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

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

data_Karb_5c
_database_code_depnum_ccdc_archive 'CCDC 1826922'
_audit_update_record             
;
2018-06-19 deposited with the CCDC.
2018-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H27 N3 O2'
_chemical_formula_weight         365.46

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0402(17)
_cell_length_b                   9.8828(18)
_cell_length_c                   13.696(2)
_cell_angle_alpha                99.883(15)
_cell_angle_beta                 90.997(15)
_cell_angle_gamma                109.551(18)
_cell_volume                     1007.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3000
_cell_measurement_theta_min      3
_cell_measurement_theta_max      20

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.890
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
;
CrysAlis RED
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  KM4CCD
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 8.6479
_diffrn_reflns_number            7811
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.697
_diffrn_reflns_theta_max         25.200
_diffrn_reflns_theta_full        25.200
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3617
_reflns_number_gt                1704
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       CrysAlisCCD
_computing_cell_refinement       CrysAlisRED
_computing_data_reduction        CrysAlisRED
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  'XCIF (Bruker AXS Inc., 2013)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0886P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3617
_refine_ls_number_parameters     308
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1717
_refine_ls_wR_factor_gt          0.1226
_refine_ls_goodness_of_fit_ref   0.888
_refine_ls_restrained_S_all      0.888
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2193(4) 0.5181(3) 0.1131(2) 0.0455(7) Uani 1 1 d . . . . .
C2 C -0.2995(4) 0.4351(3) 0.1815(2) 0.0567(8) Uani 1 1 d . . . . .
C3 C -0.2714(5) 0.4890(3) 0.2825(3) 0.0685(10) Uani 1 1 d . . . . .
C4 C -0.1613(5) 0.6295(4) 0.3198(3) 0.0643(9) Uani 1 1 d . . . . .
C4A C -0.0757(4) 0.7159(3) 0.2524(2) 0.0513(7) Uani 1 1 d . . . . .
C4B C 0.0526(4) 0.8617(3) 0.2644(2) 0.0509(7) Uani 1 1 d . . . . .
C5 C 0.1276(4) 0.9698(3) 0.3475(3) 0.0640(9) Uani 1 1 d . . . . .
C6 C 0.2425(5) 1.1030(4) 0.3318(3) 0.0699(10) Uani 1 1 d . . . . .
C7 C 0.2807(4) 1.1286(3) 0.2367(3) 0.0610(9) Uani 1 1 d . . . . .
C8 C 0.2083(4) 1.0229(3) 0.1529(2) 0.0492(7) Uani 1 1 d . . . . .
C8A C 0.0923(4) 0.8871(3) 0.1675(2) 0.0466(7) Uani 1 1 d . . . . .
N9 N -0.0034(3) 0.7650(2) 0.09909(19) 0.0462(6) Uani 1 1 d . . . . .
C9A C -0.1068(3) 0.6604(3) 0.1498(2) 0.0455(7) Uani 1 1 d . . . . .
N10 N -0.2465(3) 0.4529(3) 0.01092(18) 0.0489(6) Uani 1 1 d . . . . .
C11 C -0.2817(4) 0.5111(3) -0.0653(2) 0.0501(7) Uani 1 1 d . . . . .
O11 O -0.2776(3) 0.63849(19) -0.05306(15) 0.0685(7) Uani 1 1 d . . . . .
C12 C -0.3256(4) 0.4136(3) -0.1653(2) 0.0579(8) Uani 1 1 d . . . . .
H12A H -0.453346 0.374332 -0.178689 0.069 Uiso 1 1 calc R U . A 1
H12B H -0.284839 0.332039 -0.163721 0.069 Uiso 1 1 calc R U . A 1
C13A C -0.2464(5) 0.4873(3) -0.2488(2) 0.0769(10) Uani 0.907(11) 1 d D . P B 1
H13A H -0.118567 0.515514 -0.240195 0.092 Uiso 0.907(11) 1 calc R U P B 1
H13B H -0.274971 0.575793 -0.245657 0.092 Uiso 0.907(11) 1 calc R U P B 1
C14A C -0.3110(12) 0.3917(6) -0.3506(3) 0.0876(19) Uani 0.907(11) 1 d D . P B 1
H14A H -0.439357 0.358255 -0.358106 0.105 Uiso 0.907(11) 1 calc R U P B 1
H14B H -0.275140 0.306459 -0.355978 0.105 Uiso 0.907(11) 1 calc R U P B 1
C15A C -0.2368(13) 0.4744(7) -0.4337(4) 0.150(4) Uani 0.907(11) 1 d D . P B 1
H15A H -0.110475 0.518510 -0.421556 0.224 Uiso 0.907(11) 1 calc R U P B 1
H15B H -0.287772 0.549070 -0.435392 0.224 Uiso 0.907(11) 1 calc R U P B 1
H15C H -0.265385 0.407539 -0.496279 0.224 Uiso 0.907(11) 1 calc R U P B 1
C13B C -0.2464(5) 0.4873(3) -0.2488(2) 0.0769(10) Uani 0.093(11) 1 d D . P B 2
H13C H -0.125241 0.544603 -0.223619 0.092 Uiso 0.093(11) 1 calc R U P B 2
H13D H -0.305180 0.557718 -0.252451 0.092 Uiso 0.093(11) 1 calc R U P B 2
C14B C -0.233(6) 0.425(8) -0.3571(18) 0.09(2) Uiso 0.093(11) 1 d D . P B 2
H14C H -0.128647 0.489308 -0.381205 0.104 Uiso 0.093(11) 1 calc R U P B 2
H14D H -0.219254 0.330346 -0.361250 0.104 Uiso 0.093(11) 1 calc R U P B 2
C15B C -0.395(6) 0.408(5) -0.422(3) 0.079(16) Uiso 0.093(11) 1 d D . P B 2
H15D H -0.485286 0.316302 -0.420355 0.119 Uiso 0.093(11) 1 calc R U P B 2
H15E H -0.364415 0.411983 -0.489427 0.119 Uiso 0.093(11) 1 calc R U P B 2
H15F H -0.438699 0.486395 -0.398382 0.119 Uiso 0.093(11) 1 calc R U P B 2
N16 N 0.2429(3) 1.0594(2) 0.05756(19) 0.0513(7) Uani 1 1 d . . . . .
C17 C 0.2773(3) 0.9768(3) -0.0229(2) 0.0487(7) Uani 1 1 d . . . . .
O17 O 0.2717(3) 0.85067(19) -0.02220(15) 0.0632(6) Uani 1 1 d . . . . .
C18 C 0.3270(5) 1.0468(3) -0.1114(2) 0.0578(9) Uani 1 1 d . . . . .
C19 C 0.2709(6) 0.9459(4) -0.2102(3) 0.0681(10) Uani 1 1 d . . . . .
C20 C 0.3423(5) 1.0151(4) -0.2971(3) 0.0811(11) Uani 1 1 d . . . . .
H20A H 0.470568 1.053193 -0.287601 0.097 Uiso 1 1 calc R U . . .
H20B H 0.302174 1.097146 -0.298287 0.097 Uiso 1 1 calc R U . . .
C21 C 0.2881(7) 0.9131(5) -0.3959(3) 0.1264(17) Uani 1 1 d . . . . .
H21A H 0.336882 0.836430 -0.397961 0.190 Uiso 1 1 calc R U . . .
H21B H 0.331363 0.966238 -0.448053 0.190 Uiso 1 1 calc R U . . .
H21C H 0.161235 0.871483 -0.404924 0.190 Uiso 1 1 calc R U . . .
H2 H -0.376(3) 0.334(3) 0.1571(18) 0.055(8) Uiso 1 1 d . . . . .
H3 H -0.331(4) 0.430(3) 0.333(2) 0.070(9) Uiso 1 1 d . . . . .
H4 H -0.136(4) 0.671(3) 0.393(2) 0.066(9) Uiso 1 1 d . . . . .
H5 H 0.099(4) 0.955(3) 0.424(2) 0.083(10) Uiso 1 1 d . . . . .
H6 H 0.298(4) 1.178(3) 0.395(2) 0.075(9) Uiso 1 1 d . . . . .
H7 H 0.366(4) 1.228(3) 0.224(2) 0.077(9) Uiso 1 1 d . . . . .
H9 H 0.003(4) 0.757(3) 0.031(2) 0.071(10) Uiso 1 1 d . . . . .
H10 H -0.275(3) 0.361(3) 0.0014(18) 0.050(8) Uiso 1 1 d . . . . .
H16 H 0.270(3) 1.155(3) 0.0525(19) 0.062(8) Uiso 1 1 d . . . . .
H18A H 0.457(5) 1.091(4) -0.098(2) 0.093(12) Uiso 1 1 d . . . . .
H18B H 0.298(3) 1.130(3) -0.1059(19) 0.054(8) Uiso 1 1 d . . . . .
H19A H 0.306(4) 0.861(4) -0.207(2) 0.090(11) Uiso 1 1 d . . . . .
H19B H 0.148(5) 0.908(3) -0.217(2) 0.074(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 1.377(4) . ?
C1 C9A 1.392(3) . ?
C1 N10 1.416(3) . ?
C2 C3 1.380(4) . ?
C2 H2 0.98(3) . ?
C3 C4 1.375(4) . ?
C3 H3 1.01(3) . ?
C4 C4A 1.399(4) . ?
C4 H4 1.00(3) . ?
C4A C9A 1.403(4) . ?
C4A C4B 1.444(4) . ?
C4B C5 1.389(4) . ?
C4B C8A 1.415(4) . ?
C5 C6 1.386(4) . ?
C5 H5 1.10(3) . ?
C6 C7 1.390(4) . ?
C6 H6 1.02(3) . ?
C7 C8 1.380(4) . ?
C7 H7 1.04(3) . ?
C8 C8A 1.404(3) . ?
C8 N16 1.421(4) . ?
C8A N9 1.375(3) . ?
N9 C9A 1.391(3) . ?
N9 H9 0.93(3) . ?
N10 C11 1.344(3) . ?
N10 H10 0.85(3) . ?
C11 O11 1.230(3) . ?
C11 C12 1.494(4) . ?
C12 C13B 1.499(4) . ?
C12 C13A 1.499(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13A C14A 1.516(5) . ?
C13A H13A 0.9700 . ?
C13A H13B 0.9700 . ?
C14A C15A 1.528(8) . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C13B C14B 1.52(2) . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C14B C15B 1.51(2) . ?
C14B H14C 0.9700 . ?
C14B H14D 0.9700 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
N16 C17 1.345(3) . ?
N16 H16 0.91(3) . ?
C17 O17 1.234(3) . ?
C17 C18 1.493(4) . ?
C18 C19 1.498(4) . ?
C18 H18A 0.99(4) . ?
C18 H18B 0.92(3) . ?
C19 C20 1.501(4) . ?
C19 H19A 0.98(3) . ?
C19 H19B 0.93(3) . ?
C20 C21 1.502(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9A 117.2(3) . . ?
C2 C1 N10 119.0(2) . . ?
C9A C1 N10 123.7(2) . . ?
C1 C2 C3 122.2(3) . . ?
C1 C2 H2 118.4(15) . . ?
C3 C2 H2 119.5(15) . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 116.0(16) . . ?
C2 C3 H3 122.8(16) . . ?
C3 C4 C4A 118.0(3) . . ?
C3 C4 H4 122.9(16) . . ?
C4A C4 H4 119.1(16) . . ?
C4 C4A C9A 120.2(3) . . ?
C4 C4A C4B 133.1(3) . . ?
C9A C4A C4B 106.7(2) . . ?
C5 C4B C8A 121.0(3) . . ?
C5 C4B C4A 132.5(3) . . ?
C8A C4B C4A 106.4(2) . . ?
C6 C5 C4B 117.6(3) . . ?
C6 C5 H5 118.9(16) . . ?
C4B C5 H5 123.6(16) . . ?
C5 C6 C7 121.5(3) . . ?
C5 C6 H6 115.3(16) . . ?
C7 C6 H6 123.2(16) . . ?
C8 C7 C6 122.1(3) . . ?
C8 C7 H7 116.0(16) . . ?
C6 C7 H7 121.9(16) . . ?
C7 C8 C8A 117.1(3) . . ?
C7 C8 N16 119.2(3) . . ?
C8A C8 N16 123.5(3) . . ?
N9 C8A C8 130.0(3) . . ?
N9 C8A C4B 109.2(2) . . ?
C8 C8A C4B 120.7(2) . . ?
C8A N9 C9A 108.5(2) . . ?
C8A N9 H9 124.0(17) . . ?
C9A N9 H9 127.4(17) . . ?
N9 C9A C1 129.6(3) . . ?
N9 C9A C4A 109.2(2) . . ?
C1 C9A C4A 121.2(2) . . ?
C11 N10 C1 126.9(2) . . ?
C11 N10 H10 117.3(18) . . ?
C1 N10 H10 112.7(17) . . ?
O11 C11 N10 121.5(3) . . ?
O11 C11 C12 121.8(3) . . ?
N10 C11 C12 116.7(2) . . ?
C11 C12 C13B 114.3(2) . . ?
C11 C12 C13A 114.3(2) . . ?
C11 C12 H12A 108.7 . . ?
C13A C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13A C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13A C14A 113.3(4) . . ?
C12 C13A H13A 108.9 . . ?
C14A C13A H13A 108.9 . . ?
C12 C13A H13B 108.9 . . ?
C14A C13A H13B 108.9 . . ?
H13A C13A H13B 107.7 . . ?
C13A C14A C15A 111.5(6) . . ?
C13A C14A H14A 109.3 . . ?
C15A C14A H14A 109.3 . . ?
C13A C14A H14B 109.3 . . ?
C15A C14A H14B 109.3 . . ?
H14A C14A H14B 108.0 . . ?
C14A C15A H15A 109.5 . . ?
C14A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C14A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C12 C13B C14B 131(3) . . ?
C12 C13B H13C 104.5 . . ?
C14B C13B H13C 104.5 . . ?
C12 C13B H13D 104.5 . . ?
C14B C13B H13D 104.5 . . ?
H13C C13B H13D 105.6 . . ?
C15B C14B C13B 112(2) . . ?
C15B C14B H14C 109.3 . . ?
C13B C14B H14C 109.3 . . ?
C15B C14B H14D 109.3 . . ?
C13B C14B H14D 109.3 . . ?
H14C C14B H14D 108.0 . . ?
C14B C15B H15D 109.5 . . ?
C14B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C14B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C17 N16 C8 127.4(2) . . ?
C17 N16 H16 113.5(17) . . ?
C8 N16 H16 117.5(17) . . ?
O17 C17 N16 121.3(3) . . ?
O17 C17 C18 122.0(3) . . ?
N16 C17 C18 116.6(2) . . ?
C17 C18 C19 115.5(3) . . ?
C17 C18 H18A 100.7(19) . . ?
C19 C18 H18A 113.4(19) . . ?
C17 C18 H18B 110.7(16) . . ?
C19 C18 H18B 114.5(16) . . ?
H18A C18 H18B 100(2) . . ?
C18 C19 C20 114.3(3) . . ?
C18 C19 H19A 107.6(19) . . ?
C20 C19 H19A 111.3(19) . . ?
C18 C19 H19B 107.7(19) . . ?
C20 C19 H19B 111.3(19) . . ?
H19A C19 H19B 104(3) . . ?
C19 C20 C21 114.1(3) . . ?
C19 C20 H20A 108.7 . . ?
C21 C20 H20A 108.7 . . ?
C19 C20 H20B 108.7 . . ?
C21 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A C1 C2 C3 0.2(4) . . . . ?
N10 C1 C2 C3 176.4(3) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C4A -1.1(5) . . . . ?
C3 C4 C4A C9A 1.7(4) . . . . ?
C3 C4 C4A C4B -176.3(3) . . . . ?
C4 C4A C4B C5 -4.5(6) . . . . ?
C9A C4A C4B C5 177.3(3) . . . . ?
C4 C4A C4B C8A 178.5(3) . . . . ?
C9A C4A C4B C8A 0.2(3) . . . . ?
C8A C4B C5 C6 0.0(4) . . . . ?
C4A C4B C5 C6 -176.7(3) . . . . ?
C4B C5 C6 C7 0.4(5) . . . . ?
C5 C6 C7 C8 -0.6(5) . . . . ?
C6 C7 C8 C8A 0.3(4) . . . . ?
C6 C7 C8 N16 175.6(3) . . . . ?
C7 C8 C8A N9 177.3(3) . . . . ?
N16 C8 C8A N9 2.2(4) . . . . ?
C7 C8 C8A C4B 0.2(4) . . . . ?
N16 C8 C8A C4B -174.9(2) . . . . ?
C5 C4B C8A N9 -178.0(3) . . . . ?
C4A C4B C8A N9 -0.5(3) . . . . ?
C5 C4B C8A C8 -0.4(4) . . . . ?
C4A C4B C8A C8 177.1(2) . . . . ?
C8 C8A N9 C9A -176.7(3) . . . . ?
C4B C8A N9 C9A 0.6(3) . . . . ?
C8A N9 C9A C1 -177.1(3) . . . . ?
C8A N9 C9A C4A -0.4(3) . . . . ?
C2 C1 C9A N9 176.7(3) . . . . ?
N10 C1 C9A N9 0.7(4) . . . . ?
C2 C1 C9A C4A 0.4(4) . . . . ?
N10 C1 C9A C4A -175.6(2) . . . . ?
C4 C4A C9A N9 -178.4(2) . . . . ?
C4B C4A C9A N9 0.1(3) . . . . ?
C4 C4A C9A C1 -1.4(4) . . . . ?
C4B C4A C9A C1 177.1(2) . . . . ?
C2 C1 N10 C11 135.9(3) . . . . ?
C9A C1 N10 C11 -48.2(4) . . . . ?
C1 N10 C11 O11 6.9(4) . . . . ?
C1 N10 C11 C12 -173.1(2) . . . . ?
O11 C11 C12 C13B 39.9(4) . . . . ?
N10 C11 C12 C13B -140.0(3) . . . . ?
O11 C11 C12 C13A 39.9(4) . . . . ?
N10 C11 C12 C13A -140.0(3) . . . . ?
C11 C12 C13A C14A -172.9(4) . . . . ?
C12 C13A C14A C15A 176.2(5) . . . . ?
C11 C12 C13B C14B 168.9(19) . . . . ?
C12 C13B C14B C15B 88(5) . . . . ?
C7 C8 N16 C17 139.5(3) . . . . ?
C8A C8 N16 C17 -45.5(4) . . . . ?
C8 N16 C17 O17 4.3(4) . . . . ?
C8 N16 C17 C18 -174.1(3) . . . . ?
O17 C17 C18 C19 33.5(5) . . . . ?
N16 C17 C18 C19 -148.1(3) . . . . ?
C17 C18 C19 C20 -172.6(3) . . . . ?
C18 C19 C20 C21 179.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N9 H9 O17 0.93(3) 2.23(3) 2.779(3) 117(2) .
N9 H9 O11 0.93(3) 2.34(3) 2.805(3) 111(2) .
N10 H10 O17 0.85(3) 2.17(3) 2.969(3) 159(2) 2_565
N16 H16 O11 0.91(3) 2.02(3) 2.916(3) 167(2) 2_575

