# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_sa4505a
_database_code_depnum_ccdc_archive 'CCDC 1564093'
_audit_update_record             
;
2017-07-23 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;
_audit_creation_date             2015-12-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H20 I N O'
_chemical_formula_sum            'C24 H20 I N O'
_chemical_formula_weight         465.31
_chemical_melting_point          ?
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'
I I -0.4742 1.8119 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-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                   14.565(3)
_cell_length_b                   11.480(2)
_cell_length_c                   24.047(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4020.9(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9625
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4852
_cell_measurement_theta_min      2.1965
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.606
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18287
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.412
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
scan:
	Number of images: 330
	           Slice: -110.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 7.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.0655
	          2theta: -20.0331
scan:
	Number of images: 120
	           Slice: -5.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 7.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.0655
	          2theta: -20.0331
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             5114
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0535
_diffrn_orient_matrix_UB_12      0.0558
_diffrn_orient_matrix_UB_13      0.0402
_diffrn_orient_matrix_UB_21      -0.0534
_diffrn_orient_matrix_UB_22      0.0270
_diffrn_orient_matrix_UB_23      0.0336
_diffrn_orient_matrix_UB_31      0.0055
_diffrn_orient_matrix_UB_32      -0.0274
_diffrn_orient_matrix_UB_33      0.0308
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4363
_reflns_number_total             4590
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4590
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.192
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0230P)²+4.1850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0766
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 I1A-C17 = I1-C17
 2.13 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
I1: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
I1 \\sim I1A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04
Uanis(I1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(I1A) \\sim Ueq, Uanis(I1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(I1A)=1-FVAR(1)
 Sof(I1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
5.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.48747(12) 0.49950(15) 0.28225(7) 0.0287(4) Uani 1 1 d . . . . .
N1 N 0.53649(13) 0.68858(16) 0.29374(8) 0.0216(4) Uani 1 1 d . . . . .
C1 C 0.51668(16) 0.7159(2) 0.38719(9) 0.0226(4) Uani 1 1 d . . . . .
C2 C 0.52109(17) 0.7776(2) 0.43639(10) 0.0292(5) Uani 1 1 d . . . . .
H2 H 0.5031 0.7435 0.4697 0.035 Uiso 1 1 calc R . . . .
C3 C 0.55298(19) 0.8921(2) 0.43509(11) 0.0331(6) Uani 1 1 d . . . . .
H3 H 0.5567 0.9346 0.4679 0.040 Uiso 1 1 calc R . . . .
C4 C 0.57928(19) 0.9429(2) 0.38530(12) 0.0334(6) Uani 1 1 d . . . . .
H4 H 0.5996 1.0197 0.3852 0.040 Uiso 1 1 calc R . . . .
C5 C 0.57590(17) 0.8814(2) 0.33538(11) 0.0282(5) Uani 1 1 d . . . . .
H5 H 0.5937 0.9154 0.3020 0.034 Uiso 1 1 calc R . . . .
C6 C 0.54504(15) 0.76809(19) 0.33761(9) 0.0221(4) Uani 1 1 d . . . . .
C7 C 0.50068(15) 0.5845(2) 0.31091(9) 0.0227(4) Uani 1 1 d . . . . .
C8 C 0.48291(15) 0.5933(2) 0.37482(9) 0.0221(4) Uani 1 1 d . . . . .
C9 C 0.53877(16) 0.4960(2) 0.40232(9) 0.0230(5) Uani 1 1 d . . . . .
C10 C 0.50610(18) 0.3818(2) 0.40073(10) 0.0270(5) Uani 1 1 d . . . . .
H10 H 0.4505 0.3657 0.3833 0.032 Uiso 1 1 calc R . . . .
C11 C 0.55589(18) 0.2925(2) 0.42486(10) 0.0299(5) Uani 1 1 d . . . . .
H11 H 0.5329 0.2170 0.4236 0.036 Uiso 1 1 calc R . . . .
C12 C 0.63950(18) 0.3130(2) 0.45100(10) 0.0292(5) Uani 1 1 d . . . . .
C13 C 0.67257(17) 0.4264(2) 0.45139(11) 0.0315(5) Uani 1 1 d . . . . .
H13 H 0.7288 0.4422 0.4680 0.038 Uiso 1 1 calc R . . . .
C14 C 0.62298(17) 0.5167(2) 0.42731(10) 0.0289(5) Uani 1 1 d . . . . .
H14 H 0.6466 0.5920 0.4280 0.035 Uiso 1 1 calc R . . . .
C15 C 0.6919(2) 0.2165(3) 0.47936(13) 0.0423(7) Uani 1 1 d . . . . .
H15A H 0.6712 0.2092 0.5171 0.063 Uiso 1 1 calc GR . . . .
H15B H 0.7563 0.2343 0.4790 0.063 Uiso 1 1 calc GR . . . .
H15C H 0.6815 0.1445 0.4600 0.063 Uiso 1 1 calc GR . . . .
C16 C 0.38287(17) 0.5797(2) 0.39127(9) 0.0243(5) Uani 1 1 d . . . . .
H16 H 0.3722 0.5606 0.4283 0.029 Uiso 1 1 calc R . . . .
C17 C 0.30831(15) 0.5916(2) 0.35961(10) 0.0244(5) Uani 1 1 d D . . . .
C18 C 0.30075(15) 0.6286(2) 0.30100(10) 0.0234(5) Uani 1 1 d . . . . .
C19 C 0.26354(17) 0.5543(2) 0.26121(10) 0.0288(5) Uani 1 1 d . . . . .
H19 H 0.2430 0.4809 0.2719 0.035 Uiso 1 1 calc R . . . .
C20 C 0.25661(19) 0.5875(3) 0.20618(11) 0.0346(6) Uani 1 1 d . . . . .
H20 H 0.2313 0.5371 0.1800 0.041 Uiso 1 1 calc R . . . .
C21 C 0.28793(18) 0.6969(3) 0.19026(11) 0.0360(6) Uani 1 1 d . . . . .
