# 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_scd1657_HeptNDI_T200K
_database_code_depnum_ccdc_archive 'CCDC 1857158'
#Added by publCIF



_audit_update_record             
;
2018-07-20 deposited with the CCDC.
2018-08-03 downloaded from the CCDC.
;
_publcif_datablock.id            {4c5d2717-74fb-4df3-8d6e-447faec5cf70}

_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                   4.2455(15)
_cell_length_b                   46.493(15)
_cell_length_c                   8.218(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.584(8)
_cell_angle_gamma                90
_cell_volume                     1619.0(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9993
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.31

_exptl_crystal_description       fragment
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_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    0.089
_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  0.6989
_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      200(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            40092
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0537
_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         2.522
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_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             3732
_reflns_number_gt                2856
_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)+(0.0435P)²+0.7091P] 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       0.0076(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3732
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.0244(4) 0.56423(3) 0.11935(18) 0.0217(3) Uani 1 1 d . . . . .
C2 C 0.3694(4) 0.53158(3) 0.29004(17) 0.0221(3) Uani 1 1 d . . . . .
C3 C 0.2636(3) 0.50699(3) 0.18511(17) 0.0205(3) Uani 1 1 d . . . . .
C4 C 0.0485(3) 0.51176(3) 0.05043(17) 0.0187(3) Uani 1 1 d . . . . .
C5 C 0.3747(4) 0.47976(3) 0.22018(18) 0.0242(3) Uani 1 1 d . . . . .
H5 H 0.5191 0.4767 0.3116 0.029 Uiso 1 1 calc R U . . .
C6 C 0.2754(4) 0.45642(3) 0.12126(18) 0.0232(3) Uani 1 1 d . . . . .
H6 H 0.3514 0.4376 0.1469 0.028 Uiso 1 1 calc R U . . .
C7 C 0.0689(4) 0.46055(3) -0.01256(17) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.2723(4) 0.58048(3) 0.38177(17) 0.0223(3) Uani 1 1 d . . . . .
C9 C 0.1485(4) 0.57662(3) 0.53163(18) 0.0244(3) Uani 1 1 d . . . . .
H9 H 0.0238 0.5601 0.5506 0.029 Uiso 1 1 calc R U . . .
C10 C 0.2058(4) 0.59677(3) 0.65477(18) 0.0238(3) Uani 1 1 d . . . . .
H10 H 0.1214 0.5941 0.7581 0.029 Uiso 1 1 calc R U . . .
C11 C 0.3873(4) 0.62083(3) 0.62563(18) 0.0221(3) Uani 1 1 d . . . . .
C12 C 0.5033(4) 0.62485(3) 0.47251(19) 0.0269(4) Uani 1 1 d . . . . .
H12 H 0.6218 0.6416 0.4515 0.032 Uiso 1 1 calc R U . . .
C13 C 0.4475(4) 0.60467(3) 0.35118(19) 0.0255(3) Uani 1 1 d . . . . .
H13 H 0.5291 0.6074 0.2472 0.031 Uiso 1 1 calc R U . . .
C14 C 0.3314(4) 0.63948(3) 0.89363(18) 0.0272(4) Uani 1 1 d . . . . .
H14A H 0.3980 0.6213 0.9484 0.033 Uiso 1 1 calc R U . . .
H14B H 0.0982 0.6396 0.8791 0.033 Uiso 1 1 calc R U . . .
C15 C 0.4459(4) 0.66503(3) 0.99568(19) 0.0282(4) Uani 1 1 d . . . . .
H15A H 0.6775 0.6636 1.0165 0.034 Uiso 1 1 calc R U . . .
H15B H 0.3497 0.6642 1.1023 0.034 Uiso 1 1 calc R U . . .
C16 C 0.3668(4) 0.69386(3) 0.91572(19) 0.0282(4) Uani 1 1 d . . . . .
H16A H 0.1360 0.6949 0.8904 0.034 Uiso 1 1 calc R U . . .
H16B H 0.4708 0.6950 0.8114 0.034 Uiso 1 1 calc R U . . .
C17 C 0.4689(4) 0.71965(3) 1.0210(2) 0.0294(4) Uani 1 1 d . . . . .
H17A H 0.3589 0.7189 1.1237 0.035 Uiso 1 1 calc R U . . .
H17B H 0.6983 0.7182 1.0497 0.035 Uiso 1 1 calc R U . . .
C18 C 0.4000(4) 0.74844(3) 0.9386(2) 0.0299(4) Uani 1 1 d . . . . .
H18A H 0.1702 0.7499 0.9112 0.036 Uiso 1 1 calc R U . . .
H18B H 0.5077 0.7491 0.8353 0.036 Uiso 1 1 calc R U . . .
C19 C 0.5052(4) 0.77420(3) 1.0427(2) 0.0331(4) Uani 1 1 d . . . . .
H19A H 0.3981 0.7735 1.1463 0.040 Uiso 1 1 calc R U . . .
H19B H 0.7352 0.7727 1.0698 0.040 Uiso 1 1 calc R U . . .
C20 C 0.4352(5) 0.80289(4) 0.9605(3) 0.0475(5) Uani 1 1 d . . . . .
H20A H 0.5446 0.8040 0.8591 0.071 Uiso 1 1 calc R U . . .
H20B H 0.5085 0.8185 1.0334 0.071 Uiso 1 1 calc R U . . .
H20C H 0.2073 0.8047 0.9357 0.071 Uiso 1 1 calc R U . . .
N1 N 0.2178(3) 0.55807(3) 0.25954(14) 0.0221(3) Uani 1 1 d . . . . .
O1 O -0.0634(3) 0.58852(2) 0.08799(13) 0.0292(3) Uani 1 1 d . . . . .
O2 O 0.5762(3) 0.52918(2) 0.39739(13) 0.0307(3) Uani 1 1 d . . . . .
O3 O 0.4663(3) 0.64160(2) 0.73836(13) 0.0282(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 1.2118(18) . ?
C1 N1 1.402(2) . ?
C1 C7 1.487(2) 3_565 ?
C2 O2 1.2101(19) . ?
C2 N1 1.4051(19) . ?
C2 C3 1.485(2) . ?
C3 C5 1.375(2) . ?
C3 C4 1.408(2) . ?
C4 C7 1.408(2) 3_565 ?
C4 C4 1.418(3) 3_565 ?
C5 C6 1.405(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.376(2) . ?
C6 H6 0.9500 . ?
C7 C4 1.408(2) 3_565 ?
C7 C1 1.487(2) 3_565 ?
C8 C13 1.380(2) . ?
C8 C9 1.381(2) . ?
C8 N1 1.4556(18) . ?
C9 C10 1.390(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(2) . ?
C10 H10 0.9500 . ?
C11 O3 1.3656(17) . ?
C11 C12 1.392(2) . ?
C12 C13 1.379(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O3 1.4345(18) . ?
C14 C15 1.516(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.521(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.526(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.520(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.522(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.516(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 121.46(13) . . ?
O1 C1 C7 121.96(14) . 3_565 ?
N1 C1 C7 116.58(13) . 3_565 ?
O2 C2 N1 120.94(13) . . ?
O2 C2 C3 122.13(14) . . ?
N1 C2 C3 116.93(13) . . ?
C5 C3 C4 120.46(13) . . ?
C5 C3 C2 119.98(13) . . ?
C4 C3 C2 119.56(13) . . ?
C3 C4 C7 121.39(13) . 3_565 ?
C3 C4 C4 119.26(17) . 3_565 ?
C7 C4 C4 119.34(17) 3_565 3_565 ?
C3 C5 C6 120.21(14) . . ?
C3 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 120.53(14) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C4 120.19(13) . 3_565 ?
C6 C7 C1 119.77(13) . 3_565 ?
C4 C7 C1 120.02(13) 3_565 3_565 ?
C13 C8 C9 120.53(13) . . ?
C13 C8 N1 121.44(13) . . ?
C9 C8 N1 118.02(13) . . ?
C8 C9 C10 120.19(14) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 119.46(14) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
O3 C11 C10 124.65(13) . . ?
O3 C11 C12 115.61(13) . . ?
C10 C11 C12 119.74(13) . . ?
C13 C12 C11 120.50(14) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 119.54(14) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
O3 C14 C15 107.83(13) . . ?
O3 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
O3 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 C16 113.38(13) . . ?
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 113.60(13) . . ?
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 113.54(14) . . ?
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 . . ?
C17 C18 C19 113.63(14) . . ?
C17 C18 H18A 108.8 . . ?
C19 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
C19 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C18 113.51(15) . . ?
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 124.33(12) . . ?
C1 N1 C8 118.72(12) . . ?
C2 N1 C8 116.94(12) . . ?
C11 O3 C14 117.39(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 7.6(2) . . . . ?
N1 C2 C3 C5 -172.35(13) . . . . ?
O2 C2 C3 C4 -172.70(14) . . . . ?
N1 C2 C3 C4 7.4(2) . . . . ?
C5 C3 C4 C7 179.83(14) . . . 3_565 ?
C2 C3 C4 C7 0.1(2) . . . 3_565 ?
C5 C3 C4 C4 -1.0(3) . . . 3_565 ?
C2 C3 C4 C4 179.23(16) . . . 3_565 ?
C4 C3 C5 C6 0.3(2) . . . . ?
C2 C3 C5 C6 -179.99(14) . . . . ?
C3 C5 C6 C7 0.7(2) . . . . ?
C5 C6 C7 C4 -0.9(2) . . . 3_565 ?
C5 C6 C7 C1 177.76(14) . . . 3_565 ?
C13 C8 C9 C10 -1.6(2) . . . . ?
N1 C8 C9 C10 177.14(14) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 O3 -178.11(14) . . . . ?
C9 C10 C11 C12 1.6(2) . . . . ?
O3 C11 C12 C13 177.66(15) . . . . ?
C10 C11 C12 C13 -2.1(2) . . . . ?
C11 C12 C13 C8 0.7(2) . . . . ?
C9 C8 C13 C12 1.1(2) . . . . ?
N1 C8 C13 C12 -177.57(15) . . . . ?
O3 C14 C15 C16 56.94(18) . . . . ?
C14 C15 C16 C17 177.50(14) . . . . ?
C15 C16 C17 C18 177.99(15) . . . . ?
C16 C17 C18 C19 -179.30(15) . . . . ?
C17 C18 C19 C20 -179.80(16) . . . . ?
O1 C1 N1 C2 -169.21(14) . . . . ?
C7 C1 N1 C2 11.3(2) 3_565 . . . ?
O1 C1 N1 C8 9.7(2) . . . . ?
C7 C1 N1 C8 -169.76(13) 3_565 . . . ?
O2 C2 N1 C1 166.56(14) . . . . ?
C3 C2 N1 C1 -13.5(2) . . . . ?
O2 C2 N1 C8 -12.4(2) . . . . ?
C3 C2 N1 C8 167.53(13) . . . . ?
C13 C8 N1 C1 -68.7(2) . . . . ?
C9 C8 N1 C1 112.63(16) . . . . ?
C13 C8 N1 C2 110.35(17) . . . . ?
C9 C8 N1 C2 -68.36(19) . . . . ?
C10 C11 O3 C14 -5.1(2) . . . . ?
C12 C11 O3 C14 175.21(14) . . . . ?
C15 C14 O3 C11 -178.66(13) . . . . ?

