# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_EE-NA
_database_code_depnum_ccdc_archive 'CCDC 1938507'
loop_
_audit_author_name
_audit_author_address
'Rongkai Du'
;South China University of Technology
China
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-10-03 downloaded from the CCDC.
;
_audit_creation_date             2019-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H24 O2, C6 H6 N2 O'
_chemical_formula_sum            'C26 H30 N2 O3'
_chemical_formula_weight         418.52
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   10.9589(7)
_cell_length_b                   7.4707(4)
_cell_length_c                   14.1977(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.603(6)
_cell_angle_gamma                90
_cell_volume                     1146.09(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2964
_cell_measurement_temperature    298(10)
_cell_measurement_theta_max      28.2720
_cell_measurement_theta_min      3.4840
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9260
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.796
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.129
_diffrn_reflns_theta_min         3.091
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  35.00   1.00    5.00    --   16.81 -57.00   0.00   87
  2  ω     14.00  44.00   1.00    5.00    --   16.81 -77.00 120.00   30
  3  ω    -24.00  57.00   1.00    5.00    --   16.81 -99.00-120.00   81
  4  ω    -18.00  81.00   1.00    5.00    --   16.81  19.00-180.00   99
  5  ω    -23.00  23.00   1.00    5.00    --  -17.43 -99.00   0.00   46
  6  ω     54.00  90.00   1.00    5.00    --   16.81 178.00  30.00   36
;
_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      0.0024751000
_diffrn_orient_matrix_UB_12      0.0000345000
_diffrn_orient_matrix_UB_13      -0.0495632000
_diffrn_orient_matrix_UB_21      0.0653038000
_diffrn_orient_matrix_UB_22      0.0094710000
_diffrn_orient_matrix_UB_23      0.0102793000
_diffrn_orient_matrix_UB_31      0.0065464000
_diffrn_orient_matrix_UB_32      -0.0945005000
_diffrn_orient_matrix_UB_33      0.0010058000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_full    0.913
_reflns_Friedel_fraction_max     0.698
_reflns_number_gt                4234
_reflns_number_total             4914
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1555 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.6(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4914
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.042
_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)+(0.0400P)²+0.1298P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0963
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B),
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C23(H23), C24(H24), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
2.e :
 C21(H21)
;
_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
C1 C 0.9200(2) 0.5755(4) 0.83460(17) 0.0385(6) Uani 1 1 d . . . . .
H1 H 0.9396 0.6830 0.8665 0.046 Uiso 1 1 calc R . . . .
O1 O 0.93868(18) 0.3853(3) 0.60296(13) 0.0465(5) Uani 1 1 d . . . . .
H1A H 0.902(3) 0.296(5) 0.578(2) 0.067(11) Uiso 1 1 d . . . . .
C2 C 0.9437(2) 0.5576(4) 0.74207(18) 0.0426(6) Uani 1 1 d . . . . .
H2 H 0.9781 0.6517 0.7125 0.051 Uiso 1 1 calc R . . . .
O2 O 0.62445(16) 0.6573(3) 1.27802(13) 0.0411(4) Uani 1 1 d . . . . .
H2A H 0.600(3) 0.618(5) 1.332(3) 0.072(11) Uiso 1 1 d . . . . .
C3 C 0.9154(2) 0.3979(4) 0.69472(16) 0.0360(6) Uani 1 1 d . . . . .
C4 C 0.8645(2) 0.2597(3) 0.73946(17) 0.0355(5) Uani 1 1 d . . . . .
H4 H 0.8464 0.1520 0.7073 0.043 Uiso 1 1 calc R . . . .
C5 C 0.8397(2) 0.2785(3) 0.83209(17) 0.0315(5) Uani 1 1 d . . . . .
C6 C 0.7786(3) 0.1232(3) 0.87410(18) 0.0436(6) Uani 1 1 d . . . . .
H6A H 0.8203 0.0134 0.8615 0.052 Uiso 1 1 calc R . . . .
H6B H 0.6934 0.1145 0.8422 0.052 Uiso 1 1 calc R . . . .
C7 C 0.7804(2) 0.1390(3) 0.98068(17) 0.0390(6) Uani 1 1 d . . . . .
H7A H 0.8619 0.1075 1.0145 0.047 Uiso 1 1 calc R . . . .
H7B H 0.7211 0.0559 0.9999 0.047 Uiso 1 1 calc R . . . .
C8 C 0.7484(2) 0.3285(3) 1.00726(16) 0.0301(5) Uani 1 1 d . . . . .
H8 H 0.6690 0.3617 0.9687 0.036 Uiso 1 1 calc R . . . .
C9 C 0.8479(2) 0.4595(3) 0.98455(16) 0.0307(5) Uani 1 1 d . . . . .
H9 H 0.9255 0.4225 1.0244 0.037 Uiso 1 1 calc R . . . .
C10 C 0.8680(2) 0.4392(3) 0.88141(16) 0.0307(5) Uani 1 1 d . . . . .
C11 C 0.8244(2) 0.6523(3) 1.01399(18) 0.0384(6) Uani 1 1 d . . . . .
H11A H 0.8944 0.7261 1.0052 0.046 Uiso 1 1 calc R . . . .
H11B H 0.7518 0.6984 0.9726 0.046 Uiso 1 1 calc R . . . .
C12 C 0.8047(2) 0.6667(3) 1.11796(17) 0.0376(6) Uani 1 1 d . . . . .
H12A H 0.8813 0.6383 1.1601 0.045 Uiso 1 1 calc R . . . .
H12B H 0.7822 0.7887 1.1311 0.045 Uiso 1 1 calc R . . . .
C13 C 0.70318(19) 0.5396(3) 1.13794(15) 0.0298(5) Uani 1 1 d . . . . .
C14 C 0.7377(2) 0.3483(3) 1.11206(16) 0.0316(5) Uani 1 1 d . . . . .
H14 H 0.8203 0.3248 1.1484 0.038 Uiso 1 1 calc R . . . .
C15 C 0.6481(3) 0.2277(4) 1.1549(2) 0.0494(7) Uani 1 1 d . . . . .
H15A H 0.6864 0.1137 1.1745 0.059 Uiso 1 1 calc R . . . .
H15B H 0.5734 0.2064 1.1091 0.059 Uiso 1 1 calc R . . . .
C16 C 0.6188(3) 0.3324(4) 1.24160(19) 0.0455(7) Uani 1 1 d . . . . .
H16A H 0.6454 0.2655 1.3000 0.055 Uiso 1 1 calc R . . . .
H16B H 0.5306 0.3543 1.2352 0.055 Uiso 1 1 calc R . . . .
C17 C 0.6904(2) 0.5121(3) 1.24390(16) 0.0338(5) Uani 1 1 d . . . . .
C18 C 0.5773(2) 0.5993(4) 1.08276(19) 0.0497(7) Uani 1 1 d . . . . .
H18A H 0.5148 0.5152 1.0934 0.075 Uiso 1 1 calc GR . . . .
H18B H 0.5812 0.6046 1.0158 0.075 Uiso 1 1 calc GR . . . .
H18C H 0.5572 0.7156 1.1046 0.075 Uiso 1 1 calc GR . . . .
C20 C 0.8112(2) 0.4936(4) 1.30688(17) 0.0389(6) Uani 1 1 d . . . . .
C21 C 0.9038(3) 0.4784(4) 1.3615(2) 0.0554(8) Uani 1 1 d . . . . .
H21 H 0.9771 0.4664 1.4047 0.066 Uiso 1 1 calc R . . . .
N1 N 0.5527(2) 0.5552(3) 1.44849(17) 0.0516(6) Uani 1 1 d . . . . .
N2 N 0.2130(2) 0.4249(4) 1.60840(18) 0.0489(6) Uani 1 1 d . . . . .
O3 O 0.18369(17) 0.5843(3) 1.47365(14) 0.0590(6) Uani 1 1 d . . . . .
C22 C 0.3907(2) 0.5157(3) 1.54056(16) 0.0333(5) Uani 1 1 d . . . . .
C23 C 0.4333(2) 0.5462(4) 1.45585(18) 0.0442(6) Uani 1 1 d . . . . .
H23 H 0.3752 0.5613 1.4007 0.053 Uiso 1 1 calc R . . . .
C24 C 0.6340(3) 0.5362(4) 1.5280(2) 0.0551(8) Uani 1 1 d . . . . .
H24 H 0.7177 0.5428 1.5239 0.066 Uiso 1 1 calc R . . . .
C25 C 0.6018(2) 0.5075(4) 1.6162(2) 0.0490(7) Uani 1 1 d . . . . .
H25 H 0.6621 0.4970 1.6703 0.059 Uiso 1 1 calc R . . . .
C26 C 0.4777(2) 0.4947(3) 1.62253(18) 0.0389(6) Uani 1 1 d . . . . .
H26 H 0.4529 0.4722 1.6809 0.047 Uiso 1 1 calc R . . . .
C27 C 0.2536(2) 0.5101(4) 1.53849(17) 0.0373(5) Uani 1 1 d . . . . .
H2B H 0.138(4) 0.415(5) 1.606(3) 0.079(12) Uiso 1 1 d . . . . .
H2C H 0.263(3) 0.351(5) 1.646(2) 0.067(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
C1 H1 0.9300 . ?
C1 C2 1.388(3) . ?
C1 C10 1.389(3) . ?
O1 H1A 0.83(4) . ?
O1 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(4) . ?
O2 H2A 0.90(4) . ?
O2 C17 1.432(3) . ?
C3 C4 1.378(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(3) . ?
C5 C6 1.511(3) . ?
C5 C10 1.398(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.515(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.521(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.538(3) . ?
C8 C14 1.519(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.524(3) . ?
C9 C11 1.533(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.531(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.525(3) . ?
C13 C14 1.539(3) . ?
C13 C17 1.548(3) . ?
C13 C18 1.535(3) . ?
C14 H14 0.9800 . ?
C14 C15 1.531(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.537(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.552(4) . ?
C17 C20 1.475(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 C21 1.175(4) . ?
C21 H21 0.9300 . ?
N1 C23 1.331(3) . ?
N1 C24 1.324(4) . ?
N2 C27 1.318(3) . ?
N2 H2B 0.82(4) . ?
N2 H2C 0.89(4) . ?
O3 C27 1.227(3) . ?
C22 C23 1.379(3) . ?
C22 C26 1.385(3) . ?
C22 C27 1.499(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.373(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.382(3) . ?
C26 H26 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 C1 H1 118.7 . . ?
C2 C1 C10 122.6(2) . . ?
C10 C1 H1 118.7 . . ?
C3 O1 H1A 108(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H2 120.6 . . ?
C17 O2 H2A 106(2) . . ?
O1 C3 C2 117.3(2) . . ?
O1 C3 C4 122.7(2) . . ?
C4 C3 C2 119.9(2) . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.1(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 117.6(2) . . ?
C4 C5 C10 119.8(2) . . ?
C10 C5 C6 122.5(2) . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
C5 C6 C7 113.7(2) . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 C8 110.8(2) . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C7 C8 H8 108.4 . . ?
C7 C8 C9 109.86(19) . . ?
C9 C8 H8 108.4 . . ?
C14 C8 C7 113.08(19) . . ?
C14 C8 H8 108.4 . . ?
C14 C8 C9 108.48(18) . . ?
C8 C9 H9 106.1 . . ?
C10 C9 C8 111.05(17) . . ?
C10 C9 H9 106.1 . . ?
C10 C9 C11 114.39(18) . . ?
C11 C9 C8 112.52(18) . . ?
C11 C9 H9 106.1 . . ?
C1 C10 C5 117.7(2) . . ?
C1 C10 C9 121.6(2) . . ?
C5 C10 C9 120.73(19) . . ?
C9 C11 H11A 109.0 . . ?
C9 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C9 112.7(2) . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 C11 111.12(19) . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C12 C13 C14 108.55(18) . . ?
C12 C13 C17 116.80(18) . . ?
C12 C13 C18 110.2(2) . . ?
C14 C13 C17 100.04(18) . . ?
C18 C13 C14 112.6(2) . . ?
C18 C13 C17 108.39(18) . . ?
C8 C14 C13 112.73(18) . . ?
C8 C14 H14 106.4 . . ?
C8 C14 C15 119.4(2) . . ?
C13 C14 H14 106.4 . . ?
C15 C14 C13 104.61(19) . . ?
C15 C14 H14 106.4 . . ?
C14 C15 H15A 110.8 . . ?
C14 C15 H15B 110.8 . . ?
C14 C15 C16 104.6(2) . . ?
H15A C15 H15B 108.9 . . ?
C16 C15 H15A 110.8 . . ?
C16 C15 H15B 110.8 . . ?
C15 C16 H16A 110.4 . . ?
C15 C16 H16B 110.4 . . ?
C15 C16 C17 106.5(2) . . ?
H16A C16 H16B 108.6 . . ?
C17 C16 H16A 110.4 . . ?
C17 C16 H16B 110.4 . . ?
O2 C17 C13 111.15(19) . . ?
O2 C17 C16 112.36(19) . . ?
O2 C17 C20 108.57(19) . . ?
C13 C17 C16 102.82(18) . . ?
C20 C17 C13 112.57(18) . . ?
C20 C17 C16 109.3(2) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C20 C17 176.1(3) . . ?
C20 C21 H21 180.0 . . ?
C24 N1 C23 117.3(2) . . ?
C27 N2 H2B 118(3) . . ?
C27 N2 H2C 120(2) . . ?
H2B N2 H2C 119(3) . . ?
C23 C22 C26 117.8(2) . . ?
C23 C22 C27 118.1(2) . . ?
C26 C22 C27 124.1(2) . . ?
N1 C23 C22 123.8(2) . . ?
N1 C23 H23 118.1 . . ?
C22 C23 H23 118.1 . . ?
N1 C24 H24 118.1 . . ?
N1 C24 C25 123.7(2) . . ?
C25 C24 H24 118.1 . . ?
C24 C25 H25 120.8 . . ?
C24 C25 C26 118.4(2) . . ?
C26 C25 H25 120.8 . . ?
C22 C26 H26 120.5 . . ?
C25 C26 C22 119.0(2) . . ?
C25 C26 H26 120.5 . . ?
N2 C27 C22 117.5(2) . . ?
O3 C27 N2 122.4(2) . . ?
O3 C27 C22 120.1(2) . . ?

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
O1 H1A O3 0.83(4) 1.92(4) 2.748(3) 177(3) 2_647
O2 H2A N1 0.90(4) 1.87(4) 2.774(3) 175(3) .
C4 H4 O3 0.93 2.58 3.258(3) 129.7 2_647
N2 H2B O1 0.82(4) 2.19(4) 3.009(3) 178(4) 1_456
N2 H2C O2 0.89(4) 2.08(4) 2.968(3) 174(3) 2_648

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 O1 179.3(2) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
O1 C3 C4 C5 -178.7(2) . . . . ?
C2 C1 C10 C5 0.3(4) . . . . ?
C2 C1 C10 C9 177.4(2) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 177.3(2) . . . . ?
C3 C4 C5 C10 -0.7(3) . . . . ?
C4 C5 C6 C7 167.6(2) . . . . ?
C4 C5 C10 C1 0.3(3) . . . . ?
C4 C5 C10 C9 -176.8(2) . . . . ?
C5 C6 C7 C8 43.2(3) . . . . ?
C6 C5 C10 C1 -177.7(2) . . . . ?
C6 C5 C10 C9 5.2(3) . . . . ?
C6 C7 C8 C9 -63.7(3) . . . . ?
C6 C7 C8 C14 174.9(2) . . . . ?
C7 C8 C9 C10 52.9(2) . . . . ?
C7 C8 C9 C11 -177.4(2) . . . . ?
C7 C8 C14 C13 -179.0(2) . . . . ?
C7 C8 C14 C15 -55.6(3) . . . . ?
C8 C9 C10 C1 158.5(2) . . . . ?
C8 C9 C10 C5 -24.5(3) . . . . ?
C8 C9 C11 C12 52.0(3) . . . . ?
C8 C14 C15 C16 -156.1(2) . . . . ?
C9 C8 C14 C13 58.9(2) . . . . ?
C9 C8 C14 C15 -177.7(2) . . . . ?
