# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_6MACdippHCl
_database_code_depnum_ccdc_archive 'CCDC 1024535'
_audit_update_record             
;
2016-01-29 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            6MACdippHCl
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H32 Cl N O'
_chemical_formula_sum            'C21 H32 Cl N O'
_chemical_formula_weight         349.92

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.6015(19)
_cell_length_b                   12.822(2)
_cell_length_c                   13.428(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1997.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3165
_cell_measurement_theta_min      1.7511
_cell_measurement_theta_max      31.7837

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.199
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6956
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku SCX-Mini with Mercury 2+ CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17572
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.034
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             3505
_reflns_number_gt                3277
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.968

_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0692P)²+0.4563P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1338 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3505
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 0.13162(6) 0.46530(6) 0.72264(6) 0.0289(2) Uani 1 1 d . . . . .
O1 O 0.44484(19) 0.24609(16) 0.77169(18) 0.0275(5) Uani 1 1 d . . . . .
N1 N 0.3128(2) 0.33786(18) 0.68630(17) 0.0152(5) Uani 1 1 d . . . . .
C2 C 0.4059(3) 0.3318(2) 0.7501(2) 0.0184(6) Uani 1 1 d . . . . .
C19 C 0.1684(3) 0.2301(2) 0.8361(2) 0.0209(7) Uani 1 1 d . . . . .
H19 H 0.2072 0.2977 0.8422 0.025 Uiso 1 1 calc R U . . .
C10 C 0.2559(3) 0.2410(2) 0.6600(2) 0.0173(6) Uani 1 1 d . . . . .
C14 C 0.2176(3) 0.1061(2) 0.5404(2) 0.0246(7) Uani 1 1 d . . . . .
H14 H 0.2269 0.0777 0.4771 0.030 Uiso 1 1 calc R U . . .
C1 C 0.2638(2) 0.4345(2) 0.6513(2) 0.0181(6) Uani 1 1 d . . . . .
H1 H 0.2414 0.4245 0.5816 0.022 Uiso 1 1 calc R U . . .
C15 C 0.2736(3) 0.1991(2) 0.5638(2) 0.0201(6) Uani 1 1 d . . . . .
C12 C 0.1329(3) 0.0968(2) 0.7022(2) 0.0230(7) Uani 1 1 d . . . . .
H12 H 0.0863 0.0621 0.7478 0.028 Uiso 1 1 calc R U . . .
C16 C 0.3545(3) 0.2503(2) 0.4890(2) 0.0240(7) Uani 1 1 d . . . . .
H16 H 0.3620 0.3240 0.5072 0.029 Uiso 1 1 calc R U . . .
C11 C 0.1863(2) 0.1908(2) 0.7299(2) 0.0178(6) Uani 1 1 d . . . . .
C13 C 0.1489(3) 0.0552(2) 0.6082(2) 0.0237(7) Uani 1 1 d . . . . .
H13 H 0.1132 -0.0072 0.5909 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3485(3) 0.5270(2) 0.6551(2) 0.0208(7) Uani 1 1 d . . . . .
C20 C 0.0407(3) 0.2463(3) 0.8602(3) 0.0273(7) Uani 1 1 d . . . . .
H20A H 0.0077 0.2939 0.8130 0.041 Uiso 1 1 calc R U . . .
H20B H 0.0333 0.2745 0.9261 0.041 Uiso 1 1 calc R U . . .
H20C H 0.0011 0.1807 0.8566 0.041 Uiso 1 1 calc R U . . .
C8 C 0.2888(3) 0.6300(2) 0.6310(2) 0.0263(7) Uani 1 1 d . . . . .
H8A H 0.2491 0.6240 0.5686 0.039 Uiso 1 1 calc R U . . .
H8B H 0.3453 0.6845 0.6267 0.039 Uiso 1 1 calc R U . . .
H8C H 0.2345 0.6463 0.6827 0.039 Uiso 1 1 calc R U . . .
C4 C 0.3975(3) 0.5314(2) 0.7610(2) 0.0214(6) Uani 1 1 d . . . . .
H4A H 0.3354 0.5483 0.8066 0.026 Uiso 1 1 calc R U . . .
H4B H 0.4534 0.5876 0.7643 0.026 Uiso 1 1 calc R U . . .
C3 C 0.4556(3) 0.4305(2) 0.7968(2) 0.0227(7) Uani 1 1 d . . . . .
C9 C 0.4418(3) 0.5089(3) 0.5757(2) 0.0261(7) Uani 1 1 d . . . . .
H9A H 0.4778 0.4424 0.5867 0.039 Uiso 1 1 calc R U . . .
H9B H 0.4988 0.5630 0.5801 0.039 Uiso 1 1 calc R U . . .
H9C H 0.4073 0.5099 0.5108 0.039 Uiso 1 1 calc R U . . .
C21 C 0.2239(3) 0.1550(3) 0.9111(2) 0.0296(8) Uani 1 1 d . . . . .
H21A H 0.1836 0.0896 0.9101 0.044 Uiso 1 1 calc R U . . .
H21B H 0.2198 0.1845 0.9767 0.044 Uiso 1 1 calc R U . . .
H21C H 0.3032 0.1439 0.8935 0.044 Uiso 1 1 calc R U . . .
C6 C 0.4344(4) 0.4188(3) 0.9099(3) 0.0422(10) Uani 1 1 d . . . . .
H6A H 0.3531 0.4138 0.9223 0.063 Uiso 1 1 calc R U . . .
H6B H 0.4650 0.4784 0.9440 0.063 Uiso 1 1 calc R U . . .
H6C H 0.4720 0.3568 0.9335 0.063 Uiso 1 1 calc R U . . .
C7 C 0.5868(3) 0.4332(3) 0.7780(3) 0.0415(10) Uani 1 1 d . . . . .
H7A H 0.6212 0.3705 0.8033 0.062 Uiso 1 1 calc R U . . .
H7B H 0.6197 0.4924 0.8112 0.062 Uiso 1 1 calc R U . . .
H7C H 0.6012 0.4383 0.7078 0.062 Uiso 1 1 calc R U . . .
C17 C 0.3091(4) 0.2449(4) 0.3811(3) 0.0542(13) Uani 1 1 d . . . . .
H17A H 0.3506 0.2937 0.3405 0.081 Uiso 1 1 calc R U . . .
H17B H 0.2285 0.2620 0.3803 0.081 Uiso 1 1 calc R U . . .
