# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1956525'
loop_
_audit_author_name
_audit_author_address
'Werner Kaminsky'
;University of Washington
United States of America
;
_audit_update_record             
;
2019-11-01 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;

_audit_creation_date             2018-06-29T14:19:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C46 H54 N8 O4'
_chemical_formula_sum            'C46 H54 N8 O4'
_chemical_formula_weight         782.97

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.7211(18)
_cell_length_b                   13.737(5)
_cell_length_c                   15.384(6)
_cell_angle_alpha                77.216(14)
_cell_angle_beta                 86.717(15)
_cell_angle_gamma                85.596(18)
_cell_volume                     969.3(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    709
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      21.79
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             418

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.553
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.999

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      -0.121358
_diffrn_orient_matrix_ub_12      0.045552
_diffrn_orient_matrix_ub_13      -0.045124
_diffrn_orient_matrix_ub_21      -0.122351
_diffrn_orient_matrix_ub_22      0.020182
_diffrn_orient_matrix_ub_23      0.049133
_diffrn_orient_matrix_ub_31      0.124544
_diffrn_orient_matrix_ub_32      0.055803
_diffrn_orient_matrix_ub_33      -0.00042
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.1113
_diffrn_reflns_av_unetI/netI     0.3039
_diffrn_reflns_number            4805
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.523
_diffrn_reflns_theta_max         25.155
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_reflns_Friedel_coverage         0
_reflns_number_total             3404
_reflns_number_gt                1196
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0601P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.011(3)
_refine_ls_number_reflns         3404
_refine_ls_number_parameters     265
_refine_ls_number_restraints     162
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.2578
_refine_ls_R_factor_gt           0.0753
_refine_ls_wR_factor_ref         0.1999
_refine_ls_wR_factor_gt          0.14
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_restrained_S_all      0.927
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.067

