# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_20200668
_database_code_depnum_ccdc_archive 'CCDC 2075420'
loop_
_audit_author_name
_audit_author_address
'Yu Zhu'
;zhengzhou University
China
;
_audit_update_record             
;
2021-04-05 deposited with the CCDC.	2021-08-29 downloaded from the CCDC.
;
_audit_creation_date             2020-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 N2 O4'
_chemical_formula_sum            'C20 H18 N2 O4'
_chemical_formula_weight         350.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H15N2O4
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                   7.69091(15)
_cell_length_b                   11.2958(2)
_cell_length_c                   20.0933(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1745.61(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5357
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6150
_cell_measurement_theta_min      3.9240
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.900
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12539
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.045
_diffrn_reflns_theta_max         67.045
_diffrn_reflns_theta_min         4.401
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  37.00   1.00    1.00    --  -33.50  37.00  60.00   93
  2  ω    -57.00 -11.00   1.00    1.00    --  -33.50 -37.00 -30.00   46
  3  ω    -86.00 -54.00   1.00    1.00    --  -33.50 122.00-101.00   32
  4  ω   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00 -60.00   87
  5  ω    -87.00 -61.00   1.00    1.00    --  -33.50 178.00  30.00   26
  6  ω    -20.00  34.00   1.00    1.00    --  -33.50  57.00  60.00   54
  7  ω   -102.00 -55.00   1.00    1.00    --  -33.50 -57.00  90.00   47
  8  ω     12.00  42.00   1.00    1.00    --   36.47 -57.00 120.00   30
  9  ω     61.00 101.00   1.00    1.00    --   36.47 178.00 -90.00   40
 10  ω     18.00  81.00   1.00    1.00    --   36.47  57.00-120.00   63
 11  ω    -30.00   5.00   1.00    1.00    --   36.47 -57.00 120.00   35
 12  ω     77.00 104.00   1.00    1.00    --   36.47  77.00  60.00   27
 13  ω     74.00 100.00   1.00    1.00    --   36.47  77.00 150.00   26
 14  ω     17.00  55.00   1.00    1.00    --   36.47  77.00  60.00   38
 15  ω      9.00  68.00   1.00    1.00    --   36.47  77.00 150.00   59
 16  ω     21.00  92.00   1.00    1.00    --   36.47  57.00 -60.00   71
 17  ω     52.00  78.00   1.00    3.00    --  108.00 -61.00-180.00   26
 18  ω     59.00 108.00   1.00    3.00    --  108.00-111.00 -90.00   49
 19  ω     39.00 128.00   1.00    3.00    --  108.00 -45.00  60.00   89
 20  ω     47.00 111.00   1.00    3.00    --  108.00 -45.00-120.00   64
 21  ω     45.00 128.00   1.00    3.00    --  108.00 -61.00 -30.00   83
 22  ω     65.00 103.00   1.00    3.00    --  108.00 -94.00 -60.00   38
 23  ω     86.00 112.00   1.00    3.00    --  108.00-111.00-180.00   26
 24  ω     46.00 128.00   1.00    3.00    --  108.00 -45.00 150.00   82
 25  ω     74.00 111.00   1.00    3.00    --  108.00-111.00  60.00   37
 26  ω     91.00 165.00   1.00    3.00    --  108.00  61.00-180.00   74
 27  ω    108.00 145.00   1.00    3.00    --  108.00  61.00  60.00   37
 28  ω     85.00 126.00   1.00    3.00    --  108.00 -61.00-180.00   41
 29  ω     83.00 147.00   1.00    3.00    --  108.00  77.00  30.00   64
 30  ω     38.00 177.00   1.00    3.00    --  108.00   0.00 -30.00  139
 31  ω     47.00 122.00   1.00    3.00    --  108.00 -77.00  90.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0139211000
_diffrn_orient_matrix_UB_12      0.1072913000
_diffrn_orient_matrix_UB_13      0.0470488000
_diffrn_orient_matrix_UB_21      0.0141919000
_diffrn_orient_matrix_UB_22      0.0831490000
_diffrn_orient_matrix_UB_23      -0.0605077000
_diffrn_orient_matrix_UB_31      -0.1993391000
_diffrn_orient_matrix_UB_32      0.0134011000
_diffrn_orient_matrix_UB_33      -0.0010314000
_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         0.723
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2931
_reflns_number_total             3119
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1177 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0355
_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)+(0.0513P)²+0.1207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0913
_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 Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O1 O 0.8089(3) 0.91145(19) 0.60748(11) 0.0565(5) Uani 1 1 d . . . . .
O2 O 0.4762(2) 0.90805(13) 0.54777(9) 0.0374(4) Uani 1 1 d . . . . .
H2 H 0.3907 0.8914 0.5252 0.056 Uiso 1 1 calc GR . . . .
O3 O 0.6151(3) 0.74344(14) 0.51792(8) 0.0429(4) Uani 1 1 d . . . . .
O4 O 0.5021(3) 0.63278(17) 0.72182(9) 0.0486(5) Uani 1 1 d . . . . .
N1 N 0.6792(3) 0.77863(17) 0.67900(10) 0.0355(4) Uani 1 1 d . . . . .
N2 N 0.6696(3) 0.62315(17) 0.52758(10) 0.0377(5) Uani 1 1 d . . . . .
C1 C 0.6959(3) 0.8427(2) 0.62001(13) 0.0358(5) Uani 1 1 d . . . . .
C2 C 0.5444(3) 0.80699(19) 0.57444(11) 0.0315(5) Uani 1 1 d . . . . .
C3 C 0.4259(3) 0.72728(19) 0.61698(11) 0.0306(5) Uani 1 1 d . . . . .
C4 C 0.5350(3) 0.7031(2) 0.67880(12) 0.0339(5) Uani 1 1 d . . . . .
C5 C 0.3881(3) 0.6109(2) 0.58044(12) 0.0331(5) Uani 1 1 d . . . . .
H5A H 0.3321 0.5558 0.6106 0.040 Uiso 1 1 calc R . . . .
H5B H 0.3095 0.6258 0.5436 0.040 Uiso 1 1 calc R . . . .
C6 C 0.5526(3) 0.5582(2) 0.55490(11) 0.0314(5) Uani 1 1 d . . . . .
C7 C 0.5865(3) 0.42932(19) 0.55844(11) 0.0327(5) Uani 1 1 d . . . . .
C8 C 0.5328(3) 0.3638(2) 0.61311(13) 0.0403(5) Uani 1 1 d . . . . .
H8 H 0.4789 0.4014 0.6487 0.048 Uiso 1 1 calc R . . . .
C9 C 0.5593(4) 0.2422(2) 0.61479(15) 0.0501(7) Uani 1 1 d . . . . .
H9 H 0.5241 0.1987 0.6517 0.060 Uiso 1 1 calc R . . . .
C10 C 0.6379(4) 0.1858(2) 0.56161(16) 0.0517(7) Uani 1 1 d . . . . .
H10 H 0.6544 0.1042 0.5625 0.062 Uiso 1 1 calc R . . . .
C11 C 0.6917(4) 0.2508(3) 0.50724(16) 0.0499(6) Uani 1 1 d . . . . .
H11 H 0.7451 0.2129 0.4716 0.060 Uiso 1 1 calc R . . . .
C12 C 0.6667(4) 0.3718(2) 0.50546(13) 0.0419(6) Uani 1 1 d . . . . .
H12 H 0.7037 0.4150 0.4687 0.050 Uiso 1 1 calc R . . . .
C13 C 0.2552(3) 0.7862(2) 0.64030(12) 0.0388(5) Uani 1 1 d . . . . .
H13A H 0.1894 0.8094 0.6012 0.047 Uiso 1 1 calc R . . . .
H13B H 0.1869 0.7275 0.6640 0.047 Uiso 1 1 calc R . . . .
C14 C 0.2758(4) 0.8945(3) 0.68513(16) 0.0582(8) Uani 1 1 d . . . . .
H14A H 0.3345 0.8720 0.7254 0.087 Uiso 1 1 calc GR . . . .
H14B H 0.1632 0.9258 0.6958 0.087 Uiso 1 1 calc GR . . . .
H14C H 0.3428 0.9537 0.6624 0.087 Uiso 1 1 calc GR . . . .
C15 C 0.7922(3) 0.7927(2) 0.73527(12) 0.0361(5) Uani 1 1 d . . . . .
C16 C 0.8185(3) 0.9043(2) 0.76159(14) 0.0444(6) Uani 1 1 d . . . . .
H16 H 0.7659 0.9702 0.7425 0.053 Uiso 1 1 calc R . . . .
C17 C 0.9244(4) 0.9164(3) 0.81700(14) 0.0524(7) Uani 1 1 d . . . . .
