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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1433180'
_audit_update_record             
;
2015-10-26 deposited with the CCDC.
2016-05-16 downloaded from the CCDC.
;
_audit_creation_date             2014-09-28
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H18 N2 O3'
_chemical_formula_sum            'C19 H18 N2 O3'
_chemical_formula_weight         322.35
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H20 O3 N2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x+1/2, z+3/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+1/4'
'x+1/2, -y+1/2, -z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   9.37666(19)
_cell_length_b                   9.37666(19)
_cell_length_c                   36.6305(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3220.62(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2261
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      65.5110
_cell_measurement_theta_min      4.8390
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.939
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            5710
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         65.529
_diffrn_reflns_theta_min         4.829
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9370
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -60.00   33.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7931   57.0000 -120.0000 93

#__ type_ start__ end____ width___ exp.time_
  2 omega   47.00   81.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.9350  -30.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
  3 omega  101.00  162.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.9350  125.0000  -90.0000 61

#__ type_ start__ end____ width___ exp.time_
  4 omega   62.00  159.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.9350   30.0000  -90.0000 97
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0022823000
_diffrn_orient_matrix_UB_12      0.0846279000
_diffrn_orient_matrix_UB_13      0.0360541000
_diffrn_orient_matrix_UB_21      -0.0533230000
_diffrn_orient_matrix_UB_22      -0.1338542000
_diffrn_orient_matrix_UB_23      0.0202672000
_diffrn_orient_matrix_UB_31      0.1551892000
_diffrn_orient_matrix_UB_32      -0.0446541000
_diffrn_orient_matrix_UB_33      0.0075538000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.541
_reflns_Friedel_fraction_full    0.812
_reflns_Friedel_fraction_max     0.860
_reflns_number_gt                2382
_reflns_number_total             2598
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 816 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2598
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+0.5727P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1052
_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 Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.e :
 C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
C1 C 0.4278(3) 0.7274(3) 0.05314(8) 0.0264(6) Uani 1 1 d . . . . .
C2 C 0.4777(3) 0.8387(3) 0.03260(7) 0.0238(6) Uani 1 1 d . . . . .
C3 C 0.3876(3) 0.9313(3) 0.00865(7) 0.0231(6) Uani 1 1 d . . . . .
C4 C 0.4296(3) 0.9426(3) -0.03183(7) 0.0240(6) Uani 1 1 d . . . . .
H4A H 0.4979 1.0215 -0.0360 0.029 Uiso 1 1 calc R U . . .
H4B H 0.4717 0.8524 -0.0408 0.029 Uiso 1 1 calc R U . . .
C5 C 0.2864(3) 0.9729(3) -0.04994(8) 0.0260(6) Uani 1 1 d . . . . .
H5 H 0.2640 1.0761 -0.0462 0.031 Uiso 1 1 calc R U . . .
C6 C 0.1840(3) 0.8865(3) -0.02655(8) 0.0270(6) Uani 1 1 d . . . . .
C7 C 0.1801(3) 0.7970(4) 0.03766(8) 0.0328(7) Uani 1 1 d . . . . .
H7A H 0.0869 0.7561 0.0305 0.039 Uiso 1 1 calc R U . . .
H7B H 0.1629 0.8693 0.0569 0.039 Uiso 1 1 calc R U . . .
C8 C 0.2755(3) 0.6791(4) 0.05280(9) 0.0329(7) Uani 1 1 d . . . . .
H8A H 0.2451 0.6547 0.0779 0.039 Uiso 1 1 calc R U . . .
H8B H 0.2662 0.5926 0.0375 0.039 Uiso 1 1 calc R U . . .
C9 C 0.5463(3) 0.6761(3) 0.07408(7) 0.0270(6) Uani 1 1 d . . . . .
C10 C 0.5625(4) 0.5700(4) 0.10070(8) 0.0354(8) Uani 1 1 d . . . . .
H10 H 0.4849 0.5097 0.1070 0.042 Uiso 1 1 calc R U . . .
C11 C 0.6933(4) 0.5546(4) 0.11756(8) 0.0399(8) Uani 1 1 d . . . . .
H11 H 0.7053 0.4827 0.1356 0.048 Uiso 1 1 calc R U . . .
C12 C 0.8087(4) 0.6428(4) 0.10859(9) 0.0387(8) Uani 1 1 d . . . . .
H12 H 0.8970 0.6302 0.1209 0.046 Uiso 1 1 calc R U . . .
C13 C 0.7971(3) 0.7481(3) 0.08223(8) 0.0311(7) Uani 1 1 d . . . . .
H13 H 0.8754 0.8078 0.0761 0.037 Uiso 1 1 calc R U . . .
C14 C 0.6654(3) 0.7624(3) 0.06506(8) 0.0263(6) Uani 1 1 d . . . . .
C15 C 0.3752(3) 1.0797(3) 0.02651(8) 0.0269(6) Uani 1 1 d . . . . .
C16 C 0.5029(4) 1.2900(3) 0.04108(10) 0.0428(9) Uani 1 1 d . . . . .
H16A H 0.4186 1.3461 0.0344 0.064 Uiso 1 1 calc R U . . .
H16B H 0.5892 1.3406 0.0333 0.064 Uiso 1 1 calc R U . . .
H16C H 0.5049 1.2766 0.0676 0.064 Uiso 1 1 calc R U . . .
C17 C 0.2717(4) 0.9410(4) -0.09062(8) 0.0334(7) Uani 1 1 d . . . . .
H17A H 0.3064 0.8432 -0.0955 0.040 Uiso 1 1 calc R U . . .
H17B H 0.1697 0.9452 -0.0975 0.040 Uiso 1 1 calc R U . . .
C18 C 0.3524(4) 1.0424(4) -0.11312(8) 0.0363(7) Uani 1 1 d . . . . .
C19 C 0.4175(4) 1.1239(4) -0.13145(9) 0.0463(9) Uani 1 1 d . . . . .
H19 H 0.4696 1.1892 -0.1461 0.056 Uiso 1 1 calc R U . . .
N1 N 0.2461(3) 0.8648(3) 0.00620(6) 0.0266(5) Uani 1 1 d . . . . .
N2 N 0.6212(3) 0.8604(3) 0.03918(6) 0.0249(5) Uani 1 1 d . . . . .
O1 O 0.0651(2) 0.8441(2) -0.03584(6) 0.0357(5) Uani 1 1 d . . . . .
O2 O 0.4967(2) 1.1524(2) 0.02328(6) 0.0360(5) Uani 1 1 d . . . . .
O3 O 0.2726(3) 1.1215(3) 0.04285(9) 0.0554(7) Uani 1 1 d . . . . .
H1 H 0.673(4) 0.933(5) 0.0311(10) 0.048(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.370(4) . ?
C1 C8 1.497(4) . ?