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_scd1616_NonNDI_T298K_orange
_database_code_depnum_ccdc_archive 'CCDC 1857163'
#Added by publCIF



_audit_update_record             
;
2018-07-20 deposited with the CCDC.
2018-08-03 downloaded from the CCDC.
;
_publcif_datablock.id            {1d1e1bee-f1e6-4fed-b897-7174805b74de}

_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                   4.362(3)
_cell_length_b                   51.35(4)
_cell_length_c                   8.268(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.56(2)
_cell_angle_gamma                90
_cell_volume                     1848(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5250
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      23.33

_exptl_crystal_description       fragment
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.263
_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    0.083
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6164
_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      298(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'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30722
_diffrn_reflns_av_unetI/netI     0.0956
_diffrn_reflns_av_R_equivalents  0.1033
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -66
_diffrn_reflns_limit_k_max       66
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.593
_diffrn_reflns_theta_max         27.557
_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             4263
_reflns_number_gt                2094
_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)+(0.0490P)²+0.7607P] 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       0.0107(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4263
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1659
_refine_ls_R_factor_gt           0.0660
_refine_ls_wR_factor_ref         0.1481
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.0099(6) 0.44230(5) 0.1258(3) 0.0370(6) Uani 1 1 d . . . . .
C2 C 0.3549(6) 0.47183(5) 0.2901(3) 0.0390(7) Uani 1 1 d . . . . .
C3 C 0.2581(6) 0.49372(4) 0.1837(3) 0.0330(6) Uani 1 1 d . . . . .
C4 C 0.0448(6) 0.48945(4) 0.0508(3) 0.0314(6) Uani 1 1 d . . . . .
C5 C 0.3708(6) 0.51827(5) 0.2145(3) 0.0395(7) Uani 1 1 d . . . . .
H5 H 0.5093 0.5210 0.3029 0.047 Uiso 1 1 calc R U . . .
C6 C 0.2797(6) 0.53926(5) 0.1143(3) 0.0395(7) Uani 1 1 d . . . . .
H6 H 0.3570 0.5558 0.1371 0.047 Uiso 1 1 calc R U . . .
C7 C 0.0760(6) 0.53547(4) -0.0178(3) 0.0325(6) Uani 1 1 d . . . . .
C8 C 0.2569(6) 0.42778(5) 0.3863(3) 0.0380(6) Uani 1 1 d . . . . .
C9 C 0.1336(6) 0.43121(5) 0.5341(3) 0.0427(7) Uani 1 1 d . . . . .
H9 H 0.0116 0.4457 0.5517 0.051 Uiso 1 1 calc R U . . .
C10 C 0.1916(6) 0.41303(5) 0.6570(3) 0.0403(7) Uani 1 1 d . . . . .
H10 H 0.1096 0.4154 0.7572 0.048 Uiso 1 1 calc R U . . .
C11 C 0.3707(6) 0.39164(5) 0.6297(3) 0.0380(6) Uani 1 1 d . . . . .
C12 C 0.4859(7) 0.38802(5) 0.4790(3) 0.0478(7) Uani 1 1 d . . . . .
H12 H 0.6006 0.3732 0.4592 0.057 Uiso 1 1 calc R U . . .
C13 C 0.4317(6) 0.40620(5) 0.3582(3) 0.0443(7) Uani 1 1 d . . . . .
H13 H 0.5132 0.4039 0.2579 0.053 Uiso 1 1 calc R U . . .
C14 C 0.3158(7) 0.37429(5) 0.8963(3) 0.0486(8) Uani 1 1 d . . . . .
H14A H 0.0934 0.3742 0.8817 0.058 Uiso 1 1 calc R U . . .
H14B H 0.3793 0.3902 0.9518 0.058 Uiso 1 1 calc R U . . .
C15 C 0.4264(7) 0.35089(5) 0.9938(3) 0.0502(8) Uani 1 1 d . . . . .
H15A H 0.6474 0.3521 1.0137 0.060 Uiso 1 1 calc R U . . .
H15B H 0.3358 0.3513 1.0980 0.060 Uiso 1 1 calc R U . . .
C16 C 0.3498(7) 0.32513(5) 0.9132(3) 0.0515(8) Uani 1 1 d . . . . .
H16A H 0.4470 0.3245 0.8109 0.062 Uiso 1 1 calc R U . . .
H16B H 0.1295 0.3244 0.8890 0.062 Uiso 1 1 calc R U . . .
C17 C 0.4465(7) 0.30118(5) 1.0107(3) 0.0526(8) Uani 1 1 d . . . . .
H17A H 0.6659 0.3021 1.0375 0.063 Uiso 1 1 calc R U . . .
H17B H 0.3442 0.3014 1.1115 0.063 Uiso 1 1 calc R U . . .
C18 C 0.3753(7) 0.27579(5) 0.9251(3) 0.0547(8) Uani 1 1 d . . . . .
H18A H 0.4760 0.2758 0.8238 0.066 Uiso 1 1 calc R U . . .
H18B H 0.1557 0.2750 0.8987 0.066 Uiso 1 1 calc R U . . .
C19 C 0.4696(7) 0.25151(5) 1.0177(3) 0.0550(8) Uani 1 1 d . . . . .
H19A H 0.6890 0.2523 1.0449 0.066 Uiso 1 1 calc R U . . .
H19B H 0.3672 0.2514 1.1185 0.066 Uiso 1 1 calc R U . . .
C20 C 0.3991(8) 0.22636(5) 0.9295(3) 0.0575(8) Uani 1 1 d . . . . .
H20A H 0.1795 0.2255 0.9030 0.069 Uiso 1 1 calc R U . . .
H20B H 0.5002 0.2266 0.8283 0.069 Uiso 1 1 calc R U . . .
C21 C 0.4953(8) 0.20215(5) 1.0214(4) 0.0657(9) Uani 1 1 d . . . . .
H21A H 0.7145 0.2031 1.0486 0.079 Uiso 1 1 calc R U . . .
H21B H 0.3934 0.2020 1.1224 0.079 Uiso 1 1 calc R U . . .
C22 C 0.4287(9) 0.17679(6) 0.9357(5) 0.0878(12) Uani 1 1 d . . . . .
H22A H 0.2116 0.1752 0.9107 0.132 Uiso 1 1 calc R U . . .
H22B H 0.4980 0.1626 1.0044 0.132 Uiso 1 1 calc R U . . .
H22C H 0.5341 0.1763 0.8372 0.132 Uiso 1 1 calc R U . . .
N1 N 0.2031(5) 0.44791(4) 0.2635(2) 0.0365(5) Uani 1 1 d . . . . .
O1 O -0.0808(4) 0.42031(3) 0.0981(2) 0.0508(5) Uani 1 1 d . . . . .
O2 O 0.5587(5) 0.47379(3) 0.3967(2) 0.0529(5) Uani 1 1 d . . . . .