H17 H 0.9431 0.9911 0.8351 0.063 Uiso 1 1 calc R . . . .
C18 C 1.0025(4) 0.8189(3) 0.84551(15) 0.0600(8) Uani 1 1 d . . . . .
H18 H 1.0724 0.8278 0.8830 0.072 Uiso 1 1 calc R . . . .
C19 C 0.9769(4) 0.7085(3) 0.81843(16) 0.0611(8) Uani 1 1 d . . . . .
H19 H 1.0306 0.6429 0.8374 0.073 Uiso 1 1 calc R . . . .
C20 C 0.8714(4) 0.6944(3) 0.76306(14) 0.0486(6) Uani 1 1 d . . . . .
H20 H 0.8541 0.6197 0.7448 0.058 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
O1 C1 1.192(3) . ?
O2 H2 0.8200 . ?
O2 C2 1.366(3) . ?
O3 N2 1.435(2) . ?
O3 C2 1.449(3) . ?
O4 C4 1.201(3) . ?
N1 C1 1.395(3) . ?
N1 C4 1.399(3) . ?
N1 C15 1.435(3) . ?
N2 C6 1.284(3) . ?
C1 C2 1.536(3) . ?
C2 C3 1.540(3) . ?
C3 C4 1.524(3) . ?
C3 C5 1.533(3) . ?
C3 C13 1.545(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.490(3) . ?
C6 C7 1.481(3) . ?
C7 C8 1.388(3) . ?
C7 C12 1.391(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.389(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(4) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.528(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.382(4) . ?
C15 C20 1.384(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.374(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(4) . ?
C20 H20 0.9300 . ?

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 O2 H2 109.5 . . ?
N2 O3 C2 118.20(17) . . ?
C1 N1 C4 112.77(19) . . ?
C1 N1 C15 123.81(19) . . ?
C4 N1 C15 123.35(19) . . ?
C6 N2 O3 113.20(19) . . ?
O1 C1 N1 125.8(2) . . ?
O1 C1 C2 126.7(2) . . ?
N1 C1 C2 107.49(18) . . ?
O2 C2 O3 104.51(18) . . ?
O2 C2 C1 107.81(18) . . ?
O2 C2 C3 118.63(19) . . ?
O3 C2 C1 108.21(19) . . ?
O3 C2 C3 111.55(17) . . ?
C1 C2 C3 105.76(18) . . ?
C2 C3 C13 114.80(19) . . ?
C4 C3 C2 103.38(18) . . ?
C4 C3 C5 109.96(18) . . ?
C4 C3 C13 107.34(18) . . ?
C5 C3 C2 110.34(18) . . ?
C5 C3 C13 110.68(19) . . ?
O4 C4 N1 124.6(2) . . ?
O4 C4 C3 126.1(2) . . ?
N1 C4 C3 109.24(19) . . ?
C3 C5 H5A 109.6 . . ?
C3 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 C3 110.28(18) . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
N2 C6 C5 120.9(2) . . ?
N2 C6 C7 117.3(2) . . ?
C7 C6 C5 121.74(19) . . ?
C8 C7 C6 120.7(2) . . ?
C8 C7 C12 119.3(2) . . ?
C12 C7 C6 120.0(2) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 H12 119.9 . . ?
C11 C12 C7 120.3(3) . . ?
C11 C12 H12 119.9 . . ?
C3 C13 H13A 108.3 . . ?
C3 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
C14 C13 C3 115.8(2) . . ?
C14 C13 H13A 108.3 . . ?
C14 C13 H13B 108.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 N1 119.4(2) . . ?
C16 C15 C20 120.9(2) . . ?
C20 C15 N1 119.7(2) . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.9(3) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.7(3) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 C19 119.3(3) . . ?
C15 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N2 0.82 2.01 2.824(3) 171.1 3_466

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 O2 -46.0(3) . . . . ?
O1 C1 C2 O3 66.5(3) . . . . ?
O1 C1 C2 C3 -173.8(3) . . . . ?
O2 C2 C3 C4 -131.9(2) . . . . ?
O2 C2 C3 C5 110.6(2) . . . . ?
O2 C2 C3 C13 -15.3(3) . . . . ?
O3 N2 C6 C5 -7.0(3) . . . . ?
O3 N2 C6 C7 171.67(19) . . . . ?
O3 C2 C3 C4 106.6(2) . . . . ?
O3 C2 C3 C5 -10.9(3) . . . . ?
O3 C2 C3 C13 -136.8(2) . . . . ?
N1 C1 C2 O2 134.8(2) . . . . ?
N1 C1 C2 O3 -112.7(2) . . . . ?
N1 C1 C2 C3 6.9(2) . . . . ?
N1 C15 C16 C17 178.4(2) . . . . ?
N1 C15 C20 C19 -178.4(3) . . . . ?
N2 O3 C2 O2 -169.21(18) . . . . ?
N2 O3 C2 C1 76.1(2) . . . . ?
N2 O3 C2 C3 -39.8(3) . . . . ?
N2 C6 C7 C8 143.9(2) . . . . ?
N2 C6 C7 C12 -38.7(3) . . . . ?
C1 N1 C4 O4 173.9(2) . . . . ?
C1 N1 C4 C3 -7.8(3) . . . . ?
C1 N1 C15 C16 53.1(3) . . . . ?
C1 N1 C15 C20 -127.9(3) . . . . ?
C1 C2 C3 C4 -10.8(2) . . . . ?
C1 C2 C3 C5 -128.37(19) . . . . ?
C1 C2 C3 C13 105.7(2) . . . . ?
C2 O3 N2 C6 51.8(3) . . . . ?
C2 C3 C4 O4 -170.2(2) . . . . ?
C2 C3 C4 N1 11.5(2) . . . . ?
C2 C3 C5 C6 48.7(2) . . . . ?
C2 C3 C13 C14 -61.9(3) . . . . ?
C3 C5 C6 N2 -42.2(3) . . . . ?
C3 C5 C6 C7 139.2(2) . . . . ?
C4 N1 C1 O1 -178.9(3) . . . . ?
C4 N1 C1 C2 0.4(3) . . . . ?
C4 N1 C15 C16 -123.6(3) . . . . ?
C4 N1 C15 C20 55.4(3) . . . . ?
C4 C3 C5 C6 -64.7(2) . . . . ?
C4 C3 C13 C14 52.4(3) . . . . ?
C5 C3 C4 O4 -52.4(3) . . . . ?
C5 C3 C4 N1 129.3(2) . . . . ?
C5 C3 C13 C14 172.4(2) . . . . ?
C5 C6 C7 C8 -37.4(3) . . . . ?
C5 C6 C7 C12 140.0(2) . . . . ?
C6 C7 C8 C9 177.5(3) . . . . ?
C6 C7 C12 C11 -177.1(3) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C8 C7 C12 C11 0.3(4) . . . . ?
C8 C9 C10 C11 0.7(5) . . . . ?
C9 C10 C11 C12 -0.4(5) . . . . ?
C10 C11 C12 C7 -0.2(4) . . . . ?
C12 C7 C8 C9 0.1(4) . . . . ?
C13 C3 C4 O4 68.1(3) . . . . ?
C13 C3 C4 N1 -110.3(2) . . . . ?
C13 C3 C5 C6 176.88(19) . . . . ?
C15 N1 C1 O1 4.1(4) . . . . ?
C15 N1 C1 C2 -176.7(2) . . . . ?
C15 N1 C4 O4 -9.1(4) . . . . ?
C15 N1 C4 C3 169.3(2) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C15 C20 C19 0.7(4) . . . . ?
C16 C17 C18 C19 0.7(5) . . . . ?
C17 C18 C19 C20 -0.7(5) . . . . ?
C18 C19 C20 C15 0.0(5) . . . . ?
C20 C15 C16 C17 -0.7(4) . . . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.999
_oxdiff_exptl_absorpt_empirical_full_min 0.843
####################################################################### 
# 
# 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_20210342
_database_code_depnum_ccdc_archive 'CCDC 2075423'
loop_
_audit_author_name
_audit_author_address
'Yu Zhu'
;zhengzhou University
China
;
_audit_update_record             
;
2021-04-05 deposited with the CCDC.	2021-08-29 downloaded from the CCDC.
