# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_cyg180s
_database_code_depnum_ccdc_archive 'CCDC 1560178'
_audit_update_record             
;
2017-07-04 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 N2 O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         444.47

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.234(4)
_cell_length_b                   11.140(3)
_cell_length_c                   15.953(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.502(9)
_cell_angle_gamma                90
_cell_volume                     2217.0(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4840
_cell_measurement_theta_min      2.2752
_cell_measurement_theta_max      28.9954
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.400
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936

_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            32941
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         31.15
_diffrn_reflns_theta_full        31.15
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23

_refine_special_details          
;
;

_reflns_number_total             7124
_reflns_number_gt                4497
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1451
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_number_reflns         7124
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0584P)²+0.9405P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.18763(14) 0.42938(15) 0.37307(10) 0.0199(3) Uani d . . . 1 . .
H H1 0.1219 0.3864 0.3556 0.024 Uiso calc U . R 1 . .
C C2 0.24420(14) 0.44365(15) 0.31458(10) 0.0220(4) Uani d . . . 1 . .
H H2 0.2172 0.4101 0.2566 0.026 Uiso calc U . R 1 . .
C C3 0.33997(14) 0.50667(15) 0.34029(10) 0.0202(3) Uani d . . . 1 . .
H H3 0.3779 0.5158 0.2996 0.024 Uiso calc U . R 1 . .
C C4 0.38144(13) 0.55680(14) 0.42488(10) 0.0167(3) Uani d . . . 1 . .
H H4 0.4473 0.5996 0.4422 0.02 Uiso calc U . R 1 . .
C C5 0.32450(12) 0.54299(13) 0.48344(9) 0.0138(3) Uani d . . . 1 . .
C C6 0.22883(12) 0.47909(14) 0.45771(9) 0.0152(3) Uani d . . . 1 . .
C C7 0.18077(12) 0.47659(14) 0.53111(10) 0.0154(3) Uani d . . . 1 . .
H H7 0.1255 0.5415 0.5181 0.019 Uiso calc U . R 1 . .
C C8 0.12535(13) 0.35993(14) 0.54040(10) 0.0179(3) Uani d . . . 1 . .
H H8A 0.0748 0.3363 0.4815 0.022 Uiso calc U . R 1 . .
H H8B 0.1797 0.2956 0.5609 0.022 Uiso calc U . R 1 . .
C C9 0.06469(12) 0.37154(15) 0.60549(10) 0.0184(3) Uani d . . . 1 . .
C C10 0.01611(13) 0.26169(15) 0.63013(10) 0.0199(3) Uani d . . . 1 . .
C C11 -0.04769(14) 0.27545(18) 0.68393(11) 0.0255(4) Uani d . . . 1 . .
H H11 -0.057 0.3526 0.7057 0.031 Uiso calc U . R 1 . .
C C12 -0.09720(15) 0.17623(19) 0.70528(12) 0.0320(4) Uani d . . . 1 . .
H H12 -0.14 0.1855 0.7423 0.038 Uiso calc U . R 1 . .
C C13 -0.08507(16) 0.06390(19) 0.67337(13) 0.0342(5) Uani d . . . 1 . .
H H13 -0.1202 -0.0034 0.6878 0.041 Uiso calc U . R 1 . .
C C14 -0.02197(16) 0.04941(18) 0.62048(13) 0.0321(4) Uani d . . . 1 . .
H H14 -0.0135 -0.0279 0.5986 0.039 Uiso calc U . R 1 . .
C C15 0.02910(14) 0.14792(16) 0.59923(12) 0.0250(4) Uani d . . . 1 . .
H H15 0.0731 0.1376 0.5634 0.03 Uiso calc U . R 1 . .
C C16 0.27555(12) 0.51667(14) 0.61400(9) 0.0146(3) Uani d . . . 1 . .
H H16 0.2491 0.5697 0.6528 0.018 Uiso calc U . R 1 . .
C C17 0.35433(12) 0.58614(13) 0.57889(9) 0.0130(3) Uani d . . . 1 . .
H H17 0.4288 0.5586 0.6123 0.016 Uiso calc U . R 1 . .
C C18 0.34824(12) 0.72531(13) 0.59211(9) 0.0144(3) Uani d . . . 1 . .
C C19 0.38928(14) 0.75362(15) 0.69213(10) 0.0208(3) Uani d . . . 1 . .
H H19A 0.3979 0.8406 0.7008 0.031 Uiso calc U . R 1 . .
H H19B 0.4586 0.7141 0.7201 0.031 Uiso calc U . R 1 . .
