# Electronic Supplementary Material (ESI) for RSC Advances.
# 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 
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data_lzd-14-1-10_
_database_code_depnum_ccdc_archive 'CCDC 1491882'
_audit_update_record             
;
2016-12-05 deposited with the CCDC.
2017-10-16 downloaded from the CCDC.
;
_audit_creation_date             2016-11-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        LZD-14-1-9
_chemical_formula_moiety         'C25 H30 N4 O4, C H4 O'
_chemical_formula_sum            'C26 H34 N4 O5'
_chemical_formula_weight         482.57
_chemical_absolute_configuration rm
_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           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   29.9420(3)
_cell_length_b                   12.19640(13)
_cell_length_c                   6.85035(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2501.64(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17914
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.7070
_cell_measurement_theta_min      2.9350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          1.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            22121
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.669
_diffrn_reflns_theta_min         2.952
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  66.00   1.00    1.00    --    0.00  30.00  60.00  156
  2  ω   -135.00  45.00   1.00    2.00    --  -45.00  60.00 240.00  180
  3  ω   -125.00  20.00   1.00    2.00    --  -45.00  60.00  60.00  145
  4  ω   -135.00   3.00   1.00    2.00    --  -45.00   0.00 240.00  138
  5  ω   -180.00  -1.00   1.00    6.00    --  -90.00  60.00 120.00  179
  6  ω   -146.00 -11.00   1.00    6.00    --  -90.00  60.00 240.00  135
  7  ω   -180.00 -42.00   1.00    6.00    --  -90.00  60.00  60.00  138
  8  ω   -180.00  -5.00   1.00    6.00    --  -90.00   0.00 180.00  175
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0496624000
_diffrn_orient_matrix_UB_12      -0.0315474000
_diffrn_orient_matrix_UB_13      -0.0177836000
_diffrn_orient_matrix_UB_21      -0.0117846000
_diffrn_orient_matrix_UB_22      0.1201566000
_diffrn_orient_matrix_UB_23      -0.0466741000
_diffrn_orient_matrix_UB_31      0.0065516000
_diffrn_orient_matrix_UB_32      -0.0230125000
_diffrn_orient_matrix_UB_33      -0.2191782000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                4392
_reflns_number_total             4506
_reflns_odcompleteness_completeness 98.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.55
_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       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1782 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4506
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.043
_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)+(0.0550P)²+0.5860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0895
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(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:
 C2(H2), C20(H20), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C21(H21A,H21B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), N18(H18), C9(H9), C10(H10), C13(H13), C27(H27), C11(H11), C12(H12),
 C23(H23), C26(H26), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C3(H3A,H3B,H3C), C15(H15A,H15B,H15C), C30(H30A,H30B,H30C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O4 O 0.72286(5) 0.56880(11) 0.5718(2) 0.0213(3) Uani 1 1 d . . . . .
O2 O 0.66334(5) 0.66242(11) 0.0644(2) 0.0230(3) Uani 1 1 d . . . . .
O1 O 0.57873(5) 0.57655(13) 0.6817(2) 0.0276(3) Uani 1 1 d . . . . .
O3 O 0.80055(5) 0.66476(13) -0.0564(2) 0.0319(4) Uani 1 1 d . . . . .
O5 O 0.61901(6) 0.40913(13) 0.8948(3) 0.0358(4) Uani 1 1 d . . . . .
H5 H 0.6079 0.4601 0.8282 0.054 Uiso 1 1 calc GR . . . .
N14 N 0.64046(5) 0.53990(13) 0.2915(3) 0.0209(4) Uani 1 1 d . . . . .
N28 N 0.74192(6) 0.69658(14) 0.3464(2) 0.0204(4) Uani 1 1 d . . . . .
N4 N 0.64269(6) 0.67183(13) 0.6591(3) 0.0213(4) Uani 1 1 d . . . . .
H4 H 0.6448 0.6674 0.7870 0.026 Uiso 1 1 calc R . . . .
N18 N 0.74194(5) 0.55204(14) -0.0131(3) 0.0233(4) Uani 1 1 d . . . . .
H18 H 0.7411 0.5417 -0.1402 0.028 Uiso 1 1 calc R . . . .
C1 C 0.71611(6) 0.65864(16) 0.4930(3) 0.0194(4) Uani 1 1 d . . . . .
C5 C 0.60736(6) 0.62108(16) 0.5791(3) 0.0211(4) Uani 1 1 d . . . . .
C19 C 0.77525(7) 0.61669(17) 0.0550(3) 0.0238(4) Uani 1 1 d . . . . .
C17 C 0.70754(6) 0.49811(16) 0.1001(3) 0.0212(4) Uani 1 1 d . . . . .
H17A H 0.7208 0.4707 0.2232 0.025 Uiso 1 1 calc R . . . .
H17B H 0.6963 0.4341 0.0260 0.025 Uiso 1 1 calc R . . . .
C16 C 0.66814(6) 0.57402(16) 0.1488(3) 0.0198(4) Uani 1 1 d . . . . .
C2 C 0.67786(6) 0.73317(16) 0.5614(3) 0.0199(4) Uani 1 1 d . . . . .
H2 H 0.6650 0.7729 0.4467 0.024 Uiso 1 1 calc R . . . .
C29 C 0.73804(7) 0.80619(17) 0.2587(3) 0.0250(4) Uani 1 1 d . . . . .
H29A H 0.7064 0.8245 0.2412 0.038 Uiso 1 1 calc GR . . . .
H29B H 0.7531 0.8068 0.1316 0.038 Uiso 1 1 calc GR . . . .
H29C H 0.7521 0.8604 0.3448 0.038 Uiso 1 1 calc GR . . . .
C21 C 0.82462(7) 0.67441(17) 0.3440(3) 0.0250(4) Uani 1 1 d . . . . .
H21A H 0.8342 0.7324 0.2520 0.030 Uiso 1 1 calc R . . . .
H21B H 0.8215 0.7079 0.4749 0.030 Uiso 1 1 calc R . . . .
C3 C 0.69707(7) 0.81647(17) 0.7066(3) 0.0243(4) Uani 1 1 d . . . . .
H3A H 0.6730 0.8635 0.7555 0.036 Uiso 1 1 calc GR . . . .
H3B H 0.7196 0.8617 0.6410 0.036 Uiso 1 1 calc GR . . . .
H3C H 0.7109 0.7775 0.8161 0.036 Uiso 1 1 calc GR . . . .
C20 C 0.77944(7) 0.62815(17) 0.2786(3) 0.0217(4) Uani 1 1 d . . . . .
H20 H 0.7760 0.5536 0.3374 0.026 Uiso 1 1 calc R . . . .
C22 C 0.85960(7) 0.58519(17) 0.3511(4) 0.0300(5) Uani 1 1 d . . . . .
C8 C 0.52669(7) 0.67493(17) 0.2706(3) 0.0255(5) Uani 1 1 d . . . . .
C15 C 0.64248(7) 0.43055(16) 0.3796(3) 0.0254(4) Uani 1 1 d . . . . .
H15A H 0.6528 0.3775 0.2820 0.038 Uiso 1 1 calc GR . . . .
H15B H 0.6127 0.4095 0.4257 0.038 Uiso 1 1 calc GR . . . .
H15C H 0.6633 0.4315 0.4899 0.038 Uiso 1 1 calc GR . . . .
C6 C 0.60480(6) 0.61443(16) 0.3553(3) 0.0205(4) Uani 1 1 d . . . . .
H6 H 0.6114 0.6889 0.3016 0.025 Uiso 1 1 calc R . . . .
C9 C 0.49882(7) 0.70200(19) 0.4266(3) 0.0310(5) Uani 1 1 d . . . . .
H9 H 0.4988 0.6582 0.5412 0.037 Uiso 1 1 calc R . . . .
C7 C 0.55862(7) 0.57901(17) 0.2799(3) 0.0239(4) Uani 1 1 d . . . . .
H7A H 0.5618 0.5467 0.1481 0.029 Uiso 1 1 calc R . . . .
