl1 Al1 2.1465(7) . ?
Al1 N2 1.9103(16) . ?
N2 C18 1.352(2) . ?
N2 C15 1.408(2) . ?
N2 Al2 1.816(11) . ?
O2 C100 1.61(3) . ?
O2 Al2 1.663(19) . ?
Cl2 Al2 2.115(13) . ?
Cl2 H25C 1.74(4) . ?
C2 C3 1.408(2) . ?
C3 C4 1.370(3) . ?
C3 H3 0.90(2) . ?
C4 C5 1.410(3) . ?
C4 H4 0.90(2) . ?
C5 C6 1.485(2) . ?
C6 C7 1.399(3) . ?
C6 C11 1.400(3) . ?
C7 C8 1.396(3) . ?
C7 C12 1.509(3) . ?
C8 C9 1.392(3) . ?
C8 H8 0.95(2) . ?
C9 C10 1.380(3) . ?
C9 C13 1.508(3) . ?
C10 C11 1.391(3) . ?
C10 H10 0.94(3) . ?
C11 C14 1.509(3) . ?
C12 H12C 0.96(3) . ?
C12 H12B 0.99(3) . ?
C12 H12A 1.00(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14B 0.97(4) . ?
C14 H14C 0.96(4) . ?
C14 H14A 0.97(4) . ?
C15 C16 1.415(2) . ?
C16 C17 1.371(3) . ?
C16 H16 0.98(2) . ?
C17 C18 1.414(2) . ?
C17 H17 0.91(2) . ?
C18 C19 1.484(2) . ?
C19 C20 1.401(3) . ?
C19 C24 1.403(3) . ?
C20 C21 1.402(3) . ?
C20 C25 1.505(3) . ?
C21 C22 1.386(3) . ?
C21 H21 0.95(2) . ?
C22 C23 1.383(3) . ?
C22 C26 1.517(3) . ?
C23 C24 1.395(3) . ?
C23 H23 0.95(3) . ?
C24 C27 1.505(3) . ?
C25 H25C 1.06(4) . ?
C25 H25B 0.92(3) . ?
C25 H25A 0.97(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27C 0.95(3) . ?
C27 H27B 1.00(3) . ?
C27 H27A 0.97(3) . ?
C28 C33 1.392(3) . ?
C28 C29 1.398(3) . ?
C29 C30 1.390(3) . ?
C29 H29 0.90(2) . ?
C30 C31 1.384(3) . ?
C30 H30 0.95(2) . ?
C31 C32 1.380(3) . ?
C31 H31 0.92(2) . ?
C32 C33 1.389(3) . ?
C32 H32 0.95(3) . ?
C33 H33 0.96(2) . ?
C100 C103 1.511(3) . ?
C100 C101 1.524(3) . ?
C100 C102 1.524(3) . ?
C101 H121 1.06(3) . ?
C101 H111 1.03(3) . ?
C101 H101 1.06(3) . ?
C102 H122 1.06(3) . ?
C102 H112 0.96(3) . ?
C102 H102 1.00(3) . ?
C103 H123 1.08(3) . ?
C103 H113 0.97(3) . ?
C103 H103 0.98(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
C15 C1 C2 125.41(16) . . ?
C15 C1 C28 116.97(15) . . ?
C2 C1 C28 117.61(15) . . ?
C5 N1 C2 106.45(14) . . ?
C5 N1 Al1 130.31(12) . . ?
C2 N1 Al1 122.48(11) . . ?
C5 N1 Al2 129.2(3) . . ?
C2 N1 Al2 116.4(3) . . ?
C100 O1 Al1 139.06(14) . . ?
O1 Al1 N1 114.16(8) . . ?
O1 Al1 N2 115.95(7) . . ?
N1 Al1 N2 95.86(7) . . ?
O1 Al1 Cl1 115.08(6) . . ?
N1 Al1 Cl1 108.19(5) . . ?
N2 Al1 Cl1 105.63(5) . . ?
C18 N2 C15 106.41(14) . . ?
C18 N2 Al2 126.3(4) . . ?
C15 N2 Al2 122.2(4) . . ?
C18 N2 Al1 129.13(12) . . ?
C15 N2 Al1 121.57(12) . . ?
C100 O2 Al2 132(2) . . ?
Al2 Cl2 H25C 74.8(12) . . ?
O2 Al2 N2 108.7(14) . . ?
O2 Al2 N1 106.4(14) . . ?
N2 Al2 N1 94.3(5) . . ?
O2 Al2 Cl2 122.4(14) . . ?
N2 Al2 Cl2 112.1(6) . . ?
N1 Al2 Cl2 109.2(6) . . ?
C1 C2 N1 124.37(15) . . ?
C1 C2 C3 126.92(16) . . ?
N1 C2 C3 108.63(15) . . ?
C4 C3 C2 107.43(16) . . ?
C4 C3 H3 129.9(13) . . ?
C2 C3 H3 122.7(13) . . ?
C3 C4 C5 107.23(16) . . ?
C3 C4 H4 127.3(15) . . ?
C5 C4 H4 125.4(15) . . ?
N1 C5 C4 110.26(16) . . ?
N1 C5 C6 124.89(16) . . ?
C4 C5 C6 124.82(16) . . ?
C7 C6 C11 120.47(17) . . ?
C7 C6 C5 120.55(16) . . ?
C11 C6 C5 118.79(16) . . ?
C8 C7 C6 118.55(17) . . ?
C8 C7 C12 120.53(17) . . ?
C6 C7 C12 120.91(17) . . ?
C9 C8 C7 121.68(17) . . ?
C9 C8 H8 120.0(14) . . ?
C7 C8 H8 118.3(14) . . ?
C10 C9 C8 118.55(18) . . ?
C10 C9 C13 120.17(18) . . ?
C8 C9 C13 121.27(18) . . ?
C9 C10 C11 121.70(19) . . ?
C9 C10 H10 118.6(15) . . ?
C11 C10 H10 119.7(15) . . ?
C10 C11 C6 119.04(18) . . ?
C10 C11 C14 119.72(19) . . ?
C6 C11 C14 121.23(18) . . ?
C7 C12 H12C 112.3(17) . . ?
C7 C12 H12B 110.6(16) . . ?
H12C C12 H12B 107(2) . . ?
C7 C12 H12A 111.3(16) . . ?
H12C C12 H12A 107(2) . . ?
H12B C12 H12A 108(2) . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14B 106(2) . . ?
C11 C14 H14C 110(2) . . ?
H14B C14 H14C 103(3) . . ?
C11 C14 H14A 112(2) . . ?
H14B C14 H14A 108(3) . . ?
H14C C14 H14A 116(3) . . ?
C1 C15 N2 124.47(16) . . ?
C1 C15 C16 126.96(16) . . ?
N2 C15 C16 108.57(15) . . ?
C17 C16 C15 107.37(16) . . ?
C17 C16 H16 128.9(12) . . ?
C15 C16 H16 123.8(12) . . ?
C16 C17 C18 107.17(16) . . ?
C16 C17 H17 129.5(14) . . ?
C18 C17 H17 123.3(14) . . ?
N2 C18 C17 110.49(15) . . ?
N2 C18 C19 125.85(16) . . ?
C17 C18 C19 123.64(16) . . ?
C20 C19 C24 120.77(17) . . ?
C20 C19 C18 120.02(16) . . ?
C24 C19 C18 118.81(16) . . ?
C19 C20 C21 118.11(19) . . ?
C19 C20 C25 121.47(18) . . ?
C21 C20 C25 120.42(19) . . ?
C22 C21 C20 122.1(2) . . ?
C22 C21 H21 120.5(15) . . ?
C20 C21 H21 117.4(15) . . ?
C23 C22 C21 118.48(19) . . ?
C23 C22 C26 120.8(2) . . ?
C21 C22 C26 120.7(2) . . ?
C22 C23 C24 121.8(2) . . ?
C22 C23 H23 120.6(16) . . ?
C24 C23 H23 117.5(16) . . ?
C23 C24 C19 118.67(19) . . ?
C23 C24 C27 119.96(19) . . ?
C19 C24 C27 121.37(18) . . ?
C20 C25 H25C 112.5(18) . . ?
C20 C25 H25B 113(2) . . ?
H25C C25 H25B 106(3) . . ?
C20 C25 H25A 113.5(17) . . ?
H25C C25 H25A 106(2) . . ?
H25B C25 H25A 105(3) . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27C 109.1(17) . . ?
C24 C27 H27B 108.7(18) . . ?
H27C C27 H27B 110(2) . . ?
C24 C27 H27A 111.6(17) . . ?
H27C C27 H27A 112(2) . . ?
H27B C27 H27A 105(2) . . ?
C33 C28 C29 119.37(18) . . ?
C33 C28 C1 120.29(17) . . ?
C29 C28 C1 120.34(17) . . ?
C30 C29 C28 119.8(2) . . ?
C30 C29 H29 121.8(14) . . ?
C28 C29 H29 118.3(14) . . ?
C31 C30 C29 120.4(2) . . ?
C31 C30 H30 120.0(14) . . ?
C29 C30 H30 119.5(14) . . ?
C32 C31 C30 119.77(19) . . ?
C32 C31 H31 121.8(15) . . ?
C30 C31 H31 118.3(15) . . ?
C31 C32 C33 120.5(2) . . ?
C31 C32 H32 121.3(14) . . ?
C33 C32 H32 118.3(14) . . ?
C32 C33 C28 120.09(19) . . ?
C32 C33 H33 121.0(13) . . ?