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.070


_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_karb_7c
_database_code_depnum_ccdc_archive 'CCDC 1826924'
_audit_update_record             
;
2018-06-19 deposited with the CCDC.
2018-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H19 N3 O2'
_chemical_formula_weight         405.44

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

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

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

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

_cell_length_a                   9.955(2)
_cell_length_b                   15.804(3)
_cell_length_c                   13.546(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.143(16)
_cell_angle_gamma                90
_cell_volume                     2025.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5000
_cell_measurement_theta_min      4
_cell_measurement_theta_max      20

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.950
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
;
CrysAlis RED
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  KM4CCD
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 8.6479
_diffrn_reflns_number            14925
_diffrn_reflns_av_unetI/netI     0.1254
_diffrn_reflns_av_R_equivalents  0.1288
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.025
_diffrn_reflns_theta_max         25.198
_diffrn_reflns_theta_full        25.198
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3645
_reflns_number_gt                1520
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       CrysAlisCCD
_computing_cell_refinement       CrysAlisRED
_computing_data_reduction        CrysAlisRED
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  'XCIF (Bruker AXS Inc., 2013)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1067P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3645
_refine_ls_number_parameters     357
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1626
_refine_ls_R_factor_gt           0.0694
_refine_ls_wR_factor_ref         0.2267
_refine_ls_wR_factor_gt          0.1651
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_restrained_S_all      0.915
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0570(4) 0.8582(3) 0.4855(3) 0.0439(11) Uani 1 1 d . . . . .
C2 C -0.0270(5) 0.7869(3) 0.4606(4) 0.0520(12) Uani 1 1 d . . . . .
C3 C -0.0521(5) 0.7433(3) 0.3669(4) 0.0577(13) Uani 1 1 d . . . . .
C4 C 0.0116(5) 0.7705(3) 0.2949(4) 0.0529(12) Uani 1 1 d D . . . .
C4A C 0.1006(4) 0.8404(3) 0.3186(3) 0.0473(11) Uani 1 1 d . . . . .
C4B C 0.1852(4) 0.8847(3) 0.2638(3) 0.0486(11) Uani 1 1 d . . . . .
C5 C 0.2136(5) 0.8709(3) 0.1700(3) 0.0571(13) Uani 1 1 d . . . . .
C6 C 0.3035(5) 0.9260(3) 0.1432(4) 0.0628(14) Uani 1 1 d D . . . .
C7 C 0.3642(5) 0.9957(3) 0.2070(4) 0.0593(13) Uani 1 1 d . . . . .
C8 C 0.3384(4) 1.0106(3) 0.2994(3) 0.0479(11) Uani 1 1 d . . . . .
C8A C 0.2488(4) 0.9547(3) 0.3271(3) 0.0465(11) Uani 1 1 d . . . . .
C9A C 0.1220(4) 0.8845(3) 0.4144(3) 0.0443(10) Uani 1 1 d . . . . .
N9 N 0.2079(4) 0.9546(2) 0.4163(3) 0.0465(9) Uani 1 1 d D . . . .
N10 N 0.0678(4) 0.9034(2) 0.5785(3) 0.0470(10) Uani 1 1 d . . . . .
C11 C 0.1837(5) 0.9412(3) 0.6426(3) 0.0470(11) Uani 1 1 d . . . . .
O11 O 0.2988(3) 0.9403(2) 0.6243(2) 0.0664(10) Uani 1 1 d . . . . .
C12 C 0.1727(4) 0.9842(3) 0.7370(3) 0.0456(11) Uani 1 1 d . . . . .
C13 C 0.0782(5) 0.9601(3) 0.7867(3) 0.0520(12) Uani 1 1 d . . . . .
C14 C 0.0795(6) 0.9985(4) 0.8789(4) 0.0717(15) Uani 1 1 d . . . . .
C15 C 0.1764(7) 1.0614(4) 0.9224(4) 0.0773(17) Uani 1 1 d . . . . .
C16 C 0.2700(7) 1.0869(4) 0.8723(4) 0.0793(17) Uani 1 1 d . . . . .
C17 C 0.2693(6) 1.0473(3) 0.7799(4) 0.0661(14) Uani 1 1 d . . . . .
N18 N 0.4086(4) 1.0772(2) 0.3659(3) 0.0481(10) Uani 1 1 d . . . . .
C19 C 0.3439(5) 1.1311(3) 0.4128(3) 0.0468(11) Uani 1 1 d . . . . .
O19 O 0.2141(3) 1.13125(19) 0.3955(2) 0.0610(9) Uani 1 1 d . . . . .
C20 C 0.4368(4) 1.1904(3) 0.4912(3) 0.0481(11) Uani 1 1 d . . . . .
C21 C 0.5585(5) 1.2261(3) 0.4805(4) 0.0555(13) Uani 1 1 d . . . . .
C22 C 0.6367(6) 1.2832(3) 0.5551(5) 0.0667(14) Uani 1 1 d . . . . .
C23 C 0.5943(6) 1.3025(4) 0.6381(5) 0.0810(18) Uani 1 1 d . . . . .
C24 C 0.4741(6) 1.2684(4) 0.6496(5) 0.0871(19) Uani 1 1 d . . . . .
C25 C 0.3946(6) 1.2111(4) 0.5759(4) 0.0696(15) Uani 1 1 d . . . . .
H2 H -0.073(4) 0.764(2) 0.513(3) 0.045(11) Uiso 1 1 d . . . . .
H3 H -0.117(5) 0.687(3) 0.352(4) 0.100(18) Uiso 1 1 d . . . . .
H4 H -0.005(5) 0.730(3) 0.226(3) 0.097(17) Uiso 1 1 d D . . . .
H5 H 0.170(4) 0.815(3) 0.119(3) 0.070(13) Uiso 1 1 d . . . . .
H6 H 0.320(5) 0.926(3) 0.066(2) 0.109(18) Uiso 1 1 d D . . . .
H7 H 0.436(4) 1.040(2) 0.183(3) 0.051(11) Uiso 1 1 d . . . . .
H9 H 0.258(5) 0.988(3) 0.481(3) 0.12(2) Uiso 1 1 d D . . . .
H10 H -0.002(5) 0.901(3) 0.601(3) 0.054(14) Uiso 1 1 d . . . . .
H13 H 0.008(4) 0.913(2) 0.753(3) 0.036(10) Uiso 1 1 d . . . . .
H14 H 0.004(5) 0.976(3) 0.917(4) 0.095(17) Uiso 1 1 d . . . . .
H15 H 0.173(5) 1.090(3) 0.996(4) 0.077(14) Uiso 1 1 d . . . . .
H16 H 0.350(7) 1.136(4) 0.899(5) 0.13(2) Uiso 1 1 d . . . . .
H17 H 0.343(6) 1.051(3) 0.744(4) 0.095(18) Uiso 1 1 d . . . . .
H18 H 0.513(6) 1.084(3) 0.376(4) 0.104(19) Uiso 1 1 d . . . . .
H21 H 0.585(4) 1.209(2) 0.422(3) 0.043(12) Uiso 1 1 d . . . . .
H22 H 0.730(5) 1.313(3) 0.547(4) 0.083(15) Uiso 1 1 d . . . . .
H23 H 0.639(7) 1.352(4) 0.691(5) 0.14(2) Uiso 1 1 d . . . . .
H24 H 0.429(6) 1.285(4) 0.714(5) 0.12(2) Uiso 1 1 d . . . . .
H25 H 0.316(5) 1.186(3) 0.574(4) 0.073(17) 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 C9A 1.380(5) . ?
C1 C2 1.381(6) . ?
C1 N10 1.423(5) . ?
C2 C3 1.397(6) . ?
C2 H2 1.02(4) . ?
C3 C4 1.387(6) . ?
C3 H3 1.08(5) . ?
C4 C4A 1.391(6) . ?
C4 H4 1.11(2) . ?
C4A C9A 1.430(6) . ?
C4A C4B 1.462(6) . ?
C4B C5 1.402(6) . ?
C4B C8A 1.421(6) . ?
C5 C6 1.377(6) . ?
C5 H5 1.13(4) . ?
C6 C7 1.413(6) . ?
C6 H6 1.11(2) . ?
C7 C8 1.374(6) . ?
C7 H7 1.12(4) . ?
C8 C8A 1.388(6) . ?
C8 N18 1.420(5) . ?
C8A N9 1.390(5) . ?
C9A N9 1.395(5) . ?
N9 H9 1.01(2) . ?
N10 C11 1.347(5) . ?
N10 H10 0.84(4) . ?
C11 O11 1.245(5) . ?
C11 C12 1.482(6) . ?
C12 C13 1.371(6) . ?
C12 C17 1.382(6) . ?
C13 C14 1.385(6) . ?
C13 H13 1.03(4) . ?
C14 C15 1.382(7) . ?
C14 H14 1.09(5) . ?
C15 C16 1.373(8) . ?
C15 H15 1.10(5) . ?
C16 C17 1.398(7) . ?
C16 H16 1.09(7) . ?
C17 H17 1.01(5) . ?
N18 C19 1.342(5) . ?
N18 H18 1.01(6) . ?
C19 O19 1.239(5) . ?
C19 C20 1.499(6) . ?
C20 C25 1.378(6) . ?
C20 C21 1.385(6) . ?
C21 C22 1.397(7) . ?
C21 H21 0.95(4) . ?
C22 C23 1.353(8) . ?
C22 H22 1.08(5) . ?
C23 C24 1.365(8) . ?
C23 H23 1.07(7) . ?
C24 C25 1.397(7) . ?
C24 H24 1.13(6) . ?
C25 H25 0.87(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9A C1 C2 117.1(4) . . ?
C9A C1 N10 122.9(4) . . ?
C2 C1 N10 119.9(4) . . ?
C1 C2 C3 123.2(4) . . ?
C1 C2 H2 119(2) . . ?
C3 C2 H2 118(2) . . ?
C4 C3 C2 119.7(5) . . ?
C4 C3 H3 120(3) . . ?
C2 C3 H3 120(3) . . ?
C3 C4 C4A 118.8(4) . . ?
C3 C4 H4 116(3) . . ?
C4A C4 H4 125(3) . . ?
C4 C4A C9A 120.1(4) . . ?
C4 C4A C4B 133.6(4) . . ?
C9A C4A C4B 106.3(4) . . ?
C5 C4B C8A 119.3(4) . . ?
C5 C4B C4A 134.1(4) . . ?
C8A C4B C4A 106.6(4) . . ?
C6 C5 C4B 118.1(4) . . ?
C6 C5 H5 120(2) . . ?
C4B C5 H5 122(2) . . ?
C5 C6 C7 121.4(4) . . ?
C5 C6 H6 123(3) . . ?
C7 C6 H6 114(3) . . ?
C8 C7 C6 121.7(4) . . ?
C8 C7 H7 118.4(19) . . ?
C6 C7 H7 119.9(19) . . ?
C7 C8 C8A 117.1(4) . . ?
C7 C8 N18 120.7(4) . . ?
C8A C8 N18 122.1(4) . . ?
C8 C8A N9 128.5(4) . . ?
C8 C8A C4B 122.4(4) . . ?
N9 C8A C4B 109.1(4) . . ?
C1 C9A N9 130.1(4) . . ?
C1 C9A C4A 121.1(4) . . ?
N9 C9A C4A 108.6(4) . . ?
C8A N9 C9A 109.2(3) . . ?
C8A N9 H9 124(3) . . ?
C9A N9 H9 124(3) . . ?
C11 N10 C1 127.3(4) . . ?
C11 N10 H10 115(3) . . ?
C1 N10 H10 117(3) . . ?
O11 C11 N10 121.5(4) . . ?
O11 C11 C12 119.7(4) . . ?
N10 C11 C12 118.8(4) . . ?
C13 C12 C17 119.2(4) . . ?
C13 C12 C11 122.9(4) . . ?
C17 C12 C11 117.8(4) . . ?
C12 C13 C14 120.4(5) . . ?
C12 C13 H13 117.3(19) . . ?
C14 C13 H13 122.3(19) . . ?
C15 C14 C13 120.7(5) . . ?
C15 C14 H14 122(3) . . ?
C13 C14 H14 118(3) . . ?
C16 C15 C14 119.4(5) . . ?
C16 C15 H15 123(2) . . ?
C14 C15 H15 118(2) . . ?
C15 C16 C17 119.8(6) . . ?
C15 C16 H16 126(3) . . ?
C17 C16 H16 115(3) . . ?
C12 C17 C16 120.6(5) . . ?
C12 C17 H17 111(3) . . ?
C16 C17 H17 128(3) . . ?
C19 N18 C8 123.9(4) . . ?
C19 N18 H18 119(3) . . ?
C8 N18 H18 117(3) . . ?
O19 C19 N18 122.5(4) . . ?
O19 C19 C20 120.7(4) . . ?
N18 C19 C20 116.8(4) . . ?
C25 C20 C21 119.5(5) . . ?
C25 C20 C19 117.2(4) . . ?
C21 C20 C19 123.2(4) . . ?
C20 C21 C22 119.8(5) . . ?
C20 C21 H21 117(2) . . ?
C22 C21 H21 123(2) . . ?
C23 C22 C21 120.0(5) . . ?
C23 C22 H22 120(3) . . ?
C21 C22 H22 120(3) . . ?
C22 C23 C24 121.1(6) . . ?
C22 C23 H23 124(3) . . ?
C24 C23 H23 114(3) . . ?
C23 C24 C25 119.7(6) . . ?
C23 C24 H24 125(3) . . ?
C25 C24 H24 116(3) . . ?
C20 C25 C24 119.9(5) . . ?
C20 C25 H25 112(3) . . ?
C24 C25 H25 128(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A C1 C2 C3 -2.3(6) . . . . ?
N10 C1 C2 C3 174.6(4) . . . . ?
C1 C2 C3 C4 1.4(7) . . . . ?
C2 C3 C4 C4A 0.7(7) . . . . ?
C3 C4 C4A C9A -1.7(6) . . . . ?
C3 C4 C4A C4B 178.8(4) . . . . ?
C4 C4A C4B C5 -3.8(8) . . . . ?
C9A C4A C4B C5 176.7(5) . . . . ?
C4 C4A C4B C8A 177.4(5) . . . . ?
C9A C4A C4B C8A -2.1(4) . . . . ?
C8A C4B C5 C6 0.3(6) . . . . ?
C4A C4B C5 C6 -178.4(5) . . . . ?
C4B C5 C6 C7 -1.0(7) . . . . ?
C5 C6 C7 C8 1.2(7) . . . . ?
C6 C7 C8 C8A -0.7(7) . . . . ?
C6 C7 C8 N18 175.3(4) . . . . ?
C7 C8 C8A N9 178.7(4) . . . . ?
N18 C8 C8A N9 2.8(7) . . . . ?
C7 C8 C8A C4B 0.0(6) . . . . ?
N18 C8 C8A C4B -176.0(4) . . . . ?
C5 C4B C8A C8 0.2(6) . . . . ?
C4A C4B C8A C8 179.3(4) . . . . ?
C5 C4B C8A N9 -178.8(4) . . . . ?
C4A C4B C8A N9 0.3(5) . . . . ?
C2 C1 C9A N9 177.7(4) . . . . ?
N10 C1 C9A N9 0.9(7) . . . . ?
C2 C1 C9A C4A 1.1(6) . . . . ?
N10 C1 C9A C4A -175.6(4) . . . . ?
C4 C4A C9A C1 0.9(6) . . . . ?
C4B C4A C9A C1 -179.5(4) . . . . ?
C4 C4A C9A N9 -176.4(4) . . . . ?
C4B C4A C9A N9 3.2(4) . . . . ?
C8 C8A N9 C9A -177.1(4) . . . . ?
C4B C8A N9 C9A 1.8(4) . . . . ?
C1 C9A N9 C8A 180.0(4) . . . . ?
C4A C9A N9 C8A -3.1(4) . . . . ?
C9A C1 N10 C11 -40.7(6) . . . . ?
C2 C1 N10 C11 142.6(4) . . . . ?
C1 N10 C11 O11 0.7(7) . . . . ?
C1 N10 C11 C12 -179.1(4) . . . . ?
O11 C11 C12 C13 -151.4(4) . . . . ?
N10 C11 C12 C13 28.4(6) . . . . ?
O11 C11 C12 C17 23.9(6) . . . . ?
N10 C11 C12 C17 -156.3(4) . . . . ?
C17 C12 C13 C14 0.0(7) . . . . ?
C11 C12 C13 C14 175.3(4) . . . . ?
C12 C13 C14 C15 -0.3(8) . . . . ?
C13 C14 C15 C16 1.3(8) . . . . ?
C14 C15 C16 C17 -2.0(9) . . . . ?
C13 C12 C17 C16 -0.7(7) . . . . ?
C11 C12 C17 C16 -176.2(5) . . . . ?
C15 C16 C17 C12 1.7(8) . . . . ?
C7 C8 N18 C19 135.5(4) . . . . ?
C8A C8 N18 C19 -48.8(6) . . . . ?
C8 N18 C19 O19 -5.7(6) . . . . ?
C8 N18 C19 C20 172.2(4) . . . . ?
O19 C19 C20 C25 32.4(6) . . . . ?
N18 C19 C20 C25 -145.6(4) . . . . ?
O19 C19 C20 C21 -145.8(4) . . . . ?
N18 C19 C20 C21 36.3(6) . . . . ?
C25 C20 C21 C22 -0.5(7) . . . . ?
C19 C20 C21 C22 177.6(4) . . . . ?
C20 C21 C22 C23 0.9(7) . . . . ?
C21 C22 C23 C24 -1.3(9) . . . . ?
C22 C23 C24 C25 1.4(10) . . . . ?
C21 C20 C25 C24 0.5(8) . . . . ?
C19 C20 C25 C24 -177.7(5) . . . . ?
C23 C24 C25 C20 -0.9(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N9 H9 O11 1.01(2) 2.00(5) 2.687(5) 123(4) .
N9 H9 O19 1.01(2) 2.52(6) 2.809(5) 96(3) .
N10 H10 O19 0.84(4) 2.18(4) 2.986(5) 158(4) 3_576
N18 H18 O11 1.01(6) 1.91(6) 2.887(5) 160(5) 3_676

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.066


_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_karb_7c_benz
_database_code_depnum_ccdc_archive 'CCDC 1826925'
_audit_update_record             
;
2018-06-19 deposited with the CCDC.
2018-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C49 H60 N4 O4'
_chemical_formula_weight         769.01

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6576(5)
_cell_length_b                   15.7440(9)
_cell_length_c                   16.1197(9)
_cell_angle_alpha                89.599(4)
_cell_angle_beta                 78.285(5)
_cell_angle_gamma                84.114(5)
_cell_volume                     2139.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8000
_cell_measurement_theta_min      3
_cell_measurement_theta_max      23

