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

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

data_20
_database_code_depnum_ccdc_archive 'CCDC 1840054'
_audit_update_record             
;
2018-04-27 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_audit_creation_date             2017-08-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H32 N2 O6'
_chemical_formula_sum            'C21 H32 N2 O6'
_chemical_formula_weight         408.48
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           77
_space_group_name_H-M_alt        'P 42'
_space_group_name_Hall           'P 4c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x, z+1/2'
'-x, -y, z'
'y, -x, z+1/2'

_cell_length_a                   27.1192(8)
_cell_length_b                   27.1192(8)
_cell_length_c                   6.0742(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4467.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4582
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.10
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0740 before and 0.0628 after correction. The Ratio of minimum to maximum transmission is 0.8639. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.618
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.166
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            37067
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         0.751
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                7128
_reflns_number_total             8969
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         8969
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0349P)²+0.0256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0889
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C28(H28), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C27(H27A,H27B),
 C29(H29A,H29B), C31(H31A,H31B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C34(H34), C35(H35), C36(H36)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C19(H19A,H19B,H19C),
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C42(H42A,
 H42B,H42C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.40405(8) 0.71308(8) 0.5006(4) 0.0311(6) Uani 1 1 d . . . . .
O2 O 0.37799(7) 0.64384(8) 0.3223(3) 0.0261(5) Uani 1 1 d . . . . .
O3 O 0.54148(9) 0.59829(8) -0.2071(4) 0.0289(5) Uani 1 1 d . . . . .
O4 O 0.64101(8) 0.81969(7) 0.1676(3) 0.0247(5) Uani 1 1 d . . . . .
O5 O 0.58526(8) 0.87952(8) 0.2385(3) 0.0289(5) Uani 1 1 d . . . . .
O6 O 0.64380(7) 0.88544(7) -0.0273(3) 0.0252(5) Uani 1 1 d . . . . .
N1 N 0.44815(9) 0.68367(9) 0.2183(4) 0.0277(6) Uani 1 1 d . . . . .
N2 N 0.58685(9) 0.75917(9) 0.2809(4) 0.0192(6) Uani 1 1 d . . . . .
C1 C 0.35647(11) 0.72523(12) 0.6037(5) 0.0260(7) Uani 1 1 d . . . . .
C2 C 0.33699(14) 0.68321(13) 0.7407(6) 0.0385(9) Uani 1 1 d . . . . .
H2A H 0.327148 0.656016 0.643963 0.058 Uiso 1 1 calc GR . . . .
H2B H 0.308376 0.694425 0.825575 0.058 Uiso 1 1 calc GR . . . .
H2C H 0.362778 0.671850 0.841726 0.058 Uiso 1 1 calc GR . . . .
C3 C 0.32100(14) 0.74116(15) 0.4270(6) 0.0468(10) Uani 1 1 d . . . . .
H3A H 0.335980 0.767471 0.338958 0.070 Uiso 1 1 calc GR . . . .
H3B H 0.290607 0.753358 0.495182 0.070 Uiso 1 1 calc GR . . . .
H3C H 0.313314 0.713010 0.331826 0.070 Uiso 1 1 calc GR . . . .
C4 C 0.37017(14) 0.76821(13) 0.7528(7) 0.0463(10) Uani 1 1 d . . . . .
H4A H 0.395664 0.757679 0.857052 0.069 Uiso 1 1 calc GR . . . .
H4B H 0.340921 0.779109 0.834171 0.069 Uiso 1 1 calc GR . . . .
H4C H 0.382737 0.795526 0.663328 0.069 Uiso 1 1 calc GR . . . .
C5 C 0.40757(11) 0.67742(12) 0.3456(5) 0.0244(7) Uani 1 1 d . . . . .
C6 C 0.46402(11) 0.64463(11) 0.0675(5) 0.0251(7) Uani 1 1 d . . . . .
H6A H 0.473544 0.659426 -0.075342 0.030 Uiso 1 1 calc R . . . .
H6B H 0.436201 0.621760 0.040688 0.030 Uiso 1 1 calc R . . . .
C7 C 0.50748(11) 0.61598(11) 0.1609(5) 0.0216(7) Uani 1 1 d . . . . .
H7 H 0.495813 0.598275 0.295573 0.026 Uiso 1 1 calc R . . . .
C8 C 0.54894(11) 0.65099(10) 0.2301(5) 0.0203(7) Uani 1 1 d . . . . .
H8A H 0.564129 0.665551 0.096954 0.024 Uiso 1 1 calc R . . . .
H8B H 0.574699 0.632027 0.308656 0.024 Uiso 1 1 calc R . . . .
C9 C 0.53028(12) 0.69260(11) 0.3801(5) 0.0239(7) Uani 1 1 d . . . . .
H9 H 0.517669 0.677351 0.518961 0.029 Uiso 1 1 calc R . . . .
C10 C 0.48728(11) 0.71920(11) 0.2682(6) 0.0262(8) Uani 1 1 d . . . . .
H10A H 0.474364 0.745272 0.366583 0.031 Uiso 1 1 calc R . . . .
H10B H 0.498810 0.734978 0.130523 0.031 Uiso 1 1 calc R . . . .
C11 C 0.52541(12) 0.57728(11) -0.0034(5) 0.0267(7) Uani 1 1 d . . . . .
H11A H 0.553023 0.558613 0.063048 0.032 Uiso 1 1 calc R . . . .
H11B H 0.498315 0.553727 -0.033025 0.032 Uiso 1 1 calc R . . . .
C12 C 0.57048(11) 0.72858(11) 0.4406(5) 0.0209(7) Uani 1 1 d . . . . .
C13 C 0.58956(13) 0.72977(12) 0.6519(5) 0.0296(8) Uani 1 1 d . . . . .
H13 H 0.577581 0.707658 0.760784 0.036 Uiso 1 1 calc R . . . .
C14 C 0.62613(14) 0.76332(13) 0.7035(5) 0.0368(9) Uani 1 1 d . . . . .
H14 H 0.639647 0.764440 0.847671 0.044 Uiso 1 1 calc R . . . .
C15 C 0.64262(12) 0.79496(12) 0.5437(5) 0.0307(8) Uani 1 1 d . . . . .
H15 H 0.667474 0.818757 0.572839 0.037 Uiso 1 1 calc R . . . .
C16 C 0.62144(11) 0.79055(11) 0.3393(5) 0.0213(7) Uani 1 1 d . . . . .
C17 C 0.61932(11) 0.86450(11) 0.1352(5) 0.0216(7) Uani 1 1 d . . . . .
C18 C 0.63061(12) 0.93621(11) -0.1007(5) 0.0253(7) Uani 1 1 d . . . . .