C1 C9 1.433(4) . ?
C2 C3 1.495(4) . ?
C2 N2 1.382(4) . ?
C3 C4 1.538(4) . ?
C3 C15 1.542(4) . ?
C3 N1 1.469(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.524(4) . ?
C5 H5 1.0000 . ?
C5 C6 1.521(4) . ?
C5 C17 1.526(4) . ?
C6 N1 1.349(4) . ?
C6 O1 1.231(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.526(5) . ?
C7 N1 1.454(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.402(4) . ?
C9 C14 1.418(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.402(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.392(4) . ?
C14 N2 1.384(4) . ?
C15 O2 1.333(4) . ?
C15 O3 1.198(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 O2 1.447(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.468(5) . ?
C18 C19 1.186(5) . ?
C19 H19 0.9500 . ?
N2 H1 0.89(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C8 123.5(3) . . ?
C2 C1 C9 106.5(2) . . ?
C9 C1 C8 130.0(3) . . ?
C1 C2 C3 124.9(3) . . ?
C1 C2 N2 110.5(2) . . ?
N2 C2 C3 124.5(3) . . ?
C2 C3 C4 117.5(2) . . ?
C2 C3 C15 108.5(2) . . ?
C4 C3 C15 111.5(2) . . ?
N1 C3 C2 107.4(2) . . ?
N1 C3 C4 101.6(2) . . ?
N1 C3 C15 109.9(2) . . ?
C3 C4 H4A 111.4 . . ?
C3 C4 H4B 111.4 . . ?
H4A C4 H4B 109.2 . . ?
C5 C4 C3 101.9(2) . . ?
C5 C4 H4A 111.4 . . ?
C5 C4 H4B 111.4 . . ?
C4 C5 H5 107.8 . . ?
C4 C5 C17 117.9(3) . . ?
C6 C5 C4 102.3(2) . . ?
C6 C5 H5 107.8 . . ?
C6 C5 C17 112.9(2) . . ?
C17 C5 H5 107.8 . . ?
N1 C6 C5 108.0(2) . . ?
O1 C6 C5 126.0(3) . . ?
O1 C6 N1 126.0(3) . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 C8 110.8(3) . . ?
C1 C8 C7 110.1(3) . . ?
C1 C8 H8A 109.6 . . ?
C1 C8 H8B 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C1 134.0(3) . . ?
C10 C9 C14 118.8(3) . . ?
C14 C9 C1 107.1(3) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 C9 118.8(3) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.3(3) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.6(3) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 121.5 . . ?
C12 C13 C14 117.0(3) . . ?
C14 C13 H13 121.5 . . ?
C13 C14 C9 122.5(3) . . ?
N2 C14 C9 107.6(3) . . ?
N2 C14 C13 129.7(3) . . ?
O2 C15 C3 111.0(2) . . ?
O3 C15 C3 124.6(3) . . ?
O3 C15 O2 124.3(3) . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
C5 C17 H17A 109.2 . . ?
C5 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 C5 112.0(3) . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C19 C18 C17 179.7(4) . . ?
C18 C19 H19 180.0 . . ?
C6 N1 C3 112.4(2) . . ?
C6 N1 C7 125.9(2) . . ?
C7 N1 C3 121.4(2) . . ?
C2 N2 C14 108.2(2) . . ?
C2 N2 H1 126(3) . . ?
C14 N2 H1 125(3) . . ?
C15 O2 C16 116.7(3) . . ?

_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.866
_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.
;
_shelxl_version_number           2013-3
_exptl_crystal_colour            white
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM MeOH'
####################################################################### 
# 
# 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_exp_5207
_database_code_depnum_ccdc_archive 'CCDC 1433182'
_audit_update_record             
;
2015-10-26 deposited with the CCDC.
2016-05-16 downloaded from the CCDC.
;
_audit_creation_date             2015-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C H Cl3, 2(C19 H24 N2)'
_chemical_formula_sum            'C39 H49 Cl3 N4'
_chemical_formula_weight         680.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H10 N2'
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'
Cl Cl 0.1484 0.1585 '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                   13.0230(11)
_cell_length_b                   21.0779(16)
_cell_length_c                   12.8028(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.541(8)
_cell_angle_gamma                90
_cell_volume                     3514.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3295
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      27.8940
_cell_measurement_theta_min      3.2870
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_Laue_measured_fraction_full 0.930
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12429
_diffrn_reflns_point_group_measured_fraction_full 0.930
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.129
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.930
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -54.00   36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -57.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega  -81.00    0.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -57.0000  -90.0000 81
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0125775000
_diffrn_orient_matrix_UB_12      -0.0321887000
_diffrn_orient_matrix_UB_13      0.0099332000
_diffrn_orient_matrix_UB_21      -0.0525650000
_diffrn_orient_matrix_UB_22      -0.0068573000
_diffrn_orient_matrix_UB_23      0.0087522000
_diffrn_orient_matrix_UB_31      -0.0067364000
_diffrn_orient_matrix_UB_32      -0.0070122000
_diffrn_orient_matrix_UB_33      -0.0538028000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3872
_reflns_number_total             5920
_reflns_odcompleteness_completeness 99.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.764
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         5920
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1306
_refine_ls_R_factor_gt           0.0896
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1042P)²+3.0406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2077
_refine_ls_wR_factor_ref         0.2393
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C39(H39), C31(H31), C35(H35), C12(H12), C11(H11), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C28(H28A,H28B), C34(H34A,H34B), C37(H37A,H37B), C36(H36A,
 H36B), C33(H33A,H33B), C9(H9A,H9B), C18(H18A,H18B), C16(H16A,H16B), C15(H15A,
 H15B), C14(H14A,H14B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C23(H23), C22(H22), C24(H24), C21(H21), N1(H1), C4(H4), C5(H5),
 C3(H3A), C2(H2)
2.d Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Cl3 Cl 0.13453(13) 0.48946(8) 0.31241(14) 0.0758(5) Uani 1 1 d . . . . .
Cl2 Cl 0.24518(15) 0.45005(9) 0.12899(13) 0.0774(6) Uani 1 1 d . . . . .
Cl1 Cl 0.33252(18) 0.54136(13) 0.26923(18) 0.1083(8) Uani 1 1 d . . . . .
C39 C 0.2167(5) 0.5130(3) 0.2130(5) 0.0586(15) Uani 1 1 d . . . . .
H39 H 0.1835 0.5479 0.1719 0.070 Uiso 1 1 calc R . . . .
N3 N 0.0785(3) 0.68554(16) 0.2154(3) 0.0272(8) Uani 1 1 d . . . . .
H3 H 0.0975 0.7113 0.2661 0.033 Uiso 1 1 calc R . . . .
N4 N 0.1545(3) 0.73632(16) -0.1142(3) 0.0269(8) Uani 1 1 d . . . . .