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.1842(12) 0.6687(4) 0.8214(4) 0.0253(15) Uani 1 1 d . U . . .
H1 H 0.1004 0.7136 0.7721 0.03 Uiso 1 1 calc R U . . .
C2 C 0.1218(12) 0.5687(4) 0.8409(4) 0.0279(15) Uani 1 1 d . U . . .
H2 H -0.0091 0.5465 0.8061 0.033 Uiso 1 1 calc R U . . .
C3 C 0.2491(11) 0.5011(4) 0.9108(4) 0.0214(14) Uani 1 1 d . U . . .
C4 C 0.4364(11) 0.5347(3) 0.9641(4) 0.0201(14) Uani 1 1 d . U . . .
C5 C 0.1963(12) 0.3958(4) 0.9286(4) 0.0292(16) Uani 1 1 d . U . . .
H5 H 0.0738 0.3719 0.8922 0.035 Uiso 1 1 calc R U . . .
C6 C 0.3219(12) 0.3322(4) 0.9970(4) 0.0250(15) Uani 1 1 d . U . . .
H6 H 0.2839 0.2635 1.008 0.03 Uiso 1 1 calc R U . . .
C7 C 0.5084(11) 0.3626(4) 1.0535(4) 0.0218(14) Uani 1 1 d . U . . .
C8 C 0.6328(11) 0.2968(3) 1.1269(4) 0.0223(14) Uani 1 1 d . U . . .
C9 C 0.5449(12) 0.1925(4) 1.1560(4) 0.0266(15) Uani 1 1 d . U . . .
C10 C 0.3330(11) 0.0667(3) 1.2242(4) 0.0207(14) Uani 1 1 d . U . . .
C11 C 0.5056(11) 0.0334(3) 1.1616(4) 0.0216(14) Uani 1 1 d . U . . .
C12 C 0.8493(12) 0.1186(4) 1.0416(4) 0.0306(16) Uani 1 1 d . U . . .
H12A H 1.0337 0.0888 1.0638 0.046 Uiso 1 1 calc R U . . .
H12B H 0.8689 0.1883 1.0104 0.046 Uiso 1 1 calc R U . . .
H12C H 0.7837 0.0809 1.0003 0.046 Uiso 1 1 calc R U . . .
C13 C 0.5155(12) -0.0677(4) 1.1506(4) 0.0248(15) Uani 1 1 d . U . . .
C14 C 0.1201(12) -0.0893(4) 1.2678(4) 0.0283(15) Uani 1 1 d . U . . .
C15 C -0.0305(12) 0.0442(4) 1.3469(4) 0.0326(17) Uani 1 1 d . U . . .
H15A H 0.04 0.1066 1.3554 0.049 Uiso 1 1 calc R U . . .
H15B H -0.0245 -0.0058 1.4033 0.049 Uiso 1 1 calc R U . . .
H15C H -0.2268 0.0567 1.3277 0.049 Uiso 1 1 calc R U . . .
C16 C 0.2823(13) -0.2279(3) 1.2016(4) 0.0304(16) Uani 1 1 d . U . . .
H16A H 0.3824 -0.241 1.1466 0.036 Uiso 1 1 calc R U . . .
H16B H 0.0782 -0.2377 1.1979 0.036 Uiso 1 1 calc R U . . .
C17 C 0.4008(12) -0.3018(3) 1.2821(4) 0.0294(16) Uani 1 1 d . U . . .
H17A H 0.3252 -0.2819 1.3374 0.035 Uiso 1 1 calc R U . . .
H17B H 0.6105 -0.3004 1.2801 0.035 Uiso 1 1 calc R U . . .
C18 C 0.3208(12) -0.4075(3) 1.2836(4) 0.0291(16) Uani 1 1 d . U . . .
H18A H 0.4019 -0.4276 1.2289 0.035 Uiso 1 1 calc R U . . .
H18B H 0.1113 -0.4076 1.2828 0.035 Uiso 1 1 calc R U . . .
C19 C 0.4254(13) -0.4846(3) 1.3651(4) 0.0325(16) Uani 1 1 d . U . . .
H19A H 0.6345 -0.4834 1.3665 0.039 Uiso 1 1 calc R U . . .
H19B H 0.3412 -0.4652 1.4197 0.039 Uiso 1 1 calc R U . . .
C20 C 0.3521(13) -0.5893(3) 1.3659(4) 0.0324(16) Uani 1 1 d . U . . .
H20A H 0.4276 -0.6074 1.3098 0.039 Uiso 1 1 calc R U . . .
H20B H 0.1427 -0.5913 1.3676 0.039 Uiso 1 1 calc R U . . .
C21 C 0.4696(13) -0.6670(4) 1.4446(4) 0.0351(17) Uani 1 1 d . U . . .
H21A H 0.6768 -0.6609 1.4459 0.042 Uiso 1 1 calc R U . . .
H21B H 0.3811 -0.6522 1.5005 0.042 Uiso 1 1 calc R U . . .
C22 C 0.4184(13) -0.7739(4) 1.4419(4) 0.0354(17) Uani 1 1 d . U . . .
H22A H 0.2108 -0.7811 1.4445 0.043 Uiso 1 1 calc R U . . .
H22B H 0.4961 -0.7874 1.3843 0.043 Uiso 1 1 calc R U . . .
C23 C 0.5487(13) -0.8505(4) 1.5160(4) 0.0401(18) Uani 1 1 d . U . . .
H23A H 0.5072 -0.9175 1.51 0.06 Uiso 1 1 calc R U . . .
H23B H 0.7551 -0.8453 1.5132 0.06 Uiso 1 1 calc R U . . .
H23C H 0.4694 -0.839 1.5735 0.06 Uiso 1 1 calc R U . . .
N1 N 0.6442(9) 0.1153(3) 1.1160(3) 0.0235(12) Uani 1 1 d . U . . .
N2 N 0.3539(10) 0.1647(3) 1.2218(3) 0.0260(13) Uani 1 1 d . U . . .
N3 N 0.1485(10) 0.0070(3) 1.2788(3) 0.0265(13) Uani 1 1 d . U . . .
N4 N 0.3154(9) -0.1231(3) 1.2070(3) 0.0229(12) Uani 1 1 d . U . . .
O1 O -0.0570(8) -0.1424(2) 1.3109(3) 0.0307(11) Uani 1 1 d . . . . .
O2 O 0.6746(8) -0.1047(2) 1.0988(3) 0.0313(11) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C8 1.384(7) 2_667 ?
C1 C2 1.389(7) . ?
C1 H1 0.95 . ?
C2 C3 1.388(7) . ?
C2 H2 0.95 . ?
C3 C4 1.407(7) . ?
C3 C5 1.450(7) . ?
C4 C7 1.417(6) 2_667 ?
C4 C4 1.419(10) 2_667 ?
C5 C6 1.344(7) . ?
C5 H5 0.95 . ?
C6 C7 1.418(7) . ?
C6 H6 0.95 . ?
C7 C8 1.408(7) . ?
C7 C4 1.417(6) 2_667 ?
C8 C1 1.384(7) 2_667 ?
C8 C9 1.487(7) . ?
C9 N2 1.327(6) . ?
C9 N1 1.379(6) . ?
C10 N2 1.348(6) . ?
C10 C11 1.360(7) . ?
C10 N3 1.363(6) . ?
C11 N1 1.377(6) . ?
C11 C13 1.434(7) . ?
C12 N1 1.452(6) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 O2 1.228(6) . ?
C13 N4 1.396(6) . ?
C14 O1 1.219(6) . ?
C14 N3 1.388(6) . ?
C14 N4 1.404(7) . ?
C15 N3 1.463(6) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 N4 1.480(6) . ?
C16 C17 1.521(7) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 C18 1.523(7) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 C19 1.529(7) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C19 C20 1.502(7) . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 C21 1.525(7) . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C21 C22 1.516(7) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C22 C23 1.496(7) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C1 C2 120.6(5) 2_667 . ?
C8 C1 H1 119.7 2_667 . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 120.6(5) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 C5 120.9(5) . . ?
C4 C3 C5 119.4(5) . . ?
C3 C4 C7 119.8(5) . 2_667 ?
C3 C4 C4 119.3(6) . 2_667 ?
C7 C4 C4 120.9(6) 2_667 2_667 ?
C6 C5 C3 119.5(5) . . ?
C6 C5 H5 120.3 . . ?
C3 C5 H5 120.3 . . ?
C5 C6 C7 123.2(5) . . ?
C5 C6 H6 118.4 . . ?
C7 C6 H6 118.4 . . ?
C8 C7 C4 119.0(5) . 2_667 ?
C8 C7 C6 123.3(5) . . ?
C4 C7 C6 117.7(5) 2_667 . ?
C1 C8 C7 120.2(4) 2_667 . ?
C1 C8 C9 118.9(5) 2_667 . ?
C7 C8 C9 120.5(5) . . ?
N2 C9 N1 112.7(4) . . ?
N2 C9 C8 123.2(5) . . ?
N1 C9 C8 124.0(5) . . ?
N2 C10 C11 112.7(4) . . ?
N2 C10 N3 125.0(5) . . ?
C11 C10 N3 122.2(4) . . ?
C10 C11 N1 105.6(4) . . ?
C10 C11 C13 122.6(5) . . ?
N1 C11 C13 131.7(5) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 N4 121.8(4) . . ?
O2 C13 C11 126.5(5) . . ?
N4 C13 C11 111.6(5) . . ?
O1 C14 N3 121.9(5) . . ?
O1 C14 N4 122.2(5) . . ?
N3 C14 N4 115.9(5) . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 C17 111.7(4) . . ?
N4 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N4 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 C18 111.0(5) . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108 . . ?
C17 C18 C19 113.3(5) . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C18 113.5(5) . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 C21 113.5(5) . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C22 C21 C20 114.0(5) . . ?
C22 C21 H21A 108.8 . . ?
C20 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
C20 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C23 C22 C21 114.0(5) . . ?
C23 C22 H22A 108.8 . . ?
C21 C22 H22A 108.8 . . ?
C23 C22 H22B 108.8 . . ?
C21 C22 H22B 108.8 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C11 N1 C9 105.2(4) . . ?
C11 N1 C12 126.9(4) . . ?
C9 N1 C12 127.9(4) . . ?
C9 N2 C10 103.8(4) . . ?
C10 N3 C14 119.9(5) . . ?
C10 N3 C15 121.0(4) . . ?
C14 N3 C15 119.0(4) . . ?
C13 N4 C14 127.2(4) . . ?
C13 N4 C16 119.5(5) . . ?
C14 N4 C16 113.2(4) . . ?