O3 O 0.4489(4) 0.37280(3) 0.7422(2) 0.0496(5) 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(3) . ?
C1 N1 1.404(3) . ?
C1 C7 1.483(3) 3_565 ?
C2 O2 1.216(3) . ?
C2 N1 1.406(3) . ?
C2 C3 1.473(3) . ?
C3 C5 1.371(3) . ?
C3 C4 1.412(3) . ?
C4 C7 1.404(3) 3_565 ?
C4 C4 1.411(4) 3_565 ?
C5 C6 1.402(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(3) . ?
C6 H6 0.9300 . ?
C7 C4 1.405(3) 3_565 ?
C7 C1 1.483(3) 3_565 ?
C8 C13 1.373(3) . ?
C8 C9 1.376(3) . ?
C8 N1 1.458(3) . ?
C9 C10 1.392(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(3) . ?
C10 H10 0.9300 . ?
C11 O3 1.370(3) . ?
C11 C12 1.385(3) . ?
C12 C13 1.377(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 O3 1.434(3) . ?
C14 C15 1.509(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.509(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.516(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.506(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.507(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.505(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.503(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.502(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
O1 C1 N1 121.1(2) . . ?
O1 C1 C7 122.4(2) . 3_565 ?
N1 C1 C7 116.6(2) . 3_565 ?
O2 C2 N1 120.1(2) . . ?
O2 C2 C3 122.6(2) . . ?
N1 C2 C3 117.3(2) . . ?
C5 C3 C4 119.9(2) . . ?
C5 C3 C2 120.3(2) . . ?
C4 C3 C2 119.8(2) . . ?
C7 C4 C4 119.8(3) 3_565 3_565 ?
C7 C4 C3 120.9(2) 3_565 . ?
C4 C4 C3 119.3(3) 3_565 . ?
C3 C5 C6 120.8(2) . . ?
C3 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C4 119.9(2) . 3_565 ?
C6 C7 C1 119.7(2) . 3_565 ?
C4 C7 C1 120.4(2) 3_565 3_565 ?
C13 C8 C9 120.4(2) . . ?
C13 C8 N1 121.4(2) . . ?
C9 C8 N1 118.2(2) . . ?
C8 C9 C10 119.9(2) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
O3 C11 C10 125.0(2) . . ?
O3 C11 C12 115.3(2) . . ?
C10 C11 C12 119.8(2) . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C8 C13 C12 119.8(2) . . ?
C8 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
O3 C14 C15 107.4(2) . . ?
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 . . ?
C16 C15 C14 114.0(2) . . ?
C16 C15 H15A 108.7 . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C14 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 C17 115.5(2) . . ?
C15 C16 H16A 108.4 . . ?
C17 C16 H16A 108.4 . . ?
C15 C16 H16B 108.4 . . ?
C17 C16 H16B 108.4 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C16 114.2(2) . . ?
C18 C17 H17A 108.7 . . ?
C16 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C16 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C17 C18 C19 115.8(2) . . ?
C17 C18 H18A 108.3 . . ?
C19 C18 H18A 108.3 . . ?
C17 C18 H18B 108.3 . . ?
C19 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
C20 C19 C18 115.0(2) . . ?
C20 C19 H19A 108.5 . . ?
C18 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
C18 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C21 C20 C19 115.0(2) . . ?
C21 C20 H20A 108.5 . . ?
C19 C20 H20A 108.5 . . ?
C21 C20 H20B 108.5 . . ?
C19 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
C22 C21 C20 116.0(3) . . ?
C22 C21 H21A 108.3 . . ?
C20 C21 H21A 108.3 . . ?
C22 C21 H21B 108.3 . . ?
C20 C21 H21B 108.3 . . ?
H21A C21 H21B 107.4 . . ?
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 123.99(19) . . ?
C1 N1 C8 118.8(2) . . ?
C2 N1 C8 117.16(19) . . ?
C11 O3 C14 117.9(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
O2 C2 C3 C5 -8.1(4) . . . . ?
N1 C2 C3 C5 172.5(2) . . . . ?
O2 C2 C3 C4 172.8(2) . . . . ?
N1 C2 C3 C4 -6.6(3) . . . . ?
C5 C3 C4 C7 -179.4(2) . . . 3_565 ?
C2 C3 C4 C7 -0.3(3) . . . 3_565 ?
C5 C3 C4 C4 1.3(4) . . . 3_565 ?
C2 C3 C4 C4 -179.7(3) . . . 3_565 ?
C4 C3 C5 C6 -0.8(4) . . . . ?
C2 C3 C5 C6 -179.8(2) . . . . ?
C3 C5 C6 C7 -0.4(4) . . . . ?
C5 C6 C7 C4 1.0(4) . . . 3_565 ?
C5 C6 C7 C1 -177.9(2) . . . 3_565 ?
C13 C8 C9 C10 1.4(4) . . . . ?
N1 C8 C9 C10 -177.0(2) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 C10 C11 O3 178.5(2) . . . . ?
C9 C10 C11 C12 -1.5(4) . . . . ?
O3 C11 C12 C13 -177.6(2) . . . . ?
C10 C11 C12 C13 2.4(4) . . . . ?
C9 C8 C13 C12 -0.5(4) . . . . ?
N1 C8 C13 C12 177.9(2) . . . . ?
C11 C12 C13 C8 -1.4(4) . . . . ?
O3 C14 C15 C16 -57.4(3) . . . . ?
C14 C15 C16 C17 -177.7(3) . . . . ?
C15 C16 C17 C18 -178.3(3) . . . . ?
C16 C17 C18 C19 179.6(3) . . . . ?
C17 C18 C19 C20 -179.5(3) . . . . ?
C18 C19 C20 C21 179.6(3) . . . . ?
C19 C20 C21 C22 -179.7(3) . . . . ?
O1 C1 N1 C2 169.6(2) . . . . ?
C7 C1 N1 C2 -10.5(3) 3_565 . . . ?
O1 C1 N1 C8 -9.2(4) . . . . ?
C7 C1 N1 C8 170.7(2) 3_565 . . . ?
O2 C2 N1 C1 -167.1(2) . . . . ?
C3 C2 N1 C1 12.4(3) . . . . ?
O2 C2 N1 C8 11.7(3) . . . . ?
C3 C2 N1 C8 -168.8(2) . . . . ?
C13 C8 N1 C1 71.1(3) . . . . ?
C9 C8 N1 C1 -110.5(3) . . . . ?
C13 C8 N1 C2 -107.8(3) . . . . ?
C9 C8 N1 C2 70.6(3) . . . . ?
C10 C11 O3 C14 5.1(4) . . . . ?
C12 C11 O3 C14 -174.9(2) . . . . ?
C15 C14 O3 C11 177.5(2) . . . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_scd1707_OctNDI_T200K_orange
_database_code_depnum_ccdc_archive 'CCDC 1857160'
#Added by publCIF



