# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_scd1591_HexNDI_100K_orange
_database_code_depnum_ccdc_archive 'CCDC 1839983'
#Added by publCIF



_audit_update_record             
;
2018-04-27 deposited with the CCDC.
2018-08-03 downloaded from the CCDC.
;
_publcif_datablock.id            {69dcc10a-2e90-4387-90d5-5ed0ead3820f}

_diffrn_radiation_monochromator  'HELIOS optics'
#Added by publCIF




_symmetry_space_group_name_hall  '-P 1'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H38 N2 O6'
_chemical_formula_sum            'C38 H38 N2 O6'
_chemical_formula_weight         618.70

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                   8.395(3)
_cell_length_b                   8.853(3)
_cell_length_c                   23.938(9)
_cell_angle_alpha                89.528(11)
_cell_angle_beta                 80.712(14)
_cell_angle_gamma                62.60(2)
_cell_volume                     1554.3(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6515
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.59

_exptl_crystal_description       fragment
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6535
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS (Krause, Herbst-Irmer, Sheldrick, & Stalke;  J. Appl. Cryst. 2015, 48,
3-10)
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS microfocus tube'
_diffrn_measurement_device_type  
;
Bruker Kappa D8 Quest CMOS diffractometer (with an Oxford Cryosystems cryostream
cooler)
;