#----------------------------------------------------------------------------#
#                   SQUEEZE DETAILS                                          #
#----------------------------------------------------------------------------#



# END of CIF
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1956526'
loop_
_audit_author_name
_audit_author_address
'Werner Kaminsky'
;University of Washington
United States of America
;
_audit_update_record             
;
2019-11-01 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;

_audit_creation_date             2018-07-10T11:42:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C31 H32 N4 O2'
_chemical_formula_sum            'C31 H32 N4 O2'
_chemical_formula_weight         492.6

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   21.6000(16)
_cell_length_b                   12.9539(10)
_cell_length_c                   8.9450(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.508(4)
_cell_angle_gamma                90
_cell_volume                     2502.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.87
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.997

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      -0.034195
_diffrn_orient_matrix_ub_12      -0.051006
_diffrn_orient_matrix_ub_13      -0.031861
_diffrn_orient_matrix_ub_21      -0.018782
_diffrn_orient_matrix_ub_22      -0.051818
_diffrn_orient_matrix_ub_23      0.033355
_diffrn_orient_matrix_ub_31      -0.10477
_diffrn_orient_matrix_ub_32      0.025936
_diffrn_orient_matrix_ub_33      0.003981
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_number            12181
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.833
_diffrn_reflns_theta_max         28.343
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             6225
_reflns_number_gt                4499
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+0.9464P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0023(6)
_refine_ls_number_reflns         6225
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1184
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_restrained_S_all      1.02
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.049

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.78990(6) 0.06929(11) 0.73514(15) 0.0183(3) Uani 1 1 d . . . . .
C2 C 0.75020(7) 0.04238(12) 0.61737(16) 0.0218(3) Uani 1 1 d . . . . .
H2 H 0.767 0.0293 0.5214 0.026 Uiso 1 1 calc R U . . .
C3 C 0.68714(7) 0.03434(12) 0.63749(17) 0.0225(3) Uani 1 1 d . . . . .
H3 H 0.6612 0.0155 0.5557 0.027 Uiso 1 1 calc R U . . .
C4 C 0.66121(6) 0.05370(11) 0.77685(16) 0.0208(3) Uani 1 1 d . . . . .
C5 C 0.70007(6) 0.08477(10) 0.89746(15) 0.0180(3) Uani 1 1 d . . . . .
C6 C 0.76534(6) 0.09315(10) 0.87689(15) 0.0170(3) Uani 1 1 d . . . . .
C7 C 0.80241(7) 0.13167(11) 0.99880(15) 0.0194(3) Uani 1 1 d . . . . .
H7 H 0.8458 0.1396 0.9859 0.023 Uiso 1 1 calc R U . . .
C8 C 0.77699(7) 0.15694(11) 1.13162(16) 0.0201(3) Uani 1 1 d . . . . .
H8 H 0.8029 0.1825 1.2097 0.024 Uiso 1 1 calc R U . . .
C9 C 0.71184(7) 0.14600(11) 1.15725(15) 0.0200(3) Uani 1 1 d . . . . .
C10 C 0.67354(6) 0.11068(11) 1.03826(16) 0.0194(3) Uani 1 1 d . . . . .
C11 C 0.60842(7) 0.10266(12) 1.05782(17) 0.0239(3) Uani 1 1 d . . . . .
C12 C 0.58350(7) 0.12856(13) 1.19710(18) 0.0294(4) Uani 1 1 d . . . . .
H12 H 0.5401 0.1234 1.2118 0.035 Uiso 1 1 calc R U . . .
C13 C 0.62139(8) 0.16158(12) 1.31369(18) 0.0299(4) Uani 1 1 d . . . . .
H13 H 0.6037 0.1783 1.4075 0.036 Uiso 1 1 calc R U . . .
C14 C 0.68487(7) 0.17041(12) 1.29467(17) 0.0250(3) Uani 1 1 d . . . . .
H14 H 0.7102 0.1932 1.3755 0.03 Uiso 1 1 calc R U . . .
C15 C 0.57066(7) 0.07029(12) 0.93386(19) 0.0276(3) Uani 1 1 d . . . . .
H15 H 0.5271 0.0653 0.9459 0.033 Uiso 1 1 calc R U . . .
C16 C 0.59557(7) 0.04690(12) 0.80103(18) 0.0249(3) Uani 1 1 d . . . . .
H16 H 0.5693 0.0254 0.7213 0.03 Uiso 1 1 calc R U . . .
C17 C 0.85668(6) 0.07600(11) 0.70355(14) 0.0167(3) Uani 1 1 d . . . . .
C18 C 0.94133(6) 0.11938(10) 0.60359(14) 0.0155(3) Uani 1 1 d . . . . .
C19 C 0.95655(6) 0.04543(10) 0.70685(14) 0.0155(3) Uani 1 1 d . . . . .
C20 C 1.01887(6) 0.01603(10) 0.74002(14) 0.0161(3) Uani 1 1 d . . . . .
C21 C 1.04694(6) 0.14231(11) 0.53827(14) 0.0169(3) Uani 1 1 d . . . . .
C22 C 0.89205(7) -0.06758(11) 0.87647(15) 0.0207(3) Uani 1 1 d . . . . .
H22A H 0.8478 -0.0768 0.8951 0.031 Uiso 1 1 calc R U . . .
H22B H 0.9135 -0.0519 0.9708 0.031 Uiso 1 1 calc R U . . .
H22C H 0.909 -0.1311 0.8339 0.031 Uiso 1 1 calc R U . . .
C23 C 0.96840(7) 0.24540(11) 0.40753(16) 0.0216(3) Uani 1 1 d . . . . .
H23A H 0.9683 0.3134 0.4555 0.032 Uiso 1 1 calc R U . . .
H23B H 0.927 0.2305 0.3671 0.032 Uiso 1 1 calc R U . . .
H23C H 0.9985 0.2451 0.3261 0.032 Uiso 1 1 calc R U . . .
C24 C 1.12808(6) 0.05432(11) 0.67733(16) 0.0192(3) Uani 1 1 d . . . . .
H24A H 1.1479 0.0389 0.5804 0.023 Uiso 1 1 calc R U . . .
H24B H 1.1335 -0.0068 0.7426 0.023 Uiso 1 1 calc R U . . .
C25 C 1.16066(6) 0.14622(11) 0.74904(15) 0.0189(3) Uani 1 1 d . . . . .
H25A H 1.1374 0.1681 0.8385 0.023 Uiso 1 1 calc R U . . .
H25B H 1.1607 0.2046 0.6776 0.023 Uiso 1 1 calc R U . . .
C26 C 1.22715(6) 0.12113(11) 0.79458(16) 0.0211(3) Uani 1 1 d . . . . .
H26A H 1.2492 0.0935 0.7067 0.025 Uiso 1 1 calc R U . . .
H26B H 1.2267 0.0664 0.8719 0.025 Uiso 1 1 calc R U . . .
C27 C 1.26276(7) 0.21396(12) 0.85537(16) 0.0221(3) Uani 1 1 d . . . . .
H27A H 1.2672 0.2657 0.7747 0.026 Uiso 1 1 calc R U . . .
H27B H 1.2386 0.2461 0.9367 0.026 Uiso 1 1 calc R U . . .
C28 C 1.32678(7) 0.18548(12) 0.91508(18) 0.0250(3) Uani 1 1 d . . . . .
H28A H 1.3221 0.1382 1.0012 0.03 Uiso 1 1 calc R U . . .
H28B H 1.3495 0.1478 0.8363 0.03 Uiso 1 1 calc R U . . .
C29 C 1.36512(7) 0.27816(12) 0.96415(17) 0.0239(3) Uani 1 1 d . . . . .
H29A H 1.37 0.3252 0.8778 0.029 Uiso 1 1 calc R U . . .
H29B H 1.3423 0.3161 1.0423 0.029 Uiso 1 1 calc R U . . .
C30 C 1.42893(7) 0.25031(13) 1.0249(2) 0.0318(4) Uani 1 1 d . . . . .
H30A H 1.4241 0.204 1.1121 0.038 Uiso 1 1 calc R U . . .
H30B H 1.4517 0.2119 0.9472 0.038 Uiso 1 1 calc R U . . .
C31 C 1.46693(8) 0.34357(14) 1.0719(2) 0.0355(4) Uani 1 1 d . . . . .
H31A H 1.4746 0.3872 0.9846 0.053 Uiso 1 1 calc R U . . .
H31B H 1.5065 0.3205 1.1147 0.053 Uiso 1 1 calc R U . . .
H31C H 1.4442 0.3832 1.147 0.053 Uiso 1 1 calc R U . . .
N1 N 0.87991(5) 0.13955(9) 0.59919(12) 0.0178(3) Uani 1 1 d . . . . .
N2 N 0.90084(5) 0.01775(9) 0.77138(12) 0.0165(2) Uani 1 1 d . . . . .
N3 N 0.98540(5) 0.16663(9) 0.51766(12) 0.0175(2) Uani 1 1 d . . . . .
N4 N 1.06139(5) 0.07181(9) 0.65191(12) 0.0164(2) Uani 1 1 d . . . . .
O1 O 1.03630(5) -0.04776(8) 0.83272(11) 0.0215(2) Uani 1 1 d . . . . .
O2 O 1.08742(5) 0.18050(8) 0.46151(11) 0.0226(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.3965(19) . ?
C1 C6 1.4130(19) . ?
C1 C17 1.4748(19) . ?
C2 C3 1.380(2) . ?
C2 H2 0.95 . ?
C3 C4 1.394(2) . ?
C3 H3 0.95 . ?
C4 C5 1.419(2) . ?
C4 C16 1.439(2) . ?
C5 C6 1.4276(19) . ?
C5 C10 1.4283(19) . ?
C6 C7 1.4365(19) . ?
C7 C8 1.3534(19) . ?
C7 H7 0.95 . ?
C8 C9 1.435(2) . ?
C8 H8 0.95 . ?
C9 C14 1.4012(19) . ?
C9 C10 1.418(2) . ?
C10 C11 1.423(2) . ?
C11 C12 1.402(2) . ?
C11 C15 1.433(2) . ?
C12 C13 1.388(2) . ?
C12 H12 0.95 . ?
C13 C14 1.388(2) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
C15 C16 1.343(2) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C17 N1 1.3451(18) . ?
C17 N2 1.3555(18) . ?
C18 N1 1.3523(17) . ?
C18 C19 1.3687(19) . ?
C18 N3 1.3728(17) . ?
C19 N2 1.3863(17) . ?
C19 C20 1.4277(19) . ?
C20 O1 1.2274(16) . ?
C20 N4 1.4140(17) . ?
C21 O2 1.2211(16) . ?
C21 N3 1.3769(17) . ?
C21 N4 1.3997(17) . ?
C22 N2 1.4645(17) . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C23 N3 1.4629(17) . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
C24 N4 1.4737(17) . ?
C24 C25 1.5219(19) . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C25 C26 1.5242(19) . ?
C25 H25A 0.99 . ?
C25 H25B 0.99 . ?
C26 C27 1.525(2) . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?
C27 C28 1.523(2) . ?
C27 H27A 0.99 . ?
C27 H27B 0.99 . ?
C28 C29 1.521(2) . ?
C28 H28A 0.99 . ?
C28 H28B 0.99 . ?
C29 C30 1.520(2) . ?
C29 H29A 0.99 . ?
C29 H29B 0.99 . ?
C30 C31 1.518(2) . ?
C30 H30A 0.99 . ?
C30 H30B 0.99 . ?
C31 H31A 0.98 . ?
C31 H31B 0.98 . ?
C31 H31C 0.98 . ?