C32 C 0.1134(3) 0.68756(19) 0.1130(3) 0.0265(9) Uani 1 1 d . . . . .
C31 C 0.1859(3) 0.7390(2) 0.0806(3) 0.0262(9) Uani 1 1 d . . . . .
H31 H 0.1911 0.7703 0.1391 0.031 Uiso 1 1 calc R . . . .
C25 C 0.0008(3) 0.60676(19) 0.1248(3) 0.0282(9) Uani 1 1 d . . . . .
C26 C 0.0670(3) 0.6400(2) 0.0552(3) 0.0285(9) Uani 1 1 d . . . . .
C20 C 0.0088(3) 0.63630(19) 0.2240(3) 0.0264(9) Uani 1 1 d . . . . .
C29 C 0.1476(4) 0.7744(2) -0.0170(3) 0.0259(9) Uani 1 1 d . . . . .
C30 C 0.3320(4) 0.7427(2) -0.0468(3) 0.0334(10) Uani 1 1 d . . . . .
C27 C 0.0852(4) 0.6269(2) -0.0581(3) 0.0354(11) Uani 1 1 d . . . . .
H27A H 0.0340 0.5954 -0.0827 0.043 Uiso 1 1 calc R . . . .
H27B H 0.1541 0.6076 -0.0655 0.043 Uiso 1 1 calc R . . . .
C23 C -0.1208(4) 0.5349(2) 0.1989(4) 0.0378(11) Uani 1 1 d . . . . .
H23 H -0.1644 0.4990 0.1923 0.045 Uiso 1 1 calc R . . . .
C28 C 0.0788(3) 0.6854(2) -0.1284(3) 0.0306(10) Uani 1 1 d . . . . .
H28A H 0.0831 0.6707 -0.2016 0.037 Uiso 1 1 calc R . . . .
H28B H 0.0098 0.7043 -0.1196 0.037 Uiso 1 1 calc R . . . .
C22 C -0.1139(4) 0.5664(2) 0.2950(4) 0.0389(11) Uani 1 1 d . . . . .
H22 H -0.1548 0.5525 0.3517 0.047 Uiso 1 1 calc R . . . .
C24 C -0.0661(4) 0.5548(2) 0.1145(4) 0.0336(10) Uani 1 1 d . . . . .
H24 H -0.0732 0.5336 0.0493 0.040 Uiso 1 1 calc R . . . .
C34 C 0.2961(3) 0.7149(2) 0.0566(3) 0.0347(10) Uani 1 1 d . . . . .
H34A H 0.3437 0.7278 0.1134 0.042 Uiso 1 1 calc R . . . .
H34B H 0.2961 0.6680 0.0525 0.042 Uiso 1 1 calc R . . . .
C37 C 0.1990(4) 0.8849(2) 0.0533(4) 0.0385(11) Uani 1 1 d . . . . .
H37A H 0.2288 0.8677 0.1189 0.046 Uiso 1 1 calc R . . . .
H37B H 0.2399 0.9226 0.0338 0.046 Uiso 1 1 calc R . . . .
C35 C 0.2104(3) 0.8347(2) -0.0326(3) 0.0313(10) Uani 1 1 d . . . . .
H35 H 0.1881 0.8543 -0.1003 0.038 Uiso 1 1 calc R . . . .
C21 C -0.0484(3) 0.61755(19) 0.3087(3) 0.0299(10) Uani 1 1 d . . . . .
H21 H -0.0430 0.6389 0.3739 0.036 Uiso 1 1 calc R . . . .
C36 C 0.3244(3) 0.8147(2) -0.0431(4) 0.0389(11) Uani 1 1 d . . . . .
H36A H 0.3532 0.8329 -0.1078 0.047 Uiso 1 1 calc R . . . .
H36B H 0.3646 0.8310 0.0170 0.047 Uiso 1 1 calc R . . . .
C33 C 0.2621(3) 0.7171(2) -0.1324(3) 0.0380(11) Uani 1 1 d . . . . .
H33A H 0.2848 0.7335 -0.2008 0.046 Uiso 1 1 calc R . . . .
H33B H 0.2668 0.6703 -0.1341 0.046 Uiso 1 1 calc R . . . .
C38 C 0.0895(4) 0.9059(3) 0.0742(4) 0.0498(13) Uani 1 1 d . . . . .
H38A H 0.0570 0.9194 0.0085 0.075 Uiso 1 1 calc GR . . . .
H38B H 0.0901 0.9413 0.1237 0.075 Uiso 1 1 calc GR . . . .
H38C H 0.0507 0.8704 0.1037 0.075 Uiso 1 1 calc GR . . . .
N1 N 0.4213(3) 0.32122(17) 1.1457(3) 0.0289(8) Uani 1 1 d . . . . .
H1 H 0.4007 0.2986 1.1993 0.035 Uiso 1 1 calc R . . . .
C12 C 0.3179(3) 0.2609(2) 1.0135(3) 0.0269(9) Uani 1 1 d . . . . .
H12 H 0.3134 0.2318 1.0750 0.032 Uiso 1 1 calc R . . . .
N2 N 0.3486(3) 0.25436(17) 0.8211(3) 0.0276(8) Uani 1 1 d . . . . .
C11 C 0.3558(3) 0.2213(2) 0.9216(3) 0.0274(9) Uani 1 1 d . . . . .
H11 H 0.4291 0.2093 0.9348 0.033 Uiso 1 1 calc R . . . .
C13 C 0.3895(3) 0.3130(2) 1.0432(3) 0.0279(9) Uani 1 1 d . . . . .
C4 C 0.6290(4) 0.4666(2) 1.1136(4) 0.0393(12) Uani 1 1 d . . . . .
H4 H 0.6773 0.4996 1.1020 0.047 Uiso 1 1 calc R . . . .
C5 C 0.5753(4) 0.44225(19) 1.0307(4) 0.0329(10) Uani 1 1 d . . . . .
H5 H 0.5856 0.4583 0.9623 0.039 Uiso 1 1 calc R . . . .
C1 C 0.4909(3) 0.3707(2) 1.1504(3) 0.0286(9) Uani 1 1 d . . . . .
C9 C 0.4267(4) 0.3038(2) 0.8013(3) 0.0333(10) Uani 1 1 d . . . . .
H9A H 0.4219 0.3155 0.7265 0.040 Uiso 1 1 calc R . . . .
H9B H 0.4952 0.2845 0.8127 0.040 Uiso 1 1 calc R . . . .
C6 C 0.5050(3) 0.39342(18) 1.0478(3) 0.0270(9) Uani 1 1 d . . . . .
C7 C 0.4375(3) 0.35684(19) 0.9803(3) 0.0284(9) Uani 1 1 d . . . . .
C18 C 0.3041(4) 0.1129(2) 1.0012(4) 0.0399(11) Uani 1 1 d . . . . .