H H19C 0.3376 0.7242 0.7193 0.031 Uiso calc U . R 1 . .
C C20 0.23347(13) 0.77172(15) 0.55262(11) 0.0204(3) Uani d . . . 1 . .
H H20A 0.1898 0.7384 0.586 0.031 Uiso calc U . R 1 . .
H H20B 0.2035 0.747 0.4902 0.031 Uiso calc U . R 1 . .
H H20C 0.2334 0.8595 0.5563 0.031 Uiso calc U . R 1 . .
C C21 0.42206(12) 0.78315(13) 0.54753(9) 0.0143(3) Uani d . . . 1 . .
C C22 0.53269(13) 0.76935(14) 0.58559(10) 0.0181(3) Uani d . . . 1 . .
H H22 0.5612 0.7314 0.6419 0.022 Uiso calc U . R 1 . .
C C23 0.60180(14) 0.80975(15) 0.54303(12) 0.0224(3) Uani d . . . 1 . .
H H23 0.677 0.7992 0.5693 0.027 Uiso calc U . R 1 . .
C C24 0.55927(15) 0.86554(14) 0.46173(11) 0.0222(4) Uani d . . . 1 . .
C C25 0.45070(15) 0.88431(14) 0.42272(11) 0.0221(4) Uani d . . . 1 . .
H H25 0.4231 0.9247 0.3673 0.027 Uiso calc U . R 1 . .
C C26 0.38265(14) 0.84294(14) 0.46612(10) 0.0182(3) Uani d . . . 1 . .
H H26 0.3076 0.8555 0.44 0.022 Uiso calc U . R 1 . .
N N1 0.32854(11) 0.40636(12) 0.66462(9) 0.0185(3) Uani d . . . 1 . .
N N2 0.63169(15) 0.90629(13) 0.41537(12) 0.0320(4) Uani d . . . 1 . .
O O1 0.05153(10) 0.47004(11) 0.63367(8) 0.0246(3) Uani d . . . 1 . .
O O2 0.30131(11) 0.37537(14) 0.72742(9) 0.0376(4) Uani d . . . 1 . .
O O3 0.39159(10) 0.35028(10) 0.63862(8) 0.0256(3) Uani d . . . 1 . .
O O4 0.72892(13) 0.89956(13) 0.45475(12) 0.0425(4) Uani d . . . 1 . .
O O5 0.59186(14) 0.94553(13) 0.33978(10) 0.0439(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.387(2) ?
C1 C6 . 1.391(2) ?
C2 C3 . 1.386(2) ?
C3 C4 . 1.393(2) ?
C4 C5 . 1.391(2) ?
C5 C6 . 1.390(2) ?
C5 C17 . 1.518(2) ?
C6 C7 . 1.508(2) ?
C7 C8 . 1.524(2) ?
C7 C16 . 1.554(2) ?
C8 C9 . 1.515(2) ?
C9 O1 . 1.220(2) ?
C9 C10 . 1.495(2) ?
C10 C15 . 1.391(2) ?
C10 C11 . 1.399(2) ?
C11 C12 . 1.384(3) ?
C12 C13 . 1.380(3) ?
C13 C14 . 1.381(3) ?
C14 C15 . 1.389(3) ?
C16 N1 . 1.509(2) ?
C16 C17 . 1.546(2) ?
C17 C18 . 1.570(2) ?
C18 C20 . 1.527(2) ?
C18 C21 . 1.529(2) ?
C18 C19 . 1.537(2) ?
C21 C22 . 1.394(2) ?
C21 C26 . 1.396(2) ?
C22 C23 . 1.384(2) ?
C23 C24 . 1.378(2) ?
C24 C25 . 1.378(3) ?
C24 N2 . 1.465(2) ?
C25 C26 . 1.385(2) ?
N1 O3 . 1.2204(18) ?
N1 O2 . 1.2223(18) ?
N2 O5 . 1.224(2) ?
N2 O4 . 1.231(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 118.87(15) ?
C3 C2 C1 . . 120.32(14) ?
C2 C3 C4 . . 121.03(15) ?
C5 C4 C3 . . 118.68(15) ?
C6 C5 C4 . . 120.18(13) ?
C6 C5 C17 . . 111.38(13) ?
C4 C5 C17 . . 128.40(14) ?
C5 C6 C1 . . 120.91(14) ?
C5 C6 C7 . . 111.04(13) ?
C1 C6 C7 . . 128.04(15) ?
C6 C7 C8 . . 115.64(13) ?
C6 C7 C16 . . 103.04(12) ?
C8 C7 C16 . . 116.13(12) ?
C9 C8 C7 . . 112.10(13) ?
O1 C9 C10 . . 120.83(15) ?
O1 C9 C8 . . 120.18(15) ?
C10 C9 C8 . . 118.90(14) ?
C15 C10 C11 . . 119.25(16) ?
C15 C10 C9 . . 122.53(15) ?
C11 C10 C9 . . 118.19(16) ?
C12 C11 C10 . . 119.72(18) ?
C13 C12 C11 . . 120.68(18) ?
C12 C13 C14 . . 120.00(18) ?
C13 C14 C15 . . 119.98(19) ?
C14 C15 C10 . . 120.37(18) ?
N1 C16 C17 . . 110.64(12) ?
N1 C16 C7 . . 108.69(12) ?
C17 C16 C7 . . 106.62(11) ?
C5 C17 C16 . . 102.94(12) ?
C5 C17 C18 . . 116.08(12) ?
C16 C17 C18 . . 112.00(12) ?
C20 C18 C21 . . 111.55(13) ?
C20 C18 C19 . . 108.47(13) ?
C21 C18 C19 . . 109.70(13) ?
C20 C18 C17 . . 111.55(12) ?
C21 C18 C17 . . 106.51(12) ?
C19 C18 C17 . . 109.02(12) ?
C22 C21 C26 . . 118.01(14) ?
C22 C21 C18 . . 119.48(13) ?
C26 C21 C18 . . 122.35(14) ?
C23 C22 C21 . . 121.38(15) ?
C24 C23 C22 . . 118.65(16) ?
C23 C24 C25 . . 122.04(15) ?
C23 C24 N2 . . 118.99(17) ?
C25 C24 N2 . . 118.97(16) ?
C24 C25 C26 . . 118.52(15) ?
C25 C26 C21 . . 121.35(16) ?
O3 N1 O2 . . 123.79(15) ?
O3 N1 C16 . . 118.91(13) ?
O2 N1 C16 . . 117.21(14) ?
O5 N2 O4 . . 123.87(17) ?
O5 N2 C24 . . 117.96(18) ?
O4 N2 C24 . . 118.17(17) ?