C9 C11 C12 C13 -53.5(3) . . . . ?
C10 C1 C2 C3 -0.4(4) . . . . ?
C10 C5 C6 C7 -14.4(3) . . . . ?
C10 C9 C11 C12 179.99(19) . . . . ?
C11 C9 C10 C1 29.8(3) . . . . ?
C11 C9 C10 C5 -153.2(2) . . . . ?
C11 C12 C13 C14 56.3(3) . . . . ?
C11 C12 C13 C17 168.4(2) . . . . ?
C11 C12 C13 C18 -67.4(3) . . . . ?
C12 C13 C14 C8 -61.1(2) . . . . ?
C12 C13 C14 C15 167.6(2) . . . . ?
C12 C13 C17 O2 79.9(2) . . . . ?
C12 C13 C17 C16 -159.7(2) . . . . ?
C12 C13 C17 C20 -42.2(3) . . . . ?
C13 C14 C15 C16 -28.8(3) . . . . ?
C14 C8 C9 C10 177.01(19) . . . . ?
C14 C8 C9 C11 -53.3(3) . . . . ?
C14 C13 C17 O2 -163.30(18) . . . . ?
C14 C13 C17 C16 -42.9(2) . . . . ?
C14 C13 C17 C20 74.7(2) . . . . ?
C14 C15 C16 C17 1.4(3) . . . . ?
C15 C16 C17 O2 145.8(2) . . . . ?
C15 C16 C17 C13 26.2(3) . . . . ?
C15 C16 C17 C20 -93.6(3) . . . . ?
C17 C13 C14 C8 176.08(18) . . . . ?
C17 C13 C14 C15 44.8(2) . . . . ?
C18 C13 C14 C8 61.2(3) . . . . ?
C18 C13 C14 C15 -70.1(2) . . . . ?
C18 C13 C17 O2 -45.3(3) . . . . ?
C18 C13 C17 C16 75.1(2) . . . . ?
C18 C13 C17 C20 -167.3(2) . . . . ?
N1 C24 C25 C26 1.1(5) . . . . ?
C23 N1 C24 C25 0.3(5) . . . . ?
C23 C22 C26 C25 0.9(4) . . . . ?
C23 C22 C27 N2 157.9(3) . . . . ?
C23 C22 C27 O3 -22.6(4) . . . . ?
C24 N1 C23 C22 -1.1(4) . . . . ?
C24 C25 C26 C22 -1.6(4) . . . . ?
C26 C22 C23 N1 0.5(4) . . . . ?
C26 C22 C27 N2 -23.1(4) . . . . ?
C26 C22 C27 O3 156.4(3) . . . . ?
C27 C22 C23 N1 179.6(3) . . . . ?
C27 C22 C26 C25 -178.1(2) . . . . ?

_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 1.573
_oxdiff_exptl_absorpt_empirical_full_min 0.606
####################################################################### 
# 
# 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_EE-IZ
_database_code_depnum_ccdc_archive 'CCDC 1938511'
loop_
_audit_author_name
_audit_author_address
'Rongkai Du'
;South China University of Technology
China
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-10-03 downloaded from the CCDC.
;
_audit_creation_date             2019-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H24 O2, C3 H4 N2'
_chemical_formula_sum            'C23 H28 N2 O2'
_chemical_formula_weight         364.47
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.5213(7)
_cell_length_b                   9.9194(6)
_cell_length_c                   24.5146(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2072.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3042
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0090
_cell_measurement_theta_min      3.8880
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.168
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12511
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.535
_diffrn_reflns_theta_min         3.563
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      6.00  53.00   1.00    3.13    --  -16.43  19.00 -30.00   47
  2  ω      1.00  82.00   1.00    3.13    --   15.65  19.00  60.00   81
  3  ω    -25.00   0.00   1.00    3.13    --  -16.43 -99.00-120.00   25
  4  ω      5.00  31.00   1.00    3.13    --   15.65 -57.00-180.00   26
  5  ω    -33.00  -7.00   1.00    3.13    --  -16.43  57.00 -30.00   26
  6  ω    -46.00  -3.00   1.00    3.13    --  -16.43  19.00 -30.00   43
  7  ω     43.00  72.00   1.00    3.13    --   15.65 178.00 -90.00   29
;
_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      -0.0559144000
_diffrn_orient_matrix_UB_12      0.0442378000
_diffrn_orient_matrix_UB_13      0.0117424000
_diffrn_orient_matrix_UB_21      -0.0192278000
_diffrn_orient_matrix_UB_22      0.0246989000
_diffrn_orient_matrix_UB_23      -0.0263426000
_diffrn_orient_matrix_UB_31      -0.0585840000
_diffrn_orient_matrix_UB_32      -0.0503795000
_diffrn_orient_matrix_UB_33      -0.0025924000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.789
_reflns_number_gt                3259
_reflns_number_total             4885
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.108
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1056 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4885
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.018
_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)+(0.0439P)²+0.2026P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1169
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B),
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
2.e :
 C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.4713(3) -0.3461(3) -0.40274(10) 0.0509(7) Uani 1 1 d . . . . .
H1 H -0.3965 -0.3221 -0.3769 0.061 Uiso 1 1 calc R . . . .
O1 O -0.4851(3) -0.4194(2) -0.54752(8) 0.0688(6) Uani 1 1 d . . . . .
H1A H -0.565(5) -0.453(4) -0.5674(14) 0.091(13) Uiso 1 1 d . . . . .
C2 C -0.4247(3) -0.3632(3) -0.45629(11) 0.0540(7) Uani 1 1 d . . . . .
H2 H -0.3203 -0.3511 -0.4662 0.065 Uiso 1 1 calc R . . . .
O2 O -0.8012(3) -0.4807(2) -0.11509(8) 0.0670(6) Uani 1 1 d . . . . .
H2A H -0.705(5) -0.458(4) -0.1044(16) 0.103(15) Uiso 1 1 d . . . . .
C3 C -0.5355(4) -0.3986(3) -0.49491(10) 0.0519(7) Uani 1 1 d . . . . .
C4 C -0.6897(4) -0.4112(3) -0.47994(10) 0.0507(6) Uani 1 1 d . . . . .
H4 H -0.7643 -0.4320 -0.5063 0.061 Uiso 1 1 calc R . . . .
C5 C -0.7372(3) -0.3936(3) -0.42615(10) 0.0458(6) Uani 1 1 d . . . . .
C6 C -0.9093(3) -0.4086(3) -0.41341(11) 0.0573(7) Uani 1 1 d . . . . .
H6A H -0.9375 -0.5032 -0.4152 0.069 Uiso 1 1 calc R . . . .
H6B H -0.9699 -0.3611 -0.4408 0.069 Uiso 1 1 calc R . . . .
C7 C -0.9519(4) -0.3541(3) -0.35738(10) 0.0548(7) Uani 1 1 d . . . . .
H7A H -1.0572 -0.3825 -0.3477 0.066 Uiso 1 1 calc R . . . .
H7B H -0.9495 -0.2564 -0.3579 0.066 Uiso 1 1 calc R . . . .
C8 C -0.8353(3) -0.4069(3) -0.31538(9) 0.0448(6) Uani 1 1 d . . . . .
H8 H -0.8274 -0.5047 -0.3201 0.054 Uiso 1 1 calc R . . . .
C9 C -0.6733(3) -0.3464(2) -0.32656(10) 0.0443(6) Uani 1 1 d . . . . .
H9 H -0.6822 -0.2493 -0.3200 0.053 Uiso 1 1 calc R . . . .
C10 C -0.6261(3) -0.3634(2) -0.38605(10) 0.0433(6) Uani 1 1 d . . . . .
C11 C -0.5513(3) -0.4003(3) -0.28565(10) 0.0544(7) Uani 1 1 d . . . . .
H11A H -0.5355 -0.4958 -0.2920 0.065 Uiso 1 1 calc R . . . .
H11B H -0.4519 -0.3550 -0.2918 0.065 Uiso 1 1 calc R . . . .
C12 C -0.6017(3) -0.3787(3) -0.22603(11) 0.0564(7) Uani 1 1 d . . . . .
H12A H -0.5259 -0.4210 -0.2020 0.068 Uiso 1 1 calc R . . . .
H12B H -0.6031 -0.2830 -0.2180 0.068 Uiso 1 1 calc R . . . .
C13 C -0.7643(3) -0.4382(2) -0.21520(10) 0.0470(7) Uani 1 1 d . . . . .
C14 C -0.8813(3) -0.3799(3) -0.25639(10) 0.0468(6) Uani 1 1 d . . . . .
H14 H -0.8787 -0.2819 -0.2516 0.056 Uiso 1 1 calc R . . . .
C15 C -1.0414(3) -0.4265(3) -0.23577(11) 0.0592(8) Uani 1 1 d . . . . .
H15A H -1.0657 -0.5163 -0.2490 0.071 Uiso 1 1 calc R . . . .
H15B H -1.1235 -0.3651 -0.2472 0.071 Uiso 1 1 calc R . . . .
C16 C -1.0228(4) -0.4257(3) -0.17312(12) 0.0657(8) Uani 1 1 d . . . . .
H16A H -1.0550 -0.5117 -0.1580 0.079 Uiso 1 1 calc R . . . .
H16B H -1.0871 -0.3553 -0.1572 0.079 Uiso 1 1 calc R . . . .
C17 C -0.8469(3) -0.3995(3) -0.16083(10) 0.0556(7) Uani 1 1 d . . . . .
C18 C -0.7551(4) -0.5927(3) -0.21808(13) 0.0658(8) Uani 1 1 d . . . . .
H18A H -0.7203 -0.6194 -0.2537 0.099 Uiso 1 1 calc GR . . . .
H18B H -0.8570 -0.6303 -0.2111 0.099 Uiso 1 1 calc GR . . . .
H18C H -0.6823 -0.6248 -0.1912 0.099 Uiso 1 1 calc GR . . . .
C20 C -0.8192(4) -0.2575(3) -0.14702(12) 0.0661(8) Uani 1 1 d . . . . .
C21 C -0.7933(5) -0.1460(4) -0.13451(16) 0.0946(12) Uani 1 1 d . . . . .
H21 H -0.7728 -0.0572 -0.1246 0.113 Uiso 1 1 calc R . . . .
N1 N -0.5263(4) -0.3997(4) -0.07353(12) 0.0850(8) Uani 1 1 d . . . . .
N2 N -0.2816(4) -0.4148(4) -0.05037(15) 0.0907(10) Uani 1 1 d . . . . .
H2B H -0.186(6) -0.456(5) -0.038(2) 0.15(2) Uiso 1 1 d . . . . .
C22 C -0.4086(5) -0.4791(4) -0.06691(15) 0.0825(10) Uani 1 1 d . . . . .
H22 H -0.4125 -0.5716 -0.0731 0.099 Uiso 1 1 calc R . . . .
C23 C -0.3194(7) -0.2841(5) -0.0451(2) 0.1230(17) Uani 1 1 d . . . . .
H23 H -0.2548 -0.2142 -0.0335 0.148 Uiso 1 1 calc R . . . .
C24 C -0.4701(6) -0.2760(5) -0.0601(2) 0.1131(15) Uani 1 1 d . . . . .
H24 H -0.5283 -0.1966 -0.0611 0.136 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
C1 H1 0.9300 . ?
C1 C2 1.382(4) . ?
C1 C10 1.391(4) . ?
O1 H1A 0.90(4) . ?
O1 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(4) . ?
O2 H2A 0.89(4) . ?
O2 C17 1.434(3) . ?
C3 C4 1.370(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(3) . ?
C5 C6 1.507(4) . ?
C5 C10 1.397(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.520(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.523(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.530(4) . ?
C8 C14 1.522(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.522(4) . ?
C9 C11 1.540(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.538(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.530(4) . ?
C13 C14 1.532(4) . ?
C13 C17 1.555(4) . ?
C13 C18 1.535(3) . ?
C14 H14 0.9800 . ?
C14 C15 1.526(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.544(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.550(4) . ?
C17 C20 1.468(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 C21 1.169(4) . ?
C21 H21 0.9300 . ?
N1 C22 1.286(5) . ?
N1 C24 1.358(5) . ?
N2 H2B 0.96(5) . ?
N2 C22 1.320(5) . ?
N2 C23 1.342(5) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.338(7) . ?
C24 H24 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 C1 H1 118.8 . . ?
C2 C1 C10 122.5(3) . . ?
C10 C1 H1 118.8 . . ?
C3 O1 H1A 109(2) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C17 O2 H2A 110(2) . . ?
O1 C3 C2 117.9(3) . . ?
C4 C3 O1 122.5(3) . . ?
C4 C3 C2 119.6(2) . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 117.9(2) . . ?
C4 C5 C10 119.8(2) . . ?
C10 C5 C6 122.3(2) . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C5 C6 C7 112.6(2) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C6 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
C6 C7 C8 109.4(2) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C7 C8 H8 107.7 . . ?
C7 C8 C9 109.4(2) . . ?
C9 C8 H8 107.7 . . ?
C14 C8 C7 114.4(2) . . ?
C14 C8 H8 107.7 . . ?
C14 C8 C9 109.5(2) . . ?
C8 C9 H9 106.6 . . ?
C8 C9 C11 110.9(2) . . ?
C10 C9 C8 111.5(2) . . ?
C10 C9 H9 106.6 . . ?
C10 C9 C11 114.0(2) . . ?
C11 C9 H9 106.6 . . ?
C1 C10 C5 117.5(2) . . ?
C1 C10 C9 121.2(2) . . ?
C5 C10 C9 121.2(2) . . ?
C9 C11 H11A 109.1 . . ?
C9 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C9 112.5(2) . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 C11 111.4(2) . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C12 C13 C14 109.2(2) . . ?
C12 C13 C17 117.6(2) . . ?
C12 C13 C18 109.3(2) . . ?
C14 C13 C17 100.2(2) . . ?
C14 C13 C18 112.3(2) . . ?
C18 C13 C17 108.0(2) . . ?
C8 C14 C13 113.1(2) . . ?
C8 C14 H14 106.4 . . ?
C8 C14 C15 119.4(2) . . ?
C13 C14 H14 106.4 . . ?
C15 C14 C13 104.4(2) . . ?
C15 C14 H14 106.4 . . ?
C14 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
C14 C15 C16 103.7(2) . . ?
H15A C15 H15B 109.0 . . ?
C16 C15 H15A 111.0 . . ?
C16 C15 H15B 111.0 . . ?
C15 C16 H16A 110.3 . . ?
C15 C16 H16B 110.3 . . ?
C15 C16 C17 107.1(2) . . ?
H16A C16 H16B 108.6 . . ?
C17 C16 H16A 110.3 . . ?
C17 C16 H16B 110.3 . . ?
O2 C17 C13 114.1(2) . . ?
O2 C17 C16 108.7(2) . . ?
O2 C17 C20 108.3(2) . . ?
C16 C17 C13 103.3(2) . . ?
C20 C17 C13 111.2(2) . . ?
C20 C17 C16 111.2(3) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C20 C17 177.5(4) . . ?
C20 C21 H21 180.0 . . ?
C22 N1 C24 104.4(4) . . ?
C22 N2 H2B 126(3) . . ?
C22 N2 C23 107.4(4) . . ?
C23 N2 H2B 126(3) . . ?
N1 C22 N2 112.5(4) . . ?
N1 C22 H22 123.8 . . ?
N2 C22 H22 123.8 . . ?
N2 C23 H23 127.4 . . ?
C24 C23 N2 105.2(4) . . ?
C24 C23 H23 127.4 . . ?
N1 C24 H24 124.8 . . ?
C23 C24 N1 110.5(4) . . ?
C23 C24 H24 124.8 . . ?

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
O1 H1A O2 0.90(4) 1.76(4) 2.653(3) 171(3) 2_344
O2 H2A N1 0.89(4) 1.80(4) 2.678(4) 171(4) .
N2 H2B O1 0.96(5) 1.93(5) 2.806(4) 152(4) 2_445

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 O1 -177.9(2) . . . . ?
C1 C2 C3 C4 2.4(4) . . . . ?
O1 C3 C4 C5 178.1(2) . . . . ?
C2 C1 C10 C5 -2.7(4) . . . . ?