H17C H 0.3198 0.1757 0.3555 0.081 Uiso 1 1 calc R U . . .
C18 C 0.4726(3) 0.2016(4) 0.4943(3) 0.0478(11) Uani 1 1 d . . . . .
H18A H 0.4694 0.1320 0.4679 0.072 Uiso 1 1 calc R U . . .
H18B H 0.4977 0.1992 0.5624 0.072 Uiso 1 1 calc R U . . .
H18C H 0.5258 0.2424 0.4559 0.072 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
Cl1 C1 1.850(3) . ?
O1 C2 1.223(4) . ?
N1 C2 1.381(4) . ?
N1 C1 1.442(4) . ?
N1 C10 1.450(4) . ?
C2 C3 1.526(4) . ?
C19 C11 1.527(4) . ?
C19 C20 1.530(4) . ?
C19 C21 1.536(4) . ?
C19 H19 0.9800 . ?
C10 C11 1.395(4) . ?
C10 C15 1.415(4) . ?
C14 C13 1.376(5) . ?
C14 C15 1.394(4) . ?
C14 H14 0.9300 . ?
C1 C5 1.540(4) . ?
C1 H1 0.9800 . ?
C15 C16 1.523(4) . ?
C12 C13 1.383(4) . ?
C12 C11 1.405(4) . ?
C12 H12 0.9300 . ?
C16 C18 1.508(5) . ?
C16 C17 1.543(5) . ?
C16 H16 0.9800 . ?
C13 H13 0.9300 . ?
C5 C8 1.526(4) . ?
C5 C4 1.534(4) . ?
C5 C9 1.537(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C4 C3 1.536(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 C7 1.543(5) . ?
C3 C6 1.545(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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 N1 C1 124.0(2) . . ?
C2 N1 C10 117.3(2) . . ?
C1 N1 C10 118.5(2) . . ?
O1 C2 N1 119.1(3) . . ?
O1 C2 C3 120.5(3) . . ?
N1 C2 C3 120.3(2) . . ?
C11 C19 C20 112.0(3) . . ?
C11 C19 C21 110.4(3) . . ?
C20 C19 C21 110.7(3) . . ?
C11 C19 H19 107.9 . . ?
C20 C19 H19 107.9 . . ?
C21 C19 H19 107.9 . . ?
C11 C10 C15 121.5(3) . . ?
C11 C10 N1 119.7(3) . . ?
C15 C10 N1 118.8(3) . . ?
C13 C14 C15 121.8(3) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
N1 C1 C5 113.6(2) . . ?
N1 C1 Cl1 109.95(19) . . ?
C5 C1 Cl1 110.36(19) . . ?
N1 C1 H1 107.6 . . ?
C5 C1 H1 107.6 . . ?
Cl1 C1 H1 107.6 . . ?
C14 C15 C10 117.6(3) . . ?
C14 C15 C16 120.5(3) . . ?
C10 C15 C16 121.9(3) . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C18 C16 C15 110.5(3) . . ?
C18 C16 C17 109.6(3) . . ?
C15 C16 C17 112.9(3) . . ?
C18 C16 H16 107.9 . . ?
C15 C16 H16 107.9 . . ?
C17 C16 H16 107.9 . . ?
C10 C11 C12 118.2(3) . . ?
C10 C11 C19 123.7(3) . . ?
C12 C11 C19 118.1(3) . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C8 C5 C4 109.4(2) . . ?
C8 C5 C9 107.7(3) . . ?
C4 C5 C9 112.8(3) . . ?
C8 C5 C1 111.7(2) . . ?
C4 C5 C1 107.2(2) . . ?
C9 C5 C1 108.1(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C4 C3 115.0(2) . . ?
C5 C4 H4A 108.5 . . ?
C3 C4 H4A 108.5 . . ?
C5 C4 H4B 108.5 . . ?
C3 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
C2 C3 C4 113.8(2) . . ?
C2 C3 C7 108.9(3) . . ?
C4 C3 C7 111.3(3) . . ?
C2 C3 C6 105.3(3) . . ?
C4 C3 C6 108.6(3) . . ?
C7 C3 C6 108.7(3) . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_refine_diff_density_max         0.343
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044

_shelxl_version_number           2014-3

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

data_6MACdippCHinsertion
_database_code_depnum_ccdc_archive 'CCDC 1024536'
_audit_update_record             
;
2016-01-29 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            6MACdippCHinsertion
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H31 N O'
_chemical_formula_sum            'C21 H31 N O'
_chemical_formula_weight         313.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.9044(5)
_cell_length_b                   11.5431(6)
_cell_length_c                   17.7710(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.232(3)
_cell_angle_gamma                90
_cell_volume                     1825.20(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS. Apex II release 2010. Bruker AXS, Inc.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Nonius Kappa CCD with Bruker AXS Apex II detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            70507
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.294
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             3217
_reflns_number_gt                2816
_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       'Collect Software (Nonius B. V., 1998)'
_computing_cell_refinement       'Collect Software (Nonius B. V., 1998)'
_computing_data_reduction        
'DENZO and Scalepack (Otwinski and Minor, 1997)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0518P)²+1.2408P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3217
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
O1 O 0.75475(12) 0.78505(9) 0.24483(6) 0.0234(3) Uani 1 1 d . . . . .
N1 N 0.80414(12) 0.91363(9) 0.15269(6) 0.0130(3) Uani 1 1 d . . . . .
C2 C 0.74844(15) 0.88455(12) 0.22142(8) 0.0151(3) Uani 1 1 d . . . . .
C3 C 0.66925(15) 0.97817(12) 0.26583(8) 0.0176(3) Uani 1 1 d . . . . .
C10 C 0.91081(15) 0.83699(12) 0.11968(7) 0.0137(3) Uani 1 1 d . . . . .
C5 C 0.76327(16) 1.12812(12) 0.16794(8) 0.0184(3) Uani 1 1 d . . . . .
C15 C 1.04649(15) 0.89571(12) 0.11466(7) 0.0161(3) Uani 1 1 d . . . . .
C11 C 0.88643(15) 0.72519(12) 0.09185(7) 0.0155(3) Uani 1 1 d . . . . .
C4 C 0.72922(16) 1.09998(12) 0.24978(8) 0.0188(3) Uani 1 1 d . . . . .
H4A H 0.6563 1.1558 0.2665 0.023 Uiso 1 1 calc R U . . .
H4B H 0.8207 1.1113 0.2803 0.023 Uiso 1 1 calc R U . . .