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_F_000             828
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.910
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   
;
CrysAlis RED
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  KM4DDC
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32633
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.706
_diffrn_reflns_theta_max         25.197
_diffrn_reflns_theta_full        25.197
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7697
_reflns_number_gt                5903
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       CrysAlisCCD
_computing_cell_refinement       CrysALisRED
_computing_data_reduction        CrysALisRED
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  'XCIF (Bruker AXS Inc., 2013)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1106P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7697
_refine_ls_number_parameters     733
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1570
_refine_ls_wR_factor_gt          0.1309
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.50710(18) 0.67153(11) 0.39836(10) 0.0208(4) Uani 1 1 d . . . . .
C2 C 0.51845(19) 0.64911(12) 0.48080(11) 0.0244(4) Uani 1 1 d . . . . .
C3 C 0.4962(2) 0.71087(12) 0.54550(11) 0.0262(4) Uani 1 1 d . . . . .
C4 C 0.4587(2) 0.79623(12) 0.53060(11) 0.0249(4) Uani 1 1 d . . . . .
C4A C 0.44692(18) 0.82017(11) 0.44840(10) 0.0210(4) Uani 1 1 d . . . . .
C4B C 0.40264(18) 0.90070(11) 0.41118(10) 0.0211(4) Uani 1 1 d . . . . .
C5 C 0.3512(2) 0.98320(12) 0.44446(12) 0.0264(4) Uani 1 1 d . . . . .
C6 C 0.3136(2) 1.04659(12) 0.38969(12) 0.0288(4) Uani 1 1 d . . . . .
C7 C 0.3259(2) 1.02994(12) 0.30325(11) 0.0263(4) Uani 1 1 d . . . . .
C8 C 0.37475(19) 0.94844(11) 0.26870(10) 0.0216(4) Uani 1 1 d . . . . .
C8A C 0.41342(18) 0.88386(11) 0.32410(10) 0.0196(4) Uani 1 1 d . . . . .
C9A C 0.47685(18) 0.75829(11) 0.38236(10) 0.0197(4) Uani 1 1 d . . . . .
N9 N 0.45697(16) 0.79733(9) 0.30658(9) 0.0190(3) Uani 1 1 d . . . . .
N10 N 0.52175(16) 0.60978(9) 0.33234(9) 0.0214(3) Uani 1 1 d . . . . .
C11 C 0.44534(19) 0.53729(11) 0.34450(11) 0.0217(4) Uani 1 1 d . . . . .
O11 O 0.35709(14) 0.52287(8) 0.41197(8) 0.0297(3) Uani 1 1 d . . . . .
C12 C 0.47070(19) 0.47550(11) 0.27140(11) 0.0222(4) Uani 1 1 d . . . . .
C13 C 0.3679(2) 0.41144(12) 0.27797(12) 0.0270(4) Uani 1 1 d . . . . .
C14 C 0.3825(2) 0.35193(12) 0.21314(13) 0.0330(5) Uani 1 1 d . . . . .
C15 C 0.5010(2) 0.35445(13) 0.14129(13) 0.0331(4) Uani 1 1 d . . . . .
C16 C 0.6051(2) 0.41685(12) 0.13488(12) 0.0320(4) Uani 1 1 d . . . . .
C17 C 0.5898(2) 0.47747(12) 0.19890(11) 0.0272(4) Uani 1 1 d . . . . .
N18 N 0.38770(18) 0.92755(10) 0.18193(9) 0.0231(3) Uani 1 1 d . . . . .
C19 C 0.2864(2) 0.96185(12) 0.13260(11) 0.0255(4) Uani 1 1 d . . . . .
O19 O 0.17119(15) 1.01355(10) 0.16014(8) 0.0389(4) Uani 1 1 d . . . . .
C20 C 0.3215(2) 0.93220(11) 0.04201(11) 0.0257(4) Uani 1 1 d . . . . .
C21 C 0.1970(3) 0.94317(14) -0.00124(13) 0.0372(5) Uani 1 1 d . . . . .
C22 C 0.2213(3) 0.91999(15) -0.08617(13) 0.0445(6) Uani 1 1 d . . . . .
C23 C 0.3691(3) 0.88491(14) -0.12818(13) 0.0400(5) Uani 1 1 d . . . . .
C24 C 0.4936(3) 0.87309(12) -0.08540(12) 0.0319(5) Uani 1 1 d . . . . .
C25 C 0.4697(2) 0.89658(11) -0.00048(11) 0.0269(4) Uani 1 1 d . . . . .
H2 H 0.538(2) 0.5904(13) 0.4911(11) 0.026(5) Uiso 1 1 d . . . . .
H3 H 0.506(2) 0.6939(13) 0.6018(13) 0.035(5) Uiso 1 1 d . . . . .
H4 H 0.439(2) 0.8396(12) 0.5771(12) 0.025(5) Uiso 1 1 d . . . . .
H5 H 0.339(2) 0.9965(13) 0.5073(13) 0.037(5) Uiso 1 1 d . . . . .
H6 H 0.277(2) 1.1071(14) 0.4110(13) 0.042(6) Uiso 1 1 d . . . . .
H7 H 0.294(2) 1.0774(13) 0.2679(12) 0.032(5) Uiso 1 1 d . . . . .
H9 H 0.511(3) 0.7748(13) 0.2531(14) 0.040(6) Uiso 1 1 d . . . . .
H10 H 0.572(2) 0.6249(13) 0.2794(14) 0.033(5) Uiso 1 1 d . . . . .
H13 H 0.285(2) 0.4084(12) 0.3295(12) 0.029(5) Uiso 1 1 d . . . . .
H14 H 0.308(3) 0.3086(14) 0.2201(13) 0.041(6) Uiso 1 1 d . . . . .
H15 H 0.514(2) 0.3121(13) 0.0924(13) 0.037(5) Uiso 1 1 d . . . . .
H16 H 0.683(2) 0.4207(13) 0.0828(13) 0.036(5) Uiso 1 1 d . . . . .
H17 H 0.665(2) 0.5256(12) 0.1909(12) 0.030(5) Uiso 1 1 d . . . . .
H18 H 0.462(3) 0.8849(14) 0.1598(13) 0.037(6) Uiso 1 1 d . . . . .
H21 H 0.089(3) 0.9683(14) 0.0279(14) 0.041(6) Uiso 1 1 d . . . . .
H22 H 0.130(3) 0.9291(15) -0.1154(15) 0.051(6) Uiso 1 1 d . . . . .
H23 H 0.390(3) 0.8701(14) -0.1893(15) 0.046(6) Uiso 1 1 d . . . . .
H24 H 0.598(3) 0.8528(13) -0.1175(13) 0.038(6) Uiso 1 1 d . . . . .
H25 H 0.557(2) 0.8872(12) 0.0291(12) 0.028(5) Uiso 1 1 d . . . . .
O1BE O 0.69620(17) 0.66257(9) 0.17374(8) 0.0382(4) Uani 1 1 d . . . . .
O2BE O 0.6429(2) 0.79709(11) 0.14018(9) 0.0557(5) Uani 1 1 d . . . . .
C1BE C 0.80377(19) 0.70525(11) 0.03420(11) 0.0235(4) Uani 1 1 d . . . . .
C2BE C 0.8531(2) 0.77188(13) -0.01847(12) 0.0307(4) Uani 1 1 d . . . . .
C3BE C 0.9448(2) 0.75496(14) -0.09944(12) 0.0366(5) Uani 1 1 d . . . . .
C4BE C 0.9872(2) 0.67169(14) -0.12785(13) 0.0381(5) Uani 1 1 d . . . . .
C5BE C 0.9390(3) 0.60479(14) -0.07589(13) 0.0423(5) Uani 1 1 d . . . . .
C6BE C 0.8481(2) 0.62140(13) 0.00492(12) 0.0341(5) Uani 1 1 d . . . . .
C7BE C 0.7056(2) 0.72288(12) 0.12229(11) 0.0270(4) Uani 1 1 d . . . . .
H2BE H 0.831(2) 0.8353(14) 0.0020(13) 0.040(6) Uiso 1 1 d . . . . .
H3BE H 0.984(3) 0.8064(16) -0.1374(16) 0.061(7) Uiso 1 1 d . . . . .
H4BE H 1.052(3) 0.6595(15) -0.1876(15) 0.053(7) Uiso 1 1 d . . . . .
H5BE H 0.966(3) 0.5405(17) -0.0970(16) 0.064(7) Uiso 1 1 d . . . . .
H6BE H 0.807(3) 0.5719(15) 0.0424(14) 0.047(6) Uiso 1 1 d . . . . .
N26 N 0.00551(16) 0.73592(9) 0.31444(9) 0.0208(3) Uani 1 1 d . . . . .
C27 C 0.0757(2) 0.74251(12) 0.39327(11) 0.0223(4) Uani 1 1 d . . . . .
C28 C -0.0387(2) 0.73822(12) 0.47795(11) 0.0243(4) Uani 1 1 d . . . . .
C29 C 0.0409(3) 0.76398(14) 0.54842(12) 0.0318(5) Uani 1 1 d . . . . .
C30 C -0.0548(3) 0.74966(12) 0.63664(12) 0.0348(5) Uani 1 1 d . . . . .
H30A H -0.160454 0.780990 0.643087 0.052 Uiso 1 1 calc R U . . .
H30B H -0.000560 0.770218 0.679180 0.052 Uiso 1 1 calc R U . . .
H30C H -0.065025 0.688564 0.644478 0.052 Uiso 1 1 calc R U . . .
C31 C -0.12128(19) 0.81001(11) 0.31100(11) 0.0218(4) Uani 1 1 d . . . . .
C32 C -0.0715(2) 0.89867(11) 0.32040(13) 0.0262(4) Uani 1 1 d . . . . .
C33 C -0.1966(2) 0.96709(11) 0.30118(12) 0.0260(4) Uani 1 1 d . . . . .
C34 C -0.1522(2) 1.05678(12) 0.31327(13) 0.0300(4) Uani 1 1 d . . . . .
C35 C 0.1424(2) 0.73695(12) 0.23848(11) 0.0227(4) Uani 1 1 d . . . . .
C36 C 0.1010(2) 0.72758(13) 0.15200(11) 0.0263(4) Uani 1 1 d . . . . .
C37 C 0.2525(2) 0.70714(12) 0.08387(12) 0.0282(4) Uani 1 1 d . . . . .
C38 C 0.3371(2) 0.61879(13) 0.09102(12) 0.0364(5) Uani 1 1 d . . . . .
H38A H 0.369182 0.613909 0.145895 0.055 Uiso 1 1 calc R U . . .
H38B H 0.431199 0.609911 0.045332 0.055 Uiso 1 1 calc R U . . .
H38C H 0.265356 0.575550 0.086426 0.055 Uiso 1 1 calc R U . . .
C39 C -0.0748(2) 0.65400(11) 0.31507(11) 0.0218(4) Uani 1 1 d . . . . .
C40 C 0.0360(2) 0.57187(12) 0.30690(13) 0.0267(4) Uani 1 1 d . . . . .
C41 C -0.0578(2) 0.49445(12) 0.31236(13) 0.0303(4) Uani 1 1 d . . . . .