_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20000
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.594
_diffrn_reflns_theta_max         27.624
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7191
_reflns_number_gt                4802
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL Intrinsic Phasing (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0526P)²+0.7977P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7191
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1333
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.81294(18) 1.10125(16) 0.42744(5) 0.0166(3) Uani 1 1 d . . . . .
O2 O 1.06713(18) 0.55100(17) 0.35410(6) 0.0187(3) Uani 1 1 d . . . . .
O3 O 0.56933(19) 0.37623(17) 0.58946(6) 0.0195(3) Uani 1 1 d . . . . .
O4 O 0.43821(18) 0.88089(17) 0.67888(5) 0.0180(3) Uani 1 1 d . . . . .
O5 O 1.29536(18) 0.98794(18) 0.19960(5) 0.0182(3) Uani 1 1 d . . . . .
O6 O 0.15220(18) 0.43451(17) 0.81625(6) 0.0193(3) Uani 1 1 d . . . . .
N1 N 0.9339(2) 0.8289(2) 0.38892(6) 0.0136(3) Uani 1 1 d . . . . .
N2 N 0.5030(2) 0.62837(19) 0.63428(6) 0.0124(3) Uani 1 1 d . . . . .
C1 C 0.8341(2) 0.9566(2) 0.43271(8) 0.0134(4) Uani 1 1 d . . . . .
C2 C 0.9636(2) 0.6589(2) 0.39127(8) 0.0140(4) Uani 1 1 d . . . . .
C3 C 0.8632(2) 0.6213(2) 0.44169(8) 0.0124(4) Uani 1 1 d . . . . .
C4 C 0.8670(3) 0.4645(2) 0.44424(8) 0.0151(4) Uani 1 1 d . . . . .
H4 H 0.9331 0.3804 0.4134 0.018 Uiso 1 1 calc R U . . .
C5 C 0.7735(2) 0.4279(2) 0.49222(8) 0.0147(4) Uani 1 1 d . . . . .
H5 H 0.7734 0.3206 0.4930 0.018 Uiso 1 1 calc R U . . .
C6 C 0.6823(2) 0.5459(2) 0.53799(8) 0.0132(4) Uani 1 1 d . . . . .
C7 C 0.5824(2) 0.5076(2) 0.58814(8) 0.0135(4) Uani 1 1 d . . . . .
C8 C 0.5050(2) 0.7852(2) 0.63644(8) 0.0131(4) Uani 1 1 d . . . . .
C9 C 0.5914(2) 0.8271(2) 0.58365(8) 0.0122(4) Uani 1 1 d . . . . .
C10 C 0.5825(2) 0.9863(2) 0.58053(8) 0.0129(4) Uani 1 1 d . . . . .
H10 H 0.5218 1.0683 0.6121 0.015 Uiso 1 1 calc R U . . .
C11 C 0.6630(2) 1.0272(2) 0.53070(8) 0.0140(4) Uani 1 1 d . . . . .
H11 H 0.6535 1.1382 0.5284 0.017 Uiso 1 1 calc R U . . .
C12 C 0.7550(2) 0.9092(2) 0.48548(8) 0.0116(4) Uani 1 1 d . . . . .
C13 C 0.7674(2) 0.7452(2) 0.48753(8) 0.0122(4) Uani 1 1 d . . . . .
C14 C 0.6808(2) 0.7054(2) 0.53705(8) 0.0114(4) Uani 1 1 d . . . . .
C15 C 1.0263(2) 0.8710(2) 0.33958(8) 0.0131(4) Uani 1 1 d . . . . .
C16 C 1.1510(3) 0.9260(2) 0.34720(8) 0.0154(4) Uani 1 1 d . . . . .
H16 H 1.1758 0.9329 0.3842 0.018 Uiso 1 1 calc R U . . .
C17 C 1.2408(3) 0.9713(2) 0.30171(8) 0.0159(4) Uani 1 1 d . . . . .
H17 H 1.3238 1.0124 0.3075 0.019 Uiso 1 1 calc R U . . .
C18 C 1.2076(2) 0.9557(2) 0.24771(8) 0.0147(4) Uani 1 1 d . . . . .
C19 C 1.0807(2) 0.9010(2) 0.24030(8) 0.0156(4) Uani 1 1 d . . . . .
H19 H 1.0577 0.8911 0.2033 0.019 Uiso 1 1 calc R U . . .
C20 C 0.9879(3) 0.8611(2) 0.28619(8) 0.0158(4) Uani 1 1 d . . . . .
H20 H 0.8987 0.8273 0.2811 0.019 Uiso 1 1 calc R U . . .
C21 C 1.4310(3) 1.0388(3) 0.20701(8) 0.0186(4) Uani 1 1 d . . . . .
H21A H 1.5191 0.9551 0.2287 0.022 Uiso 1 1 calc R U . . .
H21B H 1.3721 1.1516 0.2286 0.022 Uiso 1 1 calc R U . . .
C22 C 1.5289(3) 1.0485(3) 0.14970(8) 0.0193(4) Uani 1 1 d . . . . .
H22A H 1.4390 1.1241 0.1268 0.023 Uiso 1 1 calc R U . . .
H22B H 1.5962 0.9334 0.1295 0.023 Uiso 1 1 calc R U . . .
C23 C 1.6618(3) 1.1172(3) 0.15613(8) 0.0189(4) Uani 1 1 d . . . . .
H23A H 1.7423 1.0480 0.1825 0.023 Uiso 1 1 calc R U . . .
H23B H 1.5919 1.2358 0.1735 0.023 Uiso 1 1 calc R U . . .
C24 C 1.7798(3) 1.1156(3) 0.10033(8) 0.0202(4) Uani 1 1 d . . . . .
H24A H 1.8531 0.9967 0.0835 0.024 Uiso 1 1 calc R U . . .
H24B H 1.6998 1.1824 0.0735 0.024 Uiso 1 1 calc R U . . .
C25 C 1.9073(3) 1.1895(3) 0.10786(9) 0.0234(5) Uani 1 1 d . . . . .
H25A H 1.9872 1.1225 0.1347 0.028 Uiso 1 1 calc R U . . .
H25B H 1.8339 1.3082 0.1249 0.028 Uiso 1 1 calc R U . . .
C26 C 2.0257(3) 1.1891(3) 0.05242(10) 0.0319(5) Uani 1 1 d . . . . .
H26A H 2.0990 1.0720 0.0353 0.048 Uiso 1 1 calc R U . . .
H26B H 2.1066 1.2355 0.0600 0.048 Uiso 1 1 calc R U . . .
H26C H 1.9477 1.2596 0.0263 0.048 Uiso 1 1 calc R U . . .
C27 C 0.4070(2) 0.5884(2) 0.68367(8) 0.0131(4) Uani 1 1 d . . . . .
C28 C 0.5061(3) 0.4758(2) 0.72016(8) 0.0154(4) Uani 1 1 d . . . . .
H28 H 0.6347 0.4313 0.7148 0.018 Uiso 1 1 calc R U . . .
C29 C 0.4151(3) 0.4290(2) 0.76449(8) 0.0167(4) Uani 1 1 d . . . . .
H29 H 0.4813 0.3519 0.7900 0.020 Uiso 1 1 calc R U . . .
C30 C 0.2273(3) 0.4943(2) 0.77183(8) 0.0148(4) Uani 1 1 d . . . . .
C31 C 0.1289(3) 0.6104(2) 0.73607(8) 0.0174(4) Uani 1 1 d . . . . .
H31 H -0.0001 0.6577 0.7419 0.021 Uiso 1 1 calc R U . . .
C32 C 0.2209(3) 0.6572(2) 0.69151(8) 0.0165(4) Uani 1 1 d . . . . .
H32 H 0.1550 0.7368 0.6665 0.020 Uiso 1 1 calc R U . . .
C33 C -0.0396(3) 0.4933(3) 0.82481(9) 0.0194(4) Uani 1 1 d . . . . .
H33A H -0.0751 0.4696 0.7897 0.023 Uiso 1 1 calc R U . . .
H33B H -0.1055 0.6179 0.8348 0.023 Uiso 1 1 calc R U . . .
C34 C -0.0866(3) 0.4002(3) 0.87253(8) 0.0202(4) Uani 1 1 d . . . . .
H34A H -0.0639 0.4357 0.9083 0.024 Uiso 1 1 calc R U . . .
H34B H -0.0062 0.2760 0.8645 0.024 Uiso 1 1 calc R U . . .
C35 C -0.2840(3) 0.4358(3) 0.88009(9) 0.0194(4) Uani 1 1 d . . . . .
H35A H -0.3097 0.4126 0.8430 0.023 Uiso 1 1 calc R U . . .
H35B H -0.3638 0.5582 0.8920 0.023 Uiso 1 1 calc R U . . .
C36 C -0.3317(3) 0.3298(3) 0.92352(9) 0.0231(5) Uani 1 1 d . . . . .
H36A H -0.2508 0.2073 0.9119 0.028 Uiso 1 1 calc R U . . .
H36B H -0.3079 0.3542 0.9607 0.028 Uiso 1 1 calc R U . . .
C37 C -0.5281(3) 0.3640(3) 0.93026(9) 0.0276(5) Uani 1 1 d . . . . .
H37A H -0.5511 0.3372 0.8932 0.033 Uiso 1 1 calc R U . . .
H37B H -0.6090 0.4869 0.9411 0.033 Uiso 1 1 calc R U . . .
C38 C -0.5770(3) 0.2612(3) 0.97441(10) 0.0368(6) Uani 1 1 d . . . . .
H38A H -0.4962 0.1392 0.9645 0.055 Uiso 1 1 calc R U . . .