C1 C 0.85859(15) 1.03224(11) 0.13345(7) 0.0140(3) Uani 1 1 d . . . . .
H1 H 0.8407 1.0395 0.0789 0.017 Uiso 1 1 calc R U . . .
C19 C 0.73276(16) 0.66779(12) 0.09099(8) 0.0191(3) Uani 1 1 d . . . . .
H19 H 0.6961 0.6719 0.1422 0.023 Uiso 1 1 calc R U . . .
C12 C 1.01198(16) 0.67270(12) 0.06126(8) 0.0190(3) Uani 1 1 d . . . . .
H12 H 1.0028 0.5976 0.0426 0.023 Uiso 1 1 calc R U . . .
C16 C 1.03299(15) 1.01877(12) 0.14519(8) 0.0164(3) Uani 1 1 d . . . . .
C13 C 1.14947(16) 0.72827(13) 0.05769(8) 0.0213(3) Uani 1 1 d . . . . .
H13 H 1.2302 0.6897 0.0375 0.026 Uiso 1 1 calc R U . . .
C8 C 0.69662(19) 0.95244(14) 0.34985(8) 0.0257(4) Uani 1 1 d . . . . .
H8A H 0.6558 0.8778 0.3613 0.039 Uiso 1 1 calc R U . . .
H8B H 0.6485 1.0107 0.3790 0.039 Uiso 1 1 calc R U . . .
H8C H 0.8027 0.9527 0.3618 0.039 Uiso 1 1 calc R U . . .
C14 C 1.16828(16) 0.84069(13) 0.08388(8) 0.0198(3) Uani 1 1 d . . . . .
H14 H 1.2602 0.8783 0.0809 0.024 Uiso 1 1 calc R U . . .
C17 C 1.08665(16) 1.01994(13) 0.22822(8) 0.0193(3) Uani 1 1 d . . . . .
H17A H 1.0251 0.9688 0.2564 0.029 Uiso 1 1 calc R U . . .
H17B H 1.0791 1.0972 0.2478 0.029 Uiso 1 1 calc R U . . .
H17C H 1.1893 0.9946 0.2325 0.029 Uiso 1 1 calc R U . . .
C6 C 0.61885(17) 1.13957(14) 0.11792(9) 0.0260(4) Uani 1 1 d . . . . .
H6A H 0.5786 1.0639 0.1072 0.039 Uiso 1 1 calc R U . . .
H6B H 0.6417 1.1773 0.0716 0.039 Uiso 1 1 calc R U . . .
H6C H 0.5462 1.1846 0.1437 0.039 Uiso 1 1 calc R U . . .
C9 C 0.49947(17) 0.96573(14) 0.24761(10) 0.0278(4) Uani 1 1 d . . . . .
H9A H 0.4803 0.9743 0.1944 0.042 Uiso 1 1 calc R U . . .
H9B H 0.4460 1.0245 0.2739 0.042 Uiso 1 1 calc R U . . .
H9C H 0.4664 0.8907 0.2632 0.042 Uiso 1 1 calc R U . . .
C20 C 0.73513(19) 0.54032(13) 0.06815(9) 0.0263(4) Uani 1 1 d . . . . .
H20A H 0.7650 0.5339 0.0170 0.039 Uiso 1 1 calc R U . . .
H20B H 0.6366 0.5078 0.0725 0.039 Uiso 1 1 calc R U . . .
H20C H 0.8053 0.4991 0.1006 0.039 Uiso 1 1 calc R U . . .
C7 C 0.84397(19) 1.24562(13) 0.16651(9) 0.0257(4) Uani 1 1 d . . . . .
H7A H 0.7775 1.3052 0.1829 0.039 Uiso 1 1 calc R U . . .
H7B H 0.8731 1.2621 0.1162 0.039 Uiso 1 1 calc R U . . .
H7C H 0.9318 1.2431 0.1996 0.039 Uiso 1 1 calc R U . . .
C18 C 1.12352(17) 1.10509(13) 0.09964(9) 0.0223(3) Uani 1 1 d . . . . .
H18A H 1.2256 1.0789 0.0976 0.033 Uiso 1 1 calc R U . . .
H18B H 1.1214 1.1798 0.1233 0.033 Uiso 1 1 calc R U . . .
H18C H 1.0802 1.1106 0.0494 0.033 Uiso 1 1 calc R U . . .
C21 C 0.62148(18) 0.73423(14) 0.03922(10) 0.0298(4) Uani 1 1 d . . . . .
H21A H 0.6152 0.8131 0.0559 0.045 Uiso 1 1 calc R U . . .
H21B H 0.5242 0.6987 0.0407 0.045 Uiso 1 1 calc R U . . .
H21C H 0.6553 0.7326 -0.0114 0.045 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
O1 C2 1.2222(17) . ?
N1 C2 1.3775(18) . ?
N1 C10 1.4396(17) . ?
N1 C1 1.4964(17) . ?
C2 C3 1.5268(19) . ?
C3 C8 1.533(2) . ?
C3 C4 1.535(2) . ?
C3 C9 1.540(2) . ?
C10 C15 1.3911(19) . ?
C10 C11 1.3960(19) . ?
C5 C4 1.532(2) . ?
C5 C7 1.536(2) . ?
C5 C1 1.5367(19) . ?
C5 C6 1.540(2) . ?
C15 C14 1.387(2) . ?
C15 C16 1.5269(19) . ?
C11 C12 1.400(2) . ?
C11 C19 1.5199(19) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C1 C16 1.5666(19) . ?
C1 H1 0.9800 . ?
C19 C20 1.527(2) . ?
C19 C21 1.531(2) . ?
C19 H19 0.9800 . ?
C12 C13 1.386(2) . ?
C12 H12 0.9300 . ?
C16 C18 1.5325(19) . ?
C16 C17 1.5333(19) . ?
C13 C14 1.386(2) . ?
C13 H13 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C14 H14 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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 N1 C10 118.53(11) . . ?
C2 N1 C1 123.82(11) . . ?
C10 N1 C1 104.14(10) . . ?
O1 C2 N1 121.16(12) . . ?
O1 C2 C3 120.35(12) . . ?
N1 C2 C3 118.38(12) . . ?
C2 C3 C8 107.90(12) . . ?
C2 C3 C4 112.42(11) . . ?
C8 C3 C4 108.38(12) . . ?
C2 C3 C9 107.13(11) . . ?
C8 C3 C9 107.72(12) . . ?
C4 C3 C9 113.08(12) . . ?