H7B H 0.5462 0.5220 0.3674 0.029 Uiso 1 1 calc R . . . .
C10 C 0.47098(8) 0.7932(2) 0.4142(4) 0.0376(6) Uani 1 1 d . . . . .
H10 H 0.4522 0.8115 0.5211 0.045 Uiso 1 1 calc R . . . .
C13 C 0.52559(7) 0.74024(19) 0.1034(4) 0.0320(5) Uani 1 1 d . . . . .
H13 H 0.5443 0.7226 -0.0040 0.038 Uiso 1 1 calc R . . . .
C27 C 0.86769(8) 0.52998(19) 0.5243(4) 0.0401(6) Uani 1 1 d . . . . .
H27 H 0.8521 0.5498 0.6398 0.048 Uiso 1 1 calc R . . . .
C11 C 0.47045(8) 0.85721(19) 0.2477(4) 0.0395(6) Uani 1 1 d . . . . .
H11 H 0.4515 0.9195 0.2409 0.047 Uiso 1 1 calc R . . . .
C12 C 0.49744(8) 0.8307(2) 0.0916(4) 0.0384(6) Uani 1 1 d . . . . .
H12 H 0.4968 0.8741 -0.0236 0.046 Uiso 1 1 calc R . . . .
C23 C 0.88296(8) 0.55392(19) 0.1837(5) 0.0394(6) Uani 1 1 d . . . . .
H23 H 0.8777 0.5914 0.0644 0.047 Uiso 1 1 calc R . . . .
C26 C 0.89923(10) 0.4442(2) 0.5281(6) 0.0568(10) Uani 1 1 d . . . . .
H26 H 0.9049 0.4062 0.6467 0.068 Uiso 1 1 calc R . . . .
C24 C 0.91377(9) 0.4691(2) 0.1888(6) 0.0534(8) Uani 1 1 d . . . . .
H24 H 0.9291 0.4486 0.0730 0.064 Uiso 1 1 calc R . . . .
C30 C 0.58572(10) 0.3333(2) 0.9420(5) 0.0456(7) Uani 1 1 d . . . . .
H30A H 0.5738 0.3007 0.8220 0.068 Uiso 1 1 calc GR . . . .
H30B H 0.5616 0.3705 1.0124 0.068 Uiso 1 1 calc GR . . . .
H30C H 0.5984 0.2755 1.0246 0.068 Uiso 1 1 calc GR . . . .
C25 C 0.92217(9) 0.4147(2) 0.3591(6) 0.0574(9) Uani 1 1 d . . . . .
H25 H 0.9435 0.3571 0.3624 0.069 Uiso 1 1 calc R . . . .


_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
O4 C1 1.238(2) . ?
O2 C16 1.232(2) . ?
O1 C5 1.235(2) . ?
O3 C19 1.225(3) . ?
O5 H5 0.8400 . ?
O5 C30 1.398(3) . ?
N14 C16 1.347(3) . ?
N14 C15 1.465(3) . ?
N14 C6 1.469(2) . ?
N28 C1 1.349(3) . ?
N28 C29 1.470(3) . ?
N28 C20 1.474(2) . ?
N4 H4 0.8800 . ?
N4 C5 1.343(3) . ?
N4 C2 1.455(3) . ?
N18 H18 0.8800 . ?
N18 C19 1.354(3) . ?
N18 C17 1.447(3) . ?
C1 C2 1.535(3) . ?
C5 C6 1.537(3) . ?
C19 C20 1.543(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C16 1.536(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.534(3) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C20 1.533(3) . ?
C21 C22 1.511(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C20 H20 1.0000 . ?
C22 C27 1.386(4) . ?
C22 C23 1.396(4) . ?
C8 C9 1.395(3) . ?
C8 C7 1.512(3) . ?
C8 C13 1.395(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C6 H6 1.0000 . ?
C6 C7 1.538(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C10 H10 0.9500 . ?
C10 C11 1.383(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.391(3) . ?
C27 H27 0.9500 . ?
C27 C26 1.410(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(4) . ?
C12 H12 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.387(4) . ?
C26 H26 0.9500 . ?
C26 C25 1.393(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.365(5) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C25 H25 0.9500 . ?

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
C30 O5 H5 109.5 . . ?
C16 N14 C15 123.68(17) . . ?
C16 N14 C6 118.15(16) . . ?
C15 N14 C6 118.10(16) . . ?
C1 N28 C29 124.82(17) . . ?
C1 N28 C20 118.47(16) . . ?
C29 N28 C20 116.49(16) . . ?
C5 N4 H4 115.9 . . ?
C5 N4 C2 128.28(18) . . ?
C2 N4 H4 115.9 . . ?
C19 N18 H18 116.4 . . ?
C19 N18 C17 127.15(17) . . ?
C17 N18 H18 116.4 . . ?
O4 C1 N28 122.31(18) . . ?
O4 C1 C2 120.85(18) . . ?
N28 C1 C2 116.83(17) . . ?
O1 C5 N4 121.15(19) . . ?
O1 C5 C6 120.68(19) . . ?
N4 C5 C6 118.09(18) . . ?
O3 C19 N18 121.3(2) . . ?
O3 C19 C20 121.7(2) . . ?
N18 C19 C20 117.04(18) . . ?
N18 C17 H17A 109.0 . . ?
N18 C17 H17B 109.0 . . ?
N18 C17 C16 112.90(16) . . ?
H17A C17 H17B 107.8 . . ?
C16 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
O2 C16 N14 122.64(17) . . ?
O2 C16 C17 120.98(17) . . ?
N14 C16 C17 116.35(17) . . ?
N4 C2 C1 112.08(16) . . ?
N4 C2 H2 109.4 . . ?
N4 C2 C3 108.29(17) . . ?
C1 C2 H2 109.4 . . ?
C3 C2 C1 108.08(16) . . ?
C3 C2 H2 109.4 . . ?
N28 C29 H29A 109.5 . . ?
N28 C29 H29B 109.5 . . ?
N28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
C22 C21 C20 110.86(17) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N28 C20 C19 107.58(16) . . ?
N28 C20 C21 111.85(16) . . ?
N28 C20 H20 108.0 . . ?
C19 C20 H20 108.0 . . ?
C21 C20 C19 113.27(18) . . ?
C21 C20 H20 108.0 . . ?
C27 C22 C21 119.9(2) . . ?
C27 C22 C23 118.9(2) . . ?
C23 C22 C21 121.2(2) . . ?
C9 C8 C7 121.9(2) . . ?
C9 C8 C13 118.6(2) . . ?
C13 C8 C7 119.4(2) . . ?
N14 C15 H15A 109.5 . . ?
N14 C15 H15B 109.5 . . ?
N14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N14 C6 C5 107.04(16) . . ?
N14 C6 H6 108.0 . . ?
N14 C6 C7 112.33(16) . . ?
C5 C6 H6 108.0 . . ?
C5 C6 C7 113.24(17) . . ?
C7 C6 H6 108.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C7 C6 111.42(17) . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.7 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 121.0(2) . . ?
C12 C13 H13 119.5 . . ?
C22 C27 H27 120.2 . . ?
C22 C27 C26 119.6(3) . . ?
C26 C27 H27 120.2 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 120.0 . . ?
C13 C12 H12 120.1 . . ?
C11 C12 C13 119.7(2) . . ?
C11 C12 H12 120.1 . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.1(3) . . ?
C24 C23 H23 119.4 . . ?
C27 C26 H26 119.8 . . ?
C25 C26 C27 120.4(3) . . ?
C25 C26 H26 119.8 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.4(3) . . ?
C25 C24 H24 119.8 . . ?
O5 C30 H30A 109.5 . . ?
O5 C30 H30B 109.5 . . ?
O5 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C26 C25 H25 120.2 . . ?
C24 C25 C26 119.6(3) . . ?
C24 C25 H25 120.2 . . ?

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
O4 C1 C2 N4 -23.4(3) . . . . ?