C42 C -0.1397(4) 0.47499(16) 0.40078(19) 0.0582(8) Uani 1 1 d . . . . .
H27A H 0.159(2) 0.6966(12) 0.3882(12) 0.026(5) Uiso 1 1 d . . . . .
H27B H 0.123(2) 0.7955(13) 0.3905(12) 0.028(5) Uiso 1 1 d . . . . .
H28A H -0.072(2) 0.6825(13) 0.4883(12) 0.030(5) Uiso 1 1 d . . . . .
H28B H -0.141(2) 0.7773(12) 0.4776(12) 0.028(5) Uiso 1 1 d . . . . .
H29A H 0.140(3) 0.7351(13) 0.5413(13) 0.034(6) Uiso 1 1 d . . . . .
H29B H 0.053(2) 0.8251(15) 0.5434(13) 0.042(6) Uiso 1 1 d . . . . .
H31A H -0.212(2) 0.7979(11) 0.3566(12) 0.023(5) Uiso 1 1 d . . . . .
H31B H -0.153(2) 0.8014(11) 0.2583(12) 0.021(4) Uiso 1 1 d . . . . .
H32A H -0.055(2) 0.9081(13) 0.3783(14) 0.034(5) Uiso 1 1 d . . . . .
H32B H 0.024(3) 0.9082(13) 0.2823(13) 0.037(6) Uiso 1 1 d . . . . .
H33A H -0.296(3) 0.9605(12) 0.3397(13) 0.033(5) Uiso 1 1 d . . . . .
H33B H -0.209(2) 0.9584(12) 0.2409(13) 0.027(5) Uiso 1 1 d . . . . .
H34A H -0.141(3) 1.0684(14) 0.3711(15) 0.043(6) Uiso 1 1 d . . . . .
H34B H -0.045(3) 1.0675(14) 0.2750(15) 0.050(6) Uiso 1 1 d . . . . .
H34C H -0.230(3) 1.1017(15) 0.2992(14) 0.045(6) Uiso 1 1 d . . . . .
H35A H 0.190(2) 0.7874(12) 0.2434(11) 0.025(5) Uiso 1 1 d . . . . .
H35B H 0.222(2) 0.6871(11) 0.2495(11) 0.021(4) Uiso 1 1 d . . . . .
H36A H 0.040(2) 0.7821(13) 0.1351(12) 0.033(5) Uiso 1 1 d . . . . .
H36B H 0.032(2) 0.6768(13) 0.1510(12) 0.030(5) Uiso 1 1 d . . . . .
H37A H 0.331(2) 0.7498(13) 0.0881(12) 0.030(5) Uiso 1 1 d . . . . .
H37B H 0.227(2) 0.7131(13) 0.0295(14) 0.033(5) Uiso 1 1 d . . . . .
H39A H -0.139(2) 0.6574(12) 0.2686(12) 0.027(5) Uiso 1 1 d . . . . .
H39B H -0.154(2) 0.6546(11) 0.3683(12) 0.024(5) Uiso 1 1 d . . . . .
H40A H 0.110(3) 0.5691(13) 0.2536(14) 0.038(6) Uiso 1 1 d . . . . .
H40B H 0.098(2) 0.5691(12) 0.3509(13) 0.033(5) Uiso 1 1 d . . . . .
H41A H 0.019(2) 0.4442(13) 0.2874(12) 0.034(5) Uiso 1 1 d . . . . .
H41B H -0.139(3) 0.5079(14) 0.2746(14) 0.043(6) Uiso 1 1 d . . . . .
H42A H -0.186(4) 0.427(2) 0.4017(19) 0.079(9) Uiso 1 1 d . . . . .
H42B H -0.212(3) 0.5304(18) 0.4296(17) 0.074(8) Uiso 1 1 d . . . . .
H42C H -0.058(3) 0.4653(18) 0.4347(17) 0.065(9) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.393(2) . ?
C1 C9A 1.396(2) . ?
C1 N10 1.424(2) . ?
C2 C3 1.402(3) . ?
C2 H2 0.94(2) . ?
C3 C4 1.381(3) . ?
C3 H3 0.96(2) . ?
C4 C4A 1.396(2) . ?
C4 H4 0.993(19) . ?
C4A C9A 1.414(2) . ?
C4A C4B 1.448(2) . ?
C4B C5 1.403(2) . ?
C4B C8A 1.413(2) . ?
C5 C6 1.385(3) . ?
C5 H5 1.02(2) . ?
C6 C7 1.400(3) . ?
C6 H6 1.01(2) . ?
C7 C8 1.392(2) . ?
C7 H7 0.99(2) . ?
C8 C8A 1.408(2) . ?
C8 N18 1.419(2) . ?
C8A N9 1.391(2) . ?
C9A N9 1.397(2) . ?
N9 H9 0.95(2) . ?
N10 C11 1.370(2) . ?
N10 H10 0.92(2) . ?
C11 O11 1.230(2) . ?
C11 C12 1.500(2) . ?
C12 C17 1.395(2) . ?
C12 C13 1.402(2) . ?
C13 C14 1.386(3) . ?
C13 H13 0.99(2) . ?
C14 C15 1.386(3) . ?
C14 H14 0.98(2) . ?
C15 C16 1.389(3) . ?
C15 H15 1.02(2) . ?
C16 C17 1.388(3) . ?
C16 H16 0.97(2) . ?
C17 H17 1.04(2) . ?
N18 C19 1.369(2) . ?
N18 H18 0.90(2) . ?
C19 O19 1.230(2) . ?
C19 C20 1.498(2) . ?
C20 C25 1.390(3) . ?
C20 C21 1.394(3) . ?
C21 C22 1.388(3) . ?
C21 H21 1.00(2) . ?
C22 C23 1.382(3) . ?
C22 H22 1.00(2) . ?
C23 C24 1.390(3) . ?
C23 H23 0.99(2) . ?
C24 C25 1.389(3) . ?
C24 H24 0.97(2) . ?
C25 H25 0.97(2) . ?
O1BE C7BE 1.254(2) . ?
O2BE C7BE 1.246(2) . ?
C1BE C2BE 1.392(3) . ?
C1BE C6BE 1.394(3) . ?
C1BE C7BE 1.511(2) . ?
C2BE C3BE 1.395(3) . ?
C2BE H2BE 1.04(2) . ?
C3BE C4BE 1.380(3) . ?
C3BE H3BE 1.05(3) . ?
C4BE C5BE 1.386(3) . ?
C4BE H4BE 1.02(2) . ?
C5BE C6BE 1.390(3) . ?
C5BE H5BE 1.06(3) . ?
C6BE H6BE 1.03(2) . ?
N26 C35 1.523(2) . ?
N26 C27 1.524(2) . ?
N26 C39 1.526(2) . ?
N26 C31 1.526(2) . ?
C27 C28 1.520(2) . ?
C27 H27A 0.96(2) . ?
C27 H27B 0.96(2) . ?
C28 C29 1.520(3) . ?
C28 H28A 0.96(2) . ?
C28 H28B 1.03(2) . ?
C29 C30 1.522(3) . ?
C29 H29A 0.92(2) . ?
C29 H29B 0.98(2) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.520(2) . ?
C31 H31A 0.993(19) . ?
C31 H31B 0.959(19) . ?
C32 C33 1.524(3) . ?
C32 H32A 0.99(2) . ?
C32 H32B 0.95(2) . ?
C33 C34 1.525(3) . ?
C33 H33A 0.97(2) . ?
C33 H33B 1.01(2) . ?
C34 H34A 0.98(2) . ?
C34 H34B 1.03(2) . ?
C34 H34C 0.98(2) . ?
C35 C36 1.520(2) . ?
C35 H35A 0.94(2) . ?
C35 H35B 1.028(19) . ?
C36 C37 1.537(2) . ?
C36 H36A 1.02(2) . ?
C36 H36B 1.05(2) . ?
C37 C38 1.519(3) . ?
C37 H37A 1.01(2) . ?
C37 H37B 0.95(2) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.519(2) . ?
C39 H39A 1.02(2) . ?
C39 H39B 0.981(19) . ?
C40 C41 1.525(3) . ?
C40 H40A 0.96(2) . ?
C40 H40B 0.97(2) . ?
C41 C42 1.502(3) . ?
C41 H41A 1.01(2) . ?
C41 H41B 1.02(2) . ?
C42 H42A 0.88(3) . ?
C42 H42B 1.07(3) . ?
C42 H42C 0.97(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9A 117.24(16) . . ?
C2 C1 N10 122.52(16) . . ?
C9A C1 N10 120.23(15) . . ?
C1 C2 C3 121.35(17) . . ?
C1 C2 H2 116.6(11) . . ?
C3 C2 H2 122.0(11) . . ?
C4 C3 C2 121.42(17) . . ?
C4 C3 H3 118.8(12) . . ?
C2 C3 H3 119.8(12) . . ?
C3 C4 C4A 118.19(17) . . ?
C3 C4 H4 121.3(11) . . ?
C4A C4 H4 120.5(11) . . ?
C4 C4A C9A 120.29(16) . . ?
C4 C4A C4B 133.29(16) . . ?
C9A C4A C4B 106.39(14) . . ?
C5 C4B C8A 120.01(16) . . ?
C5 C4B C4A 133.51(16) . . ?
C8A C4B C4A 106.45(14) . . ?
C6 C5 C4B 118.22(16) . . ?
C6 C5 H5 120.3(12) . . ?
C4B C5 H5 121.5(12) . . ?
C5 C6 C7 121.67(17) . . ?
C5 C6 H6 120.7(12) . . ?
C7 C6 H6 117.6(12) . . ?
C8 C7 C6 121.33(17) . . ?
C8 C7 H7 120.8(11) . . ?
C6 C7 H7 117.8(11) . . ?
C7 C8 C8A 117.19(15) . . ?
C7 C8 N18 123.86(15) . . ?
C8A C8 N18 118.95(15) . . ?
N9 C8A C8 128.38(15) . . ?
N9 C8A C4B 109.95(14) . . ?
C8 C8A C4B 121.58(15) . . ?
C1 C9A N9 128.70(15) . . ?
C1 C9A C4A 121.33(15) . . ?
N9 C9A C4A 109.73(15) . . ?
C8A N9 C9A 107.44(14) . . ?
C8A N9 H9 124.3(13) . . ?
C9A N9 H9 122.2(13) . . ?
C11 N10 C1 121.63(14) . . ?
C11 N10 H10 121.3(12) . . ?
C1 N10 H10 116.4(12) . . ?
O11 C11 N10 122.15(16) . . ?
O11 C11 C12 120.33(15) . . ?
N10 C11 C12 117.51(14) . . ?
C17 C12 C13 118.75(16) . . ?
C17 C12 C11 124.32(15) . . ?
C13 C12 C11 116.93(15) . . ?
C14 C13 C12 120.72(17) . . ?
C14 C13 H13 119.6(11) . . ?
C12 C13 H13 119.7(11) . . ?
C13 C14 C15 120.12(18) . . ?
C13 C14 H14 118.1(13) . . ?
C15 C14 H14 121.8(13) . . ?
C14 C15 C16 119.53(18) . . ?
C14 C15 H15 122.1(12) . . ?
C16 C15 H15 118.4(12) . . ?
C17 C16 C15 120.72(18) . . ?
C17 C16 H16 120.0(12) . . ?
C15 C16 H16 119.1(12) . . ?
C16 C17 C12 120.14(17) . . ?
C16 C17 H17 119.1(10) . . ?
C12 C17 H17 120.7(10) . . ?
C19 N18 C8 124.49(16) . . ?
C19 N18 H18 118.2(13) . . ?
C8 N18 H18 117.0(14) . . ?
O19 C19 N18 122.80(16) . . ?
O19 C19 C20 120.85(16) . . ?
N18 C19 C20 116.34(16) . . ?
C25 C20 C21 119.29(17) . . ?
C25 C20 C19 123.81(16) . . ?
C21 C20 C19 116.89(17) . . ?
C22 C21 C20 120.4(2) . . ?
C22 C21 H21 118.6(12) . . ?
C20 C21 H21 121.0(12) . . ?
C23 C22 C21 120.1(2) . . ?
C23 C22 H22 121.5(13) . . ?
C21 C22 H22 118.4(14) . . ?
C22 C23 C24 119.96(19) . . ?
C22 C23 H23 121.2(13) . . ?
C24 C23 H23 118.8(13) . . ?
C25 C24 C23 120.1(2) . . ?
C25 C24 H24 121.6(12) . . ?
C23 C24 H24 118.1(12) . . ?
C24 C25 C20 120.24(18) . . ?
C24 C25 H25 119.5(11) . . ?
C20 C25 H25 120.3(11) . . ?
C2BE C1BE C6BE 118.96(17) . . ?
