# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_22019605_0m
_database_code_depnum_ccdc_archive 'CCDC 1945280'
loop_
_audit_author_name
_audit_author_address
'Jianqing Yu'
;Wuhan University
China
;
_audit_update_record             
;
2019-08-05 deposited with the CCDC.	2019-11-29 downloaded from the CCDC.
;
_audit_creation_date             2019-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H27 N O3'
_chemical_formula_sum            'C20 H27 N O3'
_chemical_formula_weight         329.42
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.9662(3)
_cell_length_b                   11.7770(3)
_cell_length_c                   27.0642(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3495.31(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.353
_cell_measurement_theta_min      4.095
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.907
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1174 before and 0.0469 after correction. The Ratio of minimum to maximum transmission is 0.8336. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            21237
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.358
_diffrn_reflns_theta_min         4.094
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                6628
_reflns_number_total             7061
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.214
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 2751 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         7061
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.050
_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)+(0.0388P)²+0.5172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0823
_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:
 C5(H5), C7A(H7A), C8(H8), C5A(H5A), C7(H7), C20A(H20A), C8A(H8A), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C13A(H13C,H13D), C6A(H6AA,H6AB), C19A(H19C,H19D), C9(H9A,H9B),
 C9A(H9AA,H9AB), C1A(H1AA,H1AB), C2(H2A,H2B), C13(H13A,H13B), C2A(H2AA,H2AB),
 C19(H19A,H19B), C1(H1A,H1B), C18A(H18C,H18D), C18(H18A,H18B), C3A(H3AA,H3AB),
 C3(H3A,H3B), C17A(H17C,H17D), C17(H17A,H17B)
2.c X=CH2 refined with riding coordinates:
 C15(H15A,H15B), C15A(H15C,H15D)
2.d Idealised Me refined as rotating group:
 C14A(H14D,H14E,H14F), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.51400(12) 0.43600(11) 0.55043(5) 0.0188(3) Uani 1 1 d . . . . .
O6 O 0.33501(11) 0.81468(11) 0.55458(5) 0.0181(3) Uani 1 1 d . . . . .
O4 O 0.36968(11) 0.65907(11) 0.50934(5) 0.0205(3) Uani 1 1 d . . . . .
O2 O 0.65435(12) 0.35877(12) 0.50105(6) 0.0241(3) Uani 1 1 d . . . . .
O5 O 0.12043(16) 0.52398(14) 0.42073(6) 0.0325(4) Uani 1 1 d . . . . .
O3 O 0.55245(19) 0.07778(15) 0.41343(6) 0.0409(4) Uani 1 1 d . . . . .
N2 N 0.14414(15) 0.71686(15) 0.42532(6) 0.0216(3) Uani 1 1 d . . . . .
N1 N 0.42006(19) 0.22715(16) 0.42246(7) 0.0290(4) Uani 1 1 d . . . . .
C6 C 0.42721(17) 0.21784(15) 0.59785(7) 0.0175(4) Uani 1 1 d . . . . .
H6A H 0.412479 0.135802 0.592574 0.021 Uiso 1 1 calc R . . . .
H6B H 0.516437 0.230132 0.599384 0.021 Uiso 1 1 calc R . . . .
C12A C 0.29977(16) 0.73016(16) 0.52394(7) 0.0151(3) Uani 1 1 d . . . . .
C5 C 0.36935(17) 0.25455(15) 0.64658(7) 0.0176(4) Uani 1 1 d . . . . .
H5 H 0.279118 0.247690 0.642167 0.021 Uiso 1 1 calc R . . . .
C12 C 0.55254(17) 0.35696(15) 0.51802(7) 0.0177(4) Uani 1 1 d . . . . .
C13A C 0.10667(16) 0.62752(15) 0.49951(7) 0.0170(4) Uani 1 1 d . . . . .
H13C H 0.147649 0.565525 0.517795 0.020 Uiso 1 1 calc R . . . .
H13D H 0.018978 0.627640 0.508198 0.020 Uiso 1 1 calc R . . . .
C7A C 0.12037(15) 0.80789(15) 0.55685(7) 0.0148(3) Uani 1 1 d . . . . .
H7A H 0.045319 0.852544 0.548933 0.018 Uiso 1 1 calc R . . . .