O4 C1 C2 C3 95.9(2) . . . . ?
O1 C5 C6 N14 -107.9(2) . . . . ?
O1 C5 C6 C7 16.5(3) . . . . ?
O3 C19 C20 N28 107.0(2) . . . . ?
O3 C19 C20 C21 -17.1(3) . . . . ?
N14 C6 C7 C8 -156.08(18) . . . . ?
N28 C1 C2 N4 157.46(17) . . . . ?
N28 C1 C2 C3 -83.3(2) . . . . ?
N4 C5 C6 N14 68.9(2) . . . . ?
N4 C5 C6 C7 -166.79(17) . . . . ?
N18 C19 C20 N28 -72.1(2) . . . . ?
N18 C19 C20 C21 163.72(17) . . . . ?
N18 C17 C16 O2 13.9(3) . . . . ?
N18 C17 C16 N14 -164.14(17) . . . . ?
C1 N28 C20 C19 128.14(18) . . . . ?
C1 N28 C20 C21 -106.9(2) . . . . ?
C5 N4 C2 C1 -86.6(2) . . . . ?
C5 N4 C2 C3 154.23(18) . . . . ?
C5 C6 C7 C8 82.5(2) . . . . ?
C19 N18 C17 C16 82.6(2) . . . . ?
C17 N18 C19 O3 -174.42(19) . . . . ?
C17 N18 C19 C20 4.8(3) . . . . ?
C16 N14 C6 C5 -129.69(19) . . . . ?
C16 N14 C6 C7 105.4(2) . . . . ?
C2 N4 C5 O1 -176.23(18) . . . . ?
C2 N4 C5 C6 7.0(3) . . . . ?
C29 N28 C1 O4 -174.45(18) . . . . ?
C29 N28 C1 C2 4.7(3) . . . . ?
C29 N28 C20 C19 -57.0(2) . . . . ?
C29 N28 C20 C21 68.0(2) . . . . ?
C21 C22 C27 C26 177.7(2) . . . . ?
C21 C22 C23 C24 -177.4(2) . . . . ?
C20 N28 C1 O4 -0.1(3) . . . . ?
C20 N28 C1 C2 179.06(16) . . . . ?
C20 C21 C22 C27 -93.4(2) . . . . ?
C20 C21 C22 C23 84.1(2) . . . . ?
C22 C21 C20 N28 156.10(19) . . . . ?
C22 C21 C20 C19 -82.1(2) . . . . ?
C22 C27 C26 C25 -0.1(4) . . . . ?
C22 C23 C24 C25 -0.6(4) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C8 C13 C12 C11 0.6(4) . . . . ?
C15 N14 C16 O2 173.17(18) . . . . ?
C15 N14 C16 C17 -8.8(3) . . . . ?
C15 N14 C6 C5 53.4(2) . . . . ?
C15 N14 C6 C7 -71.5(2) . . . . ?
C6 N14 C16 O2 -3.5(3) . . . . ?
C6 N14 C16 C17 174.47(16) . . . . ?
C9 C8 C7 C6 -91.5(2) . . . . ?
C9 C8 C13 C12 0.1(3) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C7 C8 C9 C10 177.9(2) . . . . ?
C7 C8 C13 C12 -178.4(2) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C13 C8 C9 C10 -0.6(3) . . . . ?
C13 C8 C7 C6 87.0(2) . . . . ?
C27 C22 C23 C24 0.1(3) . . . . ?
C27 C26 C25 C24 -0.4(4) . . . . ?
C23 C22 C27 C26 0.2(3) . . . . ?
C23 C24 C25 C26 0.7(4) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.655
_oxdiff_exptl_absorpt_empirical_full_min 0.416
_exptl_crystal_recrystallization_method 'Vapour deposition'
_chemical_compound_source        'Aspergillus versicolor'
####################################################################### 
# 
# 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_lzd-14-1-9_
_database_code_depnum_ccdc_archive 'CCDC 1491883'
_audit_update_record             
;
2016-12-05 deposited with the CCDC.
2017-10-16 downloaded from the CCDC.
;
_audit_creation_date             2016-11-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        LZD-14-1-37
_chemical_formula_moiety         'C26 H29 N5 O5, C H4 O'
_chemical_formula_sum            'C27 H33 N5 O6'
_chemical_formula_weight         523.58
_chemical_absolute_configuration ad
_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.58993(7)
_cell_length_b                   10.68072(7)
_cell_length_c                   28.6559(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2629.09(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19614
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.8230
_cell_measurement_theta_min      3.0740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            24101
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.684
_diffrn_reflns_theta_min         3.084
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00  70.00   1.00    1.00    --    0.00  55.00  90.00  150
  2  ω   -135.00  16.00   1.00    1.00    --  -45.00  30.00   0.00  151
  3  ω   -135.00  13.00   1.00    1.00    --  -45.00  55.00 270.00  148
  4  ω   -100.00  40.00   1.00    1.00    --  -45.00  55.00  90.00  140
  5  ω   -164.00 -25.00   1.00    7.00    --  -90.00  30.00   0.00  139
  6  ω   -180.00 -45.00   1.00    7.00    --  -90.00  55.00 270.00  135
  7  ω   -180.00   0.00   1.00    7.00    --  -90.00   0.00   0.00  180
  8  ω   -180.00 -24.00   1.00    7.00    --  -90.00  55.00   0.00  156
  9  ω    -80.00  70.00   1.00    1.00    --    0.00  55.00  90.00  150
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0116822000
_diffrn_orient_matrix_UB_12      -0.1290388000
_diffrn_orient_matrix_UB_13      0.0237619000
_diffrn_orient_matrix_UB_21      -0.0611629000
_diffrn_orient_matrix_UB_22      -0.0629648000
_diffrn_orient_matrix_UB_23      -0.0447618000
_diffrn_orient_matrix_UB_31      0.1681647000
_diffrn_orient_matrix_UB_32      -0.0139089000
_diffrn_orient_matrix_UB_33      -0.0179453000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                4688
_reflns_number_total             4759
_reflns_odcompleteness_completeness 98.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.56
_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       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1941 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_coef       0.0022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4759
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.036
_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)+(0.0670P)²+0.3780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.0997
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(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:
 C2(H2), C28(H28), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C16(H16A,H16B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), N26(H26), N12(H12), C7(H7), C21(H21), C10(H10), C24(H24), C9(H9),
 C22(H22), C8(H8), C23(H23)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C31(H31A,H31B,H31C), C29(H29A,H29B,H29C), C32(H32A,H32B,H32C)
2.e Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O2 O 0.5238(2) 0.50352(13) 0.33834(5) 0.0417(4) Uani 1 1 d . . . . .
O1 O 0.50099(19) 0.44488(14) 0.22192(6) 0.0454(4) Uani 1 1 d . . . . .
O4 O 0.2291(2) 0.31971(16) 0.31632(5) 0.0459(4) Uani 1 1 d . . . . .
N4 N 0.5428(2) 0.68985(15) 0.30367(6) 0.0325(4) Uani 1 1 d . . . . .
H4 H 0.5307 0.7695 0.3063 0.039 Uiso 1 1 calc R . . . .
N30 N 0.3016(2) 0.57019(16) 0.24026(6) 0.0356(4) Uani 1 1 d . . . . .
N18 N 0.3254(2) 0.27639(18) 0.38740(6) 0.0396(4) Uani 1 1 d . . . . .
O5 O 0.0640(3) 0.77169(18) 0.31266(7) 0.0685(6) Uani 1 1 d . . . . .
N26 N 0.1496(2) 0.57181(19) 0.32321(7) 0.0431(4) Uani 1 1 d . . . . .
H26 H 0.2158 0.5190 0.3123 0.052 Uiso 1 1 calc R . . . .
O3 O 0.3401(3) 0.4456(2) 0.49702(6) 0.0691(6) Uani 1 1 d . . . . .
N12 N 0.4229(2) 0.50070(18) 0.42413(6) 0.0411(4) Uani 1 1 d . . . . .