C2BE C1BE C7BE 120.86(17) . . ?
C6BE C1BE C7BE 120.18(16) . . ?
C1BE C2BE C3BE 120.45(19) . . ?
C1BE C2BE H2BE 122.0(11) . . ?
C3BE C2BE H2BE 117.3(11) . . ?
C4BE C3BE C2BE 120.04(19) . . ?
C4BE C3BE H3BE 120.9(13) . . ?
C2BE C3BE H3BE 119.0(14) . . ?
C3BE C4BE C5BE 120.02(19) . . ?
C3BE C4BE H4BE 119.9(13) . . ?
C5BE C4BE H4BE 120.1(13) . . ?
C4BE C5BE C6BE 120.1(2) . . ?
C4BE C5BE H5BE 121.5(14) . . ?
C6BE C5BE H5BE 118.3(14) . . ?
C5BE C6BE C1BE 120.42(19) . . ?
C5BE C6BE H6BE 120.1(12) . . ?
C1BE C6BE H6BE 119.4(12) . . ?
O2BE C7BE O1BE 123.99(17) . . ?
O2BE C7BE C1BE 117.99(16) . . ?
O1BE C7BE C1BE 117.98(17) . . ?
C35 N26 C27 106.68(12) . . ?
C35 N26 C39 110.91(13) . . ?
C27 N26 C39 110.67(13) . . ?
C35 N26 C31 110.79(13) . . ?
C27 N26 C31 111.04(13) . . ?
C39 N26 C31 106.80(12) . . ?
C28 C27 N26 116.24(14) . . ?
C28 C27 H27A 110.1(11) . . ?
N26 C27 H27A 105.6(11) . . ?
C28 C27 H27B 109.0(11) . . ?
N26 C27 H27B 107.5(11) . . ?
H27A C27 H27B 108.0(16) . . ?
C29 C28 C27 109.22(15) . . ?
C29 C28 H28A 109.8(12) . . ?
C27 C28 H28A 111.9(12) . . ?
C29 C28 H28B 111.1(10) . . ?
C27 C28 H28B 110.0(11) . . ?
H28A C28 H28B 104.8(16) . . ?
C28 C29 C30 113.24(17) . . ?
C28 C29 H29A 109.2(13) . . ?
C30 C29 H29A 110.7(13) . . ?
C28 C29 H29B 108.1(13) . . ?
C30 C29 H29B 107.5(12) . . ?
H29A C29 H29B 107.8(18) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 N26 115.63(14) . . ?
C32 C31 H31A 112.1(10) . . ?
N26 C31 H31A 104.4(10) . . ?
C32 C31 H31B 113.1(11) . . ?
N26 C31 H31B 104.3(11) . . ?
H31A C31 H31B 106.5(15) . . ?
C31 C32 C33 110.75(15) . . ?
C31 C32 H32A 110.9(12) . . ?
C33 C32 H32A 109.2(12) . . ?
C31 C32 H32B 113.0(12) . . ?
C33 C32 H32B 105.7(12) . . ?
H32A C32 H32B 107.1(17) . . ?
C32 C33 C34 111.75(15) . . ?
C32 C33 H33A 108.5(12) . . ?
C34 C33 H33A 108.3(12) . . ?
C32 C33 H33B 108.5(11) . . ?
C34 C33 H33B 110.3(11) . . ?
H33A C33 H33B 109.5(16) . . ?
C33 C34 H34A 113.1(13) . . ?
C33 C34 H34B 112.3(13) . . ?
H34A C34 H34B 105.6(18) . . ?
C33 C34 H34C 112.8(13) . . ?
H34A C34 H34C 107.0(18) . . ?
H34B C34 H34C 105.5(18) . . ?
C36 C35 N26 116.02(14) . . ?
C36 C35 H35A 112.1(11) . . ?
N26 C35 H35A 106.6(11) . . ?
C36 C35 H35B 111.0(10) . . ?
N26 C35 H35B 103.7(10) . . ?
H35A C35 H35B 106.7(15) . . ?
C35 C36 C37 110.36(15) . . ?
C35 C36 H36A 111.9(11) . . ?
C37 C36 H36A 108.3(11) . . ?
C35 C36 H36B 111.0(11) . . ?
C37 C36 H36B 106.6(10) . . ?
H36A C36 H36B 108.5(15) . . ?
C38 C37 C36 113.95(16) . . ?
C38 C37 H37A 107.0(11) . . ?
C36 C37 H37A 109.8(11) . . ?
C38 C37 H37B 109.4(12) . . ?
C36 C37 H37B 109.4(12) . . ?
H37A C37 H37B 107.0(17) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 N26 115.17(14) . . ?
C40 C39 H39A 110.8(11) . . ?
N26 C39 H39A 108.4(11) . . ?
C40 C39 H39B 110.1(11) . . ?
N26 C39 H39B 106.7(10) . . ?
H39A C39 H39B 105.2(15) . . ?
C39 C40 C41 110.50(15) . . ?
C39 C40 H40A 110.9(12) . . ?
C41 C40 H40A 108.3(12) . . ?
C39 C40 H40B 110.6(12) . . ?
C41 C40 H40B 109.7(12) . . ?
H40A C40 H40B 106.7(17) . . ?
C42 C41 C40 113.9(2) . . ?
C42 C41 H41A 110.1(11) . . ?
C40 C41 H41A 107.2(11) . . ?
C42 C41 H41B 110.6(12) . . ?
C40 C41 H41B 105.6(12) . . ?
H41A C41 H41B 109.1(17) . . ?
C41 C42 H42A 111(2) . . ?
C41 C42 H42B 110.2(15) . . ?
H42A C42 H42B 117(2) . . ?
C41 C42 H42C 107.4(16) . . ?
H42A C42 H42C 107(3) . . ?
H42B C42 H42C 104(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A C1 C2 C3 1.7(2) . . . . ?
N10 C1 C2 C3 -176.95(15) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C2 C3 C4 C4A -1.4(3) . . . . ?
C3 C4 C4A C9A -1.6(2) . . . . ?
C3 C4 C4A C4B 176.10(17) . . . . ?
C4 C4A C4B C5 -2.2(3) . . . . ?
C9A C4A C4B C5 175.71(17) . . . . ?
C4 C4A C4B C8A -179.88(17) . . . . ?
C9A C4A C4B C8A -1.97(17) . . . . ?
C8A C4B C5 C6 -0.6(2) . . . . ?
C4A C4B C5 C6 -178.07(17) . . . . ?
C4B C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C6 C7 C8 C8A -0.9(2) . . . . ?
C6 C7 C8 N18 179.24(16) . . . . ?
C7 C8 C8A N9 176.39(15) . . . . ?
N18 C8 C8A N9 -3.8(3) . . . . ?
C7 C8 C8A C4B 0.3(2) . . . . ?
N18 C8 C8A C4B -179.89(14) . . . . ?
C5 C4B C8A N9 -176.26(14) . . . . ?
C4A C4B C8A N9 1.80(17) . . . . ?
C5 C4B C8A C8 0.5(2) . . . . ?
C4A C4B C8A C8 178.58(14) . . . . ?
C2 C1 C9A N9 -178.60(15) . . . . ?
N10 C1 C9A N9 0.1(2) . . . . ?
C2 C1 C9A C4A -4.7(2) . . . . ?
N10 C1 C9A C4A 173.94(14) . . . . ?
C4 C4A C9A C1 4.8(2) . . . . ?
C4B C4A C9A C1 -173.45(14) . . . . ?
C4 C4A C9A N9 179.71(14) . . . . ?
C4B C4A C9A N9 1.48(17) . . . . ?
C8 C8A N9 C9A -177.41(15) . . . . ?
C4B C8A N9 C9A -0.91(17) . . . . ?
C1 C9A N9 C8A 174.06(16) . . . . ?
C4A C9A N9 C8A -0.39(17) . . . . ?
C2 C1 N10 C11 45.3(2) . . . . ?
C9A C1 N10 C11 -133.27(16) . . . . ?
C1 N10 C11 O11 2.0(2) . . . . ?
C1 N10 C11 C12 -178.97(14) . . . . ?
O11 C11 C12 C17 -167.13(16) . . . . ?
N10 C11 C12 C17 13.8(2) . . . . ?
O11 C11 C12 C13 12.1(2) . . . . ?
N10 C11 C12 C13 -166.92(15) . . . . ?
C17 C12 C13 C14 -1.0(3) . . . . ?
C11 C12 C13 C14 179.69(16) . . . . ?
C12 C13 C14 C15 1.0(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C17 -1.1(3) . . . . ?
C15 C16 C17 C12 1.0(3) . . . . ?
C13 C12 C17 C16 0.0(3) . . . . ?
C11 C12 C17 C16 179.25(16) . . . . ?
C7 C8 N18 C19 -36.6(2) . . . . ?
C8A C8 N18 C19 143.60(16) . . . . ?
C8 N18 C19 O19 -1.5(3) . . . . ?
C8 N18 C19 C20 179.28(15) . . . . ?
O19 C19 C20 C25 159.13(18) . . . . ?
N18 C19 C20 C25 -21.6(2) . . . . ?
O19 C19 C20 C21 -19.6(3) . . . . ?
N18 C19 C20 C21 159.63(17) . . . . ?
C25 C20 C21 C22 -1.0(3) . . . . ?
C19 C20 C21 C22 177.82(18) . . . . ?
C20 C21 C22 C23 0.7(3) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C20 -0.2(3) . . . . ?
C21 C20 C25 C24 0.7(3) . . . . ?
C19 C20 C25 C24 -178.01(16) . . . . ?
C6BE C1BE C2BE C3BE 0.3(3) . . . . ?
C7BE C1BE C2BE C3BE 179.50(17) . . . . ?
C1BE C2BE C3BE C4BE 0.0(3) . . . . ?
C2BE C3BE C4BE C5BE -0.1(3) . . . . ?
C3BE C4BE C5BE C6BE -0.1(3) . . . . ?
C4BE C5BE C6BE C1BE 0.4(3) . . . . ?
C2BE C1BE C6BE C5BE -0.5(3) . . . . ?
C7BE C1BE C6BE C5BE -179.69(18) . . . . ?
C2BE C1BE C7BE O2BE 14.5(3) . . . . ?
C6BE C1BE C7BE O2BE -166.34(18) . . . . ?
C2BE C1BE C7BE O1BE -163.34(17) . . . . ?
C6BE C1BE C7BE O1BE 15.8(2) . . . . ?
C35 N26 C27 C28 -177.05(15) . . . . ?
C39 N26 C27 C28 -56.30(19) . . . . ?
C31 N26 C27 C28 62.13(19) . . . . ?
N26 C27 C28 C29 -168.32(16) . . . . ?
C27 C28 C29 C30 -171.78(16) . . . . ?
C35 N26 C31 C32 -66.08(19) . . . . ?
C27 N26 C31 C32 52.28(19) . . . . ?
C39 N26 C31 C32 173.02(15) . . . . ?
N26 C31 C32 C33 170.44(14) . . . . ?
C31 C32 C33 C34 177.95(16) . . . . ?
C27 N26 C35 C36 177.77(15) . . . . ?
C39 N26 C35 C36 57.18(19) . . . . ?
C31 N26 C35 C36 -61.25(19) . . . . ?
N26 C35 C36 C37 -165.83(15) . . . . ?
C35 C36 C37 C38 69.1(2) . . . . ?
C35 N26 C39 C40 51.61(19) . . . . ?
C27 N26 C39 C40 -66.59(19) . . . . ?
C31 N26 C39 C40 172.42(15) . . . . ?
N26 C39 C40 C41 177.41(14) . . . . ?
C39 C40 C41 C42 -76.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N9 H9 O1BE 0.95(2) 2.44(2) 3.277(2) 147.7(17) .
N9 H9 O2BE 0.95(2) 1.99(2) 2.834(2) 147.2(18) .
N10 H10 O1BE 0.92(2) 1.95(2) 2.8580(19) 173.1(18) .
N18 H18 O2BE 0.90(2) 1.96(2) 2.835(2) 164.4(19) .