C11A C 0.16517(15) 0.74244(14) 0.51156(6) 0.0142(3) Uani 1 1 d . . . . .
C4 C 0.40229(19) 0.18246(16) 0.69110(7) 0.0209(4) Uani 1 1 d . . . . .
C8 C 0.38491(16) 0.41294(15) 0.56324(7) 0.0166(3) Uani 1 1 d . . . . .
H8 H 0.331643 0.453100 0.538863 0.020 Uiso 1 1 calc R . . . .
C6A C 0.09807(16) 0.72772(16) 0.60076(7) 0.0164(3) Uani 1 1 d . . . . .
H6AA H 0.021397 0.685137 0.595317 0.020 Uiso 1 1 calc R . . . .
H6AB H 0.165588 0.672128 0.602847 0.020 Uiso 1 1 calc R . . . .
C19A C 0.25983(17) 0.87886(17) 0.44041(7) 0.0209(4) Uani 1 1 d . . . . .
H19C H 0.340021 0.847024 0.449917 0.025 Uiso 1 1 calc R . . . .
H19D H 0.255009 0.958861 0.451473 0.025 Uiso 1 1 calc R . . . .
C5A C 0.08942(17) 0.79324(16) 0.64938(7) 0.0173(4) Uani 1 1 d . . . . .
H5A H 0.025757 0.853006 0.644538 0.021 Uiso 1 1 calc R . . . .
C10A C 0.21057(17) 0.85651(16) 0.66132(7) 0.0177(4) Uani 1 1 d . . . . .
C7 C 0.37383(17) 0.28538(16) 0.55449(7) 0.0166(4) Uani 1 1 d . . . . .
H7 H 0.287069 0.263408 0.548340 0.020 Uiso 1 1 calc R . . . .
C10 C 0.39563(18) 0.38165(16) 0.65841(7) 0.0189(4) Uani 1 1 d . . . . .
C20A C 0.15507(16) 0.80826(16) 0.46157(7) 0.0165(3) Uani 1 1 d . . . . .
H20A H 0.078662 0.854607 0.461488 0.020 Uiso 1 1 calc R . . . .
C9 C 0.35361(19) 0.45523(16) 0.61453(7) 0.0204(4) Uani 1 1 d . . . . .
H9A H 0.263929 0.463632 0.616596 0.025 Uiso 1 1 calc R . . . .
H9B H 0.389432 0.531841 0.618521 0.025 Uiso 1 1 calc R . . . .
C8A C 0.22905(17) 0.88667(16) 0.56635(7) 0.0176(4) Uani 1 1 d . . . . .
H8A H 0.225870 0.950396 0.541971 0.021 Uiso 1 1 calc R . . . .
C16 C 0.4956(2) 0.14519(18) 0.43911(8) 0.0264(4) Uani 1 1 d . . . . .
C9A C 0.23991(18) 0.93678(16) 0.61783(7) 0.0202(4) Uani 1 1 d . . . . .
H9AA H 0.184737 1.003138 0.619945 0.024 Uiso 1 1 calc R . . . .
H9AB H 0.324245 0.965126 0.622116 0.024 Uiso 1 1 calc R . . . .
C4A C 0.04953(18) 0.72291(19) 0.69349(7) 0.0223(4) Uani 1 1 d . . . . .
C1A C 0.1906(2) 0.92942(18) 0.70807(7) 0.0233(4) Uani 1 1 d . . . . .
H1AA H 0.267945 0.968113 0.716621 0.028 Uiso 1 1 calc R . . . .
H1AB H 0.129097 0.988644 0.700834 0.028 Uiso 1 1 calc R . . . .
C2 C 0.3449(2) 0.34098(18) 0.74916(7) 0.0264(4) Uani 1 1 d . . . . .
H2A H 0.287495 0.361258 0.775971 0.032 Uiso 1 1 calc R . . . .
H2B H 0.428760 0.355897 0.761052 0.032 Uiso 1 1 calc R . . . .
C20 C 0.38172(17) 0.31022(16) 0.45933(7) 0.0184(4) Uani 1 1 d . . . . .
H20 H 0.291799 0.303486 0.464713 0.022 Uiso 1 1 calc R . . . .
C16A C 0.12386(17) 0.61316(18) 0.44408(7) 0.0219(4) Uani 1 1 d . . . . .