H21 H 0.2838 0.7197 0.1532 0.043 Uiso 1 1 calc R . . . .
C22 C 0.32506(18) 0.7718(2) 0.22898(12) 0.0347(6) Uani 1 1 d . . . . .
H22 H 0.3465 0.8446 0.2180 0.042 Uiso 1 1 calc R . . . .
C23 C 0.33055(16) 0.7386(2) 0.28483(11) 0.0274(5) Uani 1 1 d . . . . .
H23 H 0.3541 0.7899 0.3111 0.033 Uiso 1 1 calc R . . . .
C24 C 0.55856(17) 0.7140(2) 0.23597(10) 0.0274(5) Uani 1 1 d . . . . .
H24A H 0.5219 0.7783 0.2233 0.041 Uiso 1 1 calc GR . . . .
H24B H 0.5459 0.6467 0.2135 0.041 Uiso 1 1 calc GR . . . .
H24C H 0.6224 0.7337 0.2329 0.041 Uiso 1 1 calc GR . . . .
I1 I 0.1794(2) 0.5441(3) 0.39568(16) 0.0344(4) Uani 0.54(3) 1 d D U P A 1
I1A I 0.1792(3) 0.5611(9) 0.3987(2) 0.0463(7) Uani 0.46(3) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.210(3) . ?
N1 C6 1.401(3) . ?
N1 C7 1.367(3) . ?
N1 C24 1.455(3) . ?
C1 C2 1.381(3) . ?
C1 C6 1.397(3) . ?
C1 C8 1.520(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.394(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(3) . ?
C7 C8 1.562(3) . ?
C8 C9 1.532(3) . ?
C8 C16 1.518(3) . ?
C9 C10 1.394(3) . ?
C9 C14 1.387(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(4) . ?
C12 C13 1.388(4) . ?
C12 C15 1.508(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.390(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C17 1.333(3) . ?
C17 C18 1.476(3) . ?
C17 I1 2.139(4) . ?
C17 I1A 2.131(4) . ?
C18 C19 1.392(3) . ?
C18 C23 1.390(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.381(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.390(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.378(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.399(4) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C6 N1 C24 124.66(19) . . ?
C7 N1 C6 112.07(18) . . ?
C7 N1 C24 123.21(19) . . ?
C2 C1 C6 119.8(2) . . ?
C2 C1 C8 131.2(2) . . ?
C6 C1 C8 109.01(19) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.7(2) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 121.4 . . ?
C6 C5 C4 117.2(2) . . ?
C6 C5 H5 121.4 . . ?
C1 C6 N1 109.70(19) . . ?
C5 C6 N1 128.0(2) . . ?
C5 C6 C1 122.3(2) . . ?
O1 C7 N1 126.4(2) . . ?
O1 C7 C8 125.9(2) . . ?
N1 C7 C8 107.70(18) . . ?
C1 C8 C7 101.47(18) . . ?
C1 C8 C9 114.77(19) . . ?
C9 C8 C7 106.83(18) . . ?
C16 C8 C1 110.79(19) . . ?
C16 C8 C7 114.13(18) . . ?
C16 C8 C9 108.79(18) . . ?
C10 C9 C8 119.5(2) . . ?
C14 C9 C8 122.1(2) . . ?
C14 C9 C10 118.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.6(2) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C15 121.6(2) . . ?
C13 C12 C11 117.7(2) . . ?
C13 C12 C15 120.7(2) . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.1(2) . . ?
C14 C13 H13 119.5 . . ?
C9 C14 C13 120.8(2) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C16 H16 115.8 . . ?
C17 C16 C8 128.5(2) . . ?
C17 C16 H16 115.8 . . ?
C16 C17 C18 129.5(2) . . ?
C16 C17 I1 117.2(2) . . ?
C16 C17 I1A 116.7(2) . . ?
C18 C17 I1 113.27(19) . . ?
C18 C17 I1A 113.73(19) . . ?
C19 C18 C17 120.5(2) . . ?
C23 C18 C17 120.4(2) . . ?
C23 C18 C19 119.1(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.2(2) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.3(3) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0(2) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 C22 119.9(2) . . ?
C18 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C8 C1 177.1(2) . . . . ?
O1 C7 C8 C9 56.5(3) . . . . ?
O1 C7 C8 C16 -63.8(3) . . . . ?
N1 C7 C8 C1 -1.0(2) . . . . ?
N1 C7 C8 C9 -121.5(2) . . . . ?
N1 C7 C8 C16 118.2(2) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C1 C8 C9 C10 170.4(2) . . . . ?
C1 C8 C9 C14 -11.9(3) . . . . ?
C1 C8 C16 C17 94.7(3) . . . . ?
C2 C1 C6 N1 178.6(2) . . . . ?
C2 C1 C6 C5 -1.5(4) . . . . ?
C2 C1 C8 C7 -179.1(2) . . . . ?
C2 C1 C8 C9 -64.4(3) . . . . ?
C2 C1 C8 C16 59.3(3) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 N1 -179.1(2) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C6 N1 C7 O1 -178.5(2) . . . . ?
C6 N1 C7 C8 -0.4(2) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C6 C1 C8 C7 2.1(2) . . . . ?
C6 C1 C8 C9 116.8(2) . . . . ?
C6 C1 C8 C16 -119.5(2) . . . . ?
C7 N1 C6 C1 1.8(3) . . . . ?
C7 N1 C6 C5 -178.1(2) . . . . ?
C7 C8 C9 C10 -78.0(3) . . . . ?
C7 C8 C9 C14 99.7(2) . . . . ?
C7 C8 C16 C17 -19.1(3) . . . . ?
C8 C1 C2 C3 -177.9(2) . . . . ?
C8 C1 C6 N1 -2.5(3) . . . . ?
C8 C1 C6 C5 177.5(2) . . . . ?
C8 C9 C10 C11 179.4(2) . . . . ?
C8 C9 C14 C13 -179.3(2) . . . . ?
C8 C16 C17 C18 -4.6(4) . . . . ?