_audit_update_record             
;
2018-07-20 deposited with the CCDC.
2018-08-03 downloaded from the CCDC.
;
_publcif_datablock.id            {83926acc-6b96-4904-97ab-69ab5beb6d78}

_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                   4.2498(17)
_cell_length_b                   8.217(3)
_cell_length_c                   24.826(7)
_cell_angle_alpha                97.903(9)
_cell_angle_beta                 93.317(9)
_cell_angle_gamma                93.732(8)
_cell_volume                     854.9(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5983
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      27.22

_exptl_crystal_description       fragment
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_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    0.087
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5403
_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      200(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            21943
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_av_R_equivalents  0.0678
_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         2.491
_diffrn_reflns_theta_max         27.566
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3953
_reflns_number_gt                2460
_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)+(0.0492P)²+0.2668P] 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       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3953
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1298
_refine_ls_wR_factor_gt          0.1105
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.3243(4) 0.78823(18) 0.11003(6) 0.0223(4) Uani 1 1 d . . . . .
O1 O -0.0553(3) 0.62636(17) 0.05538(5) 0.0309(4) Uani 1 1 d . . . . .
O2 O 0.6264(3) 0.98520(16) 0.16775(5) 0.0295(4) Uani 1 1 d . . . . .
O3 O 0.1321(3) 0.37936(16) 0.26879(5) 0.0287(3) Uani 1 1 d . . . . .
C1 C 0.1533(4) 0.7358(2) 0.05987(7) 0.0227(4) Uani 1 1 d . . . . .
C2 C 0.5209(4) 0.9336(2) 0.12168(7) 0.0225(4) Uani 1 1 d . . . . .
C3 C 0.5967(4) 1.0204(2) 0.07472(7) 0.0207(4) Uani 1 1 d . . . . .
C4 C 0.8070(4) 1.1574(2) 0.08260(7) 0.0237(4) Uani 1 1 d . . . . .
H4 H 0.8967 1.1984 0.1182 0.028 Uiso 1 1 calc R U . . .
C5 C 0.8898(4) 1.2369(2) 0.03832(7) 0.0246(5) Uani 1 1 d . . . . .
H5 H 1.0371 1.3307 0.0440 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7586(4) 1.1797(2) -0.01316(7) 0.0208(4) Uani 1 1 d . . . . .
C7 C 0.5399(4) 1.0407(2) -0.02234(7) 0.0190(4) Uani 1 1 d . . . . .
C8 C 0.2852(4) 0.6841(2) 0.15251(7) 0.0230(4) Uani 1 1 d . . . . .
C9 C 0.4039(4) 0.5313(2) 0.14560(7) 0.0241(4) Uani 1 1 d . . . . .
H9 H 0.5159 0.4983 0.1144 0.029 Uiso 1 1 calc R U . . .
C10 C 0.3613(4) 0.4251(2) 0.18383(7) 0.0235(4) Uani 1 1 d . . . . .
H10 H 0.4429 0.3195 0.1789 0.028 Uiso 1 1 calc R U . . .
C11 C 0.1982(4) 0.4746(2) 0.22946(7) 0.0221(4) Uani 1 1 d . . . . .
C12 C 0.0871(5) 0.6304(2) 0.23657(7) 0.0273(5) Uani 1 1 d . . . . .
H12 H -0.0191 0.6656 0.2683 0.033 Uiso 1 1 calc R U . . .
C13 C 0.1284(5) 0.7350(2) 0.19830(7) 0.0262(5) Uani 1 1 d . . . . .
H13 H 0.0497 0.8412 0.2034 0.031 Uiso 1 1 calc R U . . .
C14 C 0.2632(5) 0.2225(2) 0.26533(8) 0.0287(5) Uani 1 1 d . . . . .
H14A H 0.4963 0.2365 0.2652 0.034 Uiso 1 1 calc R U . . .
H14B H 0.1808 0.1516 0.2313 0.034 Uiso 1 1 calc R U . . .
C15 C 0.1690(5) 0.1443(2) 0.31447(7) 0.0279(5) Uani 1 1 d . . . . .
H15A H 0.2633 0.0369 0.3135 0.033 Uiso 1 1 calc R U . . .
H15B H -0.0637 0.1228 0.3122 0.033 Uiso 1 1 calc R U . . .
C16 C 0.2731(5) 0.2505(2) 0.36837(7) 0.0289(5) Uani 1 1 d . . . . .
H16A H 0.1710 0.3558 0.3699 0.035 Uiso 1 1 calc R U . . .
H16B H 0.5044 0.2764 0.3697 0.035 Uiso 1 1 calc R U . . .
C17 C 0.1942(5) 0.1711(2) 0.41853(7) 0.0290(5) Uani 1 1 d . . . . .
H17A H -0.0367 0.1436 0.4172 0.035 Uiso 1 1 calc R U . . .
H17B H 0.3001 0.0671 0.4177 0.035 Uiso 1 1 calc R U . . .
C18 C 0.2962(5) 0.2821(3) 0.47133(7) 0.0310(5) Uani 1 1 d . . . . .
H18A H 0.1888 0.3856 0.4717 0.037 Uiso 1 1 calc R U . . .
H18B H 0.5263 0.3110 0.4718 0.037 Uiso 1 1 calc R U . . .
C19 C 0.2292(5) 0.2108(3) 0.52329(7) 0.0302(5) Uani 1 1 d . . . . .
H19A H -0.0011 0.1844 0.5238 0.036 Uiso 1 1 calc R U . . .
H19B H 0.3348 0.1069 0.5234 0.036 Uiso 1 1 calc R U . . .
C20 C 0.3431(5) 0.3284(3) 0.57425(8) 0.0350(5) Uani 1 1 d . . . . .
H20A H 0.5727 0.3558 0.5731 0.042 Uiso 1 1 calc R U . . .
H20B H 0.2362 0.4318 0.5739 0.042 Uiso 1 1 calc R U . . .
C21 C 0.2850(6) 0.2629(3) 0.62726(8) 0.0475(6) Uani 1 1 d . . . . .
H21A H 0.0572 0.2428 0.6301 0.071 Uiso 1 1 calc R U . . .
H21B H 0.3733 0.3439 0.6580 0.071 Uiso 1 1 calc R U . . .
H21C H 0.3871 0.1595 0.6279 0.071 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 1.398(2) . ?
N1 C1 1.404(2) . ?
N1 C8 1.456(2) . ?
O1 C1 1.210(2) . ?
O2 C2 1.213(2) . ?
O3 C11 1.363(2) . ?
O3 C14 1.431(2) . ?
C1 C6 1.485(2) 2_675 ?
C2 C3 1.488(2) . ?
C3 C4 1.376(3) . ?
C3 C7 1.405(3) 2_675 ?
C4 C5 1.404(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.372(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.410(3) . ?
C6 C1 1.485(2) 2_675 ?
C7 C3 1.405(3) 2_675 ?
C7 C7 1.418(3) 2_675 ?
C8 C9 1.376(3) . ?
C8 C13 1.380(2) . ?
C9 C10 1.386(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(3) . ?
C12 C13 1.377(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.517(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.519(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.527(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.514(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.522(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.517(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.516(3) . ?
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 124.34(15) . . ?
C2 N1 C8 118.88(15) . . ?
C1 N1 C8 116.77(15) . . ?
C11 O3 C14 117.62(14) . . ?
O1 C1 N1 120.95(16) . . ?
O1 C1 C6 122.09(17) . 2_675 ?
N1 C1 C6 116.96(16) . 2_675 ?
O2 C2 N1 121.51(16) . . ?
O2 C2 C3 121.80(17) . . ?
N1 C2 C3 116.68(16) . . ?
C4 C3 C7 120.38(16) . 2_675 ?
C4 C3 C2 119.75(17) . . ?
C7 C3 C2 119.84(17) 2_675 . ?
C3 C4 C5 120.37(17) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.24(17) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.61(16) . . ?
C5 C6 C1 120.08(17) . 2_675 ?
C7 C6 C1 119.31(17) . 2_675 ?
C3 C7 C6 121.61(16) 2_675 . ?
C3 C7 C7 119.4(2) 2_675 2_675 ?
C6 C7 C7 119.0(2) . 2_675 ?
C9 C8 C13 120.28(17) . . ?
C9 C8 N1 118.41(15) . . ?
C13 C8 N1 121.30(17) . . ?
C8 C9 C10 120.52(17) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 119.36(18) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
O3 C11 C12 115.77(16) . . ?
O3 C11 C10 124.75(17) . . ?
C12 C11 C10 119.48(16) . . ?
C13 C12 C11 120.90(17) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C8 119.43(18) . . ?
C12 C13 H13 120.3 . . ?
C8 C13 H13 120.3 . . ?
O3 C14 C15 107.65(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 113.17(16) . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 114.19(16) . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C18 C17 C16 112.52(17) . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 C19 115.70(17) . . ?
C17 C18 H18A 108.4 . . ?
C19 C18 H18A 108.4 . . ?
C17 C18 H18B 108.4 . . ?
C19 C18 H18B 108.4 . . ?
H18A C18 H18B 107.4 . . ?
C20 C19 C18 112.38(17) . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C21 C20 C19 114.60(18) . . ?
C21 C20 H20A 108.6 . . ?
C19 C20 H20A 108.6 . . ?
C21 C20 H20B 108.6 . . ?
C19 C20 H20B 108.6 . . ?
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 -166.28(18) . . . . ?
C8 N1 C1 O1 12.3(3) . . . . ?
C2 N1 C1 C6 13.9(2) . . . 2_675 ?
C8 N1 C1 C6 -167.48(15) . . . 2_675 ?
C1 N1 C2 O2 169.07(17) . . . . ?
C8 N1 C2 O2 -9.5(3) . . . . ?
C1 N1 C2 C3 -11.6(2) . . . . ?
C8 N1 C2 C3 169.82(15) . . . . ?
O2 C2 C3 C4 4.1(3) . . . . ?
N1 C2 C3 C4 -175.26(16) . . . . ?
O2 C2 C3 C7 -177.74(17) . . . 2_675 ?
N1 C2 C3 C7 2.9(3) . . . 2_675 ?
C7 C3 C4 C5 -0.6(3) 2_675 . . . ?
C2 C3 C4 C5 177.61(17) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C4 C5 C6 C1 179.98(17) . . . 2_675 ?
C5 C6 C7 C3 -179.80(17) . . . 2_675 ?
C1 C6 C7 C3 0.2(3) 2_675 . . 2_675 ?
C5 C6 C7 C7 -0.8(3) . . . 2_675 ?
C1 C6 C7 C7 179.15(19) 2_675 . . 2_675 ?
C2 N1 C8 C9 -113.0(2) . . . . ?
C1 N1 C8 C9 68.3(2) . . . . ?
C2 N1 C8 C13 68.2(2) . . . . ?
C1 N1 C8 C13 -110.5(2) . . . . ?
C13 C8 C9 C10 1.5(3) . . . . ?
N1 C8 C9 C10 -177.38(16) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C14 O3 C11 C12 -175.27(17) . . . . ?
C14 O3 C11 C10 5.6(3) . . . . ?
C9 C10 C11 O3 177.65(17) . . . . ?
C9 C10 C11 C12 -1.4(3) . . . . ?
O3 C11 C12 C13 -177.33(17) . . . . ?
C10 C11 C12 C13 1.8(3) . . . . ?
C11 C12 C13 C8 -0.6(3) . . . . ?
C9 C8 C13 C12 -1.1(3) . . . . ?
N1 C8 C13 C12 177.74(18) . . . . ?
C11 O3 C14 C15 177.55(15) . . . . ?
O3 C14 C15 C16 -56.9(2) . . . . ?
C14 C15 C16 C17 -177.38(17) . . . . ?
C15 C16 C17 C18 -178.93(17) . . . . ?
C16 C17 C18 C19 -179.29(17) . . . . ?
C17 C18 C19 C20 179.08(18) . . . . ?
C18 C19 C20 C21 -179.45(18) . . . . ?