C19 C 0.63556(13) 0.97200(12) 0.0882(5) 0.0330(8) Uani 1 1 d . . . . .
H19A H 0.610000 0.965169 0.198100 0.050 Uiso 1 1 calc GR . . . .
H19B H 0.631735 1.005771 0.033367 0.050 Uiso 1 1 calc GR . . . .
H19C H 0.668162 0.968316 0.155842 0.050 Uiso 1 1 calc GR . . . .
C20 C 0.67008(12) 0.94563(12) -0.2729(5) 0.0311(8) Uani 1 1 d . . . . .
H20A H 0.702634 0.945038 -0.202895 0.047 Uiso 1 1 calc GR . . . .
H20B H 0.664607 0.977955 -0.340703 0.047 Uiso 1 1 calc GR . . . .
H20C H 0.668474 0.919962 -0.386252 0.047 Uiso 1 1 calc GR . . . .
C21 C 0.58006(12) 0.93588(14) -0.2056(6) 0.0347(8) Uani 1 1 d . . . . .
H21A H 0.579220 0.911241 -0.323539 0.052 Uiso 1 1 calc GR . . . .
H21B H 0.572965 0.968537 -0.266998 0.052 Uiso 1 1 calc GR . . . .
H21C H 0.555238 0.927660 -0.094247 0.052 Uiso 1 1 calc GR . . . .
O7 O 0.80754(7) 0.87309(7) 0.6702(3) 0.0237(5) Uani 1 1 d . . . . .
O8 O 0.87963(7) 0.85763(7) 0.4899(3) 0.0221(5) Uani 1 1 d . . . . .
O9 O 0.89994(8) 1.02516(8) -0.0253(3) 0.0214(5) Uani 1 1 d . . . . .
O10 O 0.67373(7) 1.09945(8) 0.4368(3) 0.0225(5) Uani 1 1 d . . . . .
O11 O 0.60659(8) 1.06451(9) 0.5957(4) 0.0339(6) Uani 1 1 d . . . . .
O12 O 0.60299(7) 1.11473(8) 0.2970(3) 0.0253(5) Uani 1 1 d . . . . .
N3 N 0.82871(9) 0.92010(9) 0.3839(4) 0.0185(6) Uani 1 1 d . . . . .
N4 N 0.73909(8) 1.04993(9) 0.5170(4) 0.0166(5) Uani 1 1 d . . . . .
C22 C 0.80260(10) 0.82393(10) 0.7733(5) 0.0192(6) Uani 1 1 d . . . . .
C23 C 0.79296(13) 0.78642(12) 0.5915(6) 0.0307(8) Uani 1 1 d . . . . .
H23A H 0.764604 0.797048 0.503462 0.046 Uiso 1 1 calc GR . . . .
H23B H 0.785981 0.754169 0.657262 0.046 Uiso 1 1 calc GR . . . .
H23C H 0.822114 0.783909 0.496773 0.046 Uiso 1 1 calc GR . . . .
C24 C 0.84736(12) 0.81108(12) 0.9098(5) 0.0303(8) Uani 1 1 d . . . . .
H24A H 0.875760 0.806014 0.812623 0.045 Uiso 1 1 calc GR . . . .
H24B H 0.840919 0.780801 0.993027 0.045 Uiso 1 1 calc GR . . . .
H24C H 0.854428 0.838084 1.012226 0.045 Uiso 1 1 calc GR . . . .
C25 C 0.75790(11) 0.83136(12) 0.9198(5) 0.0249(7) Uani 1 1 d . . . . .
H25A H 0.765136 0.856813 1.029678 0.037 Uiso 1 1 calc GR . . . .
H25B H 0.749950 0.800337 0.994469 0.037 Uiso 1 1 calc GR . . . .
H25C H 0.729759 0.841746 0.829824 0.037 Uiso 1 1 calc GR . . . .
C26 C 0.84189(11) 0.88174(11) 0.5142(5) 0.0189(7) Uani 1 1 d . . . . .
C27 C 0.86534(10) 0.94250(10) 0.2372(5) 0.0185(7) Uani 1 1 d . . . . .
H27A H 0.849345 0.951639 0.096455 0.022 Uiso 1 1 calc R . . . .
H27B H 0.891553 0.918163 0.204592 0.022 Uiso 1 1 calc R . . . .
C28 C 0.88840(10) 0.98842(10) 0.3411(5) 0.0155(6) Uani 1 1 d . . . . .
H28 H 0.908496 0.977258 0.469817 0.019 Uiso 1 1 calc R . . . .
C29 C 0.84908(10) 1.02378(10) 0.4283(5) 0.0161(6) Uani 1 1 d . . . . .
H29A H 0.831996 1.039498 0.302485 0.019 Uiso 1 1 calc R . . . .
H29B H 0.865204 1.050119 0.515166 0.019 Uiso 1 1 calc R . . . .
C30 C 0.81106(10) 0.99736(10) 0.5729(4) 0.0165(6) Uani 1 1 d . . . . .
H30 H 0.829127 0.983205 0.701759 0.020 Uiso 1 1 calc R . . . .
C31 C 0.78900(10) 0.95436(10) 0.4447(5) 0.0181(6) Uani 1 1 d . . . . .
H31A H 0.764214 0.937134 0.536383 0.022 Uiso 1 1 calc R . . . .
H31B H 0.772395 0.966720 0.310481 0.022 Uiso 1 1 calc R . . . .
C32 C 0.92356(10) 1.01273(11) 0.1776(5) 0.0201(7) Uani 1 1 d . . . . .
H32A H 0.937329 1.043036 0.244452 0.024 Uiso 1 1 calc R . . . .
H32B H 0.951311 0.990008 0.147226 0.024 Uiso 1 1 calc R . . . .
C33 C 0.77200(10) 1.03153(10) 0.6622(4) 0.0152(6) Uani 1 1 d . . . . .
C34 C 0.76987(11) 1.04262(11) 0.8836(5) 0.0190(7) Uani 1 1 d . . . . .
H34 H 0.793443 1.029089 0.982264 0.023 Uiso 1 1 calc R . . . .
C35 C 0.73315(11) 1.07360(11) 0.9613(5) 0.0218(7) Uani 1 1 d . . . . .
H35 H 0.731327 1.081471 1.113503 0.026 Uiso 1 1 calc R . . . .
C36 C 0.69941(11) 1.09280(11) 0.8161(5) 0.0206(7) Uani 1 1 d . . . . .
H36 H 0.673771 1.114240 0.862856 0.025 Uiso 1 1 calc R . . . .
C37 C 0.70480(11) 1.07927(11) 0.5988(5) 0.0176(6) Uani 1 1 d . . . . .