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 119.91(13) . . ?
C2 C1 C17 117.72(12) . . ?
C6 C1 C17 122.31(12) . . ?
C3 C2 C1 121.38(13) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 120.54(13) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 119.42(13) . . ?
C3 C4 C16 121.85(14) . . ?
C5 C4 C16 118.69(13) . . ?
C4 C5 C6 120.11(12) . . ?
C4 C5 C10 119.84(13) . . ?
C6 C5 C10 120.02(13) . . ?
C1 C6 C5 118.56(12) . . ?
C1 C6 C7 123.10(12) . . ?
C5 C6 C7 118.23(12) . . ?
C8 C7 C6 121.51(13) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 121.49(13) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C14 C9 C10 119.14(13) . . ?
C14 C9 C8 122.27(14) . . ?
C10 C9 C8 118.58(12) . . ?
C9 C10 C11 120.14(13) . . ?
C9 C10 C5 120.11(12) . . ?
C11 C10 C5 119.74(13) . . ?
C12 C11 C10 118.66(14) . . ?
C12 C11 C15 122.47(14) . . ?
C10 C11 C15 118.86(14) . . ?
C13 C12 C11 120.86(14) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.67(14) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 120.52(15) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C16 C15 C11 121.37(14) . . ?
C16 C15 H15 119.3 . . ?
C11 C15 H15 119.3 . . ?
C15 C16 C4 121.47(15) . . ?
C15 C16 H16 119.3 . . ?
C4 C16 H16 119.3 . . ?
N1 C17 N2 112.69(12) . . ?
N1 C17 C1 122.72(12) . . ?
N2 C17 C1 124.55(12) . . ?
N1 C18 C19 112.61(12) . . ?
N1 C18 N3 125.63(12) . . ?
C19 C18 N3 121.75(12) . . ?
C18 C19 N2 104.94(12) . . ?
C18 C19 C20 123.18(12) . . ?
N2 C19 C20 131.67(12) . . ?
O1 C20 N4 121.58(12) . . ?
O1 C20 C19 127.08(13) . . ?
N4 C20 C19 111.33(12) . . ?
O2 C21 N3 121.81(13) . . ?
O2 C21 N4 121.10(13) . . ?
N3 C21 N4 117.09(12) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N4 C24 C25 113.11(11) . . ?
N4 C24 H24A 109 . . ?
C25 C24 H24A 109 . . ?
N4 C24 H24B 109 . . ?
C25 C24 H24B 109 . . ?
H24A C24 H24B 107.8 . . ?
C24 C25 C26 112.15(12) . . ?
C24 C25 H25A 109.2 . . ?
C26 C25 H25A 109.2 . . ?
C24 C25 H25B 109.2 . . ?
C26 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C25 C26 C27 113.47(12) . . ?
C25 C26 H26A 108.9 . . ?
C27 C26 H26A 108.9 . . ?
C25 C26 H26B 108.9 . . ?
C27 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
C28 C27 C26 112.80(12) . . ?
C28 C27 H27A 109 . . ?
C26 C27 H27A 109 . . ?
C28 C27 H27B 109 . . ?
C26 C27 H27B 109 . . ?
H27A C27 H27B 107.8 . . ?
C29 C28 C27 113.59(13) . . ?
C29 C28 H28A 108.8 . . ?
C27 C28 H28A 108.8 . . ?
C29 C28 H28B 108.8 . . ?
C27 C28 H28B 108.8 . . ?
H28A C28 H28B 107.7 . . ?
C30 C29 C28 113.91(13) . . ?
C30 C29 H29A 108.8 . . ?
C28 C29 H29A 108.8 . . ?
C30 C29 H29B 108.8 . . ?
C28 C29 H29B 108.8 . . ?
H29A C29 H29B 107.7 . . ?
C31 C30 C29 113.36(14) . . ?
C31 C30 H30A 108.9 . . ?
C29 C30 H30A 108.9 . . ?
C31 C30 H30B 108.9 . . ?
C29 C30 H30B 108.9 . . ?
H30A C30 H30B 107.7 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C17 N1 C18 103.50(11) . . ?
C17 N2 C19 106.24(11) . . ?
C17 N2 C22 127.79(12) . . ?
C19 N2 C22 125.48(12) . . ?
C18 N3 C21 119.76(11) . . ?
C18 N3 C23 121.12(11) . . ?
C21 N3 C23 119.08(11) . . ?
C21 N4 C20 126.61(11) . . ?
C21 N4 C24 115.07(11) . . ?
C20 N4 C24 118.31(11) . . ?