H18A H 0.2817 0.1340 1.0662 0.048 Uiso 1 1 calc R . . . .
H18B H 0.2570 0.0768 0.9884 0.048 Uiso 1 1 calc R . . . .
C16 C 0.1782(4) 0.1800(2) 0.8943(4) 0.0413(12) Uani 1 1 d . . . . .
H16A H 0.1506 0.1597 0.8302 0.050 Uiso 1 1 calc R . . . .
H16B H 0.1366 0.1656 0.9541 0.050 Uiso 1 1 calc R . . . .
C3 C 0.6147(4) 0.4442(2) 1.2152(4) 0.0410(12) Uani 1 1 d . . . . .
H3A H 0.6527 0.4626 1.2712 0.049 Uiso 1 1 calc R . . . .
C17 C 0.2914(4) 0.1599(2) 0.9112(3) 0.0340(10) Uani 1 1 d . . . . .
H17 H 0.3139 0.1379 0.8462 0.041 Uiso 1 1 calc R . . . .
C10 C 0.1703(3) 0.2523(2) 0.8841(3) 0.0326(10) Uani 1 1 d . . . . .
C15 C 0.2064(3) 0.2830(2) 0.9870(4) 0.0381(11) Uani 1 1 d . . . . .
H15A H 0.1597 0.2706 1.0440 0.046 Uiso 1 1 calc R . . . .
H15B H 0.2045 0.3298 0.9802 0.046 Uiso 1 1 calc R . . . .
C14 C 0.2410(3) 0.2740(2) 0.7975(3) 0.0377(11) Uani 1 1 d . . . . .
H14A H 0.2184 0.2550 0.7304 0.045 Uiso 1 1 calc R . . . .
H14B H 0.2375 0.3207 0.7907 0.045 Uiso 1 1 calc R . . . .
C8 C 0.4225(4) 0.3646(2) 0.8647(3) 0.0370(11) Uani 1 1 d . . . . .
H8A H 0.4760 0.3938 0.8386 0.044 Uiso 1 1 calc R . . . .
H8B H 0.3551 0.3850 0.8521 0.044 Uiso 1 1 calc R . . . .
C2 C 0.5462(4) 0.3958(2) 1.2353(4) 0.0385(11) Uani 1 1 d . . . . .
H2 H 0.5369 0.3801 1.3042 0.046 Uiso 1 1 calc R . . . .
C19 C 0.4117(5) 0.0864(3) 1.0196(5) 0.0609(16) Uani 1 1 d . . . . .
H19A H 0.4359 0.0660 0.9556 0.091 Uiso 1 1 calc GR . . . .
H19B H 0.4100 0.0552 1.0763 0.091 Uiso 1 1 calc GR . . . .
H19C H 0.4584 0.1211 1.0388 0.091 Uiso 1 1 calc GR . . . .
H10 H 0.098(4) 0.267(2) 0.857(3) 0.034(12) Uiso 1 1 d . . . . .
H29 H 0.090(3) 0.781(2) -0.009(3) 0.019(11) Uiso 1 1 d . . . . .
H30 H 0.400(4) 0.731(2) -0.063(4) 0.042(13) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl3 C39 1.743(6) . ?
Cl2 C39 1.751(6) . ?
Cl1 C39 1.769(7) . ?
C39 H39 1.0000 . ?
N3 H3 0.8800 . ?
N3 C32 1.392(5) . ?
N3 C20 1.384(5) . ?
N4 C29 1.484(5) . ?
N4 C28 1.467(5) . ?
N4 C33 1.480(6) . ?
C32 C31 1.499(6) . ?
C32 C26 1.381(6) . ?
C31 H31 1.0000 . ?
C31 C29 1.535(6) . ?
C31 C34 1.556(6) . ?
C25 C26 1.429(6) . ?
C25 C20 1.418(6) . ?
C25 C24 1.405(6) . ?
C26 C27 1.498(6) . ?
C20 C21 1.379(6) . ?
C29 C35 1.525(6) . ?
C29 H29 0.77(4) . ?
C30 C34 1.524(6) . ?
C30 C36 1.521(7) . ?
C30 C33 1.517(6) . ?
C30 H30 0.95(5) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.528(6) . ?
C23 H23 0.9500 . ?
C23 C22 1.400(7) . ?
C23 C24 1.367(7) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C22 H22 0.9500 . ?
C22 C21 1.385(6) . ?
C24 H24 0.9500 . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 C35 1.534(6) . ?
C37 C38 1.520(7) . ?
C35 H35 1.0000 . ?
C35 C36 1.551(6) . ?
C21 H21 0.9500 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
N1 H1 0.8800 . ?
N1 C13 1.383(5) . ?
N1 C1 1.383(5) . ?
C12 H12 1.0000 . ?
C12 C11 1.529(6) . ?
C12 C13 1.487(6) . ?
C12 C15 1.560(6) . ?
N2 C11 1.465(5) . ?
N2 C9 1.480(6) . ?
N2 C14 1.490(5) . ?
C11 H11 1.0000 . ?
C11 C17 1.546(6) . ?
C13 C7 1.380(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.367(7) . ?
C4 C3 1.397(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(6) . ?
C1 C6 1.412(6) . ?
C1 C2 1.402(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.518(6) . ?
C6 C7 1.449(6) . ?
C7 C8 1.499(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C17 1.528(6) . ?
C18 C19 1.525(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.547(7) . ?
C16 C10 1.532(7) . ?
C3 H3A 0.9500 . ?
C3 C2 1.381(7) . ?
C17 H17 1.0000 . ?
C10 C15 1.537(6) . ?
C10 C14 1.517(6) . ?
C10 H10 1.05(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C2 H2 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
Cl3 C39 Cl2 111.6(3) . . ?
Cl3 C39 Cl1 109.0(3) . . ?
Cl3 C39 H39 109.2 . . ?
Cl2 C39 Cl1 108.8(3) . . ?
Cl2 C39 H39 109.2 . . ?
Cl1 C39 H39 109.2 . . ?
C32 N3 H3 125.7 . . ?
C20 N3 H3 125.7 . . ?
C20 N3 C32 108.6(3) . . ?
C28 N4 C29 117.0(3) . . ?
C28 N4 C33 114.6(3) . . ?
C33 N4 C29 110.2(3) . . ?
N3 C32 C31 119.7(3) . . ?
C26 C32 N3 109.7(4) . . ?
C26 C32 C31 130.5(4) . . ?
C32 C31 H31 107.9 . . ?
C32 C31 C29 112.2(3) . . ?
C32 C31 C34 113.8(3) . . ?
C29 C31 H31 107.9 . . ?
C29 C31 C34 106.9(3) . . ?
C34 C31 H31 107.9 . . ?
C20 C25 C26 107.6(3) . . ?