C15 C10 C11 123.45(12) . . ?
C15 C10 N1 108.37(12) . . ?
C11 C10 N1 128.06(12) . . ?
C4 C5 C7 108.24(12) . . ?
C4 C5 C1 111.02(11) . . ?
C7 C5 C1 111.32(12) . . ?
C4 C5 C6 111.99(12) . . ?
C7 C5 C6 107.19(12) . . ?
C1 C5 C6 107.06(11) . . ?
C14 C15 C10 119.75(13) . . ?
C14 C15 C16 129.75(13) . . ?
C10 C15 C16 110.48(12) . . ?
C10 C11 C12 114.97(13) . . ?
C10 C11 C19 122.29(12) . . ?
C12 C11 C19 122.66(13) . . ?
C5 C4 C3 116.99(12) . . ?
C5 C4 H4A 108.1 . . ?
C3 C4 H4A 108.1 . . ?
C5 C4 H4B 108.1 . . ?
C3 C4 H4B 108.1 . . ?
H4A C4 H4B 107.3 . . ?
N1 C1 C5 112.27(11) . . ?
N1 C1 C16 101.95(10) . . ?
C5 C1 C16 125.34(11) . . ?
N1 C1 H1 105.2 . . ?
C5 C1 H1 105.2 . . ?
C16 C1 H1 105.2 . . ?
C11 C19 C20 113.65(12) . . ?
C11 C19 C21 110.42(12) . . ?
C20 C19 C21 109.77(12) . . ?
C11 C19 H19 107.6 . . ?
C20 C19 H19 107.6 . . ?
C21 C19 H19 107.6 . . ?
C13 C12 C11 122.53(13) . . ?
C13 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
C15 C16 C18 111.53(11) . . ?
C15 C16 C17 108.92(11) . . ?
C18 C16 C17 110.61(11) . . ?
C15 C16 C1 97.84(10) . . ?
C18 C16 C1 113.85(11) . . ?
C17 C16 C1 113.41(11) . . ?
C12 C13 C14 120.88(13) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 C14 C15 118.34(13) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.052

_shelxl_version_number           2014-3

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

data_6MACdippCyclopropeneAdduct
_database_code_depnum_ccdc_archive 'CCDC 1024537'
_audit_update_record             
;
2016-01-29 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            6MACdippCyclopropeneAdduct
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H41 N O'
_chemical_formula_sum            'C31 H41 N O'
_chemical_formula_weight         443.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   8.6897(5)
_cell_length_b                   29.0766(18)
_cell_length_c                   10.8005(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.809(3)
_cell_angle_gamma                90
_cell_volume                     2612.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.066
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS.Apex II release 2010. Bruker AXS, Inc.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Nonius Kappa CCD with Bruker AXS Apex II detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            141864
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.401
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             4602
_reflns_number_gt                3896
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'Collect Software (Nonius B. V., 1998)'
_computing_cell_refinement       'Collect Software (Nonius B. V., 1998)'
_computing_data_reduction        
'DENZO and Scalepack (Otwinski and Minor, 1997)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0816P)²+1.5944P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4602
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1394
_refine_ls_wR_factor_gt          0.1186
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 -0.38156(18) 0.12889(5) 0.75070(15) 0.0161(3) Uani 1 1 d . . . . .
C5 C -0.4472(2) 0.15840(6) 0.84186(16) 0.0201(4) Uani 1 1 d . . . . .
C4 C -0.3549(2) 0.14350(6) 0.97985(17) 0.0217(4) Uani 1 1 d . . . . .
H4A H -0.3801 0.1115 0.9909 0.026 Uiso 1 1 calc R U . . .
H4B H -0.3935 0.1615 1.0404 0.026 Uiso 1 1 calc R U . . .
C3 C -0.1710(2) 0.14861(6) 1.01535(16) 0.0208(4) Uani 1 1 d . . . . .
C2 C -0.1042(2) 0.14582(5) 0.89835(16) 0.0177(4) Uani 1 1 d . . . . .
C24 C -0.47592(19) 0.11707(6) 0.61508(16) 0.0182(4) Uani 1 1 d . . . . .
C6 C -0.6258(2) 0.14854(7) 0.8207(2) 0.0305(4) Uani 1 1 d . . . . .
H6A H -0.6853 0.1575 0.7347 0.046 Uiso 1 1 calc R U . . .
H6B H -0.6634 0.1657 0.8823 0.046 Uiso 1 1 calc R U . . .
H6C H -0.6408 0.1163 0.8320 0.046 Uiso 1 1 calc R U . . .
C7 C -0.4262(2) 0.20995(6) 0.82076(18) 0.0261(4) Uani 1 1 d . . . . .
H7A H -0.4932 0.2187 0.7368 0.039 Uiso 1 1 calc R U . . .
H7B H -0.3158 0.2161 0.8265 0.039 Uiso 1 1 calc R U . . .
H7C H -0.4563 0.2272 0.8858 0.039 Uiso 1 1 calc R U . . .
C31 C -0.4383(2) 0.01506(6) 0.84128(17) 0.0215(4) Uani 1 1 d . . . . .
H31 H -0.3736 0.0314 0.9111 0.026 Uiso 1 1 calc R U . . .
C9 C -0.1137(3) 0.19393(7) 1.08710(19) 0.0315(5) Uani 1 1 d . . . . .
H9A H -0.1434 0.1946 1.1660 0.047 Uiso 1 1 calc R U . . .
H9B H -0.1629 0.2194 1.0335 0.047 Uiso 1 1 calc R U . . .
H9C H 0.0011 0.1962 1.1066 0.047 Uiso 1 1 calc R U . . .
C26 C -0.49602(19) 0.03640(6) 0.72191(16) 0.0182(4) Uani 1 1 d . . . . .
C25 C -0.45785(19) 0.08384(6) 0.69889(16) 0.0180(4) Uani 1 1 d . . . . .
C10 C -0.12891(18) 0.12277(6) 0.67995(15) 0.0149(3) Uani 1 1 d . . . . .
C11 C -0.05575(18) 0.07964(6) 0.68368(15) 0.0165(3) Uani 1 1 d . . . . .
C12 C 0.0207(2) 0.06965(6) 0.58940(17) 0.0222(4) Uani 1 1 d . . . . .
H12 H 0.0719 0.0415 0.5913 0.027 Uiso 1 1 calc R U . . .
C13 C 0.0212(2) 0.10093(6) 0.49366(17) 0.0243(4) Uani 1 1 d . . . . .