H12 H 0.4296 0.4703 0.3964 0.049 Uiso 1 1 calc R . . . .
C5 C 0.5312(2) 0.61917(18) 0.34182(7) 0.0324(4) Uani 1 1 d . . . . .
C1 C 0.4549(2) 0.54260(18) 0.23963(7) 0.0321(4) Uani 1 1 d . . . . .
C19 C 0.2192(3) 0.3309(2) 0.35926(8) 0.0386(5) Uani 1 1 d . . . . .
C2 C 0.5751(2) 0.63792(18) 0.25759(7) 0.0318(4) Uani 1 1 d . . . . .
H2 H 0.5731 0.7085 0.2357 0.038 Uiso 1 1 calc R . . . .
C11 C 0.4735(3) 0.6253(2) 0.42847(8) 0.0381(5) Uani 1 1 d . . . . .
C28 C 0.2340(2) 0.69096(19) 0.25450(8) 0.0372(5) Uani 1 1 d . . . . .
H28 H 0.3212 0.7480 0.2605 0.045 Uiso 1 1 calc R . . . .
C6 C 0.5286(3) 0.68520(19) 0.38786(7) 0.0362(4) Uani 1 1 d . . . . .
C25 C 0.0658(3) 0.5322(2) 0.36290(8) 0.0424(5) Uani 1 1 d . . . . .
C27 C 0.1395(3) 0.6824(2) 0.29998(8) 0.0419(5) Uani 1 1 d . . . . .
C20 C 0.0946(3) 0.4113(2) 0.38055(8) 0.0409(5) Uani 1 1 d . . . . .
C13 C 0.3660(3) 0.4216(2) 0.45611(8) 0.0438(5) Uani 1 1 d . . . . .
C3 C 0.7394(3) 0.5843(2) 0.25568(9) 0.0441(5) Uani 1 1 d . . . . .
H3A H 0.8128 0.6479 0.2644 0.066 Uiso 1 1 calc GR . . . .
H3B H 0.7614 0.5562 0.2246 0.066 Uiso 1 1 calc GR . . . .
H3C H 0.7474 0.5150 0.2769 0.066 Uiso 1 1 calc GR . . . .
C14 C 0.3417(3) 0.2878(2) 0.43856(8) 0.0426(5) Uani 1 1 d . . . . .
H14 H 0.2503 0.2513 0.4538 0.051 Uiso 1 1 calc R . . . .
C7 C 0.5937(3) 0.8046(2) 0.39263(9) 0.0498(6) Uani 1 1 d . . . . .
H7 H 0.6311 0.8455 0.3663 0.060 Uiso 1 1 calc R . . . .
C31 C 0.1949(3) 0.4784(2) 0.21924(9) 0.0456(5) Uani 1 1 d . . . . .
H31A H 0.2008 0.4842 0.1859 0.068 Uiso 1 1 calc GR . . . .
H31B H 0.0904 0.4956 0.2292 0.068 Uiso 1 1 calc GR . . . .
H31C H 0.2240 0.3956 0.2289 0.068 Uiso 1 1 calc GR . . . .
C29 C 0.1367(3) 0.7495(2) 0.21565(10) 0.0494(6) Uani 1 1 d . . . . .
H29A H 0.2017 0.7653 0.1890 0.074 Uiso 1 1 calc GR . . . .
H29B H 0.0927 0.8269 0.2264 0.074 Uiso 1 1 calc GR . . . .
H29C H 0.0545 0.6931 0.2070 0.074 Uiso 1 1 calc GR . . . .
C21 C 0.0020(3) 0.3662(3) 0.41688(9) 0.0543(7) Uani 1 1 d . . . . .
H21 H 0.0151 0.2845 0.4273 0.065 Uiso 1 1 calc R . . . .
C17 C 0.4568(3) 0.2079(2) 0.36645(9) 0.0485(6) Uani 1 1 d . . . . .
H17A H 0.4931 0.2492 0.3383 0.058 Uiso 1 1 calc R . . . .
H17B H 0.4277 0.1225 0.3590 0.058 Uiso 1 1 calc R . . . .
C10 C 0.4774(4) 0.6879(3) 0.47121(9) 0.0533(6) Uani 1 1 d . . . . .
H10 H 0.4347 0.6508 0.4976 0.064 Uiso 1 1 calc R . . . .
C24 C -0.0444(3) 0.6082(3) 0.38496(9) 0.0541(6) Uani 1 1 d . . . . .
H24 H -0.0609 0.6896 0.3745 0.065 Uiso 1 1 calc R . . . .
C9 C 0.5451(4) 0.8055(3) 0.47423(10) 0.0620(7) Uani 1 1 d . . . . .
H9 H 0.5505 0.8458 0.5030 0.074 Uiso 1 1 calc R . . . .
C22 C -0.1090(3) 0.4417(4) 0.43742(9) 0.0626(8) Uani 1 1 d . . . . .
H22 H -0.1703 0.4109 0.4616 0.075 Uiso 1 1 calc R . . . .
C8 C 0.6040(4) 0.8630(2) 0.43532(10) 0.0614(7) Uani 1 1 d . . . . .
H8 H 0.6508 0.9413 0.4377 0.074 Uiso 1 1 calc R . . . .
C16 C 0.5802(3) 0.2112(3) 0.40433(10) 0.0558(7) Uani 1 1 d . . . . .
H16A H 0.6491 0.1395 0.4021 0.067 Uiso 1 1 calc R . . . .
H16B H 0.6414 0.2873 0.4026 0.067 Uiso 1 1 calc R . . . .
C15 C 0.4853(4) 0.2070(3) 0.44884(10) 0.0593(7) Uani 1 1 d . . . . .
H15A H 0.5440 0.2410 0.4748 0.071 Uiso 1 1 calc R . . . .
H15B H 0.4551 0.1217 0.4562 0.071 Uiso 1 1 calc R . . . .
C23 C -0.1286(3) 0.5624(4) 0.42215(9) 0.0627(8) Uani 1 1 d . . . . .
H23 H -0.1999 0.6142 0.4371 0.075 Uiso 1 1 calc R . . . .
O6 O 0.6021(11) 0.4472(5) 0.5585(3) 0.237(4) Uani 1 1 d . . . . .
H6 H 0.5468 0.4726 0.5371 0.356 Uiso 1 1 calc GR . . . .
C32 C 0.6107(12) 0.5360(7) 0.5923(3) 0.184(4) Uani 1 1 d . . . . .
H32A H 0.6923 0.5941 0.5850 0.276 Uiso 1 1 calc GR . . . .
H32B H 0.6325 0.4967 0.6218 0.276 Uiso 1 1 calc GR . . . .
H32C H 0.5133 0.5798 0.5943 0.276 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
O2 C5 1.241(2) . ?
O1 C1 1.226(3) . ?
O4 C19 1.239(3) . ?
N4 H4 0.8600 . ?
N4 C5 1.332(3) . ?
N4 C2 1.459(3) . ?
N30 C1 1.350(3) . ?
N30 C28 1.472(3) . ?
N30 C31 1.471(3) . ?
N18 C19 1.350(3) . ?
N18 C14 1.478(3) . ?
N18 C17 1.473(3) . ?
O5 C27 1.209(3) . ?
N26 H26 0.8600 . ?
N26 C25 1.411(3) . ?
N26 C27 1.359(3) . ?
O3 C13 1.220(3) . ?
N12 H12 0.8600 . ?
N12 C11 1.406(3) . ?
N12 C13 1.339(3) . ?
C5 C6 1.496(3) . ?
C1 C2 1.539(3) . ?
C19 C20 1.502(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.524(3) . ?
C11 C6 1.410(3) . ?
C11 C10 1.396(3) . ?
C28 H28 0.9800 . ?
C28 C27 1.538(3) . ?
C28 C29 1.526(3) . ?
C6 C7 1.399(3) . ?
C25 C20 1.409(4) . ?
C25 C24 1.398(3) . ?
C20 C21 1.396(3) . ?
C13 C14 1.529(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C14 H14 0.9800 . ?