#----------------------------------------------------------------------------#
#                   SQUEEZE DETAILS                                          #
#----------------------------------------------------------------------------#



# END of CIF
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1956527'
loop_
_audit_author_name
_audit_author_address
'Werner Kaminsky'
;University of Washington
United States of America
;
_audit_update_record             
;
2019-11-01 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;

_audit_creation_date             2018-07-23T12:56:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C76 H98 N16 O8'
_chemical_formula_sum            'C76 H98 N16 O8'
_chemical_formula_weight         1363.7

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4759(7)
_cell_length_b                   23.1694(15)
_cell_length_c                   14.5016(10)
_cell_angle_alpha                90
_cell_angle_beta                 111.004(3)
_cell_angle_gamma                90
_cell_volume                     3599.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9644
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.77
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1460

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_T_max  0.74
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.994

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      0.042356
_diffrn_orient_matrix_ub_12      0.038205
_diffrn_orient_matrix_ub_13      0.004937
_diffrn_orient_matrix_ub_21      -0.035678
_diffrn_orient_matrix_ub_22      0.012835
_diffrn_orient_matrix_ub_23      0.050211
_diffrn_orient_matrix_ub_31      0.075137
_diffrn_orient_matrix_ub_32      -0.015442
_diffrn_orient_matrix_ub_33      0.05395
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_number            17739
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.742
_diffrn_reflns_theta_max         28.352
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             8986
_reflns_number_gt                6153
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+1.3141P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8986
_refine_ls_number_parameters     457
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1212
_refine_ls_wR_factor_gt          0.104
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.051