H13 H 0.0720 0.0937 0.4313 0.029 Uiso 1 1 calc R U . . .
C14 C -0.0538(2) 0.14302(6) 0.49009(17) 0.0228(4) Uani 1 1 d . . . . .
H14 H -0.0545 0.1636 0.4241 0.027 Uiso 1 1 calc R U . . .
C15 C -0.12850(19) 0.15520(6) 0.58352(16) 0.0180(4) Uani 1 1 d . . . . .
C28 C -0.6319(2) -0.03423(6) 0.63455(18) 0.0273(4) Uani 1 1 d . . . . .
H28 H -0.6971 -0.0506 0.5651 0.033 Uiso 1 1 calc R U . . .
C18 C -0.0691(3) 0.23488(7) 0.6699(2) 0.0351(5) Uani 1 1 d . . . . .
H18A H -0.0318 0.2222 0.7555 0.053 Uiso 1 1 calc R U . . .
H18B H -0.1147 0.2647 0.6737 0.053 Uiso 1 1 calc R U . . .
H18C H 0.0196 0.2376 0.6340 0.053 Uiso 1 1 calc R U . . .
C19 C -0.05299(19) 0.04391(6) 0.78683(16) 0.0185(4) Uani 1 1 d . . . . .
H19 H -0.1273 0.0541 0.8344 0.022 Uiso 1 1 calc R U . . .
C21 C 0.1151(2) 0.04028(7) 0.88343(18) 0.0267(4) Uani 1 1 d . . . . .
H21A H 0.1897 0.0295 0.8396 0.040 Uiso 1 1 calc R U . . .
H21B H 0.1124 0.0191 0.9509 0.040 Uiso 1 1 calc R U . . .
H21C H 0.1483 0.0700 0.9203 0.040 Uiso 1 1 calc R U . . .
C27 C -0.5934(2) 0.01107(6) 0.61898(17) 0.0223(4) Uani 1 1 d . . . . .
H27 H -0.6330 0.0250 0.5384 0.027 Uiso 1 1 calc R U . . .
C20 C -0.1089(2) -0.00327(6) 0.72879(18) 0.0256(4) Uani 1 1 d . . . . .
H20A H -0.2123 -0.0004 0.6661 0.038 Uiso 1 1 calc R U . . .
H20B H -0.1165 -0.0239 0.7962 0.038 Uiso 1 1 calc R U . . .
H20C H -0.0330 -0.0152 0.6877 0.038 Uiso 1 1 calc R U . . .
C16 C -0.1969(2) 0.20315(6) 0.58450(17) 0.0216(4) Uani 1 1 d . . . . .
H16 H -0.2852 0.2010 0.6237 0.026 Uiso 1 1 calc R U . . .
C17 C -0.2644(2) 0.22479(7) 0.45076(18) 0.0299(4) Uani 1 1 d . . . . .
H17A H -0.1781 0.2308 0.4141 0.045 Uiso 1 1 calc R U . . .
H17B H -0.3177 0.2531 0.4585 0.045 Uiso 1 1 calc R U . . .
H17C H -0.3397 0.2040 0.3957 0.045 Uiso 1 1 calc R U . . .
C8 C -0.0912(2) 0.10898(7) 1.10511(18) 0.0297(4) Uani 1 1 d . . . . .
H8A H -0.1200 0.0802 1.0607 0.045 Uiso 1 1 calc R U . . .
H8B H -0.1273 0.1093 1.1811 0.045 Uiso 1 1 calc R U . . .
H8C H 0.0234 0.1126 1.1295 0.045 Uiso 1 1 calc R U . . .
C23 C -0.5448(2) 0.13237(6) 0.47850(17) 0.0239(4) Uani 1 1 d . . . . .
H23A H -0.6133 0.1081 0.4307 0.029 Uiso 1 1 calc R U . . .
H23B H -0.4574 0.1366 0.4404 0.029 Uiso 1 1 calc R U . . .
C29 C -0.5727(2) -0.05510(6) 0.75432(18) 0.0275(4) Uani 1 1 d . . . . .
H29 H -0.5978 -0.0856 0.7654 0.033 Uiso 1 1 calc R U . . .
C30 C -0.4763(2) -0.03047(6) 0.85724(18) 0.0248(4) Uani 1 1 d . . . . .
H30 H -0.4368 -0.0445 0.9376 0.030 Uiso 1 1 calc R U . . .
C22 C -0.6419(2) 0.17665(7) 0.4621(2) 0.0326(5) Uani 1 1 d . . . . .
H22A H -0.7275 0.1731 0.5011 0.049 Uiso 1 1 calc R U . . .
H22B H -0.6862 0.1832 0.3717 0.049 Uiso 1 1 calc R U . . .
H22C H -0.5732 0.2015 0.5032 0.049 Uiso 1 1 calc R U . . .
N1 N -0.20402(15) 0.13426(4) 0.77997(12) 0.0140(3) Uani 1 1 d . . . . .
O1 O 0.03954(14) 0.15239(4) 0.91425(12) 0.0263(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.491(2) . ?
C1 C24 1.497(2) . ?
C1 C25 1.501(2) . ?
C1 C5 1.535(2) . ?
C5 C6 1.529(2) . ?
C5 C7 1.535(2) . ?
C5 C4 1.536(2) . ?
C4 C3 1.540(2) . ?
C3 C8 1.536(2) . ?
C3 C9 1.537(2) . ?
C3 C2 1.537(2) . ?
C2 O1 1.226(2) . ?
C2 N1 1.363(2) . ?
C24 C25 1.302(2) . ?
C24 C23 1.490(2) . ?
C31 C30 1.387(3) . ?
C31 C26 1.387(2) . ?
C26 C27 1.397(2) . ?
C26 C25 1.457(2) . ?
C10 C11 1.401(2) . ?
C10 C15 1.406(2) . ?
C10 N1 1.453(2) . ?
C11 C12 1.398(2) . ?
C11 C19 1.519(2) . ?
C12 C13 1.378(3) . ?
C13 C14 1.382(3) . ?
C14 C15 1.394(2) . ?
C15 C16 1.517(2) . ?
C28 C27 1.381(3) . ?
C28 C29 1.386(3) . ?
C18 C16 1.531(3) . ?
C19 C20 1.528(2) . ?
C19 C21 1.533(2) . ?
C16 C17 1.528(2) . ?
C23 C22 1.521(3) . ?
C29 C30 1.383(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
N1 C1 C24 118.16(13) . . ?