C14 C15 1.534(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.376(4) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C21 H21 0.9300 . ?
C21 C22 1.380(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C16 1.518(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.387(4) . ?
C24 H24 0.9300 . ?
C24 C23 1.377(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.370(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.372(5) . ?
C8 H8 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.514(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C23 H23 0.9300 . ?
O6 H6 0.8200 . ?
O6 C32 1.359(8) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 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 N4 H4 118.6 . . ?
C5 N4 C2 122.79(16) . . ?
C2 N4 H4 118.6 . . ?
C1 N30 C28 125.44(17) . . ?
C1 N30 C31 117.19(18) . . ?
C31 N30 C28 116.85(17) . . ?
C19 N18 C14 128.4(2) . . ?
C19 N18 C17 119.24(19) . . ?
C17 N18 C14 111.89(19) . . ?
C25 N26 H26 115.7 . . ?
C27 N26 H26 115.7 . . ?
C27 N26 C25 128.5(2) . . ?
C11 N12 H12 114.7 . . ?
C13 N12 H12 114.7 . . ?
C13 N12 C11 130.5(2) . . ?
O2 C5 N4 120.13(19) . . ?
O2 C5 C6 122.64(18) . . ?
N4 C5 C6 117.24(17) . . ?
O1 C1 N30 120.42(19) . . ?
O1 C1 C2 119.02(18) . . ?
N30 C1 C2 120.39(17) . . ?
O4 C19 N18 120.4(2) . . ?
O4 C19 C20 120.5(2) . . ?
N18 C19 C20 119.06(19) . . ?
N4 C2 C1 115.25(16) . . ?
N4 C2 H2 106.4 . . ?
N4 C2 C3 110.60(17) . . ?
C1 C2 H2 106.4 . . ?
C3 C2 C1 111.14(17) . . ?
C3 C2 H2 106.4 . . ?
N12 C11 C6 117.43(19) . . ?
C10 C11 N12 122.6(2) . . ?
C10 C11 C6 119.9(2) . . ?
N30 C28 H28 107.0 . . ?
N30 C28 C27 113.01(17) . . ?
N30 C28 C29 111.88(19) . . ?
C27 C28 H28 107.0 . . ?
C29 C28 H28 107.0 . . ?
C29 C28 C27 110.68(18) . . ?
C11 C6 C5 121.27(18) . . ?
C7 C6 C5 120.6(2) . . ?
C7 C6 C11 117.9(2) . . ?
C20 C25 N26 118.3(2) . . ?
C24 C25 N26 122.4(2) . . ?
C24 C25 C20 119.3(2) . . ?
O5 C27 N26 124.9(2) . . ?
O5 C27 C28 119.4(2) . . ?
N26 C27 C28 115.66(18) . . ?
C25 C20 C19 120.2(2) . . ?
C21 C20 C19 120.8(2) . . ?
C21 C20 C25 118.9(2) . . ?
O3 C13 N12 126.3(2) . . ?
O3 C13 C14 119.2(2) . . ?
N12 C13 C14 114.47(19) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N18 C14 C13 114.61(18) . . ?
N18 C14 H14 109.5 . . ?
N18 C14 C15 102.72(19) . . ?
C13 C14 H14 109.5 . . ?
C13 C14 C15 110.7(2) . . ?
C15 C14 H14 109.5 . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.7(2) . . ?
C8 C7 H7 119.1 . . ?
N30 C31 H31A 109.5 . . ?
N30 C31 H31B 109.5 . . ?
N30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.6(3) . . ?
C22 C21 H21 119.7 . . ?
N18 C17 H17A 111.1 . . ?
N18 C17 H17B 111.1 . . ?
N18 C17 C16 103.4(2) . . ?
H17A C17 H17B 109.0 . . ?
C16 C17 H17A 111.1 . . ?
C16 C17 H17B 111.1 . . ?
C11 C10 H10 120.1 . . ?
C9 C10 C11 119.9(2) . . ?
C9 C10 H10 120.1 . . ?
C25 C24 H24 120.0 . . ?
C23 C24 C25 120.0(3) . . ?
C23 C24 H24 120.0 . . ?
C10 C9 H9 119.7 . . ?
C8 C9 C10 120.7(2) . . ?
C8 C9 H9 119.7 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.9(3) . . ?
C23 C22 H22 120.1 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8 120.1 . . ?
C17 C16 H16A 111.2 . . ?
C17 C16 H16B 111.2 . . ?
H16A C16 H16B 109.1 . . ?
C15 C16 C17 103.1(2) . . ?
C15 C16 H16A 111.2 . . ?
C15 C16 H16B 111.2 . . ?
C14 C15 H15A 110.8 . . ?
C14 C15 H15B 110.8 . . ?
C16 C15 C14 104.7(2) . . ?
C16 C15 H15A 110.8 . . ?
C16 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
C24 C23 H23 119.5 . . ?
C22 C23 C24 121.0(3) . . ?
C22 C23 H23 119.5 . . ?
C32 O6 H6 109.5 . . ?
O6 C32 H32A 109.5 . . ?
O6 C32 H32B 109.5 . . ?
O6 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
O2 C5 C6 C11 -18.5(3) . . . . ?
O2 C5 C6 C7 155.8(2) . . . . ?
O1 C1 C2 N4 -134.33(19) . . . . ?
O1 C1 C2 C3 -7.5(3) . . . . ?
O4 C19 C20 C25 -46.7(3) . . . . ?
O4 C19 C20 C21 131.1(2) . . . . ?
N4 C5 C6 C11 161.8(2) . . . . ?
N4 C5 C6 C7 -23.9(3) . . . . ?
N30 C1 C2 N4 50.4(2) . . . . ?
N30 C1 C2 C3 177.27(19) . . . . ?
N30 C28 C27 O5 -171.9(2) . . . . ?
N30 C28 C27 N26 8.5(3) . . . . ?
N18 C19 C20 C25 129.9(2) . . . . ?
N18 C19 C20 C21 -52.4(3) . . . . ?
N18 C14 C15 C16 27.3(3) . . . . ?
N18 C17 C16 C15 33.1(3) . . . . ?
N26 C25 C20 C19 4.0(3) . . . . ?
N26 C25 C20 C21 -173.8(2) . . . . ?
N26 C25 C24 C23 176.7(2) . . . . ?
O3 C13 C14 N18 160.9(2) . . . . ?
O3 C13 C14 C15 -83.6(3) . . . . ?
N12 C11 C6 C5 0.7(3) . . . . ?
N12 C11 C6 C7 -173.7(2) . . . . ?
N12 C11 C10 C9 172.6(3) . . . . ?
N12 C13 C14 N18 -22.4(3) . . . . ?
N12 C13 C14 C15 93.1(2) . . . . ?
C5 N4 C2 C1 59.9(2) . . . . ?
C5 N4 C2 C3 -67.2(2) . . . . ?
C5 C6 C7 C8 -174.7(3) . . . . ?
C1 N30 C28 C27 -112.5(2) . . . . ?
C1 N30 C28 C29 121.8(2) . . . . ?
C19 N18 C14 C13 -58.4(3) . . . . ?
C19 N18 C14 C15 -178.5(2) . . . . ?
C19 N18 C17 C16 156.1(2) . . . . ?
C19 C20 C21 C22 177.8(2) . . . . ?
C2 N4 C5 O2 -11.2(3) . . . . ?
C2 N4 C5 C6 168.46(18) . . . . ?
C11 N12 C13 O3 3.3(4) . . . . ?
C11 N12 C13 C14 -173.2(2) . . . . ?
C11 C6 C7 C8 -0.2(4) . . . . ?
C11 C10 C9 C8 2.1(5) . . . . ?
C28 N30 C1 O1 -171.13(19) . . . . ?
C28 N30 C1 C2 4.0(3) . . . . ?
C6 C11 C10 C9 -4.4(4) . . . . ?
C6 C7 C8 C9 -2.0(5) . . . . ?
C25 N26 C27 O5 7.1(4) . . . . ?