C11 C 0.45040(16) 0.27244(15) 0.50735(7) 0.0171(4) Uani 1 1 d . . . . .
C13 C 0.49770(18) 0.15286(16) 0.49490(8) 0.0216(4) Uani 1 1 d . . . . .
H13A H 0.581642 0.142338 0.507558 0.026 Uiso 1 1 calc R . . . .
H13B H 0.444415 0.094107 0.509678 0.026 Uiso 1 1 calc R . . . .
C15 C 0.4867(2) 0.10187(18) 0.69086(8) 0.0271(4) Uani 1 1 d . . . . .
H15A H 0.504719 0.061412 0.720338 0.033 Uiso 1 1 calc R . . . .
H15B H 0.529218 0.084589 0.661210 0.033 Uiso 1 1 calc R . . . .
C2A C 0.1481(2) 0.85978(18) 0.75232(7) 0.0250(4) Uani 1 1 d . . . . .
H2AA H 0.131914 0.911036 0.780565 0.030 Uiso 1 1 calc R . . . .
H2AB H 0.213311 0.806238 0.762177 0.030 Uiso 1 1 calc R . . . .
C19 C 0.4093(2) 0.42254(18) 0.43309(8) 0.0251(4) Uani 1 1 d . . . . .
H19A H 0.496500 0.443094 0.436010 0.030 Uiso 1 1 calc R . . . .
H19B H 0.358737 0.485161 0.446371 0.030 Uiso 1 1 calc R . . . .
C14A C 0.31723(17) 0.77430(18) 0.66993(8) 0.0213(4) Uani 1 1 d . . . . .
H14D H 0.294113 0.718119 0.694946 0.032 Uiso 1 1 calc GR . . . .
H14E H 0.388583 0.816902 0.681402 0.032 Uiso 1 1 calc GR . . . .
H14F H 0.337036 0.735433 0.638936 0.032 Uiso 1 1 calc GR . . . .
C15A C 0.0360(2) 0.6111(2) 0.69315(8) 0.0283(5) Uani 1 1 d . . . . .
H15C H 0.014427 0.572354 0.722668 0.034 Uiso 1 1 calc R . . . .
H15D H 0.047768 0.569790 0.663400 0.034 Uiso 1 1 calc R . . . .
C1 C 0.3191(2) 0.41453(17) 0.70396(7) 0.0242(4) Uani 1 1 d . . . . .
H1A H 0.335713 0.494848 0.712382 0.029 Uiso 1 1 calc R . . . .
H1B H 0.231507 0.408196 0.695465 0.029 Uiso 1 1 calc R . . . .
C14 C 0.5318(2) 0.40114(18) 0.66912(8) 0.0252(4) Uani 1 1 d . . . . .
H14A H 0.559014 0.348027 0.694720 0.038 Uiso 1 1 calc GR . . . .
H14B H 0.544129 0.479239 0.680576 0.038 Uiso 1 1 calc GR . . . .
H14C H 0.579071 0.388571 0.638870 0.038 Uiso 1 1 calc GR . . . .
C18A C 0.23811(19) 0.8687(2) 0.38451(8) 0.0270(4) Uani 1 1 d . . . . .
H18C H 0.314422 0.882633 0.365938 0.032 Uiso 1 1 calc R . . . .
H18D H 0.175447 0.923506 0.373390 0.032 Uiso 1 1 calc R . . . .
C18 C 0.3749(2) 0.3948(2) 0.37940(8) 0.0302(5) Uani 1 1 d . . . . .
H18A H 0.285732 0.400953 0.374344 0.036 Uiso 1 1 calc R . . . .
H18B H 0.416745 0.446629 0.356111 0.036 Uiso 1 1 calc R . . . .
C3A C 0.0319(2) 0.7931(2) 0.73981(8) 0.0280(4) Uani 1 1 d . . . . .
H3AA H 0.010798 0.742481 0.767743 0.034 Uiso 1 1 calc R . . . .
H3AB H -0.036609 0.846691 0.734876 0.034 Uiso 1 1 calc R . . . .
C3 C 0.3314(2) 0.21424(18) 0.73681(7) 0.0253(4) Uani 1 1 d . . . . .