H38B H -0.7038 0.2852 0.9755 0.055 Uiso 1 1 calc R U . . .
H38C H -0.5628 0.2927 1.0117 0.055 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.217(2) . ?
O2 C2 1.208(2) . ?
O3 C7 1.217(2) . ?
O4 C8 1.207(2) . ?
O5 C18 1.366(2) . ?
O5 C21 1.438(2) . ?
O6 C30 1.375(2) . ?
O6 C33 1.424(2) . ?
N1 C1 1.394(2) . ?
N1 C2 1.410(2) . ?
N1 C15 1.449(2) . ?
N2 C7 1.390(2) . ?
N2 C8 1.398(2) . ?
N2 C27 1.456(2) . ?
C1 C12 1.480(3) . ?
C2 C3 1.483(3) . ?
C3 C4 1.376(3) . ?
C3 C13 1.406(3) . ?
C4 C5 1.406(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(3) . ?
C5 H5 0.9500 . ?
C6 C14 1.406(3) . ?
C6 C7 1.479(3) . ?
C8 C9 1.485(3) . ?
C9 C10 1.378(3) . ?
C9 C14 1.405(3) . ?
C10 C11 1.403(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.366(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.408(3) . ?
C13 C14 1.417(3) . ?
C15 C16 1.377(3) . ?
C15 C20 1.381(3) . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(3) . ?
C19 C20 1.382(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.504(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.523(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.525(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.521(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.523(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C32 1.370(3) . ?
C27 C28 1.380(3) . ?
C28 C29 1.379(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.387(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.380(3) . ?
C31 C32 1.388(3) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.510(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.517(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.522(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.514(3) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.517(3) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O5 C21 116.31(14) . . ?
C30 O6 C33 117.53(15) . . ?
C1 N1 C2 124.70(16) . . ?
C1 N1 C15 117.20(15) . . ?
C2 N1 C15 117.88(15) . . ?
C7 N2 C8 125.29(15) . . ?
C7 N2 C27 116.81(15) . . ?
C8 N2 C27 117.88(15) . . ?
O1 C1 N1 121.03(17) . . ?
O1 C1 C12 121.64(17) . . ?
N1 C1 C12 117.33(16) . . ?
O2 C2 N1 120.88(17) . . ?
O2 C2 C3 122.73(17) . . ?
N1 C2 C3 116.39(16) . . ?
C4 C3 C13 119.94(17) . . ?
C4 C3 C2 120.19(17) . . ?
C13 C3 C2 119.85(17) . . ?
C3 C4 C5 120.33(18) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.62(18) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C14 120.09(17) . . ?
C5 C6 C7 120.45(17) . . ?
C14 C6 C7 119.45(17) . . ?
O3 C7 N2 120.75(17) . . ?
O3 C7 C6 121.95(18) . . ?
N2 C7 C6 117.30(16) . . ?
O4 C8 N2 121.33(17) . . ?
O4 C8 C9 122.47(17) . . ?
N2 C8 C9 116.20(16) . . ?
C10 C9 C14 120.27(17) . . ?
C10 C9 C8 119.62(17) . . ?
C14 C9 C8 120.10(17) . . ?
C9 C10 C11 120.00(17) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.69(17) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.58(17) . . ?
C11 C12 C1 119.80(17) . . ?
C13 C12 C1 119.53(17) . . ?
C3 C13 C12 121.42(17) . . ?
C3 C13 C14 119.70(17) . . ?
C12 C13 C14 118.88(17) . . ?
C9 C14 C6 121.29(17) . . ?
C9 C14 C13 119.51(17) . . ?
C6 C14 C13 119.19(17) . . ?
C16 C15 C20 120.26(17) . . ?
C16 C15 N1 118.44(16) . . ?
C20 C15 N1 121.28(17) . . ?
C15 C16 C17 120.95(18) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C18 119.02(18) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
O5 C18 C17 123.96(17) . . ?
O5 C18 C19 116.27(17) . . ?
C17 C18 C19 119.76(17) . . ?
C20 C19 C18 120.74(18) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C15 C20 C19 119.20(18) . . ?
C15 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
O5 C21 C22 109.22(16) . . ?
O5 C21 H21A 109.8 . . ?
C22 C21 H21A 109.8 . . ?
O5 C21 H21B 109.8 . . ?
C22 C21 H21B 109.8 . . ?
H21A C21 H21B 108.3 . . ?
C21 C22 C23 110.40(17) . . ?
C21 C22 H22A 109.6 . . ?
C23 C22 H22A 109.6 . . ?
C21 C22 H22B 109.6 . . ?
C23 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
C22 C23 C24 113.86(17) . . ?
C22 C23 H23A 108.8 . . ?
C24 C23 H23A 108.8 . . ?
C22 C23 H23B 108.8 . . ?
C24 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C25 C24 C23 112.65(17) . . ?
C25 C24 H24A 109.1 . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24B 109.1 . . ?
C23 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
C24 C25 C26 113.21(18) . . ?
C24 C25 H25A 108.9 . . ?
C26 C25 H25A 108.9 . . ?
C24 C25 H25B 108.9 . . ?
C26 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
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 . . ?
C32 C27 C28 121.39(17) . . ?
C32 C27 N2 119.29(16) . . ?
C28 C27 N2 119.25(16) . . ?
C29 C28 C27 118.87(18) . . ?
C29 C28 H28 120.6 . . ?
C27 C28 H28 120.6 . . ?
C28 C29 C30 120.14(18) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
O6 C30 C31 124.43(17) . . ?
O6 C30 C29 115.04(16) . . ?
C31 C30 C29 120.53(17) . . ?
C30 C31 C32 119.13(18) . . ?
C30 C31 H31 120.4 . . ?
C32 C31 H31 120.4 . . ?
C27 C32 C31 119.89(18) . . ?
C27 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
O6 C33 C34 107.62(16) . . ?
O6 C33 H33A 110.2 . . ?
C34 C33 H33A 110.2 . . ?
O6 C33 H33B 110.2 . . ?
C34 C33 H33B 110.2 . . ?
H33A C33 H33B 108.5 . . ?
C33 C34 C35 111.99(16) . . ?
C33 C34 H34A 109.2 . . ?
C35 C34 H34A 109.2 . . ?
C33 C34 H34B 109.2 . . ?
C35 C34 H34B 109.2 . . ?
H34A C34 H34B 107.9 . . ?
C34 C35 C36 113.60(17) . . ?
C34 C35 H35A 108.8 . . ?
C36 C35 H35A 108.8 . . ?
C34 C35 H35B 108.8 . . ?
C36 C35 H35B 108.8 . . ?
H35A C35 H35B 107.7 . . ?
C37 C36 C35 113.37(17) . . ?
C37 C36 H36A 108.9 . . ?
C35 C36 H36A 108.9 . . ?
C37 C36 H36B 108.9 . . ?
C35 C36 H36B 108.9 . . ?
H36A C36 H36B 107.7 . . ?
C36 C37 C38 113.48(19) . . ?
C36 C37 H37A 108.9 . . ?
C38 C37 H37A 108.9 . . ?
C36 C37 H37B 108.9 . . ?
C38 C37 H37B 108.9 . . ?
H37A C37 H37B 107.7 . . ?
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 . . ?