C28 C33 H33 118.9(13) . . ?
O1 C100 C103 110.07(16) . . ?
O1 C100 C101 110.57(16) . . ?
C103 C100 C101 110.49(18) . . ?
O1 C100 C102 106.13(17) . . ?
C103 C100 C102 109.85(19) . . ?
C101 C100 C102 109.64(18) . . ?
C103 C100 O2 94.5(13) . . ?
C101 C100 O2 99.1(13) . . ?
C102 C100 O2 131.6(11) . . ?
C100 C101 H121 109.8(14) . . ?
C100 C101 H111 110.3(16) . . ?
H121 C101 H111 108(2) . . ?
C100 C101 H101 106.1(15) . . ?
H121 C101 H101 117(2) . . ?
H111 C101 H101 106(2) . . ?
C100 C102 H122 107.5(15) . . ?
C100 C102 H112 109.0(18) . . ?
H122 C102 H112 104(2) . . ?
C100 C102 H102 106.2(17) . . ?
H122 C102 H102 116(2) . . ?
H112 C102 H102 114(2) . . ?
C100 C103 H123 108.9(14) . . ?
C100 C103 H113 113.8(17) . . ?
H123 C103 H113 103(2) . . ?
C100 C103 H103 105.4(18) . . ?
H123 C103 H103 114(2) . . ?
H113 C103 H103 112(2) . . ?

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1480577'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C41 H49 Al N2 O2'
_chemical_formula_sum            'C41 H49 Al N2 O2'
_chemical_formula_weight         628.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Al Al 0.2130 0.2455 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   13.9055(3)
_cell_length_b                   15.3152(3)
_cell_length_c                   17.3140(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3687.28(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      3.854
_cell_measurement_theta_max      68.410

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_F_000             1352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.748
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6927
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'sadabs (Sheldrick, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'ImuS microfocus sealed tube'
_diffrn_measurement_device_type  'Duo with Apex II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16862
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.853
_diffrn_reflns_theta_max         68.901
_diffrn_reflns_theta_full        68.901
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             6728
_reflns_number_gt                6299
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.973

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0482P)²+0.7533P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2632 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6728
_refine_ls_number_parameters     460
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.99695(4) 0.05324(4) 0.97996(3) 0.01930(15) Uani 1 1 d . . . . .
O1 O 1.02839(11) -0.05445(10) 0.97995(10) 0.0296(4) Uani 1 1 d . . . . .
C1 C 0.76673(15) 0.04304(15) 0.96713(14) 0.0239(5) Uani 1 1 d . . . . .
N1 N 0.91453(13) 0.08134(12) 0.89516(11) 0.0209(4) Uani 1 1 d . . . . .
N2 N 0.90066(13) 0.07324(12) 1.05701(11) 0.0215(4) Uani 1 1 d . . . . .
O2 O 1.08933(10) 0.12535(10) 0.98878(9) 0.0215(3) Uani 1 1 d . . . . .
C2 C 0.81627(15) 0.06158(15) 0.89880(13) 0.0239(5) Uani 1 1 d . . . . .
C3 C 0.77657(17) 0.07139(17) 0.82415(14) 0.0301(5) Uani 1 1 d . . . . .
H3 H 0.7113 0.0623 0.8101 0.036 Uiso 1 1 calc R U . . .
C4 C 0.84953(19) 0.09644(17) 0.77573(14) 0.0314(6) Uani 1 1 d . . . . .
H4 H 0.8443 0.1077 0.7219 0.038 Uiso 1 1 calc R U . . .
C5 C 0.93345(17) 0.10232(15) 0.82054(13) 0.0237(5) Uani 1 1 d . . . . .
C6 C 1.02790(16) 0.13444(15) 0.79217(12) 0.0233(5) Uani 1 1 d . . . . .
C7 C 1.08257(19) 0.08461(16) 0.74069(13) 0.0291(5) Uani 1 1 d . . . . .
C8 C 1.16770(19) 0.11976(18) 0.71174(14) 0.0323(6) Uani 1 1 d . . . . .
H8 H 1.2056 0.0858 0.6774 0.039 Uiso 1 1 calc R U . . .
C9 C 1.19868(19) 0.20264(18) 0.73151(14) 0.0324(6) Uani 1 1 d . . . . .
C10 C 1.14247(18) 0.25129(17) 0.78147(14) 0.0295(5) Uani 1 1 d . . . . .
H10 H 1.1628 0.3085 0.7951 0.035 Uiso 1 1 calc R U . . .
C11 C 1.05735(17) 0.21930(15) 0.81234(13) 0.0250(5) Uani 1 1 d . . . . .
C12 C 1.0518(2) -0.00537(19) 0.71557(18) 0.0433(7) Uani 1 1 d . . . . .
H12A H 1.1088 -0.0404 0.7034 0.065 Uiso 1 1 calc R U . . .
H12B H 1.0109 -0.0008 0.6697 0.065 Uiso 1 1 calc R U . . .
H12C H 1.0158 -0.0335 0.7574 0.065 Uiso 1 1 calc R U . . .
C13 C 1.2904(2) 0.2396(2) 0.69787(18) 0.0463(7) Uani 1 1 d . . . . .
H13A H 1.3135 0.2874 0.7306 0.069 Uiso 1 1 calc R U . . .
H13B H 1.2778 0.2616 0.6457 0.069 Uiso 1 1 calc R U . . .
H13C H 1.3393 0.1936 0.6955 0.069 Uiso 1 1 calc R U . . .
C14 C 0.99729(19) 0.27520(16) 0.86564(14) 0.0309(5) Uani 1 1 d . . . . .
H14A H 1.0174 0.3363 0.8610 0.046 Uiso 1 1 calc R U . . .
H14B H 1.0062 0.2556 0.9190 0.046 Uiso 1 1 calc R U . . .
H14C H 0.9293 0.2699 0.8514 0.046 Uiso 1 1 calc R U . . .
C15 C 0.80509(15) 0.04895(15) 1.04176(13) 0.0237(5) Uani 1 1 d . . . . .
C16 C 0.75731(17) 0.03639(17) 1.11334(15) 0.0305(5) Uani 1 1 d . . . . .
H16 H 0.6925 0.0185 1.1202 0.037 Uiso 1 1 calc R U . . .
C17 C 0.82198(17) 0.05486(17) 1.17057(14) 0.0299(5) Uani 1 1 d . . . . .
H17 H 0.8099 0.0532 1.2245 0.036 Uiso 1 1 calc R U . . .
C18 C 0.91019(16) 0.07692(14) 1.13486(13) 0.0232(5) Uani 1 1 d . . . . .
C19 C 0.99838(17) 0.10515(15) 1.17554(12) 0.0231(5) Uani 1 1 d . . . . .
C20 C 1.04873(17) 0.04598(18) 1.22239(13) 0.0298(5) Uani 1 1 d . . . . .
C21 C 1.12809(19) 0.0752(2) 1.26342(14) 0.0351(6) Uani 1 1 d . . . . .
H21 H 1.1632 0.0349 1.2940 0.042 Uiso 1 1 calc R U . . .
C22 C 1.15756(19) 0.1613(2) 1.26112(14) 0.0364(6) Uani 1 1 d . . . . .
C23 C 1.10583(19) 0.21970(18) 1.21491(14) 0.0337(6) Uani 1 1 d . . . . .
H23 H 1.1249 0.2792 1.2132 0.040 Uiso 1 1 calc R U . . .
C24 C 1.02726(17) 0.19273(16) 1.17139(13) 0.0255(5) Uani 1 1 d . . . . .
C25 C 1.0191(2) -0.04848(19) 1.2277(2) 0.0503(8) Uani 1 1 d . . . . .
H25A H 1.0693 -0.0817 1.2544 0.075 Uiso 1 1 calc R U . . .
H25B H 1.0101 -0.0721 1.1756 0.075 Uiso 1 1 calc R U . . .
H25C H 0.9587 -0.0530 1.2566 0.075 Uiso 1 1 calc R U . . .
C26 C 1.2439(2) 0.1920(3) 1.30690(19) 0.0575(9) Uani 1 1 d . . . . .
H26A H 1.2246 0.2397 1.3413 0.086 Uiso 1 1 calc R U . . .
H26B H 1.2938 0.2126 1.2714 0.086 Uiso 1 1 calc R U . . .
H26C H 1.2691 0.1434 1.3377 0.086 Uiso 1 1 calc R U . . .
C27 C 0.97469(18) 0.25740(16) 1.12151(15) 0.0324(6) Uani 1 1 d . . . . .
H27A H 0.9951 0.3167 1.1350 0.049 Uiso 1 1 calc R U . . .
H27B H 0.9053 0.2516 1.1300 0.049 Uiso 1 1 calc R U . . .
H27C H 0.9894 0.2460 1.0671 0.049 Uiso 1 1 calc R U . . .
C28 C 0.66432(16) 0.01531(15) 0.95961(14) 0.0266(5) Uani 1 1 d . . . . .
C29 C 0.64185(18) -0.06049(18) 0.91893(16) 0.0355(6) Uani 1 1 d . . . . .
H29 H 0.6916 -0.0931 0.8947 0.043 Uiso 1 1 calc R U . . .
C30 C 0.54717(19) -0.08862(17) 0.91357(18) 0.0389(7) Uani 1 1 d . . . . .
H30 H 0.5323 -0.1407 0.8863 0.047 Uiso 1 1 calc R U . . .
C31 C 0.47432(17) -0.04074(18) 0.94795(16) 0.0364(6) Uani 1 1 d . . . . .