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.65414(13) 0.91480(6) 0.70883(10) 0.0167(3) Uani 1 1 d . . . . .
H1 H 0.6973 0.8916 0.7647 0.02 Uiso 1 1 calc R U . . .
C2 C 0.57399(13) 0.88832(6) 0.62343(10) 0.0161(3) Uani 1 1 d . . . . .
C3 C 0.51150(12) 0.92195(6) 0.53858(10) 0.0148(3) Uani 1 1 d . . . . .
C4 C 0.53074(12) 0.98274(6) 0.54282(10) 0.0142(3) Uani 1 1 d . . . . .
C5 C 0.61101(12) 1.00932(6) 0.63176(10) 0.0146(3) Uani 1 1 d . . . . .
C6 C 0.67277(13) 0.97420(6) 0.71466(10) 0.0155(3) Uani 1 1 d . . . . .
C7 C 0.62456(13) 1.07091(6) 0.63386(10) 0.0161(3) Uani 1 1 d . . . . .
H7 H 0.6744 1.0893 0.6935 0.019 Uiso 1 1 calc R U . . .
C8 C 0.43228(13) 0.89660(6) 0.44751(10) 0.0169(3) Uani 1 1 d . . . . .
H8 H 0.4194 0.856 0.4442 0.02 Uiso 1 1 calc R U . . .
C9 C 0.55583(13) 0.82528(6) 0.62319(10) 0.0157(3) Uani 1 1 d . . . . .
C10 C 0.78561(13) 0.79866(7) 0.67552(11) 0.0200(3) Uani 1 1 d . . . . .
H10A H 0.7975 0.8342 0.6434 0.03 Uiso 1 1 calc R U . . .
H10B H 0.8255 0.7664 0.6545 0.03 Uiso 1 1 calc R U . . .
H10C H 0.8233 0.8031 0.7474 0.03 Uiso 1 1 calc R U . . .
C11 C 0.47337(13) 0.74268(6) 0.61674(10) 0.0167(3) Uani 1 1 d . . . . .
C12 C 0.59896(13) 0.73297(6) 0.64342(10) 0.0166(3) Uani 1 1 d . . . . .
C13 C 0.65406(14) 0.67700(7) 0.66224(11) 0.0188(3) Uani 1 1 d . . . . .
C14 C 0.43651(14) 0.64233(7) 0.63134(11) 0.0211(3) Uani 1 1 d . . . . .
C15 C 0.25714(14) 0.70785(8) 0.58270(12) 0.0264(4) Uani 1 1 d . . . . .
H15A H 0.2398 0.7493 0.5746 0.04 Uiso 1 1 calc R U . . .
H15B H 0.2311 0.6929 0.6355 0.04 Uiso 1 1 calc R U . . .
H15C H 0.2109 0.6879 0.5208 0.04 Uiso 1 1 calc R U . . .
C16 C 0.61299(16) 0.57499(7) 0.68362(12) 0.0246(3) Uani 1 1 d . . . . .
H16A H 0.6816 0.5675 0.659 0.03 Uiso 1 1 calc R U . . .
H16B H 0.5457 0.5467 0.6522 0.03 Uiso 1 1 calc R U . . .
C17 C 0.66089(15) 0.56676(7) 0.79531(11) 0.0235(3) Uani 1 1 d . . . . .
H17A H 0.5919 0.574 0.8197 0.028 Uiso 1 1 calc R U . . .
H17B H 0.7274 0.5954 0.8266 0.028 Uiso 1 1 calc R U . . .
C18 C 0.71242(16) 0.50621(7) 0.82601(12) 0.0265(4) Uani 1 1 d . . . . .
H18A H 0.7707 0.4964 0.7919 0.032 Uiso 1 1 calc R U . . .
H18B H 0.6427 0.4782 0.8044 0.032 Uiso 1 1 calc R U . . .
C20 C 0.78059(15) 0.50038(7) 0.93734(12) 0.0258(4) Uani 1 1 d . . . . .
H20A H 0.8471 0.53 0.9593 0.031 Uiso 1 1 calc R U . . .
H20B H 0.7209 0.5083 0.971 0.031 Uiso 1 1 calc R U . . .
C21 C 0.83891(16) 0.44105(8) 0.96937(12) 0.0281(4) Uani 1 1 d . . . . .
H21A H 0.8919 0.4313 0.9307 0.034 Uiso 1 1 calc R U . . .
H21B H 0.7716 0.4119 0.9541 0.034 Uiso 1 1 calc R U . . .
C23 C 0.91809(16) 0.43792(8) 1.07945(13) 0.0311(4) Uani 1 1 d . . . . .
H23A H 0.9818 0.4688 1.0953 0.037 Uiso 1 1 calc R U . . .
H23B H 0.8637 0.4455 1.1179 0.037 Uiso 1 1 calc R U . . .
C24 C 0.98346(17) 0.38050(9) 1.11202(14) 0.0384(5) Uani 1 1 d . . . . .
H24A H 1.0272 0.37 1.0667 0.046 Uiso 1 1 calc R U . . .
H24B H 1.0474 0.3851 1.1789 0.046 Uiso 1 1 calc R U . . .
C25 C 0.8972(2) 0.33176(9) 1.11411(16) 0.0489(6) Uani 1 1 d . . . . .
H25A H 0.8565 0.3409 1.1613 0.073 Uiso 1 1 calc R U . . .
H25B H 0.9454 0.296 1.1342 0.073 Uiso 1 1 calc R U . . .
H25C H 0.8336 0.3267 1.0481 0.073 Uiso 1 1 calc R U . . .
C26 C 0.75543(13) 0.99979(6) 0.80823(10) 0.0155(3) Uani 1 1 d . . . . .
C27 C 0.89111(12) 1.05153(6) 0.91356(10) 0.0159(3) Uani 1 1 d . . . . .
C28 C 0.83608(13) 1.01987(6) 0.96594(10) 0.0161(3) Uani 1 1 d . . . . .
C29 C 0.86137(13) 1.02837(7) 1.06837(11) 0.0181(3) Uani 1 1 d . . . . .
C30 C 1.01363(13) 1.10343(6) 1.05685(10) 0.0176(3) Uani 1 1 d . . . . .
C31 C 1.04144(14) 1.12444(7) 0.89993(11) 0.0227(3) Uani 1 1 d . . . . .
H31A H 1.0873 1.1573 0.9385 0.034 Uiso 1 1 calc R U . . .
H31B H 0.9778 1.1384 0.8388 0.034 Uiso 1 1 calc R U . . .
H31C H 1.0995 1.0989 0.8838 0.034 Uiso 1 1 calc R U . . .
C32 C 0.65474(14) 0.95063(7) 0.91763(11) 0.0221(3) Uani 1 1 d . . . . .
H32A H 0.5796 0.9478 0.858 0.033 Uiso 1 1 calc R U . . .
H32B H 0.6333 0.9683 0.9709 0.033 Uiso 1 1 calc R U . . .
H32C H 0.6889 0.9119 0.9378 0.033 Uiso 1 1 calc R U . . .
C33 C 0.97749(14) 1.08906(7) 1.21135(11) 0.0224(3) Uani 1 1 d . . . . .
H33A H 1.0682 1.0959 1.2441 0.027 Uiso 1 1 calc R U . . .
H33B H 0.9538 1.0571 1.2464 0.027 Uiso 1 1 calc R U . . .
C34 C 0.90621(15) 1.14346(7) 1.21859(12) 0.0264(4) Uani 1 1 d . . . . .