_refine_diff_density_max         0.471
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.106


_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_Karb_5c_benz
_database_code_depnum_ccdc_archive 'CCDC 1826923'
_audit_update_record             
;
2018-06-19 deposited with the CCDC.
2018-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H68 N4 O4'
_chemical_formula_weight         729.03

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

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

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

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

_cell_length_a                   13.6871(8)
_cell_length_b                   18.5215(11)
_cell_length_c                   18.0498(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.711(5)
_cell_angle_gamma                90
_cell_volume                     4333.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8000
_cell_measurement_theta_min      3
_cell_measurement_theta_max      22

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_F_000             1592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   
;
CrysAlis RED
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  KM4CCD
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 8.6479
_diffrn_reflns_number            54663
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.703
_diffrn_reflns_theta_max         25.199
_diffrn_reflns_theta_full        25.199
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7800
_reflns_number_gt                5514
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       CrysALisCCD
_computing_cell_refinement       CrysAlisRED
_computing_data_reduction        CrysAlisRED
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  'XCIF (Bruker AXS Inc., 2013)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0894P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0029(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7800
_refine_ls_number_parameters     733
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1561
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1BE O 0.02188(11) 0.21419(8) 0.80046(9) 0.0261(4) Uani 1 1 d . . . . .
C1BE C 0.13131(17) 0.12755(11) 0.77087(13) 0.0237(5) Uani 1 1 d . . . . .
C2BE C 0.1955(2) 0.06832(13) 0.79491(15) 0.0348(6) Uani 1 1 d . . . . .
O2BE O 0.11733(12) 0.14390(8) 0.89775(9) 0.0280(4) Uani 1 1 d . . . . .
C3BE C 0.2363(2) 0.03356(14) 0.74288(17) 0.0438(7) Uani 1 1 d . . . . .
C4BE C 0.2135(2) 0.05855(14) 0.66641(16) 0.0386(6) Uani 1 1 d . . . . .
C5BE C 0.1508(2) 0.11849(13) 0.64248(15) 0.0334(6) Uani 1 1 d . . . . .
C6BE C 0.10973(18) 0.15267(12) 0.69439(14) 0.0274(5) Uani 1 1 d . . . . .
C7BE C 0.08609(16) 0.16467(11) 0.82730(13) 0.0225(5) Uani 1 1 d . . . . .
H2BE H 0.209(2) 0.0518(14) 0.8523(17) 0.045(8) Uiso 1 1 d . . . . .
H3BE H 0.301(3) -0.008(2) 0.767(2) 0.091(12) Uiso 1 1 d . . . . .
H4BE H 0.243(2) 0.0325(14) 0.6287(16) 0.038(7) Uiso 1 1 d . . . . .
H5BE H 0.135(2) 0.1410(14) 0.5867(16) 0.038(7) Uiso 1 1 d . . . . .
H6BE H 0.063(2) 0.1974(15) 0.6766(16) 0.044(7) Uiso 1 1 d . . . . .
C1 C -0.00557(16) 0.34136(11) 0.95246(13) 0.0236(5) Uani 1 1 d . . . . .
C2 C -0.04974(17) 0.40480(12) 0.96676(13) 0.0275(5) Uani 1 1 d . . . . .
C3 C -0.10284(17) 0.40771(12) 1.02187(14) 0.0287(5) Uani 1 1 d . . . . .
C4 C -0.11125(17) 0.34738(12) 1.06457(14) 0.0276(5) Uani 1 1 d . . . . .
C4A C -0.06563(16) 0.28260(11) 1.05220(13) 0.0240(5) Uani 1 1 d . . . . .
C4B C -0.05239(16) 0.21206(12) 1.08828(13) 0.0251(5) Uani 1 1 d . . . . .
C5 C -0.08274(18) 0.18076(13) 1.14819(14) 0.0302(5) Uani 1 1 d . . . . .
C6 C -0.05544(19) 0.11047(14) 1.16796(14) 0.0320(5) Uani 1 1 d . . . . .
C7 C 0.00224(18) 0.06943(12) 1.13103(13) 0.0279(5) Uani 1 1 d . . . . .
C8 C 0.03444(16) 0.09921(11) 1.07192(12) 0.0230(5) Uani 1 1 d . . . . .
C8A C 0.00467(16) 0.17083(11) 1.05044(12) 0.0224(5) Uani 1 1 d . . . . .
N9 N 0.02681(13) 0.21233(9) 0.99404(10) 0.0210(4) Uani 1 1 d . . . . .
C9A C -0.01470(15) 0.28040(11) 0.99525(12) 0.0214(5) Uani 1 1 d . . . . .
N10 N 0.04780(14) 0.33528(10) 0.89684(11) 0.0239(4) Uani 1 1 d . . . . .
C11 C 0.13231(17) 0.37524(11) 0.90013(13) 0.0255(5) Uani 1 1 d . . . . .
O11 O 0.16675(13) 0.42339(8) 0.94837(10) 0.0325(4) Uani 1 1 d . . . . .
C12 C 0.18359(19) 0.35474(13) 0.84012(14) 0.0292(5) Uani 1 1 d . . . . .
C13 C 0.27579(19) 0.30496(14) 0.87409(15) 0.0312(5) Uani 1 1 d . . . . .
C14 C 0.3294(2) 0.28695(16) 0.81451(17) 0.0403(6) Uani 1 1 d . . . . .
C15 C 0.4171(3) 0.2340(2) 0.8443(2) 0.0633(10) Uani 1 1 d . . . . .
N16 N 0.09490(14) 0.06380(9) 1.03320(11) 0.0224(4) Uani 1 1 d . . . . .
C17 C 0.15351(16) 0.00399(11) 1.05757(12) 0.0229(5) Uani 1 1 d . . . . .
O17 O 0.15190(12) -0.03255(8) 1.11374(9) 0.0319(4) Uani 1 1 d . . . . .
C18 C 0.22413(18) -0.01313(12) 1.01007(15) 0.0285(5) Uani 1 1 d . . . . .
C19A C 0.2676(2) -0.08884(14) 1.02243(15) 0.0390(6) Uani 0.618(5) 1 d D . P A 1
H19A H 0.210557 -0.122825 1.019106 0.047 Uiso 0.618(5) 1 calc R U P A 1
H19B H 0.317169 -0.092119 1.076084 0.047 Uiso 0.618(5) 1 calc R U P A 1
C20A C 0.3226(6) -0.1138(4) 0.9645(4) 0.0355(16) Uani 0.618(5) 1 d D . P A 1
H20A H 0.279122 -0.101243 0.910693 0.043 Uiso 0.618(5) 1 calc R U P A 1
H20B H 0.388513 -0.087271 0.975630 0.043 Uiso 0.618(5) 1 calc R U P A 1
C21A C 0.3447(3) -0.1941(2) 0.9682(3) 0.0422(12) Uani 0.618(5) 1 d D . P A 1
H21A H 0.388585 -0.207034 1.021013 0.063 Uiso 0.618(5) 1 calc R U P A 1
H21B H 0.380102 -0.206427 0.930500 0.063 Uiso 0.618(5) 1 calc R U P A 1
H21C H 0.279617 -0.220933 0.955359 0.063 Uiso 0.618(5) 1 calc R U P A 1
C19B C 0.2676(2) -0.08884(14) 1.02243(15) 0.0390(6) Uani 0.382(5) 1 d D . P A 2
H19C H 0.212288 -0.124664 1.000199 0.047 Uiso 0.382(5) 1 calc R U P A 2
H19D H 0.299465 -0.098840 1.078958 0.047 Uiso 0.382(5) 1 calc R U P A 2
C20B C 0.3521(9) -0.0933(7) 0.9791(8) 0.048(3) Uani 0.382(5) 1 d D . P A 2
H20C H 0.383723 -0.141792 0.990376 0.058 Uiso 0.382(5) 1 calc R U P A 2
H20D H 0.314073 -0.091993 0.922294 0.058 Uiso 0.382(5) 1 calc R U P A 2
C21B C 0.4397(6) -0.0402(4) 0.9933(6) 0.063(3) Uani 0.382(5) 1 d D . P A 2
H21D H 0.411975 0.009000 0.984580 0.094 Uiso 0.382(5) 1 calc R U P A 2
H21E H 0.478348 -0.050225 0.957191 0.094 Uiso 0.382(5) 1 calc R U P A 2
H21F H 0.485644 -0.044858 1.047302 0.094 Uiso 0.382(5) 1 calc R U P A 2
H2 H -0.0408(17) 0.4490(13) 0.9378(14) 0.025(6) Uiso 1 1 d . . . . .
H3 H -0.1287(18) 0.4537(14) 1.0301(14) 0.028(6) Uiso 1 1 d . . . . .
H4 H -0.1425(18) 0.3504(12) 1.1063(15) 0.026(6) Uiso 1 1 d . . . . .
H5 H -0.1218(18) 0.2115(13) 1.1778(14) 0.030(6) Uiso 1 1 d . . . . .
H6 H -0.068(2) 0.0894(14) 1.2081(16) 0.034(7) Uiso 1 1 d . . . . .
H7 H 0.0192(18) 0.0170(13) 1.1411(13) 0.024(6) Uiso 1 1 d . . . . .
H9 H 0.059(2) 0.1892(16) 0.9532(18) 0.057(9) Uiso 1 1 d . . . . .
H10 H 0.033(2) 0.2975(14) 0.8626(16) 0.037(7) Uiso 1 1 d . . . . .
H12A H 0.132(2) 0.3301(13) 0.7917(15) 0.033(7) Uiso 1 1 d . . . . .
H12B H 0.2007(19) 0.3975(14) 0.8200(15) 0.035(7) Uiso 1 1 d . . . . .
H13A H 0.253(2) 0.2589(16) 0.8903(17) 0.047(8) Uiso 1 1 d . . . . .
H13B H 0.328(2) 0.3278(14) 0.9188(16) 0.037(7) Uiso 1 1 d . . . . .
H14A H 0.279(2) 0.2667(14) 0.7664(17) 0.039(7) Uiso 1 1 d . . . . .
H14B H 0.361(2) 0.3276(15) 0.8022(16) 0.043(8) Uiso 1 1 d . . . . .
H15A H 0.396(3) 0.189(2) 0.856(2) 0.075(12) Uiso 1 1 d . . . . .
H15B H 0.474(4) 0.252(2) 0.888(3) 0.098(15) Uiso 1 1 d . . . . .
H15C H 0.450(2) 0.2219(17) 0.802(2) 0.062(9) Uiso 1 1 d . . . . .
H16 H 0.0971(18) 0.0815(12) 0.9919(15) 0.022(6) Uiso 1 1 d . . . . .
H18A H 0.180(2) -0.0065(13) 0.9555(16) 0.032(6) Uiso 1 1 d . . . . .
H18B H 0.278(2) 0.0238(15) 1.0237(16) 0.043(8) Uiso 1 1 d . . . . .
N22 N 0.74232(13) 0.13247(9) 0.68940(10) 0.0226(4) Uani 1 1 d . . . . .
C23 C 0.64099(17) 0.09173(12) 0.67134(14) 0.0257(5) Uani 1 1 d . . . . .
C24 C 0.63974(18) 0.03465(13) 0.73128(14) 0.0285(5) Uani 1 1 d . . . . .
C25 C 0.53076(18) 0.01522(13) 0.72914(15) 0.0312(5) Uani 1 1 d . . . . .
C26 C 0.5320(2) -0.04362(14) 0.78841(16) 0.0413(6) Uani 1 1 d . . . . .
H26A H 0.560858 -0.088008 0.774398 0.062 Uiso 1 1 calc R U . . .