H31 H 0.4096 -0.0603 0.9448 0.044 Uiso 1 1 calc R U . . .
C32 C 0.49599(17) 0.03576(17) 0.98702(15) 0.0329(5) Uani 1 1 d . . . . .
H32 H 0.4459 0.0691 1.0099 0.039 Uiso 1 1 calc R U . . .
C33 C 0.59046(16) 0.06382(16) 0.99278(14) 0.0283(5) Uani 1 1 d . . . . .
H33 H 0.6049 0.1164 1.0195 0.034 Uiso 1 1 calc R U . . .
C100 C 0.99856(19) -0.14143(15) 0.96998(15) 0.0319(5) Uani 1 1 d . . . . .
C101 C 0.9176(3) -0.1639(2) 1.0241(3) 0.0771(14) Uani 1 1 d . . . . .
H101 H 0.8993 -0.2251 1.0169 0.116 Uiso 1 1 calc R U . . .
H111 H 0.8622 -0.1263 1.0131 0.116 Uiso 1 1 calc R U . . .
H121 H 0.9385 -0.1548 1.0776 0.116 Uiso 1 1 calc R U . . .
C102 C 0.9696(4) -0.1545(2) 0.8860(2) 0.0748(13) Uani 1 1 d . . . . .
H102 H 0.9487 -0.2149 0.8783 0.112 Uiso 1 1 calc R U . . .
H112 H 1.0247 -0.1421 0.8525 0.112 Uiso 1 1 calc R U . . .
H122 H 0.9167 -0.1147 0.8732 0.112 Uiso 1 1 calc R U . . .
C103 C 1.0850(2) -0.19850(19) 0.9858(2) 0.0516(8) Uani 1 1 d . . . . .
H103 H 1.0684 -0.2596 0.9758 0.077 Uiso 1 1 calc R U . . .
H113 H 1.1044 -0.1919 1.0399 0.077 Uiso 1 1 calc R U . . .
H123 H 1.1381 -0.1810 0.9521 0.077 Uiso 1 1 calc R U . . .
C200 C 1.19123(15) 0.11756(15) 0.99282(13) 0.0218(5) Uani 1 1 d . . . . .
C201 C 1.22941(17) 0.07559(18) 0.91920(14) 0.0275(5) Uani 1 1 d . . . . .
H221 H 1.299(2) 0.0711(18) 0.9175(15) 0.029(7) Uiso 1 1 d . . . . .
H211 H 1.211(2) 0.108(2) 0.8748(18) 0.040(8) Uiso 1 1 d . . . . .
H201 H 1.207(3) 0.013(2) 0.912(2) 0.056(10) Uiso 1 1 d . . . . .
C202 C 1.23116(18) 0.20974(18) 1.00158(16) 0.0316(6) Uani 1 1 d . . . . .
H222 H 1.301(2) 0.2103(18) 1.0076(17) 0.036(7) Uiso 1 1 d . . . . .
H212 H 1.214(2) 0.246(2) 0.9568(19) 0.040(8) Uiso 1 1 d . . . . .
H202 H 1.205(2) 0.236(2) 1.0462(19) 0.038(8) Uiso 1 1 d . . . . .
C203 C 1.21869(17) 0.0618(2) 1.06281(14) 0.0310(5) Uani 1 1 d . . . . .
H223 H 1.189(2) 0.003(2) 1.0585(18) 0.041(8) Uiso 1 1 d . . . . .
H213 H 1.288(2) 0.054(2) 1.0641(17) 0.039(8) Uiso 1 1 d . . . . .
H203 H 1.194(2) 0.0870(18) 1.1090(17) 0.032(7) Uiso 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
Al1 O2 1.7009(16) . ?
Al1 O1 1.7063(17) . ?
Al1 N1 1.9117(19) . ?
Al1 N2 1.9148(19) . ?
O1 C100 1.406(3) . ?
C1 C2 1.398(3) . ?
C1 C15 1.401(3) . ?
C1 C28 1.492(3) . ?
N1 C5 1.357(3) . ?
N1 C2 1.401(3) . ?
N2 C18 1.356(3) . ?
N2 C15 1.405(3) . ?
O2 C200 1.424(2) . ?
C2 C3 1.413(3) . ?
C3 C4 1.371(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.486(3) . ?
C6 C7 1.398(3) . ?
C6 C11 1.407(3) . ?
C7 C8 1.394(4) . ?
C7 C12 1.507(4) . ?
C8 C9 1.383(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(4) . ?
C9 C13 1.512(4) . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C14 1.511(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.419(3) . ?
C16 C17 1.368(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.415(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.479(3) . ?
C19 C24 1.402(3) . ?
C19 C20 1.403(3) . ?
C20 C21 1.387(4) . ?
C20 C25 1.507(4) . ?
C21 C22 1.381(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.399(4) . ?
C22 C26 1.513(4) . ?
C23 C24 1.390(3) . ?
C23 H23 0.9500 . ?
C24 C27 1.504(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C33 1.392(3) . ?
C28 C29 1.393(4) . ?
C29 C30 1.388(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.385(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.386(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.386(3) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C100 C101 1.505(4) . ?
C100 C103 1.511(4) . ?
C100 C102 1.522(4) . ?
C101 H101 0.9800 . ?
C101 H111 0.9800 . ?
C101 H121 0.9800 . ?
C102 H102 0.9800 . ?
C102 H112 0.9800 . ?
C102 H122 0.9800 . ?
C103 H103 0.9800 . ?
C103 H113 0.9800 . ?
C103 H123 0.9800 . ?
C200 C201 1.523(3) . ?
C200 C202 1.525(3) . ?
C200 C203 1.531(3) . ?
C201 H221 0.97(3) . ?
C201 H211 0.95(3) . ?
C201 H201 1.02(4) . ?
C202 H222 0.98(3) . ?
C202 H212 0.98(3) . ?
C202 H202 0.95(3) . ?
C203 H223 0.99(3) . ?
C203 H213 0.98(3) . ?
C203 H203 0.95(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
O2 Al1 O1 115.73(8) . . ?
O2 Al1 N1 112.06(8) . . ?
O1 Al1 N1 111.79(8) . . ?
O2 Al1 N2 111.20(8) . . ?
O1 Al1 N2 109.51(9) . . ?
N1 Al1 N2 94.58(8) . . ?
C100 O1 Al1 147.18(16) . . ?
C2 C1 C15 125.4(2) . . ?
C2 C1 C28 117.0(2) . . ?
C15 C1 C28 117.5(2) . . ?
C5 N1 C2 106.45(19) . . ?
C5 N1 Al1 131.94(16) . . ?
C2 N1 Al1 120.10(15) . . ?
C18 N2 C15 106.88(18) . . ?
C18 N2 Al1 129.12(15) . . ?
C15 N2 Al1 119.22(15) . . ?
C200 O2 Al1 134.56(14) . . ?
C1 C2 N1 124.2(2) . . ?
C1 C2 C3 127.1(2) . . ?
N1 C2 C3 108.5(2) . . ?
C4 C3 C2 107.5(2) . . ?
C4 C3 H3 126.3 . . ?
C2 C3 H3 126.3 . . ?
C3 C4 C5 107.2(2) . . ?
C3 C4 H4 126.4 . . ?
C5 C4 H4 126.4 . . ?
N1 C5 C4 110.5(2) . . ?
N1 C5 C6 124.4(2) . . ?
C4 C5 C6 125.0(2) . . ?
C7 C6 C11 120.3(2) . . ?
C7 C6 C5 120.7(2) . . ?
C11 C6 C5 118.8(2) . . ?
C8 C7 C6 118.7(2) . . ?
C8 C7 C12 119.4(2) . . ?
C6 C7 C12 121.9(2) . . ?
C9 C8 C7 122.0(2) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C10 118.2(2) . . ?
C8 C9 C13 120.7(3) . . ?
C10 C9 C13 121.1(3) . . ?
C9 C10 C11 122.2(2) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C10 C11 C6 118.6(2) . . ?
C10 C11 C14 120.4(2) . . ?
C6 C11 C14 120.9(2) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 C15 N2 123.4(2) . . ?
C1 C15 C16 128.2(2) . . ?
N2 C15 C16 108.33(19) . . ?
C17 C16 C15 107.3(2) . . ?
C17 C16 H16 126.4 . . ?
C15 C16 H16 126.4 . . ?
C16 C17 C18 107.6(2) . . ?
C16 C17 H17 126.2 . . ?
C18 C17 H17 126.2 . . ?
N2 C18 C17 109.9(2) . . ?
N2 C18 C19 124.54(19) . . ?
C17 C18 C19 125.5(2) . . ?
C24 C19 C20 120.3(2) . . ?
C24 C19 C18 119.5(2) . . ?
C20 C19 C18 120.0(2) . . ?
C21 C20 C19 119.0(2) . . ?
C21 C20 C25 119.8(2) . . ?
C19 C20 C25 121.3(2) . . ?
C22 C21 C20 122.0(2) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C21 C22 C23 118.3(2) . . ?
C21 C22 C26 121.1(3) . . ?
C23 C22 C26 120.6(3) . . ?
C24 C23 C22 121.6(3) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C23 C24 C19 118.8(2) . . ?
C23 C24 C27 119.9(2) . . ?
C19 C24 C27 121.4(2) . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C33 C28 C29 119.2(2) . . ?
C33 C28 C1 121.1(2) . . ?
C29 C28 C1 119.7(2) . . ?