C2 C1 C10 C9 178.8(2) . . . . ?
C2 C3 C4 C5 -2.2(4) . . . . ?
C3 C4 C5 C6 179.7(3) . . . . ?
C3 C4 C5 C10 -0.5(4) . . . . ?
C4 C5 C6 C7 -165.9(2) . . . . ?
C4 C5 C10 C1 2.9(4) . . . . ?
C4 C5 C10 C9 -178.7(2) . . . . ?
C5 C6 C7 C8 -47.4(3) . . . . ?
C6 C5 C10 C1 -177.3(3) . . . . ?
C6 C5 C10 C9 1.2(4) . . . . ?
C6 C7 C8 C9 66.9(3) . . . . ?
C6 C7 C8 C14 -169.8(2) . . . . ?
C7 C8 C9 C10 -50.4(3) . . . . ?
C7 C8 C9 C11 -178.6(2) . . . . ?
C7 C8 C14 C13 178.1(2) . . . . ?
C7 C8 C14 C15 54.7(3) . . . . ?
C8 C9 C10 C1 -164.4(2) . . . . ?
C8 C9 C10 C5 17.2(3) . . . . ?
C8 C9 C11 C12 -54.3(3) . . . . ?
C8 C14 C15 C16 161.7(2) . . . . ?
C9 C8 C14 C13 -58.6(3) . . . . ?
C9 C8 C14 C15 178.0(2) . . . . ?
C9 C11 C12 C13 54.1(3) . . . . ?
C10 C1 C2 C3 0.1(4) . . . . ?
C10 C5 C6 C7 14.3(4) . . . . ?
C10 C9 C11 C12 178.9(2) . . . . ?
C11 C9 C10 C1 -37.8(3) . . . . ?
C11 C9 C10 C5 143.8(2) . . . . ?
C11 C12 C13 C14 -54.4(3) . . . . ?
C11 C12 C13 C17 -167.6(2) . . . . ?
C11 C12 C13 C18 68.9(3) . . . . ?
C12 C13 C14 C8 58.0(3) . . . . ?
C12 C13 C14 C15 -170.6(2) . . . . ?
C12 C13 C17 O2 -84.1(3) . . . . ?
C12 C13 C17 C16 158.1(2) . . . . ?
C12 C13 C17 C20 38.8(3) . . . . ?
C13 C14 C15 C16 34.1(3) . . . . ?
C14 C8 C9 C10 -176.57(19) . . . . ?
C14 C8 C9 C11 55.2(3) . . . . ?
C14 C13 C17 O2 157.7(2) . . . . ?
C14 C13 C17 C16 40.0(3) . . . . ?
C14 C13 C17 C20 -79.4(3) . . . . ?
C14 C15 C16 C17 -8.2(3) . . . . ?
C15 C16 C17 O2 -141.5(2) . . . . ?
C15 C16 C17 C13 -20.0(3) . . . . ?
C15 C16 C17 C20 99.4(3) . . . . ?
C17 C13 C14 C8 -177.8(2) . . . . ?
C17 C13 C14 C15 -46.4(3) . . . . ?
C18 C13 C14 C8 -63.4(3) . . . . ?
C18 C13 C14 C15 68.0(3) . . . . ?
C18 C13 C17 O2 40.1(3) . . . . ?
C18 C13 C17 C16 -77.7(3) . . . . ?
C18 C13 C17 C20 163.0(3) . . . . ?
N2 C23 C24 N1 1.1(6) . . . . ?
C22 N1 C24 C23 -0.6(6) . . . . ?
C22 N2 C23 C24 -1.1(6) . . . . ?
C23 N2 C22 N1 0.9(5) . . . . ?
C24 N1 C22 N2 -0.2(5) . . . . ?

_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 1.208
_oxdiff_exptl_absorpt_empirical_full_min 0.785
####################################################################### 
# 
# 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_EE-PZ
_database_code_depnum_ccdc_archive 'CCDC 1938508'
loop_
_audit_author_name
_audit_author_address
'Rongkai Du'
;South China University of Technology
China
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-10-03 downloaded from the CCDC.
;
_audit_creation_date             2019-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H24 O2, 2(C2 H5 N)'
_chemical_formula_sum            'C24 H34 N2 O2'
_chemical_formula_weight         382.53
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
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                   11.9146(13)
_cell_length_b                   6.9435(8)
_cell_length_c                   26.361(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.921(10)
_cell_angle_gamma                90
_cell_volume                     2179.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1339
_cell_measurement_temperature    173.00(15)
_cell_measurement_theta_max      26.4000
_cell_measurement_theta_min      3.6950
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.166
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.824
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            5217
_diffrn_reflns_point_group_measured_fraction_full 0.786
_diffrn_reflns_point_group_measured_fraction_max 0.615
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.394
_diffrn_reflns_theta_min         3.396
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      173.00(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.824
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  65.00   1.00    7.50    --   15.49   0.00   0.00   94
  2  ω      8.00  77.00   1.00    7.50    --   15.49  38.00  60.00   69
  3  ω     58.00  88.00   1.00    7.50    --   15.49 178.00 -30.00   30
  4  ω    -23.00   5.00   1.00    7.50    --  -16.28-102.00 -39.00   28
;
_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      -0.0237395000
_diffrn_orient_matrix_UB_12      0.0052729000
_diffrn_orient_matrix_UB_13      -0.0250033000
_diffrn_orient_matrix_UB_21      0.0262326000
_diffrn_orient_matrix_UB_22      -0.0884975000
_diffrn_orient_matrix_UB_23      -0.0060232000
_diffrn_orient_matrix_UB_31      -0.0479596000
_diffrn_orient_matrix_UB_32      -0.0508293000
_diffrn_orient_matrix_UB_33      0.0078858000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.385
_reflns_Friedel_fraction_full    0.533
_reflns_Friedel_fraction_max     0.371
_reflns_number_gt                2898
_reflns_number_total             3725
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.524
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 723 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3725
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0629
_refine_ls_restrained_S_all      1.054
_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)+(0.0736P)²+1.5555P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1570
_refine_ls_wR_factor_ref         0.1717
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1B
 0.86 with sigma of 0.01
3. Others
 Sof(H25C)=Sof(H25D)=Sof(H24C)=Sof(H24D)=Sof(N2B)=Sof(H2B)=1-FVAR(1)
 Sof(H25A)=Sof(H25B)=Sof(H24A)=Sof(H24B)=Sof(N2A)=Sof(H2AA)=FVAR(1)
4.a Everything fixed:
 H1B
4.b Ternary CH refined with riding coordinates:
 C14(H14), C9(H9), C8(H8)
4.c Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C15(H15A,H15B), C12(H12A,H12B), C11(H11A,H11B), C7(H7A,H7B),
 C6(H6A,H6B), C23(H23A,H23B), C22(H22A,H22B), C25(H25C,H25D), C25(H25A,H25B),
 C24(H24C,H24D), C24(H24A,H24B)
4.d Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2A), C4(H4)
4.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
4.f :
 C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
C21 C 0.6818(5) 0.1817(10) 0.90236(19) 0.0699(15) Uani 1 1 d . . . . .
H21 H 0.6758 0.0558 0.9139 0.084 Uiso 1 1 calc R . . . .
O2 O 0.6853(3) 0.6780(6) 0.90578(12) 0.0591(10) Uani 1 1 d . . . . .
H2 H 0.631(6) 0.675(12) 0.920(2) 0.10(3) Uiso 1 1 d . . . . .
C20 C 0.6895(4) 0.3431(8) 0.88753(16) 0.0529(11) Uani 1 1 d . . . . .
O1 O 0.3330(3) 0.3149(6) 0.52811(11) 0.0592(9) Uani 1 1 d . . . . .
H1 H 0.252(5) 0.301(9) 0.528(2) 0.09(2) Uiso 1 1 d . . . . .
C17 C 0.7039(3) 0.5398(7) 0.86747(16) 0.0451(10) Uani 1 1 d . . . . .
C16 C 0.8262(3) 0.5615(7) 0.84873(16) 0.0519(12) Uani 1 1 d . . . . .
H16A H 0.8517 0.6935 0.8527 0.062 Uiso 1 1 calc R . . . .
H16B H 0.8770 0.4779 0.8680 0.062 Uiso 1 1 calc R . . . .
C15 C 0.8219(3) 0.5038(7) 0.79202(16) 0.0473(11) Uani 1 1 d . . . . .
H15A H 0.8426 0.6115 0.7709 0.057 Uiso 1 1 calc R . . . .
H15B H 0.8723 0.3972 0.7860 0.057 Uiso 1 1 calc R . . . .
C14 C 0.6984(3) 0.4443(6) 0.78093(14) 0.0375(9) Uani 1 1 d . . . . .
H14 H 0.6916 0.3117 0.7931 0.045 Uiso 1 1 calc R . . . .
C13 C 0.6330(3) 0.5699(6) 0.81750(15) 0.0395(9) Uani 1 1 d . . . . .
C18 C 0.6352(4) 0.7848(7) 0.80415(17) 0.0494(11) Uani 1 1 d . . . . .
H18A H 0.7112 0.8305 0.8060 0.074 Uiso 1 1 calc GR . . . .
H18B H 0.5911 0.8552 0.8277 0.074 Uiso 1 1 calc GR . . . .
H18C H 0.6045 0.8031 0.7703 0.074 Uiso 1 1 calc GR . . . .
C12 C 0.5107(3) 0.5005(8) 0.81743(15) 0.0472(11) Uani 1 1 d . . . . .
H12A H 0.5078 0.3728 0.8323 0.057 Uiso 1 1 calc R . . . .
H12B H 0.4671 0.5865 0.8380 0.057 Uiso 1 1 calc R . . . .
C11 C 0.4594(3) 0.4946(7) 0.76341(14) 0.0424(10) Uani 1 1 d . . . . .
H11A H 0.3841 0.4416 0.7643 0.051 Uiso 1 1 calc R . . . .
H11B H 0.4534 0.6250 0.7504 0.051 Uiso 1 1 calc R . . . .
C9 C 0.5287(3) 0.3739(6) 0.72754(14) 0.0368(9) Uani 1 1 d . . . . .
H9 H 0.5313 0.2434 0.7417 0.044 Uiso 1 1 calc R . . . .
C8 C 0.6509(3) 0.4449(6) 0.72691(14) 0.0351(8) Uani 1 1 d . . . . .
H8 H 0.6508 0.5778 0.7144 0.042 Uiso 1 1 calc R . . . .
C7 C 0.7158(3) 0.3224(8) 0.69090(14) 0.0469(10) Uani 1 1 d . . . . .
H7A H 0.7116 0.1886 0.7012 0.056 Uiso 1 1 calc R . . . .
H7B H 0.7942 0.3607 0.6925 0.056 Uiso 1 1 calc R . . . .
C6 C 0.6697(3) 0.3428(8) 0.63667(15) 0.0459(10) Uani 1 1 d . . . . .
H6A H 0.6968 0.4627 0.6227 0.055 Uiso 1 1 calc R . . . .
H6B H 0.6988 0.2384 0.6165 0.055 Uiso 1 1 calc R . . . .
C5 C 0.5427(3) 0.3406(6) 0.63183(14) 0.0370(8) Uani 1 1 d . . . . .
C10 C 0.4759(3) 0.3564(6) 0.67433(14) 0.0363(8) Uani 1 1 d . . . . .
C1 C 0.3603(3) 0.3543(7) 0.66576(15) 0.0432(10) Uani 1 1 d . . . . .
H1A H 0.3144 0.3640 0.6935 0.052 Uiso 1 1 calc R . . . .
C2 C 0.3107(3) 0.3388(7) 0.61824(15) 0.0472(10) Uani 1 1 d . . . . .
H2A H 0.2328 0.3370 0.6144 0.057 Uiso 1 1 calc R . . . .
C3 C 0.3763(3) 0.3257(6) 0.57599(14) 0.0421(9) Uani 1 1 d . . . . .
C4 C 0.4923(3) 0.3240(7) 0.58371(14) 0.0415(9) Uani 1 1 d . . . . .
H4 H 0.5376 0.3115 0.5558 0.050 Uiso 1 1 calc R . . . .
N1 N 0.4657(4) 0.6545(13) 0.94848(18) 0.108(2) Uani 1 1 d D . . . .
C23 C 0.4538(6) 0.8186(13) 0.9809(2) 0.092(2) Uani 1 1 d . . . . .
H23A H 0.3824 0.8129 0.9975 0.110 Uiso 1 1 calc R . . . .
H23B H 0.4557 0.9360 0.9610 0.110 Uiso 1 1 calc R . . . .
C22 C 0.4537(6) 0.4720(14) 0.9813(3) 0.111(3) Uani 1 1 d . . . . .
H22A H 0.3825 0.4734 0.9981 0.134 Uiso 1 1 calc R . . . .
H22B H 0.4566 0.3576 0.9603 0.134 Uiso 1 1 calc R . . . .
C25 C 0.0895(4) 0.3186(10) 0.46657(18) 0.0646(14) Uani 1 1 d . . . . .
H25C H 0.1327 0.2444 0.4429 0.077 Uiso 0.490(17) 1 calc R . P A 2
H25D H 0.1176 0.4496 0.4662 0.077 Uiso 0.490(17) 1 calc R . P A 2
H25A H 0.1153 0.1861 0.4668 0.06(3) Uiso 0.510(17) 1 calc R . P A 1
H25B H 0.1334 0.3878 0.4422 0.06(3) Uiso 0.510(17) 1 calc R . P A 1
C24 C 0.0320(4) 0.3203(9) 0.55224(16) 0.0563(12) Uani 1 1 d . . . . .
H24C H 0.0537 0.4518 0.5601 0.068 Uiso 0.490(17) 1 calc R . P A 2
H24D H 0.0385 0.2463 0.5834 0.068 Uiso 0.490(17) 1 calc R . P A 2
H24A H 0.0381 0.3984 0.5827 0.05(3) Uiso 0.510(17) 1 calc R . P A 1
H24B H 0.0538 0.1900 0.5614 0.04(2) Uiso 0.510(17) 1 calc R . P A 1
N2A N 0.1131(7) 0.3966(15) 0.5142(3) 0.050(3) Uani 0.510(17) 1 d . . P A 1
H2AA H 0.122(11) 0.52(2) 0.505(5) 0.10(5) Uiso 0.510(17) 1 d . . P A 1
N2B N 0.1092(6) 0.2418(15) 0.5161(3) 0.050(3) Uani 0.490(17) 1 d . . P A 2
H2B H 0.087(6) 0.113(13) 0.507(3) 0.02(2) Uiso 0.490(17) 1 d . . P A 2
H1B H 0.3973 0.6410 0.9356 0.476 Uiso 1 1 d 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
C21 H21 0.9300 . ?
C21 C20 1.191(8) . ?
O2 H2 0.76(7) . ?
O2 C17 1.416(5) . ?
C20 C17 1.476(7) . ?
O1 H1 0.96(6) . ?
O1 C3 1.349(4) . ?
C17 C16 1.562(6) . ?
C17 C13 1.555(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.547(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.546(5) . ?
C14 H14 0.9800 . ?
C14 C13 1.532(6) . ?
C14 C8 1.515(5) . ?
C13 C18 1.534(6) . ?
C13 C12 1.535(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.531(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C9 1.527(5) . ?
C9 H9 0.9800 . ?
C9 C8 1.538(5) . ?
C9 C10 1.523(5) . ?
C8 H8 0.9800 . ?
C8 C7 1.507(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.521(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.514(5) . ?
C5 C10 1.401(5) . ?
C5 C4 1.390(5) . ?
C10 C1 1.388(5) . ?
C1 H1A 0.9300 . ?
C1 C2 1.371(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.385(6) . ?
C3 C4 1.391(5) . ?
C4 H4 0.9300 . ?
N1 C23 1.435(10) . ?
N1 C22 1.543(11) . ?
N1 H1B 0.8770 . ?
C23 C23 1.466(11) 2_657 ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C22 C22 1.455(14) 2_657 ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C25 H25C 0.9700 . ?
C25 H25D 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C24 1.514(6) 2_556 ?
C25 N2A 1.388(9) . ?
C25 N2B 1.422(10) . ?
C24 C25 1.514(6) 2_556 ?
C24 H24C 0.9700 . ?