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
C2 N1 C1 O1 -179.39(17) . . . . ?
C15 N1 C1 O1 6.1(2) . . . . ?
C2 N1 C1 C12 0.5(3) . . . . ?
C15 N1 C1 C12 -174.00(15) . . . . ?
C1 N1 C2 O2 -172.20(17) . . . . ?
C15 N1 C2 O2 2.2(3) . . . . ?
C1 N1 C2 C3 7.0(3) . . . . ?
C15 N1 C2 C3 -178.50(15) . . . . ?
O2 C2 C3 C4 -8.5(3) . . . . ?
N1 C2 C3 C4 172.27(16) . . . . ?
O2 C2 C3 C13 170.05(17) . . . . ?
N1 C2 C3 C13 -9.2(2) . . . . ?
C13 C3 C4 C5 0.8(3) . . . . ?
C2 C3 C4 C5 179.35(17) . . . . ?
C3 C4 C5 C6 -2.2(3) . . . . ?
C4 C5 C6 C14 0.4(3) . . . . ?
C4 C5 C6 C7 179.34(17) . . . . ?
C8 N2 C7 O3 -177.86(17) . . . . ?
C27 N2 C7 O3 0.8(2) . . . . ?
C8 N2 C7 C6 2.1(3) . . . . ?
C27 N2 C7 C6 -179.26(16) . . . . ?
C5 C6 C7 O3 -4.0(3) . . . . ?
C14 C6 C7 O3 174.96(17) . . . . ?
C5 C6 C7 N2 176.06(16) . . . . ?
C14 C6 C7 N2 -5.0(2) . . . . ?
C7 N2 C8 O4 -177.38(17) . . . . ?
C27 N2 C8 O4 4.0(3) . . . . ?
C7 N2 C8 C9 3.3(2) . . . . ?
C27 N2 C8 C9 -175.29(15) . . . . ?
O4 C8 C9 C10 -5.8(3) . . . . ?
N2 C8 C9 C10 173.45(16) . . . . ?
O4 C8 C9 C14 174.58(17) . . . . ?
N2 C8 C9 C14 -6.1(2) . . . . ?
C14 C9 C10 C11 -0.1(3) . . . . ?
C8 C9 C10 C11 -179.70(16) . . . . ?
C9 C10 C11 C12 -1.8(3) . . . . ?
C10 C11 C12 C13 1.4(3) . . . . ?
C10 C11 C12 C1 178.12(17) . . . . ?
O1 C1 C12 C11 -3.1(3) . . . . ?
N1 C1 C12 C11 177.00(16) . . . . ?
O1 C1 C12 C13 173.62(17) . . . . ?
N1 C1 C12 C13 -6.3(2) . . . . ?
C4 C3 C13 C12 -177.61(17) . . . . ?
C2 C3 C13 C12 3.8(3) . . . . ?
C4 C3 C13 C14 2.3(3) . . . . ?
C2 C3 C13 C14 -176.22(16) . . . . ?
C11 C12 C13 C3 -179.27(17) . . . . ?
C1 C12 C13 C3 4.0(3) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
C1 C12 C13 C14 -175.93(16) . . . . ?
C10 C9 C14 C6 -176.16(17) . . . . ?
C8 C9 C14 C6 3.4(3) . . . . ?
C10 C9 C14 C13 2.3(3) . . . . ?
C8 C9 C14 C13 -178.12(16) . . . . ?
C5 C6 C14 C9 -178.83(17) . . . . ?
C7 C6 C14 C9 2.2(3) . . . . ?
C5 C6 C14 C13 2.7(3) . . . . ?
C7 C6 C14 C13 -176.22(16) . . . . ?
C3 C13 C14 C9 177.44(16) . . . . ?
C12 C13 C14 C9 -2.6(3) . . . . ?
C3 C13 C14 C6 -4.1(3) . . . . ?
C12 C13 C14 C6 175.86(16) . . . . ?
C1 N1 C15 C16 58.0(2) . . . . ?
C2 N1 C15 C16 -116.92(19) . . . . ?
C1 N1 C15 C20 -120.4(2) . . . . ?
C2 N1 C15 C20 64.7(2) . . . . ?
C20 C15 C16 C17 -0.4(3) . . . . ?
N1 C15 C16 C17 -178.72(17) . . . . ?
C15 C16 C17 C18 -2.0(3) . . . . ?
C21 O5 C18 C17 0.8(3) . . . . ?
C21 O5 C18 C19 -177.95(16) . . . . ?
C16 C17 C18 O5 -176.41(18) . . . . ?
C16 C17 C18 C19 2.3(3) . . . . ?
O5 C18 C19 C20 178.44(16) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C16 C15 C20 C19 2.3(3) . . . . ?
N1 C15 C20 C19 -179.38(17) . . . . ?
C18 C19 C20 C15 -2.0(3) . . . . ?
C18 O5 C21 C22 173.27(16) . . . . ?
O5 C21 C22 C23 175.01(16) . . . . ?
C21 C22 C23 C24 174.61(17) . . . . ?
C22 C23 C24 C25 178.40(17) . . . . ?
C23 C24 C25 C26 -179.85(18) . . . . ?
C7 N2 C27 C32 -99.1(2) . . . . ?
C8 N2 C27 C32 79.7(2) . . . . ?
C7 N2 C27 C28 78.0(2) . . . . ?
C8 N2 C27 C28 -103.2(2) . . . . ?
C32 C27 C28 C29 1.7(3) . . . . ?
N2 C27 C28 C29 -175.33(17) . . . . ?
C27 C28 C29 C30 0.2(3) . . . . ?
C33 O6 C30 C31 1.8(3) . . . . ?
C33 O6 C30 C29 -178.20(17) . . . . ?
C28 C29 C30 O6 177.96(17) . . . . ?
C28 C29 C30 C31 -2.0(3) . . . . ?
O6 C30 C31 C32 -177.99(18) . . . . ?
C29 C30 C31 C32 2.0(3) . . . . ?
C28 C27 C32 C31 -1.7(3) . . . . ?
N2 C27 C32 C31 175.30(17) . . . . ?
C30 C31 C32 C27 -0.1(3) . . . . ?
C30 O6 C33 C34 175.62(16) . . . . ?
O6 C33 C34 C35 -172.45(16) . . . . ?
C33 C34 C35 C36 173.86(17) . . . . ?
C34 C35 C36 C37 -179.15(18) . . . . ?
C35 C36 C37 C38 -178.80(19) . . . . ?