C30 C29 C28 120.3(2) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C31 C30 C29 120.0(2) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C32 119.9(2) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C33 C32 C31 120.2(2) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C32 C33 C28 120.3(2) . . ?
C32 C33 H33 119.9 . . ?
C28 C33 H33 119.9 . . ?
O1 C100 C101 111.1(2) . . ?
O1 C100 C103 106.9(2) . . ?
C101 C100 C103 110.5(3) . . ?
O1 C100 C102 108.7(2) . . ?
C101 C100 C102 111.5(3) . . ?
C103 C100 C102 107.9(3) . . ?
C100 C101 H101 109.5 . . ?
C100 C101 H111 109.5 . . ?
H101 C101 H111 109.5 . . ?
C100 C101 H121 109.5 . . ?
H101 C101 H121 109.5 . . ?
H111 C101 H121 109.5 . . ?
C100 C102 H102 109.5 . . ?
C100 C102 H112 109.5 . . ?
H102 C102 H112 109.5 . . ?
C100 C102 H122 109.5 . . ?
H102 C102 H122 109.5 . . ?
H112 C102 H122 109.5 . . ?
C100 C103 H103 109.5 . . ?
C100 C103 H113 109.5 . . ?
H103 C103 H113 109.5 . . ?
C100 C103 H123 109.5 . . ?
H103 C103 H123 109.5 . . ?
H113 C103 H123 109.5 . . ?
O2 C200 C201 109.95(18) . . ?
O2 C200 C202 106.85(19) . . ?
C201 C200 C202 110.3(2) . . ?
O2 C200 C203 109.50(18) . . ?
C201 C200 C203 109.9(2) . . ?
C202 C200 C203 110.3(2) . . ?
C200 C201 H221 113.7(16) . . ?
C200 C201 H211 111.3(18) . . ?
H221 C201 H211 107(2) . . ?
C200 C201 H201 113(2) . . ?
H221 C201 H201 104(3) . . ?
H211 C201 H201 108(3) . . ?
C200 C202 H222 112.4(16) . . ?
C200 C202 H212 111.1(18) . . ?
H222 C202 H212 108(2) . . ?
C200 C202 H202 109.6(19) . . ?
H222 C202 H202 107(3) . . ?
H212 C202 H202 108(2) . . ?
C200 C203 H223 109.9(18) . . ?
C200 C203 H213 109.5(18) . . ?
H223 C203 H213 108(3) . . ?
C200 C203 H203 110.3(17) . . ?
H223 C203 H203 106(3) . . ?
H213 C203 H203 113(2) . . ?

_refine_diff_density_max         0.315
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1480578'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H43 Al N4'
_chemical_formula_sum            'C37 H43 Al N4'
_chemical_formula_weight         570.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   10.1588(17)
_cell_length_b                   16.568(3)
_cell_length_c                   19.274(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.011(3)
_cell_angle_gamma                90
_cell_volume                     3239.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9971
_cell_measurement_theta_min      2.220
_cell_measurement_theta_max      31.071

_exptl_crystal_description       chunk
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7004
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'sadabs (Sheldrick, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Duo with Apex II CCD'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44155
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.622
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        26.000
_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             7830
_reflns_number_gt                6054
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0592P)²+0.9347P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7830
_refine_ls_number_parameters     527
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1161
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.20540(4) 0.70965(2) 0.01998(2) 0.01644(10) Uani 1 1 d . . . . .
N1 N 0.18536(11) 0.79028(6) -0.05204(6) 0.0159(2) Uani 1 1 d . . . . .
N2 N 0.30332(11) 0.78013(6) 0.08240(6) 0.0159(2) Uani 1 1 d . . . . .
N3 N 0.04843(13) 0.69147(8) 0.05620(7) 0.0280(3) Uani 1 1 d . . . . .
N4 N 0.30270(14) 0.62615(8) -0.00685(7) 0.0307(3) Uani 1 1 d . . . . .
C1 C 0.25460(13) 0.90808(8) 0.02020(7) 0.0157(3) Uani 1 1 d . . . . .
C2 C 0.19239(13) 0.87374(8) -0.03964(7) 0.0160(3) Uani 1 1 d . . . . .
C3 C 0.13519(14) 0.91451(8) -0.09856(7) 0.0191(3) Uani 1 1 d . . . . .
H3 H 0.1266(15) 0.9727(10) -0.1038(8) 0.020(4) Uiso 1 1 d . . . . .
C4 C 0.09712(14) 0.85649(8) -0.14684(7) 0.0209(3) Uani 1 1 d . . . . .
H4 H 0.0582(16) 0.8642(10) -0.1934(9) 0.023(4) Uiso 1 1 d . . . . .
C5 C 0.12994(13) 0.78080(8) -0.11717(7) 0.0168(3) Uani 1 1 d . . . . .
C6 C 0.12400(13) 0.70087(8) -0.15272(7) 0.0168(3) Uani 1 1 d . . . . .
C7 C 0.02155(13) 0.64535(8) -0.14431(7) 0.0178(3) Uani 1 1 d . . . . .
C8 C 0.02718(14) 0.57009(8) -0.17668(7) 0.0191(3) Uani 1 1 d . . . . .
H8 H -0.0457(16) 0.5313(10) -0.1701(8) 0.020(4) Uiso 1 1 d . . . . .
C9 C 0.12828(14) 0.54988(8) -0.21937(7) 0.0200(3) Uani 1 1 d . . . . .
C10 C 0.22525(14) 0.60742(9) -0.23002(7) 0.0217(3) Uani 1 1 d . . . . .
H10 H 0.2952(16) 0.5963(10) -0.2601(8) 0.025(4) Uiso 1 1 d . . . . .
C11 C 0.22543(14) 0.68245(8) -0.19744(7) 0.0197(3) Uani 1 1 d . . . . .
C12 C -0.09738(14) 0.66691(9) -0.10465(8) 0.0252(3) Uani 1 1 d . . . . .
H12A H -0.1392 0.6174 -0.0887 0.038 Uiso 1 1 calc R U . . .
H12B H -0.1603 0.6970 -0.1350 0.038 Uiso 1 1 calc R U . . .
H12C H -0.0700 0.7003 -0.0645 0.038 Uiso 1 1 calc R U . . .
H14B H 0.299(2) 0.7872(13) -0.2393(11) 0.048(6) Uiso 1 1 d . . . . .
H14A H 0.374(2) 0.7664(13) -0.1691(12) 0.056(6) Uiso 1 1 d . . . . .
C13 C 0.13313(18) 0.46835(9) -0.25422(9) 0.0282(3) Uani 1 1 d . . . . .
H13B H 0.165(2) 0.4717(15) -0.2997(14) 0.075(8) Uiso 1 1 d . . . . .
H13A H 0.193(3) 0.4307(17) -0.2311(14) 0.086(9) Uiso 1 1 d . . . . .
H13 H 0.050(3) 0.4414(17) -0.2587(14) 0.088(9) Uiso 1 1 d . . . . .
C14 C 0.33265(16) 0.74265(10) -0.21098(9) 0.0285(3) Uani 1 1 d . . . . .
H14 H 0.403(2) 0.7202(13) -0.2363(11) 0.056(6) Uiso 1 1 d . . . . .
C15 C 0.31062(13) 0.86422(8) 0.07665(7) 0.0158(3) Uani 1 1 d . . . . .
C16 C 0.38828(13) 0.89424(8) 0.13461(7) 0.0185(3) Uani 1 1 d . . . . .
H16 H 0.4110(17) 0.9513(11) 0.1433(9) 0.031(5) Uiso 1 1 d . . . . .
C17 C 0.42706(14) 0.82889(8) 0.17469(7) 0.0198(3) Uani 1 1 d . . . . .
H17 H 0.4811(17) 0.8294(10) 0.2153(9) 0.026(4) Uiso 1 1 d . . . . .
C18 C 0.37259(13) 0.75959(8) 0.14184(7) 0.0167(3) Uani 1 1 d . . . . .
C19 C 0.38109(13) 0.67521(8) 0.16803(7) 0.0162(3) Uani 1 1 d . . . . .
C20 C 0.28150(13) 0.64558(8) 0.20898(7) 0.0180(3) Uani 1 1 d . . . . .
C21 C 0.28796(14) 0.56570(9) 0.23138(7) 0.0203(3) Uani 1 1 d . . . . .
H21 H 0.2188(16) 0.5449(10) 0.2584(8) 0.023(4) Uiso 1 1 d . . . . .
C22 C 0.39146(14) 0.51501(8) 0.21535(7) 0.0208(3) Uani 1 1 d . . . . .
C23 C 0.49251(14) 0.54699(8) 0.17762(7) 0.0202(3) Uani 1 1 d . . . . .
H23 H 0.5657(18) 0.5142(11) 0.1659(9) 0.030(4) Uiso 1 1 d . . . . .
C24 C 0.48982(13) 0.62647(8) 0.15392(7) 0.0184(3) Uani 1 1 d . . . . .
C25 C 0.16972(16) 0.69901(10) 0.22920(9) 0.0258(3) Uani 1 1 d . . . . .
H25A H 0.201(2) 0.7495(14) 0.2499(11) 0.055(6) Uiso 1 1 d . . . . .
H25B H 0.116(2) 0.7160(15) 0.1917(14) 0.073(8) Uiso 1 1 d . . . . .
H25 H 0.115(2) 0.6738(13) 0.2615(12) 0.056(6) Uiso 1 1 d . . . . .
C26 C 0.39419(19) 0.42804(10) 0.23873(10) 0.0324(4) Uani 1 1 d . . . . .