N1 C1 C25 119.26(13) . . ?
C24 C1 C25 51.48(11) . . ?
N1 C1 C5 111.05(13) . . ?
C24 C1 C5 123.78(14) . . ?
C25 C1 C5 121.39(13) . . ?
C6 C5 C1 110.42(14) . . ?
C6 C5 C7 108.67(14) . . ?
C1 C5 C7 111.62(14) . . ?
C6 C5 C4 108.32(14) . . ?
C1 C5 C4 106.15(13) . . ?
C7 C5 C4 111.60(14) . . ?
C5 C4 C3 115.30(13) . . ?
C8 C3 C9 107.68(15) . . ?
C8 C3 C2 105.71(14) . . ?
C9 C3 C2 108.40(14) . . ?
C8 C3 C4 109.35(14) . . ?
C9 C3 C4 111.70(15) . . ?
C2 C3 C4 113.68(14) . . ?
O1 C2 N1 121.06(15) . . ?
O1 C2 C3 119.21(15) . . ?
N1 C2 C3 119.68(14) . . ?
C25 C24 C23 147.43(17) . . ?
C25 C24 C1 64.43(12) . . ?
C23 C24 C1 148.14(15) . . ?
C30 C31 C26 120.47(16) . . ?
C31 C26 C27 118.48(16) . . ?
C31 C26 C25 122.90(15) . . ?
C27 C26 C25 118.62(15) . . ?
C24 C25 C26 146.48(17) . . ?
C24 C25 C1 64.10(12) . . ?
C26 C25 C1 149.35(15) . . ?
C11 C10 C15 121.56(15) . . ?
C11 C10 N1 118.81(14) . . ?
C15 C10 N1 119.62(14) . . ?
C12 C11 C10 118.18(15) . . ?
C12 C11 C19 118.83(15) . . ?
C10 C11 C19 122.98(14) . . ?
C13 C12 C11 120.99(16) . . ?
C12 C13 C14 120.11(16) . . ?
C13 C14 C15 121.29(16) . . ?
C14 C15 C10 117.84(16) . . ?
C14 C15 C16 120.27(15) . . ?
C10 C15 C16 121.77(14) . . ?
C27 C28 C29 119.58(17) . . ?
C11 C19 C20 112.19(14) . . ?
C11 C19 C21 110.86(14) . . ?
C20 C19 C21 110.16(14) . . ?
C28 C27 C26 121.22(17) . . ?
C15 C16 C17 114.56(15) . . ?
C15 C16 C18 109.90(15) . . ?
C17 C16 C18 109.55(15) . . ?
C24 C23 C22 114.71(16) . . ?
C30 C29 C28 119.89(17) . . ?
C29 C30 C31 120.35(17) . . ?
C2 N1 C10 116.95(13) . . ?
C2 N1 C1 124.29(13) . . ?
C10 N1 C1 118.55(12) . . ?

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.059

_shelxl_version_number           2014-3


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

data_6MAC_TrCODCl
_database_code_depnum_ccdc_archive 'CCDC 1024538'
_audit_update_record             
;
2016-01-29 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            6MAC_IrCODCl
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H43 Cl Ir N O'
_chemical_formula_sum            'C29 H43 Cl Ir N O'
_chemical_formula_weight         649.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   15.8695(19)
_cell_length_b                   11.8315(13)
_cell_length_c                   14.6016(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.061(3)
_cell_angle_gamma                90
_cell_volume                     2726.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_F_000             1304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    5.016
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6304
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
Abscor.  T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku AFC-12 with Saturn 724+ CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30408
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.103
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             4778
_reflns_number_gt                4496
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0662P)²+4.0498P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4778
_refine_ls_number_parameters     306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
Ir1 Ir 0.16119(2) 0.70074(2) 0.71034(2) 0.01806(10) Uani 1 1 d . . . . .
Cl1 Cl 0.21141(7) 0.75020(10) 0.86422(7) 0.0257(2) Uani 1 1 d . . . . .
N1 N 0.3258(2) 0.5849(3) 0.7073(2) 0.0157(7) Uani 1 1 d . . . . .
O1 O 0.44930(19) 0.4890(3) 0.7346(2) 0.0315(7) Uani 1 1 d . . . . .
C1 C 0.2801(3) 0.6812(4) 0.6932(3) 0.0179(9) Uani 1 1 d . . . . .
C5 C 0.3349(3) 0.7846(3) 0.6779(3) 0.0201(9) Uani 1 1 d . . . . .
C2 C 0.4147(3) 0.5795(4) 0.7344(3) 0.0214(9) Uani 1 1 d . . . . .
C10 C 0.2846(2) 0.4742(3) 0.6982(3) 0.0189(8) Uani 1 1 d . . . . .
C25 C 0.1015(3) 0.5966(4) 0.6056(3) 0.0275(10) Uani 1 1 d . . . . .
H25 H 0.1402 0.5435 0.5799 0.033 Uiso 1 1 calc R U . . .
C11 C 0.2632(3) 0.4199(4) 0.7773(3) 0.0217(9) Uani 1 1 d . . . . .
C7 C 0.3698(3) 0.7733(4) 0.5842(3) 0.0246(9) Uani 1 1 d . . . . .
H7A H 0.4004 0.7034 0.5822 0.037 Uiso 1 1 calc R U . . .
H7B H 0.4073 0.8353 0.5758 0.037 Uiso 1 1 calc R U . . .
H7C H 0.3237 0.7740 0.5360 0.037 Uiso 1 1 calc R U . . .
C4 C 0.4052(3) 0.7901(3) 0.7585(3) 0.0230(10) Uani 1 1 d . . . . .
H4A H 0.4409 0.8549 0.7497 0.028 Uiso 1 1 calc R U . . .
H4B H 0.3793 0.8024 0.8150 0.028 Uiso 1 1 calc R U . . .
C15 C 0.2712(3) 0.4253(4) 0.6106(3) 0.0219(9) Uani 1 1 d . . . . .
C26 C 0.1064(3) 0.7088(4) 0.5707(3) 0.0335(13) Uani 1 1 d . . . . .
H26 H 0.1480 0.7176 0.5262 0.040 Uiso 1 1 calc R U . . .
C19 C 0.2807(3) 0.4692(4) 0.8730(3) 0.0238(9) Uani 1 1 d . . . . .
H19 H 0.2982 0.5480 0.8666 0.029 Uiso 1 1 calc R U . . .