_refine_diff_density_max         0.396
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_scd1656_HeptNDI_T100K
_database_code_depnum_ccdc_archive 'CCDC 1839985'
#Added by publCIF



_audit_update_record             
;
2018-04-27 deposited with the CCDC.
2018-08-03 downloaded from the CCDC.
;
_publcif_datablock.id            {c96919a8-8b91-4bb5-a801-6e3b8c53dfd0}

_diffrn_radiation_monochromator  'HELIOS optics'
#Added by publCIF




_symmetry_space_group_name_hall  '-P 2yn'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H42 N2 O6'
_chemical_formula_sum            'C40 H42 N2 O6'
_chemical_formula_weight         646.75

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                   4.1696(15)
_cell_length_b                   46.595(14)
_cell_length_c                   8.214(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.529(10)
_cell_angle_gamma                90
_cell_volume                     1592.7(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.39

_exptl_crystal_description       fragment
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6988
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS (Krause, Herbst-Irmer, Sheldrick, & Stalke;  J. Appl. Cryst. 2015, 48,
3-10)
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS microfocus tube'
_diffrn_measurement_device_type  
;
Bruker Kappa D8 Quest CMOS diffractometer (with an Oxford Cryosystems cryostream
cooler)
;

_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40965
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -60
_diffrn_reflns_limit_k_max       60
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.523
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3672
_reflns_number_gt                2906
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL Intrinsic Phasing (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0407P)²+0.9641P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0042(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3672
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_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 0.0349(4) 0.56436(3) 0.11501(17) 0.0126(3) Uani 1 1 d . . . . .
C2 C 0.3771(4) 0.53162(3) 0.28943(17) 0.0128(3) Uani 1 1 d . . . . .
C3 C 0.2662(3) 0.50700(3) 0.18591(17) 0.0123(3) Uani 1 1 d . . . . .
C4 C 0.0509(3) 0.51176(3) 0.04969(17) 0.0115(3) Uani 1 1 d . . . . .
C5 C 0.3747(4) 0.47974(3) 0.22360(18) 0.0141(3) Uani 1 1 d . . . . .
H5 H 0.5199 0.4767 0.3157 0.017 Uiso 1 1 calc R U . . .
C6 C 0.2704(4) 0.45628(3) 0.12561(18) 0.0137(3) Uani 1 1 d . . . . .
H6 H 0.3435 0.4375 0.1529 0.016 Uiso 1 1 calc R U . . .
C7 C 0.0630(3) 0.46047(3) -0.00947(17) 0.0121(3) Uani 1 1 d . . . . .
C8 C 0.2828(3) 0.58063(3) 0.37886(17) 0.0129(3) Uani 1 1 d . . . . .
C9 C 0.1593(4) 0.57672(3) 0.52948(18) 0.0141(3) Uani 1 1 d . . . . .
H9 H 0.0344 0.5602 0.5492 0.017 Uiso 1 1 calc R U . . .
C10 C 0.2171(4) 0.59696(3) 0.65263(18) 0.0136(3) Uani 1 1 d . . . . .
H10 H 0.1334 0.5943 0.7565 0.016 Uiso 1 1 calc R U . . .
C11 C 0.3988(3) 0.62122(3) 0.62176(18) 0.0129(3) Uani 1 1 d . . . . .
C12 C 0.5146(4) 0.62532(3) 0.46769(18) 0.0153(3) Uani 1 1 d . . . . .
H12 H 0.6331 0.6422 0.4459 0.018 Uiso 1 1 calc R U . . .
C13 C 0.4580(4) 0.60508(3) 0.34672(18) 0.0146(3) Uani 1 1 d . . . . .
H13 H 0.5385 0.6079 0.2422 0.017 Uiso 1 1 calc R U . . .
C14 C 0.3444(4) 0.63950(3) 0.89097(18) 0.0150(3) Uani 1 1 d . . . . .
H14A H 0.4158 0.6214 0.9447 0.018 Uiso 1 1 calc R U . . .
H14B H 0.1069 0.6394 0.8775 0.018 Uiso 1 1 calc R U . . .
C15 C 0.4585(4) 0.66498(3) 0.99392(18) 0.0156(3) Uani 1 1 d . . . . .
H15A H 0.6943 0.6636 1.0155 0.019 Uiso 1 1 calc R U . . .
H15B H 0.3591 0.6641 1.1002 0.019 Uiso 1 1 calc R U . . .
C16 C 0.3777(4) 0.69384(3) 0.91411(18) 0.0153(3) Uani 1 1 d . . . . .
H16A H 0.1430 0.6948 0.8878 0.018 Uiso 1 1 calc R U . . .
H16B H 0.4855 0.6951 0.8103 0.018 Uiso 1 1 calc R U . . .
C17 C 0.4790(4) 0.71947(3) 1.02114(18) 0.0161(3) Uani 1 1 d . . . . .
H17A H 0.3649 0.7186 1.1232 0.019 Uiso 1 1 calc R U . . .
H17B H 0.7122 0.7181 1.0508 0.019 Uiso 1 1 calc R U . . .
C18 C 0.4090(4) 0.74836(3) 0.93884(19) 0.0164(3) Uani 1 1 d . . . . .
H18A H 0.5200 0.7491 0.8358 0.020 Uiso 1 1 calc R U . . .
H18B H 0.1753 0.7499 0.9109 0.020 Uiso 1 1 calc R U . . .
C19 C 0.5153(4) 0.77393(3) 1.04459(19) 0.0177(3) Uani 1 1 d . . . . .
H19A H 0.4063 0.7730 1.1482 0.021 Uiso 1 1 calc R U . . .
H19B H 0.7495 0.7725 1.0714 0.021 Uiso 1 1 calc R U . . .
C20 C 0.4418(4) 0.80273(3) 0.9631(2) 0.0246(4) Uani 1 1 d . . . . .
H20A H 0.5479 0.8037 0.8600 0.037 Uiso 1 1 calc R U . . .
H20B H 0.5212 0.8183 1.0352 0.037 Uiso 1 1 calc R U . . .
H20C H 0.2091 0.8047 0.9414 0.037 Uiso 1 1 calc R U . . .
N1 N 0.2277(3) 0.55823(3) 0.25692(15) 0.0129(3) Uani 1 1 d . . . . .
O1 O -0.0503(3) 0.58868(2) 0.08157(13) 0.0161(2) Uani 1 1 d . . . . .
O2 O 0.5864(3) 0.52912(2) 0.39802(13) 0.0170(2) Uani 1 1 d . . . . .
O3 O 0.4791(3) 0.64199(2) 0.73467(12) 0.0156(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2139(18) . ?
C1 N1 1.4041(19) . ?
C1 C7 1.488(2) 3_565 ?
C2 O2 1.2144(18) . ?
C2 N1 1.4055(19) . ?
C2 C3 1.485(2) . ?
C3 C5 1.377(2) . ?
C3 C4 1.408(2) . ?
C4 C7 1.410(2) 3_565 ?
C4 C4 1.416(3) 3_565 ?
C5 C6 1.410(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(2) . ?
C6 H6 0.9500 . ?
C7 C4 1.410(2) 3_565 ?
C7 C1 1.488(2) 3_565 ?
C8 C9 1.381(2) . ?
C8 C13 1.387(2) . ?
C8 N1 1.4551(18) . ?
C9 C10 1.393(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(2) . ?
C10 H10 0.9500 . ?
C11 O3 1.3679(17) . ?
C11 C12 1.395(2) . ?
C12 C13 1.380(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O3 1.4372(18) . ?
C14 C15 1.517(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.524(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.527(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.526(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.524(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.522(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 121.51(13) . . ?
O1 C1 C7 121.89(14) . 3_565 ?
N1 C1 C7 116.60(13) . 3_565 ?
O2 C2 N1 120.94(13) . . ?
O2 C2 C3 122.06(14) . . ?
N1 C2 C3 117.00(13) . . ?
C5 C3 C4 120.57(13) . . ?
C5 C3 C2 119.84(13) . . ?
C4 C3 C2 119.60(13) . . ?
C3 C4 C7 121.32(13) . 3_565 ?
C3 C4 C4 119.32(17) . 3_565 ?
C7 C4 C4 119.36(17) 3_565 3_565 ?
C3 C5 C6 120.07(14) . . ?
C3 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 120.40(14) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C4 120.27(13) . 3_565 ?
C6 C7 C1 119.68(13) . 3_565 ?
C4 C7 C1 120.04(13) 3_565 3_565 ?
C9 C8 C13 120.57(13) . . ?
C9 C8 N1 118.05(13) . . ?
C13 C8 N1 121.38(13) . . ?
C8 C9 C10 120.25(14) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 119.28(13) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
O3 C11 C10 124.34(13) . . ?
O3 C11 C12 115.72(13) . . ?
C10 C11 C12 119.93(13) . . ?
C13 C12 C11 120.40(14) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C8 119.54(14) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
O3 C14 C15 107.95(12) . . ?
O3 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
O3 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
C14 C15 C16 113.40(12) . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 113.34(13) . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 113.34(13) . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 113.33(13) . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C18 113.25(13) . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 C2 124.18(12) . . ?
C1 N1 C8 118.90(12) . . ?
C2 N1 C8 116.91(12) . . ?
C11 O3 C14 117.10(12) . . ?