;
_audit_creation_date             2021-03-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H25 N3 O7'
_chemical_formula_sum            'C32 H25 N3 O7'
_chemical_formula_weight         563.55
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O5N2Br1
_chemical_oxdiff_usercomment     r
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      trigonal
_space_group_IT_number           144
_space_group_name_H-M_alt        'P 31'
_space_group_name_Hall           'P 31'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   14.1958(4)
_cell_length_b                   14.1958(4)
_cell_length_c                   29.4228(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5135.0(3)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    13377
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      61.3360
_cell_measurement_theta_min      3.8820
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.845
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.093
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1764
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            56519
_diffrn_reflns_point_group_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         3.595
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00 -16.00   1.00    1.25    --  -33.50 -77.00-150.00   29
  2  ω   -101.00 -57.00   1.00    1.25    --  -33.50 -77.00-150.00   44
  3  ω    -30.00  -5.00   1.00    1.25    --  -33.50 -19.00-180.00   25
  4  ω    -84.00 -46.00   1.00    1.25    --  -33.50 178.00-180.00   38
  5  ω     -7.00  18.00   1.00    1.25    --   36.47 105.00-118.81   25
  6  ω     15.00  51.00   1.00    1.25    --   36.47  37.00-150.00   36
  7  ω     57.00  83.00   1.00    1.25    --   36.47  77.00 -90.00   26
  8  ω     18.00  68.00   1.00    1.25    --   36.47  57.00  90.00   50
  9  ω    -23.00  55.00   1.00    1.25    --   36.47 -37.00 150.00   78
 10  ω     66.00 110.00   1.00    1.25    --   36.47 178.00  30.00   44
 11  ω    -10.00  15.00   1.00    1.25    --   36.47 110.00  92.76   25
 12  ω     57.00  82.00   1.00    1.25    --   36.47-108.00-158.00   25
 13  ω     80.00 106.00   1.00    1.25    --   36.47  37.00-150.00   26
 14  ω     11.00  46.00   1.00    1.25    --   36.47  77.00 -90.00   35
 15  ω     69.00  97.00   1.00    1.25    --   36.47  37.00 150.00   28
 16  ω     -5.00  21.00   1.00    1.25    --   36.47 100.00-128.96   26
 17  ω     33.00  69.00   1.00    1.25    --   36.47  37.00  90.00   36
 18  ω     61.00  87.00   1.00    1.25    --   36.47  57.00-150.00   26
 19  ω     18.00  43.00   1.00    1.25    --   36.47  37.00 -60.00   25
 20  ω     73.00 104.00   1.00    1.25    --   36.47  57.00  90.00   31
 21  ω      8.00  49.00   1.00    1.25    --   36.47  77.00 150.00   41
 22  ω     57.00 110.00   1.00    1.25    --   36.47 178.00 120.00   53
 23  ω     39.00  65.00   1.00    1.25    --   36.47  57.00 120.00   26
 24  ω     19.00  58.00   1.00    1.25    --   36.47  57.00-180.00   39
 25  ω     82.00 108.00   1.00   12.50    --  108.00  30.00-120.00   26
 26  ω    120.00 177.00   1.00   12.50    --  108.00  77.00-150.00   57
 27  ω     82.00 108.00   1.00   12.50    --  108.00  30.00-150.00   26
 28  ω     88.00 114.00   1.00   12.50    --  108.00  61.00-180.00   26
 29  ω     88.00 114.00   1.00   12.50    --  108.00  61.00 -90.00   26
 30  ω     82.00 107.00   1.00   12.50    --  108.00  30.00 -60.00   25
 31  ω     88.00 114.00   1.00   12.50    --  108.00  61.00-150.00   26
 32  ω     79.00 105.00   1.00   12.50    --  108.00  77.00-150.00   26
 33  ω     89.00 115.00   1.00   12.50    --  108.00  53.00-178.08   26
 34  ω     88.00 114.00   1.00   12.50    --  108.00  45.00-180.00   26
 35  ω     37.00 103.00   1.00   12.50    --  108.00-108.00-158.00   66
 36  ω     57.00  95.00   1.00   12.50    --  108.00-109.00 159.00   38
 37  ω     83.00 118.00   1.00   16.00    --  108.00  30.00 -90.00   35
 38  ω    125.00 177.00   1.00   16.00    --  108.00  77.00-120.00   52
 39  ω     79.00 173.00   1.00   16.00    --  108.00  77.00-180.00   94
 40  ω     88.00 113.00   1.00   16.00    --  108.00  61.00-120.00   25
 41  ω     88.00 114.00   1.00   16.00    --  108.00  45.00-120.00   26
 42  ω     88.00 116.00   1.00   16.00    --  108.00  45.00-150.00   28
 43  ω     79.00 105.00   1.00   16.00    --  108.00  77.00-120.00   26
 44  ω    147.00 173.00   1.00   16.00    --  108.00  77.00 150.00   26
 45  ω    110.00 177.00   1.00   16.00    --  108.00  77.00 -90.00   67
 46  ω     79.00 104.00   1.00   16.00    --  108.00  77.00 -90.00   25
 47  ω     81.00 107.00   1.00   16.00    --  108.00  77.00 150.00   26
 48  ω     88.00 114.00   1.00   16.00    --  108.00  45.00 -90.00   26
 49  ω     84.00 126.00   1.00   16.00    --  108.00 -61.00-150.00   42
 50  ω     25.00  64.00   1.00    3.50    --   36.47  37.00  30.00   39
 51  ω     37.00  63.00   1.00    3.50    --   36.47  57.00-120.00   26
 52  ω     73.00  98.00   1.00    3.50    --   36.47  57.00-120.00   25
 53  ω     93.00 129.00   1.00   16.00    --  108.00  45.00 -30.00   36
 54  ω     56.00 112.00   1.00   16.00    --  108.00-111.00  90.00   56
 55  ω     72.00 118.00   1.00   16.00    --  108.00 -61.00 120.00   46
 56  ω    134.00 160.00   1.00   16.00    --  108.00  45.00 -30.00   26
 57  ω     78.00 107.00   1.00   16.00    --  108.00-111.00-120.00   29
 58  ω     51.00  77.00   1.00   16.00    --  108.00 -94.00  30.00   26
 59  ω   -101.00 -61.00   1.00    3.50    --  -33.50 -77.00 -60.00   40
 60  ω    -57.00  -5.00   1.00    3.50    --  -33.50 -77.00 -60.00   52
 61  ω    -23.00  11.00   1.00    3.50    --   36.47 -57.00 -30.00   34
 62  ω     83.00 110.00   1.00    3.50    --   36.47 178.00-150.00   27
 63  ω     57.00  82.00   1.00    3.50    --   36.47 178.00-180.00   25
 64  ω     33.00  70.00   1.00    3.50    --   36.47  57.00  30.00   37
 65  ω     63.00  94.00   1.00    3.50    --   36.47  19.00 -30.00   31
 66  ω     14.00  40.00   1.00    3.50    --   36.47  19.00 -30.00   26
 67  ω     49.00 108.00   1.00   16.00    --  108.00-111.00 -90.00   59
 68  ω    102.00 128.00   1.00   16.00    --  108.00  61.00 -90.00   26
 69  ω    100.00 161.00   1.00   16.00    --  108.00 111.00 120.00   61
 70  ω     58.00  86.00   1.00   16.00    --  108.00 -45.00  90.00   28
 71  ω    101.00 163.00   1.00   16.00    --  108.00 111.00  60.00   62
 72  ω     41.00  67.00   1.00   16.00    --  108.00 -94.00 120.00   26
 73  ω    136.00 174.00   1.00   16.00    --  108.00  45.00  90.00   38
 74  ω     67.00 106.00   1.00   16.00    --  108.00-111.00   0.00   39
 75  ω    137.00 163.00   1.00   16.00    --  108.00  61.00 150.00   26
 76  ω    125.00 151.00   1.00   16.00    --  108.00  61.00   0.00   26
 77  ω    -57.00 -32.00   1.00    3.50    --  -33.50 178.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1064565000
_diffrn_orient_matrix_UB_12      -0.1083485000
_diffrn_orient_matrix_UB_13      -0.0073139000
_diffrn_orient_matrix_UB_21      0.0659989000
_diffrn_orient_matrix_UB_22      -0.0571109000
_diffrn_orient_matrix_UB_23      -0.0096767000
_diffrn_orient_matrix_UB_31      -0.0029106000
_diffrn_orient_matrix_UB_32      -0.0264832000
_diffrn_orient_matrix_UB_33      0.0509270000
_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         0.838
_reflns_Friedel_fraction_full    0.838
_reflns_Friedel_fraction_max     0.838
_reflns_number_gt                9436
_reflns_number_total             11190
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.463
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 3534 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.22(11)
_refine_ls_extinction_coef       0.0010(3)
_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   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     689
_refine_ls_number_reflns         11190
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0670
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1456P)²+0.0018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1940
_refine_ls_wR_factor_ref         0.2057
_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. Restrained distances
 C26'-C25'
 1.55 with sigma of 0.02
3. Rigid bond restraints
 N1', C9'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(O4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C9') \\sim Ueq, Uanis(N1') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5.a Riding coordinates:
 O2(H2)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C20(H20A,H20B), C25(H25A,H25B), C10'(H10C,H10D), C20'(H20C,
 H20D), C25'(H25C,H25D)
5.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C2(H2A), C1(H1), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14), C17(H17), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C1'(H1'),
  C2'(H2'A), C3'(H3'), C4'(H4'), C7'(H7'), C11'(H11'), C12'(H12'), C13'(H13'),
 C14'(H14'), C17'(H17'), C32'(H32'), C31'(H31'), C30'(H30'), C29'(H29'),
 C28'(H28')
5.d Fitted hexagon refined as free rotating group:
 C6(C5,C4,C3,C2,C1), C11(C12,C13,C14,C15,C16), C27(C28,C29,C30,C31,C32),
 C5'(C6',C1',C2',C3',C4'), C15'(C16',C11',C12',C13',C14'), C27'(C32',C31',C30',
 C29',C28')
5.e Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C26'(H26D,H26E,H26F)
5.f Idealised tetrahedral OH refined as rotating group:
 O2'(H2')
;
_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 -0.0257(3) 0.4073(4) 0.59783(18) 0.1107(13) Uani 1 1 d . . . . .