H26A H 0.451(2) 0.4221(13) 0.2797(12) 0.060(7) Uiso 1 1 d . . . . .
H26B H 0.430(2) 0.3909(13) 0.2023(11) 0.055(6) Uiso 1 1 d . . . . .
H26 H 0.310(2) 0.4093(13) 0.2529(11) 0.056(6) Uiso 1 1 d . . . . .
C27 C 0.60260(17) 0.65981(11) 0.11496(9) 0.0298(3) Uani 1 1 d . . . . .
H27A H 0.654(2) 0.7006(14) 0.1446(12) 0.060(7) Uiso 1 1 d . . . . .
H27B H 0.660(2) 0.6167(13) 0.1024(11) 0.052(6) Uiso 1 1 d . . . . .
H27 H 0.567(2) 0.6879(14) 0.0702(12) 0.063(7) Uiso 1 1 d . . . . .
C28 C 0.26812(13) 0.99776(8) 0.02449(7) 0.0169(3) Uani 1 1 d . . . . .
C29 C 0.21237(15) 1.04019(9) 0.07827(8) 0.0224(3) Uani 1 1 d . . . . .
H29 H 0.1591(18) 1.0108(11) 0.1103(10) 0.037(5) Uiso 1 1 d . . . . .
C30 C 0.23232(16) 1.12256(9) 0.08571(8) 0.0262(3) Uani 1 1 d . . . . .
H30 H 0.1916(19) 1.1510(12) 0.1237(10) 0.043(5) Uiso 1 1 d . . . . .
C31 C 0.30851(15) 1.16363(9) 0.03979(8) 0.0255(3) Uani 1 1 d . . . . .
H31 H 0.3219(18) 1.2217(12) 0.0451(10) 0.039(5) Uiso 1 1 d . . . . .
C32 C 0.36306(15) 1.12268(9) -0.01439(8) 0.0261(3) Uani 1 1 d . . . . .
H32 H 0.4171(18) 1.1522(11) -0.0481(10) 0.039(5) Uiso 1 1 d . . . . .
C33 C 0.34221(14) 1.04010(9) -0.02242(8) 0.0220(3) Uani 1 1 d . . . . .
H33 H 0.3812(17) 1.0112(10) -0.0602(9) 0.027(4) Uiso 1 1 d . . . . .
C34 C -0.03489(18) 0.75804(13) 0.07340(11) 0.0492(5) Uani 1 1 d . . . . .
H34A H -0.0521 0.7559 0.1229 0.074 Uiso 1 1 calc R U . . .
H34B H -0.1185 0.7546 0.0458 0.074 Uiso 1 1 calc R U . . .
H34C H 0.0092 0.8090 0.0632 0.074 Uiso 1 1 calc R U . . .
C36 C 0.4166(2) 0.63836(16) -0.04836(13) 0.0550(6) Uani 1 1 d . . . . .
H36 H 0.496(2) 0.6088(14) -0.0258(11) 0.058(6) Uiso 1 1 d . . . . .
H36A H 0.429(3) 0.7022(19) -0.0545(15) 0.098(10) Uiso 1 1 d . . . . .
C35A C -0.0289(6) 0.6211(4) 0.0618(3) 0.0552(16) Uani 0.59 1 d . . P A 1
H35A H -0.1157 0.6298 0.0384 0.083 Uiso 0.59 1 calc R U P A 1
H35B H -0.0395 0.6089 0.1109 0.083 Uiso 0.59 1 calc R U P A 1
H35C H 0.0149 0.5757 0.0399 0.083 Uiso 0.59 1 calc R U P A 1
C35B C 0.0063(8) 0.6119(5) 0.0842(4) 0.0404(15) Uani 0.41 1 d . . P A 3
H35X H -0.0709 0.5922 0.0567 0.061 Uiso 0.41 1 calc R U P A 3
H35Y H -0.0162 0.6184 0.1327 0.061 Uiso 0.41 1 calc R U P A 3
H35Z H 0.0785 0.5730 0.0817 0.061 Uiso 0.41 1 calc R U P A 3
H36B H 0.399(3) 0.6120(18) -0.0980(16) 0.105(10) Uiso 1 1 d . . . . .
C37A C 0.2854(6) 0.5426(3) 0.0192(3) 0.0644(18) Uani 0.535 1 d . . P B 1
H37A H 0.2512 0.5081 -0.0189 0.097 Uiso 0.535 1 calc R U P B 1
H37B H 0.2230 0.5430 0.0563 0.097 Uiso 0.535 1 calc R U P B 1
H37C H 0.3706 0.5216 0.0374 0.097 Uiso 0.535 1 calc R U P B 1
C37B C 0.2659(6) 0.5436(3) -0.0183(3) 0.0492(12) Uani 0.465 1 d . . P B 3
H37X H 0.2671 0.5312 -0.0679 0.074 Uiso 0.465 1 calc R U P B 3
H37Y H 0.1770 0.5347 -0.0023 0.074 Uiso 0.465 1 calc R U P B 3
H37Z H 0.3284 0.5084 0.0077 0.074 Uiso 0.465 1 calc R U P B 3


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Al1 N4 1.7922(14) . ?
Al1 N3 1.7994(14) . ?
Al1 N2 1.9169(12) . ?
Al1 N1 1.9297(12) . ?
N1 C5 1.3576(16) . ?
N1 C2 1.4045(16) . ?
N2 C18 1.3560(16) . ?
N2 C15 1.3999(16) . ?
N3 C35A 1.413(7) . ?
N3 C34 1.439(2) . ?
N3 C35B 1.496(8) . ?
N4 C37B 1.432(5) . ?
N4 C36 1.455(3) . ?
N4 C37A 1.486(5) . ?
C1 C15 1.4037(18) . ?
C1 C2 1.4060(18) . ?
C1 C28 1.4940(18) . ?
C2 C3 1.4193(18) . ?
C3 C4 1.3790(19) . ?
C3 H3 0.973(16) . ?
C4 C5 1.4109(19) . ?
C4 H4 0.970(16) . ?
C5 C6 1.4908(18) . ?
C6 C7 1.4048(19) . ?
C6 C11 1.4111(19) . ?
C7 C8 1.3969(19) . ?
C7 C12 1.506(2) . ?
C8 C9 1.390(2) . ?
C8 H8 0.994(16) . ?
C9 C10 1.394(2) . ?
C9 C13 1.510(2) . ?
C10 C11 1.393(2) . ?
C10 H10 0.959(17) . ?
C11 C14 1.510(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13B 0.95(3) . ?
C13 H13A 0.96(3) . ?
C13 H13 0.95(3) . ?
C14 H14B 0.97(2) . ?
C14 H14A 0.97(2) . ?
C14 H14 0.96(2) . ?
C15 C16 1.4232(18) . ?
C16 C17 1.3755(19) . ?
C16 H16 0.985(18) . ?
C17 C18 1.4103(19) . ?
C17 H17 0.932(17) . ?
C18 C19 1.4873(18) . ?
C19 C20 1.4041(19) . ?
C19 C24 1.4064(19) . ?
C20 C21 1.3925(19) . ?
C20 C25 1.507(2) . ?
C21 C22 1.393(2) . ?
C21 H21 0.961(17) . ?
C22 C23 1.393(2) . ?
C22 C26 1.510(2) . ?
C23 C24 1.3936(19) . ?
C23 H23 0.957(18) . ?
C24 C27 1.507(2) . ?
C25 H25A 0.97(2) . ?
C25 H25B 0.92(3) . ?
C25 H25 0.95(2) . ?
C26 H26A 0.96(2) . ?
C26 H26B 1.02(2) . ?
C26 H26 0.96(2) . ?
C27 H27A 1.01(2) . ?
C27 H27B 0.96(2) . ?
C27 H27 1.03(2) . ?
C28 C33 1.3956(19) . ?
C28 C29 1.3969(19) . ?
C29 C30 1.386(2) . ?
C29 H29 0.973(19) . ?
C30 C31 1.385(2) . ?
C30 H30 0.980(19) . ?
C31 C32 1.385(2) . ?
C31 H31 0.976(19) . ?
C32 C33 1.392(2) . ?
C32 H32 1.000(19) . ?
C33 H33 0.973(17) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C36 H36 1.02(2) . ?
C36 H36A 1.07(3) . ?
C36 H36B 1.06(3) . ?
C35A H35A 0.9800 . ?
C35A H35B 0.9800 . ?
C35A H35C 0.9800 . ?
C35B H35X 0.9800 . ?
C35B H35Y 0.9800 . ?
C35B H35Z 0.9800 . ?
C37A H37A 0.9800 . ?
C37A H37B 0.9800 . ?
C37A H37C 0.9800 . ?
C37B H37X 0.9800 . ?
C37B H37Y 0.9800 . ?
C37B H37Z 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Al1 N3 119.75(7) . . ?
N4 Al1 N2 112.05(6) . . ?
N3 Al1 N2 107.44(6) . . ?
N4 Al1 N1 111.45(6) . . ?
N3 Al1 N1 109.44(6) . . ?
N2 Al1 N1 93.52(5) . . ?
C5 N1 C2 106.63(11) . . ?
C5 N1 Al1 127.45(9) . . ?
C2 N1 Al1 123.82(9) . . ?
C18 N2 C15 106.82(11) . . ?
C18 N2 Al1 127.34(9) . . ?
C15 N2 Al1 125.76(9) . . ?
C35A N3 C34 106.2(3) . . ?
C34 N3 C35B 114.2(3) . . ?