H26B H 0.461403 -0.052761 0.788290 0.062 Uiso 1 1 calc R U . . .
H26C H 0.574453 -0.027928 0.840672 0.062 Uiso 1 1 calc R U . . .
C27 C 0.83166(17) 0.08106(12) 0.69802(13) 0.0237(5) Uani 1 1 d . . . . .
C28 C 0.82362(18) 0.03578(13) 0.62611(14) 0.0277(5) Uani 1 1 d . . . . .
C29 C 0.9172(2) -0.01341(13) 0.64207(15) 0.0312(5) Uani 1 1 d . . . . .
C30 C 0.9158(2) -0.05710(16) 0.57018(17) 0.0416(7) Uani 1 1 d . . . . .
C31 C 0.73004(17) 0.18527(12) 0.62221(13) 0.0237(5) Uani 1 1 d . . . . .
C32 C 0.82852(17) 0.22191(12) 0.62037(14) 0.0259(5) Uani 1 1 d . . . . .
C33 C 0.80288(19) 0.28856(13) 0.56856(15) 0.0297(5) Uani 1 1 d . . . . .
C34 C 0.8974(2) 0.31915(14) 0.55266(18) 0.0386(6) Uani 1 1 d . . . . .
C35 C 0.76582(17) 0.17397(12) 0.76656(13) 0.0236(5) Uani 1 1 d . . . . .
C36 C 0.67434(18) 0.21565(12) 0.77669(14) 0.0277(5) Uani 1 1 d . . . . .
C37 C 0.7112(2) 0.27865(13) 0.83365(15) 0.0336(6) Uani 1 1 d . . . . .
C38 C 0.7505(2) 0.34141(14) 0.79701(18) 0.0408(6) Uani 1 1 d . . . . .
H23A H 0.5873(19) 0.1250(13) 0.6654(14) 0.024(6) Uiso 1 1 d . . . . .
H23B H 0.6269(17) 0.0684(12) 0.6187(15) 0.024(6) Uiso 1 1 d . . . . .
H24A H 0.678(2) 0.0515(14) 0.7812(17) 0.037(7) Uiso 1 1 d . . . . .
H24B H 0.675(2) -0.0082(14) 0.7176(15) 0.036(7) Uiso 1 1 d . . . . .
H25A H 0.4923(19) 0.0599(14) 0.7384(14) 0.031(6) Uiso 1 1 d . . . . .
H25B H 0.487(2) 0.0009(14) 0.6764(16) 0.035(7) Uiso 1 1 d . . . . .
H27A H 0.8387(16) 0.0511(12) 0.7456(13) 0.019(5) Uiso 1 1 d . . . . .
H27B H 0.8934(18) 0.1114(12) 0.7126(13) 0.022(6) Uiso 1 1 d . . . . .
H28A H 0.757(2) 0.0042(13) 0.6100(14) 0.032(6) Uiso 1 1 d . . . . .
H28B H 0.8172(19) 0.0625(14) 0.5843(16) 0.030(7) Uiso 1 1 d . . . . .
H29A H 0.915(2) -0.0476(14) 0.6852(16) 0.037(7) Uiso 1 1 d . . . . .
H29B H 0.973(2) 0.0150(14) 0.6552(14) 0.029(7) Uiso 1 1 d . . . . .
H30A H 0.853(2) -0.0903(15) 0.5516(16) 0.045(8) Uiso 1 1 d . . . . .
H30B H 0.915(2) -0.0268(16) 0.5295(18) 0.049(8) Uiso 1 1 d . . . . .
H30C H 0.972(2) -0.0909(16) 0.5806(18) 0.052(8) Uiso 1 1 d . . . . .
H31A H 0.7018(17) 0.1565(12) 0.5761(14) 0.022(6) Uiso 1 1 d . . . . .
H31B H 0.6818(19) 0.2216(13) 0.6274(14) 0.029(6) Uiso 1 1 d . . . . .
H32A H 0.8712(19) 0.1877(13) 0.6011(14) 0.028(6) Uiso 1 1 d . . . . .
H32B H 0.8749(18) 0.2355(12) 0.6746(15) 0.027(6) Uiso 1 1 d . . . . .
H33A H 0.751(2) 0.2792(13) 0.5214(16) 0.033(7) Uiso 1 1 d . . . . .
H33B H 0.7735(19) 0.3265(13) 0.5935(14) 0.029(6) Uiso 1 1 d . . . . .
H34A H 0.931(2) 0.2844(15) 0.5272(16) 0.041(7) Uiso 1 1 d . . . . .
H34B H 0.957(2) 0.3340(14) 0.6066(17) 0.042(7) Uiso 1 1 d . . . . .
H34C H 0.883(2) 0.3607(16) 0.5208(18) 0.048(8) Uiso 1 1 d . . . . .
H35A H 0.8258(16) 0.2063(11) 0.7676(12) 0.012(5) Uiso 1 1 d . . . . .
H35B H 0.7952(17) 0.1361(12) 0.8083(14) 0.021(6) Uiso 1 1 d . . . . .
H36A H 0.6275(19) 0.2361(13) 0.7258(15) 0.030(6) Uiso 1 1 d . . . . .
H36B H 0.624(2) 0.1839(14) 0.7939(15) 0.035(7) Uiso 1 1 d . . . . .
H37A H 0.762(2) 0.2634(14) 0.8766(17) 0.039(7) Uiso 1 1 d . . . . .
H37B H 0.648(2) 0.2967(14) 0.8505(15) 0.037(7) Uiso 1 1 d . . . . .
H38A H 0.816(2) 0.3276(15) 0.7801(17) 0.048(8) Uiso 1 1 d . . . . .
H38B H 0.768(3) 0.3851(19) 0.837(2) 0.071(10) Uiso 1 1 d . . . . .
H38C H 0.697(2) 0.3599(14) 0.7512(17) 0.040(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1BE C7BE 1.255(3) . ?
C1BE C2BE 1.385(3) . ?
C1BE C6BE 1.396(3) . ?
C1BE C7BE 1.516(3) . ?
C2BE C3BE 1.395(3) . ?
C2BE H2BE 1.04(3) . ?
O2BE C7BE 1.264(3) . ?
C3BE C4BE 1.393(4) . ?
C3BE H3BE 1.15(4) . ?
C4BE C5BE 1.385(4) . ?
C4BE H4BE 1.02(3) . ?
C5BE C6BE 1.390(3) . ?
C5BE H5BE 1.05(3) . ?
C6BE H6BE 1.03(3) . ?
C1 C2 1.383(3) . ?
C1 C9A 1.396(3) . ?
C1 N10 1.423(3) . ?
C2 C3 1.409(3) . ?
C2 H2 1.00(2) . ?
C3 C4 1.383(3) . ?
C3 H3 0.95(3) . ?
C4 C4A 1.403(3) . ?
C4 H4 0.98(2) . ?
C4A C9A 1.416(3) . ?
C4A C4B 1.445(3) . ?
C4B C5 1.402(3) . ?
C4B C8A 1.415(3) . ?
C5 C6 1.370(4) . ?
C5 H5 1.04(2) . ?
C6 C7 1.408(3) . ?
C6 H6 0.89(3) . ?
C7 C8 1.392(3) . ?
C7 H7 1.00(2) . ?
C8 N16 1.405(3) . ?
C8 C8A 1.405(3) . ?
C8A N9 1.384(3) . ?
N9 C9A 1.386(3) . ?
N9 H9 1.07(3) . ?
N10 C11 1.358(3) . ?
N10 H10 0.91(3) . ?
C11 O11 1.230(3) . ?
C11 C12 1.516(3) . ?
C12 C13 1.524(3) . ?
C12 H12A 1.04(3) . ?
C12 H12B 0.93(3) . ?
C13 C14 1.521(3) . ?
C13 H13A 0.98(3) . ?
C13 H13B 0.98(3) . ?
C14 C15 1.509(4) . ?
C14 H14A 1.00(3) . ?
C14 H14B 0.93(3) . ?
C15 H15A 0.93(4) . ?
C15 H15B 0.97(5) . ?
C15 H15C 1.04(3) . ?
N16 C17 1.356(3) . ?
N16 H16 0.82(3) . ?
C17 O17 1.225(3) . ?
C17 C18 1.517(3) . ?
C18 C19B 1.512(3) . ?
C18 C19A 1.512(3) . ?
C18 H18A 0.98(3) . ?
C18 H18B 0.98(3) . ?
C19A C20A 1.543(7) . ?
C19A H19A 0.9900 . ?
C19A H19B 0.9900 . ?
C20A C21A 1.515(8) . ?
C20A H20A 0.9900 . ?
C20A H20B 0.9900 . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
C19B C20B 1.592(11) . ?
C19B H19C 0.9900 . ?
C19B H19D 0.9900 . ?
C20B C21B 1.508(12) . ?
C20B H20C 0.9900 . ?
C20B H20D 0.9900 . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
N22 C27 1.518(3) . ?
N22 C23 1.519(3) . ?
N22 C31 1.525(3) . ?
N22 C35 1.532(3) . ?
C23 C24 1.517(3) . ?
C23 H23A 0.94(2) . ?
C23 H23B 1.00(2) . ?
C24 C25 1.523(3) . ?
C24 H24A 0.94(3) . ?
C24 H24B 1.00(3) . ?
C25 C26 1.523(3) . ?
C25 H25A 1.02(3) . ?
C25 H25B 0.98(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.519(3) . ?
C27 H27A 1.00(2) . ?
C27 H27B 0.98(2) . ?
C28 C29 1.522(3) . ?
C28 H28A 1.05(3) . ?
C28 H28B 0.88(3) . ?
C29 C30 1.524(4) . ?
C29 H29A 1.01(3) . ?
C29 H29B 0.89(3) . ?
C30 H30A 1.03(3) . ?
C30 H30B 0.92(3) . ?
C30 H30C 0.97(3) . ?
C31 C32 1.519(3) . ?
C31 H31A 0.96(2) . ?
C31 H31B 0.97(3) . ?
C32 C33 1.520(3) . ?
C32 H32A 1.00(3) . ?
C32 H32B 1.01(3) . ?
C33 C34 1.522(3) . ?
C33 H33A 0.93(3) . ?
C33 H33B 0.99(3) . ?
C34 H34A 0.99(3) . ?
C34 H34B 1.09(3) . ?
C34 H34C 0.94(3) . ?
C35 C36 1.531(3) . ?
C35 H35A 1.01(2) . ?
C35 H35B 1.01(2) . ?
C36 C37 1.530(3) . ?
C36 H36A 1.01(3) . ?
C36 H36B 1.02(3) . ?
C37 C38 1.519(4) . ?
C37 H37A 0.91(3) . ?
C37 H37B 1.06(3) . ?
C38 H38A 1.06(3) . ?
C38 H38B 1.06(4) . ?
C38 H38C 0.97(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2BE C1BE C6BE 119.1(2) . . ?
C2BE C1BE C7BE 120.2(2) . . ?
C6BE C1BE C7BE 120.7(2) . . ?
C1BE C2BE C3BE 120.3(2) . . ?
C1BE C2BE H2BE 116.2(15) . . ?
C3BE C2BE H2BE 123.4(15) . . ?
C4BE C3BE C2BE 120.2(2) . . ?
C4BE C3BE H3BE 119.7(19) . . ?
C2BE C3BE H3BE 119.0(19) . . ?
C5BE C4BE C3BE 119.7(2) . . ?
C5BE C4BE H4BE 120.6(15) . . ?
C3BE C4BE H4BE 119.7(15) . . ?
C4BE C5BE C6BE 119.9(2) . . ?
C4BE C5BE H5BE 122.6(14) . . ?
C6BE C5BE H5BE 117.4(14) . . ?
C5BE C6BE C1BE 120.8(2) . . ?
C5BE C6BE H6BE 120.0(15) . . ?
C1BE C6BE H6BE 119.3(15) . . ?
O1BE C7BE O2BE 125.40(19) . . ?
O1BE C7BE C1BE 117.29(19) . . ?
O2BE C7BE C1BE 117.30(19) . . ?
C2 C1 C9A 117.5(2) . . ?
C2 C1 N10 123.6(2) . . ?
C9A C1 N10 118.93(18) . . ?
C1 C2 C3 121.3(2) . . ?
C1 C2 H2 117.6(13) . . ?
C3 C2 H2 121.1(13) . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 122.3(15) . . ?
C2 C3 H3 116.5(15) . . ?
C3 C4 C4A 118.8(2) . . ?
C3 C4 H4 121.2(14) . . ?
C4A C4 H4 119.8(14) . . ?
C4 C4A C9A 119.2(2) . . ?
C4 C4A C4B 134.4(2) . . ?
C9A C4A C4B 106.36(18) . . ?
C5 C4B C8A 119.7(2) . . ?
C5 C4B C4A 134.1(2) . . ?
C8A C4B C4A 106.21(19) . . ?
C6 C5 C4B 118.0(2) . . ?
C6 C5 H5 121.9(13) . . ?
C4B C5 H5 120.0(13) . . ?
C5 C6 C7 122.5(2) . . ?
C5 C6 H6 121.5(17) . . ?
C7 C6 H6 115.7(17) . . ?
C8 C7 C6 120.8(2) . . ?
C8 C7 H7 114.3(13) . . ?
C6 C7 H7 124.7(13) . . ?
C7 C8 N16 125.3(2) . . ?
C7 C8 C8A 116.8(2) . . ?
N16 C8 C8A 117.93(19) . . ?
N9 C8A C8 127.90(19) . . ?
N9 C8A C4B 109.90(18) . . ?
C8 C8A C4B 122.2(2) . . ?
C8A N9 C9A 107.81(17) . . ?
C8A N9 H9 121.6(16) . . ?
C9A N9 H9 129.9(16) . . ?
N9 C9A C1 128.11(19) . . ?
N9 C9A C4A 109.71(18) . . ?
C1 C9A C4A 122.07(19) . . ?
C11 N10 C1 123.28(19) . . ?
C11 N10 H10 116.8(17) . . ?
C1 N10 H10 118.9(17) . . ?
O11 C11 N10 123.6(2) . . ?
O11 C11 C12 121.8(2) . . ?
N10 C11 C12 114.54(19) . . ?
C11 C12 C13 112.18(19) . . ?
C11 C12 H12A 111.2(14) . . ?
C13 C12 H12A 109.1(14) . . ?
C11 C12 H12B 107.3(16) . . ?
C13 C12 H12B 113.1(16) . . ?
H12A C12 H12B 104(2) . . ?