O2 O -0.2196(4) 0.3464(4) 0.48882(18) 0.1073(12) Uani 1 1 d . . . . .
H2 H -0.2340 0.3418 0.4566 0.161 Uiso 1 1 d R . . . .
O3 O 0.0251(3) 0.6238(3) 0.56701(13) 0.0887(9) Uani 1 1 d . . . . .
O4 O 0.0352(3) 0.8151(3) 0.67165(11) 0.0807(8) Uani 1 1 d . U . . .
O5 O 0.2481(4) 0.6185(4) 0.68336(15) 0.0991(10) Uani 1 1 d . . . . .
O6 O 0.3660(3) 0.8814(4) 0.56812(18) 0.1085(13) Uani 1 1 d . . . . .
O7 O 0.3823(4) 0.6946(4) 0.53884(15) 0.1011(11) Uani 1 1 d . . . . .
N1 N -0.1240(4) 0.4455(4) 0.49102(18) 0.0933(11) Uani 1 1 d . . . . .
N2 N 0.1211(3) 0.6808(3) 0.59149(14) 0.0790(9) Uani 1 1 d . . . . .
N3 N 0.3248(3) 0.6383(3) 0.61208(14) 0.0766(8) Uani 1 1 d . . . . .
C6 C -0.1591(4) 0.2373(4) 0.61130(16) 0.1085(17) Uani 1 1 d . . . . .
C5 C -0.0616(4) 0.3235(4) 0.62698(19) 0.120(2) Uani 1 1 d G . . . .
C4 C -0.0156(4) 0.3128(5) 0.6670(2) 0.156(4) Uani 1 1 d G . . . .
H4 H 0.0496 0.3705 0.6774 0.187 Uiso 1 1 calc R . . . .
C3 C -0.0671(6) 0.2160(6) 0.6913(2) 0.162(4) Uani 1 1 d G . . . .
H3 H -0.0363 0.2088 0.7180 0.194 Uiso 1 1 calc R . . . .
C2 C -0.1645(6) 0.1297(5) 0.6756(2) 0.161(4) Uani 1 1 d G . . . .
H2A H -0.1990 0.0649 0.6918 0.193 Uiso 1 1 calc R . . . .
C1 C -0.2106(5) 0.1404(3) 0.6356(2) 0.139(3) Uani 1 1 d G . . . .
H1 H -0.2758 0.0827 0.6251 0.166 Uiso 1 1 calc R . . . .
C7 C -0.1789(5) 0.2748(5) 0.5703(2) 0.1009(16) Uani 1 1 d . . . . .
H7 H -0.2382 0.2354 0.5512 0.121 Uiso 1 1 calc R . . . .
C8 C -0.0989(4) 0.3756(4) 0.56310(19) 0.0850(12) Uani 1 1 d . . . . .
C9 C -0.0682(4) 0.4553(4) 0.52734(18) 0.0822(11) Uani 1 1 d . . . . .
C10 C 0.0369(4) 0.5620(5) 0.5315(2) 0.0917(13) Uani 1 1 d . . . . .
H10A H 0.0962 0.5489 0.5385 0.110 Uiso 1 1 calc R . . . .
H10B H 0.0533 0.6016 0.5031 0.110 Uiso 1 1 calc R . . . .
C11 C -0.2337(2) 0.7489(3) 0.64250(13) 0.1032(16) Uani 1 1 d . . . . .
H11 H -0.2849 0.7070 0.6206 0.124 Uiso 1 1 calc R . . . .
C12 C -0.2578(3) 0.8058(4) 0.67447(15) 0.111(2) Uani 1 1 d G . . . .
H12 H -0.3252 0.8019 0.6740 0.133 Uiso 1 1 calc R . . . .
C13 C -0.1813(4) 0.8686(4) 0.70718(13) 0.112(2) Uani 1 1 d G . . . .
H13 H -0.1975 0.9066 0.7286 0.135 Uiso 1 1 calc R . . . .
C14 C -0.0806(3) 0.8744(3) 0.70792(12) 0.0986(15) Uani 1 1 d G . . . .
H14 H -0.0294 0.9163 0.7298 0.118 Uiso 1 1 calc R . . . .
C15 C -0.0565(2) 0.8175(3) 0.67595(12) 0.0808(11) Uani 1 1 d G . . . .
C16 C -0.1330(3) 0.7547(3) 0.64324(10) 0.0862(12) Uani 1 1 d G . . . .
C17 C -0.0812(4) 0.7095(4) 0.61736(19) 0.0853(11) Uani 1 1 d . . . . .
H17 H -0.1109 0.6621 0.5929 0.102 Uiso 1 1 calc R . . . .
C18 C 0.0192(4) 0.7480(4) 0.63484(15) 0.0741(10) Uani 1 1 d . . . . .
C19 C 0.1139(4) 0.7377(3) 0.62303(16) 0.0734(9) Uani 1 1 d . . . . .
C20 C 0.2149(4) 0.8032(4) 0.65121(18) 0.0814(11) Uani 1 1 d . . . . .
H20A H 0.1960 0.7849 0.6829 0.098 Uiso 1 1 calc R . . . .
H20B H 0.2378 0.8796 0.6476 0.098 Uiso 1 1 calc R . . . .
C21 C 0.2888(4) 0.6745(4) 0.64922(17) 0.0803(11) Uani 1 1 d . . . . .
C22 C 0.3108(4) 0.7880(4) 0.64033(19) 0.0844(11) Uani 1 1 d . . . . .
C23 C 0.3447(3) 0.8061(4) 0.5915(2) 0.0846(13) Uani 1 1 d . . . . .
C24 C 0.3544(4) 0.7079(4) 0.5756(2) 0.0841(12) Uani 1 1 d . . . . .
C25 C 0.4083(6) 0.8652(7) 0.6712(4) 0.131(3) Uani 1 1 d . . . . .
H25A H 0.4275 0.9390 0.6631 0.157 Uiso 1 1 calc R . . . .
H25B H 0.3812 0.8535 0.7021 0.157 Uiso 1 1 calc R . . . .
C26 C 0.5023(7) 0.8620(10) 0.6720(3) 0.140(3) Uani 1 1 d . . . . .
H26A H 0.5382 0.8852 0.6432 0.210 Uiso 1 1 calc GR . . . .
H26B H 0.4863 0.7889 0.6780 0.210 Uiso 1 1 calc GR . . . .
H26C H 0.5489 0.9094 0.6955 0.210 Uiso 1 1 calc GR . . . .
C27 C 0.3261(3) 0.5391(2) 0.61295(16) 0.0824(11) Uani 1 1 d . . . . .
C28 C 0.2314(2) 0.4405(3) 0.60544(19) 0.112(2) Uani 1 1 d G . . . .
H28 H 0.1669 0.4393 0.5986 0.134 Uiso 1 1 calc R . . . .
C29 C 0.2332(4) 0.3436(2) 0.6082(2) 0.127(2) Uani 1 1 d G . . . .
H29 H 0.1699 0.2777 0.6032 0.152 Uiso 1 1 calc R . . . .
C30 C 0.3296(5) 0.3453(3) 0.6185(2) 0.130(3) Uani 1 1 d G . . . .
H30 H 0.3308 0.2805 0.6203 0.156 Uiso 1 1 calc R . . . .
C31 C 0.4243(3) 0.4439(4) 0.6260(3) 0.167(4) Uani 1 1 d G . . . .
H31 H 0.4888 0.4451 0.6328 0.200 Uiso 1 1 calc R . . . .