C25 N26 C27 C28 -173.3(2) . . . . ?
C25 C20 C21 C22 -4.4(4) . . . . ?
C25 C24 C23 C22 -1.6(4) . . . . ?
C27 N26 C25 C20 178.9(2) . . . . ?
C27 N26 C25 C24 -0.8(4) . . . . ?
C20 C25 C24 C23 -3.0(4) . . . . ?
C20 C21 C22 C23 -0.1(4) . . . . ?
C13 N12 C11 C6 179.9(2) . . . . ?
C13 N12 C11 C10 2.9(4) . . . . ?
C13 C14 C15 C16 -95.5(2) . . . . ?
C14 N18 C19 O4 174.1(2) . . . . ?
C14 N18 C19 C20 -2.4(3) . . . . ?
C14 N18 C17 C16 -16.7(3) . . . . ?
C31 N30 C1 O1 0.3(3) . . . . ?
C31 N30 C1 C2 175.45(19) . . . . ?
C31 N30 C28 C27 76.1(2) . . . . ?
C31 N30 C28 C29 -49.7(3) . . . . ?
C29 C28 C27 O5 -45.5(3) . . . . ?
C29 C28 C27 N26 134.9(2) . . . . ?
C21 C22 C23 C24 3.2(4) . . . . ?
C17 N18 C19 O4 2.6(3) . . . . ?
C17 N18 C19 C20 -174.0(2) . . . . ?
C17 N18 C14 C13 113.6(2) . . . . ?
C17 N18 C14 C15 -6.5(3) . . . . ?
C17 C16 C15 C14 -37.9(3) . . . . ?
C10 C11 C6 C5 177.8(2) . . . . ?
C10 C11 C6 C7 3.4(3) . . . . ?
C10 C9 C8 C7 1.1(5) . . . . ?
C24 C25 C20 C19 -176.3(2) . . . . ?
C24 C25 C20 C21 6.0(3) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.783
_oxdiff_exptl_absorpt_empirical_full_min 0.471
_exptl_crystal_recrystallization_method 'Vapour deposition'
_chemical_compound_source        'Aspergillus versicolor'
####################################################################### 
# 
# 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_lzd-14-1-4
_database_code_depnum_ccdc_archive 'CCDC 1491884'
_audit_update_record             
;
2016-12-05 deposited with the CCDC.
2017-10-16 downloaded from the CCDC.
;
_audit_creation_date             2016-11-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        LZD-14-1-4
_chemical_formula_moiety         'C25 H29 N5 O5, C H4 O'
_chemical_formula_sum            'C26 H33 N5 O6'
_chemical_formula_weight         511.57
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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                   9.91935(9)
_cell_length_b                   8.16154(7)
_cell_length_c                   15.73111(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.8934(9)
_cell_angle_gamma                90
_cell_volume                     1271.92(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    24089
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.2470
_cell_measurement_theta_min      2.8080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.86
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25191
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.178
_diffrn_reflns_theta_min         2.813
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  60.00   1.00    1.00    --    0.00  60.00 120.00  150
  2  ω    -90.00  60.00   1.00    1.00    --    0.00   0.00  80.00  150
  3  ω   -120.00  60.00   1.00    1.00    --  -30.00  45.00   0.00  180
  4  ω   -120.00  60.00   1.00    1.00    --  -30.00  15.00   0.00  180
  5  ω   -120.00  36.00   1.00    1.00    --  -30.00   0.00 160.00  156
  6  ω   -120.00  54.00   1.00    1.00    --  -30.00  60.00 240.00  174
  7  ω   -150.00  30.00   1.00    2.00    --  -60.00  60.00 200.00  180
  8  ω   -150.00  30.00   1.00    2.00    --  -60.00   0.00 200.00  180
  9  ω   -150.00  30.00   1.00    2.00    --  -60.00  60.00  40.00  180
 10  ω   -150.00  15.00   1.00    2.00    --  -60.00  45.00   0.00  165
 11  ω   -150.00  30.00   1.00    2.00    --  -60.00  60.00 280.00  180
 12  ω   -180.00   0.00   1.00    3.00    --  -90.00  60.00 200.00  180
 13  ω   -180.00  -3.00   1.00    3.00    --  -90.00  60.00 320.00  177
 14  ω   -180.00   0.00   1.00    3.00    --  -90.00  15.00 240.00  180
 15  ω   -180.00   0.00   1.00    3.00    --  -90.00  60.00 280.00  180
 16  ω   -180.00  -2.00   1.00    3.00    --  -90.00  30.00  80.00  178
 17  ω   -157.00  -3.00   1.00    3.00    --  -90.00  45.00  40.00  154
 18  ω   -180.00   0.00   1.00    3.00    --  -90.00  60.00  80.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1551356000
_diffrn_orient_matrix_UB_12      0.0068985000
_diffrn_orient_matrix_UB_13      -0.0002741000
_diffrn_orient_matrix_UB_21      -0.0076277000
_diffrn_orient_matrix_UB_22      0.1814389000
_diffrn_orient_matrix_UB_23      -0.0268104000
_diffrn_orient_matrix_UB_31      0.0064464000
_diffrn_orient_matrix_UB_32      0.0516958000
_diffrn_orient_matrix_UB_33      0.0943376000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_full    0.948
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                4397
_reflns_number_total             4472
_reflns_odcompleteness_completeness 98.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.06
_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       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1964 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4472
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0276
_refine_ls_restrained_S_all      1.068
_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)+(0.0352P)²+0.3512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0697
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C27(H27), C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 N12(H12), N4(H4), N25(H25), C23(H23), C10(H10), C20(H20), C8(H8), C7(H7),
 C9(H9), C22(H22), C21(H21)
2.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C17(H17A,H17B,H17C), C3(H3A,H3B,H3C), C28(H28A,H28B,
 H28C), C31(H31A,H31B,H31C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.53881(14) 0.53414(18) 0.96658(9) 0.0221(3) Uani 1 1 d . . . . .
O2 O 0.45765(14) 0.66159(19) 0.77796(9) 0.0248(3) Uani 1 1 d . . . . .
O4 O 0.47411(14) 0.2167(2) 0.72340(10) 0.0288(4) Uani 1 1 d . . . . .
O3 O 0.04375(15) 0.63590(19) 0.60428(10) 0.0281(3) Uani 1 1 d . . . . .
O5 O 0.89271(15) 0.3631(2) 0.70841(9) 0.0311(4) Uani 1 1 d . . . . .
N29 N 0.70863(17) 0.4681(2) 0.88298(10) 0.0197(3) Uani 1 1 d . . . . .
O6 O 0.69024(18) 0.0045(2) 0.73750(11) 0.0403(4) Uani 1 1 d . . . . .
N12 N 0.21748(16) 0.6436(2) 0.70566(11) 0.0203(4) Uani 1 1 d . . . . .
H12 H 0.2942 0.5987 0.7186 0.024 Uiso 1 1 calc R . . . .
N4 N 0.50230(16) 0.8287(2) 0.88850(10) 0.0183(3) Uani 1 1 d . . . . .
H4 H 0.4780 0.9053 0.9220 0.022 Uiso 1 1 calc R . . . .
N25 N 0.68074(16) 0.4717(2) 0.70142(10) 0.0207(4) Uani 1 1 d . . . . .
H25 H 0.6221 0.5245 0.7291 0.025 Uiso 1 1 calc R . . . .
N16 N 0.29453(16) 0.3365(2) 0.65729(10) 0.0186(3) Uani 1 1 d . . . . .
C1 C 0.62469(19) 0.5772(2) 0.91718(11) 0.0170(4) Uani 1 1 d . . . . .
C11 C 0.17912(19) 0.7693(2) 0.76008(12) 0.0186(4) Uani 1 1 d . . . . .
C13 C 0.15012(19) 0.5829(2) 0.63532(12) 0.0187(4) Uani 1 1 d . . . . .
C5 C 0.41710(19) 0.7682(2) 0.82770(12) 0.0183(4) Uani 1 1 d . . . . .