H34A H 0.9303 1.1752 1.1833 0.032 Uiso 1 1 calc R U . . .
H34B H 0.9314 1.1547 1.2889 0.032 Uiso 1 1 calc R U . . .
C35 C 0.76431(15) 1.13634(7) 1.17562(12) 0.0258(4) Uani 1 1 d . . . . .
H35A H 0.7401 1.1214 1.1073 0.031 Uiso 1 1 calc R U . . .
H35B H 0.7397 1.1071 1.215 0.031 Uiso 1 1 calc R U . . .
C36 C 0.69209(15) 1.19178(7) 1.17374(12) 0.0272(4) Uani 1 1 d . . . . .
H36A H 0.7118 1.2203 1.1306 0.033 Uiso 1 1 calc R U . . .
H36B H 0.7193 1.2081 1.2413 0.033 Uiso 1 1 calc R U . . .
C37 C 0.55116(15) 1.18186(7) 1.13621(12) 0.0256(4) Uani 1 1 d . . . . .
H37A H 0.5262 1.1616 1.072 0.031 Uiso 1 1 calc R U . . .
H37B H 0.5315 1.1562 1.1832 0.031 Uiso 1 1 calc R U . . .
C38 C 0.47338(15) 1.23646(7) 1.12304(12) 0.0253(4) Uani 1 1 d . . . . .
H38A H 0.4904 1.2617 1.0743 0.03 Uiso 1 1 calc R U . . .
H38B H 0.4993 1.2574 1.1867 0.03 Uiso 1 1 calc R U . . .
C39 C 0.33360(15) 1.22456(7) 1.08839(13) 0.0276(4) Uani 1 1 d . . . . .
H39A H 0.3075 1.205 1.0234 0.033 Uiso 1 1 calc R U . . .
H39B H 0.3176 1.1977 1.1356 0.033 Uiso 1 1 calc R U . . .
C40 C 0.25367(18) 1.27812(8) 1.07897(13) 0.0375(5) Uani 1 1 d . . . . .
H40A H 0.2721 1.2954 1.1443 0.056 Uiso 1 1 calc R U . . .
H40B H 0.1652 1.2674 1.0512 0.056 Uiso 1 1 calc R U . . .
H40C H 0.2722 1.306 1.0353 0.056 Uiso 1 1 calc R U . . .
N1 N 0.65169(11) 0.78701(5) 0.64746(8) 0.0156(3) Uani 1 1 d . . . . .
N2 N 0.44423(11) 0.79953(5) 0.60316(9) 0.0174(3) Uani 1 1 d . . . . .
N3 N 0.39094(11) 0.69796(5) 0.60832(9) 0.0195(3) Uani 1 1 d . . . . .
N4 N 0.56457(12) 0.63409(5) 0.65554(9) 0.0205(3) Uani 1 1 d . . . . .
N5 N 0.74755(11) 0.98612(5) 0.89706(9) 0.0160(3) Uani 1 1 d . . . . .
N6 N 0.84413(11) 1.03914(5) 0.81582(8) 0.0163(3) Uani 1 1 d . . . . .
N7 N 0.98114(11) 1.09247(5) 0.95777(8) 0.0175(3) Uani 1 1 d . . . . .
N8 N 0.95063(11) 1.07236(6) 1.10750(8) 0.0180(3) Uani 1 1 d . . . . .
O1 O 0.76447(10) 0.66509(5) 0.68285(8) 0.0247(3) Uani 1 1 d . . . . .
O2 O 0.36627(11) 0.60248(5) 0.62968(9) 0.0305(3) Uani 1 1 d . . . . .
O3 O 0.81348(10) 1.00285(5) 1.11976(8) 0.0247(3) Uani 1 1 d . . . . .
O4 O 1.09381(9) 1.13904(5) 1.09963(8) 0.0224(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C6 1.391(2) . ?
C1 C2 1.3926(19) . ?
C1 H1 0.95 . ?
C2 C3 1.4151(19) . ?
C2 C9 1.475(2) . ?
C3 C4 1.424(2) . ?
C3 C8 1.4335(19) . ?
C4 C5 1.4281(18) . ?
C4 C4 1.432(3) 3_676 ?
C5 C6 1.4140(19) . ?
C5 C7 1.435(2) . ?
C6 C26 1.4730(19) . ?
C7 C8 1.354(2) 3_676 ?
C7 H7 0.95 . ?
C8 C7 1.354(2) 3_676 ?
C8 H8 0.95 . ?
C9 N2 1.3468(18) . ?
C9 N1 1.3575(18) . ?
C10 N1 1.4670(18) . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 N2 1.3558(19) . ?
C11 C12 1.370(2) . ?
C11 N3 1.3786(19) . ?
C12 N1 1.3827(19) . ?
C12 C13 1.425(2) . ?
C13 O1 1.2245(18) . ?
C13 N4 1.408(2) . ?
C14 O2 1.2202(19) . ?
C14 N3 1.386(2) . ?
C14 N4 1.396(2) . ?
C15 N3 1.463(2) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 N4 1.4791(19) . ?
C16 C17 1.524(2) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 C18 1.526(2) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 C20 1.527(2) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C20 C21 1.527(2) . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C21 C23 1.530(2) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C23 C24 1.517(3) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 C25 1.510(3) . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C25 H25C 0.98 . ?
C26 N6 1.3413(19) . ?
C26 N5 1.3607(19) . ?
C27 N6 1.3543(18) . ?
C27 C28 1.363(2) . ?
C27 N7 1.3797(18) . ?
C28 N5 1.3834(17) . ?
C28 C29 1.421(2) . ?
C29 O3 1.2250(18) . ?
C29 N8 1.4118(19) . ?
C30 O4 1.2260(17) . ?
C30 N7 1.3726(18) . ?
C30 N8 1.400(2) . ?
C31 N7 1.465(2) . ?
C31 H31A 0.98 . ?
C31 H31B 0.98 . ?
C31 H31C 0.98 . ?
C32 N5 1.458(2) . ?
C32 H32A 0.98 . ?
C32 H32B 0.98 . ?
C32 H32C 0.98 . ?
C33 N8 1.4766(18) . ?
C33 C34 1.526(2) . ?
C33 H33A 0.99 . ?
C33 H33B 0.99 . ?
C34 C35 1.530(2) . ?
C34 H34A 0.99 . ?
C34 H34B 0.99 . ?
C35 C36 1.524(2) . ?
C35 H35A 0.99 . ?
C35 H35B 0.99 . ?
C36 C37 1.528(2) . ?
C36 H36A 0.99 . ?
C36 H36B 0.99 . ?
C37 C38 1.520(2) . ?
C37 H37A 0.99 . ?
C37 H37B 0.99 . ?
C38 C39 1.524(2) . ?
C38 H38A 0.99 . ?
C38 H38B 0.99 . ?
C39 C40 1.520(2) . ?
C39 H39A 0.99 . ?
C39 H39B 0.99 . ?
C40 H40A 0.98 . ?
C40 H40B 0.98 . ?
C40 H40C 0.98 . ?