C24 C25 C26 134.5(4) . . ?
C24 C25 C20 117.8(4) . . ?
C32 C26 C25 106.6(4) . . ?
C32 C26 C27 125.5(4) . . ?
C25 C26 C27 127.9(4) . . ?
N3 C20 C25 107.5(4) . . ?
C21 C20 N3 129.6(4) . . ?
C21 C20 C25 122.9(4) . . ?
N4 C29 C31 113.4(3) . . ?
N4 C29 C35 107.8(3) . . ?
N4 C29 H29 106(3) . . ?
C31 C29 H29 106(3) . . ?
C35 C29 C31 110.0(3) . . ?
C35 C29 H29 113(3) . . ?
C34 C30 H30 113(3) . . ?
C36 C30 C34 109.7(4) . . ?
C36 C30 H30 109(3) . . ?
C33 C30 C34 107.7(4) . . ?
C33 C30 C36 109.7(4) . . ?
C33 C30 H30 108(3) . . ?
C26 C27 H27A 108.7 . . ?
C26 C27 H27B 108.7 . . ?
C26 C27 C28 114.4(4) . . ?
H27A C27 H27B 107.6 . . ?
C28 C27 H27A 108.7 . . ?
C28 C27 H27B 108.7 . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C24 C23 C22 121.4(4) . . ?
N4 C28 C27 118.9(3) . . ?
N4 C28 H28A 107.6 . . ?
N4 C28 H28B 107.6 . . ?
C27 C28 H28A 107.6 . . ?
C27 C28 H28B 107.6 . . ?
H28A C28 H28B 107.0 . . ?
C23 C22 H22 119.5 . . ?
C21 C22 C23 120.9(4) . . ?
C21 C22 H22 119.5 . . ?
C25 C24 H24 120.3 . . ?
C23 C24 C25 119.5(4) . . ?
C23 C24 H24 120.3 . . ?
C31 C34 H34A 109.7 . . ?
C31 C34 H34B 109.7 . . ?
C30 C34 C31 109.7(3) . . ?
C30 C34 H34A 109.7 . . ?
C30 C34 H34B 109.7 . . ?
H34A C34 H34B 108.2 . . ?
H37A C37 H37B 107.5 . . ?
C35 C37 H37A 108.5 . . ?
C35 C37 H37B 108.5 . . ?
C38 C37 H37A 108.5 . . ?
C38 C37 H37B 108.5 . . ?
C38 C37 C35 115.0(4) . . ?
C29 C35 C37 115.2(4) . . ?
C29 C35 H35 107.9 . . ?
C29 C35 C36 107.4(4) . . ?
C37 C35 H35 107.9 . . ?
C37 C35 C36 110.4(4) . . ?
C36 C35 H35 107.9 . . ?
C20 C21 C22 117.4(4) . . ?
C20 C21 H21 121.3 . . ?
C22 C21 H21 121.3 . . ?
C30 C36 C35 109.7(4) . . ?
C30 C36 H36A 109.7 . . ?
C30 C36 H36B 109.7 . . ?
C35 C36 H36A 109.7 . . ?
C35 C36 H36B 109.7 . . ?
H36A C36 H36B 108.2 . . ?
N4 C33 C30 110.6(4) . . ?
N4 C33 H33A 109.5 . . ?
N4 C33 H33B 109.5 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 108.1 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C13 N1 H1 125.5 . . ?
C1 N1 H1 125.5 . . ?
C1 N1 C13 109.1(3) . . ?
C11 C12 H12 107.0 . . ?
C11 C12 C15 107.6(3) . . ?
C13 C12 H12 107.0 . . ?
C13 C12 C11 113.2(3) . . ?
C13 C12 C15 114.6(4) . . ?
C15 C12 H12 107.0 . . ?
C11 N2 C9 116.6(3) . . ?
C11 N2 C14 111.2(3) . . ?
C9 N2 C14 114.6(3) . . ?
C12 C11 H11 108.7 . . ?
C12 C11 C17 110.1(3) . . ?
N2 C11 C12 113.4(3) . . ?
N2 C11 H11 108.7 . . ?
N2 C11 C17 107.0(3) . . ?
C17 C11 H11 108.7 . . ?
N1 C13 C12 121.1(4) . . ?
C7 C13 N1 109.6(4) . . ?
C7 C13 C12 129.2(4) . . ?
C5 C4 H4 119.2 . . ?
C5 C4 C3 121.6(5) . . ?
C3 C4 H4 119.2 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.2(4) . . ?
C6 C5 H5 120.4 . . ?
N1 C1 C6 107.8(3) . . ?
N1 C1 C2 130.6(4) . . ?
C2 C1 C6 121.6(4) . . ?
N2 C9 H9A 107.7 . . ?
N2 C9 H9B 107.7 . . ?
N2 C9 C8 118.3(4) . . ?
H9A C9 H9B 107.1 . . ?
C8 C9 H9A 107.7 . . ?
C8 C9 H9B 107.7 . . ?
C5 C6 C1 119.1(4) . . ?
C5 C6 C7 133.9(4) . . ?
C1 C6 C7 107.0(4) . . ?
C13 C7 C6 106.5(4) . . ?
C13 C7 C8 126.4(4) . . ?
C6 C7 C8 127.1(4) . . ?
H18A C18 H18B 107.3 . . ?
C17 C18 H18A 108.2 . . ?
C17 C18 H18B 108.2 . . ?
C19 C18 H18A 108.2 . . ?
C19 C18 H18B 108.2 . . ?
C19 C18 C17 116.6(4) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C10 C16 H16A 109.6 . . ?
C10 C16 H16B 109.6 . . ?
C10 C16 C17 110.3(4) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 C4 121.1(4) . . ?
C2 C3 H3A 119.5 . . ?
C11 C17 C16 107.4(4) . . ?
C11 C17 H17 107.2 . . ?
C18 C17 C11 115.0(3) . . ?
C18 C17 C16 112.3(4) . . ?
C18 C17 H17 107.2 . . ?
C16 C17 H17 107.2 . . ?
C16 C10 C15 109.0(4) . . ?
C16 C10 H10 112(2) . . ?
C15 C10 H10 116(2) . . ?
C14 C10 C16 108.7(4) . . ?
C14 C10 C15 108.5(4) . . ?
C14 C10 H10 103(2) . . ?
C12 C15 H15A 109.7 . . ?
C12 C15 H15B 109.7 . . ?
C10 C15 C12 109.7(4) . . ?
C10 C15 H15A 109.7 . . ?
C10 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N2 C14 C10 110.1(3) . . ?
N2 C14 H14A 109.6 . . ?
N2 C14 H14B 109.6 . . ?
C10 C14 H14A 109.6 . . ?
C10 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C9 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C7 C8 C9 115.6(4) . . ?
C7 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
H8A C8 H8B 107.4 . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.5(4) . . ?