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_scd1658_HeptNDI_T298K
_database_code_depnum_ccdc_archive 'CCDC 1857159'
#Added by publCIF



_audit_update_record             
;
2018-07-20 deposited with the CCDC.
2018-08-03 downloaded from the CCDC.
;
_publcif_datablock.id            {926f7141-fc6b-45ac-acc2-17f0ab16882e}

_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                   4.3773(18)
_cell_length_b                   46.183(15)
_cell_length_c                   8.215(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.759(6)
_cell_angle_gamma                90
_cell_volume                     1657.2(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9780
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      26.96

_exptl_crystal_description       fragment
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_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    0.087
_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  0.6948
_exptl_absorpt_correction_T_max  0.7447
_exptl_absorpt_process_details   
;
SADABS (Krause, Herbst-Irmer, Sheldrick, & Stalke;  J. Appl. Cryst. 2015, 48,
3-10)
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(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'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40572
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -59
_diffrn_reflns_limit_k_max       59
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.523
_diffrn_reflns_theta_max         27.508
_diffrn_reflns_theta_full        25.242
_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             3820
_reflns_number_gt                2508
_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)+(0.0522P)²+0.5259P] 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       0.0114(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3820
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.0077(4) 0.56404(4) 0.1277(2) 0.0349(4) Uani 1 1 d . . . . .
C2 C 0.3577(4) 0.53153(4) 0.2913(2) 0.0359(4) Uani 1 1 d . . . . .
C3 C 0.2596(4) 0.50698(3) 0.18414(19) 0.0325(4) Uani 1 1 d . . . . .
C4 C 0.0448(4) 0.51177(3) 0.05140(18) 0.0300(4) Uani 1 1 d . . . . .
C5 C 0.3766(4) 0.47984(4) 0.2143(2) 0.0381(4) Uani 1 1 d . . . . .
H5 H 0.5174 0.4768 0.3025 0.046 Uiso 1 1 calc R U . . .
C6 C 0.2850(4) 0.45656(4) 0.1130(2) 0.0373(4) Uani 1 1 d . . . . .
H6 H 0.3645 0.4382 0.1349 0.045 Uiso 1 1 calc R U . . .
C7 C 0.0791(4) 0.46064(3) -0.01837(19) 0.0316(4) Uani 1 1 d . . . . .
C8 C 0.2550(4) 0.58018(4) 0.3891(2) 0.0361(4) Uani 1 1 d . . . . .
C9 C 0.1307(4) 0.57635(4) 0.5369(2) 0.0402(4) Uani 1 1 d . . . . .
H9 H 0.0090 0.5603 0.5539 0.048 Uiso 1 1 calc R U . . .
C10 C 0.1867(4) 0.59644(4) 0.6608(2) 0.0395(4) Uani 1 1 d . . . . .
H10 H 0.1032 0.5938 0.7610 0.047 Uiso 1 1 calc R U . . .
C11 C 0.3667(4) 0.62030(3) 0.6346(2) 0.0363(4) Uani 1 1 d . . . . .
C12 C 0.4853(5) 0.62416(4) 0.4837(2) 0.0454(5) Uani 1 1 d . . . . .
H12 H 0.6032 0.6404 0.4650 0.054 Uiso 1 1 calc R U . . .
C13 C 0.4302(5) 0.60414(4) 0.3614(2) 0.0425(5) Uani 1 1 d . . . . .
H13 H 0.5110 0.6068 0.2605 0.051 Uiso 1 1 calc R U . . .
C14 C 0.3106(5) 0.63919(4) 0.9021(2) 0.0473(5) Uani 1 1 d . . . . .
H14A H 0.3701 0.6212 0.9564 0.057 Uiso 1 1 calc R U . . .
H14B H 0.0891 0.6397 0.8866 0.057 Uiso 1 1 calc R U . . .
C15 C 0.4248(5) 0.66474(4) 1.0037(2) 0.0492(5) Uani 1 1 d . . . . .
H15A H 0.3354 0.6639 1.1086 0.059 Uiso 1 1 calc R U . . .
H15B H 0.6451 0.6632 1.0234 0.059 Uiso 1 1 calc R U . . .
C16 C 0.3501(5) 0.69369(4) 0.9257(2) 0.0508(5) Uani 1 1 d . . . . .
H16A H 0.1304 0.6949 0.9019 0.061 Uiso 1 1 calc R U . . .
H16B H 0.4461 0.6947 0.8227 0.061 Uiso 1 1 calc R U . . .
C17 C 0.4517(5) 0.71968(4) 1.0285(2) 0.0539(5) Uani 1 1 d . . . . .
H17A H 0.3496 0.7191 1.1297 0.065 Uiso 1 1 calc R U . . .
H17B H 0.6701 0.7182 1.0557 0.065 Uiso 1 1 calc R U . . .
C18 C 0.3867(6) 0.74857(4) 0.9470(3) 0.0574(6) Uani 1 1 d . . . . .
H18A H 0.4877 0.7491 0.8455 0.069 Uiso 1 1 calc R U . . .
H18B H 0.1681 0.7501 0.9202 0.069 Uiso 1 1 calc R U . . .
C19 C 0.4876(6) 0.77446(4) 1.0471(3) 0.0645(6) Uani 1 1 d . . . . .
H19A H 0.7061 0.7730 1.0739 0.077 Uiso 1 1 calc R U . . .
H19B H 0.3866 0.7740 1.1487 0.077 Uiso 1 1 calc R U . . .
C20 C 0.4225(7) 0.80313(5) 0.9661(4) 0.0875(9) Uani 1 1 d . . . . .
H20A H 0.5232 0.8040 0.8658 0.131 Uiso 1 1 calc R U . . .
H20B H 0.4970 0.8184 1.0371 0.131 Uiso 1 1 calc R U . . .
H20C H 0.2057 0.8053 0.9435 0.131 Uiso 1 1 calc R U . . .
N1 N 0.2023(3) 0.55785(3) 0.26511(16) 0.0357(4) Uani 1 1 d . . . . .
O1 O -0.0870(3) 0.58834(3) 0.10073(15) 0.0476(4) Uani 1 1 d . . . . .
O2 O 0.5610(3) 0.52929(3) 0.39722(15) 0.0501(4) Uani 1 1 d . . . . .
O3 O 0.4437(3) 0.64103(3) 0.74832(15) 0.0470(4) 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 1.212(2) . ?
C1 N1 1.398(2) . ?
C1 C7 1.485(2) 3_565 ?
C2 O2 1.207(2) . ?
C2 N1 1.403(2) . ?
C2 C3 1.482(2) . ?
C3 C5 1.371(2) . ?
C3 C4 1.410(2) . ?
C4 C7 1.405(2) 3_565 ?
C4 C4 1.416(3) 3_565 ?
C5 C6 1.402(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.373(2) . ?
C6 H6 0.9300 . ?
C7 C4 1.405(2) 3_565 ?
C7 C1 1.485(2) 3_565 ?
C8 C13 1.374(2) . ?
C8 C9 1.374(2) . ?
C8 N1 1.457(2) . ?
C9 C10 1.387(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.380(2) . ?
C10 H10 0.9300 . ?
C11 O3 1.3644(19) . ?
C11 C12 1.386(3) . ?
C12 C13 1.375(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 O3 1.428(2) . ?
C14 C15 1.511(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.510(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.517(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.511(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.501(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.501(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
O1 C1 N1 121.34(15) . . ?
O1 C1 C7 121.95(16) . 3_565 ?
N1 C1 C7 116.71(14) . 3_565 ?
O2 C2 N1 120.80(15) . . ?
O2 C2 C3 122.27(16) . . ?
N1 C2 C3 116.93(15) . . ?
C5 C3 C4 120.38(15) . . ?
C5 C3 C2 120.13(15) . . ?
C4 C3 C2 119.50(15) . . ?
C7 C4 C3 121.42(14) 3_565 . ?
C7 C4 C4 119.52(18) 3_565 3_565 ?
C3 C4 C4 119.05(19) . 3_565 ?
C3 C5 C6 120.33(16) . . ?
C3 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 120.59(16) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C4 120.12(15) . 3_565 ?
C6 C7 C1 119.92(15) . 3_565 ?
C4 C7 C1 119.95(15) 3_565 3_565 ?
C13 C8 C9 120.53(15) . . ?
C13 C8 N1 121.22(15) . . ?
C9 C8 N1 118.23(15) . . ?
C8 C9 C10 120.06(16) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 119.67(17) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
O3 C11 C10 124.84(16) . . ?
O3 C11 C12 115.60(15) . . ?
C10 C11 C12 119.56(15) . . ?
C13 C12 C11 120.59(17) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C8 C13 C12 119.56(17) . . ?
C8 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
O3 C14 C15 107.66(16) . . ?
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 . . ?
C16 C15 C14 113.71(16) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 114.64(17) . . ?
C15 C16 H16A 108.6 . . ?
C17 C16 H16A 108.6 . . ?
C15 C16 H16B 108.6 . . ?
C17 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C18 C17 C16 114.35(17) . . ?
C18 C17 H17A 108.7 . . ?
C16 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C16 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 114.88(18) . . ?
C19 C18 H18A 108.5 . . ?
C17 C18 H18A 108.5 . . ?
C19 C18 H18B 108.5 . . ?
C17 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C18 C19 C20 114.8(2) . . ?
C18 C19 H19A 108.6 . . ?
C20 C19 H19A 108.6 . . ?
C18 C19 H19B 108.6 . . ?
C20 C19 H19B 108.6 . . ?
H19A C19 H19B 107.5 . . ?
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 124.39(13) . . ?
C1 N1 C8 118.68(14) . . ?
C2 N1 C8 116.92(14) . . ?
C11 O3 C14 117.88(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 7.2(3) . . . . ?
N1 C2 C3 C5 -172.62(16) . . . . ?
O2 C2 C3 C4 -173.01(17) . . . . ?
N1 C2 C3 C4 7.2(2) . . . . ?
C5 C3 C4 C7 179.76(16) . . . 3_565 ?
C2 C3 C4 C7 -0.1(2) . . . 3_565 ?
C5 C3 C4 C4 -0.9(3) . . . 3_565 ?
C2 C3 C4 C4 179.31(19) . . . 3_565 ?
C4 C3 C5 C6 0.3(3) . . . . ?
C2 C3 C5 C6 -179.84(16) . . . . ?
C3 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 C4 -0.7(3) . . . 3_565 ?
C5 C6 C7 C1 177.97(16) . . . 3_565 ?
C13 C8 C9 C10 -1.3(3) . . . . ?
N1 C8 C9 C10 177.15(16) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 O3 -178.21(17) . . . . ?
C9 C10 C11 C12 1.1(3) . . . . ?
O3 C11 C12 C13 178.03(18) . . . . ?
C10 C11 C12 C13 -1.3(3) . . . . ?
C9 C8 C13 C12 1.1(3) . . . . ?
N1 C8 C13 C12 -177.33(18) . . . . ?
C11 C12 C13 C8 0.3(3) . . . . ?
O3 C14 C15 C16 58.1(2) . . . . ?
C14 C15 C16 C17 177.75(19) . . . . ?
C15 C16 C17 C18 177.8(2) . . . . ?
C16 C17 C18 C19 -179.7(2) . . . . ?
C17 C18 C19 C20 -179.9(2) . . . . ?
O1 C1 N1 C2 -169.75(17) . . . . ?
C7 C1 N1 C2 10.9(2) 3_565 . . . ?
O1 C1 N1 C8 8.9(3) . . . . ?
C7 C1 N1 C8 -170.39(15) 3_565 . . . ?
O2 C2 N1 C1 167.15(17) . . . . ?
C3 C2 N1 C1 -13.1(2) . . . . ?
O2 C2 N1 C8 -11.6(2) . . . . ?
C3 C2 N1 C8 168.24(15) . . . . ?
C13 C8 N1 C1 -72.1(2) . . . . ?
C9 C8 N1 C1 109.43(19) . . . . ?
C13 C8 N1 C2 106.6(2) . . . . ?
C9 C8 N1 C2 -71.8(2) . . . . ?
C10 C11 O3 C14 -4.9(3) . . . . ?
C12 C11 O3 C14 175.76(17) . . . . ?
C15 C14 O3 C11 -178.65(16) . . . . ?