H3A H 0.360845 0.168409 0.765056 0.030 Uiso 1 1 calc R . . . .
H3B H 0.244118 0.196374 0.731656 0.030 Uiso 1 1 calc R . . . .
C17A C 0.1941(2) 0.7459(2) 0.37711(8) 0.0307(5) Uani 1 1 d . . . . .
H17C H 0.130750 0.741558 0.351099 0.037 Uiso 1 1 calc R . . . .
H17D H 0.262542 0.695103 0.368201 0.037 Uiso 1 1 calc R . . . .
C17 C 0.4180(3) 0.2728(2) 0.37233(9) 0.0458(7) Uani 1 1 d . . . . .
H17A H 0.360698 0.229669 0.351168 0.055 Uiso 1 1 calc R . . . .
H17B H 0.500210 0.270507 0.357254 0.055 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.347(2) . ?
O1 C8 1.483(2) . ?
O6 C12A 1.352(2) . ?
O6 C8A 1.473(2) . ?
O4 C12A 1.202(2) . ?
O2 C12 1.207(2) . ?
O5 C16A 1.226(3) . ?
O3 C16 1.226(3) . ?
N2 C20A 1.461(2) . ?
N2 C16A 1.341(3) . ?
N2 C17A 1.456(3) . ?
N1 C16 1.349(3) . ?
N1 C20 1.459(3) . ?
N1 C17 1.459(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.526(3) . ?
C6 C7 1.534(3) . ?
C12A C11A 1.520(2) . ?
C5 H5 1.0000 . ?
C5 C4 1.517(3) . ?
C5 C10 1.558(3) . ?
C12 C11 1.526(3) . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C13A C11A 1.533(2) . ?
C13A C16A 1.521(3) . ?
C7A H7A 1.0000 . ?
C7A C11A 1.529(2) . ?
C7A C6A 1.537(2) . ?
C7A C8A 1.532(2) . ?
C11A C20A 1.563(2) . ?
C4 C15 1.326(3) . ?
C4 C3 1.508(3) . ?
C8 H8 1.0000 . ?
C8 C7 1.526(2) . ?
C8 C9 1.514(3) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C6A C5A 1.528(3) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C19A C20A 1.529(3) . ?
C19A C18A 1.536(3) . ?
C5A H5A 1.0000 . ?
C5A C10A 1.557(3) . ?
C5A C4A 1.518(3) . ?
C10A C9A 1.544(3) . ?
C10A C1A 1.545(3) . ?
C10A C14A 1.536(3) . ?
C7 H7 1.0000 . ?
C7 C11 1.535(3) . ?
C10 C9 1.541(3) . ?
C10 C1 1.541(3) . ?
C10 C14 1.539(3) . ?
C20A H20A 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C8A H8A 1.0000 . ?
C8A C9A 1.518(3) . ?
C16 C13 1.513(3) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C4A C15A 1.325(3) . ?
C4A C3A 1.514(3) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C1A C2A 1.525(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.525(3) . ?
C2 C3 1.537(3) . ?
C20 H20 1.0000 . ?
C20 C11 1.567(3) . ?
C20 C19 1.531(3) . ?
C11 C13 1.538(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 H15A 0.9500 . ?
C15 H15B 0.9500 . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.535(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C18 1.536(3) . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
C15A H15C 0.9500 . ?
C15A H15D 0.9500 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C18A C17A 1.537(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C17 1.525(3) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?

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
C12 O1 C8 108.99(14) . . ?
C12A O6 C8A 109.32(14) . . ?
C16A N2 C20A 115.49(16) . . ?
C16A N2 C17A 127.99(18) . . ?
C17A N2 C20A 113.44(17) . . ?
C16 N1 C20 115.34(17) . . ?
C16 N1 C17 125.7(2) . . ?
C20 N1 C17 112.61(18) . . ?
H6A C6 H6B 108.1 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 C7 110.84(15) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
O6 C12A C11A 110.04(15) . . ?
O4 C12A O6 122.15(16) . . ?
O4 C12A C11A 127.81(17) . . ?
C6 C5 H5 106.6 . . ?
C6 C5 C10 111.89(15) . . ?
C4 C5 C6 115.38(16) . . ?
C4 C5 H5 106.6 . . ?
C4 C5 C10 109.30(15) . . ?