C3 C2 H2 121.2 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3, Acetone'
####################################################################### 
# 
# 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_exp_5273
_database_code_depnum_ccdc_archive 'CCDC 1433188'
_audit_update_record             
;
2015-10-26 deposited with the CCDC.
2016-05-16 downloaded from the CCDC.
;
_audit_creation_date             2015-05-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H19 N3'
_chemical_formula_sum            'C18 H19 N3'
_chemical_formula_weight         277.36
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H20 N3'
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'

_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           41
_space_group_name_H-M_alt        'A e a 2'
_space_group_name_Hall           'A 2 -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z+1/2'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1'
'x+1/2, -y+1/2, z+1'

_cell_length_a                   12.2491(9)
_cell_length_b                   35.949(3)
_cell_length_c                   13.0880(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5763.2(8)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    4911
_cell_measurement_temperature    100.02(18)
_cell_measurement_theta_max      28.5210
_cell_measurement_theta_min      3.1760
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             2368
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14143
_diffrn_reflns_point_group_measured_fraction_full 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         2.842
_diffrn_ambient_temperature      100.02(18)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   34.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017 -178.0000  -90.0000 64

#__ type_ start__ end____ width___ exp.time_
  2 omega  -40.00  -13.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -57.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -18.00   19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -38.0000   60.0000 37

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   26.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -99.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega  -36.00   22.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -77.0000    0.0000 58
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0015519000
_diffrn_orient_matrix_UB_12      -0.0138871000
_diffrn_orient_matrix_UB_13      0.0384684000
_diffrn_orient_matrix_UB_21      0.0193888000
_diffrn_orient_matrix_UB_22      0.0133120000
_diffrn_orient_matrix_UB_23      0.0356358000
_diffrn_orient_matrix_UB_31      -0.0545346000
_diffrn_orient_matrix_UB_32      0.0043400000
_diffrn_orient_matrix_UB_33      0.0137169000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.781
_reflns_Friedel_fraction_max     0.764
_reflns_number_gt                4322
_reflns_number_total             5020
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 1634 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.6(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5020
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.065
_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)+(0.0588P)²+2.2613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1160
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13), C14(H14), C15(H15), C29(H29), C31(H31), C33(H33), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C17(H17A,H17B),
 C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C30(H30A,H30B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C20(H20), C21(H21), C22(H22), C23(H23),
 N1(H1), N4(H4A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C1 C 1.1504(3) 0.79248(9) 0.8542(3) 0.0208(8) Uani 1 1 d . . . . .
C2 C 1.2399(3) 0.78245(9) 0.7955(3) 0.0235(9) Uani 1 1 d . . . . .
H2 H 1.2316 0.7735 0.7277 0.028 Uiso 1 1 calc R . . . .
C3 C 1.3418(3) 0.78602(9) 0.8399(3) 0.0259(8) Uani 1 1 d . . . . .
H3 H 1.4048 0.7799 0.8012 0.031 Uiso 1 1 calc R . . . .
C4 C 1.3541(3) 0.79847(10) 0.9401(3) 0.0278(9) Uani 1 1 d . . . . .
H4 H 1.4253 0.8004 0.9686 0.033 Uiso 1 1 calc R . . . .
C5 C 1.2651(3) 0.80799(9) 0.9985(3) 0.0256(8) Uani 1 1 d . . . . .
H5 H 1.2745 0.8163 1.0668 0.031 Uiso 1 1 calc R . . . .
C6 C 1.1606(3) 0.80527(9) 0.9563(3) 0.0207(8) Uani 1 1 d . . . . .
C7 C 1.0532(2) 0.81355(9) 0.9935(3) 0.0203(7) Uani 1 1 d . . . . .
C8 C 1.0309(3) 0.83013(10) 1.0966(3) 0.0264(8) Uani 1 1 d . . . . .
H8A H 1.0323 0.8576 1.0899 0.032 Uiso 1 1 calc R . . . .
H8B H 1.0912 0.8230 1.1430 0.032 Uiso 1 1 calc R . . . .
C9 C 0.9229(3) 0.81903(10) 1.1469(3) 0.0277(8) Uani 1 1 d . . . . .
H9A H 0.9270 0.7923 1.1642 0.033 Uiso 1 1 calc R . . . .
H9B H 0.9165 0.8329 1.2120 0.033 Uiso 1 1 calc R . . . .
C10 C 0.8044(3) 0.86366(10) 1.0561(3) 0.0330(9) Uani 1 1 d . . . . .
H10A H 0.8752 0.8766 1.0488 0.040 Uiso 1 1 calc R . . . .
H10B H 0.7607 0.8769 1.1083 0.040 Uiso 1 1 calc R . . . .
C11 C 0.7445(3) 0.86392(9) 0.9551(3) 0.0267(9) Uani 1 1 d . . . . .
H11 H 0.7230 0.8900 0.9374 0.032 Uiso 1 1 calc R . . . .
C12 C 0.6427(3) 0.83968(9) 0.9628(3) 0.0249(8) Uani 1 1 d . . . . .
H12A H 0.6013 0.8406 0.8980 0.030 Uiso 1 1 calc R . . . .
H12B H 0.5949 0.8488 1.0184 0.030 Uiso 1 1 calc R . . . .
C13 C 0.6800(2) 0.79894(9) 0.9856(3) 0.0204(8) Uani 1 1 d . . . . .
H13 H 0.6649 0.7833 0.9240 0.025 Uiso 1 1 calc R . . . .
C14 C 0.8037(2) 0.79901(9) 1.0053(3) 0.0198(7) Uani 1 1 d . . . . .
H14 H 0.8270 0.7736 1.0271 0.024 Uiso 1 1 calc R . . . .
C15 C 0.8612(2) 0.80907(9) 0.9052(3) 0.0200(7) Uani 1 1 d . . . . .
H15 H 0.8370 0.7909 0.8519 0.024 Uiso 1 1 calc R . . . .
C16 C 0.9820(2) 0.80589(8) 0.9154(3) 0.0204(7) Uani 1 1 d . . . . .
C17 C 0.8207(3) 0.84858(10) 0.8725(3) 0.0308(9) Uani 1 1 d . . . . .
H17A H 0.8839 0.8654 0.8636 0.037 Uiso 1 1 calc R . . . .
H17B H 0.7813 0.8470 0.8066 0.037 Uiso 1 1 calc R . . . .
C18 C 0.6204(3) 0.78337(9) 1.0724(3) 0.0232(8) Uani 1 1 d . . . . .
C19 C -0.1693(2) 0.95940(8) 0.9132(3) 0.0189(7) Uani 1 1 d . . . . .
C20 C -0.2584(2) 0.97002(9) 0.9720(3) 0.0212(8) Uani 1 1 d . . . . .