C32 C 0.4225(2) 0.5408(3) 0.6232(2) 0.134(3) Uani 1 1 d G . . . .
H32 H 0.4858 0.6067 0.6282 0.161 Uiso 1 1 calc R . . . .
O1' O 1.0285(3) 0.9359(4) 0.50902(15) 0.0986(10) Uani 1 1 d . . . . .
O2' O 1.2070(3) 1.0462(4) 0.62483(16) 0.1007(10) Uani 1 1 d . . . . .
H2' H 1.2337 1.0672 0.6501 0.151 Uiso 1 1 calc GR . . . .
O3' O 0.9652(3) 1.0867(3) 0.54766(15) 0.0902(9) Uani 1 1 d . . . . .
O4' O 0.9518(3) 1.2786(3) 0.44943(15) 0.0957(10) Uani 1 1 d . . . . .
O5' O 0.7355(4) 0.8598(4) 0.43636(14) 0.1044(12) Uani 1 1 d . . . . .
O6' O 0.6228(3) 1.0168(3) 0.54820(16) 0.0978(10) Uani 1 1 d . . . . .
O7' O 0.6093(4) 0.8163(3) 0.58075(13) 0.0970(10) Uani 1 1 d . . . . .
N1' N 1.1101(4) 1.0475(4) 0.62182(18) 0.0908(10) Uani 1 1 d . U . . .
N2' N 0.8684(3) 1.0490(3) 0.52343(15) 0.0804(9) Uani 1 1 d . . . . .
N3' N 0.6656(3) 0.8117(3) 0.50800(14) 0.0759(8) Uani 1 1 d . . . . .
C5' C 1.0692(3) 0.8953(4) 0.47939(15) 0.1016(16) Uani 1 1 d . . . . .
C6' C 1.1604(3) 0.8959(3) 0.49695(13) 0.0946(14) Uani 1 1 d G . . . .
C1' C 1.2145(4) 0.8555(4) 0.47123(19) 0.122(2) Uani 1 1 d G . . . .
H1' H 1.2755 0.8559 0.4830 0.146 Uiso 1 1 calc R . . . .
C2' C 1.1773(6) 0.8144(5) 0.42796(19) 0.135(3) Uani 1 1 d G . . . .
H2'A H 1.2135 0.7873 0.4107 0.162 Uiso 1 1 calc R . . . .
C3' C 1.0861(6) 0.8137(5) 0.41040(14) 0.152(4) Uani 1 1 d G . . . .
H3' H 1.0613 0.7862 0.3814 0.183 Uiso 1 1 calc R . . . .
C4' C 1.0321(4) 0.8542(5) 0.43611(17) 0.152(4) Uani 1 1 d G . . . .
H4' H 0.9710 0.8537 0.4244 0.182 Uiso 1 1 calc R . . . .
C7' C 1.1741(5) 0.9436(5) 0.54018(19) 0.0894(12) Uani 1 1 d . . . . .
H7' H 1.2291 0.9572 0.5608 0.107 Uiso 1 1 calc R . . . .
C8' C 1.0936(4) 0.9658(3) 0.54642(19) 0.0808(11) Uani 1 1 d . . . . .
C9' C 1.0604(4) 1.0086(4) 0.58359(19) 0.0809(10) Uani 1 1 d . U . . .
C10' C 0.9528(4) 1.0063(5) 0.5807(2) 0.0925(14) Uani 1 1 d . . . . .
H10C H 0.8956 0.9347 0.5714 0.111 Uiso 1 1 calc R . . . .
H10D H 0.9337 1.0229 0.6101 0.111 Uiso 1 1 calc R . . . .
C15' C 1.0430(3) 1.3717(3) 0.44419(15) 0.0996(17) Uani 1 1 d . . . . .
C16' C 1.1227(4) 1.3809(3) 0.47424(15) 0.112(2) Uani 1 1 d G . . . .
C11' C 1.2242(4) 1.4748(4) 0.47460(19) 0.131(3) Uani 1 1 d G . . . .
H11' H 1.2776 1.4810 0.4947 0.157 Uiso 1 1 calc R . . . .
C12' C 1.2460(4) 1.5595(3) 0.4449(2) 0.148(4) Uani 1 1 d G . . . .
H12' H 1.3139 1.6223 0.4451 0.178 Uiso 1 1 calc R . . . .
C13' C 1.1663(5) 1.5503(3) 0.4149(2) 0.148(4) Uani 1 1 d G . . . .
H13' H 1.1809 1.6069 0.3950 0.177 Uiso 1 1 calc R . . . .
C14' C 1.0648(4) 1.4564(4) 0.41449(16) 0.131(3) Uani 1 1 d G . . . .
H14' H 1.0114 1.4503 0.3944 0.158 Uiso 1 1 calc R . . . .
C17' C 1.0689(5) 1.2784(5) 0.4994(2) 0.1003(15) Uani 1 1 d . . . . .
H17' H 1.0992 1.2575 0.5226 0.120 Uiso 1 1 calc R . . . .
C18' C 0.9692(4) 1.2210(4) 0.4830(2) 0.0865(12) Uani 1 1 d . . . . .
C19' C 0.8742(4) 1.1164(4) 0.49316(18) 0.0801(11) Uani 1 1 d . . . . .
C20' C 0.7734(5) 1.0833(4) 0.46552(19) 0.0841(12) Uani 1 1 d . . . . .
H20C H 0.7910 1.0830 0.4337 0.101 Uiso 1 1 calc R . . . .
H20D H 0.7520 1.1378 0.4694 0.101 Uiso 1 1 calc R . . . .
C21' C 0.7004(4) 0.8795(4) 0.47013(18) 0.0827(11) Uani 1 1 d . . . . .
C22' C 0.6758(4) 0.9715(4) 0.47743(18) 0.0824(11) Uani 1 1 d . . . . .
C23' C 0.6435(3) 0.9591(4) 0.52599(17) 0.0777(10) Uani 1 1 d . . . . .
C24' C 0.6361(3) 0.8542(4) 0.54424(16) 0.0739(10) Uani 1 1 d . . . . .
C25' C 0.5810(6) 0.9521(7) 0.4461(3) 0.1144(19) Uani 1 1 d D . . . .
H25C H 0.5627 1.0079 0.4531 0.137 Uiso 1 1 calc R . . . .
H25D H 0.6085 0.9652 0.4152 0.137 Uiso 1 1 calc R . . . .
C26' C 0.4839(10) 0.8524(11) 0.4462(4) 0.167(4) Uani 1 1 d D . . . .
H26D H 0.4385 0.8508 0.4217 0.251 Uiso 1 1 calc GR . . . .
H26E H 0.4469 0.8435 0.4746 0.251 Uiso 1 1 calc GR . . . .
H26F H 0.4996 0.7945 0.4424 0.251 Uiso 1 1 calc GR . . . .
C27' C 0.6698(3) 0.7146(2) 0.51108(15) 0.0813(11) Uani 1 1 d . . . . .
C32' C 0.5753(2) 0.6159(3) 0.5186(2) 0.134(3) Uani 1 1 d G . . . .
H32' H 0.5088 0.6134 0.5212 0.161 Uiso 1 1 calc R . . . .
C31' C 0.5803(4) 0.5208(2) 0.5223(3) 0.176(5) Uani 1 1 d G . . . .
H31' H 0.5171 0.4548 0.5274 0.211 Uiso 1 1 calc R . . . .
C30' C 0.6797(4) 0.5245(3) 0.5185(3) 0.138(3) Uani 1 1 d G . . . .
H30' H 0.6830 0.4609 0.5210 0.166 Uiso 1 1 calc R . . . .
C29' C 0.7741(3) 0.6233(4) 0.51101(19) 0.113(2) Uani 1 1 d G . . . .
H29' H 0.8406 0.6257 0.5085 0.135 Uiso 1 1 calc R . . . .
C28' C 0.7692(2) 0.7183(3) 0.50728(17) 0.1008(16) Uani 1 1 d G . . . .
H28' H 0.8324 0.7844 0.5022 0.121 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
O1 C5 1.343(7) . ?
O1 C8 1.364(7) . ?
O2 H2 0.9648 . ?
O2 N1 1.385(7) . ?
O3 N2 1.389(5) . ?
O3 C10 1.427(6) . ?
O4 C15 1.325(4) . ?
O4 C18 1.384(6) . ?
O5 C21 1.231(7) . ?
O6 C23 1.176(6) . ?
O7 C24 1.199(7) . ?
N1 C9 1.296(7) . ?
N2 C19 1.268(6) . ?
N3 C21 1.408(7) . ?
N3 C24 1.375(7) . ?
N3 C27 1.418(5) . ?