C8 C16 C17 I1 172.4(2) . . . . ?
C8 C16 C17 I1A 178.7(4) . . . . ?
C9 C8 C16 C17 -138.3(3) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C10 C9 C14 C13 -1.5(4) . . . . ?
C10 C11 C12 C13 -1.0(4) . . . . ?
C10 C11 C12 C15 177.4(2) . . . . ?
C11 C12 C13 C14 1.1(4) . . . . ?
C12 C13 C14 C9 0.2(4) . . . . ?
C14 C9 C10 C11 1.6(4) . . . . ?
C15 C12 C13 C14 -177.4(2) . . . . ?
C16 C8 C9 C10 45.7(3) . . . . ?
C16 C8 C9 C14 -136.6(2) . . . . ?
C16 C17 C18 C19 119.1(3) . . . . ?
C16 C17 C18 C23 -61.0(4) . . . . ?
C17 C18 C19 C20 -179.6(2) . . . . ?
C17 C18 C23 C22 178.5(2) . . . . ?
C18 C19 C20 C21 0.4(4) . . . . ?
C19 C18 C23 C22 -1.6(3) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C20 C21 C22 C23 -0.7(4) . . . . ?
C21 C22 C23 C18 1.7(4) . . . . ?
C23 C18 C19 C20 0.6(4) . . . . ?
C24 N1 C6 C1 179.0(2) . . . . ?
C24 N1 C6 C5 -0.9(4) . . . . ?
C24 N1 C7 O1 4.3(4) . . . . ?
C24 N1 C7 C8 -177.65(19) . . . . ?
I1 C17 C18 C19 -57.9(3) . . . . ?
I1 C17 C18 C23 121.9(2) . . . . ?
I1A C17 C18 C19 -64.0(4) . . . . ?
I1A C17 C18 C23 115.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1564096'
_audit_update_record             
;
2017-07-23 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;
_audit_creation_date             2017-07-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H25 N O3'
_chemical_formula_sum            'C28 H25 N O3'
_chemical_formula_weight         423.49
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.790(4)
_cell_length_b                   14.850(5)
_cell_length_c                   12.068(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.127(6)
_cell_angle_gamma                90
_cell_volume                     2274.5(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6342
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4721
_cell_measurement_theta_min      2.1109
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.83786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15603
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.199
_diffrn_reflns_theta_max         25.199
_diffrn_reflns_theta_min         2.743
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3467
_reflns_number_total             4095
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.308
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4095
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0982
_refine_ls_restrained_S_all      1.308
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0188P)²+2.0759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1497
_refine_ls_wR_factor_ref         0.1567
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15),
 C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.55216(18) 0.44593(17) 0.7008(2) 0.0472(7) Uani 1 1 d . . . . .
O2 O 0.99571(19) 0.61815(17) 0.3991(2) 0.0515(7) Uani 1 1 d . . . . .
O3 O 0.90510(18) 0.74373(17) 0.3482(2) 0.0479(7) Uani 1 1 d . . . . .
N1 N 0.5892(2) 0.5276(2) 0.8634(2) 0.0412(7) Uani 1 1 d . . . . .
C1 C 0.7363(2) 0.4605(2) 0.7946(3) 0.0332(8) Uani 1 1 d . . . . .
C2 C 0.6145(3) 0.4767(2) 0.7762(3) 0.0393(9) Uani 1 1 d . . . . .
C3 C 0.6789(3) 0.5536(2) 0.9345(3) 0.0361(8) Uani 1 1 d . . . . .
C4 C 0.6847(3) 0.6087(3) 1.0269(3) 0.0508(10) Uani 1 1 d . . . . .
H4 H 0.623289 0.634893 1.050180 0.061 Uiso 1 1 calc R . . . .
C5 C 0.7836(3) 0.6245(3) 1.0846(3) 0.0540(11) Uani 1 1 d . . . . .
H5 H 0.789880 0.661092 1.149650 0.065 Uiso 1 1 calc R . . . .
C6 C 0.8726(3) 0.5882(3) 1.0493(4) 0.0626(12) Uani 1 1 d . . . . .
H6 H 0.939588 0.600682 1.089813 0.075 Uiso 1 1 calc R . . . .
C7 C 0.8660(3) 0.5331(3) 0.9545(3) 0.0518(11) Uani 1 1 d . . . . .
H7 H 0.927759 0.509164 0.929253 0.062 Uiso 1 1 calc R . . . .
C8 C 0.7683(3) 0.5145(2) 0.8989(3) 0.0383(8) Uani 1 1 d . . . . .
C9 C 0.4834(3) 0.5651(3) 0.8660(3) 0.0535(11) Uani 1 1 d . . . . .
H9A H 0.484507 0.629885 0.850992 0.080 Uiso 1 1 calc GR . . . .
H9B H 0.461111 0.554779 0.939776 0.080 Uiso 1 1 calc GR . . . .
H9C H 0.433797 0.535504 0.808919 0.080 Uiso 1 1 calc GR . . . .
C10 C 0.7537(2) 0.3584(2) 0.8068(3) 0.0328(8) Uani 1 1 d . . . . .
C11 C 0.7293(3) 0.3041(2) 0.7135(3) 0.0356(8) Uani 1 1 d . . . . .
H11 H 0.703683 0.330952 0.643923 0.043 Uiso 1 1 calc R . . . .
C12 C 0.7416(3) 0.2121(2) 0.7199(3) 0.0391(9) Uani 1 1 d . . . . .
H12 H 0.723959 0.176508 0.654805 0.047 Uiso 1 1 calc R . . . .
C13 C 0.7792(3) 0.1705(2) 0.8193(3) 0.0438(9) Uani 1 1 d . . . . .
C14 C 0.8049(3) 0.2249(3) 0.9124(3) 0.0454(9) Uani 1 1 d . . . . .
H14 H 0.832248 0.198081 0.981463 0.054 Uiso 1 1 calc R . . . .
C15 C 0.7916(3) 0.3175(2) 0.9067(3) 0.0388(8) Uani 1 1 d . . . . .