C38 C 0.62447(11) 1.09006(11) 0.4582(5) 0.0208(7) Uani 1 1 d . . . . .
C39 C 0.54806(11) 1.11387(12) 0.2763(5) 0.0243(7) Uani 1 1 d . . . . .
C40 C 0.54053(13) 1.14757(14) 0.0801(5) 0.0355(9) Uani 1 1 d . . . . .
H40A H 0.554496 1.180105 0.112357 0.053 Uiso 1 1 calc GR . . . .
H40B H 0.505176 1.150866 0.050020 0.053 Uiso 1 1 calc GR . . . .
H40C H 0.557038 1.133530 -0.049025 0.053 Uiso 1 1 calc GR . . . .
C41 C 0.53071(14) 1.06185(13) 0.2298(7) 0.0446(10) Uani 1 1 d . . . . .
H41A H 0.545885 1.049988 0.093326 0.067 Uiso 1 1 calc GR . . . .
H41B H 0.494746 1.061634 0.214076 0.067 Uiso 1 1 calc GR . . . .
H41C H 0.540261 1.040262 0.351971 0.067 Uiso 1 1 calc GR . . . .
C42 C 0.52488(11) 1.13527(12) 0.4810(5) 0.0281(8) Uani 1 1 d . . . . .
H42A H 0.527654 1.111537 0.601989 0.042 Uiso 1 1 calc GR . . . .
H42B H 0.490006 1.142324 0.452771 0.042 Uiso 1 1 calc GR . . . .
H42C H 0.541925 1.165846 0.520987 0.042 Uiso 1 1 calc GR . . . .
H9A H 0.8873(13) 1.0526(13) -0.018(6) 0.038(11) Uiso 1 1 d . . . . .
H3 H 0.5726(14) 0.6060(13) -0.200(6) 0.046(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.471(4) . ?
O1 C5 1.353(4) . ?
O2 C5 1.222(4) . ?
O3 C11 1.430(4) . ?
O4 C16 1.412(3) . ?
O4 C17 1.364(4) . ?
O5 C17 1.189(3) . ?
O6 C17 1.318(4) . ?
O6 C18 1.491(4) . ?
N1 C5 1.356(4) . ?
N1 C6 1.465(4) . ?
N1 C10 1.465(4) . ?
N2 C12 1.351(4) . ?
N2 C16 1.315(4) . ?
C1 C2 1.507(4) . ?
C1 C3 1.504(5) . ?
C1 C4 1.522(5) . ?
C6 C7 1.521(4) . ?
C7 C8 1.531(4) . ?
C7 C11 1.528(4) . ?
C8 C9 1.536(4) . ?
C9 C10 1.530(4) . ?
C9 C12 1.509(4) . ?
C12 C13 1.384(4) . ?
C13 C14 1.382(5) . ?
C14 C15 1.371(5) . ?
C15 C16 1.373(4) . ?
C18 C19 1.509(4) . ?
C18 C20 1.518(4) . ?
C18 C21 1.512(4) . ?
O7 C22 1.479(3) . ?
O7 C26 1.349(3) . ?
O8 C26 1.224(3) . ?
O9 C32 1.429(3) . ?
O10 C37 1.406(3) . ?
O10 C38 1.366(3) . ?
O11 C38 1.189(4) . ?
O12 C38 1.322(3) . ?
O12 C39 1.495(3) . ?
N3 C26 1.355(4) . ?
N3 C27 1.467(3) . ?
N3 C31 1.470(3) . ?
N4 C33 1.350(3) . ?
N4 C37 1.321(4) . ?
C22 C23 1.524(4) . ?
C22 C24 1.511(4) . ?
C22 C25 1.517(4) . ?
C27 C28 1.530(4) . ?
C28 C29 1.529(4) . ?
C28 C32 1.527(4) . ?
C29 C30 1.532(4) . ?
C30 C31 1.524(4) . ?
C30 C33 1.508(4) . ?
C33 C34 1.379(4) . ?
C34 C35 1.386(4) . ?
C35 C36 1.374(4) . ?
C36 C37 1.377(4) . ?
C39 C40 1.516(4) . ?
C39 C41 1.514(5) . ?
C39 C42 1.509(4) . ?

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
C5 O1 C1 121.2(2) . . ?
C17 O4 C16 116.3(2) . . ?
C17 O6 C18 120.1(2) . . ?
C5 N1 C6 120.3(3) . . ?
C5 N1 C10 123.5(3) . . ?
C6 N1 C10 113.1(2) . . ?
C16 N2 C12 115.9(3) . . ?
O1 C1 C2 111.9(3) . . ?
O1 C1 C3 108.8(3) . . ?
O1 C1 C4 102.2(2) . . ?
C2 C1 C4 109.6(3) . . ?
C3 C1 C2 112.8(3) . . ?
C3 C1 C4 111.1(3) . . ?
O1 C5 N1 111.4(3) . . ?
O2 C5 O1 124.6(3) . . ?
O2 C5 N1 124.0(3) . . ?
N1 C6 C7 111.3(3) . . ?
C6 C7 C8 110.8(2) . . ?
C6 C7 C11 110.7(3) . . ?
C11 C7 C8 111.8(2) . . ?
C7 C8 C9 112.1(2) . . ?
C10 C9 C8 109.5(2) . . ?
C12 C9 C8 112.4(3) . . ?
C12 C9 C10 110.7(2) . . ?
N1 C10 C9 109.5(2) . . ?
O3 C11 C7 112.9(2) . . ?
N2 C12 C9 117.3(3) . . ?
N2 C12 C13 121.9(3) . . ?
C13 C12 C9 120.7(3) . . ?
C14 C13 C12 119.6(3) . . ?
C15 C14 C13 119.1(3) . . ?
C14 C15 C16 116.7(3) . . ?
N2 C16 O4 115.5(3) . . ?
N2 C16 C15 126.8(3) . . ?
C15 C16 O4 117.5(3) . . ?
O5 C17 O4 124.3(3) . . ?
O5 C17 O6 129.7(3) . . ?
O6 C17 O4 105.9(2) . . ?
O6 C18 C19 110.2(2) . . ?
O6 C18 C20 101.1(2) . . ?
O6 C18 C21 109.8(3) . . ?
C19 C18 C20 110.7(3) . . ?
C19 C18 C21 113.9(3) . . ?
C21 C18 C20 110.5(3) . . ?
C26 O7 C22 121.1(2) . . ?
C38 O10 C37 116.5(2) . . ?
C38 O12 C39 119.6(2) . . ?
C26 N3 C27 119.6(2) . . ?
C26 N3 C31 122.1(2) . . ?
C27 N3 C31 112.8(2) . . ?