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
O2 C2 C3 C5 7.5(2) . . . . ?
N1 C2 C3 C5 -172.28(13) . . . . ?
O2 C2 C3 C4 -172.46(13) . . . . ?
N1 C2 C3 C4 7.8(2) . . . . ?
C5 C3 C4 C7 179.90(13) . . . 3_565 ?
C2 C3 C4 C7 -0.2(2) . . . 3_565 ?
C5 C3 C4 C4 -0.7(2) . . . 3_565 ?
C2 C3 C4 C4 179.23(15) . . . 3_565 ?
C4 C3 C5 C6 0.0(2) . . . . ?
C2 C3 C5 C6 -179.93(13) . . . . ?
C3 C5 C6 C7 0.8(2) . . . . ?
C5 C6 C7 C4 -1.0(2) . . . 3_565 ?
C5 C6 C7 C1 177.71(13) . . . 3_565 ?
C13 C8 C9 C10 -1.8(2) . . . . ?
N1 C8 C9 C10 177.26(13) . . . . ?
C8 C9 C10 C11 0.4(2) . . . . ?
C9 C10 C11 O3 -177.83(14) . . . . ?
C9 C10 C11 C12 1.4(2) . . . . ?
O3 C11 C12 C13 177.45(14) . . . . ?
C10 C11 C12 C13 -1.9(2) . . . . ?
C11 C12 C13 C8 0.5(2) . . . . ?
C9 C8 C13 C12 1.4(2) . . . . ?
N1 C8 C13 C12 -177.67(14) . . . . ?
O3 C14 C15 C16 55.89(17) . . . . ?
C14 C15 C16 C17 177.37(13) . . . . ?
C15 C16 C17 C18 177.91(13) . . . . ?
C16 C17 C18 C19 -179.03(13) . . . . ?
C17 C18 C19 C20 -179.33(14) . . . . ?
O1 C1 N1 C2 -169.17(14) . . . . ?
C7 C1 N1 C2 11.7(2) 3_565 . . . ?
O1 C1 N1 C8 10.1(2) . . . . ?
C7 C1 N1 C8 -169.09(12) 3_565 . . . ?
O2 C2 N1 C1 166.27(14) . . . . ?
C3 C2 N1 C1 -14.0(2) . . . . ?
O2 C2 N1 C8 -13.0(2) . . . . ?
C3 C2 N1 C8 166.76(12) . . . . ?
C9 C8 N1 C1 114.22(15) . . . . ?
C13 C8 N1 C1 -66.70(19) . . . . ?
C9 C8 N1 C2 -66.49(18) . . . . ?
C13 C8 N1 C2 112.58(16) . . . . ?
C10 C11 O3 C14 -5.1(2) . . . . ?
C12 C11 O3 C14 175.61(13) . . . . ?
C15 C14 O3 C11 -178.63(12) . . . . ?

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_scd1706_OctNDI_T100K_orange
_database_code_depnum_ccdc_archive 'CCDC 1839986'
#Added by publCIF



_audit_update_record             
;
2018-04-27 deposited with the CCDC.
2018-08-03 downloaded from the CCDC.
;
_publcif_datablock.id            {2925dfd5-97bb-4a9f-bdcc-729ec34e9730}

_diffrn_radiation_monochromator  'HELIOS optics'
#Added by publCIF




_symmetry_space_group_name_hall  '-P 1'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H46 N2 O6'
_chemical_formula_sum            'C42 H46 N2 O6'
_chemical_formula_weight         674.81

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                   4.1680(14)
_cell_length_b                   8.217(3)
_cell_length_c                   24.901(7)
_cell_angle_alpha                97.810(10)
_cell_angle_beta                 93.453(7)
_cell_angle_gamma                93.834(6)
_cell_volume                     841.0(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7013
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.43

_exptl_crystal_description       fragment
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5942
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS (Krause, Herbst-Irmer, Sheldrick, & Stalke;  J. Appl. Cryst. 2015, 48,
3-10)
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS microfocus tube'
_diffrn_measurement_device_type  
;
Bruker Kappa D8 Quest CMOS diffractometer (with an Oxford Cryosystems cryostream
cooler)
;