C10 C5 H5 106.6 . . ?
O1 C12 C11 110.10(15) . . ?
O2 C12 O1 121.71(17) . . ?
O2 C12 C11 128.19(17) . . ?
H13C C13A H13D 108.9 . . ?
C11A C13A H13C 110.8 . . ?
C11A C13A H13D 110.8 . . ?
C16A C13A H13C 110.8 . . ?
C16A C13A H13D 110.8 . . ?
C16A C13A C11A 104.84(15) . . ?
C11A C7A H7A 111.0 . . ?
C11A C7A C6A 111.18(14) . . ?
C11A C7A C8A 100.95(14) . . ?
C6A C7A H7A 111.0 . . ?
C8A C7A H7A 111.0 . . ?
C8A C7A C6A 111.47(15) . . ?
C12A C11A C13A 111.67(14) . . ?
C12A C11A C7A 100.55(14) . . ?
C12A C11A C20A 107.86(14) . . ?
C13A C11A C20A 102.95(14) . . ?
C7A C11A C13A 118.76(15) . . ?
C7A C11A C20A 114.90(14) . . ?
C15 C4 C5 124.25(19) . . ?
C15 C4 C3 122.79(19) . . ?
C3 C4 C5 112.94(17) . . ?
O1 C8 H8 108.5 . . ?
O1 C8 C7 102.71(14) . . ?
O1 C8 C9 111.75(15) . . ?
C7 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
C9 C8 C7 116.62(16) . . ?
C7A C6A H6AA 109.3 . . ?
C7A C6A H6AB 109.3 . . ?
H6AA C6A H6AB 108.0 . . ?
C5A C6A C7A 111.43(15) . . ?
C5A C6A H6AA 109.3 . . ?
C5A C6A H6AB 109.3 . . ?
H19C C19A H19D 109.2 . . ?
C20A C19A H19C 111.3 . . ?
C20A C19A H19D 111.3 . . ?
C20A C19A C18A 102.10(16) . . ?
C18A C19A H19C 111.3 . . ?
C18A C19A H19D 111.3 . . ?
C6A C5A H5A 106.6 . . ?
C6A C5A C10A 111.56(15) . . ?
C10A C5A H5A 106.6 . . ?
C4A C5A C6A 114.82(16) . . ?
C4A C5A H5A 106.6 . . ?
C4A C5A C10A 110.11(15) . . ?
C9A C10A C5A 108.22(15) . . ?
C9A C10A C1A 108.28(15) . . ?
C1A C10A C5A 108.38(15) . . ?
C14A C10A C5A 112.30(16) . . ?
C14A C10A C9A 110.05(16) . . ?
C14A C10A C1A 109.51(16) . . ?
C6 C7 H7 110.9 . . ?
C6 C7 C11 112.07(15) . . ?
C8 C7 C6 111.20(15) . . ?
C8 C7 H7 110.9 . . ?
C8 C7 C11 100.56(14) . . ?
C11 C7 H7 110.9 . . ?
C9 C10 C5 109.08(15) . . ?
C9 C10 C1 108.20(16) . . ?
C1 C10 C5 107.76(16) . . ?
C14 C10 C5 111.20(16) . . ?
C14 C10 C9 110.59(16) . . ?
C14 C10 C1 109.92(16) . . ?
N2 C20A C11A 102.79(14) . . ?
N2 C20A C19A 102.17(15) . . ?
N2 C20A H20A 109.4 . . ?
C11A C20A H20A 109.4 . . ?
C19A C20A C11A 122.71(15) . . ?
C19A C20A H20A 109.4 . . ?
C8 C9 C10 116.99(15) . . ?
C8 C9 H9A 108.0 . . ?
C8 C9 H9B 108.0 . . ?
C10 C9 H9A 108.0 . . ?
C10 C9 H9B 108.0 . . ?
H9A C9 H9B 107.3 . . ?
O6 C8A C7A 103.22(14) . . ?
O6 C8A H8A 108.5 . . ?
O6 C8A C9A 111.12(15) . . ?
C7A C8A H8A 108.5 . . ?
C9A C8A C7A 116.79(16) . . ?
C9A C8A H8A 108.5 . . ?
O3 C16 N1 125.9(2) . . ?