C37 N4 C33 116.2(2) . . ?
O7 C22 C23 108.1(2) . . ?
O7 C22 C24 111.6(2) . . ?
O7 C22 C25 101.6(2) . . ?
C24 C22 C23 112.4(3) . . ?
C24 C22 C25 110.5(3) . . ?
C25 C22 C23 112.1(3) . . ?
O7 C26 N3 111.2(2) . . ?
O8 C26 O7 124.7(3) . . ?
O8 C26 N3 124.1(3) . . ?
N3 C27 C28 111.3(2) . . ?
C29 C28 C27 111.6(2) . . ?
C32 C28 C27 109.8(2) . . ?
C32 C28 C29 113.0(2) . . ?
C28 C29 C30 112.0(2) . . ?
C31 C30 C29 109.2(2) . . ?
C33 C30 C29 113.0(2) . . ?
C33 C30 C31 112.2(2) . . ?
N3 C31 C30 108.9(2) . . ?
O9 C32 C28 112.5(2) . . ?
N4 C33 C30 117.2(2) . . ?
N4 C33 C34 121.9(3) . . ?
C34 C33 C30 120.9(3) . . ?
C33 C34 C35 119.6(3) . . ?
C36 C35 C34 119.3(3) . . ?
C35 C36 C37 116.3(3) . . ?
N4 C37 O10 113.1(2) . . ?
N4 C37 C36 126.6(3) . . ?
C36 C37 O10 120.2(3) . . ?
O11 C38 O10 125.1(3) . . ?
O11 C38 O12 129.5(3) . . ?
O12 C38 O10 105.4(3) . . ?
O12 C39 C40 101.0(2) . . ?
O12 C39 C41 109.9(3) . . ?
O12 C39 C42 109.9(2) . . ?
C41 C39 C40 111.9(3) . . ?
C42 C39 C40 111.1(3) . . ?
C42 C39 C41 112.5(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_44
_database_code_depnum_ccdc_archive 'CCDC 1840056'
_audit_update_record             
;
2018-04-27 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_audit_creation_date             2017-02-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C26 H25 N3 O5'
_chemical_formula_sum            'C26 H25 N3 O5'
_chemical_formula_weight         459.49
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.1313(16)
_cell_length_b                   8.764(2)
_cell_length_c                   17.546(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.710(5)
_cell_angle_gamma                90
_cell_volume                     1096.1(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.79
_cell_measurement_theta_min      5.04
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.802
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.3867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1359 before and 0.0850 after correction. The Ratio of minimum to maximum transmission is 0.5137. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.576
_exptl_crystal_size_mid          0.422
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13480
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.789
_diffrn_reflns_theta_min         5.043
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker Pt135 CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'Bruker Mircostar Rotating anode'
_diffrn_measurement_device_type  'Rotating anode'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus rotating anode'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_full    0.950
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                3813
_reflns_number_total             3827
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3827
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1120P)²+0.2043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1368
_refine_special_details          
;
 Data quality was not good enough for absoulte structure determination.

 Flack parameter has been removed from the cif.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C15(H15), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C16(H16A,H16B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C22(H22),
 C23(H23), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 1.2534(4) -0.0744(3) 0.93178(16) 0.0194(6) Uani 1 1 d . . . . .
C2 C 1.0625(4) -0.1027(4) 0.93405(16) 0.0216(6) Uani 1 1 d . . . . .
H2 H 1.0166 -0.2022 0.9442 0.026 Uiso 1 1 calc R . . . .
C3 C 0.9400(4) 0.0185(4) 0.92103(16) 0.0215(6) Uani 1 1 d . . . . .
H3 H 0.8084 0.0037 0.9240 0.026 Uiso 1 1 calc R . . . .
C4 C 1.0115(4) 0.1620(3) 0.90365(15) 0.0177(6) Uani 1 1 d . . . . .
C5 C 1.2037(4) 0.1887(3) 0.90469(16) 0.0204(6) Uani 1 1 d . . . . .
H5 H 1.2503 0.2881 0.8951 0.024 Uiso 1 1 calc R . . . .
C6 C 1.3275(4) 0.0689(4) 0.91984(17) 0.0211(6) Uani 1 1 d . . . . .
H6 H 1.4593 0.0853 0.9219 0.025 Uiso 1 1 calc R . . . .
C7 C 0.8733(4) 0.2863(3) 0.88478(16) 0.0186(6) Uani 1 1 d . . . . .
C8 C 0.8399(4) 0.5414(3) 0.83893(17) 0.0200(6) Uani 1 1 d . . . . .
H8A H 0.9159 0.6320 0.8533 0.024 Uiso 1 1 calc R . . . .
H8B H 0.7321 0.5368 0.8731 0.024 Uiso 1 1 calc R . . . .
C9 C 0.7672(4) 0.5582(3) 0.75594(16) 0.0175(6) Uani 1 1 d . . . . .
H9 H 0.8772 0.5564 0.7219 0.021 Uiso 1 1 calc R . . . .
C10 C 0.8110(4) 0.8344(3) 0.74868(15) 0.0174(6) Uani 1 1 d . . . . .
C11 C 0.7305(4) 0.9846(3) 0.74916(16) 0.0187(6) Uani 1 1 d . . . . .
H11 H 0.8106 1.0708 0.7457 0.022 Uiso 1 1 calc R . . . .
C12 C 0.5432(4) 1.0065(3) 0.75438(16) 0.0200(6) Uani 1 1 d . . . . .
H12 H 0.4945 1.1073 0.7568 0.024 Uiso 1 1 calc R . . . .
C13 C 0.4200(4) 0.8806(3) 0.75624(16) 0.0179(6) Uani 1 1 d . . . . .
H13 H 0.2887 0.8964 0.7596 0.021 Uiso 1 1 calc R . . . .
C14 C 0.4904(4) 0.7364(3) 0.75316(15) 0.0165(6) Uani 1 1 d . . . . .
C15 C 0.3585(4) 0.6017(3) 0.74154(16) 0.0176(6) Uani 1 1 d . . . . .
H15 H 0.2388 0.6215 0.7681 0.021 Uiso 1 1 calc R . . . .
C16 C 0.4449(4) 0.4531(3) 0.77038(16) 0.0196(6) Uani 1 1 d . . . . .
H16A H 0.3598 0.3664 0.7586 0.023 Uiso 1 1 calc R . . . .
H16B H 0.4676 0.4576 0.8263 0.023 Uiso 1 1 calc R . . . .
C17 C 0.6298(4) 0.4331(3) 0.72985(16) 0.0186(6) Uani 1 1 d . . . . .
H17 H 0.6846 0.3322 0.7450 0.022 Uiso 1 1 calc R . . . .