H15 H 0.808558 0.353034 0.971888 0.047 Uiso 1 1 calc R . . . .
C16 C 0.7943(4) 0.0690(3) 0.8271(4) 0.0699(13) Uani 1 1 d . . . . .
H16A H 0.738400 0.042525 0.865309 0.105 Uiso 1 1 calc GR . . . .
H16B H 0.863000 0.055545 0.869143 0.105 Uiso 1 1 calc GR . . . .
H16C H 0.791068 0.043663 0.751759 0.105 Uiso 1 1 calc GR . . . .
C17 C 0.7930(2) 0.4950(2) 0.6991(3) 0.0334(8) Uani 1 1 d . . . . .
H17 H 0.854806 0.462578 0.687571 0.040 Uiso 1 1 calc R . . . .
C18 C 0.7691(2) 0.5640(2) 0.6288(3) 0.0306(8) Uani 1 1 d . . . . .
C19 C 0.6746(2) 0.6231(2) 0.6290(3) 0.0307(8) Uani 1 1 d . . . . .
C20 C 0.5911(3) 0.6174(2) 0.5437(3) 0.0400(9) Uani 1 1 d . . . . .
H20 H 0.594338 0.575955 0.484165 0.048 Uiso 1 1 calc R . . . .
C21 C 0.5038(3) 0.6715(3) 0.5451(3) 0.0495(10) Uani 1 1 d . . . . .
H21 H 0.446906 0.666495 0.486830 0.059 Uiso 1 1 calc R . . . .
C22 C 0.4976(3) 0.7329(3) 0.6300(3) 0.0467(10) Uani 1 1 d . . . . .
H22 H 0.436941 0.769743 0.630400 0.056 Uiso 1 1 calc R . . . .
C23 C 0.5807(3) 0.7401(2) 0.7143(3) 0.0409(9) Uani 1 1 d . . . . .
H23 H 0.577634 0.782531 0.772680 0.049 Uiso 1 1 calc R . . . .
C24 C 0.6689(3) 0.6852(2) 0.7140(3) 0.0338(8) Uani 1 1 d . . . . .
H24 H 0.725581 0.690345 0.772414 0.041 Uiso 1 1 calc R . . . .
C25 C 0.8437(2) 0.5838(2) 0.5488(3) 0.0321(8) Uani 1 1 d . . . . .
H25 H 0.901658 0.543838 0.548142 0.038 Uiso 1 1 calc R . . . .
C26 C 0.8380(3) 0.6523(2) 0.4771(3) 0.0336(8) Uani 1 1 d . . . . .
H26 H 0.779416 0.692083 0.472085 0.040 Uiso 1 1 calc R . . . .
C27 C 0.9215(3) 0.6667(2) 0.4058(3) 0.0348(8) Uani 1 1 d . . . . .
C28 C 0.9864(3) 0.7710(3) 0.2815(4) 0.0600(12) Uani 1 1 d . . . . .
H28A H 0.997254 0.723222 0.228090 0.090 Uiso 1 1 calc GR . . . .
H28B H 1.052251 0.781760 0.330457 0.090 Uiso 1 1 calc GR . . . .
H28C H 0.964658 0.826391 0.240946 0.090 Uiso 1 1 calc GR . . . .


_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 1.222(4) . ?
O2 C27 1.203(4) . ?
O3 C27 1.341(4) . ?
O3 C28 1.449(4) . ?
N1 C2 1.366(4) . ?
N1 C3 1.399(4) . ?
N1 C9 1.467(4) . ?
C1 C2 1.564(5) . ?
C1 C8 1.506(5) . ?
C1 C10 1.536(5) . ?
C1 C17 1.525(4) . ?
C3 C4 1.378(5) . ?
C3 C8 1.397(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.401(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.371(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.389(5) . ?
C10 C15 1.384(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.377(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(5) . ?
C13 C14 1.391(5) . ?
C13 C16 1.521(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(5) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17 0.9500 . ?
C17 C18 1.341(4) . ?
C18 C19 1.494(4) . ?
C18 C25 1.470(4) . ?
C19 C20 1.392(4) . ?
C19 C24 1.388(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.379(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.381(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.381(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.391(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C25 C26 1.331(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.469(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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
C27 O3 C28 116.7(3) . . ?
C2 N1 C3 111.7(3) . . ?
C2 N1 C9 122.3(3) . . ?
C3 N1 C9 124.8(3) . . ?
C8 C1 C2 101.5(3) . . ?
C8 C1 C10 115.1(3) . . ?
C8 C1 C17 110.3(3) . . ?
C10 C1 C2 107.2(3) . . ?
C17 C1 C2 113.6(3) . . ?
C17 C1 C10 109.0(3) . . ?
O1 C2 N1 125.8(3) . . ?
O1 C2 C1 126.5(3) . . ?
N1 C2 C1 107.6(3) . . ?
C4 C3 N1 128.2(3) . . ?
C4 C3 C8 122.1(3) . . ?
C8 C3 N1 109.7(3) . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.5(4) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.9(4) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.8 . . ?
C8 C7 C6 118.4(4) . . ?
C8 C7 H7 120.8 . . ?
C3 C8 C1 109.2(3) . . ?
C7 C8 C1 130.8(3) . . ?
C7 C8 C3 119.9(3) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C1 118.7(3) . . ?
C15 C10 C1 123.2(3) . . ?
C15 C10 C11 118.1(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.1(4) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C14 117.7(3) . . ?
C12 C13 C16 121.6(4) . . ?
C14 C13 C16 120.7(4) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C10 C15 C14 120.5(3) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 C17 H17 115.0 . . ?
C18 C17 C1 129.9(3) . . ?
C18 C17 H17 115.0 . . ?
C17 C18 C19 124.7(3) . . ?
C17 C18 C25 116.9(3) . . ?
C25 C18 C19 118.3(3) . . ?
C20 C19 C18 120.6(3) . . ?
C24 C19 C18 120.6(3) . . ?