O3 C16 C13 126.6(2) . . ?
N1 C16 C13 107.47(17) . . ?
C10A C9A H9AA 108.2 . . ?
C10A C9A H9AB 108.2 . . ?
C8A C9A C10A 116.45(15) . . ?
C8A C9A H9AA 108.2 . . ?
C8A C9A H9AB 108.2 . . ?
H9AA C9A H9AB 107.3 . . ?
C15A C4A C5A 124.7(2) . . ?
C15A C4A C3A 122.3(2) . . ?
C3A C4A C5A 112.98(18) . . ?
C10A C1A H1AA 109.0 . . ?
C10A C1A H1AB 109.0 . . ?
H1AA C1A H1AB 107.8 . . ?
C2A C1A C10A 112.81(16) . . ?
C2A C1A H1AA 109.0 . . ?
C2A C1A H1AB 109.0 . . ?
H2A C2 H2B 108.0 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C1 C2 C3 111.05(17) . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
N1 C20 H20 109.3 . . ?
N1 C20 C11 103.79(15) . . ?
N1 C20 C19 101.84(16) . . ?
C11 C20 H20 109.3 . . ?
C19 C20 H20 109.3 . . ?
C19 C20 C11 122.37(16) . . ?
O5 C16A N2 126.15(19) . . ?
O5 C16A C13A 126.84(19) . . ?
N2 C16A C13A 107.01(16) . . ?
C12 C11 C7 100.34(14) . . ?
C12 C11 C20 108.93(15) . . ?
C12 C11 C13 113.02(15) . . ?
C7 C11 C20 113.48(14) . . ?
C7 C11 C13 117.23(15) . . ?
C13 C11 C20 103.91(15) . . ?
C16 C13 C11 105.55(16) . . ?
C16 C13 H13A 110.6 . . ?
C16 C13 H13B 110.6 . . ?
C11 C13 H13A 110.6 . . ?
C11 C13 H13B 110.6 . . ?
H13A C13 H13B 108.8 . . ?
C4 C15 H15A 120.0 . . ?
C4 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C1A C2A H2AA 109.5 . . ?
C1A C2A H2AB 109.5 . . ?
C1A C2A C3A 110.85(17) . . ?
H2AA C2A H2AB 108.1 . . ?
C3A C2A H2AA 109.5 . . ?
C3A C2A H2AB 109.5 . . ?
C20 C19 H19A 111.4 . . ?
C20 C19 H19B 111.4 . . ?
C20 C19 C18 101.93(17) . . ?
H19A C19 H19B 109.2 . . ?
C18 C19 H19A 111.4 . . ?
C18 C19 H19B 111.4 . . ?
C10A C14A H14D 109.5 . . ?
C10A C14A H14E 109.5 . . ?
C10A C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
C4A C15A H15C 120.0 . . ?
C4A C15A H15D 120.0 . . ?
H15C C15A H15D 120.0 . . ?
C10 C1 H1A 108.9 . . ?
C10 C1 H1B 108.9 . . ?
C2 C1 C10 113.42(17) . . ?
C2 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C19A C18A H18C 110.8 . . ?
C19A C18A H18D 110.8 . . ?
C19A C18A C17A 104.51(17) . . ?
H18C C18A H18D 108.9 . . ?
C17A C18A H18C 110.8 . . ?
C17A C18A H18D 110.8 . . ?
C19 C18 H18A 110.9 . . ?
C19 C18 H18B 110.9 . . ?
H18A C18 H18B 109.0 . . ?
C17 C18 C19 104.06(18) . . ?
C17 C18 H18A 110.9 . . ?
C17 C18 H18B 110.9 . . ?
C4A C3A C2A 110.84(17) . . ?
C4A C3A H3AA 109.5 . . ?
C4A C3A H3AB 109.5 . . ?
C2A C3A H3AA 109.5 . . ?
C2A C3A H3AB 109.5 . . ?
H3AA C3A H3AB 108.1 . . ?
C4 C3 C2 111.71(17) . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
N2 C17A C18A 102.85(17) . . ?
N2 C17A H17C 111.2 . . ?
N2 C17A H17D 111.2 . . ?
C18A C17A H17C 111.2 . . ?
C18A C17A H17D 111.2 . . ?
H17C C17A H17D 109.1 . . ?