C18 C 0.5947(4) 0.4327(3) 0.64339(16) 0.0212(6) Uani 1 1 d . . . . .
H18A H 0.7163 0.4248 0.6179 0.025 Uiso 1 1 calc R . . . .
H18B H 0.5188 0.3421 0.6289 0.025 Uiso 1 1 calc R . . . .
C19 C 0.3183(4) 0.5881(3) 0.65520(16) 0.0199(6) Uani 1 1 d . . . . .
H19A H 0.2368 0.4988 0.6444 0.024 Uiso 1 1 calc R . . . .
H19B H 0.2527 0.6807 0.6362 0.024 Uiso 1 1 calc R . . . .
C20 C 0.4748(4) 0.5759(4) 0.53421(16) 0.0235(6) Uani 1 1 d . . . . .
H20A H 0.3863 0.6588 0.5199 0.028 Uiso 1 1 calc R . . . .
H20B H 0.4196 0.4785 0.5158 0.028 Uiso 1 1 calc R . . . .
C21 C 0.6590(4) 0.6026(3) 0.49535(16) 0.0211(6) Uani 1 1 d . . . . .
C22 C 0.6960(4) 0.5284(3) 0.42779(17) 0.0226(6) Uani 1 1 d . . . . .
H22 H 0.6071 0.4583 0.4067 0.027 Uiso 1 1 calc R . . . .
C23 C 0.8632(4) 0.5557(4) 0.39026(18) 0.0274(7) Uani 1 1 d . . . . .
H23 H 0.8877 0.5039 0.3440 0.033 Uiso 1 1 calc R . . . .
C24 C 0.9929(5) 0.6583(4) 0.42065(19) 0.0280(7) Uani 1 1 d . . . . .
H24 H 1.1066 0.6768 0.3954 0.034 Uiso 1 1 calc R . . . .
C25 C 0.9564(4) 0.7337(4) 0.48785(19) 0.0283(7) Uani 1 1 d . . . . .
H25 H 1.0446 0.8050 0.5084 0.034 Uiso 1 1 calc R . . . .
C26 C 0.7906(4) 0.7054(4) 0.52546(17) 0.0259(7) Uani 1 1 d . . . . .
H26 H 0.7671 0.7565 0.5719 0.031 Uiso 1 1 calc R . . . .
N1 N 1.3829(4) -0.2062(3) 0.93820(14) 0.0230(5) Uani 1 1 d . . . . .
N2 N 0.6814(3) 0.7125(2) 0.75199(13) 0.0154(5) Uani 1 1 d . . . . .
N3 N 0.4971(3) 0.5703(3) 0.61692(13) 0.0188(5) Uani 1 1 d . . . . .
O1 O 1.5514(3) -0.1807(3) 0.94649(13) 0.0306(5) Uani 1 1 d . . . . .
O2 O 1.3147(3) -0.3349(2) 0.93360(14) 0.0299(5) Uani 1 1 d . . . . .
O3 O 0.7086(3) 0.2795(2) 0.89948(12) 0.0231(5) Uani 1 1 d . . . . .
O4 O 0.9533(3) 0.4049(2) 0.84922(11) 0.0203(5) Uani 1 1 d . . . . .
O5 O 0.9803(3) 0.8062(2) 0.74608(12) 0.0229(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 C2 1.386(4) . ?
C1 C6 1.381(4) . ?
C1 N1 1.481(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(4) . ?
C4 C5 1.390(4) . ?
C4 C7 1.499(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(4) . ?
C6 H6 0.9500 . ?
C7 O3 1.212(3) . ?
C7 O4 1.348(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.538(4) . ?
C8 O4 1.452(3) . ?
C9 H9 1.0000 . ?
C9 C17 1.531(4) . ?
C9 N2 1.485(3) . ?
C10 C11 1.436(4) . ?
C10 N2 1.415(3) . ?
C10 O5 1.235(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.355(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.412(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.362(4) . ?
C14 C15 1.520(4) . ?
C14 N2 1.379(3) . ?
C15 H15 1.0000 . ?
C15 C16 1.521(4) . ?
C15 C19 1.538(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.527(4) . ?
C17 H17 1.0000 . ?
C17 C18 1.530(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 N3 1.461(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 N3 1.467(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.517(4) . ?
C20 N3 1.456(4) . ?
C21 C22 1.384(4) . ?
C21 C26 1.393(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.400(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.385(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.383(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.393(5) . ?
C26 H26 0.9500 . ?
N1 O1 1.227(3) . ?
N1 O2 1.231(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 118.0(3) . . ?
C6 C1 C2 123.2(3) . . ?
C6 C1 N1 118.7(3) . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.1(3) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.5(3) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C7 117.5(2) . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 C7 121.5(3) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(3) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 118.1(3) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
O3 C7 C4 123.5(3) . . ?
O3 C7 O4 124.3(3) . . ?
O4 C7 C4 112.2(2) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
O4 C8 H8A 109.3 . . ?
O4 C8 H8B 109.3 . . ?
O4 C8 C9 111.6(2) . . ?
C8 C9 H9 108.4 . . ?
C17 C9 C8 114.2(2) . . ?
C17 C9 H9 108.4 . . ?
N2 C9 C8 105.0(2) . . ?
N2 C9 H9 108.4 . . ?
N2 C9 C17 112.2(2) . . ?
N2 C10 C11 115.5(2) . . ?
O5 C10 C11 125.1(2) . . ?
O5 C10 N2 119.4(2) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.7(3) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 119.9(2) . . ?
C13 C14 N2 120.5(2) . . ?
N2 C14 C15 119.2(2) . . ?
C14 C15 H15 109.7 . . ?
C14 C15 C16 112.2(2) . . ?
C14 C15 C19 106.8(2) . . ?
C16 C15 H15 109.7 . . ?
C16 C15 C19 108.8(2) . . ?
C19 C15 H15 109.7 . . ?
C15 C16 H16A 110.4 . . ?
C15 C16 H16B 110.4 . . ?
C15 C16 C17 106.9(2) . . ?
H16A C16 H16B 108.6 . . ?
C17 C16 H16A 110.4 . . ?
C17 C16 H16B 110.4 . . ?
C9 C17 H17 108.2 . . ?
C16 C17 C9 109.4(2) . . ?
C16 C17 H17 108.2 . . ?
C16 C17 C18 110.1(2) . . ?
C18 C17 C9 112.5(2) . . ?
C18 C17 H17 108.2 . . ?
C17 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
N3 C18 C17 112.0(2) . . ?
N3 C18 H18A 109.2 . . ?
N3 C18 H18B 109.2 . . ?
C15 C19 H19A 110.0 . . ?