C6 C5 1.3900 . ?
C6 C1 1.3900 . ?
C6 C7 1.404(8) . ?
C5 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C3 1.3900 . ?
C3 H3 0.9300 . ?
C3 C2 1.3900 . ?
C2 H2A 0.9300 . ?
C2 C1 1.3900 . ?
C1 H1 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.325(9) . ?
C8 C9 1.443(8) . ?
C9 C10 1.509(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11 0.9300 . ?
C11 C12 1.3900 . ?
C11 C16 1.3900 . ?
C12 H12 0.9300 . ?
C12 C13 1.3900 . ?
C13 H13 0.9300 . ?
C13 C14 1.3900 . ?
C14 H14 0.9300 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
C16 C17 1.416(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.347(7) . ?
C18 C19 1.466(6) . ?
C19 C20 1.508(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C22 1.515(7) . ?
C21 C22 1.503(7) . ?
C22 C23 1.496(8) . ?
C22 C25 1.557(8) . ?
C23 C24 1.541(8) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.359(12) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.3900 . ?
C27 C32 1.3900 . ?
C28 H28 0.9300 . ?
C28 C29 1.3900 . ?
C29 H29 0.9300 . ?
C29 C30 1.3900 . ?
C30 H30 0.9300 . ?
C30 C31 1.3900 . ?
C31 H31 0.9300 . ?
C31 C32 1.3900 . ?
C32 H32 0.9300 . ?
O1' C5' 1.327(6) . ?
O1' C8' 1.361(7) . ?
O2' H2' 0.8200 . ?
O2' N1' 1.387(6) . ?
O3' N2' 1.395(6) . ?
O3' C10' 1.441(7) . ?
O4' C15' 1.318(5) . ?
O4' C18' 1.381(7) . ?
O5' C21' 1.205(7) . ?
O6' C23' 1.194(6) . ?
O7' C24' 1.176(6) . ?
N1' C9' 1.296(8) . ?
N2' C19' 1.279(6) . ?
N3' C21' 1.391(7) . ?
N3' C24' 1.389(6) . ?
N3' C27' 1.412(5) . ?
C5' C6' 1.3900 . ?
C5' C4' 1.3900 . ?
C6' C1' 1.3900 . ?
C6' C7' 1.408(7) . ?
C1' H1' 0.9300 . ?
C1' C2' 1.3900 . ?
C2' H2'A 0.9300 . ?
C2' C3' 1.3900 . ?
C3' H3' 0.9300 . ?
C3' C4' 1.3900 . ?
C4' H4' 0.9300 . ?
C7' H7' 0.9300 . ?
C7' C8' 1.341(8) . ?
C8' C9' 1.440(8) . ?
C9' C10' 1.515(7) . ?
C10' H10C 0.9700 . ?
C10' H10D 0.9700 . ?
C15' C16' 1.3900 . ?
C15' C14' 1.3900 . ?
C16' C11' 1.3900 . ?
C16' C17' 1.463(8) . ?
C11' H11' 0.9300 . ?
C11' C12' 1.3900 . ?
C12' H12' 0.9300 . ?
C12' C13' 1.3900 . ?
C13' H13' 0.9300 . ?
C13' C14' 1.3900 . ?
C14' H14' 0.9300 . ?
C17' H17' 0.9300 . ?
C17' C18' 1.322(9) . ?
C18' C19' 1.453(7) . ?
C19' C20' 1.503(8) . ?
C20' H20C 0.9700 . ?
C20' H20D 0.9700 . ?
C20' C22' 1.537(8) . ?
C21' C22' 1.527(7) . ?
C22' C23' 1.484(8) . ?
C22' C25' 1.538(8) . ?
C23' C24' 1.537(7) . ?
C25' H25C 0.9700 . ?
C25' H25D 0.9700 . ?
C25' C26' 1.397(13) . ?
C26' H26D 0.9600 . ?
C26' H26E 0.9600 . ?
C26' H26F 0.9600 . ?
C27' C32' 1.3900 . ?
C27' C28' 1.3900 . ?
C32' H32' 0.9300 . ?
C32' C31' 1.3900 . ?
C31' H31' 0.9300 . ?
C31' C30' 1.3900 . ?
C30' H30' 0.9300 . ?
C30' C29' 1.3900 . ?
C29' H29' 0.9300 . ?
C29' C28' 1.3900 . ?
C28' H28' 0.9300 . ?

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 C8 107.2(4) . . ?
N1 O2 H2 100.4 . . ?
N2 O3 C10 110.8(4) . . ?
C15 O4 C18 105.5(3) . . ?
C9 N1 O2 112.5(5) . . ?
C19 N2 O3 112.5(4) . . ?
C21 N3 C27 122.4(4) . . ?
C24 N3 C21 112.3(4) . . ?
C24 N3 C27 125.3(4) . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C7 104.6(4) . . ?
C1 C6 C7 135.4(4) . . ?
O1 C5 C6 109.8(4) . . ?
O1 C5 C4 130.2(4) . . ?
C6 C5 C4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C3 C2 C1 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C6 C1 H1 120.0 . . ?
C2 C1 C6 120.0 . . ?
C2 C1 H1 120.0 . . ?
C6 C7 H7 125.7 . . ?
C8 C7 C6 108.7(5) . . ?
C8 C7 H7 125.7 . . ?
O1 C8 C9 113.9(5) . . ?
C7 C8 O1 109.7(6) . . ?
C7 C8 C9 136.2(5) . . ?
N1 C9 C8 126.0(5) . . ?
N1 C9 C10 114.8(5) . . ?
C8 C9 C10 119.2(5) . . ?
O3 C10 C9 108.4(4) . . ?
O3 C10 H10A 110.0 . . ?
O3 C10 H10B 110.0 . . ?
C9 C10 H10A 110.0 . . ?
C9 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C16 120.0 . . ?
C16 C11 H11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0 . . ?
C15 C14 H14 120.0 . . ?
O4 C15 C14 127.6(3) . . ?
O4 C15 C16 112.4(3) . . ?
C16 C15 C14 120.0 . . ?
C11 C16 C17 135.8(3) . . ?
C15 C16 C11 120.0 . . ?
C15 C16 C17 104.3(3) . . ?
C16 C17 H17 126.4 . . ?
C18 C17 C16 107.1(4) . . ?
C18 C17 H17 126.4 . . ?
O4 C18 C19 114.2(4) . . ?
C17 C18 O4 110.8(4) . . ?
C17 C18 C19 134.9(5) . . ?
N2 C19 C18 127.4(4) . . ?
N2 C19 C20 116.2(4) . . ?
C18 C19 C20 116.4(4) . . ?
C19 C20 H20A 108.2 . . ?
C19 C20 H20B 108.2 . . ?
C19 C20 C22 116.2(4) . . ?
H20A C20 H20B 107.4 . . ?
C22 C20 H20A 108.2 . . ?
C22 C20 H20B 108.2 . . ?
O5 C21 N3 122.4(4) . . ?
O5 C21 C22 127.9(5) . . ?
N3 C21 C22 109.7(4) . . ?
C20 C22 C25 108.8(5) . . ?
C21 C22 C20 113.3(4) . . ?
C21 C22 C25 106.8(5) . . ?
C23 C22 C20 114.4(4) . . ?
C23 C22 C21 103.2(4) . . ?
C23 C22 C25 110.0(6) . . ?
O6 C23 C22 129.2(6) . . ?
O6 C23 C24 123.1(6) . . ?
C22 C23 C24 107.6(4) . . ?
O7 C24 N3 126.6(5) . . ?
O7 C24 C23 127.1(5) . . ?
N3 C24 C23 106.3(5) . . ?
C22 C25 H25A 106.8 . . ?
C22 C25 H25B 106.8 . . ?
H25A C25 H25B 106.7 . . ?
C26 C25 C22 121.9(9) . . ?
C26 C25 H25A 106.8 . . ?
C26 C25 H25B 106.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 N3 120.8(3) . . ?
C28 C27 C32 120.0 . . ?
C32 C27 N3 119.2(3) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 C27 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 120.0 . . ?
C28 C29 C30 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.0 . . ?
C32 C31 H31 120.0 . . ?
C27 C32 H32 120.0 . . ?
C31 C32 C27 120.0 . . ?
C31 C32 H32 120.0 . . ?
C5' O1' C8' 106.9(4) . . ?
N1' O2' H2' 109.5 . . ?
N2' O3' C10' 109.5(4) . . ?
C15' O4' C18' 107.5(5) . . ?
C9' N1' O2' 112.5(5) . . ?
C19' N2' O3' 112.7(4) . . ?
C21' N3' C27' 123.5(4) . . ?
C24' N3' C21' 113.2(4) . . ?