N1 C17 C18 103.59(18) . . ?
N1 C17 H17A 111.0 . . ?
N1 C17 H17B 111.0 . . ?
C18 C17 H17A 111.0 . . ?
C18 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_190528_zxq_4_0m
_database_code_depnum_ccdc_archive 'CCDC 1945284'
loop_
_audit_author_name
_audit_author_address
'Jianqing Yu'
;Wuhan University
China
;
_audit_update_record             
;
2019-08-05 deposited with the CCDC.	2019-11-29 downloaded from the CCDC.
;
_audit_creation_date             2019-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H31 N O4'
_chemical_formula_sum            'C21 H31 N O4'
_chemical_formula_weight         361.47
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.7456(10)
_cell_length_b                   11.2402(9)
_cell_length_c                   22.236(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1935.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9865
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      3.98
_shelx_estimated_absorpt_T_max   0.782
_shelx_estimated_absorpt_T_min   0.731
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0923 before and 0.0414 after correction.
The Ratio of minimum to maximum transmission is 0.8591.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.38
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13106
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.352
_diffrn_reflns_theta_min         3.976
_diffrn_ambient_temperature      169.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3534
_reflns_number_total             3543
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.162
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 1482 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3543
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.096
_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)+(0.0507P)²+0.2569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0823
_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:
 C5(H5), C8(H8), C9(H9), C11(H11), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C10(H10A,H10B), C15(H15A,
 H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.c X=CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.02518(15) 0.44635(11) 0.36844(5) 0.0260(3) Uani 1 1 d . . . . .
O2 O 0.0992(2) 0.27709(13) 0.41383(6) 0.0428(4) Uani 1 1 d . . . . .
O3 O 0.4369(2) 0.71427(12) 0.53512(7) 0.0455(4) Uani 1 1 d . . . . .
O4 O 0.24747(17) 0.60358(12) 0.58576(6) 0.0331(3) Uani 1 1 d . . . . .
N1 N 0.53551(17) 0.47981(12) 0.48595(6) 0.0204(3) Uani 1 1 d . . . . .
C1 C 0.1614(3) 0.70509(18) 0.21406(9) 0.0338(4) Uani 1 1 d . . . . .
H1A H 0.047370 0.694098 0.194753 0.041 Uiso 1 1 calc R . . . .
H1B H 0.163128 0.785287 0.232460 0.041 Uiso 1 1 calc R . . . .
C2 C 0.3013(3) 0.6986(2) 0.16598(9) 0.0402(5) Uani 1 1 d . . . . .
H2A H 0.285516 0.764468 0.136967 0.048 Uiso 1 1 calc R . . . .
H2B H 0.290758 0.622598 0.143744 0.048 Uiso 1 1 calc R . . . .
C3 C 0.4819(3) 0.70700(18) 0.19422(9) 0.0358(4) Uani 1 1 d . . . . .
H3A H 0.570257 0.692017 0.162953 0.043 Uiso 1 1 calc R . . . .
H3B H 0.500040 0.788371 0.210056 0.043 Uiso 1 1 calc R . . . .
C4 C 0.5036(2) 0.61821(16) 0.24455(8) 0.0260(3) Uani 1 1 d . . . . .
C5 C 0.3655(2) 0.62722(14) 0.29232(7) 0.0213(3) Uani 1 1 d . . . . .
H5 H 0.370373 0.710366 0.308233 0.026 Uiso 1 1 calc R . . . .
C6 C 0.1831(2) 0.61118(15) 0.26403(7) 0.0230(3) Uani 1 1 d . . . . .
C7 C 0.0484(2) 0.63558(15) 0.31313(7) 0.0264(4) Uani 1 1 d . . . . .
H7A H 0.046032 0.722305 0.320844 0.032 Uiso 1 1 calc R . . . .
H7B H -0.066428 0.612916 0.297310 0.032 Uiso 1 1 calc R . . . .
C8 C 0.0750(2) 0.57242(15) 0.37272(8) 0.0240(3) Uani 1 1 d . . . . .
H8 H 0.000690 0.611593 0.403700 0.029 Uiso 1 1 calc R . . . .
C9 C 0.2605(2) 0.56826(14) 0.39636(7) 0.0210(3) Uani 1 1 d . . . . .