C24 C19 C20 118.8(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.0(4) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 H22 120.4 . . ?
C21 C22 C23 119.2(3) . . ?
C23 C22 H22 120.4 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 C23 120.6(3) . . ?
C19 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C18 C25 H25 116.9 . . ?
C26 C25 C18 126.3(3) . . ?
C26 C25 H25 116.9 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.4(3) . . ?
C27 C26 H26 119.8 . . ?
O2 C27 O3 123.4(3) . . ?
O2 C27 C26 126.1(3) . . ?
O3 C27 C26 110.5(3) . . ?
O3 C28 H28A 109.5 . . ?
O3 C28 H28B 109.5 . . ?
O3 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1564094'
_audit_update_record             
;
2017-07-23 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;
_audit_creation_date             2017-07-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H19 Cl I N O'
_chemical_formula_sum            'C24 H19 Cl I N O'
_chemical_formula_weight         499.75
_chemical_melting_point          ?
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'
I I -0.4742 1.8119 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2532(19)
_cell_length_b                   9.542(3)
_cell_length_c                   12.045(3)
_cell_angle_alpha                82.895(3)
_cell_angle_beta                 86.591(3)
_cell_angle_gamma                79.419(3)
_cell_volume                     1036.7(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4621
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4855
_cell_measurement_theta_min      1.4611
_shelx_estimated_absorpt_T_max   0.836
_shelx_estimated_absorpt_T_min   0.504
_exptl_absorpt_coefficient_mu    1.688
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.64589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14417
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.613
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4614
_reflns_number_total             4738
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4738
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.162
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0229P)²+0.4738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0805
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
I1 I 0.74969(2) 0.66037(2) 0.14159(2) 0.03070(8) Uani 1 1 d . . . . .
Cl1 Cl 0.73448(12) 0.00280(9) -0.07200(8) 0.0554(2) Uani 1 1 d . . . . .
O1 O 0.9888(2) 0.1948(2) 0.38409(17) 0.0340(5) Uani 1 1 d . . . . .
N1 N 0.8024(3) 0.0690(2) 0.3709(2) 0.0278(5) Uani 1 1 d . . . . .
C1 C 0.7284(3) 0.3053(3) 0.4193(2) 0.0223(5) Uani 1 1 d . . . . .
C2 C 0.8593(3) 0.1859(3) 0.3890(2) 0.0266(6) Uani 1 1 d . . . . .
C3 C 0.8927(4) -0.0630(3) 0.3406(3) 0.0385(7) Uani 1 1 d . . . . .
H3A H 0.867274 -0.080302 0.266278 0.058 Uiso 1 1 calc GR . . . .
H3B H 0.875024 -0.143267 0.395672 0.058 Uiso 1 1 calc GR . . . .
H3C H 0.996731 -0.054516 0.339506 0.058 Uiso 1 1 calc GR . . . .
C4 C 0.6478(3) 0.0978(3) 0.3742(2) 0.0248(5) Uani 1 1 d . . . . .
C5 C 0.5535(3) 0.0108(3) 0.3483(2) 0.0303(6) Uani 1 1 d . . . . .
H5 H 0.589485 -0.082765 0.327929 0.036 Uiso 1 1 calc R . . . .
C6 C 0.4038(3) 0.0660(3) 0.3532(2) 0.0328(6) Uani 1 1 d . . . . .
H6 H 0.335859 0.009099 0.335772 0.039 Uiso 1 1 calc R . . . .
C7 C 0.3515(3) 0.2024(3) 0.3831(2) 0.0315(6) Uani 1 1 d . . . . .
H7 H 0.248526 0.237329 0.386455 0.038 Uiso 1 1 calc R . . . .
C8 C 0.4483(3) 0.2885(3) 0.4083(2) 0.0263(6) Uani 1 1 d . . . . .
H8 H 0.412357 0.382075 0.428490 0.032 Uiso 1 1 calc R . . . .
C9 C 0.5977(3) 0.2355(3) 0.4033(2) 0.0235(5) Uani 1 1 d . . . . .
C10 C 0.7315(3) 0.4444(3) 0.3411(2) 0.0237(5) Uani 1 1 d . . . . .
H10 H 0.726211 0.530105 0.374919 0.028 Uiso 1 1 calc R . . . .
C11 C 0.7410(3) 0.4548(3) 0.2308(2) 0.0249(5) Uani 1 1 d . . . . .
C12 C 0.7422(3) 0.3400(3) 0.1575(2) 0.0257(6) Uani 1 1 d . . . . .
C13 C 0.6095(3) 0.3042(3) 0.1324(2) 0.0335(6) Uani 1 1 d . . . . .
H13 H 0.519742 0.351707 0.163554 0.040 Uiso 1 1 calc R . . . .
C14 C 0.6072(4) 0.1996(3) 0.0624(3) 0.0369(7) Uani 1 1 d . . . . .
H14 H 0.516645 0.174957 0.045654 0.044 Uiso 1 1 calc R . . . .
C15 C 0.7374(4) 0.1325(3) 0.0179(3) 0.0370(7) Uani 1 1 d . . . . .
C16 C 0.8709(4) 0.1666(3) 0.0401(3) 0.0418(8) Uani 1 1 d . . . . .
H16 H 0.959863 0.119914 0.007384 0.050 Uiso 1 1 calc R . . . .
C17 C 0.8726(3) 0.2706(3) 0.1113(3) 0.0333(6) Uani 1 1 d . . . . .
H17 H 0.963571 0.294134 0.128293 0.040 Uiso 1 1 calc R . . . .
C18 C 0.7464(3) 0.3358(3) 0.5396(2) 0.0220(5) Uani 1 1 d . . . . .
C19 C 0.6464(3) 0.3121(3) 0.6271(2) 0.0258(5) Uani 1 1 d . . . . .
H19 H 0.566445 0.266342 0.615887 0.031 Uiso 1 1 calc R . . . .
C20 C 0.6625(3) 0.3551(3) 0.7313(2) 0.0297(6) Uani 1 1 d . . . . .