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 C1 C2 121.87(13) . . ?
C6 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C1 C2 C3 119.87(13) . . ?
C1 C2 C9 119.07(13) . . ?
C3 C2 C9 121.06(12) . . ?
C2 C3 C4 119.00(12) . . ?
C2 C3 C8 122.13(13) . . ?
C4 C3 C8 118.84(12) . . ?
C3 C4 C5 120.36(12) . . ?
C3 C4 C4 119.63(15) . 3_676 ?
C5 C4 C4 120.01(16) . 3_676 ?
C6 C5 C4 118.96(13) . . ?
C6 C5 C7 122.48(13) . . ?
C4 C5 C7 118.56(12) . . ?
C1 C6 C5 119.91(12) . . ?
C1 C6 C26 119.24(12) . . ?
C5 C6 C26 120.84(13) . . ?
C8 C7 C5 121.32(13) 3_676 . ?
C8 C7 H7 119.3 3_676 . ?
C5 C7 H7 119.3 . . ?
C7 C8 C3 121.57(14) 3_676 . ?
C7 C8 H8 119.2 3_676 . ?
C3 C8 H8 119.2 . . ?
N2 C9 N1 112.71(13) . . ?
N2 C9 C2 124.18(13) . . ?
N1 C9 C2 123.05(13) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 112.35(13) . . ?
N2 C11 N3 126.26(13) . . ?
C12 C11 N3 121.37(13) . . ?
C11 C12 N1 105.27(12) . . ?
C11 C12 C13 123.57(13) . . ?
N1 C12 C13 131.16(13) . . ?
O1 C13 N4 121.54(14) . . ?
O1 C13 C12 126.94(14) . . ?
N4 C13 C12 111.51(13) . . ?
O2 C14 N3 120.62(14) . . ?
O2 C14 N4 122.00(14) . . ?
N3 C14 N4 117.38(13) . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 C17 111.41(13) . . ?
N4 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N4 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108 . . ?
C16 C17 C18 112.30(13) . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 C20 112.83(14) . . ?
C17 C18 H18A 109 . . ?
C20 C18 H18A 109 . . ?
C17 C18 H18B 109 . . ?
C20 C18 H18B 109 . . ?
H18A C18 H18B 107.8 . . ?
C21 C20 C18 113.83(14) . . ?
C21 C20 H20A 108.8 . . ?
C18 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C18 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 C23 113.07(15) . . ?
C20 C21 H21A 109 . . ?
C23 C21 H21A 109 . . ?
C20 C21 H21B 109 . . ?
C23 C21 H21B 109 . . ?
H21A C21 H21B 107.8 . . ?
C24 C23 C21 114.14(16) . . ?
C24 C23 H23A 108.7 . . ?
C21 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
C21 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C25 C24 C23 114.04(16) . . ?
C25 C24 H24A 108.7 . . ?
C23 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
C23 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N6 C26 N5 112.73(12) . . ?
N6 C26 C6 124.64(13) . . ?
N5 C26 C6 122.62(13) . . ?
N6 C27 C28 112.27(12) . . ?
N6 C27 N7 125.66(13) . . ?
C28 C27 N7 122.04(13) . . ?
C27 C28 N5 105.59(12) . . ?
C27 C28 C29 123.09(13) . . ?
N5 C28 C29 130.91(14) . . ?
O3 C29 N8 121.53(13) . . ?
O3 C29 C28 126.93(14) . . ?
N8 C29 C28 111.53(13) . . ?
O4 C30 N7 121.81(14) . . ?
O4 C30 N8 121.03(13) . . ?
N7 C30 N8 117.15(12) . . ?
N7 C31 H31A 109.5 . . ?
N7 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N7 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N5 C32 H32A 109.5 . . ?
N5 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N5 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N8 C33 C34 111.44(12) . . ?
N8 C33 H33A 109.3 . . ?
C34 C33 H33A 109.3 . . ?
N8 C33 H33B 109.3 . . ?
C34 C33 H33B 109.3 . . ?
H33A C33 H33B 108 . . ?
C33 C34 C35 113.67(13) . . ?
C33 C34 H34A 108.8 . . ?
C35 C34 H34A 108.8 . . ?
C33 C34 H34B 108.8 . . ?
C35 C34 H34B 108.8 . . ?
H34A C34 H34B 107.7 . . ?
C36 C35 C34 114.16(14) . . ?
C36 C35 H35A 108.7 . . ?
C34 C35 H35A 108.7 . . ?
C36 C35 H35B 108.7 . . ?
C34 C35 H35B 108.7 . . ?
H35A C35 H35B 107.6 . . ?
C35 C36 C37 112.29(14) . . ?
C35 C36 H36A 109.1 . . ?
C37 C36 H36A 109.1 . . ?
C35 C36 H36B 109.1 . . ?
C37 C36 H36B 109.1 . . ?
H36A C36 H36B 107.9 . . ?
C38 C37 C36 114.74(14) . . ?
C38 C37 H37A 108.6 . . ?
C36 C37 H37A 108.6 . . ?
C38 C37 H37B 108.6 . . ?
C36 C37 H37B 108.6 . . ?
H37A C37 H37B 107.6 . . ?
C37 C38 C39 113.07(14) . . ?
C37 C38 H38A 109 . . ?
C39 C38 H38A 109 . . ?
C37 C38 H38B 109 . . ?
C39 C38 H38B 109 . . ?
H38A C38 H38B 107.8 . . ?
C40 C39 C38 114.31(15) . . ?
C40 C39 H39A 108.7 . . ?
C38 C39 H39A 108.7 . . ?
C40 C39 H39B 108.7 . . ?
C38 C39 H39B 108.7 . . ?
H39A C39 H39B 107.6 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C9 N1 C12 106.19(12) . . ?
C9 N1 C10 128.52(13) . . ?
C12 N1 C10 125.27(12) . . ?
C9 N2 C11 103.48(12) . . ?
C11 N3 C14 119.33(12) . . ?
C11 N3 C15 121.96(13) . . ?
C14 N3 C15 118.56(13) . . ?
C14 N4 C13 126.65(13) . . ?
C14 N4 C16 116.96(13) . . ?
C13 N4 C16 116.25(12) . . ?
C26 N5 C28 105.74(12) . . ?
C26 N5 C32 128.76(12) . . ?
C28 N5 C32 124.90(12) . . ?
C26 N6 C27 103.64(12) . . ?
C30 N7 C27 119.39(13) . . ?
C30 N7 C31 119.93(12) . . ?
C27 N7 C31 120.68(12) . . ?
C30 N8 C29 126.65(12) . . ?
C30 N8 C33 116.23(12) . . ?
C29 N8 C33 117.08(12) . . ?


#----------------------------------------------------------------------------#
#                   SQUEEZE DETAILS                                          #
#----------------------------------------------------------------------------#



# END of CIF