C15 C19 H19B 110.0 . . ?
H19A C19 H19B 108.3 . . ?
N3 C19 C15 108.7(2) . . ?
N3 C19 H19A 110.0 . . ?
N3 C19 H19B 110.0 . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
N3 C20 H20A 109.1 . . ?
N3 C20 H20B 109.1 . . ?
N3 C20 C21 112.5(2) . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 C26 119.0(3) . . ?
C26 C21 C20 120.8(3) . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.6(3) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.9(3) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.9(3) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.2(3) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 120.5(3) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
O1 N1 C1 118.2(2) . . ?
O1 N1 O2 124.0(2) . . ?
O2 N1 C1 117.8(2) . . ?
C10 N2 C9 114.9(2) . . ?
C14 N2 C9 123.0(2) . . ?
C14 N2 C10 122.1(2) . . ?
C18 N3 C19 110.8(2) . . ?
C20 N3 C18 112.4(2) . . ?
C20 N3 C19 112.4(2) . . ?
C7 O4 C8 116.8(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
C1 C2 C3 C4 2.2(4) . . . . ?
C2 C1 C6 C5 -4.1(4) . . . . ?
C2 C1 N1 O1 -170.4(2) . . . . ?
C2 C1 N1 O2 10.8(4) . . . . ?
C2 C3 C4 C5 -4.8(4) . . . . ?
C2 C3 C4 C7 175.8(2) . . . . ?
C3 C4 C5 C6 3.0(4) . . . . ?
C3 C4 C7 O3 16.6(4) . . . . ?
C3 C4 C7 O4 -162.9(2) . . . . ?
C4 C5 C6 C1 1.4(4) . . . . ?
C4 C7 O4 C8 -170.7(2) . . . . ?
C5 C4 C7 O3 -162.7(3) . . . . ?
C5 C4 C7 O4 17.8(4) . . . . ?
C6 C1 C2 C3 2.3(4) . . . . ?
C6 C1 N1 O1 13.0(4) . . . . ?
C6 C1 N1 O2 -165.9(3) . . . . ?
C7 C4 C5 C6 -177.7(2) . . . . ?
C8 C9 C17 C16 70.0(3) . . . . ?
C8 C9 C17 C18 -167.3(2) . . . . ?
C8 C9 N2 C10 76.8(3) . . . . ?
C8 C9 N2 C14 -101.8(3) . . . . ?
C9 C8 O4 C7 -104.7(3) . . . . ?
C9 C17 C18 N3 -66.2(3) . . . . ?
C10 C11 C12 C13 -2.7(4) . . . . ?
C11 C10 N2 C9 -176.6(2) . . . . ?
C11 C10 N2 C14 2.0(4) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C15 -169.6(3) . . . . ?
C12 C13 C14 N2 3.2(4) . . . . ?
C13 C14 C15 C16 -157.1(3) . . . . ?
C13 C14 C15 C19 83.7(3) . . . . ?
C13 C14 N2 C9 174.1(2) . . . . ?
C13 C14 N2 C10 -4.4(4) . . . . ?
C14 C15 C16 C17 -55.8(3) . . . . ?
C14 C15 C19 N3 57.2(3) . . . . ?
C15 C14 N2 C9 -13.1(4) . . . . ?
C15 C14 N2 C10 168.4(2) . . . . ?
C15 C16 C17 C9 66.4(3) . . . . ?
C15 C16 C17 C18 -57.7(3) . . . . ?
C15 C19 N3 C18 60.5(3) . . . . ?
C15 C19 N3 C20 -172.7(2) . . . . ?
C16 C15 C19 N3 -64.1(3) . . . . ?
C16 C17 C18 N3 56.1(3) . . . . ?
C17 C9 N2 C10 -158.6(2) . . . . ?
C17 C9 N2 C14 22.8(4) . . . . ?
C17 C18 N3 C19 -57.3(3) . . . . ?
C17 C18 N3 C20 176.0(2) . . . . ?
C19 C15 C16 C17 62.1(3) . . . . ?
C20 C21 C22 C23 178.1(3) . . . . ?
C20 C21 C26 C25 -177.5(3) . . . . ?
C21 C20 N3 C18 -70.4(3) . . . . ?
C21 C20 N3 C19 163.8(3) . . . . ?
C21 C22 C23 C24 -0.3(5) . . . . ?
C22 C21 C26 C25 0.4(5) . . . . ?
C22 C23 C24 C25 -0.2(5) . . . . ?
C23 C24 C25 C26 0.7(5) . . . . ?
C24 C25 C26 C21 -0.8(5) . . . . ?
C26 C21 C22 C23 0.2(4) . . . . ?
N1 C1 C2 C3 -174.2(2) . . . . ?
N1 C1 C6 C5 172.3(2) . . . . ?
N2 C9 C17 C16 -49.3(3) . . . . ?
N2 C9 C17 C18 73.4(3) . . . . ?
N2 C10 C11 C12 1.6(4) . . . . ?
N2 C14 C15 C16 30.0(3) . . . . ?
N2 C14 C15 C19 -89.1(3) . . . . ?
N3 C20 C21 C22 141.8(3) . . . . ?
N3 C20 C21 C26 -40.4(4) . . . . ?
O3 C7 O4 C8 9.9(4) . . . . ?
O4 C8 C9 C17 65.4(3) . . . . ?
O4 C8 C9 N2 -171.3(2) . . . . ?
O5 C10 C11 C12 -178.0(3) . . . . ?
O5 C10 N2 C9 3.0(3) . . . . ?
O5 C10 N2 C14 -178.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_31
_database_code_depnum_ccdc_archive 'CCDC 1840055'
_audit_update_record             
;
2018-04-27 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_audit_creation_date             2015-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H30 N2 O7'
_chemical_formula_sum            'C21 H30 N2 O7'
_chemical_formula_weight         422.47
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.5893(15)
_cell_length_b                   11.638(2)
_cell_length_c                   22.452(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2244.4(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9741
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.377
_cell_measurement_theta_min      3.938
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.3278
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1713 before and 0.1038 after correction.
The Ratio of minimum to maximum transmission is 0.4354.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            40771
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         3.938
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker Pt135 CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker Mircostar Rotating anode'
_diffrn_measurement_device_type  'Rotating anode'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus rotating anode'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3852
_reflns_number_total             3943
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.054

_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3943
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²+0.4170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0899
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C19(H19A,H19B,H19C),
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.92211(17) 0.35261(12) 0.59199(6) 0.0232(3) Uani 1 1 d . . . . .
O2 O 0.94238(18) 0.45488(12) 0.50623(6) 0.0247(3) Uani 1 1 d . . . . .