C6 C 0.2855(3) 0.8957(4) 0.6760(3) 0.0286(10) Uani 1 1 d . . . . .
H6A H 0.2383 0.8919 0.6293 0.043 Uiso 1 1 calc R U . . .
H6B H 0.3220 0.9569 0.6626 0.043 Uiso 1 1 calc R U . . .
H6C H 0.2653 0.9080 0.7349 0.043 Uiso 1 1 calc R U . . .
C17 C 0.2367(3) 0.4541(4) 0.4376(3) 0.0340(11) Uani 1 1 d . . . . .
H17A H 0.2452 0.3763 0.4225 0.051 Uiso 1 1 calc R U . . .
H17B H 0.2500 0.5011 0.3874 0.051 Uiso 1 1 calc R U . . .
H17C H 0.1786 0.4656 0.4482 0.051 Uiso 1 1 calc R U . . .
C29 C 0.0509(3) 0.8053(4) 0.7294(4) 0.0392(14) Uani 1 1 d . . . . .
H29 H 0.0595 0.8579 0.7814 0.047 Uiso 1 1 calc R U . . .
C16 C 0.2944(3) 0.4851(4) 0.5244(3) 0.0239(9) Uani 1 1 d . . . . .
H16 H 0.2884 0.5665 0.5343 0.029 Uiso 1 1 calc R U . . .
C22 C 0.0300(3) 0.6965(5) 0.7536(4) 0.0379(15) Uani 1 1 d . . . . .
H22 H 0.0277 0.6851 0.8198 0.046 Uiso 1 1 calc R U . . .
C3 C 0.4612(3) 0.6852(4) 0.7706(3) 0.0231(10) Uani 1 1 d . . . . .
C21 C 0.2024(3) 0.4692(4) 0.9253(3) 0.0326(11) Uani 1 1 d . . . . .
H21A H 0.1576 0.5102 0.8906 0.049 Uiso 1 1 calc R U . . .
H21B H 0.2157 0.5045 0.9842 0.049 Uiso 1 1 calc R U . . .
H21C H 0.1846 0.3927 0.9339 0.049 Uiso 1 1 calc R U . . .
C20 C 0.3535(3) 0.4068(4) 0.9282(3) 0.0338(11) Uani 1 1 d . . . . .
H20A H 0.3395 0.3281 0.9320 0.051 Uiso 1 1 calc R U . . .
H20B H 0.3625 0.4380 0.9891 0.051 Uiso 1 1 calc R U . . .
H20C H 0.4041 0.4150 0.8982 0.051 Uiso 1 1 calc R U . . .
C12 C 0.2259(3) 0.3137(4) 0.7662(3) 0.0290(11) Uani 1 1 d . . . . .
H12 H 0.2096 0.2763 0.8175 0.035 Uiso 1 1 calc R U . . .
C9 C 0.5432(3) 0.6959(4) 0.7246(4) 0.0337(12) Uani 1 1 d . . . . .
H9A H 0.5734 0.6256 0.7299 0.051 Uiso 1 1 calc R U . . .
H9B H 0.5778 0.7546 0.7544 0.051 Uiso 1 1 calc R U . . .
H9C H 0.5298 0.7144 0.6607 0.051 Uiso 1 1 calc R U . . .
C13 C 0.2123(3) 0.2621(4) 0.6805(4) 0.0356(11) Uani 1 1 d . . . . .
H13 H 0.1888 0.1902 0.6746 0.043 Uiso 1 1 calc R U . . .
C24 C 0.0238(3) 0.5410(5) 0.6363(3) 0.0357(12) Uani 1 1 d . . . . .
H24A H 0.0411 0.4750 0.6729 0.043 Uiso 1 1 calc R U . . .
H24B H -0.0122 0.5157 0.5825 0.043 Uiso 1 1 calc R U . . .
C23 C -0.0270(3) 0.6187(5) 0.6926(4) 0.0393(13) Uani 1 1 d . . . . .
H23A H -0.0654 0.6637 0.6513 0.047 Uiso 1 1 calc R U . . .
H23B H -0.0607 0.5735 0.7305 0.047 Uiso 1 1 calc R U . . .
C18 C 0.3861(3) 0.4633(5) 0.5079(3) 0.0374(12) Uani 1 1 d . . . . .
H18A H 0.4228 0.4861 0.5611 0.056 Uiso 1 1 calc R U . . .
H18B H 0.3994 0.5059 0.4553 0.056 Uiso 1 1 calc R U . . .
H18C H 0.3938 0.3842 0.4967 0.056 Uiso 1 1 calc R U . . .
C27 C 0.0320(4) 0.7885(5) 0.5547(4) 0.0488(16) Uani 1 1 d . . . . .
H27A H -0.0194 0.7450 0.5397 0.059 Uiso 1 1 calc R U . . .
H27B H 0.0397 0.8369 0.5026 0.059 Uiso 1 1 calc R U . . .
C14 C 0.2345(3) 0.3196(4) 0.6039(3) 0.0319(11) Uani 1 1 d . . . . .
H14 H 0.2244 0.2858 0.5463 0.038 Uiso 1 1 calc R U . . .
C28 C 0.0225(4) 0.8610(6) 0.6385(4) 0.0545(16) Uani 1 1 d . . . . .
H28A H 0.0550 0.9299 0.6337 0.065 Uiso 1 1 calc R U . . .
H28B H -0.0366 0.8823 0.6380 0.065 Uiso 1 1 calc R U . . .
C8 C 0.4859(3) 0.6663(5) 0.8738(3) 0.0381(12) Uani 1 1 d . . . . .
H8A H 0.4356 0.6613 0.9048 0.057 Uiso 1 1 calc R U . . .
H8B H 0.5200 0.7284 0.8985 0.057 Uiso 1 1 calc R U . . .
H8C H 0.5176 0.5973 0.8827 0.057 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
Ir1 C1 1.944(5) . ?
Ir1 C25 2.109(4) . ?
Ir1 C26 2.133(5) . ?
Ir1 C29 2.185(5) . ?
Ir1 C22 2.239(5) . ?
Ir1 Cl1 2.3765(10) . ?
N1 C1 1.354(6) . ?
N1 C2 1.426(5) . ?
N1 C10 1.463(5) . ?
O1 C2 1.203(5) . ?
C1 C5 1.531(6) . ?
C5 C6 1.528(6) . ?
C5 C4 1.536(6) . ?
C5 C7 1.536(6) . ?
C2 C3 1.519(6) . ?
C10 C11 1.395(6) . ?