C35A N3 Al1 132.5(3) . . ?
C34 N3 Al1 120.32(12) . . ?
C35B N3 Al1 124.3(3) . . ?
C37B N4 C36 104.9(3) . . ?
C36 N4 C37A 115.3(3) . . ?
C37B N4 Al1 129.7(3) . . ?
C36 N4 Al1 121.19(13) . . ?
C37A N4 Al1 123.0(3) . . ?
C15 C1 C2 124.94(12) . . ?
C15 C1 C28 116.08(11) . . ?
C2 C1 C28 118.93(11) . . ?
N1 C2 C1 123.69(12) . . ?
N1 C2 C3 108.50(11) . . ?
C1 C2 C3 127.69(12) . . ?
C4 C3 C2 107.26(12) . . ?
C4 C3 H3 126.9(9) . . ?
C2 C3 H3 125.9(9) . . ?
C3 C4 C5 107.11(12) . . ?
C3 C4 H4 128.2(10) . . ?
C5 C4 H4 124.6(9) . . ?
N1 C5 C4 110.46(12) . . ?
N1 C5 C6 122.18(11) . . ?
C4 C5 C6 126.89(12) . . ?
C7 C6 C11 119.87(12) . . ?
C7 C6 C5 122.75(12) . . ?
C11 C6 C5 117.37(12) . . ?
C8 C7 C6 119.01(13) . . ?
C8 C7 C12 119.42(13) . . ?
C6 C7 C12 121.48(12) . . ?
C9 C8 C7 121.88(13) . . ?
C9 C8 H8 119.9(9) . . ?
C7 C8 H8 118.2(9) . . ?
C8 C9 C10 118.17(13) . . ?
C8 C9 C13 121.39(13) . . ?
C10 C9 C13 120.43(14) . . ?
C11 C10 C9 121.90(13) . . ?
C11 C10 H10 117.5(10) . . ?
C9 C10 H10 120.6(10) . . ?
C10 C11 C6 119.00(13) . . ?
C10 C11 C14 119.71(13) . . ?
C6 C11 C14 121.29(13) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13B 112.2(15) . . ?
C9 C13 H13A 114.1(16) . . ?
H13B C13 H13A 103(2) . . ?
C9 C13 H13 114.2(17) . . ?
H13B C13 H13 107(2) . . ?
H13A C13 H13 106(2) . . ?
C11 C14 H14B 111.3(12) . . ?
C11 C14 H14A 114.0(13) . . ?
H14B C14 H14A 106.4(17) . . ?
C11 C14 H14 113.3(13) . . ?
H14B C14 H14 105.0(17) . . ?
H14A C14 H14 106.1(17) . . ?
N2 C15 C1 123.75(12) . . ?
N2 C15 C16 108.36(11) . . ?
C1 C15 C16 127.81(12) . . ?
C17 C16 C15 107.25(12) . . ?
C17 C16 H16 127.0(10) . . ?
C15 C16 H16 125.7(10) . . ?
C16 C17 C18 107.13(12) . . ?
C16 C17 H17 127.1(10) . . ?
C18 C17 H17 125.7(10) . . ?
N2 C18 C17 110.43(12) . . ?
N2 C18 C19 122.75(11) . . ?
C17 C18 C19 126.76(12) . . ?
C20 C19 C24 120.29(12) . . ?
C20 C19 C18 119.26(12) . . ?
C24 C19 C18 120.42(12) . . ?
C21 C20 C19 118.88(12) . . ?
C21 C20 C25 120.14(13) . . ?
C19 C20 C25 120.99(13) . . ?
C20 C21 C22 121.88(13) . . ?
C20 C21 H21 119.0(10) . . ?
C22 C21 H21 119.1(10) . . ?
C21 C22 C23 118.16(13) . . ?
C21 C22 C26 120.76(13) . . ?
C23 C22 C26 121.08(13) . . ?
C22 C23 C24 121.87(13) . . ?
C22 C23 H23 120.7(10) . . ?
C24 C23 H23 117.4(11) . . ?
C23 C24 C19 118.77(12) . . ?
C23 C24 C27 120.49(13) . . ?
C19 C24 C27 120.74(13) . . ?
C20 C25 H25A 112.2(13) . . ?
C20 C25 H25B 113.3(16) . . ?
H25A C25 H25B 102.9(19) . . ?
C20 C25 H25 112.4(13) . . ?
H25A C25 H25 107.3(18) . . ?
H25B C25 H25 108(2) . . ?
C22 C26 H26A 110.1(14) . . ?
C22 C26 H26B 112.0(12) . . ?
H26A C26 H26B 106.4(18) . . ?
C22 C26 H26 113.1(13) . . ?
H26A C26 H26 103.9(18) . . ?
H26B C26 H26 110.8(18) . . ?
C24 C27 H27A 110.4(13) . . ?
C24 C27 H27B 109.9(12) . . ?
H27A C27 H27B 109.5(18) . . ?
C24 C27 H27 110.0(13) . . ?
H27A C27 H27 108.6(17) . . ?
H27B C27 H27 108.4(17) . . ?
C33 C28 C29 118.77(13) . . ?
C33 C28 C1 121.02(12) . . ?
C29 C28 C1 120.12(12) . . ?
C30 C29 C28 120.63(14) . . ?
C30 C29 H29 120.7(11) . . ?
C28 C29 H29 118.7(11) . . ?
C31 C30 C29 120.09(14) . . ?
C31 C30 H30 120.9(11) . . ?
C29 C30 H30 119.0(12) . . ?
C30 C31 C32 120.03(13) . . ?
C30 C31 H31 119.8(11) . . ?
C32 C31 H31 120.2(11) . . ?
C31 C32 C33 120.05(14) . . ?
C31 C32 H32 120.4(11) . . ?
C33 C32 H32 119.6(11) . . ?
C32 C33 C28 120.41(14) . . ?
C32 C33 H33 120.1(10) . . ?
C28 C33 H33 119.4(10) . . ?
N3 C34 H34A 109.5 . . ?
N3 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
N3 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N4 C36 H36 109.4(13) . . ?
N4 C36 H36A 107.6(16) . . ?
H36 C36 H36A 115(2) . . ?
N4 C36 H36B 109.8(17) . . ?
H36 C36 H36B 106(2) . . ?
H36A C36 H36B 109(2) . . ?
N3 C35A H35A 109.5 . . ?
N3 C35A H35B 109.5 . . ?
H35A C35A H35B 109.5 . . ?
N3 C35A H35C 109.5 . . ?
H35A C35A H35C 109.5 . . ?
H35B C35A H35C 109.5 . . ?
N3 C35B H35X 109.5 . . ?
N3 C35B H35Y 109.5 . . ?
H35X C35B H35Y 109.5 . . ?
N3 C35B H35Z 109.5 . . ?
H35X C35B H35Z 109.5 . . ?
H35Y C35B H35Z 109.5 . . ?
N4 C37A H37A 109.5 . . ?
N4 C37A H37B 109.5 . . ?
H37A C37A H37B 109.5 . . ?
N4 C37A H37C 109.5 . . ?
H37A C37A H37C 109.5 . . ?
H37B C37A H37C 109.5 . . ?
N4 C37B H37X 109.5 . . ?
N4 C37B H37Y 109.5 . . ?
H37X C37B H37Y 109.5 . . ?
N4 C37B H37Z 109.5 . . ?
H37X C37B H37Z 109.5 . . ?
H37Y C37B H37Z 109.5 . . ?

_refine_diff_density_max         0.527
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1480579'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H33 N2 , Cl'
_chemical_formula_sum            'C33 H33 Cl N2'
_chemical_formula_weight         493.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   14.4443(6)
_cell_length_b                   18.4741(7)
_cell_length_c                   9.5304(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2543.14(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9444
_cell_measurement_theta_min      4.789
_cell_measurement_theta_max      66.128

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.506
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6625
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'sadabs (Sheldrick, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'ImuS microfocus sealed tube'
_diffrn_measurement_device_type  'Duo with Apex II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36632
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.787
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_full        66.589
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             2263
_reflns_number_gt                2248
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0352P)²+1.4509P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2263
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0769
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
Cl1 Cl 0.94258(3) 0.2500 0.08897(4) 0.02348(14) Uani 1 2 d S T P . .
N1 N 0.92318(8) 0.33815(6) 0.36224(11) 0.0192(2) Uani 1 1 d . . . . .
H1N H 0.9332(11) 0.3108(9) 0.2870(17) 0.030(4) Uiso 1 1 d . . . . .
C1 C 0.83626(12) 0.2500 0.51610(18) 0.0192(4) Uani 1 2 d S T P . .
C2 C 0.86513(9) 0.31911(7) 0.47324(12) 0.0192(3) Uani 1 1 d . . . . .
C3 C 0.84903(9) 0.38373(7) 0.54966(13) 0.0214(3) Uani 1 1 d . . . . .
H3 H 0.8117 0.3881 0.6313 0.026 Uiso 1 1 calc R U . . .
C4 C 0.89650(9) 0.43875(7) 0.48579(13) 0.0216(3) Uani 1 1 d . . . . .
H4 H 0.8986 0.4877 0.5163 0.026 Uiso 1 1 calc R U . . .
C5 C 0.94169(9) 0.41032(7) 0.36709(13) 0.0195(3) Uani 1 1 d . . . . .
C6 C 1.00189(9) 0.44907(7) 0.26726(13) 0.0194(3) Uani 1 1 d . . . . .
C7 C 1.08988(9) 0.42125(7) 0.23133(13) 0.0202(3) Uani 1 1 d . . . . .