H20 H 0.593877 0.336578 0.790672 0.036 Uiso 1 1 calc R . . . .
C21 C 0.7769(3) 0.4245(3) 0.7505(2) 0.0259(6) Uani 1 1 d . . . . .
C22 C 0.8807(3) 0.4415(3) 0.6632(2) 0.0279(6) Uani 1 1 d . . . . .
H22 H 0.962678 0.484161 0.675035 0.033 Uiso 1 1 calc R . . . .
C23 C 0.8666(3) 0.3973(3) 0.5600(2) 0.0262(6) Uani 1 1 d . . . . .
H23 H 0.939419 0.408921 0.502311 0.031 Uiso 1 1 calc R . . . .
C24 C 0.7867(3) 0.4867(3) 0.8577(2) 0.0360(7) Uani 1 1 d . . . . .
H24A H 0.769129 0.591637 0.843457 0.054 Uiso 1 1 calc GR . . . .
H24B H 0.884933 0.452523 0.887341 0.054 Uiso 1 1 calc GR . . . .
H24C H 0.712539 0.456367 0.912395 0.054 Uiso 1 1 calc GR . . . .


_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
I1 C11 2.130(3) . ?
Cl1 C15 1.747(3) . ?
O1 C2 1.214(3) . ?
N1 C2 1.363(3) . ?
N1 C3 1.452(3) . ?
N1 C4 1.405(3) . ?
C1 C2 1.562(4) . ?
C1 C9 1.515(3) . ?
C1 C10 1.533(3) . ?
C1 C18 1.538(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.383(4) . ?
C4 C9 1.391(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.319(4) . ?
C11 C12 1.488(4) . ?
C12 C13 1.393(4) . ?
C12 C17 1.386(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.369(5) . ?
C15 C16 1.383(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(4) . ?
C18 C23 1.396(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.392(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.391(4) . ?
C21 C22 1.396(4) . ?
C21 C24 1.500(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.382(4) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C3 123.1(2) . . ?
C2 N1 C4 111.7(2) . . ?
C4 N1 C3 125.0(2) . . ?
C9 C1 C2 101.2(2) . . ?
C9 C1 C10 113.4(2) . . ?
C9 C1 C18 115.2(2) . . ?
C10 C1 C2 110.5(2) . . ?
C10 C1 C18 108.1(2) . . ?
C18 C1 C2 108.1(2) . . ?
O1 C2 N1 126.0(3) . . ?
O1 C2 C1 126.1(2) . . ?
N1 C2 C1 107.8(2) . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 N1 127.8(2) . . ?
C5 C4 C9 122.5(3) . . ?
C9 C4 N1 109.7(2) . . ?
C4 C5 H5 121.4 . . ?
C4 C5 C6 117.1(3) . . ?
C6 C5 H5 121.4 . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.3(3) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.8(3) . . ?
C9 C8 H8 120.6 . . ?
C4 C9 C1 109.3(2) . . ?
C8 C9 C1 131.0(2) . . ?
C8 C9 C4 119.6(2) . . ?
C1 C10 H10 117.3 . . ?
C11 C10 C1 125.4(2) . . ?
C11 C10 H10 117.3 . . ?
C10 C11 I1 117.93(19) . . ?
C10 C11 C12 128.1(2) . . ?
C12 C11 I1 113.90(18) . . ?
C13 C12 C11 119.4(3) . . ?
C17 C12 C11 121.3(3) . . ?
C17 C12 C13 119.3(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 Cl1 119.1(2) . . ?
C14 C15 C16 121.9(3) . . ?
C16 C15 Cl1 119.0(3) . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.9(3) . . ?
C17 C16 H16 120.6 . . ?
C12 C17 C16 120.3(3) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C1 123.6(2) . . ?
C19 C18 C23 118.5(2) . . ?
C23 C18 C1 117.8(2) . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.5(3) . . ?
C21 C20 H20 119.2 . . ?
C20 C21 C22 117.4(3) . . ?
C20 C21 C24 122.4(3) . . ?
C22 C21 C24 120.1(3) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.3(3) . . ?
C23 C22 H22 119.4 . . ?
C18 C23 H23 119.6 . . ?
C22 C23 C18 120.7(3) . . ?
C22 C23 H23 119.6 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1564095'
_audit_update_record             
;
2017-07-23 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;
_audit_creation_date             2017-07-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H28 N2 O2, C H2 Cl2'
_chemical_formula_sum            'C33 H30 Cl2 N2 O2'
_chemical_formula_weight         557.49
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.690(2)
_cell_length_b                   28.425(6)
_cell_length_c                   9.586(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.155(3)
_cell_angle_gamma                90
_cell_volume                     2716.5(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8618
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4694
_cell_measurement_theta_min      1.4328
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.89837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21395
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.469
_diffrn_reflns_theta_min         2.165
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5628
_reflns_number_total             6213
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         6213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0541
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+1.7612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1278
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15),
 C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C28(H28), C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C32(H32A,H32B,H32C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.48690(13) 0.69681(4) 0.38623(14) 0.0262(3) Uani 1 1 d . . . . .
O2 O 0.41460(13) 0.67336(4) 0.01592(15) 0.0296(3) Uani 1 1 d . . . . .
N1 N 0.61452(15) 0.73382(5) 0.27137(16) 0.0230(3) Uani 1 1 d . . . . .
N2 N 0.47686(15) 0.60374(5) -0.06222(17) 0.0260(3) Uani 1 1 d . . . . .
C1 C 0.64461(16) 0.65133(6) 0.29985(19) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.56859(17) 0.69568(6) 0.32478(19) 0.0219(3) Uani 1 1 d . . . . .
C3 C 0.5627(2) 0.78106(6) 0.2708(2) 0.0289(4) Uani 1 1 d . . . . .
H3A H 0.516076 0.791334 0.167348 0.043 Uiso 1 1 calc GR . . . .
H3B H 0.637161 0.802570 0.320491 0.043 Uiso 1 1 calc GR . . . .