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_scd1708_OctNDI_T298K_orange
_database_code_depnum_ccdc_archive 'CCDC 1857161'
#Added by publCIF



_audit_update_record             
;
2018-07-20 deposited with the CCDC.
2018-08-03 downloaded from the CCDC.
;
_publcif_datablock.id            {e16e32ff-9ff0-40c2-86f9-5668c09d1806}

_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                   4.3797(17)
_cell_length_b                   8.220(3)
_cell_length_c                   24.683(8)
_cell_angle_alpha                98.313(13)
_cell_angle_beta                 93.051(8)
_cell_angle_gamma                93.777(6)
_cell_volume                     875.6(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5760
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      26.73

_exptl_crystal_description       fragment
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_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    0.085
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5334
_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      298(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'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28393
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_av_R_equivalents  0.0889
_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         2.507
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4061
_reflns_number_gt                2116
_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)+(0.0521P)²+0.2619P] 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       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4061
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1438
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1430
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 0.3361(4) 0.7843(2) 0.10965(7) 0.0351(4) Uani 1 1 d . . . . .
O1 O -0.0402(4) 0.6278(2) 0.05547(6) 0.0497(5) Uani 1 1 d . . . . .
O2 O 0.6433(4) 0.97498(19) 0.16744(6) 0.0474(4) Uani 1 1 d . . . . .
O3 O 0.1463(4) 0.37412(19) 0.26767(6) 0.0472(5) Uani 1 1 d . . . . .
C1 C 0.1643(5) 0.7357(3) 0.05984(8) 0.0350(5) Uani 1 1 d . . . . .
C2 C 0.5338(5) 0.9270(3) 0.12137(9) 0.0346(5) Uani 1 1 d . . . . .
C3 C 0.6045(5) 1.0154(2) 0.07476(8) 0.0314(5) Uani 1 1 d . . . . .
C4 C 0.8119(5) 1.1505(3) 0.08241(8) 0.0368(5) Uani 1 1 d . . . . .
H4 H 0.9026 1.1888 0.1172 0.044 Uiso 1 1 calc R U . . .
C5 C 0.8885(5) 1.2315(3) 0.03818(8) 0.0380(6) Uani 1 1 d . . . . .
H5 H 1.0311 1.3223 0.0438 0.046 Uiso 1 1 calc R U . . .
C6 C 0.7546(5) 1.1778(2) -0.01316(8) 0.0318(5) Uani 1 1 d . . . . .
C7 C 0.5374(5) 1.0414(2) -0.02226(8) 0.0290(5) Uani 1 1 d . . . . .
C8 C 0.2977(5) 0.6796(3) 0.15199(8) 0.0347(5) Uani 1 1 d . . . . .
C9 C 0.4177(5) 0.5289(3) 0.14513(8) 0.0394(6) Uani 1 1 d . . . . .
H9 H 0.5289 0.4979 0.1147 0.047 Uiso 1 1 calc R U . . .
C10 C 0.3746(5) 0.4221(3) 0.18314(8) 0.0382(6) Uani 1 1 d . . . . .
H10 H 0.4553 0.3195 0.1783 0.046 Uiso 1 1 calc R U . . .
C11 C 0.2108(5) 0.4697(3) 0.22821(8) 0.0347(5) Uani 1 1 d . . . . .
C12 C 0.0971(6) 0.6233(3) 0.23538(9) 0.0450(6) Uani 1 1 d . . . . .
H12 H -0.0088 0.6563 0.2663 0.054 Uiso 1 1 calc R U . . .
C13 C 0.1387(5) 0.7283(3) 0.19734(9) 0.0424(6) Uani 1 1 d . . . . .
H13 H 0.0598 0.8313 0.2023 0.051 Uiso 1 1 calc R U . . .
C14 C 0.2766(6) 0.2185(3) 0.26457(9) 0.0478(6) Uani 1 1 d . . . . .
H14A H 0.4984 0.2336 0.2651 0.057 Uiso 1 1 calc R U . . .
H14B H 0.2026 0.1479 0.2309 0.057 Uiso 1 1 calc R U . . .
C15 C 0.1814(6) 0.1414(3) 0.31364(9) 0.0494(7) Uani 1 1 d . . . . .
H15A H -0.0400 0.1215 0.3112 0.059 Uiso 1 1 calc R U . . .
H15B H 0.2686 0.0356 0.3125 0.059 Uiso 1 1 calc R U . . .
C16 C 0.2804(6) 0.2462(3) 0.36792(9) 0.0513(7) Uani 1 1 d . . . . .
H16A H 0.1871 0.3504 0.3693 0.062 Uiso 1 1 calc R U . . .
H16B H 0.5009 0.2698 0.3695 0.062 Uiso 1 1 calc R U . . .
C17 C 0.1992(6) 0.1702(3) 0.41838(9) 0.0505(7) Uani 1 1 d . . . . .
H17A H -0.0210 0.1458 0.4170 0.061 Uiso 1 1 calc R U . . .
H17B H 0.2950 0.0669 0.4176 0.061 Uiso 1 1 calc R U . . .
C18 C 0.2989(6) 0.2797(3) 0.47140(9) 0.0561(7) Uani 1 1 d . . . . .
H18A H 0.2011 0.3824 0.4718 0.067 Uiso 1 1 calc R U . . .
H18B H 0.5184 0.3057 0.4719 0.067 Uiso 1 1 calc R U . . .
C19 C 0.2302(6) 0.2115(3) 0.52346(9) 0.0543(7) Uani 1 1 d . . . . .
H19A H 0.0106 0.1874 0.5238 0.065 Uiso 1 1 calc R U . . .
H19B H 0.3267 0.1086 0.5235 0.065 Uiso 1 1 calc R U . . .
C20 C 0.3400(7) 0.3269(4) 0.57484(10) 0.0670(8) Uani 1 1 d . . . . .
H20A H 0.5588 0.3524 0.5737 0.080 Uiso 1 1 calc R U . . .
H20B H 0.2415 0.4292 0.5746 0.080 Uiso 1 1 calc R U . . .
C21 C 0.2824(8) 0.2649(4) 0.62788(11) 0.0863(10) Uani 1 1 d . . . . .
H21A H 0.0657 0.2456 0.6307 0.129 Uiso 1 1 calc R U . . .
H21B H 0.3656 0.3456 0.6580 0.129 Uiso 1 1 calc R U . . .
H21C H 0.3792 0.1639 0.6289 0.129 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 1.397(3) . ?
N1 C1 1.399(3) . ?
N1 C8 1.456(2) . ?
O1 C1 1.207(2) . ?