C24 H24D 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 N2A 1.512(10) . ?
C24 N2B 1.453(10) . ?
N2A H2AA 0.91(16) . ?
N2B H2B 0.96(9) . ?

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
C20 C21 H21 180.0 . . ?
C17 O2 H2 119(6) . . ?
C21 C20 C17 177.0(5) . . ?
C3 O1 H1 111(3) . . ?
O2 C17 C20 110.4(3) . . ?
O2 C17 C16 109.3(3) . . ?
O2 C17 C13 114.8(4) . . ?
C20 C17 C16 108.9(4) . . ?
C20 C17 C13 111.2(3) . . ?
C13 C17 C16 101.8(3) . . ?
C17 C16 H16A 110.5 . . ?
C17 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
C15 C16 C17 106.2(3) . . ?
C15 C16 H16A 110.5 . . ?
C15 C16 H16B 110.5 . . ?
C16 C15 H15A 110.8 . . ?
C16 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
C14 C15 C16 104.6(3) . . ?
C14 C15 H15A 110.8 . . ?
C14 C15 H15B 110.8 . . ?
C15 C14 H14 106.2 . . ?
C13 C14 C15 103.3(3) . . ?
C13 C14 H14 106.2 . . ?
C8 C14 C15 120.0(3) . . ?
C8 C14 H14 106.2 . . ?
C8 C14 C13 114.1(3) . . ?
C14 C13 C17 100.5(3) . . ?
C14 C13 C18 113.3(3) . . ?
C14 C13 C12 108.9(3) . . ?
C18 C13 C17 108.2(3) . . ?
C18 C13 C12 109.2(4) . . ?
C12 C13 C17 116.6(3) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C11 C12 C13 111.0(3) . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C9 C11 C12 112.5(3) . . ?
C9 C11 H11A 109.1 . . ?
C9 C11 H11B 109.1 . . ?
C11 C9 H9 106.4 . . ?
C11 C9 C8 111.3(3) . . ?
C8 C9 H9 106.4 . . ?
C10 C9 C11 113.5(3) . . ?
C10 C9 H9 106.4 . . ?
C10 C9 C8 112.2(3) . . ?
C14 C8 C9 108.3(3) . . ?
C14 C8 H8 108.3 . . ?
C9 C8 H8 108.3 . . ?
C7 C8 C14 114.0(3) . . ?
C7 C8 C9 109.4(3) . . ?
C7 C8 H8 108.3 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C8 C7 C6 111.3(3) . . ?
H7A C7 H7B 108.0 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C7 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C5 C6 C7 114.0(3) . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C10 C5 C6 121.7(3) . . ?
C4 C5 C6 118.5(3) . . ?
C4 C5 C10 119.8(3) . . ?
C5 C10 C9 121.0(3) . . ?
C1 C10 C9 121.9(3) . . ?
C1 C10 C5 117.2(3) . . ?
C10 C1 H1A 118.5 . . ?
C2 C1 C10 123.0(4) . . ?
C2 C1 H1A 118.5 . . ?
C1 C2 H2A 119.9 . . ?
C1 C2 C3 120.2(4) . . ?
C3 C2 H2A 119.9 . . ?
O1 C3 C2 123.2(4) . . ?
O1 C3 C4 118.9(3) . . ?
C2 C3 C4 117.9(3) . . ?
C5 C4 C3 122.0(3) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C23 N1 C22 107.8(5) . . ?
C23 N1 H1B 101.9 . . ?
C22 N1 H1B 91.5 . . ?
N1 C23 C23 108.8(5) . 2_657 ?
N1 C23 H23A 109.9 . . ?
N1 C23 H23B 109.9 . . ?
C23 C23 H23A 109.9 2_657 . ?
C23 C23 H23B 109.9 2_657 . ?
H23A C23 H23B 108.3 . . ?
N1 C22 H22A 110.3 . . ?
N1 C22 H22B 110.3 . . ?
C22 C22 N1 107.3(5) 2_657 . ?
C22 C22 H22A 110.3 2_657 . ?
C22 C22 H22B 110.3 2_657 . ?
H22A C22 H22B 108.5 . . ?
H25C C25 H25D 107.5 . . ?
H25A C25 H25B 107.3 . . ?
C24 C25 H25C 108.4 2_556 . ?
C24 C25 H25D 108.4 2_556 . ?
C24 C25 H25A 108.0 2_556 . ?
C24 C25 H25B 108.0 2_556 . ?
N2A C25 H25A 108.0 . . ?
N2A C25 H25B 108.0 . . ?
N2A C25 C24 117.1(5) . 2_556 ?
N2B C25 H25C 108.4 . . ?
N2B C25 H25D 108.4 . . ?
N2B C25 C24 115.5(5) . 2_556 ?
C25 C24 H24C 108.8 2_556 . ?
C25 C24 H24D 108.8 2_556 . ?
C25 C24 H24A 108.7 2_556 . ?
C25 C24 H24B 108.7 2_556 . ?
H24C C24 H24D 107.7 . . ?
H24A C24 H24B 107.6 . . ?
N2A C24 C25 114.3(5) . 2_556 ?
N2A C24 H24A 108.7 . . ?
N2A C24 H24B 108.7 . . ?
N2B C24 C25 113.7(5) . 2_556 ?
N2B C24 H24C 108.8 . . ?
N2B C24 H24D 108.8 . . ?
C25 N2A C24 110.4(6) . . ?
C25 N2A H2AA 98(8) . . ?
C24 N2A H2AA 127(8) . . ?
C25 N2B C24 111.9(6) . . ?
C25 N2B H2B 95(5) . . ?
C24 N2B H2B 110(5) . . ?

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 N1 0.76(7) 2.13(7) 2.888(6) 171(7) .
O1 H1 N2A 0.96(6) 1.82(6) 2.694(9) 150(6) .
O1 H1 N2B 0.96(6) 1.77(6) 2.723(9) 167(5) .
C25 H25D O1 0.97 2.61 3.569(8) 171.7 4_556
C25 H25A O1 0.97 2.65 3.619(8) 174.3 4_546
N2A H2AA O1 0.91(16) 2.28(16) 3.184(11) 170(11) 4_556
N2B H2B O1 0.96(9) 2.47(9) 3.267(11) 140(6) 4_546

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 C17 C16 C15 -148.4(4) . . . . ?
O2 C17 C13 C14 162.8(3) . . . . ?
O2 C17 C13 C18 43.8(4) . . . . ?
O2 C17 C13 C12 -79.7(5) . . . . ?
C20 C17 C16 C15 91.0(4) . . . . ?
C20 C17 C13 C14 -70.9(4) . . . . ?
C20 C17 C13 C18 170.0(4) . . . . ?
C20 C17 C13 C12 46.6(5) . . . . ?
O1 C3 C4 C5 178.0(4) . . . . ?
C17 C16 C15 C14 -2.0(5) . . . . ?
C17 C13 C12 C11 -166.7(4) . . . . ?
C16 C17 C13 C14 44.9(4) . . . . ?
C16 C17 C13 C18 -74.1(4) . . . . ?
C16 C17 C13 C12 162.4(4) . . . . ?
C16 C15 C14 C13 30.4(5) . . . . ?
C16 C15 C14 C8 158.7(4) . . . . ?
C15 C14 C13 C17 -47.0(4) . . . . ?
C15 C14 C13 C18 68.3(4) . . . . ?
C15 C14 C13 C12 -170.0(4) . . . . ?
C15 C14 C8 C9 178.3(4) . . . . ?
C15 C14 C8 C7 56.3(5) . . . . ?
C14 C13 C12 C11 -53.9(5) . . . . ?
C14 C8 C7 C6 -175.2(4) . . . . ?
C13 C17 C16 C15 -26.5(5) . . . . ?
C13 C14 C8 C9 -58.4(4) . . . . ?
C13 C14 C8 C7 179.6(4) . . . . ?
C13 C12 C11 C9 54.7(5) . . . . ?
C18 C13 C12 C11 70.4(5) . . . . ?
C12 C11 C9 C8 -55.6(5) . . . . ?
C12 C11 C9 C10 176.7(3) . . . . ?
C11 C9 C8 C14 55.5(4) . . . . ?
C11 C9 C8 C7 -179.7(3) . . . . ?
C11 C9 C10 C5 148.0(4) . . . . ?
C11 C9 C10 C1 -32.3(6) . . . . ?
C9 C8 C7 C6 63.4(5) . . . . ?
C9 C10 C1 C2 180.0(4) . . . . ?
C8 C14 C13 C17 -179.0(3) . . . . ?
C8 C14 C13 C18 -63.7(5) . . . . ?
C8 C14 C13 C12 58.0(5) . . . . ?
C8 C9 C10 C5 20.8(5) . . . . ?
C8 C9 C10 C1 -159.5(4) . . . . ?
C8 C7 C6 C5 -43.1(6) . . . . ?
C7 C6 C5 C10 11.7(6) . . . . ?
C7 C6 C5 C4 -168.8(4) . . . . ?
C6 C5 C10 C9 -0.8(6) . . . . ?
C6 C5 C10 C1 179.5(4) . . . . ?
C6 C5 C4 C3 -178.4(4) . . . . ?
C5 C10 C1 C2 -0.3(7) . . . . ?
C10 C9 C8 C14 -176.1(3) . . . . ?
C10 C9 C8 C7 -51.3(4) . . . . ?
C10 C5 C4 C3 1.1(6) . . . . ?
C10 C1 C2 C3 -0.5(7) . . . . ?
C1 C2 C3 O1 -178.3(4) . . . . ?
C1 C2 C3 C4 1.6(7) . . . . ?
C2 C3 C4 C5 -1.9(7) . . . . ?
C4 C5 C10 C9 179.8(4) . . . . ?
C4 C5 C10 C1 0.1(6) . . . . ?
C23 N1 C22 C22 -63.4(8) . . . 2_657 ?
C22 N1 C23 C23 63.5(7) . . . 2_657 ?
C25 C24 N2A C25 -44.9(8) 2_556 . . . ?
C25 C24 N2B C25 47.5(8) 2_556 . . . ?
C24 C25 N2A C24 47.5(9) 2_556 . . . ?
C24 C25 N2B C24 -47.3(9) 2_556 . . . ?
N2A C25 N2B C24 56.4(8) . . . . ?
N2A C24 N2B C25 -53.2(7) . . . . ?
N2B C25 N2A C24 -52.4(7) . . . . ?
N2B C24 N2A C25 54.3(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.702
_oxdiff_exptl_absorpt_empirical_full_min 0.548
####################################################################### 
# 
# 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_EE-BIP
_database_code_depnum_ccdc_archive 'CCDC 1938510'
loop_
_audit_author_name
_audit_author_address
'Rongkai Du'
;South China University of Technology
China
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-10-03 downloaded from the CCDC.
;
_audit_creation_date             2019-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H24 O2, C10 H8 N2'
_chemical_formula_sum            'C30 H32 N2 O2'
_chemical_formula_weight         452.57
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.3914(7)
_cell_length_b                   13.6642(8)
_cell_length_c                   19.2618(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2471.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5323
_cell_measurement_temperature    173(6)
_cell_measurement_theta_max      26.2910
_cell_measurement_theta_min      3.6520
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20862
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.396
_diffrn_reflns_theta_min         3.506
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      173(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  65.00   1.00    3.17    --   15.65  57.00 -90.00   64
  2  ω    -25.00  41.00   1.00    3.17    --   15.65 -99.00 -30.00   66
  3  ω    -14.00  22.00   1.00    3.17    --  -16.43 -99.00 -30.00   36
  4  ω    -56.00  35.00   1.00    3.17    --   15.65 -19.00 -30.00   91
  5  ω     -3.00  85.00   1.00    3.17    --   15.65  38.00 150.00   88
  6  ω    -25.00  11.00   1.00    3.17    --  -16.43 -99.00 150.00   36
;
_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      -0.0052511000
_diffrn_orient_matrix_UB_12      -0.0516345000
_diffrn_orient_matrix_UB_13      -0.0025978000
_diffrn_orient_matrix_UB_21      0.0716884000
_diffrn_orient_matrix_UB_22      -0.0023354000
_diffrn_orient_matrix_UB_23      -0.0114594000
_diffrn_orient_matrix_UB_31      0.0232661000
_diffrn_orient_matrix_UB_32      -0.0045801000
_diffrn_orient_matrix_UB_33      0.0349004000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.825
_reflns_number_gt                4289
_reflns_number_total             5866
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1477 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5866
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.042
_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)+(0.0566P)²+0.1403P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1208
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B),
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28),
 C29(H29), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
2.e :
 C21(H21)
;
_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
C1 C -0.5070(3) -0.52623(18) -0.02131(12) 0.0450(6) Uani 1 1 d . . . . .
H1 H -0.5088 -0.5519 -0.0660 0.054 Uiso 1 1 calc R . . . .
O1 O -0.5458(3) -0.61569(15) 0.15461(10) 0.0687(6) Uani 1 1 d . . . . .
H1A H -0.518(4) -0.587(3) 0.1961(17) 0.088(11) Uiso 1 1 d . . . . .
C2 C -0.5297(3) -0.58824(19) 0.03412(12) 0.0474(6) Uani 1 1 d . . . . .
H2 H -0.5474 -0.6544 0.0266 0.057 Uiso 1 1 calc R . . . .
O2 O -0.4827(3) -0.12803(16) -0.30075(10) 0.0742(7) Uani 1 1 d . . . . .
H2A H -0.479(5) -0.185(3) -0.3245(17) 0.093(12) Uiso 1 1 d . . . . .
C3 C -0.5261(3) -0.5515(2) 0.10096(12) 0.0487(6) Uani 1 1 d . . . . .
C4 C -0.5057(3) -0.4519(2) 0.11067(12) 0.0499(6) Uani 1 1 d . . . . .
H4 H -0.5069 -0.4264 0.1554 0.060 Uiso 1 1 calc R . . . .
C5 C -0.4837(3) -0.38956(18) 0.05495(11) 0.0425(6) Uani 1 1 d . . . . .
C6 C -0.4668(3) -0.28115(18) 0.06896(12) 0.0492(6) Uani 1 1 d . . . . .
H6A H -0.4121 -0.2724 0.1112 0.059 Uiso 1 1 calc R . . . .
H6B H -0.5601 -0.2526 0.0764 0.059 Uiso 1 1 calc R . . . .
C7 C -0.3934(3) -0.22690(19) 0.01016(12) 0.0514(7) Uani 1 1 d . . . . .
H7A H -0.4000 -0.1569 0.0180 0.062 Uiso 1 1 calc R . . . .
H7B H -0.2933 -0.2446 0.0090 0.062 Uiso 1 1 calc R . . . .
C8 C -0.4619(3) -0.25225(17) -0.05877(11) 0.0406(5) Uani 1 1 d . . . . .
H8 H -0.5643 -0.2395 -0.0549 0.049 Uiso 1 1 calc R . . . .
C9 C -0.4417(3) -0.36191(17) -0.07426(11) 0.0416(6) Uani 1 1 d . . . . .
H9 H -0.3395 -0.3714 -0.0818 0.050 Uiso 1 1 calc R . . . .
C10 C -0.4814(3) -0.42639(17) -0.01277(11) 0.0396(5) Uani 1 1 d . . . . .
C11 C -0.5148(4) -0.39051(19) -0.14216(12) 0.0617(8) Uani 1 1 d . . . . .
H11A H -0.6170 -0.3832 -0.1369 0.074 Uiso 1 1 calc R . . . .
H11B H -0.4952 -0.4588 -0.1520 0.074 Uiso 1 1 calc R . . . .
C12 C -0.4643(4) -0.32759(18) -0.20363(12) 0.0602(8) Uani 1 1 d . . . . .
H12A H -0.3648 -0.3413 -0.2130 0.072 Uiso 1 1 calc R . . . .
H12B H -0.5187 -0.3444 -0.2447 0.072 Uiso 1 1 calc R . . . .
C13 C -0.4824(3) -0.21910(17) -0.18804(12) 0.0469(6) Uani 1 1 d . . . . .
C14 C -0.4054(3) -0.19420(17) -0.12006(11) 0.0422(6) Uani 1 1 d . . . . .