C8 C 1.14752(9) 0.46220(7) 0.14610(13) 0.0217(3) Uani 1 1 d . . . . .
H8 H 1.2066 0.4433 0.1218 0.026 Uiso 1 1 calc R U . . .
C9 C 1.12210(9) 0.52997(7) 0.09479(13) 0.0221(3) Uani 1 1 d . . . . .
C10 C 1.03533(9) 0.55661(7) 0.13135(13) 0.0224(3) Uani 1 1 d . . . . .
H10 H 1.0167 0.6026 0.0968 0.027 Uiso 1 1 calc R U . . .
C11 C 0.97516(9) 0.51795(7) 0.21691(13) 0.0213(3) Uani 1 1 d . . . . .
C12 C 1.12562(10) 0.34992(7) 0.28617(15) 0.0257(3) Uani 1 1 d . . . . .
H12B H 1.0957(12) 0.3093(10) 0.2374(18) 0.038(4) Uiso 1 1 d . . . . .
H12C H 1.1923(12) 0.3451(8) 0.2704(17) 0.034(4) Uiso 1 1 d . . . . .
H12A H 1.1149(12) 0.3437(9) 0.3861(19) 0.039(5) Uiso 1 1 d . . . . .
C13 C 1.18645(10) 0.57361(8) 0.00445(16) 0.0275(3) Uani 1 1 d . . . . .
H13A H 1.2293(14) 0.5443(10) -0.049(2) 0.052(5) Uiso 1 1 d . . . . .
H13C H 1.1546(14) 0.6052(11) -0.057(2) 0.054(5) Uiso 1 1 d . . . . .
H13B H 1.2257(14) 0.6033(11) 0.061(2) 0.054(5) Uiso 1 1 d . . . . .
C14 C 0.88338(10) 0.55265(7) 0.25147(16) 0.0280(3) Uani 1 1 d . . . . .
H14A H 0.8645 0.5842 0.1740 0.042 Uiso 1 1 calc R U . . .
H14B H 0.8895 0.5813 0.3375 0.042 Uiso 1 1 calc R U . . .
H14C H 0.8366 0.5149 0.2654 0.042 Uiso 1 1 calc R U . . .
C15 C 0.76507(13) 0.2500 0.63186(18) 0.0195(4) Uani 1 2 d S T P . .
C16 C 0.79048(14) 0.2500 0.77283(19) 0.0238(4) Uani 1 2 d S T P . .
H16 H 0.8551(17) 0.2500 0.801(2) 0.031(6) Uiso 1 2 d S . P . .
C17 C 0.72257(14) 0.2500 0.87655(19) 0.0248(4) Uani 1 2 d S T P . .
H17 H 0.7428(16) 0.2500 0.973(2) 0.030(6) Uiso 1 2 d S . P . .
C18 C 0.62998(14) 0.2500 0.8401(2) 0.0243(4) Uani 1 2 d S T P . .
H18 H 0.5836(17) 0.2500 0.910(2) 0.032(6) Uiso 1 2 d S . P . .
C19 C 0.60432(14) 0.2500 0.6999(2) 0.0256(4) Uani 1 2 d S T P . .
H19 H 0.5396(17) 0.2500 0.673(2) 0.031(6) Uiso 1 2 d S . P . .
C20 C 0.67160(14) 0.2500 0.59602(19) 0.0231(4) Uani 1 2 d S T P . .
H20 H 0.6545(15) 0.2500 0.500(2) 0.026(5) Uiso 1 2 d S . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.3606(16) . ?
N1 C2 1.3949(16) . ?
N1 H1N 0.889(17) . ?
C1 C2 1.4039(14) . ?
C1 C2 1.4039(14) 7_565 ?
C1 C15 1.508(2) . ?
C2 C3 1.4176(18) . ?
C3 C4 1.3688(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.4077(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.4744(18) . ?
C6 C7 1.4131(19) . ?
C6 C11 1.4136(18) . ?
C7 C8 1.3875(18) . ?
C7 C12 1.5087(18) . ?
C8 C9 1.3933(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.3909(19) . ?
C9 C13 1.5018(18) . ?
C10 C11 1.3894(19) . ?
C10 H10 0.9500 . ?
C11 C14 1.5090(19) . ?
C12 H12B 0.983(18) . ?
C12 H12C 0.979(18) . ?
C12 H12A 0.972(18) . ?
C13 H13A 0.97(2) . ?
C13 H13C 0.94(2) . ?
C13 H13B 0.96(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.393(3) . ?
C15 C16 1.393(3) . ?
C16 C17 1.393(3) . ?
C16 H16 0.97(2) . ?
C17 C18 1.382(3) . ?
C17 H17 0.96(2) . ?
C18 C19 1.387(3) . ?
C18 H18 0.95(2) . ?
C19 C20 1.387(3) . ?
C19 H19 0.97(2) . ?
C20 H20 0.95(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
C5 N1 C2 109.84(11) . . ?
C5 N1 H1N 123.6(10) . . ?
C2 N1 H1N 124.5(10) . . ?
C2 C1 C2 130.86(17) . 7_565 ?
C2 C1 C15 114.54(8) . . ?
C2 C1 C15 114.54(8) 7_565 . ?
N1 C2 C1 128.94(12) . . ?
N1 C2 C3 106.01(11) . . ?
C1 C2 C3 124.59(12) . . ?
C4 C3 C2 108.34(11) . . ?
C4 C3 H3 125.8 . . ?
C2 C3 H3 125.8 . . ?
C3 C4 C5 108.22(11) . . ?
C3 C4 H4 125.9 . . ?
C5 C4 H4 125.9 . . ?
N1 C5 C4 107.56(11) . . ?
N1 C5 C6 124.73(11) . . ?
C4 C5 C6 127.66(11) . . ?
C7 C6 C11 119.39(12) . . ?
C7 C6 C5 120.68(11) . . ?
C11 C6 C5 119.67(12) . . ?
C8 C7 C6 118.90(11) . . ?
C8 C7 C12 118.28(12) . . ?
C6 C7 C12 122.79(12) . . ?
C7 C8 C9 122.50(12) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C10 C9 C8 117.87(12) . . ?
C10 C9 C13 120.75(12) . . ?
C8 C9 C13 121.37(12) . . ?
C11 C10 C9 121.92(12) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C6 119.41(12) . . ?
C10 C11 C14 117.34(11) . . ?
C6 C11 C14 123.25(12) . . ?
C7 C12 H12B 110.7(10) . . ?
C7 C12 H12C 111.3(9) . . ?
H12B C12 H12C 106.9(14) . . ?
C7 C12 H12A 112.9(10) . . ?
H12B C12 H12A 107.6(14) . . ?
H12C C12 H12A 107.2(14) . . ?
C9 C13 H13A 113.5(11) . . ?
C9 C13 H13C 112.5(12) . . ?
H13A C13 H13C 109.3(16) . . ?
C9 C13 H13B 110.7(11) . . ?
H13A C13 H13B 103.9(16) . . ?
H13C C13 H13B 106.3(16) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 119.48(17) . . ?
C20 C15 C1 118.79(16) . . ?
C16 C15 C1 121.73(17) . . ?
C17 C16 C15 119.94(18) . . ?
C17 C16 H16 118.6(13) . . ?
C15 C16 H16 121.5(13) . . ?
C18 C17 C16 120.24(18) . . ?
C18 C17 H17 122.2(14) . . ?
C16 C17 H17 117.5(14) . . ?
C17 C18 C19 120.04(18) . . ?
C17 C18 H18 120.6(14) . . ?
C19 C18 H18 119.4(14) . . ?
C18 C19 C20 120.04(19) . . ?
C18 C19 H19 120.6(14) . . ?
C20 C19 H19 119.3(14) . . ?
C19 C20 C15 120.27(17) . . ?
C19 C20 H20 120.4(14) . . ?
C15 C20 H20 119.3(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
N1 H1N Cl1 0.889(17) 2.200(17) 3.0844(11) 172.6(15) .
C12 H12B Cl1 0.983(18) 2.844(19) 3.7323(15) 150.6(13) .
C16 H16 Cl1 0.97(2) 3.02(2) 3.7289(19) 131.0(16) 1_556
C19 H19 Cl1 0.97(2) 2.87(2) 3.611(2) 134.4(17) 4_455
C13 H13C Cl1 0.94(2) 3.04(2) 3.8581(15) 146.4(15) 3_755

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1480580'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H33 N2 , I'
_chemical_formula_sum            'C33 H33 I N2'
_chemical_formula_weight         584.51

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   14.4600(19)
_cell_length_b                   18.427(2)
_cell_length_c                   10.2026(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2718.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9125
_cell_measurement_theta_min      2.211
_cell_measurement_theta_max      26.689

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    1.202
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6466
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'sadabs (Sheldrick, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Duo with Apex II CCD'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31835
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.210
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_full        26.000
_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             3211
_reflns_number_gt                2649
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²+4.6840P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3211
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0866
_refine_ls_wR_factor_gt          0.0807
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.1588(3) 0.2500 0.4731(4) 0.0165(7) Uani 1 2 d S T P . .
I1 I 0.05541(2) 0.2500 0.91381(2) 0.02445(10) Uani 1 2 d S T P . .
N1 N 0.07219(16) 0.33737(13) 0.6181(2) 0.0172(5) Uani 1 1 d . . . . .
H1 H 0.062(2) 0.3143(19) 0.672(4) 0.021 Uiso 1 1 d . U . . .