H20 H -0.2494 0.9790 1.0398 0.025 Uiso 1 1 calc R . . . .
C21 C -0.3607(3) 0.96708(9) 0.9282(3) 0.0256(8) Uani 1 1 d . . . . .
H21 H -0.4231 0.9739 0.9671 0.031 Uiso 1 1 calc R . . . .
C22 C -0.3745(3) 0.95442(9) 0.8287(3) 0.0273(9) Uani 1 1 d . . . . .
H22 H -0.4459 0.9529 0.8007 0.033 Uiso 1 1 calc R . . . .
C23 C -0.2866(2) 0.94407(9) 0.7704(3) 0.0244(8) Uani 1 1 d . . . . .
H23 H -0.2970 0.9354 0.7025 0.029 Uiso 1 1 calc R . . . .
C24 C -0.1812(2) 0.94631(9) 0.8117(3) 0.0203(8) Uani 1 1 d . . . . .
C25 C -0.0744(2) 0.93780(9) 0.7733(3) 0.0197(7) Uani 1 1 d . . . . .
C26 C -0.0527(3) 0.91940(10) 0.6730(3) 0.0250(8) Uani 1 1 d . . . . .
H26A H -0.1126 0.9261 0.6256 0.030 Uiso 1 1 calc R . . . .
H26B H -0.0558 0.8921 0.6833 0.030 Uiso 1 1 calc R . . . .
C27 C 0.0559(3) 0.92878(11) 0.6210(3) 0.0287(8) Uani 1 1 d . . . . .
H27A H 0.0611 0.9137 0.5578 0.034 Uiso 1 1 calc R . . . .
H27B H 0.0533 0.9552 0.6000 0.034 Uiso 1 1 calc R . . . .
C28 C 0.1744(3) 0.88495(10) 0.7163(4) 0.0418(11) Uani 1 1 d . . . . .
H28A H 0.2189 0.8710 0.6661 0.050 Uiso 1 1 calc R . . . .
H28B H 0.1038 0.8719 0.7245 0.050 Uiso 1 1 calc R . . . .
C29 C 0.2336(3) 0.88647(9) 0.8184(4) 0.0296(10) Uani 1 1 d . . . . .
H29 H 0.2541 0.8607 0.8401 0.036 Uiso 1 1 calc R . . . .
C30 C 0.1568(3) 0.90352(10) 0.8971(3) 0.0359(10) Uani 1 1 d . . . . .
H30A H 0.1947 0.9059 0.9635 0.043 Uiso 1 1 calc R . . . .
H30B H 0.0925 0.8872 0.9066 0.043 Uiso 1 1 calc R . . . .
C31 C 0.1189(2) 0.94260(9) 0.8599(3) 0.0197(7) Uani 1 1 d . . . . .
H31 H 0.1444 0.9614 0.9109 0.024 Uiso 1 1 calc R . . . .
C32 C -0.0029(2) 0.94583(8) 0.8514(3) 0.0185(7) Uani 1 1 d . . . . .
C33 C 0.1765(2) 0.95057(9) 0.7587(3) 0.0191(7) Uani 1 1 d . . . . .
H33 H 0.1543 0.9757 0.7336 0.023 Uiso 1 1 calc R . . . .
C34 C 0.3008(2) 0.95017(9) 0.7771(3) 0.0196(7) Uani 1 1 d . . . . .
H34 H 0.3189 0.9677 0.8339 0.024 Uiso 1 1 calc R . . . .
C35 C 0.3351(3) 0.90995(9) 0.8084(3) 0.0253(8) Uani 1 1 d . . . . .
H35A H 0.3840 0.8992 0.7559 0.030 Uiso 1 1 calc R . . . .
H35B H 0.3748 0.9105 0.8742 0.030 Uiso 1 1 calc R . . . .
C36 C 0.3585(3) 0.96179(9) 0.6846(3) 0.0219(7) Uani 1 1 d . . . . .
N1 N 1.0408(2) 0.79310(7) 0.8319(2) 0.0225(6) Uani 1 1 d . . . . .
H1 H 1.0121 0.7864 0.7731 0.027 Uiso 1 1 calc R . . . .
N2 N 0.8229(2) 0.82510(7) 1.0887(2) 0.0238(6) Uani 1 1 d . . . . .
N3 N 0.5727(2) 0.77187(8) 1.1405(3) 0.0316(7) Uani 1 1 d . . . . .
N4 N -0.0602(2) 0.95866(7) 0.9353(2) 0.0200(6) Uani 1 1 d . . . . .
H4A H -0.0309 0.9653 0.9939 0.024 Uiso 1 1 calc R . . . .
N5 N 0.1555(2) 0.92311(8) 0.6792(2) 0.0254(7) Uani 1 1 d . . . . .
N6 N 0.4055(2) 0.97015(8) 0.6131(2) 0.0291(7) 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 C2 1.386(5) . ?
C1 C6 1.418(5) . ?
C1 N1 1.373(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.375(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.398(5) . ?
C6 C7 1.434(4) . ?
C7 C8 1.500(5) . ?
C7 C16 1.372(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.531(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 N2 1.458(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.512(6) . ?
C10 N2 1.468(4) . ?
C11 H11 1.0000 . ?
C11 C12 1.524(5) . ?
C11 C17 1.530(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.563(4) . ?
C13 H13 1.0000 . ?
C13 C14 1.537(4) . ?
C13 C18 1.462(5) . ?
C14 H14 1.0000 . ?
C14 C15 1.531(5) . ?
C14 N2 1.458(5) . ?
C15 H15 1.0000 . ?
C15 C16 1.491(4) . ?
C15 C17 1.564(5) . ?
C16 N1 1.388(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 N3 1.143(5) . ?
C19 C20 1.389(5) . ?
C19 C24 1.417(5) . ?
C19 N4 1.368(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.382(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.371(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.401(5) . ?
C24 C25 1.434(4) . ?
C25 C26 1.494(5) . ?
C25 C32 1.378(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.532(5) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 N5 1.453(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.521(6) . ?
C28 N5 1.474(5) . ?
C29 H29 1.0000 . ?
C29 C30 1.524(6) . ?
C29 C35 1.508(5) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.557(5) . ?
C31 H31 1.0000 . ?
C31 C32 1.500(4) . ?
C31 C33 1.527(5) . ?
C32 N4 1.382(4) . ?
C33 H33 1.0000 . ?
C33 C34 1.542(4) . ?
C33 N5 1.458(5) . ?
C34 H34 1.0000 . ?
C34 C35 1.560(4) . ?
C34 C36 1.462(5) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 N6 1.139(5) . ?
N1 H1 0.8800 . ?
N4 H4A 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.4(3) . . ?
N1 C1 C2 131.3(4) . . ?
N1 C1 C6 106.4(3) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.2(4) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.5(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.3(4) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C7 107.8(3) . . ?