H14 H -0.3059 -0.2140 -0.1263 0.051 Uiso 1 1 calc R . . . .
C15 C -0.4063(4) -0.08224(19) -0.11791(14) 0.0592(8) Uani 1 1 d . . . . .
H15A H -0.3254 -0.0576 -0.0920 0.071 Uiso 1 1 calc R . . . .
H15B H -0.4932 -0.0581 -0.0967 0.071 Uiso 1 1 calc R . . . .
C16 C -0.3975(4) -0.05155(19) -0.19443(14) 0.0662(9) Uani 1 1 d . . . . .
H16A H -0.3086 -0.0176 -0.2034 0.079 Uiso 1 1 calc R . . . .
H16B H -0.4757 -0.0083 -0.2061 0.079 Uiso 1 1 calc R . . . .
C17 C -0.4057(4) -0.14694(18) -0.23828(13) 0.0543(7) Uani 1 1 d . . . . .
C18 C -0.6404(4) -0.1922(3) -0.18632(17) 0.0786(10) Uani 1 1 d . . . . .
H18A H -0.6841 -0.2105 -0.2295 0.118 Uiso 1 1 calc GR . . . .
H18B H -0.6502 -0.1229 -0.1796 0.118 Uiso 1 1 calc GR . . . .
H18C H -0.6861 -0.2262 -0.1489 0.118 Uiso 1 1 calc GR . . . .
C20 C -0.2621(4) -0.18147(19) -0.25604(13) 0.0605(8) Uani 1 1 d . . . . .
C21 C -0.1491(5) -0.2098(2) -0.27215(18) 0.0792(10) Uani 1 1 d . . . . .
H21 H -0.0594 -0.2323 -0.2849 0.095 Uiso 1 1 calc R . . . .
N1 N -0.4839(4) -0.29177(19) -0.39316(13) 0.0713(8) Uani 1 1 d . . . . .
N2 N -0.4806(3) -0.53851(17) -0.71660(11) 0.0606(7) Uani 1 1 d . . . . .
C22 C -0.4794(3) -0.39399(18) -0.51912(13) 0.0480(6) Uani 1 1 d . . . . .
C23 C -0.3584(3) -0.3832(2) -0.47931(15) 0.0647(8) Uani 1 1 d . . . . .
H23 H -0.2726 -0.4103 -0.4938 0.078 Uiso 1 1 calc R . . . .
C24 C -0.3659(4) -0.3319(3) -0.41757(16) 0.0742(10) Uani 1 1 d . . . . .
H24 H -0.2830 -0.3251 -0.3916 0.089 Uiso 1 1 calc R . . . .
C25 C -0.6003(4) -0.3050(2) -0.43087(16) 0.0700(9) Uani 1 1 d . . . . .
H25 H -0.6856 -0.2796 -0.4141 0.084 Uiso 1 1 calc R . . . .
C26 C -0.6029(3) -0.3538(2) -0.49316(14) 0.0596(7) Uani 1 1 d . . . . .
H26 H -0.6877 -0.3596 -0.5177 0.072 Uiso 1 1 calc R . . . .
C27 C -0.4785(3) -0.44571(18) -0.58690(12) 0.0472(6) Uani 1 1 d . . . . .
C28 C -0.3590(3) -0.4468(2) -0.62922(14) 0.0612(8) Uani 1 1 d . . . . .
H28 H -0.2753 -0.4167 -0.6147 0.073 Uiso 1 1 calc R . . . .
C29 C -0.3650(4) -0.4926(2) -0.69282(15) 0.0669(9) Uani 1 1 d . . . . .
H29 H -0.2841 -0.4916 -0.7207 0.080 Uiso 1 1 calc R . . . .
C30 C -0.5927(4) -0.5385(2) -0.67531(14) 0.0589(8) Uani 1 1 d . . . . .
H30 H -0.6740 -0.5710 -0.6905 0.071 Uiso 1 1 calc R . . . .
C31 C -0.5975(3) -0.4939(2) -0.61151(13) 0.0527(7) Uani 1 1 d . . . . .
H31 H -0.6802 -0.4961 -0.5850 0.063 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
C1 H1 0.9300 . ?
C1 C2 1.380(3) . ?
C1 C10 1.395(3) . ?
O1 H1A 0.93(3) . ?
O1 C3 1.368(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(3) . ?
O2 H2A 0.90(4) . ?
O2 C17 1.428(3) . ?
C3 C4 1.387(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(3) . ?
C5 C6 1.514(3) . ?
C5 C10 1.398(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.519(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.516(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.540(3) . ?
C8 C14 1.518(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.522(3) . ?
C9 C11 1.528(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.538(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.522(4) . ?
C13 C14 1.534(3) . ?
C13 C17 1.558(4) . ?
C13 C18 1.529(5) . ?
C14 H14 0.9800 . ?
C14 C15 1.530(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.535(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.555(4) . ?
C17 C20 1.469(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 C21 1.171(5) . ?
C21 H21 0.9300 . ?
N1 C24 1.323(5) . ?
N1 C25 1.325(5) . ?
N2 C29 1.335(4) . ?
N2 C30 1.320(4) . ?
C22 C23 1.379(4) . ?
C22 C26 1.378(4) . ?
C22 C27 1.485(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.383(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C25 C26 1.373(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.387(4) . ?
C27 C31 1.381(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.377(4) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C30 C31 1.373(4) . ?
C31 H31 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 C1 H1 118.8 . . ?
C2 C1 C10 122.4(2) . . ?
C10 C1 H1 118.8 . . ?
C3 O1 H1A 110(2) . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C17 O2 H2A 105(2) . . ?
O1 C3 C2 117.8(2) . . ?
O1 C3 C4 123.1(2) . . ?
C2 C3 C4 119.1(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 118.6(2) . . ?
C4 C5 C10 120.2(2) . . ?
C10 C5 C6 121.1(2) . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C5 C6 C7 113.1(2) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 C6 110.4(2) . . ?
C8 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C7 C8 H8 108.0 . . ?
C7 C8 C9 109.9(2) . . ?
C7 C8 C14 114.4(2) . . ?
C9 C8 H8 108.0 . . ?
C14 C8 H8 108.0 . . ?
C14 C8 C9 108.35(18) . . ?
C8 C9 H9 106.2 . . ?
C10 C9 C8 112.48(18) . . ?
C10 C9 H9 106.2 . . ?
C10 C9 C11 114.07(19) . . ?
C11 C9 C8 111.1(2) . . ?
C11 C9 H9 106.2 . . ?
C1 C10 C5 117.3(2) . . ?
C1 C10 C9 121.10(19) . . ?
C5 C10 C9 121.4(2) . . ?
C9 C11 H11A 109.2 . . ?
C9 C11 H11B 109.2 . . ?
C9 C11 C12 112.2(2) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 C11 111.0(2) . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C12 C13 C14 109.4(2) . . ?
C12 C13 C17 116.2(2) . . ?
C12 C13 C18 110.3(3) . . ?
C14 C13 C17 99.9(2) . . ?
C18 C13 C14 112.7(2) . . ?
C18 C13 C17 108.1(2) . . ?
C8 C14 C13 112.5(2) . . ?
C8 C14 H14 106.5 . . ?
C8 C14 C15 119.9(2) . . ?
C13 C14 H14 106.5 . . ?
C15 C14 C13 104.0(2) . . ?
C15 C14 H14 106.5 . . ?
C14 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
C14 C15 C16 104.3(2) . . ?
H15A C15 H15B 108.9 . . ?
C16 C15 H15A 110.9 . . ?
C16 C15 H15B 110.9 . . ?
C15 C16 H16A 110.4 . . ?
C15 C16 H16B 110.4 . . ?
C15 C16 C17 106.8(2) . . ?
H16A C16 H16B 108.6 . . ?
C17 C16 H16A 110.4 . . ?
C17 C16 H16B 110.4 . . ?
O2 C17 C13 113.8(2) . . ?
O2 C17 C16 109.3(2) . . ?
O2 C17 C20 109.1(2) . . ?
C16 C17 C13 102.5(2) . . ?
C20 C17 C13 111.5(2) . . ?
C20 C17 C16 110.5(3) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C20 C17 178.0(3) . . ?
C20 C21 H21 180.0 . . ?
C24 N1 C25 116.1(3) . . ?
C30 N2 C29 116.3(2) . . ?
C23 C22 C27 122.3(3) . . ?
C26 C22 C23 116.7(2) . . ?
C26 C22 C27 120.9(2) . . ?
C22 C23 H23 120.3 . . ?
C22 C23 C24 119.4(3) . . ?
C24 C23 H23 120.3 . . ?
N1 C24 C23 124.0(3) . . ?
N1 C24 H24 118.0 . . ?
C23 C24 H24 118.0 . . ?
N1 C25 H25 118.0 . . ?
N1 C25 C26 124.1(3) . . ?
C26 C25 H25 118.0 . . ?
C22 C26 H26 120.1 . . ?
C25 C26 C22 119.7(3) . . ?
C25 C26 H26 120.1 . . ?
C28 C27 C22 121.8(3) . . ?
C31 C27 C22 121.6(2) . . ?
C31 C27 C28 116.6(2) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 C27 119.6(3) . . ?
C29 C28 H28 120.2 . . ?
N2 C29 C28 123.5(3) . . ?
N2 C29 H29 118.2 . . ?
C28 C29 H29 118.2 . . ?
N2 C30 H30 117.8 . . ?
N2 C30 C31 124.4(3) . . ?
C31 C30 H30 117.8 . . ?
C27 C31 H31 120.2 . . ?
C30 C31 C27 119.5(3) . . ?
C30 C31 H31 120.2 . . ?

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
O1 H1A N2 0.93(3) 1.84(3) 2.764(3) 173(3) 1_556
O2 H2A N1 0.90(4) 1.97(4) 2.859(3) 168(3) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 O1 -178.5(3) . . . . ?
C1 C2 C3 C4 2.7(4) . . . . ?
O1 C3 C4 C5 178.8(3) . . . . ?
C2 C1 C10 C5 -1.9(4) . . . . ?
C2 C1 C10 C9 173.7(2) . . . . ?
C2 C3 C4 C5 -2.5(4) . . . . ?
C3 C4 C5 C6 178.1(3) . . . . ?
C3 C4 C5 C10 -0.1(4) . . . . ?
C4 C5 C6 C7 159.7(3) . . . . ?
C4 C5 C10 C1 2.2(4) . . . . ?
C4 C5 C10 C9 -173.3(2) . . . . ?
C5 C6 C7 C8 49.4(3) . . . . ?
C6 C5 C10 C1 -175.9(2) . . . . ?
C6 C5 C10 C9 8.6(4) . . . . ?
C6 C7 C8 C9 -63.5(3) . . . . ?
C6 C7 C8 C14 174.4(2) . . . . ?
C7 C8 C9 C10 48.5(3) . . . . ?
C7 C8 C9 C11 177.8(2) . . . . ?
C7 C8 C14 C13 -177.5(2) . . . . ?
C7 C8 C14 C15 -54.7(3) . . . . ?
C8 C9 C10 C1 162.8(2) . . . . ?
C8 C9 C10 C5 -21.8(3) . . . . ?
C8 C9 C11 C12 55.3(3) . . . . ?
C8 C14 C15 C16 -159.3(3) . . . . ?
C9 C8 C14 C13 59.6(3) . . . . ?
C9 C8 C14 C15 -177.6(2) . . . . ?
C9 C11 C12 C13 -54.5(4) . . . . ?
C10 C1 C2 C3 -0.6(4) . . . . ?
C10 C5 C6 C7 -22.2(4) . . . . ?
C10 C9 C11 C12 -176.4(2) . . . . ?
C11 C9 C10 C1 35.2(4) . . . . ?
C11 C9 C10 C5 -149.5(3) . . . . ?
C11 C12 C13 C14 54.9(4) . . . . ?
C11 C12 C13 C17 167.0(3) . . . . ?
C11 C12 C13 C18 -69.6(3) . . . . ?
C12 C13 C14 C8 -59.4(3) . . . . ?
C12 C13 C14 C15 169.3(2) . . . . ?
C12 C13 C17 O2 82.2(3) . . . . ?
C12 C13 C17 C16 -159.9(3) . . . . ?
C12 C13 C17 C20 -41.7(3) . . . . ?
C13 C14 C15 C16 -32.5(3) . . . . ?
C14 C8 C9 C10 174.2(2) . . . . ?
C14 C8 C9 C11 -56.6(3) . . . . ?
C14 C13 C17 O2 -160.4(2) . . . . ?
C14 C13 C17 C16 -42.4(3) . . . . ?
C14 C13 C17 C20 75.7(2) . . . . ?
C14 C15 C16 C17 5.1(4) . . . . ?
C15 C16 C17 O2 144.5(3) . . . . ?
C15 C16 C17 C13 23.5(3) . . . . ?
C15 C16 C17 C20 -95.4(3) . . . . ?
C17 C13 C14 C8 178.1(2) . . . . ?
C17 C13 C14 C15 46.8(3) . . . . ?
C18 C13 C14 C8 63.7(3) . . . . ?
C18 C13 C14 C15 -67.7(3) . . . . ?
C18 C13 C17 O2 -42.4(3) . . . . ?
C18 C13 C17 C16 75.5(3) . . . . ?
C18 C13 C17 C20 -166.3(2) . . . . ?
N1 C25 C26 C22 1.2(5) . . . . ?
N2 C30 C31 C27 -0.6(4) . . . . ?
C22 C23 C24 N1 0.4(5) . . . . ?
C22 C27 C28 C29 -177.6(3) . . . . ?
C22 C27 C31 C30 178.3(2) . . . . ?
C23 C22 C26 C25 0.7(4) . . . . ?
C23 C22 C27 C28 -30.2(4) . . . . ?
C23 C22 C27 C31 150.8(3) . . . . ?
C24 N1 C25 C26 -2.3(5) . . . . ?
C25 N1 C24 C23 1.5(5) . . . . ?
C26 C22 C23 C24 -1.5(4) . . . . ?
C26 C22 C27 C28 149.5(3) . . . . ?
C26 C22 C27 C31 -29.5(4) . . . . ?
C27 C22 C23 C24 178.2(3) . . . . ?
C27 C22 C26 C25 -179.0(3) . . . . ?
C27 C28 C29 N2 -1.0(5) . . . . ?
C28 C27 C31 C30 -0.7(4) . . . . ?
C29 N2 C30 C31 1.0(4) . . . . ?
C30 N2 C29 C28 -0.2(4) . . . . ?
C31 C27 C28 C29 1.4(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 1.225
_oxdiff_exptl_absorpt_empirical_full_min 0.660
####################################################################### 
# 
# 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_EE-TET-H2O
_database_code_depnum_ccdc_archive 'CCDC 1938509'
loop_
_audit_author_name
_audit_author_address
'Rongkai Du'
;South China University of Technology
China
;
_audit_update_record             
;
2019-09-14 deposited with the CCDC.	2019-10-03 downloaded from the CCDC.