C24' N3' C27' 122.9(4) . . ?
O1' C5' C6' 111.1(3) . . ?
O1' C5' C4' 128.9(3) . . ?
C6' C5' C4' 120.0 . . ?
C5' C6' C7' 104.0(4) . . ?
C1' C6' C5' 120.0 . . ?
C1' C6' C7' 136.0(4) . . ?
C6' C1' H1' 120.0 . . ?
C6' C1' C2' 120.0 . . ?
C2' C1' H1' 120.0 . . ?
C1' C2' H2'A 120.0 . . ?
C1' C2' C3' 120.0 . . ?
C3' C2' H2'A 120.0 . . ?
C2' C3' H3' 120.0 . . ?
C4' C3' C2' 120.0 . . ?
C4' C3' H3' 120.0 . . ?
C5' C4' H4' 120.0 . . ?
C3' C4' C5' 120.0 . . ?
C3' C4' H4' 120.0 . . ?
C6' C7' H7' 126.0 . . ?
C8' C7' C6' 108.0(5) . . ?
C8' C7' H7' 126.0 . . ?
O1' C8' C9' 115.6(4) . . ?
C7' C8' O1' 110.0(5) . . ?
C7' C8' C9' 134.4(5) . . ?
N1' C9' C8' 128.0(4) . . ?
N1' C9' C10' 112.8(5) . . ?
C8' C9' C10' 119.1(5) . . ?
O3' C10' C9' 107.4(4) . . ?
O3' C10' H10C 110.2 . . ?
O3' C10' H10D 110.2 . . ?
C9' C10' H10C 110.2 . . ?
C9' C10' H10D 110.2 . . ?
H10C C10' H10D 108.5 . . ?
O4' C15' C16' 111.4(4) . . ?
O4' C15' C14' 128.6(4) . . ?
C16' C15' C14' 120.0 . . ?
C15' C16' C11' 120.0 . . ?
C15' C16' C17' 103.5(4) . . ?
C11' C16' C17' 136.5(4) . . ?
C16' C11' H11' 120.0 . . ?
C16' C11' C12' 120.0 . . ?
C12' C11' H11' 120.0 . . ?
C11' C12' H12' 120.0 . . ?
C11' C12' C13' 120.0 . . ?
C13' C12' H12' 120.0 . . ?
C12' C13' H13' 120.0 . . ?
C14' C13' C12' 120.0 . . ?
C14' C13' H13' 120.0 . . ?
C15' C14' H14' 120.0 . . ?
C13' C14' C15' 120.0 . . ?
C13' C14' H14' 120.0 . . ?
C16' C17' H17' 126.5 . . ?
C18' C17' C16' 107.1(6) . . ?
C18' C17' H17' 126.5 . . ?
O4' C18' C19' 113.7(5) . . ?
C17' C18' O4' 110.5(5) . . ?
C17' C18' C19' 135.7(6) . . ?
N2' C19' C18' 126.0(5) . . ?
N2' C19' C20' 116.6(4) . . ?
C18' C19' C20' 117.4(4) . . ?
C19' C20' H20C 108.5 . . ?
C19' C20' H20D 108.5 . . ?
C19' C20' C22' 115.2(4) . . ?
H20C C20' H20D 107.5 . . ?
C22' C20' H20C 108.5 . . ?
C22' C20' H20D 108.5 . . ?
O5' C21' N3' 123.1(5) . . ?
O5' C21' C22' 127.7(5) . . ?
N3' C21' C22' 109.0(4) . . ?
C20' C22' C25' 107.7(5) . . ?
C21' C22' C20' 112.2(4) . . ?
C21' C22' C25' 108.5(5) . . ?
C23' C22' C20' 114.0(4) . . ?
C23' C22' C21' 102.9(4) . . ?
C23' C22' C25' 111.4(5) . . ?
O6' C23' C22' 127.8(5) . . ?
O6' C23' C24' 123.5(5) . . ?
C22' C23' C24' 108.6(4) . . ?
O7' C24' N3' 127.0(5) . . ?
O7' C24' C23' 127.8(4) . . ?
N3' C24' C23' 105.3(4) . . ?
C22' C25' H25C 107.1 . . ?
C22' C25' H25D 107.1 . . ?
H25C C25' H25D 106.8 . . ?
C26' C25' C22' 120.8(9) . . ?
C26' C25' H25C 107.1 . . ?
C26' C25' H25D 107.1 . . ?
C25' C26' H26D 109.5 . . ?
C25' C26' H26E 109.5 . . ?
C25' C26' H26F 109.5 . . ?
H26D C26' H26E 109.5 . . ?
H26D C26' H26F 109.5 . . ?
H26E C26' H26F 109.5 . . ?
C32' C27' N3' 120.3(3) . . ?
C32' C27' C28' 120.0 . . ?
C28' C27' N3' 119.7(3) . . ?
C27' C32' H32' 120.0 . . ?
C27' C32' C31' 120.0 . . ?
C31' C32' H32' 120.0 . . ?
C32' C31' H31' 120.0 . . ?
C32' C31' C30' 120.0 . . ?
C30' C31' H31' 120.0 . . ?
C31' C30' H30' 120.0 . . ?
C29' C30' C31' 120.0 . . ?
C29' C30' H30' 120.0 . . ?
C30' C29' H29' 120.0 . . ?
C30' C29' C28' 120.0 . . ?
C28' C29' H29' 120.0 . . ?
C27' C28' H28' 120.0 . . ?
C29' C28' C27' 120.0 . . ?
C29' C28' H28' 120.0 . . ?

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 C5 C4 C3 -178.3(7) . . . . ?
O1 C8 C9 N1 -179.2(5) . . . . ?
O1 C8 C9 C10 -0.5(6) . . . . ?
O2 N1 C9 C8 -1.2(7) . . . . ?
O2 N1 C9 C10 -180.0(4) . . . . ?
O3 N2 C19 C18 -0.3(7) . . . . ?
O3 N2 C19 C20 -179.5(4) . . . . ?
O4 C15 C16 C11 -179.4(3) . . . . ?
O4 C15 C16 C17 0.9(4) . . . . ?
O4 C18 C19 N2 178.9(4) . . . . ?
O4 C18 C19 C20 -1.8(6) . . . . ?
O5 C21 C22 C20 -47.7(7) . . . . ?
O5 C21 C22 C23 -172.0(5) . . . . ?
O5 C21 C22 C25 72.0(7) . . . . ?
O6 C23 C24 O7 -0.9(8) . . . . ?
O6 C23 C24 N3 178.9(4) . . . . ?
N1 C9 C10 O3 109.2(5) . . . . ?
N2 O3 C10 C9 142.6(4) . . . . ?
N2 C19 C20 C22 -3.5(6) . . . . ?
N3 C21 C22 C20 133.8(4) . . . . ?
N3 C21 C22 C23 9.6(5) . . . . ?
N3 C21 C22 C25 -106.4(6) . . . . ?
N3 C27 C28 C29 -177.4(5) . . . . ?
N3 C27 C32 C31 177.5(4) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C6 C7 C8 O1 0.2(7) . . . . ?
C6 C7 C8 C9 175.9(5) . . . . ?
C5 O1 C8 C7 0.2(7) . . . . ?
C5 O1 C8 C9 -176.6(5) . . . . ?
C5 C6 C1 C2 0.0 . . . . ?
C5 C6 C7 C8 -0.5(6) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C3 C2 C1 C6 0.0 . . . . ?
C1 C6 C5 O1 178.6(6) . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C1 C6 C7 C8 -178.1(5) . . . . ?
C7 C6 C5 O1 0.6(6) . . . . ?
C7 C6 C5 C4 -178.0(5) . . . . ?
C7 C6 C1 C2 177.3(7) . . . . ?
C7 C8 C9 N1 5.3(9) . . . . ?
C7 C8 C9 C10 -176.0(6) . . . . ?
C8 O1 C5 C6 -0.5(6) . . . . ?
C8 O1 C5 C4 178.0(4) . . . . ?
C8 C9 C10 O3 -69.7(6) . . . . ?
C10 O3 N2 C19 179.2(4) . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C11 C16 C17 C18 179.1(3) . . . . ?
C12 C11 C16 C15 0.0 . . . . ?
C12 C11 C16 C17 179.7(5) . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 O4 179.3(4) . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C11 0.0 . . . . ?
C14 C15 C16 C17 -179.8(4) . . . . ?
C15 O4 C18 C17 -0.5(5) . . . . ?
C15 O4 C18 C19 177.7(3) . . . . ?
C15 C16 C17 C18 -1.2(5) . . . . ?
C16 C11 C12 C13 0.0 . . . . ?