O2 C2 1.211(2) . ?
O3 C11 1.366(2) . ?
O3 C14 1.429(3) . ?
C1 C6 1.486(3) 2_675 ?
C2 C3 1.483(3) . ?
C3 C4 1.372(3) . ?
C3 C7 1.409(3) 2_675 ?
C4 C5 1.403(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.406(3) . ?
C6 C1 1.486(3) 2_675 ?
C7 C3 1.409(3) 2_675 ?
C7 C7 1.416(4) 2_675 ?
C8 C9 1.369(3) . ?
C8 C13 1.374(3) . ?
C9 C10 1.386(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(3) . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.511(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.510(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.520(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.503(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.511(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.506(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.500(3) . ?
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 N1 C1 124.32(17) . . ?
C2 N1 C8 118.71(17) . . ?
C1 N1 C8 116.95(17) . . ?
C11 O3 C14 117.98(16) . . ?
O1 C1 N1 120.88(18) . . ?
O1 C1 C6 122.0(2) . 2_675 ?
N1 C1 C6 117.08(19) . 2_675 ?
O2 C2 N1 121.30(18) . . ?
O2 C2 C3 121.8(2) . . ?
N1 C2 C3 116.86(19) . . ?
C4 C3 C7 119.94(18) . 2_675 ?
C4 C3 C2 120.19(19) . . ?
C7 C3 C2 119.85(19) 2_675 . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.51(18) . . ?
C5 C6 C1 120.14(19) . 2_675 ?
C7 C6 C1 119.34(19) . 2_675 ?
C6 C7 C3 121.44(18) . 2_675 ?
C6 C7 C7 119.1(2) . 2_675 ?
C3 C7 C7 119.4(2) 2_675 2_675 ?
C9 C8 C13 120.29(19) . . ?
C9 C8 N1 118.52(18) . . ?
C13 C8 N1 121.17(19) . . ?
C8 C9 C10 120.51(19) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 119.2(2) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
O3 C11 C10 124.8(2) . . ?
O3 C11 C12 115.48(18) . . ?
C10 C11 C12 119.75(18) . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C8 C13 C12 119.4(2) . . ?
C8 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
O3 C14 C15 107.45(18) . . ?
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 . . ?
C16 C15 C14 113.6(2) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 115.2(2) . . ?
C15 C16 H16A 108.5 . . ?
C17 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
C17 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C16 113.3(2) . . ?
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 . . ?
C17 C18 C19 116.4(2) . . ?
C17 C18 H18A 108.2 . . ?
C19 C18 H18A 108.2 . . ?
C17 C18 H18B 108.2 . . ?
C19 C18 H18B 108.2 . . ?
H18A C18 H18B 107.3 . . ?
C20 C19 C18 113.4(2) . . ?
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 115.8(2) . . ?
C21 C20 H20A 108.3 . . ?
C19 C20 H20A 108.3 . . ?
C21 C20 H20B 108.3 . . ?
C19 C20 H20B 108.3 . . ?
H20A C20 H20B 107.4 . . ?
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 -167.1(2) . . . . ?
C8 N1 C1 O1 11.4(3) . . . . ?
C2 N1 C1 C6 13.0(3) . . . 2_675 ?
C8 N1 C1 C6 -168.49(18) . . . 2_675 ?
C1 N1 C2 O2 169.5(2) . . . . ?
C8 N1 C2 O2 -9.0(3) . . . . ?
C1 N1 C2 C3 -11.0(3) . . . . ?
C8 N1 C2 C3 170.55(17) . . . . ?
O2 C2 C3 C4 3.7(3) . . . . ?
N1 C2 C3 C4 -175.85(19) . . . . ?
O2 C2 C3 C7 -177.6(2) . . . 2_675 ?
N1 C2 C3 C7 2.9(3) . . . 2_675 ?
C7 C3 C4 C5 -1.1(3) 2_675 . . . ?
C2 C3 C4 C5 177.73(19) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C4 C5 C6 C1 179.8(2) . . . 2_675 ?
C5 C6 C7 C3 179.7(2) . . . 2_675 ?
C1 C6 C7 C3 0.2(3) 2_675 . . 2_675 ?
C5 C6 C7 C7 -1.0(4) . . . 2_675 ?
C1 C6 C7 C7 179.5(2) 2_675 . . 2_675 ?
C2 N1 C8 C9 -109.8(2) . . . . ?
C1 N1 C8 C9 71.7(3) . . . . ?
C2 N1 C8 C13 71.8(3) . . . . ?
C1 N1 C8 C13 -106.8(2) . . . . ?
C13 C8 C9 C10 1.4(3) . . . . ?
N1 C8 C9 C10 -177.05(19) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C14 O3 C11 C10 5.0(3) . . . . ?
C14 O3 C11 C12 -175.6(2) . . . . ?
C9 C10 C11 O3 178.3(2) . . . . ?
C9 C10 C11 C12 -1.1(3) . . . . ?
O3 C11 C12 C13 -177.8(2) . . . . ?
C10 C11 C12 C13 1.6(3) . . . . ?
C9 C8 C13 C12 -1.0(3) . . . . ?
N1 C8 C13 C12 177.5(2) . . . . ?
C11 C12 C13 C8 -0.6(4) . . . . ?
C11 O3 C14 C15 177.79(18) . . . . ?
O3 C14 C15 C16 -58.2(3) . . . . ?
C14 C15 C16 C17 -177.8(2) . . . . ?
C15 C16 C17 C18 -179.3(2) . . . . ?
C16 C17 C18 C19 -179.1(2) . . . . ?
C17 C18 C19 C20 179.3(2) . . . . ?
C18 C19 C20 C21 -179.1(3) . . . . ?

_refine_diff_density_max         0.319
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_scd1625_NonNDI_T200K_orange
_database_code_depnum_ccdc_archive 'CCDC 1857162'
#Added by publCIF



_audit_update_record             
;
2018-07-20 deposited with the CCDC.
2018-08-03 downloaded from the CCDC.
;
_publcif_datablock.id            {7317a522-28c8-42c2-a7c7-c7814ef44e0d}

_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                   4.2348(19)
_cell_length_b                   51.591(19)
_cell_length_c                   8.261(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.622(11)
_cell_angle_gamma                90
_cell_volume                     1801.1(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4923
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      26.60