;
_audit_creation_date             2019-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H24 O2, H2 O, C8 H12 N2'
_chemical_formula_sum            'C28 H38 N2 O3'
_chemical_formula_weight         450.60
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
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                   7.3836(5)
_cell_length_b                   21.3958(14)
_cell_length_c                   32.4582(19)
_cell_angle_alpha                90
_cell_angle_beta                 94.771(5)
_cell_angle_gamma                90
_cell_volume                     5109.9(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4555
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.9240
_cell_measurement_theta_min      3.5910
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.171
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            19064
_diffrn_reflns_point_group_measured_fraction_full 0.889
_diffrn_reflns_point_group_measured_fraction_max 0.729
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.372
_diffrn_reflns_theta_min         3.357
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  20.20   0.80    5.00    --  -16.28 -99.00 120.00   44
  2  ω     30.00  55.60   0.80    5.00    --   15.49-119.00  36.00   32
  3  ω     30.00  57.20   0.80    5.00    --   15.49-157.00-118.00   34
  4  ω     -3.00  85.00   0.80    5.00    --   15.49  38.00 150.00  110
  5  ω     42.00  69.20   0.80    5.00    --   15.49 178.00   0.00   34
  6  ω     38.00  83.60   0.80    5.00    --   15.49 178.00 -60.00   57
  7  ω     60.00  84.80   0.80    5.00    --   15.49 178.00-150.00   31
  8  ω    -88.00 -63.20   0.80    5.00    --  -16.28 157.00 -83.00   31
  9  ω    -25.00  15.00   0.80    5.00    --  -16.28 -99.00 -90.00   50
;
_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      0.0185237000
_diffrn_orient_matrix_UB_12      -0.0318453000
_diffrn_orient_matrix_UB_13      -0.0040768000
_diffrn_orient_matrix_UB_21      0.0010993000
_diffrn_orient_matrix_UB_22      0.0069257000
_diffrn_orient_matrix_UB_23      -0.0213413000
_diffrn_orient_matrix_UB_31      0.0946091000
_diffrn_orient_matrix_UB_32      0.0061190000
_diffrn_orient_matrix_UB_33      0.0029077000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.657
_reflns_Friedel_fraction_full    0.774
_reflns_Friedel_fraction_max     0.593
_reflns_number_gt                6979
_reflns_number_total             10272
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.377
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 2181 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.7(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     623
_refine_ls_number_reflns         10272
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0680
_refine_ls_restrained_S_all      1.055
_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)+(0.0730P)²+2.1477P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1789
_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, All O(H,H) groups
2. Restrained distances
 H4XA-H1AA_$1
 2.1 with sigma of 0.005
 H3XB-H1AA
 2.1 with sigma of 0.005
 H1BA-H1XA_$2
 2.1 with sigma of 0.005
3. Others
 Fixed Sof: H1XA(0.5) H1XB(0.5) H3XA(0.5) H3XB(0.5) H2XA(0.5) H2XB(0.5)
 O4X(0.5) H4XA(0.5) H4XB(0.5)
4.a Riding coordinates:
 O1X(H1XA,H1XB), O3X(H3XA,H3XB), O2X(H2XA,H2XB), O4X(H4XA,H4XB)
4.b Ternary CH refined with riding coordinates:
 C8A(H8A), C9A(H9A), C14A(H14A), C8B(H8B), C9B(H9B), C14B(H14B)
4.c Secondary CH2 refined with riding coordinates:
 C6A(H6AA,H6AB), C7A(H7AB,H7AA), C11A(H11A,H11B), C12A(H12A,H12B), C15A(H15A,
 H15B), C16A(H16A,H16B), C6B(H6BA,H6BB), C7B(H7BA,H7BB), C11B(H11C,H11D),
 C12B(H12C,H12D), C15B(H15D,H15C), C16B(H16C,H16D)
4.d Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C2A(H2A), C4A(H4A), C1B(H1B), C2B(H2B), C4B(H4B)
4.e Idealised Me refined as rotating group:
 C18A(H18A,H18B,H18C), C18B(H18D,H18E,H18F), C28A(H28A,H28B,H28C), C29A(H29A,
 H29B,H29C), C26A(H26A,H26B,H26C), C27A(H27A,H27B,H27C), C26B(H26D,H26E,H26F),
 C29B(H29D,H29E,H29F), C27B(H27D,H27E,H27F), C28B(H28D,H28E,H28F)
4.f Idealised tetrahedral OH refined as rotating group:
 O1A(H1AA), O1B(H1BA)
4.g :
 C21A(H21A), C21B(H21B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.1072(6) 0.3910(2) 0.84299(14) 0.0460(11) Uani 1 1 d . . . . .
H1A H 0.0022 0.3950 0.8253 0.055 Uiso 1 1 calc R . . . .
O1A O 0.2457(5) 0.40078(15) 0.95289(9) 0.0509(8) Uani 1 1 d . . . . .
H1AA H 0.2731 0.4368 0.9594 0.076 Uiso 1 1 calc DGR . . . .
C2A C 0.0971(6) 0.3996(2) 0.88484(14) 0.0464(11) Uani 1 1 d . . . . .
H2A H -0.0137 0.4093 0.8949 0.056 Uiso 1 1 calc R . . . .
O2A O 0.2940(4) 0.38891(17) 0.61810(10) 0.0493(8) Uani 1 1 d . . . . .
H2AA H 0.345(8) 0.382(3) 0.5946(18) 0.072(18) Uiso 1 1 d . . . . .
C3A C 0.2493(6) 0.3939(2) 0.91149(13) 0.0396(10) Uani 1 1 d . . . . .
C4A C 0.4122(6) 0.3796(2) 0.89576(14) 0.0495(12) Uani 1 1 d . . . . .
H4A H 0.5167 0.3759 0.9137 0.059 Uiso 1 1 calc R . . . .
C5A C 0.4231(6) 0.3708(3) 0.85415(14) 0.0520(12) Uani 1 1 d . . . . .
C6A C 0.5972(8) 0.3538(4) 0.8360(2) 0.093(3) Uani 1 1 d . . . . .
H6AA H 0.6981 0.3625 0.8563 0.112 Uiso 1 1 calc R . . . .
H6AB H 0.5971 0.3093 0.8305 0.112 Uiso 1 1 calc R . . . .
C7A C 0.6260(6) 0.3871(3) 0.79821(16) 0.0622(15) Uani 1 1 d . . . . .
H7AB H 0.7125 0.3634 0.7836 0.075 Uiso 1 1 calc R . . . .
H7AA H 0.6823 0.4269 0.8057 0.075 Uiso 1 1 calc R . . . .
C8A C 0.4612(5) 0.3998(2) 0.76840(12) 0.0381(9) Uani 1 1 d . . . . .
H8A H 0.4364 0.4448 0.7687 0.046 Uiso 1 1 calc R . . . .
C9A C 0.2928(5) 0.3656(2) 0.78143(13) 0.0392(10) Uani 1 1 d . . . . .
H9A H 0.3196 0.3209 0.7790 0.047 Uiso 1 1 calc R . . . .
C10A C 0.2693(5) 0.3766(2) 0.82656(13) 0.0366(9) Uani 1 1 d . . . . .
C11A C 0.1261(6) 0.3774(3) 0.75196(13) 0.0505(13) Uani 1 1 d . . . . .
H11A H 0.0939 0.4213 0.7529 0.061 Uiso 1 1 calc R . . . .
H11B H 0.0249 0.3533 0.7607 0.061 Uiso 1 1 calc R . . . .
C12A C 0.1595(6) 0.3594(3) 0.70770(14) 0.0505(12) Uani 1 1 d . . . . .
H12A H 0.1778 0.3146 0.7062 0.061 Uiso 1 1 calc R . . . .
H12B H 0.0532 0.3700 0.6894 0.061 Uiso 1 1 calc R . . . .
C13A C 0.3250(5) 0.3930(2) 0.69332(13) 0.0368(9) Uani 1 1 d . . . . .
C14A C 0.4879(5) 0.3810(2) 0.72431(13) 0.0396(10) Uani 1 1 d . . . . .
H14A H 0.5058 0.3356 0.7248 0.048 Uiso 1 1 calc R . . . .
C15A C 0.6481(6) 0.4082(3) 0.70308(15) 0.0572(14) Uani 1 1 d . . . . .
H15A H 0.7610 0.3877 0.7126 0.069 Uiso 1 1 calc R . . . .
H15B H 0.6601 0.4527 0.7082 0.069 Uiso 1 1 calc R . . . .
C16A C 0.5977(6) 0.3949(3) 0.65656(14) 0.0505(12) Uani 1 1 d . . . . .
H16A H 0.6811 0.3647 0.6463 0.061 Uiso 1 1 calc R . . . .
H16B H 0.6031 0.4330 0.6406 0.061 Uiso 1 1 calc R . . . .
C17A C 0.4005(6) 0.3683(2) 0.65325(13) 0.0390(10) Uani 1 1 d . . . . .
C18A C 0.2827(8) 0.4629(2) 0.68715(16) 0.0580(14) Uani 1 1 d . . . . .
H18A H 0.3835 0.4832 0.6759 0.087 Uiso 1 1 calc GR . . . .
H18B H 0.2621 0.4815 0.7133 0.087 Uiso 1 1 calc GR . . . .
H18C H 0.1759 0.4677 0.6684 0.087 Uiso 1 1 calc GR . . . .
C20A C 0.4082(7) 0.2991(2) 0.65370(14) 0.0512(12) Uani 1 1 d . . . . .
C21A C 0.4172(9) 0.2443(3) 0.65295(17) 0.0714(17) Uani 1 1 d . . . . .
H21A H 0.4243 0.2010 0.6523 0.086 Uiso 1 1 calc R . . . .
C1B C 0.8407(7) 0.5772(2) 0.65935(15) 0.0491(12) Uani 1 1 d . . . . .
H1B H 0.9282 0.5594 0.6780 0.059 Uiso 1 1 calc R . . . .
O1B O 0.7678(6) 0.60779(17) 0.54850(12) 0.0716(12) Uani 1 1 d . . . . .
H1BA H 0.7305 0.5754 0.5372 0.107 Uiso 1 1 calc DGR . . . .
C2B C 0.8706(7) 0.5803(2) 0.61796(18) 0.0583(14) Uani 1 1 d . . . . .
H2B H 0.9789 0.5653 0.6091 0.070 Uiso 1 1 calc R . . . .
O2B O 0.6931(5) 0.64615(17) 0.88039(12) 0.0575(10) Uani 1 1 d . . . . .
H2BA H 0.645(7) 0.643(2) 0.9025(16) 0.047(14) Uiso 1 1 d . . . . .
C3B C 0.7416(7) 0.6052(2) 0.58998(17) 0.0515(13) Uani 1 1 d . . . . .
C4B C 0.5827(8) 0.6277(2) 0.60371(16) 0.0571(14) Uani 1 1 d . . . . .
H4B H 0.4934 0.6438 0.5847 0.069 Uiso 1 1 calc R . . . .
C5B C 0.5536(7) 0.6267(2) 0.64509(16) 0.0545(13) Uani 1 1 d . . . . .
C6B C 0.3862(10) 0.6557(5) 0.65927(19) 0.118(4) Uani 1 1 d . . . . .
H6BA H 0.3668 0.6948 0.6444 0.142 Uiso 1 1 calc R . . . .
H6BB H 0.2852 0.6285 0.6504 0.142 Uiso 1 1 calc R . . . .
C7B C 0.3743(11) 0.6684(4) 0.7007(2) 0.108(3) Uani 1 1 d . . . . .
H7BA H 0.2782 0.6425 0.7103 0.130 Uiso 1 1 calc R . . . .
H7BB H 0.3365 0.7116 0.7031 0.130 Uiso 1 1 calc R . . . .
C8B C 0.5432(8) 0.6588(2) 0.73028(16) 0.0577(14) Uani 1 1 d . . . . .
H8B H 0.6249 0.6944 0.7279 0.069 Uiso 1 1 calc R . . . .
C9B C 0.6409(6) 0.5993(2) 0.71852(15) 0.0445(11) Uani 1 1 d . . . . .
H9B H 0.5535 0.5653 0.7209 0.053 Uiso 1 1 calc R . . . .
C10B C 0.6807(6) 0.6006(2) 0.67341(15) 0.0448(11) Uani 1 1 d . . . . .
C11B C 0.8033(7) 0.5836(2) 0.74915(15) 0.0515(12) Uani 1 1 d . . . . .
H11C H 0.8973 0.6149 0.7471 0.062 Uiso 1 1 calc R . . . .
H11D H 0.8529 0.5434 0.7420 0.062 Uiso 1 1 calc R . . . .
C12B C 0.7500(7) 0.5813(2) 0.79371(16) 0.0523(12) Uani 1 1 d . . . . .
H12C H 0.6683 0.5464 0.7967 0.063 Uiso 1 1 calc R . . . .
H12D H 0.8580 0.5745 0.8123 0.063 Uiso 1 1 calc R . . . .
C13B C 0.6580(7) 0.6413(2) 0.80557(15) 0.0473(11) Uani 1 1 d . . . . .
C14B C 0.4960(7) 0.6540(2) 0.77413(16) 0.0561(13) Uani 1 1 d . . . . .
H14B H 0.4155 0.6177 0.7752 0.067 Uiso 1 1 calc R . . . .
C15B C 0.3980(11) 0.7085(3) 0.7937(2) 0.092(2) Uani 1 1 d . . . . .
H15D H 0.2687 0.7074 0.7855 0.110 Uiso 1 1 calc R . . . .
H15C H 0.4465 0.7483 0.7855 0.110 Uiso 1 1 calc R . . . .
C16B C 0.4344(9) 0.6985(3) 0.84070(17) 0.0705(16) Uani 1 1 d . . . . .
H16C H 0.3217 0.6905 0.8531 0.085 Uiso 1 1 calc R . . . .
H16D H 0.4917 0.7351 0.8537 0.085 Uiso 1 1 calc R . . . .
C17B C 0.5629(7) 0.6410(2) 0.84606(15) 0.0486(12) Uani 1 1 d . . . . .
C18B C 0.8008(9) 0.6941(3) 0.80840(18) 0.0752(19) Uani 1 1 d . . . . .
H18D H 0.8454 0.7004 0.7818 0.113 Uiso 1 1 calc GR . . . .
H18E H 0.8999 0.6828 0.8280 0.113 Uiso 1 1 calc GR . . . .
H18F H 0.7460 0.7320 0.8172 0.113 Uiso 1 1 calc GR . . . .
C20B C 0.4550(7) 0.5834(2) 0.84908(16) 0.0558(13) Uani 1 1 d . . . . .
C21B C 0.3648(9) 0.5386(3) 0.85184(19) 0.078(2) Uani 1 1 d . . . . .
H21B H 0.2934 0.5031 0.8540 0.094 Uiso 1 1 calc R . . . .
O1X O 0.0000 0.1648(3) 0.5000 0.115(3) Uani 1 2 d S T P . .
H1XA H 0.1046 0.1480 0.5020 0.173 Uiso 0.5 1 d DR . . . .
H1XB H 0.0056 0.2002 0.5119 0.173 Uiso 0.5 1 d R . . . .
N3A N 0.0000 0.2989(2) 0.5000 0.0454(13) Uani 1 2 d S T P . .
N4A N 0.0000 0.4275(2) 0.5000 0.0436(13) Uani 1 2 d S T P . .
C24A C -0.0378(6) 0.3309(2) 0.53349(14) 0.0419(11) Uani 1 1 d . . . . .
C25A C -0.0416(6) 0.3958(2) 0.53332(14) 0.0426(11) Uani 1 1 d . . . . .
C28A C -0.0741(8) 0.2942(2) 0.57132(16) 0.0559(13) Uani 1 1 d . . . . .
H28A H -0.1864 0.3080 0.5812 0.084 Uiso 1 1 calc GR . . . .
H28B H 0.0232 0.3007 0.5924 0.084 Uiso 1 1 calc GR . . . .
H28C H -0.0825 0.2506 0.5646 0.084 Uiso 1 1 calc GR . . . .
C29A C -0.0878(7) 0.4329(2) 0.56983(16) 0.0515(12) Uani 1 1 d . . . . .
H29A H -0.1958 0.4162 0.5802 0.077 Uiso 1 1 calc GR . . . .
H29B H -0.1083 0.4757 0.5618 0.077 Uiso 1 1 calc GR . . . .
H29C H 0.0108 0.4307 0.5910 0.077 Uiso 1 1 calc GR . . . .
N1A N 0.5000 0.0791(3) 1.0000 0.0518(15) Uani 1 2 d S T P . .
N2A N 0.5000 0.2080(2) 1.0000 0.0431(13) Uani 1 2 d S T P . .
O3X O 0.5000 0.3405(3) 1.0000 0.0856(19) Uani 1 2 d S T P . .
H3XA H 0.4535 0.3067 1.0079 0.128 Uiso 0.5 1 d R . . . .
H3XB H 0.4228 0.3598 0.9838 0.128 Uiso 0.5 1 d DR . . . .
C22A C 0.5330(6) 0.1109(2) 0.96613(17) 0.0503(13) Uani 1 1 d . . . . .
C23A C 0.5335(6) 0.1762(2) 0.96589(16) 0.0455(11) Uani 1 1 d . . . . .
C26A C 0.5666(8) 0.0745(3) 0.9285(2) 0.0695(16) Uani 1 1 d . . . . .
H26A H 0.5582 0.0306 0.9343 0.104 Uiso 1 1 calc GR . . . .