C10 C15 1.400(6) . ?
C25 C26 1.426(7) . ?
C25 C24 1.507(6) . ?
C25 H25 0.9800 . ?
C11 C12 1.391(6) . ?
C11 C19 1.514(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C4 C3 1.526(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C15 C14 1.378(6) . ?
C15 C16 1.522(6) . ?
C26 C27 1.509(7) . ?
C26 H26 0.9800 . ?
C19 C21 1.525(6) . ?
C19 C20 1.528(6) . ?
C19 H19 0.9800 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C17 C16 1.528(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C29 C22 1.385(7) . ?
C29 C28 1.508(8) . ?
C29 H29 0.9800 . ?
C16 C18 1.522(6) . ?
C16 H16 0.9800 . ?
C22 C23 1.512(7) . ?
C22 H22 0.9800 . ?
C3 C9 1.531(7) . ?
C3 C8 1.532(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C12 C13 1.388(7) . ?
C12 H12 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C13 C14 1.386(7) . ?
C13 H13 0.9300 . ?
C24 C23 1.520(7) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C27 C28 1.515(9) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C14 H14 0.9300 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ir1 C25 101.84(17) . . ?
C1 Ir1 C26 100.73(19) . . ?
C25 Ir1 C26 39.28(18) . . ?
C1 Ir1 C29 152.3(2) . . ?
C25 Ir1 C29 96.8(2) . . ?
C26 Ir1 C29 81.1(2) . . ?
C1 Ir1 C22 167.9(2) . . ?
C25 Ir1 C22 80.33(18) . . ?
C26 Ir1 C22 88.5(2) . . ?
C29 Ir1 C22 36.5(2) . . ?
C1 Ir1 Cl1 85.26(12) . . ?
C25 Ir1 Cl1 155.45(13) . . ?
C26 Ir1 Cl1 162.77(14) . . ?
C29 Ir1 Cl1 86.18(16) . . ?
C22 Ir1 Cl1 88.14(15) . . ?
C1 N1 C2 125.3(4) . . ?
C1 N1 C10 120.9(3) . . ?
C2 N1 C10 113.8(3) . . ?
N1 C1 C5 113.1(4) . . ?
N1 C1 Ir1 126.3(3) . . ?
C5 C1 Ir1 119.8(3) . . ?
C6 C5 C1 113.1(4) . . ?
C6 C5 C4 107.9(4) . . ?
C1 C5 C4 107.4(3) . . ?
C6 C5 C7 106.9(4) . . ?
C1 C5 C7 108.9(3) . . ?
C4 C5 C7 112.7(4) . . ?
O1 C2 N1 118.6(4) . . ?
O1 C2 C3 121.8(4) . . ?
N1 C2 C3 119.4(4) . . ?
C11 C10 C15 122.6(4) . . ?
C11 C10 N1 118.9(3) . . ?
C15 C10 N1 118.4(4) . . ?
C26 C25 C24 126.1(4) . . ?
C26 C25 Ir1 71.3(3) . . ?
C24 C25 Ir1 110.9(3) . . ?
C26 C25 H25 113.6 . . ?
C24 C25 H25 113.6 . . ?
Ir1 C25 H25 113.6 . . ?
C12 C11 C10 117.3(4) . . ?
C12 C11 C19 119.4(4) . . ?
C10 C11 C19 123.4(4) . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C4 C5 114.9(4) . . ?
C3 C4 H4A 108.5 . . ?
C5 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
C5 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
C14 C15 C10 117.5(4) . . ?
C14 C15 C16 120.1(4) . . ?
C10 C15 C16 122.4(4) . . ?
C25 C26 C27 124.5(5) . . ?
C25 C26 Ir1 69.5(3) . . ?
C27 C26 Ir1 114.1(4) . . ?
C25 C26 H26 113.7 . . ?
C27 C26 H26 113.7 . . ?
Ir1 C26 H26 113.7 . . ?
C11 C19 C21 112.4(4) . . ?
C11 C19 C20 110.8(4) . . ?
C21 C19 C20 110.3(4) . . ?
C11 C19 H19 107.7 . . ?
C21 C19 H19 107.7 . . ?
C20 C19 H19 107.7 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C22 C29 C28 125.0(6) . . ?
C22 C29 Ir1 73.9(3) . . ?
C28 C29 Ir1 107.7(4) . . ?
C22 C29 H29 114.2 . . ?
C28 C29 H29 114.2 . . ?
Ir1 C29 H29 114.2 . . ?
C18 C16 C15 111.8(4) . . ?
C18 C16 C17 109.1(4) . . ?
C15 C16 C17 113.5(4) . . ?
C18 C16 H16 107.4 . . ?
C15 C16 H16 107.4 . . ?
C17 C16 H16 107.4 . . ?
C29 C22 C23 124.0(5) . . ?
C29 C22 Ir1 69.7(3) . . ?
C23 C22 Ir1 111.3(3) . . ?
C29 C22 H22 114.5 . . ?
C23 C22 H22 114.5 . . ?
Ir1 C22 H22 114.5 . . ?
C2 C3 C4 112.0(4) . . ?
C2 C3 C9 108.7(4) . . ?
C4 C3 C9 113.2(4) . . ?
C2 C3 C8 106.6(4) . . ?
C4 C3 C8 108.5(4) . . ?
C9 C3 C8 107.6(4) . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13 C12 C11 121.7(4) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C14 C13 C12 118.9(4) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C25 C24 C23 113.2(4) . . ?
C25 C24 H24A 108.9 . . ?
C23 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C23 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C22 C23 C24 111.6(4) . . ?
C22 C23 H23A 109.3 . . ?
C24 C23 H23A 109.3 . . ?
C22 C23 H23B 109.3 . . ?
C24 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C26 C27 C28 111.9(5) . . ?
C26 C27 H27A 109.2 . . ?
C28 C27 H27A 109.2 . . ?
C26 C27 H27B 109.2 . . ?
C28 C27 H27B 109.2 . . ?
H27A C27 H27B 107.9 . . ?
C15 C14 C13 122.0(4) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C29 C28 C27 114.7(5) . . ?
C29 C28 H28A 108.6 . . ?
C27 C28 H28A 108.6 . . ?
C29 C28 H28B 108.6 . . ?
C27 C28 H28B 108.6 . . ?
H28A C28 H28B 107.6 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         1.732
_refine_diff_density_min         -2.695
_refine_diff_density_rms         0.157

_shelxl_version_number           2014-3