_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25306
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.483
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3887
_reflns_number_gt                2622
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL Intrinsic Phasing (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0456P)²+0.4048P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3887
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1199
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
N1 N 0.3172(3) 0.79069(17) 0.11031(6) 0.0131(3) Uani 1 1 d . . . . .
O1 O -0.0659(3) 0.62524(15) 0.05532(5) 0.0171(3) Uani 1 1 d . . . . .
O2 O 0.6173(3) 0.99164(15) 0.16805(5) 0.0169(3) Uani 1 1 d . . . . .
O3 O 0.1250(3) 0.38285(15) 0.26956(5) 0.0164(3) Uani 1 1 d . . . . .
C1 C 0.1463(4) 0.7358(2) 0.06004(7) 0.0134(4) Uani 1 1 d . . . . .
C2 C 0.5139(4) 0.9376(2) 0.12191(7) 0.0136(4) Uani 1 1 d . . . . .
C3 C 0.5931(4) 1.0235(2) 0.07493(7) 0.0126(4) Uani 1 1 d . . . . .
C4 C 0.8042(4) 1.1622(2) 0.08281(7) 0.0141(4) Uani 1 1 d . . . . .
H4 H 0.8919 1.2053 0.1184 0.017 Uiso 1 1 calc R U . . .
C5 C 0.8905(4) 1.2401(2) 0.03824(7) 0.0138(4) Uani 1 1 d . . . . .
H5 H 1.0390 1.3347 0.0439 0.017 Uiso 1 1 calc R U . . .
C6 C 0.7617(4) 1.1807(2) -0.01327(7) 0.0128(4) Uani 1 1 d . . . . .
C7 C 0.5411(4) 1.0397(2) -0.02233(7) 0.0124(4) Uani 1 1 d . . . . .
C8 C 0.2780(4) 0.6867(2) 0.15280(7) 0.0132(4) Uani 1 1 d . . . . .
C9 C 0.3962(4) 0.5333(2) 0.14582(7) 0.0140(4) Uani 1 1 d . . . . .
H9 H 0.5078 0.4997 0.1145 0.017 Uiso 1 1 calc R U . . .
C10 C 0.3537(4) 0.4271(2) 0.18422(7) 0.0137(4) Uani 1 1 d . . . . .
H10 H 0.4343 0.3210 0.1793 0.016 Uiso 1 1 calc R U . . .
C11 C 0.1913(4) 0.4784(2) 0.23006(7) 0.0132(4) Uani 1 1 d . . . . .
C12 C 0.0822(4) 0.6355(2) 0.23752(7) 0.0151(4) Uani 1 1 d . . . . .
H12 H -0.0218 0.6716 0.2695 0.018 Uiso 1 1 calc R U . . .
C13 C 0.1232(4) 0.7396(2) 0.19900(7) 0.0148(4) Uani 1 1 d . . . . .
H13 H 0.0462 0.8464 0.2041 0.018 Uiso 1 1 calc R U . . .
C14 C 0.2562(4) 0.2248(2) 0.26557(7) 0.0154(4) Uani 1 1 d . . . . .
H14A H 0.4937 0.2379 0.2650 0.019 Uiso 1 1 calc R U . . .
H14B H 0.1684 0.1547 0.2317 0.019 Uiso 1 1 calc R U . . .
C15 C 0.1629(4) 0.1457(2) 0.31469(7) 0.0158(4) Uani 1 1 d . . . . .
H15A H 0.2601 0.0388 0.3136 0.019 Uiso 1 1 calc R U . . .
H15B H -0.0742 0.1235 0.3126 0.019 Uiso 1 1 calc R U . . .
C16 C 0.2705(4) 0.2521(2) 0.36849(7) 0.0162(4) Uani 1 1 d . . . . .
H16A H 0.1656 0.3571 0.3701 0.019 Uiso 1 1 calc R U . . .
H16B H 0.5063 0.2786 0.3697 0.019 Uiso 1 1 calc R U . . .
C17 C 0.1918(4) 0.1714(2) 0.41845(7) 0.0164(4) Uani 1 1 d . . . . .
H17A H -0.0433 0.1426 0.4171 0.020 Uiso 1 1 calc R U . . .
H17B H 0.3019 0.0681 0.4177 0.020 Uiso 1 1 calc R U . . .
C18 C 0.2956(4) 0.2835(2) 0.47132(7) 0.0170(4) Uani 1 1 d . . . . .
H18A H 0.1836 0.3862 0.4717 0.020 Uiso 1 1 calc R U . . .
H18B H 0.5297 0.3139 0.4718 0.020 Uiso 1 1 calc R U . . .
C19 C 0.2294(4) 0.2107(2) 0.52303(7) 0.0162(4) Uani 1 1 d . . . . .
H19A H -0.0052 0.1832 0.5236 0.019 Uiso 1 1 calc R U . . .
H19B H 0.3387 0.1074 0.5230 0.019 Uiso 1 1 calc R U . . .
C20 C 0.3462(5) 0.3291(2) 0.57398(7) 0.0194(4) Uani 1 1 d . . . . .
H20A H 0.5802 0.3572 0.5728 0.023 Uiso 1 1 calc R U . . .
H20B H 0.2361 0.4320 0.5737 0.023 Uiso 1 1 calc R U . . .
C21 C 0.2880(5) 0.2622(3) 0.62691(7) 0.0247(5) Uani 1 1 d . . . . .
H21A H 0.0557 0.2424 0.6299 0.037 Uiso 1 1 calc R U . . .
H21B H 0.3797 0.3425 0.6576 0.037 Uiso 1 1 calc R U . . .
H21C H 0.3912 0.1585 0.6273 0.037 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.399(2) . ?
N1 C1 1.405(2) . ?
N1 C8 1.457(2) . ?
O1 C1 1.213(2) . ?
O2 C2 1.216(2) . ?
O3 C11 1.369(2) . ?
O3 C14 1.436(2) . ?
C1 C6 1.487(2) 2_675 ?
C2 C3 1.489(2) . ?
C3 C4 1.377(2) . ?
C3 C7 1.409(2) 2_675 ?
C4 C5 1.408(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.372(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.414(2) . ?
C6 C1 1.487(2) 2_675 ?
C7 C3 1.409(2) 2_675 ?
C7 C7 1.412(3) 2_675 ?
C8 C9 1.377(2) . ?
C8 C13 1.386(2) . ?
C9 C10 1.391(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(2) . ?
C12 C13 1.380(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.520(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.522(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.529(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.522(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.524(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.523(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.522(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 124.41(14) . . ?
C2 N1 C8 119.04(14) . . ?
C1 N1 C8 116.54(14) . . ?
C11 O3 C14 117.41(13) . . ?
O1 C1 N1 121.23(15) . . ?
O1 C1 C6 121.92(16) . 2_675 ?
N1 C1 C6 116.84(15) . 2_675 ?
O2 C2 N1 121.62(16) . . ?
O2 C2 C3 121.65(16) . . ?
N1 C2 C3 116.72(15) . . ?
C4 C3 C7 120.19(16) . 2_675 ?
C4 C3 C2 119.83(16) . . ?
C7 C3 C2 119.96(16) 2_675 . ?
C3 C4 C5 120.12(16) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.55(16) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.40(16) . . ?
C5 C6 C1 120.13(16) . 2_675 ?
C7 C6 C1 119.47(16) . 2_675 ?
C3 C7 C7 119.8(2) 2_675 2_675 ?
C3 C7 C6 121.28(16) 2_675 . ?
C7 C7 C6 118.9(2) 2_675 . ?
C9 C8 C13 120.49(16) . . ?
C9 C8 N1 118.42(15) . . ?
C13 C8 N1 121.08(15) . . ?
C8 C9 C10 120.55(16) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 119.05(16) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
O3 C11 C12 115.81(15) . . ?
O3 C11 C10 124.33(16) . . ?
C12 C11 C10 119.86(16) . . ?
C13 C12 C11 120.65(16) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 119.33(16) . . ?
C12 C13 H13 120.3 . . ?
C8 C13 H13 120.3 . . ?
O3 C14 C15 107.73(14) . . ?
O3 C14 H14A 110.2 . . ?
C15 C14 H14A 110.2 . . ?
O3 C14 H14B 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 C16 113.15(15) . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 113.93(15) . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 112.24(15) . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 C19 115.35(15) . . ?
C17 C18 H18A 108.4 . . ?
C19 C18 H18A 108.4 . . ?
C17 C18 H18B 108.4 . . ?
C19 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
C20 C19 C18 112.03(15) . . ?
C20 C19 H19A 109.2 . . ?
C18 C19 H19A 109.2 . . ?
C20 C19 H19B 109.2 . . ?
C18 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C21 C20 C19 114.29(16) . . ?
C21 C20 H20A 108.7 . . ?
C19 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
C19 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
C2 N1 C1 O1 -165.81(16) . . . . ?
C8 N1 C1 O1 13.0(2) . . . . ?
C2 N1 C1 C6 14.3(2) . . . 2_675 ?
C8 N1 C1 C6 -166.91(14) . . . 2_675 ?
C1 N1 C2 O2 168.73(16) . . . . ?
C8 N1 C2 O2 -10.1(2) . . . . ?
C1 N1 C2 C3 -11.9(2) . . . . ?
C8 N1 C2 C3 169.32(14) . . . . ?
O2 C2 C3 C4 4.1(3) . . . . ?
N1 C2 C3 C4 -175.27(15) . . . . ?
O2 C2 C3 C7 -177.63(16) . . . 2_675 ?
N1 C2 C3 C7 3.0(2) . . . 2_675 ?
C7 C3 C4 C5 -0.9(3) 2_675 . . . ?
C2 C3 C4 C5 177.38(15) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C4 C5 C6 C1 179.83(15) . . . 2_675 ?
C5 C6 C7 C3 -179.82(16) . . . 2_675 ?
C1 C6 C7 C3 0.2(2) 2_675 . . 2_675 ?
C5 C6 C7 C7 -0.8(3) . . . 2_675 ?
C1 C6 C7 C7 179.20(18) 2_675 . . 2_675 ?
C2 N1 C8 C9 -114.55(18) . . . . ?
C1 N1 C8 C9 66.5(2) . . . . ?
C2 N1 C8 C13 66.0(2) . . . . ?
C1 N1 C8 C13 -112.93(18) . . . . ?
C13 C8 C9 C10 2.0(3) . . . . ?
N1 C8 C9 C10 -177.52(15) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C14 O3 C11 C12 -175.11(15) . . . . ?
C14 O3 C11 C10 5.6(2) . . . . ?
C9 C10 C11 O3 177.60(16) . . . . ?
C9 C10 C11 C12 -1.7(2) . . . . ?
O3 C11 C12 C13 -177.13(16) . . . . ?
C10 C11 C12 C13 2.2(3) . . . . ?
C11 C12 C13 C8 -0.7(3) . . . . ?
C9 C8 C13 C12 -1.4(3) . . . . ?
N1 C8 C13 C12 178.02(16) . . . . ?
C11 O3 C14 C15 177.64(14) . . . . ?
O3 C14 C15 C16 -55.96(19) . . . . ?
C14 C15 C16 C17 -177.47(15) . . . . ?
C15 C16 C17 C18 -178.53(15) . . . . ?
C16 C17 C18 C19 -179.18(15) . . . . ?
C17 C18 C19 C20 178.84(16) . . . . ?
C18 C19 C20 C21 -179.64(16) . . . . ?