H26B H 0.6858 0.0839 0.9204 0.104 Uiso 1 1 calc GR . . . .
H26C H 0.4774 0.0855 0.9065 0.104 Uiso 1 1 calc GR . . . .
C27A C 0.5677(7) 0.2131(3) 0.92850(16) 0.0576(14) Uani 1 1 d . . . . .
H27A H 0.4732 0.2049 0.9070 0.086 Uiso 1 1 calc GR . . . .
H27B H 0.6829 0.2013 0.9192 0.086 Uiso 1 1 calc GR . . . .
H27C H 0.5691 0.2568 0.9352 0.086 Uiso 1 1 calc GR . . . .
N1B N 0.4389(5) 0.37048(18) 0.53890(11) 0.0405(9) Uani 1 1 d . . . . .
C22B C 0.4689(6) 0.3170(2) 0.51969(13) 0.0396(10) Uani 1 1 d . . . . .
C25B C 0.4675(6) 0.4248(2) 0.51934(14) 0.0408(10) Uani 1 1 d . . . . .
C26B C 0.4316(7) 0.2578(2) 0.54139(15) 0.0513(13) Uani 1 1 d . . . . .
H26D H 0.3667 0.2668 0.5651 0.077 Uiso 1 1 calc GR . . . .
H26E H 0.5444 0.2376 0.5501 0.077 Uiso 1 1 calc GR . . . .
H26F H 0.3597 0.2308 0.5230 0.077 Uiso 1 1 calc GR . . . .
C29B C 0.4305(7) 0.4845(2) 0.54126(16) 0.0498(12) Uani 1 1 d . . . . .
H29D H 0.5376 0.5101 0.5430 0.075 Uiso 1 1 calc GR . . . .
H29E H 0.3977 0.4752 0.5686 0.075 Uiso 1 1 calc GR . . . .
H29F H 0.3326 0.5064 0.5262 0.075 Uiso 1 1 calc GR . . . .
O2X O 0.0000 0.5585(3) 0.5000 0.122(3) Uani 1 2 d S T P . .
H2XA H 0.0618 0.5920 0.5011 0.183 Uiso 0.5 1 d R . . . .
H2XB H 0.0747 0.5300 0.4948 0.183 Uiso 0.5 1 d R . . . .
N2B N 0.5564(5) 0.64205(19) 0.96050(12) 0.0447(9) Uani 1 1 d . . . . .
C23B C 0.5295(6) 0.5880(2) 0.98026(15) 0.0423(11) Uani 1 1 d . . . . .
C24B C 0.5282(6) 0.6956(2) 0.98039(15) 0.0435(11) Uani 1 1 d . . . . .
C27B C 0.5667(7) 0.5290(2) 0.95816(17) 0.0556(14) Uani 1 1 d . . . . .
H27D H 0.6197 0.5387 0.9329 0.083 Uiso 1 1 calc GR . . . .
H27E H 0.4550 0.5067 0.9520 0.083 Uiso 1 1 calc GR . . . .
H27F H 0.6493 0.5037 0.9753 0.083 Uiso 1 1 calc GR . . . .
C28B C 0.5629(8) 0.7552(2) 0.95761(16) 0.0542(13) Uani 1 1 d . . . . .
H28D H 0.4562 0.7809 0.9564 0.081 Uiso 1 1 calc GR . . . .
H28E H 0.5919 0.7454 0.9300 0.081 Uiso 1 1 calc GR . . . .
H28F H 0.6628 0.7771 0.9718 0.081 Uiso 1 1 calc GR . . . .
O4X O 0.9903(9) 0.4469(3) 0.98424(18) 0.059(2) Uani 0.5 1 d . . . A -1
H4XA H 0.9316 0.4342 1.0041 0.088 Uiso 0.5 1 d DR . . A -1
H4XB H 0.9835 0.4865 0.9854 0.088 Uiso 0.5 1 d R . . A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A H1A 0.9300 . ?
C1A C2A 1.379(6) . ?
C1A C10A 1.385(6) . ?
O1A H1AA 0.8200 . ?
O1A C3A 1.354(5) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.365(6) . ?
O2A H2AA 0.89(6) . ?
O2A C17A 1.401(6) . ?
C3A C4A 1.380(6) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.373(6) . ?
C5A C6A 1.502(7) . ?
C5A C10A 1.392(7) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C6A C7A 1.450(8) . ?
C7A H7AB 0.9700 . ?
C7A H7AA 0.9700 . ?
C7A C8A 1.515(7) . ?
C8A H8A 0.9800 . ?
C8A C9A 1.532(5) . ?
C8A C14A 1.516(6) . ?
C9A H9A 0.9800 . ?
C9A C10A 1.508(6) . ?
C9A C11A 1.516(6) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C11A C12A 1.527(6) . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C12A C13A 1.524(6) . ?
C13A C14A 1.524(6) . ?
C13A C17A 1.549(6) . ?
C13A C18A 1.539(6) . ?
C14A H14A 0.9800 . ?
C14A C15A 1.533(6) . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
C15A C16A 1.551(7) . ?
C16A H16A 0.9700 . ?
C16A H16B 0.9700 . ?
C16A C17A 1.559(6) . ?
C17A C20A 1.481(7) . ?
C18A H18A 0.9600 . ?
C18A H18B 0.9600 . ?
C18A H18C 0.9600 . ?
C20A C21A 1.174(7) . ?
C21A H21A 0.9300 . ?
C1B H1B 0.9300 . ?
C1B C2B 1.381(7) . ?
C1B C10B 1.394(6) . ?
O1B H1BA 0.8200 . ?
O1B C3B 1.377(6) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.368(8) . ?
O2B H2BA 0.83(5) . ?
O2B C17B 1.414(6) . ?
C3B C4B 1.376(7) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.378(7) . ?
C5B C6B 1.489(7) . ?
C5B C10B 1.376(7) . ?
C6B H6BA 0.9700 . ?
C6B H6BB 0.9700 . ?
C6B C7B 1.383(9) . ?
C7B H7BA 0.9700 . ?
C7B H7BB 0.9700 . ?
C7B C8B 1.522(9) . ?
C8B H8B 0.9800 . ?
C8B C9B 1.526(6) . ?
C8B C14B 1.497(7) . ?
C9B H9B 0.9800 . ?
C9B C10B 1.518(6) . ?
C9B C11B 1.530(7) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C11B C12B 1.531(6) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C12B C13B 1.517(7) . ?
C13B C14B 1.531(7) . ?
C13B C17B 1.541(6) . ?
C13B C18B 1.544(7) . ?
C14B H14B 0.9800 . ?
C14B C15B 1.538(7) . ?
C15B H15D 0.9700 . ?
C15B H15C 0.9700 . ?
C15B C16B 1.541(8) . ?
C16B H16C 0.9700 . ?
C16B H16D 0.9700 . ?
C16B C17B 1.554(8) . ?
C17B C20B 1.475(7) . ?
C18B H18D 0.9600 . ?
C18B H18E 0.9600 . ?
C18B H18F 0.9600 . ?
C20B C21B 1.175(7) . ?
C21B H21B 0.9300 . ?
O1X H1XA 0.8500 . ?
O1X H1XB 0.8498 . ?
N3A C24A 1.334(5) . ?
N3A C24A 1.334(5) 2_556 ?
N4A C25A 1.334(5) 2_556 ?
N4A C25A 1.334(5) . ?
C24A C25A 1.389(7) . ?
C24A C28A 1.499(7) . ?
C25A C29A 1.489(6) . ?
C28A H28A 0.9600 . ?
C28A H28B 0.9600 . ?
C28A H28C 0.9600 . ?
C29A H29A 0.9600 . ?
C29A H29B 0.9600 . ?
C29A H29C 0.9600 . ?
N1A C22A 1.332(6) . ?
N1A C22A 1.332(6) 2_657 ?
N2A C23A 1.340(6) 2_657 ?
N2A C23A 1.340(6) . ?
O3X H3XA 0.8499 . ?
O3X H3XB 0.8501 . ?
C22A C23A 1.397(7) . ?
C22A C26A 1.487(7) . ?
C23A C27A 1.487(7) . ?
C26A H26A 0.9600 . ?
C26A H26B 0.9600 . ?
C26A H26C 0.9600 . ?
C27A H27A 0.9600 . ?
C27A H27B 0.9600 . ?
C27A H27C 0.9600 . ?
N1B C22B 1.330(5) . ?
N1B C25B 1.349(6) . ?
C22B C22B 1.394(8) 2_656 ?
C22B C26B 1.487(6) . ?
C25B C25B 1.381(9) 2_656 ?
C25B C29B 1.499(6) . ?
C26B H26D 0.9600 . ?
C26B H26E 0.9600 . ?
C26B H26F 0.9600 . ?
C29B H29D 0.9600 . ?
C29B H29E 0.9600 . ?
C29B H29F 0.9600 . ?
O2X H2XA 0.8496 . ?
O2X H2XB 0.8473 . ?
N2B C23B 1.344(6) . ?
N2B C24B 1.340(6) . ?
C23B C23B 1.388(9) 2_657 ?
C23B C27B 1.489(6) . ?
C24B C24B 1.372(9) 2_657 ?
C24B C28B 1.505(7) . ?
C27B H27D 0.9600 . ?
C27B H27E 0.9600 . ?
C27B H27F 0.9600 . ?
C28B H28D 0.9600 . ?
C28B H28E 0.9600 . ?
C28B H28F 0.9600 . ?
O4X H4XA 0.8502 . ?
O4X H4XB 0.8504 . ?

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
C2A C1A H1A 119.0 . . ?
C2A C1A C10A 121.9(4) . . ?
C10A C1A H1A 119.0 . . ?
C3A O1A H1AA 109.5 . . ?
C1A C2A H2A 119.9 . . ?
C3A C2A C1A 120.2(4) . . ?
C3A C2A H2A 119.9 . . ?
C17A O2A H2AA 113(4) . . ?
O1A C3A C2A 122.4(4) . . ?
O1A C3A C4A 118.7(4) . . ?
C2A C3A C4A 118.8(4) . . ?
C3A C4A H4A 119.4 . . ?
C5A C4A C3A 121.2(4) . . ?
C5A C4A H4A 119.4 . . ?
C4A C5A C6A 122.7(5) . . ?
C4A C5A C10A 120.6(4) . . ?
C10A C5A C6A 116.7(4) . . ?
C5A C6A H6AA 108.8 . . ?
C5A C6A H6AB 108.8 . . ?
H6AA C6A H6AB 107.7 . . ?
C7A C6A C5A 113.8(5) . . ?
C7A C6A H6AA 108.8 . . ?
C7A C6A H6AB 108.8 . . ?
C6A C7A H7AB 107.9 . . ?
C6A C7A H7AA 107.9 . . ?
C6A C7A C8A 117.5(4) . . ?
H7AB C7A H7AA 107.2 . . ?
C8A C7A H7AB 107.9 . . ?
C8A C7A H7AA 107.9 . . ?
C7A C8A H8A 108.1 . . ?
C7A C8A C9A 111.4(4) . . ?
C7A C8A C14A 113.2(4) . . ?
C9A C8A H8A 108.1 . . ?
C14A C8A H8A 108.1 . . ?
C14A C8A C9A 107.8(3) . . ?
C8A C9A H9A 105.7 . . ?
C10A C9A C8A 110.8(3) . . ?
C10A C9A H9A 105.7 . . ?
C10A C9A C11A 115.7(3) . . ?
C11A C9A C8A 112.4(4) . . ?
C11A C9A H9A 105.7 . . ?
C1A C10A C5A 117.2(4) . . ?
C1A C10A C9A 125.6(4) . . ?
C5A C10A C9A 117.2(4) . . ?
C9A C11A H11A 109.3 . . ?
C9A C11A H11B 109.3 . . ?
C9A C11A C12A 111.5(4) . . ?
H11A C11A H11B 108.0 . . ?
C12A C11A H11A 109.3 . . ?
C12A C11A H11B 109.3 . . ?
C11A C12A H12A 109.3 . . ?
C11A C12A H12B 109.3 . . ?
H12A C12A H12B 108.0 . . ?
C13A C12A C11A 111.5(4) . . ?
C13A C12A H12A 109.3 . . ?
C13A C12A H12B 109.3 . . ?
C12A C13A C14A 109.1(4) . . ?
C12A C13A C17A 116.8(3) . . ?
C12A C13A C18A 109.8(4) . . ?
C14A C13A C17A 100.2(3) . . ?
C14A C13A C18A 113.0(4) . . ?
C18A C13A C17A 107.8(4) . . ?
C8A C14A C13A 114.9(3) . . ?
C8A C14A H14A 106.0 . . ?
C8A C14A C15A 119.3(4) . . ?
C13A C14A H14A 106.0 . . ?
C13A C14A C15A 103.6(4) . . ?
C15A C14A H14A 106.0 . . ?
C14A C15A H15A 111.0 . . ?
C14A C15A H15B 111.0 . . ?
C14A C15A C16A 103.7(4) . . ?
H15A C15A H15B 109.0 . . ?
C16A C15A H15A 111.0 . . ?
C16A C15A H15B 111.0 . . ?
C15A C16A H16A 110.5 . . ?
C15A C16A H16B 110.5 . . ?
C15A C16A C17A 106.3(3) . . ?
H16A C16A H16B 108.7 . . ?
C17A C16A H16A 110.5 . . ?
C17A C16A H16B 110.5 . . ?
O2A C17A C13A 111.1(3) . . ?
O2A C17A C16A 113.5(4) . . ?
O2A C17A C20A 109.9(4) . . ?
C13A C17A C16A 102.5(3) . . ?
C20A C17A C13A 110.4(4) . . ?
C20A C17A C16A 109.2(4) . . ?
C13A C18A H18A 109.5 . . ?
C13A C18A H18B 109.5 . . ?
C13A C18A H18C 109.5 . . ?
H18A C18A H18B 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C21A C20A C17A 177.9(6) . . ?
C20A C21A H21A 180.0 . . ?
C2B C1B H1B 119.7 . . ?
C2B C1B C10B 120.6(5) . . ?
C10B C1B H1B 119.7 . . ?
C3B O1B H1BA 109.5 . . ?
C1B C2B H2B 119.8 . . ?
C3B C2B C1B 120.4(4) . . ?
C3B C2B H2B 119.8 . . ?
C17B O2B H2BA 111(3) . . ?
C2B C3B O1B 121.2(4) . . ?
C2B C3B C4B 119.1(5) . . ?
C4B C3B O1B 119.7(5) . . ?
C3B C4B H4B 119.4 . . ?
C3B C4B C5B 121.1(5) . . ?
C5B C4B H4B 119.4 . . ?
C4B C5B C6B 119.7(5) . . ?
C10B C5B C4B 120.3(4) . . ?
C10B C5B C6B 120.0(5) . . ?
C5B C6B H6BA 107.3 . . ?
C5B C6B H6BB 107.3 . . ?
H6BA C6B H6BB 106.9 . . ?
C7B C6B C5B 120.3(6) . . ?
C7B C6B H6BA 107.3 . . ?
C7B C6B H6BB 107.3 . . ?
C6B C7B H7BA 107.8 . . ?
C6B C7B H7BB 107.8 . . ?
C6B C7B C8B 118.1(6) . . ?
H7BA C7B H7BB 107.1 . . ?
C8B C7B H7BA 107.8 . . ?
C8B C7B H7BB 107.8 . . ?
C7B C8B H8B 108.8 . . ?
C7B C8B C9B 109.6(5) . . ?
C9B C8B H8B 108.8 . . ?
C14B C8B C7B 111.4(5) . . ?
C14B C8B H8B 108.8 . . ?
C14B C8B C9B 109.5(4) . . ?
C8B C9B H9B 105.7 . . ?
C8B C9B C11B 112.5(4) . . ?
C10B C9B C8B 111.1(4) . . ?
C10B C9B H9B 105.7 . . ?
C10B C9B C11B 115.3(4) . . ?
C11B C9B H9B 105.7 . . ?
C1B C10B C9B 123.1(5) . . ?
C5B C10B C1B 118.5(4) . . ?
C5B C10B C9B 118.4(4) . . ?
C9B C11B H11C 109.3 . . ?