C26 C 0.80259(19) 0.4382(3) 0.74106(13) 0.0204(4) Uani 1 1 d . . . . .
C14 C 0.22365(19) 0.4403(3) 0.59318(12) 0.0192(4) Uani 1 1 d . . . . .
H14 H 0.2915 0.4876 0.5572 0.023 Uiso 1 1 calc R . . . .
C24 C 0.64571(19) 0.4235(2) 0.61619(12) 0.0194(4) Uani 1 1 d . . . . .
C18 C 0.42799(19) 0.3001(2) 0.66290(12) 0.0200(4) Uani 1 1 d . . . . .
C23 C 0.7377(2) 0.4494(3) 0.55331(13) 0.0221(4) Uani 1 1 d . . . . .
H23 H 0.8212 0.4964 0.5675 0.026 Uiso 1 1 calc R . . . .
C27 C 0.82279(19) 0.5092(3) 0.83131(12) 0.0204(4) Uani 1 1 d . . . . .
H27 H 0.8254 0.6288 0.8260 0.025 Uiso 1 1 calc R . . . .
C19 C 0.51970(19) 0.3530(3) 0.59463(13) 0.0197(4) Uani 1 1 d . . . . .
C10 C 0.0473(2) 0.8317(3) 0.75628(13) 0.0237(4) Uani 1 1 d . . . . .
H10 H -0.0152 0.7935 0.7149 0.028 Uiso 1 1 calc R . . . .
C2 C 0.63776(19) 0.7598(2) 0.89580(13) 0.0178(4) Uani 1 1 d . . . . .
H2 H 0.6812 0.7721 0.8416 0.021 Uiso 1 1 calc R . . . .
C20 C 0.4892(2) 0.3093(3) 0.51012(13) 0.0238(4) Uani 1 1 d . . . . .
H20 H 0.4060 0.2618 0.4954 0.029 Uiso 1 1 calc R . . . .
C8 C 0.1014(2) 1.0085(3) 0.87490(13) 0.0268(5) Uani 1 1 d . . . . .
H8 H 0.0753 1.0864 0.9140 0.032 Uiso 1 1 calc R . . . .
C6 C 0.27478(19) 0.8305(3) 0.82183(12) 0.0186(4) Uani 1 1 d . . . . .
C7 C 0.2331(2) 0.9504(3) 0.87778(13) 0.0253(4) Uani 1 1 d . . . . .
H7 H 0.2952 0.9928 0.9182 0.030 Uiso 1 1 calc R . . . .
C9 C 0.0096(2) 0.9498(3) 0.81357(13) 0.0250(4) Uani 1 1 d . . . . .
H9 H -0.0783 0.9897 0.8107 0.030 Uiso 1 1 calc R . . . .
C22 C 0.7048(2) 0.4050(3) 0.46971(14) 0.0248(5) Uani 1 1 d . . . . .
H22 H 0.7668 0.4222 0.4281 0.030 Uiso 1 1 calc R . . . .
C30 C 0.6887(2) 0.2941(3) 0.90173(15) 0.0288(5) Uani 1 1 d . . . . .
H30A H 0.7287 0.2692 0.9571 0.043 Uiso 1 1 calc GR . . . .
H30B H 0.7306 0.2286 0.8597 0.043 Uiso 1 1 calc GR . . . .
H30C H 0.5938 0.2704 0.9006 0.043 Uiso 1 1 calc GR . . . .
C21 C 0.5806(2) 0.3354(3) 0.44753(13) 0.0267(5) Uani 1 1 d . . . . .
H21 H 0.5587 0.3064 0.3913 0.032 Uiso 1 1 calc R . . . .
C17 C 0.2128(2) 0.2602(3) 0.72158(14) 0.0253(5) Uani 1 1 d . . . . .
H17A H 0.2474 0.2913 0.7774 0.038 Uiso 1 1 calc GR . . . .
H17B H 0.2167 0.1431 0.7160 0.038 Uiso 1 1 calc GR . . . .
H17C H 0.1209 0.2961 0.7135 0.038 Uiso 1 1 calc GR . . . .
C3 C 0.7224(2) 0.8452(3) 0.96635(14) 0.0257(4) Uani 1 1 d . . . . .
H3A H 0.7240 0.9609 0.9555 0.039 Uiso 1 1 calc GR . . . .
H3B H 0.8128 0.8030 0.9679 0.039 Uiso 1 1 calc GR . . . .
H3C H 0.6836 0.8253 1.0201 0.039 Uiso 1 1 calc GR . . . .
C28 C 0.9567(2) 0.4551(3) 0.87366(14) 0.0322(5) Uani 1 1 d . . . . .
H28A H 0.9658 0.5001 0.9301 0.048 Uiso 1 1 calc GR . . . .
H28B H 1.0294 0.4935 0.8409 0.048 Uiso 1 1 calc GR . . . .
H28C H 0.9594 0.3377 0.8768 0.048 Uiso 1 1 calc GR . . . .
C31 C 0.7412(2) -0.0096(3) 0.65550(15) 0.0371(6) Uani 1 1 d . . . . .
H31A H 0.6754 0.0308 0.6138 0.056 Uiso 1 1 calc GR . . . .
H31B H 0.7601 -0.1226 0.6439 0.056 Uiso 1 1 calc GR . . . .
H31C H 0.8227 0.0533 0.6531 0.056 Uiso 1 1 calc GR . . . .
C15 C 0.1240(2) 0.3441(3) 0.53583(14) 0.0285(5) Uani 1 1 d . . . . .
H15A H 0.1707 0.2578 0.5081 0.043 Uiso 1 1 calc GR . . . .
H15B H 0.0829 0.4160 0.4938 0.043 Uiso 1 1 calc GR . . . .
H15C H 0.0554 0.2977 0.5695 0.043 Uiso 1 1 calc GR . . . .
H6 H 0.617(4) 0.074(5) 0.734(2) 0.064(10) 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 1.233(2) . ?
O2 C5 1.250(2) . ?
O4 C18 1.239(2) . ?
O3 C13 1.219(2) . ?
O5 C26 1.219(2) . ?
N29 C1 1.349(2) . ?
N29 C27 1.466(2) . ?
N29 C30 1.466(3) . ?
O6 C31 1.414(3) . ?
O6 H6 0.92(4) . ?
N12 H12 0.8600 . ?
N12 C11 1.402(3) . ?
N12 C13 1.357(3) . ?
N4 H4 0.8600 . ?
N4 C5 1.338(3) . ?
N4 C2 1.456(2) . ?
N25 H25 0.8600 . ?
N25 C26 1.360(3) . ?
N25 C24 1.423(3) . ?
N16 C14 1.469(2) . ?
N16 C18 1.355(2) . ?
N16 C17 1.467(3) . ?
C1 C2 1.535(3) . ?
C11 C10 1.401(3) . ?
C11 C6 1.414(3) . ?
C13 C14 1.541(3) . ?
C5 C6 1.499(3) . ?
C26 C27 1.537(3) . ?
C14 H14 0.9800 . ?
C14 C15 1.523(3) . ?
C24 C23 1.395(3) . ?
C24 C19 1.402(3) . ?
C18 C19 1.505(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.387(3) . ?
C27 H27 0.9800 . ?
C27 C28 1.521(3) . ?
C19 C20 1.395(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.384(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.526(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.388(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.388(3) . ?
C8 C9 1.379(3) . ?
C6 C7 1.393(3) . ?
C7 H7 0.9300 . ?
C9 H9 0.9300 . ?
C22 H22 0.9300 . ?
C22 C21 1.386(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C21 H21 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C1 N29 C27 125.44(17) . . ?
C1 N29 C30 117.82(17) . . ?
C27 N29 C30 116.68(16) . . ?
C31 O6 H6 108(2) . . ?
C11 N12 H12 115.6 . . ?
C13 N12 H12 115.6 . . ?
C13 N12 C11 128.87(16) . . ?
C5 N4 H4 121.3 . . ?