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_scd1613_NonNDI_T100K_orange
_database_code_depnum_ccdc_archive 'CCDC 1839987'
#Added by publCIF



_audit_update_record             
;
2018-04-27 deposited with the CCDC.
2018-08-03 downloaded from the CCDC.
;
_publcif_datablock.id            {bd220014-04c7-4a39-95fb-63a99dfcf3f8}

_diffrn_radiation_monochromator  'HELIOS optics'
#Added by publCIF




_symmetry_space_group_name_hall  '-P 2yn'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H50 N2 O6'
_chemical_formula_sum            'C44 H50 N2 O6'
_chemical_formula_weight         702.86

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                   4.154(2)
_cell_length_b                   51.72(2)
_cell_length_c                   8.253(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.663(12)
_cell_angle_gamma                90
_cell_volume                     1769.6(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8467
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.21

_exptl_crystal_description       fragment
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6533
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS (Krause, Herbst-Irmer, Sheldrick, & Stalke;  J. Appl. Cryst. 2015, 48,
3-10)
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS microfocus tube'
_diffrn_measurement_device_type  
;
Bruker Kappa D8 Quest CMOS diffractometer (with an Oxford Cryosystems cryostream
cooler)
;

_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36862
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_av_R_equivalents  0.0947
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -67
_diffrn_reflns_limit_k_max       67
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.595
_diffrn_reflns_theta_max         27.514
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4080
_reflns_number_gt                2862
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL Intrinsic Phasing (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0427P)²+1.0464P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4080
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_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 0.0369(5) 0.44197(3) 0.1146(2) 0.0132(4) Uani 1 1 d . . . . .
C2 C 0.3758(4) 0.47162(3) 0.2892(2) 0.0137(4) Uani 1 1 d . . . . .
C3 C 0.2655(4) 0.49376(3) 0.1857(2) 0.0118(4) Uani 1 1 d . . . . .
C4 C 0.0507(4) 0.48934(3) 0.0497(2) 0.0117(4) Uani 1 1 d . . . . .
C5 C 0.3718(4) 0.51835(3) 0.2239(2) 0.0133(4) Uani 1 1 d . . . . .
H5 H 0.5158 0.5211 0.3164 0.016 Uiso 1 1 calc R U . . .
C6 C 0.2676(4) 0.53946(4) 0.1264(2) 0.0136(4) Uani 1 1 d . . . . .
H6 H 0.3400 0.5564 0.1541 0.016 Uiso 1 1 calc R U . . .
C7 C 0.0605(4) 0.53567(3) -0.0093(2) 0.0123(4) Uani 1 1 d . . . . .
C8 C 0.2845(4) 0.42735(3) 0.3774(2) 0.0127(4) Uani 1 1 d . . . . .
C9 C 0.1621(5) 0.43085(4) 0.5279(2) 0.0141(4) Uani 1 1 d . . . . .
H9 H 0.0368 0.4457 0.5480 0.017 Uiso 1 1 calc R U . . .
C10 C 0.2224(4) 0.41253(3) 0.6501(2) 0.0134(4) Uani 1 1 d . . . . .
H10 H 0.1403 0.4150 0.7539 0.016 Uiso 1 1 calc R U . . .
C11 C 0.4033(4) 0.39075(3) 0.6190(2) 0.0133(4) Uani 1 1 d . . . . .
C12 C 0.5174(5) 0.38705(4) 0.4649(2) 0.0152(4) Uani 1 1 d . . . . .
H12 H 0.6357 0.3719 0.4428 0.018 Uiso 1 1 calc R U . . .
C13 C 0.4591(5) 0.40532(3) 0.3451(2) 0.0148(4) Uani 1 1 d . . . . .
H13 H 0.5382 0.4028 0.2408 0.018 Uiso 1 1 calc R U . . .
C14 C 0.3518(5) 0.37389(3) 0.8867(2) 0.0149(4) Uani 1 1 d . . . . .
H14A H 0.1133 0.3743 0.8735 0.018 Uiso 1 1 calc R U . . .
H14B H 0.4266 0.3900 0.9422 0.018 Uiso 1 1 calc R U . . .
C15 C 0.4638(5) 0.35046(3) 0.9859(2) 0.0153(4) Uani 1 1 d . . . . .
H15A H 0.3637 0.3509 1.0915 0.018 Uiso 1 1 calc R U . . .
H15B H 0.7005 0.3515 1.0080 0.018 Uiso 1 1 calc R U . . .
C16 C 0.3806(5) 0.32484(3) 0.9024(2) 0.0157(4) Uani 1 1 d . . . . .
H16A H 0.4884 0.3241 0.7989 0.019 Uiso 1 1 calc R U . . .
H16B H 0.1450 0.3242 0.8759 0.019 Uiso 1 1 calc R U . . .
C17 C 0.4794(5) 0.30109(3) 1.0039(2) 0.0163(4) Uani 1 1 d . . . . .
H17A H 0.7137 0.3020 1.0341 0.020 Uiso 1 1 calc R U . . .
H17B H 0.3646 0.3013 1.1053 0.020 Uiso 1 1 calc R U . . .
C18 C 0.4055(5) 0.27573(3) 0.9149(2) 0.0162(4) Uani 1 1 d . . . . .
H18A H 0.1711 0.2749 0.8851 0.019 Uiso 1 1 calc R U . . .
H18B H 0.5189 0.2757 0.8130 0.019 Uiso 1 1 calc R U . . .
C19 C 0.5028(5) 0.25161(3) 1.0122(2) 0.0155(4) Uani 1 1 d . . . . .
H19A H 0.7369 0.2524 1.0426 0.019 Uiso 1 1 calc R U . . .
H19B H 0.3879 0.2515 1.1137 0.019 Uiso 1 1 calc R U . . .
C20 C 0.4290(5) 0.22652(3) 0.9205(2) 0.0163(4) Uani 1 1 d . . . . .
H20A H 0.1945 0.2256 0.8911 0.020 Uiso 1 1 calc R U . . .
H20B H 0.5421 0.2267 0.8185 0.020 Uiso 1 1 calc R U . . .
C21 C 0.5300(5) 0.20252(3) 1.0180(2) 0.0182(4) Uani 1 1 d . . . . .
H21A H 0.7648 0.2034 1.0467 0.022 Uiso 1 1 calc R U . . .
H21B H 0.4183 0.2025 1.1204 0.022 Uiso 1 1 calc R U . . .
C22 C 0.4558(5) 0.17726(4) 0.9286(3) 0.0248(5) Uani 1 1 d . . . . .
H22A H 0.2225 0.1758 0.9046 0.037 Uiso 1 1 calc R U . . .
H22B H 0.5318 0.1627 0.9968 0.037 Uiso 1 1 calc R U . . .
H22C H 0.5654 0.1771 0.8270 0.037 Uiso 1 1 calc R U . . .
N1 N 0.2278(4) 0.44757(3) 0.25619(17) 0.0125(3) Uani 1 1 d . . . . .
O1 O -0.0458(3) 0.42002(2) 0.08059(15) 0.0166(3) Uani 1 1 d . . . . .
O2 O 0.5858(3) 0.47391(2) 0.39785(15) 0.0174(3) Uani 1 1 d . . . . .
O3 O 0.4861(3) 0.37193(2) 0.73043(15) 0.0159(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.214(2) . ?
C1 N1 1.400(2) . ?
C1 C7 1.487(3) 3_565 ?
C2 O2 1.216(2) . ?
C2 N1 1.406(2) . ?
C2 C3 1.484(3) . ?
C3 C5 1.376(3) . ?
C3 C4 1.407(3) . ?
C4 C7 1.406(3) 3_565 ?
C4 C4 1.422(4) 3_565 ?
C5 C6 1.408(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(3) . ?
C6 H6 0.9500 . ?
C7 C4 1.406(3) 3_565 ?
C7 C1 1.487(3) 3_565 ?
C8 C9 1.384(3) . ?
C8 C13 1.386(3) . ?
C8 N1 1.456(2) . ?
C9 C10 1.395(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 O3 1.368(2) . ?
C11 C12 1.398(3) . ?
C12 C13 1.378(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O3 1.441(2) . ?
C14 C15 1.519(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.523(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.528(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.525(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.524(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.523(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.523(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.522(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 121.56(16) . . ?
O1 C1 C7 121.99(17) . 3_565 ?
N1 C1 C7 116.45(16) . 3_565 ?
O2 C2 N1 120.88(16) . . ?
O2 C2 C3 122.00(17) . . ?
N1 C2 C3 117.12(16) . . ?
C5 C3 C4 120.72(16) . . ?
C5 C3 C2 119.89(17) . . ?
C4 C3 C2 119.38(16) . . ?
C7 C4 C3 121.37(16) 3_565 . ?
C7 C4 C4 119.7(2) 3_565 3_565 ?
C3 C4 C4 118.9(2) . 3_565 ?
C3 C5 C6 120.20(17) . . ?
C3 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 120.39(17) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C4 120.06(16) . 3_565 ?
C6 C7 C1 119.67(17) . 3_565 ?
C4 C7 C1 120.25(17) 3_565 3_565 ?
C9 C8 C13 120.48(16) . . ?
C9 C8 N1 118.05(16) . . ?
C13 C8 N1 121.47(16) . . ?
C8 C9 C10 120.05(17) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 119.48(17) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
O3 C11 C10 124.69(16) . . ?
O3 C11 C12 115.41(16) . . ?
C10 C11 C12 119.90(16) . . ?
C13 C12 C11 120.30(17) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 119.74(17) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
O3 C14 C15 107.68(15) . . ?
O3 C14 H14A 110.2 . . ?
C15 C14 H14A 110.2 . . ?
O3 C14 H14B 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 C16 113.41(16) . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 113.96(16) . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 112.88(16) . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 C17 114.34(16) . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C18 113.42(16) . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 113.07(16) . . ?
C21 C20 H20A 109.0 . . ?
C19 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
C19 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C22 C21 C20 113.78(17) . . ?
C22 C21 H21A 108.8 . . ?
C20 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
C20 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 N1 C2 124.20(15) . . ?
C1 N1 C8 118.90(15) . . ?
C2 N1 C8 116.89(15) . . ?
C11 O3 C14 117.18(14) . . ?

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
O2 C2 C3 C5 -8.2(3) . . . . ?
N1 C2 C3 C5 172.11(16) . . . . ?
O2 C2 C3 C4 172.29(17) . . . . ?
N1 C2 C3 C4 -7.4(2) . . . . ?
C5 C3 C4 C7 -179.83(17) . . . 3_565 ?
C2 C3 C4 C7 -0.3(3) . . . 3_565 ?
C5 C3 C4 C4 1.1(3) . . . 3_565 ?
C2 C3 C4 C4 -179.36(19) . . . 3_565 ?
C4 C3 C5 C6 -0.4(3) . . . . ?
C2 C3 C5 C6 -179.85(16) . . . . ?
C3 C5 C6 C7 -0.6(3) . . . . ?
C5 C6 C7 C4 0.8(3) . . . 3_565 ?
C5 C6 C7 C1 -177.60(16) . . . 3_565 ?
C13 C8 C9 C10 2.0(3) . . . . ?
N1 C8 C9 C10 -177.21(17) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C9 C10 C11 O3 177.89(17) . . . . ?
C9 C10 C11 C12 -1.4(3) . . . . ?
O3 C11 C12 C13 -177.45(17) . . . . ?
C10 C11 C12 C13 1.9(3) . . . . ?
C11 C12 C13 C8 -0.4(3) . . . . ?
C9 C8 C13 C12 -1.5(3) . . . . ?
N1 C8 C13 C12 177.69(17) . . . . ?
O3 C14 C15 C16 -55.4(2) . . . . ?
C14 C15 C16 C17 -177.57(16) . . . . ?
C15 C16 C17 C18 -177.72(16) . . . . ?
C16 C17 C18 C19 179.66(16) . . . . ?
C17 C18 C19 C20 -179.56(16) . . . . ?
C18 C19 C20 C21 179.42(16) . . . . ?
C19 C20 C21 C22 179.57(17) . . . . ?
O1 C1 N1 C2 168.89(17) . . . . ?
C7 C1 N1 C2 -11.5(2) 3_565 . . . ?
O1 C1 N1 C8 -10.0(3) . . . . ?
C7 C1 N1 C8 169.57(15) 3_565 . . . ?
O2 C2 N1 C1 -165.90(17) . . . . ?
C3 C2 N1 C1 13.8(2) . . . . ?
O2 C2 N1 C8 13.0(2) . . . . ?
C3 C2 N1 C8 -167.31(15) . . . . ?
C9 C8 N1 C1 -115.10(19) . . . . ?
C13 C8 N1 C1 65.7(2) . . . . ?
C9 C8 N1 C2 65.9(2) . . . . ?
C13 C8 N1 C2 -113.3(2) . . . . ?
C10 C11 O3 C14 5.6(3) . . . . ?
C12 C11 O3 C14 -175.09(16) . . . . ?
C15 C14 O3 C11 177.38(15) . . . . ?

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.055