O3 O 0.6093(2) 0.88356(14) 0.54832(8) 0.0402(5) Uani 1 1 d . . . . .
H3 H 0.5521 0.9280 0.5304 0.060 Uiso 1 1 calc GR . . . .
O4 O 0.4741(3) 0.75387(16) 0.49808(10) 0.0508(6) Uani 1 1 d . . . . .
O5 O 0.26365(18) 0.36928(13) 0.77109(7) 0.0292(4) Uani 1 1 d . . . . .
O6 O 0.0492(2) 0.47838(13) 0.78836(8) 0.0347(4) Uani 1 1 d . . . . .
O7 O 0.05873(17) 0.28584(12) 0.80400(6) 0.0221(3) Uani 1 1 d . . . . .
N1 N 0.7463(2) 0.48874(15) 0.57220(7) 0.0202(4) Uani 1 1 d . . . . .
N2 N 0.44679(19) 0.47417(14) 0.72221(7) 0.0207(4) Uani 1 1 d . . . . .
C1 C 1.0652(3) 0.28502(17) 0.58126(9) 0.0242(4) Uani 1 1 d . . . . .
C2 C 1.2065(3) 0.3626(2) 0.58395(12) 0.0372(6) Uani 1 1 d . . . . .
H2A H 1.2024 0.4169 0.5518 0.056 Uiso 1 1 calc GR . . . .
H2B H 1.2993 0.3171 0.5805 0.056 Uiso 1 1 calc GR . . . .
H2C H 1.2074 0.4030 0.6212 0.056 Uiso 1 1 calc GR . . . .
C3 C 1.0547(4) 0.2190(2) 0.52328(11) 0.0370(6) Uani 1 1 d . . . . .
H3A H 0.9591 0.1764 0.5223 0.055 Uiso 1 1 calc GR . . . .
H3B H 1.1410 0.1670 0.5203 0.055 Uiso 1 1 calc GR . . . .
H3C H 1.0573 0.2719 0.4905 0.055 Uiso 1 1 calc GR . . . .
C4 C 1.0643(3) 0.2022(2) 0.63359(11) 0.0372(6) Uani 1 1 d . . . . .
H4A H 1.0721 0.2448 0.6701 0.056 Uiso 1 1 calc GR . . . .
H4B H 1.1512 0.1507 0.6303 0.056 Uiso 1 1 calc GR . . . .
H4C H 0.9692 0.1590 0.6334 0.056 Uiso 1 1 calc GR . . . .
C5 C 0.8757(2) 0.43389(16) 0.55360(9) 0.0189(4) Uani 1 1 d . . . . .
C6 C 0.6625(2) 0.46278(18) 0.62739(9) 0.0211(4) Uani 1 1 d . . . . .
H6A H 0.7177 0.4039 0.6495 0.025 Uiso 1 1 calc R . . . .
H6B H 0.5593 0.4341 0.6181 0.025 Uiso 1 1 calc R . . . .
C7 C 0.6496(2) 0.57175(17) 0.66511(9) 0.0194(4) Uani 1 1 d . . . . .
H7 H 0.7552 0.5966 0.6755 0.023 Uiso 1 1 calc R . . . .
C8 C 0.5730(2) 0.66771(16) 0.62873(9) 0.0206(4) Uani 1 1 d . . . . .
H8A H 0.5718 0.7379 0.6520 0.025 Uiso 1 1 calc R . . . .
H8B H 0.4661 0.6469 0.6200 0.025 Uiso 1 1 calc R . . . .
C9 C 0.6605(2) 0.68893(17) 0.57011(9) 0.0199(4) Uani 1 1 d . . . . .
H9 H 0.7649 0.7183 0.5790 0.024 Uiso 1 1 calc R . . . .
C10 C 0.6746(3) 0.57699(17) 0.53517(9) 0.0211(4) Uani 1 1 d . . . . .
H10A H 0.5722 0.5518 0.5226 0.025 Uiso 1 1 calc R . . . .
H10B H 0.7375 0.5895 0.4999 0.025 Uiso 1 1 calc R . . . .
C11 C 0.5724(3) 0.77739(17) 0.53453(8) 0.0219(4) Uani 1 1 d . . . . .
C12 C 0.5604(2) 0.55375(17) 0.72230(9) 0.0202(4) Uani 1 1 d . . . . .
C13 C 0.5922(3) 0.6202(2) 0.77177(10) 0.0295(5) Uani 1 1 d . . . . .
H13 H 0.6718 0.6744 0.7709 0.035 Uiso 1 1 calc R . . . .
C14 C 0.5035(3) 0.6050(2) 0.82289(10) 0.0352(6) Uani 1 1 d . . . . .
H14 H 0.5224 0.6496 0.8565 0.042 Uiso 1 1 calc R . . . .
C15 C 0.3877(3) 0.5238(2) 0.82347(10) 0.0294(5) Uani 1 1 d . . . . .
H15 H 0.3267 0.5113 0.8571 0.035 Uiso 1 1 calc R . . . .
C16 C 0.3662(2) 0.46163(18) 0.77192(10) 0.0229(4) Uani 1 1 d . . . . .
C17 C 0.1126(2) 0.38753(18) 0.78891(9) 0.0225(4) Uani 1 1 d . . . . .
C18 C -0.1079(2) 0.27086(19) 0.82162(9) 0.0232(5) Uani 1 1 d . . . . .
C19 C -0.1489(3) 0.3508(2) 0.87247(11) 0.0346(6) Uani 1 1 d . . . . .
H19A H -0.0702 0.3459 0.9027 0.052 Uiso 1 1 calc GR . . . .
H19B H -0.2476 0.3290 0.8890 0.052 Uiso 1 1 calc GR . . . .
H19C H -0.1548 0.4283 0.8579 0.052 Uiso 1 1 calc GR . . . .
C20 C -0.2088(3) 0.2895(3) 0.76740(11) 0.0398(6) Uani 1 1 d . . . . .
H20A H -0.1985 0.3675 0.7541 0.060 Uiso 1 1 calc GR . . . .
H20B H -0.3155 0.2744 0.7774 0.060 Uiso 1 1 calc GR . . . .
H20C H -0.1766 0.2383 0.7362 0.060 Uiso 1 1 calc GR . . . .
C21 C -0.1098(3) 0.1465(2) 0.84153(12) 0.0323(5) Uani 1 1 d . . . . .
H21A H -0.0716 0.0986 0.8099 0.048 Uiso 1 1 calc GR . . . .
H21B H -0.2144 0.1244 0.8513 0.048 Uiso 1 1 calc GR . . . .
H21C H -0.0446 0.1377 0.8760 0.048 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.479(2) . ?