C5 N4 C2 117.46(17) . . ?
C2 N4 H4 121.3 . . ?
C26 N25 H25 118.5 . . ?
C26 N25 C24 123.07(16) . . ?
C24 N25 H25 118.5 . . ?
C18 N16 C14 127.10(16) . . ?
C18 N16 C17 115.72(16) . . ?
C17 N16 C14 117.16(15) . . ?
O1 C1 N29 121.58(18) . . ?
O1 C1 C2 118.90(17) . . ?
N29 C1 C2 119.50(16) . . ?
N12 C11 C6 118.99(17) . . ?
C10 C11 N12 121.43(18) . . ?
C10 C11 C6 119.55(18) . . ?
O3 C13 N12 125.30(18) . . ?
O3 C13 C14 120.95(17) . . ?
N12 C13 C14 113.70(16) . . ?
O2 C5 N4 119.50(17) . . ?
O2 C5 C6 121.96(18) . . ?
N4 C5 C6 118.54(17) . . ?
O5 C26 N25 124.19(19) . . ?
O5 C26 C27 120.99(18) . . ?
N25 C26 C27 114.78(17) . . ?
N16 C14 C13 111.16(15) . . ?
N16 C14 H14 107.8 . . ?
N16 C14 C15 112.51(18) . . ?
C13 C14 H14 107.8 . . ?
C15 C14 C13 109.71(16) . . ?
C15 C14 H14 107.8 . . ?
C23 C24 N25 119.27(17) . . ?
C23 C24 C19 119.83(18) . . ?
C19 C24 N25 120.90(17) . . ?
O4 C18 N16 119.48(17) . . ?
O4 C18 C19 119.52(17) . . ?
N16 C18 C19 120.94(17) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 C24 120.15(19) . . ?
C22 C23 H23 119.9 . . ?
N29 C27 C26 110.94(16) . . ?
N29 C27 H27 107.5 . . ?
N29 C27 C28 111.88(17) . . ?
C26 C27 H27 107.5 . . ?
C28 C27 C26 111.41(17) . . ?
C28 C27 H27 107.5 . . ?
C24 C19 C18 120.57(17) . . ?
C20 C19 C24 118.92(18) . . ?
C20 C19 C18 119.78(18) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 C11 120.52(19) . . ?
C9 C10 H10 119.7 . . ?
N4 C2 C1 107.73(15) . . ?
N4 C2 H2 109.7 . . ?
N4 C2 C3 110.65(16) . . ?
C1 C2 H2 109.7 . . ?
C3 C2 C1 109.48(16) . . ?
C3 C2 H2 109.7 . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.24(19) . . ?
C21 C20 H20 119.4 . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C9 C8 C7 119.4(2) . . ?
C11 C6 C5 121.31(17) . . ?
C7 C6 C11 118.14(17) . . ?
C7 C6 C5 120.55(17) . . ?
C8 C7 C6 121.90(19) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C10 C9 H9 119.8 . . ?
C8 C9 C10 120.45(19) . . ?
C8 C9 H9 119.8 . . ?
C23 C22 H22 119.7 . . ?
C21 C22 C23 120.61(19) . . ?
C21 C22 H22 119.7 . . ?
N29 C30 H30A 109.5 . . ?
N29 C30 H30B 109.5 . . ?
N29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.26(19) . . ?
C22 C21 H21 120.4 . . ?
N16 C17 H17A 109.5 . . ?
N16 C17 H17B 109.5 . . ?
N16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O6 C31 H31A 109.5 . . ?
O6 C31 H31B 109.5 . . ?
O6 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O1 C1 C2 N4 -38.6(2) . . . . ?
O1 C1 C2 C3 81.8(2) . . . . ?
O2 C5 C6 C11 0.9(3) . . . . ?
O2 C5 C6 C7 -179.5(2) . . . . ?
O4 C18 C19 C24 -48.0(3) . . . . ?
O4 C18 C19 C20 122.1(2) . . . . ?
O3 C13 C14 N16 -146.68(18) . . . . ?
O3 C13 C14 C15 -21.6(3) . . . . ?
O5 C26 C27 N29 -132.2(2) . . . . ?
O5 C26 C27 C28 -6.9(3) . . . . ?
N29 C1 C2 N4 142.67(17) . . . . ?
N29 C1 C2 C3 -96.9(2) . . . . ?
N12 C11 C10 C9 176.52(19) . . . . ?
N12 C11 C6 C5 2.5(3) . . . . ?
N12 C11 C6 C7 -177.21(18) . . . . ?
N12 C13 C14 N16 35.7(2) . . . . ?
N12 C13 C14 C15 160.79(18) . . . . ?
N4 C5 C6 C11 -178.76(18) . . . . ?
N4 C5 C6 C7 0.9(3) . . . . ?
N25 C26 C27 N29 50.2(2) . . . . ?
N25 C26 C27 C28 175.52(19) . . . . ?
N25 C24 C23 C22 -179.25(19) . . . . ?
N25 C24 C19 C18 -10.5(3) . . . . ?
N25 C24 C19 C20 179.32(19) . . . . ?
N16 C18 C19 C24 134.8(2) . . . . ?
N16 C18 C19 C20 -55.1(3) . . . . ?
C1 N29 C27 C26 -117.9(2) . . . . ?
C1 N29 C27 C28 117.0(2) . . . . ?
C11 N12 C13 O3 4.1(3) . . . . ?
C11 N12 C13 C14 -178.45(18) . . . . ?
C11 C10 C9 C8 0.4(3) . . . . ?
C11 C6 C7 C8 0.8(3) . . . . ?
C13 N12 C11 C10 12.2(3) . . . . ?
C13 N12 C11 C6 -169.87(19) . . . . ?
C5 N4 C2 C1 -61.8(2) . . . . ?
C5 N4 C2 C3 178.53(17) . . . . ?
C5 C6 C7 C8 -178.9(2) . . . . ?
C26 N25 C24 C23 -45.9(3) . . . . ?
C26 N25 C24 C19 135.1(2) . . . . ?
C14 N16 C18 O4 176.47(19) . . . . ?
C14 N16 C18 C19 -6.3(3) . . . . ?
C24 N25 C26 O5 -0.7(3) . . . . ?
C24 N25 C26 C27 176.78(18) . . . . ?
C24 C23 C22 C21 0.2(3) . . . . ?
C24 C19 C20 C21 -0.4(3) . . . . ?
C18 N16 C14 C13 -122.7(2) . . . . ?
C18 N16 C14 C15 113.8(2) . . . . ?
C18 C19 C20 C21 -170.7(2) . . . . ?
C23 C24 C19 C18 170.44(19) . . . . ?
C23 C24 C19 C20 0.3(3) . . . . ?
C23 C22 C21 C20 -0.4(3) . . . . ?
C27 N29 C1 O1 -173.00(17) . . . . ?
C27 N29 C1 C2 5.7(3) . . . . ?
C19 C24 C23 C22 -0.2(3) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C10 C11 C6 C5 -179.51(18) . . . . ?
C10 C11 C6 C7 0.8(3) . . . . ?
C2 N4 C5 O2 -2.9(3) . . . . ?
C2 N4 C5 C6 176.73(16) . . . . ?
C6 C11 C10 C9 -1.4(3) . . . . ?
C7 C8 C9 C10 1.2(3) . . . . ?
C9 C8 C7 C6 -1.8(3) . . . . ?
C30 N29 C1 O1 4.1(3) . . . . ?
C30 N29 C1 C2 -177.15(18) . . . . ?
C30 N29 C27 C26 65.0(2) . . . . ?
C30 N29 C27 C28 -60.1(2) . . . . ?
C17 N16 C14 C13 58.7(2) . . . . ?
C17 N16 C14 C15 -64.8(2) . . . . ?
C17 N16 C18 O4 -4.9(3) . . . . ?
C17 N16 C18 C19 172.26(18) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.179
_oxdiff_exptl_absorpt_empirical_full_min 0.495
_exptl_crystal_recrystallization_method 'Vapour deposition'