_exptl_crystal_description       fragment
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_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    0.086
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5789
_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      200(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            25071
_diffrn_reflns_av_unetI/netI     0.0965
_diffrn_reflns_av_R_equivalents  0.1141
_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         2.502
_diffrn_reflns_theta_max         27.587
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4162
_reflns_number_gt                2442
_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)+(0.0473P)²+1.4208P] 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       0.0050(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4162
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1554
_refine_ls_R_factor_gt           0.0837
_refine_ls_wR_factor_ref         0.1628
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_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 0.0276(7) 0.44202(5) 0.1181(3) 0.0232(7) Uani 1 1 d . . . . .
C2 C 0.3672(7) 0.47169(5) 0.2897(3) 0.0239(7) Uani 1 1 d . . . . .
C3 C 0.2622(7) 0.49379(5) 0.1851(3) 0.0209(6) Uani 1 1 d . . . . .
C4 C 0.0482(7) 0.48942(5) 0.0502(3) 0.0204(6) Uani 1 1 d . . . . .
C5 C 0.3706(7) 0.51834(5) 0.2205(3) 0.0253(7) Uani 1 1 d . . . . .
H5 H 0.5136 0.5211 0.3121 0.030 Uiso 1 1 calc R U . . .
C6 C 0.2713(7) 0.53936(5) 0.1221(3) 0.0246(7) Uani 1 1 d . . . . .
H6 H 0.3458 0.5563 0.1484 0.029 Uiso 1 1 calc R U . . .
C7 C 0.0666(7) 0.53563(5) -0.0124(3) 0.0202(6) Uani 1 1 d . . . . .
C8 C 0.2746(7) 0.42751(5) 0.3808(3) 0.0238(7) Uani 1 1 d . . . . .
C9 C 0.1503(7) 0.43095(5) 0.5294(3) 0.0258(7) Uani 1 1 d . . . . .
H9 H 0.0237 0.4457 0.5484 0.031 Uiso 1 1 calc R U . . .
C10 C 0.2110(7) 0.41269(5) 0.6521(3) 0.0238(7) Uani 1 1 d . . . . .
H10 H 0.1289 0.4151 0.7554 0.029 Uiso 1 1 calc R U . . .
C11 C 0.3910(7) 0.39116(5) 0.6220(3) 0.0236(7) Uani 1 1 d . . . . .
C12 C 0.5054(7) 0.38749(5) 0.4695(3) 0.0276(7) Uani 1 1 d . . . . .
H12 H 0.6232 0.3723 0.4481 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4490(7) 0.40569(5) 0.3494(3) 0.0264(7) Uani 1 1 d . . . . .
H13 H 0.5294 0.4033 0.2457 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3386(8) 0.37397(5) 0.8889(3) 0.0279(7) Uani 1 1 d . . . . .
H14A H 0.1047 0.3742 0.8750 0.033 Uiso 1 1 calc R U . . .
H14B H 0.4096 0.3901 0.9450 0.033 Uiso 1 1 calc R U . . .
C15 C 0.4491(8) 0.35055(5) 0.9875(3) 0.0293(7) Uani 1 1 d . . . . .
H15A H 0.3513 0.3510 1.0932 0.035 Uiso 1 1 calc R U . . .
H15B H 0.6813 0.3516 1.0093 0.035 Uiso 1 1 calc R U . . .
C16 C 0.3680(8) 0.32489(5) 0.9044(3) 0.0294(7) Uani 1 1 d . . . . .
H16A H 0.4720 0.3242 0.8005 0.035 Uiso 1 1 calc R U . . .
H16B H 0.1366 0.3242 0.8789 0.035 Uiso 1 1 calc R U . . .
C17 C 0.4671(8) 0.30107(5) 1.0044(3) 0.0284(7) Uani 1 1 d . . . . .
H17A H 0.6974 0.3020 1.0331 0.034 Uiso 1 1 calc R U . . .
H17B H 0.3570 0.3013 1.1066 0.034 Uiso 1 1 calc R U . . .
C18 C 0.3933(8) 0.27569(5) 0.9160(3) 0.0293(7) Uani 1 1 d . . . . .
H18A H 0.1630 0.2749 0.8872 0.035 Uiso 1 1 calc R U . . .
H18B H 0.5028 0.2756 0.8137 0.035 Uiso 1 1 calc R U . . .
C19 C 0.4894(8) 0.25151(5) 1.0123(3) 0.0305(7) Uani 1 1 d . . . . .
H19A H 0.7195 0.2522 1.0416 0.037 Uiso 1 1 calc R U . . .
H19B H 0.3787 0.2514 1.1144 0.037 Uiso 1 1 calc R U . . .
C20 C 0.4151(8) 0.22644(5) 0.9216(3) 0.0304(7) Uani 1 1 d . . . . .
H20A H 0.5230 0.2266 0.8187 0.037 Uiso 1 1 calc R U . . .
H20B H 0.1844 0.2255 0.8939 0.037 Uiso 1 1 calc R U . . .
C21 C 0.5165(8) 0.20235(5) 1.0175(4) 0.0340(8) Uani 1 1 d . . . . .
H21A H 0.7472 0.2033 1.0448 0.041 Uiso 1 1 calc R U . . .
H21B H 0.4095 0.2023 1.1207 0.041 Uiso 1 1 calc R U . . .
C22 C 0.4429(9) 0.17706(6) 0.9292(4) 0.0479(10) Uani 1 1 d . . . . .
H22A H 0.2136 0.1754 0.9078 0.072 Uiso 1 1 calc R U . . .
H22B H 0.5218 0.1625 0.9965 0.072 Uiso 1 1 calc R U . . .
H22C H 0.5459 0.1769 0.8262 0.072 Uiso 1 1 calc R U . . .
N1 N 0.2182(6) 0.44773(4) 0.2586(3) 0.0225(6) Uani 1 1 d . . . . .
O1 O -0.0591(5) 0.42015(3) 0.0865(2) 0.0305(5) Uani 1 1 d . . . . .
O2 O 0.5741(5) 0.47388(4) 0.3971(2) 0.0328(5) Uani 1 1 d . . . . .
O3 O 0.4720(5) 0.37228(3) 0.7339(2) 0.0297(5) 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 1.210(3) . ?
C1 N1 1.402(4) . ?
C1 C7 1.485(4) 3_565 ?
C2 O2 1.212(3) . ?
C2 N1 1.404(3) . ?
C2 C3 1.482(4) . ?
C3 C5 1.372(4) . ?
C3 C4 1.409(4) . ?
C4 C7 1.409(4) 3_565 ?
C4 C4 1.416(5) 3_565 ?
C5 C6 1.404(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.379(4) . ?
C6 H6 0.9500 . ?
C7 C4 1.409(4) 3_565 ?
C7 C1 1.485(4) 3_565 ?
C8 C9 1.377(4) . ?
C8 C13 1.380(4) . ?
C8 N1 1.461(3) . ?
C9 C10 1.396(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(4) . ?
C10 H10 0.9500 . ?
C11 O3 1.371(3) . ?
C11 C12 1.391(4) . ?
C12 C13 1.376(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O3 1.435(3) . ?
C14 C15 1.515(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.520(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.525(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.522(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.521(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.518(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.521(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.517(4) . ?
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 121.7(2) . . ?
O1 C1 C7 122.0(3) . 3_565 ?
N1 C1 C7 116.3(2) . 3_565 ?
O2 C2 N1 120.8(2) . . ?
O2 C2 C3 122.1(3) . . ?
N1 C2 C3 117.1(2) . . ?
C5 C3 C4 120.4(2) . . ?
C5 C3 C2 120.1(3) . . ?
C4 C3 C2 119.5(2) . . ?
C7 C4 C3 121.2(2) 3_565 . ?
C7 C4 C4 119.7(3) 3_565 3_565 ?
C3 C4 C4 119.1(3) . 3_565 ?
C3 C5 C6 120.4(3) . . ?
C3 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C4 119.8(2) . 3_565 ?
C6 C7 C1 119.8(2) . 3_565 ?
C4 C7 C1 120.4(2) 3_565 3_565 ?
C9 C8 C13 120.8(3) . . ?
C9 C8 N1 118.0(2) . . ?
C13 C8 N1 121.2(2) . . ?
C8 C9 C10 119.8(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 119.5(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
O3 C11 C10 124.7(2) . . ?
O3 C11 C12 115.3(2) . . ?
C10 C11 C12 120.1(2) . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C8 119.5(3) . . ?
C12 C13 H13 120.3 . . ?
C8 C13 H13 120.3 . . ?
O3 C14 C15 107.8(2) . . ?
O3 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
O3 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 C16 113.5(2) . . ?
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 114.2(2) . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C18 C17 C16 113.1(2) . . ?
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 114.5(2) . . ?
C19 C18 H18A 108.6 . . ?
C17 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C17 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C18 113.6(2) . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C18 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 C21 113.3(2) . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C22 C21 C20 114.2(3) . . ?
C22 C21 H21A 108.7 . . ?
C20 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
C20 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
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 124.4(2) . . ?
C1 N1 C8 118.8(2) . . ?
C2 N1 C8 116.8(2) . . ?
C11 O3 C14 117.6(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
O2 C2 C3 C5 -8.1(4) . . . . ?
N1 C2 C3 C5 172.4(3) . . . . ?
O2 C2 C3 C4 172.5(3) . . . . ?
N1 C2 C3 C4 -7.0(4) . . . . ?
C5 C3 C4 C7 -179.7(3) . . . 3_565 ?
C2 C3 C4 C7 -0.4(4) . . . 3_565 ?
C5 C3 C4 C4 1.3(5) . . . 3_565 ?
C2 C3 C4 C4 -179.3(3) . . . 3_565 ?
C4 C3 C5 C6 -0.5(4) . . . . ?
C2 C3 C5 C6 -179.8(3) . . . . ?
C3 C5 C6 C7 -0.7(4) . . . . ?
C5 C6 C7 C4 1.0(4) . . . 3_565 ?
C5 C6 C7 C1 -178.0(3) . . . 3_565 ?
C13 C8 C9 C10 2.5(4) . . . . ?
N1 C8 C9 C10 -177.0(3) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
C9 C10 C11 O3 178.4(3) . . . . ?
C9 C10 C11 C12 -1.3(4) . . . . ?
O3 C11 C12 C13 -177.6(3) . . . . ?
C10 C11 C12 C13 2.2(4) . . . . ?
C11 C12 C13 C8 -0.7(4) . . . . ?
C9 C8 C13 C12 -1.6(4) . . . . ?
N1 C8 C13 C12 177.9(3) . . . . ?
O3 C14 C15 C16 -56.1(3) . . . . ?
C14 C15 C16 C17 -178.0(3) . . . . ?
C15 C16 C17 C18 -178.0(3) . . . . ?
C16 C17 C18 C19 180.0(3) . . . . ?
C17 C18 C19 C20 -179.7(3) . . . . ?
C18 C19 C20 C21 179.1(3) . . . . ?
C19 C20 C21 C22 179.7(3) . . . . ?
O1 C1 N1 C2 169.5(3) . . . . ?
C7 C1 N1 C2 -11.7(4) 3_565 . . . ?
O1 C1 N1 C8 -9.0(4) . . . . ?
C7 C1 N1 C8 169.8(2) 3_565 . . . ?
O2 C2 N1 C1 -166.0(3) . . . . ?
C3 C2 N1 C1 13.5(4) . . . . ?
O2 C2 N1 C8 12.6(4) . . . . ?
C3 C2 N1 C8 -167.9(2) . . . . ?
C9 C8 N1 C1 -113.3(3) . . . . ?
C13 C8 N1 C1 67.2(4) . . . . ?
C9 C8 N1 C2 68.0(3) . . . . ?
C13 C8 N1 C2 -111.5(3) . . . . ?
C10 C11 O3 C14 5.3(4) . . . . ?
C12 C11 O3 C14 -174.9(3) . . . . ?
C15 C14 O3 C11 177.4(2) . . . . ?

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.060