C5 C6 C1 118.4(3) . . ?
C5 C6 C7 133.7(4) . . ?
C6 C7 C8 123.8(3) . . ?
C16 C7 C6 106.7(3) . . ?
C16 C7 C8 129.4(3) . . ?
C7 C8 H8A 108.2 . . ?
C7 C8 H8B 108.2 . . ?
C7 C8 C9 116.1(3) . . ?
H8A C8 H8B 107.4 . . ?
C9 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
C8 C9 H9A 107.9 . . ?
C8 C9 H9B 107.9 . . ?
H9A C9 H9B 107.2 . . ?
N2 C9 C8 117.5(3) . . ?
N2 C9 H9A 107.9 . . ?
N2 C9 H9B 107.9 . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
N2 C10 H10A 109.8 . . ?
N2 C10 H10B 109.8 . . ?
N2 C10 C11 109.6(3) . . ?
C10 C11 H11 109.6 . . ?
C10 C11 C12 109.6(3) . . ?
C10 C11 C17 108.6(3) . . ?
C12 C11 H11 109.6 . . ?
C12 C11 C17 109.9(3) . . ?
C17 C11 H11 109.6 . . ?
C11 C12 H12A 110.1 . . ?
C11 C12 H12B 110.1 . . ?
C11 C12 C13 108.0(3) . . ?
H12A C12 H12B 108.4 . . ?
C13 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
C12 C13 H13 108.6 . . ?
C14 C13 C12 108.6(2) . . ?
C14 C13 H13 108.6 . . ?
C18 C13 C12 111.2(3) . . ?
C18 C13 H13 108.6 . . ?
C18 C13 C14 111.2(3) . . ?
C13 C14 H14 109.2 . . ?
C15 C14 C13 108.1(3) . . ?
C15 C14 H14 109.2 . . ?
N2 C14 C13 106.6(3) . . ?
N2 C14 H14 109.2 . . ?
N2 C14 C15 114.5(3) . . ?
C14 C15 H15 107.9 . . ?
C14 C15 C17 107.6(3) . . ?
C16 C15 C14 111.2(3) . . ?
C16 C15 H15 107.9 . . ?
C16 C15 C17 114.1(3) . . ?
C17 C15 H15 107.9 . . ?
C7 C16 C15 133.0(3) . . ?
C7 C16 N1 108.9(3) . . ?
N1 C16 C15 118.1(3) . . ?
C11 C17 C15 109.1(3) . . ?
C11 C17 H17A 109.9 . . ?
C11 C17 H17B 109.9 . . ?
C15 C17 H17A 109.9 . . ?
C15 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
N3 C18 C13 178.6(4) . . ?
C20 C19 C24 122.0(3) . . ?
N4 C19 C20 131.0(4) . . ?
N4 C19 C24 107.0(3) . . ?
C19 C20 H20 121.3 . . ?
C21 C20 C19 117.5(4) . . ?
C21 C20 H20 121.3 . . ?
C20 C21 H21 119.2 . . ?
C20 C21 C22 121.6(3) . . ?
C22 C21 H21 119.2 . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 121.0(3) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.5(4) . . ?
C24 C23 H23 120.2 . . ?
C19 C24 C25 107.8(3) . . ?
C23 C24 C19 118.4(3) . . ?
C23 C24 C25 133.8(4) . . ?
C24 C25 C26 124.4(3) . . ?
C32 C25 C24 106.0(3) . . ?
C32 C25 C26 129.2(3) . . ?
C25 C26 H26A 108.1 . . ?
C25 C26 H26B 108.1 . . ?
C25 C26 C27 116.6(3) . . ?
H26A C26 H26B 107.3 . . ?
C27 C26 H26A 108.1 . . ?
C27 C26 H26B 108.1 . . ?
C26 C27 H27A 107.9 . . ?
C26 C27 H27B 107.9 . . ?
H27A C27 H27B 107.2 . . ?
N5 C27 C26 117.8(3) . . ?
N5 C27 H27A 107.9 . . ?
N5 C27 H27B 107.9 . . ?
H28A C28 H28B 108.2 . . ?
C29 C28 H28A 109.8 . . ?
C29 C28 H28B 109.8 . . ?
N5 C28 H28A 109.8 . . ?
N5 C28 H28B 109.8 . . ?
N5 C28 C29 109.4(3) . . ?
C28 C29 H29 109.6 . . ?
C28 C29 C30 108.2(3) . . ?
C30 C29 H29 109.6 . . ?
C35 C29 C28 109.6(3) . . ?
C35 C29 H29 109.6 . . ?
C35 C29 C30 110.0(3) . . ?
C29 C30 H30A 109.7 . . ?
C29 C30 H30B 109.7 . . ?
C29 C30 C31 109.6(3) . . ?
H30A C30 H30B 108.2 . . ?
C31 C30 H30A 109.7 . . ?
C31 C30 H30B 109.7 . . ?
C30 C31 H31 107.9 . . ?
C32 C31 C30 112.9(3) . . ?
C32 C31 H31 107.9 . . ?
C32 C31 C33 112.4(3) . . ?
C33 C31 C30 107.6(3) . . ?
C33 C31 H31 107.9 . . ?
C25 C32 C31 132.2(3) . . ?
C25 C32 N4 109.6(3) . . ?
N4 C32 C31 118.2(3) . . ?
C31 C33 H33 109.2 . . ?
C31 C33 C34 108.7(3) . . ?
C34 C33 H33 109.2 . . ?
N5 C33 C31 114.2(3) . . ?
N5 C33 H33 109.2 . . ?
N5 C33 C34 106.2(3) . . ?
C33 C34 H34 109.2 . . ?
C33 C34 C35 108.4(2) . . ?
C35 C34 H34 109.2 . . ?
C36 C34 C33 110.2(3) . . ?
C36 C34 H34 109.2 . . ?
C36 C34 C35 110.6(3) . . ?
C29 C35 C34 108.7(3) . . ?
C29 C35 H35A 110.0 . . ?
C29 C35 H35B 110.0 . . ?
C34 C35 H35A 110.0 . . ?
C34 C35 H35B 110.0 . . ?
H35A C35 H35B 108.3 . . ?
N6 C36 C34 178.2(4) . . ?
C1 N1 C16 110.2(3) . . ?
C1 N1 H1 124.9 . . ?
C16 N1 H1 124.9 . . ?
C9 N2 C10 115.0(3) . . ?
C9 N2 C14 115.5(2) . . ?
C14 N2 C10 111.4(3) . . ?
C19 N4 C32 109.6(3) . . ?
C19 N4 H4A 125.2 . . ?
C32 N4 H4A 125.2 . . ?
C27 N5 C28 115.8(3) . . ?
C27 N5 C33 115.3(3) . . ?
C33 N5 C28 111.5(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