C16 C17 C18 O4 1.1(5) . . . . ?
C16 C17 C18 C19 -176.6(5) . . . . ?
C17 C18 C19 N2 -3.4(9) . . . . ?
C17 C18 C19 C20 175.9(5) . . . . ?
C18 O4 C15 C14 -179.6(3) . . . . ?
C18 O4 C15 C16 -0.2(4) . . . . ?
C18 C19 C20 C22 177.1(4) . . . . ?
C19 C20 C22 C21 -63.8(6) . . . . ?
C19 C20 C22 C23 54.1(6) . . . . ?
C19 C20 C22 C25 177.6(5) . . . . ?
C20 C22 C23 O6 52.9(7) . . . . ?
C20 C22 C23 C24 -130.2(4) . . . . ?
C20 C22 C25 C26 173.6(9) . . . . ?
C21 N3 C24 O7 -175.7(5) . . . . ?
C21 N3 C24 C23 4.5(5) . . . . ?
C21 N3 C27 C28 79.8(5) . . . . ?
C21 N3 C27 C32 -97.6(5) . . . . ?
C21 C22 C23 O6 176.4(5) . . . . ?
C21 C22 C23 C24 -6.7(5) . . . . ?
C21 C22 C25 C26 51.0(11) . . . . ?
C22 C23 C24 O7 -178.0(5) . . . . ?
C22 C23 C24 N3 1.8(5) . . . . ?
C23 C22 C25 C26 -60.3(10) . . . . ?
C24 N3 C21 O5 172.2(4) . . . . ?
C24 N3 C21 C22 -9.2(5) . . . . ?
C24 N3 C27 C28 -98.0(5) . . . . ?
C24 N3 C27 C32 84.5(5) . . . . ?
C25 C22 C23 O6 -69.9(7) . . . . ?
C25 C22 C23 C24 106.9(5) . . . . ?
C27 N3 C21 O5 -5.9(7) . . . . ?
C27 N3 C21 C22 172.7(4) . . . . ?
C27 N3 C24 O7 2.4(7) . . . . ?
C27 N3 C24 C23 -177.4(4) . . . . ?
C27 C28 C29 C30 0.0 . . . . ?
C28 C27 C32 C31 0.0 . . . . ?
C28 C29 C30 C31 0.0 . . . . ?
C29 C30 C31 C32 0.0 . . . . ?
C30 C31 C32 C27 0.0 . . . . ?
C32 C27 C28 C29 0.0 . . . . ?
O1' C5' C6' C1' 179.3(4) . . . . ?
O1' C5' C6' C7' -1.4(5) . . . . ?
O1' C5' C4' C3' -179.2(5) . . . . ?
O1' C8' C9' N1' -176.4(5) . . . . ?
O1' C8' C9' C10' 6.3(6) . . . . ?
O2' N1' C9' C8' 0.6(7) . . . . ?
O2' N1' C9' C10' 178.1(4) . . . . ?
O3' N2' C19' C18' 1.0(7) . . . . ?
O3' N2' C19' C20' -179.5(4) . . . . ?
O4' C15' C16' C11' -178.6(4) . . . . ?
O4' C15' C16' C17' 0.6(4) . . . . ?
O4' C15' C14' C13' 178.3(5) . . . . ?
O4' C18' C19' N2' -178.4(5) . . . . ?
O4' C18' C19' C20' 2.1(6) . . . . ?
O5' C21' C22' C20' -52.7(7) . . . . ?
O5' C21' C22' C23' -175.8(5) . . . . ?
O5' C21' C22' C25' 66.1(8) . . . . ?
O6' C23' C24' O7' 0.8(7) . . . . ?
O6' C23' C24' N3' 179.5(4) . . . . ?
N1' C9' C10' O3' 110.4(5) . . . . ?
N2' O3' C10' C9' 143.9(4) . . . . ?
N2' C19' C20' C22' -0.1(7) . . . . ?
N3' C21' C22' C20' 133.2(4) . . . . ?
N3' C21' C22' C23' 10.1(5) . . . . ?
N3' C21' C22' C25' -108.0(5) . . . . ?
N3' C27' C32' C31' -179.0(4) . . . . ?
N3' C27' C28' C29' 179.0(4) . . . . ?
C5' O1' C8' C7' -0.3(5) . . . . ?
C5' O1' C8' C9' -177.8(4) . . . . ?
C5' C6' C1' C2' 0.0 . . . . ?
C5' C6' C7' C8' 1.2(5) . . . . ?
C6' C5' C4' C3' 0.0 . . . . ?
C6' C1' C2' C3' 0.0 . . . . ?
C6' C7' C8' O1' -0.6(6) . . . . ?
C6' C7' C8' C9' 176.2(5) . . . . ?
C1' C6' C7' C8' -179.7(4) . . . . ?
C1' C2' C3' C4' 0.0 . . . . ?
C2' C3' C4' C5' 0.0 . . . . ?
C4' C5' C6' C1' 0.0 . . . . ?
C4' C5' C6' C7' 179.3(4) . . . . ?
C7' C6' C1' C2' -179.0(6) . . . . ?
C7' C8' C9' N1' 6.9(9) . . . . ?
C7' C8' C9' C10' -170.4(5) . . . . ?
C8' O1' C5' C6' 1.1(5) . . . . ?
C8' O1' C5' C4' -179.7(3) . . . . ?
C8' C9' C10' O3' -71.9(6) . . . . ?
C10' O3' N2' C19' -179.4(4) . . . . ?
C15' O4' C18' C17' 1.6(6) . . . . ?
C15' O4' C18' C19' 179.0(4) . . . . ?
C15' C16' C11' C12' 0.0 . . . . ?
C15' C16' C17' C18' 0.4(5) . . . . ?
C16' C15' C14' C13' 0.0 . . . . ?
C16' C11' C12' C13' 0.0 . . . . ?
C16' C17' C18' O4' -1.2(6) . . . . ?
C16' C17' C18' C19' -177.8(5) . . . . ?
C11' C16' C17' C18' 179.4(4) . . . . ?
C11' C12' C13' C14' 0.0 . . . . ?
C12' C13' C14' C15' 0.0 . . . . ?
C14' C15' C16' C11' 0.0 . . . . ?
C14' C15' C16' C17' 179.2(4) . . . . ?
C17' C16' C11' C12' -178.8(6) . . . . ?
C17' C18' C19' N2' -1.9(10) . . . . ?
C17' C18' C19' C20' 178.6(6) . . . . ?
C18' O4' C15' C16' -1.3(4) . . . . ?
C18' O4' C15' C14' -179.8(3) . . . . ?
C18' C19' C20' C22' 179.5(4) . . . . ?
C19' C20' C22' C21' -61.0(6) . . . . ?
C19' C20' C22' C23' 55.5(6) . . . . ?
C19' C20' C22' C25' 179.7(5) . . . . ?
C20' C22' C23' O6' 53.4(6) . . . . ?
C20' C22' C23' C24' -128.6(4) . . . . ?
C20' C22' C25' C26' 174.1(8) . . . . ?
C21' N3' C24' O7' -175.8(5) . . . . ?
C21' N3' C24' C23' 5.4(5) . . . . ?
C21' N3' C27' C32' -121.5(5) . . . . ?
C21' N3' C27' C28' 59.5(5) . . . . ?
C21' C22' C23' O6' 175.2(5) . . . . ?
C21' C22' C23' C24' -6.8(5) . . . . ?
C21' C22' C25' C26' 52.5(10) . . . . ?
C22' C23' C24' O7' -177.3(5) . . . . ?
C22' C23' C24' N3' 1.4(4) . . . . ?
C23' C22' C25' C26' -60.1(10) . . . . ?
C24' N3' C21' O5' 175.4(5) . . . . ?
C24' N3' C21' C22' -10.1(5) . . . . ?
C24' N3' C27' C32' 64.9(5) . . . . ?
C24' N3' C27' C28' -114.0(4) . . . . ?
C25' C22' C23' O6' -68.8(7) . . . . ?
C25' C22' C23' C24' 109.2(5) . . . . ?
C27' N3' C21' O5' 1.3(7) . . . . ?
C27' N3' C21' C22' 175.7(4) . . . . ?
C27' N3' C24' O7' -1.7(7) . . . . ?
C27' N3' C24' C23' 179.6(3) . . . . ?
C27' C32' C31' C30' 0.0 . . . . ?
C32' C27' C28' C29' 0.0 . . . . ?
C32' C31' C30' C29' 0.0 . . . . ?
C31' C30' C29' C28' 0.0 . . . . ?
C30' C29' C28' C27' 0.0 . . . . ?
C28' C27' C32' C31' 0.0 . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.333 0.333 -0.173 1347.5 304.8 ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.813