O1 C5 1.340(2) . ?
O2 C5 1.232(3) . ?
O3 H3 0.8200 . ?
O3 C11 1.313(3) . ?
O4 C11 1.207(3) . ?
O5 C16 1.390(3) . ?
O5 C17 1.374(3) . ?
O6 C17 1.189(3) . ?
O7 C17 1.315(3) . ?
O7 C18 1.495(2) . ?
N1 C5 1.348(3) . ?
N1 C6 1.464(3) . ?
N1 C10 1.458(3) . ?
N2 C12 1.345(3) . ?
N2 C16 1.321(3) . ?
C1 C2 1.513(3) . ?
C1 C3 1.514(3) . ?
C1 C4 1.519(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.529(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.532(3) . ?
C7 C12 1.510(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.536(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.526(3) . ?
C9 C11 1.507(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.389(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.372(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(3) . ?
C18 C19 1.514(3) . ?
C18 C20 1.510(3) . ?
C18 C21 1.515(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
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
C5 O1 C1 121.17(16) . . ?
C11 O3 H3 109.5 . . ?
C17 O5 C16 118.35(16) . . ?
C17 O7 C18 120.65(16) . . ?
C5 N1 C6 124.72(17) . . ?
C5 N1 C10 120.34(17) . . ?
C10 N1 C6 114.86(16) . . ?
C16 N2 C12 117.05(18) . . ?
O1 C1 C2 110.03(16) . . ?
O1 C1 C3 111.10(19) . . ?
O1 C1 C4 101.94(17) . . ?
C2 C1 C3 112.6(2) . . ?
C2 C1 C4 110.6(2) . . ?
C3 C1 C4 110.06(19) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 N1 112.34(17) . . ?
O2 C5 O1 123.83(18) . . ?
O2 C5 N1 123.82(18) . . ?
N1 C6 H6A 109.8 . . ?
N1 C6 H6B 109.8 . . ?
N1 C6 C7 109.46(16) . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
C6 C7 H7 108.0 . . ?
C6 C7 C8 109.90(16) . . ?
C8 C7 H7 108.0 . . ?
C12 C7 C6 113.12(16) . . ?
C12 C7 H7 108.0 . . ?
C12 C7 C8 109.66(17) . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C7 C8 C9 111.35(16) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C8 C9 H9 109.2 . . ?
C10 C9 C8 110.01(16) . . ?
C10 C9 H9 109.2 . . ?
C11 C9 C8 108.55(17) . . ?
C11 C9 H9 109.2 . . ?
C11 C9 C10 110.52(16) . . ?
N1 C10 C9 109.99(16) . . ?
N1 C10 H10A 109.7 . . ?
N1 C10 H10B 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O3 C11 C9 113.35(18) . . ?
O4 C11 O3 122.9(2) . . ?
O4 C11 C9 123.76(19) . . ?
N2 C12 C7 117.55(17) . . ?
N2 C12 C13 122.03(19) . . ?
C13 C12 C7 120.38(18) . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C14 119.0(2) . . ?
C14 C13 H13 120.5 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 121.6 . . ?
C14 C15 C16 116.8(2) . . ?
C16 C15 H15 121.6 . . ?
N2 C16 O5 113.96(18) . . ?
N2 C16 C15 125.6(2) . . ?
C15 C16 O5 120.16(19) . . ?
O6 C17 O5 124.5(2) . . ?
O6 C17 O7 129.92(19) . . ?
O7 C17 O5 105.54(17) . . ?
O7 C18 C19 110.50(18) . . ?
O7 C18 C20 108.63(17) . . ?
O7 C18 C21 101.52(16) . . ?
C19 C18 C21 111.24(19) . . ?
C20 C18 C19 112.7(2) . . ?
C20 C18 C21 111.6(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 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
N1 C6 C7 C8 55.4(2) . . . . ?
N1 C6 C7 C12 178.30(16) . . . . ?
N2 C12 C13 C14 -0.4(4) . . . . ?
C1 O1 C5 O2 3.4(3) . . . . ?
C1 O1 C5 N1 -177.68(17) . . . . ?
C5 O1 C1 C2 65.4(2) . . . . ?
C5 O1 C1 C3 -60.0(2) . . . . ?
C5 O1 C1 C4 -177.22(18) . . . . ?
C5 N1 C6 C7 124.1(2) . . . . ?
C5 N1 C10 C9 -124.25(19) . . . . ?
C6 N1 C5 O1 -0.9(3) . . . . ?
C6 N1 C5 O2 178.01(19) . . . . ?
C6 N1 C10 C9 58.8(2) . . . . ?
C6 C7 C8 C9 -55.1(2) . . . . ?
C6 C7 C12 N2 -30.7(2) . . . . ?
C6 C7 C12 C13 151.5(2) . . . . ?
C7 C8 C9 C10 54.6(2) . . . . ?
C7 C8 C9 C11 175.65(16) . . . . ?
C7 C12 C13 C14 177.2(2) . . . . ?
C8 C7 C12 N2 92.3(2) . . . . ?
C8 C7 C12 C13 -85.4(2) . . . . ?
C8 C9 C10 N1 -54.5(2) . . . . ?
C8 C9 C11 O3 86.1(2) . . . . ?
C8 C9 C11 O4 -91.8(3) . . . . ?
C10 N1 C5 O1 -177.55(17) . . . . ?
C10 N1 C5 O2 1.4(3) . . . . ?
C10 N1 C6 C7 -59.1(2) . . . . ?
C10 C9 C11 O3 -153.12(19) . . . . ?
C10 C9 C11 O4 28.9(3) . . . . ?
C11 C9 C10 N1 -174.39(17) . . . . ?
C12 N2 C16 O5 -172.81(17) . . . . ?
C12 N2 C16 C15 0.7(3) . . . . ?
C12 C7 C8 C9 179.93(16) . . . . ?
C12 C13 C14 C15 0.7(4) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C14 C15 C16 O5 172.7(2) . . . . ?
C14 C15 C16 N2 -0.4(3) . . . . ?
C16 O5 C17 O6 23.2(3) . . . . ?
C16 O5 C17 O7 -158.39(17) . . . . ?
C16 N2 C12 C7 -177.94(18) . . . . ?
C16 N2 C12 C13 -0.2(3) . . . . ?
C17 O5 C16 N2 -131.3(2) . . . . ?
C17 O5 C16 C15 54.9(3) . . . . ?
C17 O7 C18 C19 -55.5(2) . . . . ?
C17 O7 C18 C20 68.6(2) . . . . ?
C17 O7 C18 C21 -173.64(18) . . . . ?
C18 O7 C17 O5 -175.42(16) . . . . ?
C18 O7 C17 O6 2.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