H3C H 0.499913 0.781178 0.324184 0.043 Uiso 1 1 calc GR . . . .
C4 C 0.70772(17) 0.72119(6) 0.20612(19) 0.0225(3) Uani 1 1 d . . . . .
C5 C 0.77447(18) 0.75089(6) 0.1423(2) 0.0271(4) Uani 1 1 d . . . . .
H5 H 0.761821 0.783994 0.140727 0.033 Uiso 1 1 calc R . . . .
C6 C 0.86103(19) 0.73043(7) 0.0805(2) 0.0288(4) Uani 1 1 d . . . . .
H6 H 0.908394 0.749924 0.035921 0.035 Uiso 1 1 calc R . . . .
C7 C 0.87920(18) 0.68213(7) 0.0830(2) 0.0286(4) Uani 1 1 d . . . . .
H7 H 0.936867 0.668835 0.037843 0.034 Uiso 1 1 calc R . . . .
C8 C 0.81298(18) 0.65271(6) 0.1517(2) 0.0254(4) Uani 1 1 d . . . . .
H8 H 0.826718 0.619646 0.154886 0.031 Uiso 1 1 calc R . . . .
C9 C 0.72730(17) 0.67251(6) 0.21478(19) 0.0215(3) Uani 1 1 d . . . . .
C10 C 0.73130(17) 0.63227(6) 0.45507(19) 0.0210(3) Uani 1 1 d . . . . .
C11 C 0.86999(18) 0.62748(7) 0.4987(2) 0.0269(4) Uani 1 1 d . . . . .
H11 H 0.913018 0.636681 0.431909 0.032 Uiso 1 1 calc R . . . .
C12 C 0.94644(19) 0.60942(7) 0.6386(2) 0.0308(4) Uani 1 1 d . . . . .
H12 H 1.040680 0.606335 0.665018 0.037 Uiso 1 1 calc R . . . .
C13 C 0.8883(2) 0.59582(7) 0.7403(2) 0.0293(4) Uani 1 1 d . . . . .
C14 C 0.75070(19) 0.60221(6) 0.6987(2) 0.0281(4) Uani 1 1 d . . . . .
H14 H 0.708616 0.594064 0.767331 0.034 Uiso 1 1 calc R . . . .
C15 C 0.67295(18) 0.62019(6) 0.55941(19) 0.0241(4) Uani 1 1 d . . . . .
H15 H 0.579238 0.624326 0.534845 0.029 Uiso 1 1 calc R . . . .
C16 C 0.9709(2) 0.57486(8) 0.8901(2) 0.0420(5) Uani 1 1 d . . . . .
H16A H 0.981057 0.540961 0.878843 0.063 Uiso 1 1 calc GR . . . .
H16B H 0.925737 0.580308 0.961210 0.063 Uiso 1 1 calc GR . . . .
H16C H 1.059619 0.589728 0.927325 0.063 Uiso 1 1 calc GR . . . .
C17 C 0.54292(17) 0.61331(6) 0.19992(19) 0.0205(3) Uani 1 1 d . . . . .
C18 C 0.46994(17) 0.63528(6) 0.0427(2) 0.0237(4) Uani 1 1 d . . . . .
C19 C 0.4087(2) 0.61043(7) -0.2231(2) 0.0323(4) Uani 1 1 d . . . . .
H19A H 0.345492 0.636708 -0.240977 0.048 Uiso 1 1 calc GR . . . .
H19B H 0.359836 0.581692 -0.267383 0.048 Uiso 1 1 calc GR . . . .
H19C H 0.475111 0.617385 -0.268909 0.048 Uiso 1 1 calc GR . . . .
C20 C 0.56640(17) 0.56745(6) 0.0043(2) 0.0237(4) Uani 1 1 d . . . . .
C21 C 0.6096(2) 0.53210(6) -0.0669(2) 0.0293(4) Uani 1 1 d . . . . .
H21 H 0.575093 0.529244 -0.172804 0.035 Uiso 1 1 calc R . . . .
C22 C 0.70542(19) 0.50091(6) 0.0224(2) 0.0302(4) Uani 1 1 d . . . . .
H22 H 0.737433 0.476427 -0.023337 0.036 Uiso 1 1 calc R . . . .
C23 C 0.75485(18) 0.50485(6) 0.1762(2) 0.0286(4) Uani 1 1 d . . . . .
H23 H 0.820757 0.483243 0.234663 0.034 Uiso 1 1 calc R . . . .
C24 C 0.70880(17) 0.54049(6) 0.2475(2) 0.0255(4) Uani 1 1 d . . . . .
H24 H 0.742471 0.543000 0.353436 0.031 Uiso 1 1 calc R . . . .
C25 C 0.61391(17) 0.57169(6) 0.1607(2) 0.0224(3) Uani 1 1 d . . . . .
C26 C 0.43205(17) 0.59626(6) 0.25674(19) 0.0214(3) Uani 1 1 d . . . . .
C27 C 0.44535(18) 0.55391(6) 0.3338(2) 0.0256(4) Uani 1 1 d . . . . .
H27 H 0.525850 0.536312 0.356739 0.031 Uiso 1 1 calc R . . . .
C28 C 0.34347(19) 0.53679(7) 0.3778(2) 0.0283(4) Uani 1 1 d . . . . .
H28 H 0.355529 0.507745 0.430071 0.034 Uiso 1 1 calc R . . . .
C29 C 0.22449(18) 0.56146(7) 0.3467(2) 0.0286(4) Uani 1 1 d . . . . .
C30 C 0.21146(18) 0.60397(7) 0.2712(2) 0.0294(4) Uani 1 1 d . . . . .
H30 H 0.131471 0.621750 0.250051 0.035 Uiso 1 1 calc R . . . .
C31 C 0.31221(18) 0.62109(6) 0.2260(2) 0.0267(4) Uani 1 1 d . . . . .
H31 H 0.299647 0.650094 0.173457 0.032 Uiso 1 1 calc R . . . .