C9B C11B H11D 109.3 . . ?
C9B C11B C12B 111.8(4) . . ?
H11C C11B H11D 107.9 . . ?
C12B C11B H11C 109.3 . . ?
C12B C11B H11D 109.3 . . ?
C11B C12B H12C 109.3 . . ?
C11B C12B H12D 109.3 . . ?
H12C C12B H12D 108.0 . . ?
C13B C12B C11B 111.6(4) . . ?
C13B C12B H12C 109.3 . . ?
C13B C12B H12D 109.3 . . ?
C12B C13B C14B 108.8(4) . . ?
C12B C13B C17B 117.3(4) . . ?
C12B C13B C18B 108.5(4) . . ?
C14B C13B C17B 100.5(4) . . ?
C14B C13B C18B 113.6(5) . . ?
C17B C13B C18B 108.0(4) . . ?
C8B C14B C13B 114.6(4) . . ?
C8B C14B H14B 106.1 . . ?
C8B C14B C15B 119.8(5) . . ?
C13B C14B H14B 106.1 . . ?
C13B C14B C15B 103.2(5) . . ?
C15B C14B H14B 106.1 . . ?
C14B C15B H15D 110.8 . . ?
C14B C15B H15C 110.8 . . ?
C14B C15B C16B 104.7(5) . . ?
H15D C15B H15C 108.9 . . ?
C16B C15B H15D 110.8 . . ?
C16B C15B H15C 110.8 . . ?
C15B C16B H16C 110.5 . . ?
C15B C16B H16D 110.5 . . ?
C15B C16B C17B 106.0(4) . . ?
H16C C16B H16D 108.7 . . ?
C17B C16B H16C 110.5 . . ?
C17B C16B H16D 110.5 . . ?
O2B C17B C13B 110.1(4) . . ?
O2B C17B C16B 113.3(4) . . ?
O2B C17B C20B 110.3(4) . . ?
C13B C17B C16B 102.7(4) . . ?
C20B C17B C13B 110.3(4) . . ?
C20B C17B C16B 110.0(4) . . ?
C13B C18B H18D 109.5 . . ?
C13B C18B H18E 109.5 . . ?
C13B C18B H18F 109.5 . . ?
H18D C18B H18E 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C21B C20B C17B 177.9(6) . . ?
C20B C21B H21B 180.0 . . ?
H1XA O1X H1XB 109.5 . . ?
C24A N3A C24A 118.2(6) . 2_556 ?
C25A N4A C25A 118.9(6) 2_556 . ?
N3A C24A C25A 121.0(5) . . ?
N3A C24A C28A 117.6(4) . . ?
C25A C24A C28A 121.4(4) . . ?
N4A C25A C24A 120.4(4) . . ?
N4A C25A C29A 117.2(4) . . ?
C24A C25A C29A 122.4(5) . . ?
C24A C28A H28A 109.5 . . ?
C24A C28A H28B 109.5 . . ?
C24A C28A H28C 109.5 . . ?
H28A C28A H28B 109.5 . . ?
H28A C28A H28C 109.5 . . ?
H28B C28A H28C 109.5 . . ?
C25A C29A H29A 109.5 . . ?
C25A C29A H29B 109.5 . . ?
C25A C29A H29C 109.5 . . ?
H29A C29A H29B 109.5 . . ?
H29A C29A H29C 109.5 . . ?
H29B C29A H29C 109.5 . . ?
C22A N1A C22A 118.7(6) 2_657 . ?
C23A N2A C23A 119.0(6) 2_657 . ?
H3XA O3X H3XB 109.5 . . ?
N1A C22A C23A 121.0(5) . . ?
N1A C22A C26A 117.8(5) . . ?
C23A C22A C26A 121.2(5) . . ?
N2A C23A C22A 120.1(5) . . ?
N2A C23A C27A 117.4(5) . . ?
C22A C23A C27A 122.4(5) . . ?
C22A C26A H26A 109.5 . . ?
C22A C26A H26B 109.5 . . ?
C22A C26A H26C 109.5 . . ?
H26A C26A H26B 109.5 . . ?
H26A C26A H26C 109.5 . . ?
H26B C26A H26C 109.5 . . ?
C23A C27A H27A 109.5 . . ?
C23A C27A H27B 109.5 . . ?
C23A C27A H27C 109.5 . . ?
H27A C27A H27B 109.5 . . ?
H27A C27A H27C 109.5 . . ?
H27B C27A H27C 109.5 . . ?
C22B N1B C25B 118.7(4) . . ?
N1B C22B C22B 120.7(2) . 2_656 ?
N1B C22B C26B 117.8(4) . . ?
C22B C22B C26B 121.5(3) 2_656 . ?
N1B C25B C25B 120.5(2) . 2_656 ?
N1B C25B C29B 118.0(4) . . ?
C25B C25B C29B 121.5(3) 2_656 . ?
C22B C26B H26D 109.5 . . ?
C22B C26B H26E 109.5 . . ?
C22B C26B H26F 109.5 . . ?
H26D C26B H26E 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?
C25B C29B H29D 109.5 . . ?
C25B C29B H29E 109.5 . . ?
C25B C29B H29F 109.5 . . ?
H29D C29B H29E 109.5 . . ?
H29D C29B H29F 109.5 . . ?
H29E C29B H29F 109.5 . . ?
H2XA O2X H2XB 105.0 . . ?
C24B N2B C23B 118.1(4) . . ?
N2B C23B C23B 120.7(2) . 2_657 ?
N2B C23B C27B 117.3(4) . . ?
C23B C23B C27B 122.0(3) 2_657 . ?
N2B C24B C24B 121.2(3) . 2_657 ?
N2B C24B C28B 116.6(4) . . ?
C24B C24B C28B 122.2(3) 2_657 . ?
C23B C27B H27D 109.5 . . ?
C23B C27B H27E 109.5 . . ?
C23B C27B H27F 109.5 . . ?
H27D C27B H27E 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 109.5 . . ?
C24B C28B H28D 109.5 . . ?
C24B C28B H28E 109.5 . . ?
C24B C28B H28F 109.5 . . ?
H28D C28B H28E 109.5 . . ?
H28D C28B H28F 109.5 . . ?
H28E C28B H28F 109.5 . . ?
H4XA O4X H4XB 104.5 . . ?

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
O2A H2AA N1B 0.89(6) 2.00(6) 2.892(5) 174(5) .
O2B H2BA N2B 0.83(5) 2.04(5) 2.868(5) 172(5) .
O1X H1XA O1B 0.85 2.04 2.713(6) 135.4 3_445
O1X H1XB N3A 0.85 2.15 2.868(8) 142.7 .
C29A H29C O2A 0.96 2.38 3.249(6) 151.1 .
O3X H3XA N2A 0.85 2.16 2.836(8) 136.4 .
O3X H3XB O1A 0.85 1.81 2.655(4) 175.1 .
C26A H26A O4X 0.96 2.50 3.349(9) 148.1 3_445
C26A H26C O2B 0.96 2.55 3.417(7) 149.9 3_445
C27A H27A O2B 0.96 2.51 3.379(6) 150.3 3_445
C29B H29E O2A 0.96 2.60 3.440(6) 145.7 .
O2X H2XA O1B 0.85 2.15 2.642(4) 116.4 2_656
O2X H2XB N4A 0.85 2.27 2.803(8) 120.8 .

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
C1A C2A C3A O1A -178.7(4) . . . . ?
C1A C2A C3A C4A 0.1(7) . . . . ?
O1A C3A C4A C5A 178.5(5) . . . . ?
C2A C1A C10A C5A 0.4(7) . . . . ?
C2A C1A C10A C9A 179.1(4) . . . . ?
C2A C3A C4A C5A -0.3(7) . . . . ?
C3A C4A C5A C6A -178.7(6) . . . . ?
C3A C4A C5A C10A 0.6(8) . . . . ?
C4A C5A C6A C7A -138.0(6) . . . . ?
C4A C5A C10A C1A -0.6(7) . . . . ?
C4A C5A C10A C9A -179.5(4) . . . . ?
C5A C6A C7A C8A -36.9(9) . . . . ?
C6A C5A C10A C1A 178.8(6) . . . . ?
C6A C5A C10A C9A -0.1(7) . . . . ?
C6A C7A C8A C9A -8.5(7) . . . . ?
C6A C7A C8A C14A -130.2(6) . . . . ?
C7A C8A C9A C10A 49.1(5) . . . . ?
C7A C8A C9A C11A -179.8(4) . . . . ?
C7A C8A C14A C13A 180.0(4) . . . . ?
C7A C8A C14A C15A -56.1(6) . . . . ?
C8A C9A C10A C1A 135.3(5) . . . . ?
C8A C9A C10A C5A -45.9(6) . . . . ?
C8A C9A C11A C12A 56.4(5) . . . . ?
C8A C14A C15A C16A -163.6(4) . . . . ?
C9A C8A C14A C13A 56.3(5) . . . . ?
C9A C8A C14A C15A -179.8(4) . . . . ?
C9A C11A C12A C13A -55.4(6) . . . . ?
C10A C1A C2A C3A -0.1(8) . . . . ?
C10A C5A C6A C7A 42.6(9) . . . . ?
C10A C9A C11A C12A -175.0(4) . . . . ?
C11A C9A C10A C1A 5.9(7) . . . . ?
C11A C9A C10A C5A -175.4(4) . . . . ?
C11A C12A C13A C14A 53.9(5) . . . . ?
C11A C12A C13A C17A 166.6(4) . . . . ?
C11A C12A C13A C18A -70.4(5) . . . . ?
C12A C13A C14A C8A -56.6(5) . . . . ?
C12A C13A C14A C15A 171.6(4) . . . . ?
C12A C13A C17A O2A 77.9(5) . . . . ?
C12A C13A C17A C16A -160.5(4) . . . . ?
C12A C13A C17A C20A -44.3(5) . . . . ?
C13A C14A C15A C16A -34.4(5) . . . . ?
C14A C8A C9A C10A 173.9(4) . . . . ?
C14A C8A C9A C11A -55.0(5) . . . . ?
C14A C13A C17A O2A -164.4(3) . . . . ?
C14A C13A C17A C16A -42.9(4) . . . . ?
C14A C13A C17A C20A 73.3(4) . . . . ?
C14A C15A C16A C17A 6.9(6) . . . . ?
C15A C16A C17A O2A 142.2(4) . . . . ?
C15A C16A C17A C13A 22.3(5) . . . . ?
C15A C16A C17A C20A -94.8(5) . . . . ?
C17A C13A C14A C8A -179.7(4) . . . . ?
C17A C13A C14A C15A 48.4(4) . . . . ?
C18A C13A C14A C8A 65.9(5) . . . . ?
C18A C13A C14A C15A -66.0(5) . . . . ?
C18A C13A C17A O2A -46.1(5) . . . . ?
C18A C13A C17A C16A 75.5(4) . . . . ?
C18A C13A C17A C20A -168.3(4) . . . . ?
C1B C2B C3B O1B -179.0(4) . . . . ?
C1B C2B C3B C4B 0.6(8) . . . . ?
O1B C3B C4B C5B -178.9(5) . . . . ?
C2B C1B C10B C5B 0.1(7) . . . . ?
C2B C1B C10B C9B -179.3(4) . . . . ?
C2B C3B C4B C5B 1.5(8) . . . . ?
C3B C4B C5B C6B 175.5(7) . . . . ?
C3B C4B C5B C10B -2.8(8) . . . . ?
C4B C5B C6B C7B -164.7(8) . . . . ?
C4B C5B C10B C1B 2.0(8) . . . . ?
C4B C5B C10B C9B -178.6(5) . . . . ?
C5B C6B C7B C8B 6.7(14) . . . . ?
C6B C5B C10B C1B -176.3(6) . . . . ?
C6B C5B C10B C9B 3.1(8) . . . . ?
C6B C7B C8B C9B -40.3(10) . . . . ?
C6B C7B C8B C14B -161.5(8) . . . . ?
C7B C8B C9B C10B 54.0(6) . . . . ?
C7B C8B C9B C11B -175.1(5) . . . . ?
C7B C8B C14B C13B 177.3(5) . . . . ?
C7B C8B C14B C15B -59.3(8) . . . . ?
C8B C9B C10B C1B 142.0(5) . . . . ?
C8B C9B C10B C5B -37.3(6) . . . . ?
C8B C9B C11B C12B 53.1(5) . . . . ?
C8B C14B C15B C16B -160.0(5) . . . . ?
C9B C8B C14B C13B 56.0(6) . . . . ?
C9B C8B C14B C15B 179.3(5) . . . . ?
C9B C11B C12B C13B -54.5(5) . . . . ?
C10B C1B C2B C3B -1.4(7) . . . . ?
C10B C5B C6B C7B 13.5(13) . . . . ?
C10B C9B C11B C12B -178.2(4) . . . . ?
C11B C9B C10B C1B 12.6(6) . . . . ?
C11B C9B C10B C5B -166.7(4) . . . . ?
C11B C12B C13B C14B 54.9(5) . . . . ?
C11B C12B C13B C17B 168.1(4) . . . . ?
C11B C12B C13B C18B -69.2(5) . . . . ?
C12B C13B C14B C8B -57.5(6) . . . . ?
C12B C13B C14B C15B 170.6(5) . . . . ?
C12B C13B C17B O2B 77.4(5) . . . . ?
C12B C13B C17B C16B -161.7(5) . . . . ?
C12B C13B C17B C20B -44.5(6) . . . . ?
C13B C14B C15B C16B -31.3(7) . . . . ?
C14B C8B C9B C10B 176.5(4) . . . . ?
C14B C8B C9B C11B -52.6(6) . . . . ?
C14B C13B C17B O2B -164.8(4) . . . . ?
C14B C13B C17B C16B -43.9(5) . . . . ?
C14B C13B C17B C20B 73.2(5) . . . . ?
C14B C15B C16B C17B 3.7(7) . . . . ?
C15B C16B C17B O2B 143.7(5) . . . . ?
C15B C16B C17B C13B 25.0(6) . . . . ?
C15B C16B C17B C20B -92.4(6) . . . . ?
C17B C13B C14B C8B 178.7(4) . . . . ?
C17B C13B C14B C15B 46.8(5) . . . . ?
C18B C13B C14B C8B 63.5(6) . . . . ?
C18B C13B C14B C15B -68.4(6) . . . . ?
C18B C13B C17B O2B -45.5(6) . . . . ?
C18B C13B C17B C16B 75.4(5) . . . . ?
C18B C13B C17B C20B -167.5(5) . . . . ?
N3A C24A C25A N4A -2.8(7) . . . . ?
N3A C24A C25A C29A 178.5(4) . . . . ?
C24A N3A C24A C25A 1.3(3) 2_556 . . . ?
C24A N3A C24A C28A -178.1(5) 2_556 . . . ?
C25A N4A C25A C24A 1.3(3) 2_556 . . . ?
C25A N4A C25A C29A -179.8(4) 2_556 . . . ?
C28A C24A C25A N4A 176.6(4) . . . . ?
C28A C24A C25A C29A -2.1(7) . . . . ?
N1A C22A C23A N2A -0.2(7) . . . . ?
N1A C22A C23A C27A -179.3(4) . . . . ?
C22A N1A C22A C23A 0.1(3) 2_657 . . . ?
C22A N1A C22A C26A -179.1(5) 2_657 . . . ?
C23A N2A C23A C22A 0.1(3) 2_657 . . . ?
C23A N2A C23A C27A 179.2(5) 2_657 . . . ?
C26A C22A C23A N2A 178.9(4) . . . . ?
C26A C22A C23A C27A -0.1(8) . . . . ?
C22B N1B C25B C25B -2.1(7) . . . 2_656 ?
C22B N1B C25B C29B 179.2(4) . . . . ?
C25B N1B C22B C22B 0.8(8) . . . 2_656 ?
C25B N1B C22B C26B -178.4(4) . . . . ?
C23B N2B C24B C24B -0.6(8) . . . 2_657 ?
C23B N2B C24B C28B 178.9(4) . . . . ?
C24B N2B C23B C23B 1.4(8) . . . 2_657 ?
C24B N2B C23B C27B -178.3(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 2.062
_oxdiff_exptl_absorpt_empirical_full_min 0.580