C2 C 0.13029(18) 0.31929(15) 0.5142(3) 0.0169(5) Uani 1 1 d . . . . .
C3 C 0.14846(19) 0.38534(15) 0.4477(3) 0.0196(6) Uani 1 1 d . . . . .
H3 H 0.182(2) 0.3866(19) 0.380(3) 0.029(9) Uiso 1 1 d . . . . .
C4 C 0.1026(2) 0.44007(15) 0.5108(3) 0.0203(6) Uani 1 1 d . . . . .
H4 H 0.103(2) 0.4847(17) 0.488(3) 0.014(7) Uiso 1 1 d . . . . .
C5 C 0.05556(18) 0.41010(14) 0.6192(3) 0.0175(5) Uani 1 1 d . . . . .
C6 C -0.00373(18) 0.44648(14) 0.7170(3) 0.0163(5) Uani 1 1 d . . . . .
C7 C 0.02519(19) 0.51276(14) 0.7737(3) 0.0186(5) Uani 1 1 d . . . . .
C8 C -0.03278(19) 0.54810(15) 0.8603(3) 0.0217(6) Uani 1 1 d . . . . .
H8 H -0.0126 0.5922 0.8990 0.026 Uiso 1 1 calc R U . . .
C9 C -0.1198(2) 0.52121(15) 0.8927(3) 0.0206(6) Uani 1 1 d . . . . .
C10 C -0.14741(19) 0.45631(15) 0.8354(3) 0.0195(6) Uani 1 1 d . . . . .
H10 H -0.202(2) 0.4389(18) 0.851(3) 0.027(9) Uiso 1 1 d . . . . .
C11 C -0.09208(18) 0.41870(14) 0.7475(3) 0.0180(5) Uani 1 1 d . . . . .
C12 C 0.1176(2) 0.54724(18) 0.7448(4) 0.0291(7) Uani 1 1 d . . . . .
H121 H 0.161(2) 0.5138(18) 0.735(3) 0.023(8) Uiso 1 1 d . . . . .
H122 H 0.112(2) 0.5753(19) 0.671(4) 0.028(9) Uiso 1 1 d . . . . .
H123 H 0.134(2) 0.575(2) 0.819(4) 0.034(10) Uiso 1 1 d . . . . .
C13 C -0.1818(2) 0.56210(19) 0.9860(3) 0.0274(7) Uani 1 1 d . . . . .
H131 H -0.148(3) 0.586(2) 1.052(4) 0.040(10) Uiso 1 1 d . . . . .
H132 H -0.220(3) 0.533(2) 1.026(4) 0.035(10) Uiso 1 1 d . . . . .
H133 H -0.212(3) 0.595(2) 0.948(4) 0.048(12) Uiso 1 1 d . . . . .
C14 C -0.1312(2) 0.35092(17) 0.6850(4) 0.0254(6) Uani 1 1 d . . . . .
H141 H -0.121(3) 0.349(2) 0.600(4) 0.032(10) Uiso 1 1 d . . . . .
H142 H -0.111(2) 0.312(2) 0.728(3) 0.030(9) Uiso 1 1 d . . . . .
H143 H -0.197(3) 0.351(2) 0.696(4) 0.043(11) Uiso 1 1 d . . . . .
C15 C 0.2293(3) 0.2500 0.3643(4) 0.0166(7) Uani 1 2 d S T P . .
C16 C 0.2043(3) 0.2500 0.2332(4) 0.0259(9) Uani 1 2 d S T P . .
H16 H 0.144(4) 0.2500 0.214(5) 0.032(14) Uiso 1 2 d S . P . .
C17 C 0.2711(3) 0.2500 0.1355(4) 0.0264(9) Uani 1 2 d S T P . .
H17 H 0.2532 0.2500 0.0459 0.032 Uiso 1 2 calc R U P . .
C18 C 0.3636(3) 0.2500 0.1689(4) 0.0248(9) Uani 1 2 d S T P . .
H18 H 0.4095 0.2500 0.1023 0.030 Uiso 1 2 calc R U P . .
C19 C 0.3891(3) 0.2500 0.2977(5) 0.0285(10) Uani 1 2 d S T P . .
H19 H 0.449(3) 0.2500 0.316(5) 0.032(14) Uiso 1 2 d S . P . .
C20 C 0.3229(3) 0.2500 0.3966(4) 0.0256(9) Uani 1 2 d S T P . .
H20 H 0.336(3) 0.2500 0.481(5) 0.022(12) Uiso 1 2 d S . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.406(3) . ?
C1 C2 1.406(3) 7_565 ?
C1 C15 1.507(5) . ?
N1 C5 1.362(3) . ?
N1 C2 1.393(3) . ?
N1 H1 0.71(4) . ?
C2 C3 1.418(4) . ?
C3 C4 1.368(4) . ?
C3 H3 0.85(4) . ?
C4 C5 1.411(4) . ?
C4 H4 0.85(3) . ?
C5 C6 1.476(4) . ?
C6 C11 1.411(4) . ?
C6 C7 1.414(4) . ?
C7 C8 1.381(4) . ?
C7 C12 1.508(4) . ?
C8 C9 1.392(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(4) . ?
C9 C13 1.509(4) . ?
C10 C11 1.387(4) . ?
C10 H10 0.87(3) . ?
C11 C14 1.512(4) . ?
C12 H121 0.89(3) . ?
C12 H122 0.92(4) . ?
C12 H123 0.94(4) . ?
C13 H131 0.94(4) . ?
C13 H132 0.88(4) . ?
C13 H133 0.85(4) . ?
C14 H141 0.88(4) . ?
C14 H142 0.88(4) . ?
C14 H143 0.96(4) . ?
C15 C16 1.386(6) . ?
C15 C20 1.392(6) . ?
C16 C17 1.388(6) . ?
C16 H16 0.89(5) . ?
C17 C18 1.380(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.364(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.391(6) . ?
C19 H19 0.88(5) . ?
C20 H20 0.88(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C2 130.6(3) . 7_565 ?
C2 C1 C15 114.71(17) . . ?
C2 C1 C15 114.71(17) 7_565 . ?
C5 N1 C2 110.4(2) . . ?
C5 N1 H1 123(3) . . ?
C2 N1 H1 125(3) . . ?
N1 C2 C1 128.4(3) . . ?
N1 C2 C3 105.7(2) . . ?
C1 C2 C3 125.7(3) . . ?
C4 C3 C2 108.5(2) . . ?
C4 C3 H3 130(2) . . ?
C2 C3 H3 121(2) . . ?
C3 C4 C5 108.3(2) . . ?
C3 C4 H4 126(2) . . ?
C5 C4 H4 126(2) . . ?
N1 C5 C4 107.1(2) . . ?
N1 C5 C6 123.7(2) . . ?
C4 C5 C6 129.2(2) . . ?
C11 C6 C7 119.4(2) . . ?
C11 C6 C5 120.7(2) . . ?
C7 C6 C5 119.8(2) . . ?
C8 C7 C6 119.3(2) . . ?
C8 C7 C12 117.6(3) . . ?
C6 C7 C12 123.1(3) . . ?
C7 C8 C9 122.2(3) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C10 C9 C8 117.8(3) . . ?
C10 C9 C13 121.6(3) . . ?
C8 C9 C13 120.6(3) . . ?
C11 C10 C9 122.4(3) . . ?
C11 C10 H10 118(2) . . ?
C9 C10 H10 120(2) . . ?
C10 C11 C6 118.9(2) . . ?
C10 C11 C14 118.0(3) . . ?
C6 C11 C14 123.0(3) . . ?
C7 C12 H121 111(2) . . ?
C7 C12 H122 109(2) . . ?
H121 C12 H122 111(3) . . ?
C7 C12 H123 107(2) . . ?
H121 C12 H123 107(3) . . ?
H122 C12 H123 112(3) . . ?
C9 C13 H131 112(2) . . ?
C9 C13 H132 111(2) . . ?
H131 C13 H132 106(3) . . ?
C9 C13 H133 112(3) . . ?
H131 C13 H133 105(3) . . ?
H132 C13 H133 110(4) . . ?
C11 C14 H141 113(2) . . ?
C11 C14 H142 110(2) . . ?
H141 C14 H142 113(3) . . ?
C11 C14 H143 109(2) . . ?
H141 C14 H143 106(3) . . ?
H142 C14 H143 105(3) . . ?
C16 C15 C20 118.8(4) . . ?
C16 C15 C1 122.3(4) . . ?
C20 C15 C1 118.9(3) . . ?
C15 C16 C17 120.8(4) . . ?
C15 C16 H16 118(3) . . ?
C17 C16 H16 122(3) . . ?
C18 C17 C16 119.8(4) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.8(4) . . ?
C18 C19 H19 118(3) . . ?
C20 C19 H19 121(3) . . ?
C19 C20 C15 119.8(4) . . ?
C19 C20 H20 124(3) . . ?
C15 C20 H20 116(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
N1 H1 I1 0.71(4) 2.74(4) 3.428(2) 165(3) .
C14 H142 I1 0.88(4) 3.28(4) 4.024(3) 144(3) .
C19 H19 I1 0.88(5) 3.16(5) 3.801(5) 131(4) 4_556
C16 H16 I1 0.89(5) 3.33(5) 3.906(4) 125(4) 1_554
C17 H17 I1 0.95 3.16 3.853(5) 131.0 1_554
C13 H131 I1 0.94(4) 3.33(4) 4.046(3) 135(3) 3_557

_refine_diff_density_max         0.573
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.091