C32 C 0.1128(2) 0.54252(8) 0.3927(3) 0.0411(5) Uani 1 1 d . . . . .
H32A H 0.117790 0.508096 0.397433 0.062 Uiso 1 1 calc GR . . . .
H32B H 0.025982 0.552125 0.319147 0.062 Uiso 1 1 calc GR . . . .
H32C H 0.122258 0.555058 0.491192 0.062 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.10531(6) 0.79551(2) 0.37013(8) 0.05100(17) Uani 1 1 d . . . . .
Cl2 Cl 0.17307(8) 0.70434(3) 0.51670(9) 0.0649(2) Uani 1 1 d . . . . .
C33 C 0.2014(2) 0.74419(9) 0.3897(3) 0.0468(6) Uani 1 1 d . . . . .
H33A H 0.297715 0.752634 0.425726 0.056 Uiso 1 1 calc R . . . .
H33B H 0.178409 0.728814 0.290961 0.056 Uiso 1 1 calc R . . . .


_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 1.217(2) . ?
O2 C18 1.216(2) . ?
N1 C2 1.364(2) . ?
N1 C3 1.452(2) . ?
N1 C4 1.401(2) . ?
N2 C18 1.369(2) . ?
N2 C19 1.461(2) . ?
N2 C20 1.395(2) . ?
C1 C2 1.564(2) . ?
C1 C9 1.526(2) . ?
C1 C10 1.540(2) . ?
C1 C17 1.586(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.382(2) . ?
C4 C9 1.397(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.404(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.386(2) . ?
C10 C11 1.394(2) . ?
C10 C15 1.399(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(3) . ?
C13 C14 1.390(3) . ?
C13 C16 1.510(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(3) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.556(2) . ?
C17 C25 1.524(2) . ?
C17 C26 1.550(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.384(3) . ?
C20 C25 1.404(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.391(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.379(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.406(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.378(3) . ?
C26 C27 1.392(2) . ?
C26 C31 1.398(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.390(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.387(3) . ?
C29 C30 1.389(3) . ?
C29 C32 1.513(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.386(3) . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
Cl1 C33 1.755(2) . ?
Cl2 C33 1.767(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?

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 C3 123.24(15) . . ?
C2 N1 C4 111.99(14) . . ?
C4 N1 C3 124.55(15) . . ?
C18 N2 C19 123.48(16) . . ?
C18 N2 C20 111.02(15) . . ?
C20 N2 C19 125.25(16) . . ?
C2 C1 C17 111.15(13) . . ?
C9 C1 C2 101.35(13) . . ?
C9 C1 C10 113.11(14) . . ?
C9 C1 C17 110.43(13) . . ?
C10 C1 C2 107.50(13) . . ?
C10 C1 C17 112.71(13) . . ?
O1 C2 N1 125.39(16) . . ?
O1 C2 C1 126.73(15) . . ?
N1 C2 C1 107.82(14) . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 N1 127.23(16) . . ?
C5 C4 C9 122.74(16) . . ?
C9 C4 N1 110.03(15) . . ?
C4 C5 H5 121.3 . . ?
C4 C5 C6 117.47(17) . . ?
C6 C5 H5 121.3 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.13(17) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.46(17) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.16(17) . . ?
C9 C8 H8 120.4 . . ?
C4 C9 C1 108.62(14) . . ?
C8 C9 C1 132.40(16) . . ?
C8 C9 C4 118.98(16) . . ?
C11 C10 C1 121.88(15) . . ?
C11 C10 C15 117.50(16) . . ?
C15 C10 C1 120.60(15) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.05(17) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.58(18) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 C14 117.28(17) . . ?
C12 C13 C16 121.44(19) . . ?
C14 C13 C16 121.28(18) . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.82(17) . . ?
C15 C14 H14 119.1 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.69(17) . . ?
C14 C15 H15 119.7 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C1 107.84(13) . . ?
C25 C17 C1 112.59(13) . . ?
C25 C17 C18 101.10(13) . . ?
C25 C17 C26 110.85(13) . . ?
C26 C17 C1 116.44(13) . . ?
C26 C17 C18 106.64(13) . . ?
O2 C18 N2 125.40(17) . . ?
O2 C18 C17 126.67(16) . . ?
N2 C18 C17 107.92(14) . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C25 110.41(15) . . ?
C21 C20 N2 127.39(17) . . ?
C21 C20 C25 122.17(17) . . ?
C20 C21 H21 121.3 . . ?
C20 C21 C22 117.47(18) . . ?
C22 C21 H21 121.3 . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.29(17) . . ?
C23 C22 H22 119.4 . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.75(17) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 120.6 . . ?
C25 C24 C23 118.73(18) . . ?
C25 C24 H24 120.6 . . ?
C20 C25 C17 108.05(15) . . ?
C24 C25 C17 132.38(16) . . ?
C24 C25 C20 119.57(16) . . ?
C27 C26 C17 120.81(15) . . ?
C27 C26 C31 117.31(16) . . ?
C31 C26 C17 121.79(15) . . ?
C26 C27 H27 119.3 . . ?
C28 C27 C26 121.49(17) . . ?
C28 C27 H27 119.3 . . ?
C27 C28 H28 119.5 . . ?
C29 C28 C27 121.04(17) . . ?
C29 C28 H28 119.5 . . ?
C28 C29 C30 117.61(17) . . ?
C28 C29 C32 121.07(18) . . ?
C30 C29 C32 121.32(18) . . ?
C29 C30 H30 119.2 . . ?
C31 C30 C29 121.67(17) . . ?
C31 C30 H30 119.2 . . ?
C26 C31 H31 119.6 . . ?
C30 C31 C26 120.87(17) . . ?
C30 C31 H31 119.6 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
Cl1 C33 Cl2 111.56(13) . . ?
Cl1 C33 H33A 109.3 . . ?
Cl1 C33 H33B 109.3 . . ?
Cl2 C33 H33A 109.3 . . ?
Cl2 C33 H33B 109.3 . . ?
H33A C33 H33B 108.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