C14 C13 C12 111.9(2) . . ?
C14 C13 H13A 106.7(17) . . ?
C12 C13 H13A 110.4(17) . . ?
C14 C13 H13B 106.9(15) . . ?
C12 C13 H13B 110.9(15) . . ?
H13A C13 H13B 110(2) . . ?
C15 C14 C13 113.5(2) . . ?
C15 C14 H14A 108.6(15) . . ?
C13 C14 H14A 109.9(16) . . ?
C15 C14 H14B 103.9(17) . . ?
C13 C14 H14B 110.8(17) . . ?
H14A C14 H14B 110(2) . . ?
C14 C15 H15A 113(2) . . ?
C14 C15 H15B 114(3) . . ?
H15A C15 H15B 110(4) . . ?
C14 C15 H15C 111.1(18) . . ?
H15A C15 H15C 103(3) . . ?
H15B C15 H15C 105(3) . . ?
C17 N16 C8 126.99(19) . . ?
C17 N16 H16 115.4(16) . . ?
C8 N16 H16 117.5(16) . . ?
O17 C17 N16 123.6(2) . . ?
O17 C17 C18 122.42(19) . . ?
N16 C17 C18 113.91(19) . . ?
C19B C18 C17 113.7(2) . . ?
C19A C18 C17 113.7(2) . . ?
C19B C18 H18A 110.4(15) . . ?
C19A C18 H18A 110.4(15) . . ?
C17 C18 H18A 104.1(15) . . ?
C19B C18 H18B 112.5(16) . . ?
C19A C18 H18B 112.5(16) . . ?
C17 C18 H18B 106.1(16) . . ?
H18A C18 H18B 110(2) . . ?
C18 C19A C20A 115.7(4) . . ?
C18 C19A H19A 108.4 . . ?
C20A C19A H19A 108.4 . . ?
C18 C19A H19B 108.4 . . ?
C20A C19A H19B 108.4 . . ?
H19A C19A H19B 107.4 . . ?
C21A C20A C19A 113.5(5) . . ?
C21A C20A H20A 108.9 . . ?
C19A C20A H20A 108.9 . . ?
C21A C20A H20B 108.9 . . ?
C19A C20A H20B 108.9 . . ?
H20A C20A H20B 107.7 . . ?
C20A C21A H21A 109.5 . . ?
C20A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C20A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C18 C19B C20B 106.8(6) . . ?
C18 C19B H19C 110.4 . . ?
C20B C19B H19C 110.4 . . ?
C18 C19B H19D 110.4 . . ?
C20B C19B H19D 110.4 . . ?
H19C C19B H19D 108.6 . . ?
C21B C20B C19B 123.1(8) . . ?
C21B C20B H20C 106.6 . . ?
C19B C20B H20C 106.6 . . ?
C21B C20B H20D 106.6 . . ?
C19B C20B H20D 106.6 . . ?
H20C C20B H20D 106.5 . . ?
C20B C21B H21D 109.5 . . ?
C20B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C20B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C27 N22 C23 111.12(17) . . ?
C27 N22 C31 111.31(17) . . ?
C23 N22 C31 106.72(16) . . ?
C27 N22 C35 107.11(16) . . ?
C23 N22 C35 110.82(17) . . ?
C31 N22 C35 109.80(16) . . ?
C24 C23 N22 114.29(18) . . ?
C24 C23 H23A 110.6(14) . . ?
N22 C23 H23A 109.0(14) . . ?
C24 C23 H23B 109.4(13) . . ?
N22 C23 H23B 107.6(13) . . ?
H23A C23 H23B 105.6(19) . . ?
C23 C24 C25 112.44(19) . . ?
C23 C24 H24A 108.7(16) . . ?
C25 C24 H24A 110.2(16) . . ?
C23 C24 H24B 104.9(15) . . ?
C25 C24 H24B 110.9(15) . . ?
H24A C24 H24B 109(2) . . ?
C24 C25 C26 111.2(2) . . ?
C24 C25 H25A 110.9(14) . . ?
C26 C25 H25A 110.8(14) . . ?
C24 C25 H25B 111.9(15) . . ?
C26 C25 H25B 110.7(15) . . ?
H25A C25 H25B 101(2) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N22 C27 C28 115.06(18) . . ?
N22 C27 H27A 106.7(12) . . ?
C28 C27 H27A 112.8(12) . . ?
N22 C27 H27B 105.4(13) . . ?
C28 C27 H27B 111.5(13) . . ?
H27A C27 H27B 104.5(18) . . ?
C27 C28 C29 110.05(19) . . ?
C27 C28 H28A 111.3(13) . . ?
C29 C28 H28A 109.0(13) . . ?
C27 C28 H28B 112.4(16) . . ?
C29 C28 H28B 110.1(16) . . ?
H28A C28 H28B 104(2) . . ?
C28 C29 C30 112.1(2) . . ?
C28 C29 H29A 107.0(15) . . ?
C30 C29 H29A 109.1(15) . . ?
C28 C29 H29B 107.0(16) . . ?
C30 C29 H29B 108.3(16) . . ?
H29A C29 H29B 113(2) . . ?
C29 C30 H30A 112.1(16) . . ?
C29 C30 H30B 110.4(19) . . ?
H30A C30 H30B 108(2) . . ?
C29 C30 H30C 112.8(18) . . ?
H30A C30 H30C 102(2) . . ?
H30B C30 H30C 111(3) . . ?
C32 C31 N22 115.58(18) . . ?
C32 C31 H31A 110.0(14) . . ?
N22 C31 H31A 104.2(13) . . ?
C32 C31 H31B 109.2(14) . . ?
N22 C31 H31B 105.8(14) . . ?
H31A C31 H31B 112(2) . . ?
C31 C32 C33 110.18(19) . . ?
C31 C32 H32A 110.4(14) . . ?
C33 C32 H32A 110.2(14) . . ?
C31 C32 H32B 112.1(13) . . ?
C33 C32 H32B 110.0(13) . . ?
H32A C32 H32B 103.8(19) . . ?
C32 C33 C34 112.1(2) . . ?
C32 C33 H33A 111.6(16) . . ?
C34 C33 H33A 109.8(16) . . ?
C32 C33 H33B 110.2(14) . . ?
C34 C33 H33B 108.4(14) . . ?
H33A C33 H33B 104(2) . . ?
C33 C34 H34A 113.5(15) . . ?
C33 C34 H34B 111.5(14) . . ?
H34A C34 H34B 105(2) . . ?
C33 C34 H34C 113.6(18) . . ?
H34A C34 H34C 106(2) . . ?
H34B C34 H34C 107(2) . . ?
C36 C35 N22 114.85(18) . . ?
C36 C35 H35A 112.9(11) . . ?
N22 C35 H35A 104.3(12) . . ?
C36 C35 H35B 113.9(13) . . ?
N22 C35 H35B 104.2(13) . . ?
H35A C35 H35B 105.6(17) . . ?
C37 C36 C35 111.04(19) . . ?
C37 C36 H36A 107.5(14) . . ?
C35 C36 H36A 112.7(14) . . ?
C37 C36 H36B 110.1(14) . . ?
C35 C36 H36B 113.4(14) . . ?
H36A C36 H36B 102(2) . . ?
C38 C37 C36 112.2(2) . . ?
C38 C37 H37A 109.2(17) . . ?
C36 C37 H37A 109.5(17) . . ?
C38 C37 H37B 108.7(14) . . ?
C36 C37 H37B 108.0(14) . . ?
H37A C37 H37B 109(2) . . ?
C37 C38 H38A 112.9(15) . . ?
C37 C38 H38B 108.8(19) . . ?
H38A C38 H38B 111(2) . . ?
C37 C38 H38C 111.4(16) . . ?
H38A C38 H38C 108(2) . . ?
H38B C38 H38C 104(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6BE C1BE C2BE C3BE -1.2(4) . . . . ?
C7BE C1BE C2BE C3BE 179.3(2) . . . . ?
C1BE C2BE C3BE C4BE 0.5(4) . . . . ?
C2BE C3BE C4BE C5BE 0.5(4) . . . . ?
C3BE C4BE C5BE C6BE -0.9(4) . . . . ?
C4BE C5BE C6BE C1BE 0.3(4) . . . . ?
C2BE C1BE C6BE C5BE 0.8(3) . . . . ?
C7BE C1BE C6BE C5BE -179.7(2) . . . . ?
C2BE C1BE C7BE O1BE -174.3(2) . . . . ?
C6BE C1BE C7BE O1BE 6.2(3) . . . . ?
C2BE C1BE C7BE O2BE 6.8(3) . . . . ?
C6BE C1BE C7BE O2BE -172.7(2) . . . . ?
C9A C1 C2 C3 -0.6(3) . . . . ?
N10 C1 C2 C3 179.2(2) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 C4A 0.1(3) . . . . ?
C3 C4 C4A C9A -1.5(3) . . . . ?
C3 C4 C4A C4B 175.0(2) . . . . ?
C4 C4A C4B C5 2.2(4) . . . . ?
C9A C4A C4B C5 179.0(2) . . . . ?
C4 C4A C4B C8A -177.6(2) . . . . ?
C9A C4A C4B C8A -0.7(2) . . . . ?
C8A C4B C5 C6 0.0(3) . . . . ?
C4A C4B C5 C6 -179.7(2) . . . . ?
C4B C5 C6 C7 0.6(4) . . . . ?
C5 C6 C7 C8 0.0(4) . . . . ?
C6 C7 C8 N16 177.8(2) . . . . ?
C6 C7 C8 C8A -1.3(3) . . . . ?
C7 C8 C8A N9 179.8(2) . . . . ?
N16 C8 C8A N9 0.6(3) . . . . ?
C7 C8 C8A C4B 2.0(3) . . . . ?
N16 C8 C8A C4B -177.22(19) . . . . ?
C5 C4B C8A N9 -179.58(19) . . . . ?
C4A C4B C8A N9 0.2(2) . . . . ?
C5 C4B C8A C8 -1.4(3) . . . . ?
C4A C4B C8A C8 178.39(19) . . . . ?
C8 C8A N9 C9A -177.6(2) . . . . ?
C4B C8A N9 C9A 0.4(2) . . . . ?
C8A N9 C9A C1 175.2(2) . . . . ?
C8A N9 C9A C4A -0.9(2) . . . . ?
C2 C1 C9A N9 -176.7(2) . . . . ?
N10 C1 C9A N9 3.5(3) . . . . ?
C2 C1 C9A C4A -0.9(3) . . . . ?
N10 C1 C9A C4A 179.23(19) . . . . ?
C4 C4A C9A N9 178.45(19) . . . . ?
C4B C4A C9A N9 1.0(2) . . . . ?
C4 C4A C9A C1 2.0(3) . . . . ?
C4B C4A C9A C1 -175.41(19) . . . . ?
C2 C1 N10 C11 59.1(3) . . . . ?
C9A C1 N10 C11 -121.0(2) . . . . ?
C1 N10 C11 O11 -4.7(3) . . . . ?
C1 N10 C11 C12 173.97(19) . . . . ?
O11 C11 C12 C13 80.9(3) . . . . ?
N10 C11 C12 C13 -97.8(2) . . . . ?
C11 C12 C13 C14 -177.8(2) . . . . ?
C12 C13 C14 C15 -176.3(3) . . . . ?
C7 C8 N16 C17 -17.9(3) . . . . ?
C8A C8 N16 C17 161.2(2) . . . . ?
C8 N16 C17 O17 8.9(3) . . . . ?
C8 N16 C17 C18 -169.7(2) . . . . ?
O17 C17 C18 C19B 16.8(3) . . . . ?
N16 C17 C18 C19B -164.6(2) . . . . ?
O17 C17 C18 C19A 16.8(3) . . . . ?
N16 C17 C18 C19A -164.6(2) . . . . ?
C17 C18 C19A C20A 168.8(3) . . . . ?
C18 C19A C20A C21A -167.8(4) . . . . ?
C17 C18 C19B C20B -171.5(5) . . . . ?
C18 C19B C20B C21B 52.9(13) . . . . ?
C27 N22 C23 C24 56.8(2) . . . . ?
C31 N22 C23 C24 178.32(19) . . . . ?
C35 N22 C23 C24 -62.2(2) . . . . ?
N22 C23 C24 C25 158.7(2) . . . . ?
C23 C24 C25 C26 178.5(2) . . . . ?
C23 N22 C27 C28 60.1(2) . . . . ?
C31 N22 C27 C28 -58.7(2) . . . . ?
C35 N22 C27 C28 -178.72(18) . . . . ?
N22 C27 C28 C29 -179.89(19) . . . . ?
C27 C28 C29 C30 -176.9(2) . . . . ?
C27 N22 C31 C32 -47.7(2) . . . . ?
C23 N22 C31 C32 -169.07(19) . . . . ?
C35 N22 C31 C32 70.8(2) . . . . ?
N22 C31 C32 C33 -162.18(19) . . . . ?
C31 C32 C33 C34 -169.4(2) . . . . ?
C27 N22 C35 C36 -166.48(18) . . . . ?
C23 N22 C35 C36 -45.1(2) . . . . ?
C31 N22 C35 C36 72.5(2) . . . . ?
N22 C35 C36 C37 -155.51(19) . . . . ?
C35 C36 C37 C38 75.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N9 H9 O1BE 1.07(3) 2.68(3) 3.473(2) 131(2) .
N10 H10 O1BE 0.91(3) 1.89(3) 2.790(2) 171(2) .
N9 H9 O2BE 1.07(3) 1.69(3) 2.747(2) 172(3) .
N16 H16 O2BE 0.82(3) 2.15(3) 2.959(2) 169(2) .

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.079


_exptl_crystal_recrystallization_method 'Vapour deposition'