H9 H 0.289555 0.643114 0.418463 0.025 Uiso 1 1 calc R . . . .
C10 C 0.3915(2) 0.54492(14) 0.34601(7) 0.0204(3) Uani 1 1 d . . . . .
H10A H 0.509678 0.555991 0.362030 0.024 Uiso 1 1 calc R . . . .
H10B H 0.380676 0.461322 0.332522 0.024 Uiso 1 1 calc R . . . .
C11 C 0.2469(2) 0.46275(15) 0.44004(7) 0.0227(3) Uani 1 1 d . . . . .
H11 H 0.191252 0.491621 0.477908 0.027 Uiso 1 1 calc R . . . .
C12 C 0.1199(2) 0.38247(17) 0.40782(7) 0.0268(4) Uani 1 1 d . . . . .
C13 C 0.6307(2) 0.53945(18) 0.24502(8) 0.0326(4) Uani 1 1 d . . . . .
H13A H 0.711784 0.537673 0.212992 0.039 Uiso 1 1 calc R . . . .
H13B H 0.640725 0.484718 0.277387 0.039 Uiso 1 1 calc R . . . .
C14 C 0.1593(2) 0.48578(16) 0.23724(7) 0.0276(4) Uani 1 1 d . . . . .
H14A H 0.251589 0.470029 0.208153 0.041 Uiso 1 1 calc GR . . . .
H14B H 0.047164 0.481017 0.216998 0.041 Uiso 1 1 calc GR . . . .
H14C H 0.164149 0.426570 0.269550 0.041 Uiso 1 1 calc GR . . . .
C15 C 0.4141(2) 0.39922(14) 0.45686(7) 0.0237(3) Uani 1 1 d . . . . .
H15A H 0.387652 0.332385 0.484362 0.028 Uiso 1 1 calc R . . . .
H15B H 0.467680 0.365836 0.420135 0.028 Uiso 1 1 calc R . . . .
C16 C 0.7138(2) 0.43604(17) 0.48392(8) 0.0293(4) Uani 1 1 d . . . . .
H16A H 0.765859 0.449361 0.443823 0.035 Uiso 1 1 calc R . . . .
H16B H 0.719251 0.350183 0.493667 0.035 Uiso 1 1 calc R . . . .
C17 C 0.8035(2) 0.5100(2) 0.53168(9) 0.0381(5) Uani 1 1 d . . . . .
H17A H 0.831027 0.590586 0.516550 0.046 Uiso 1 1 calc R . . . .
H17B H 0.911067 0.471123 0.545548 0.046 Uiso 1 1 calc R . . . .
C18 C 0.6695(3) 0.51485(19) 0.58172(9) 0.0367(4) Uani 1 1 d . . . . .
H18A H 0.677699 0.590782 0.604098 0.044 Uiso 1 1 calc R . . . .
H18B H 0.685606 0.448132 0.610234 0.044 Uiso 1 1 calc R . . . .
C19 C 0.4939(2) 0.50478(14) 0.54934(7) 0.0233(3) Uani 1 1 d . . . . .
H19 H 0.425749 0.437444 0.566693 0.028 Uiso 1 1 calc R . . . .
C20 C 0.3921(2) 0.61986(15) 0.55468(7) 0.0244(3) Uani 1 1 d . . . . .
C21 C 0.1465(3) 0.7094(2) 0.59727(10) 0.0443(5) Uani 1 1 d . . . . .
H21A H 0.118646 0.748348 0.559061 0.066 Uiso 1 1 calc GR . . . .
H21B H 0.213039 0.764070 0.622587 0.066 Uiso 1 1 calc GR . . . .
H21C H 0.039460 0.687389 0.617963 0.066 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.472(2) . ?
O1 C12 1.349(2) . ?
O2 C12 1.203(2) . ?
O3 C20 1.198(2) . ?
O4 C20 1.329(2) . ?
O4 C21 1.446(2) . ?
N1 C15 1.457(2) . ?
N1 C16 1.466(2) . ?
N1 C19 1.473(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.524(3) . ?
C1 C6 1.542(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.536(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.509(2) . ?
C4 C5 1.510(2) . ?
C4 C13 1.324(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.557(2) . ?
C5 C10 1.524(2) . ?
C6 C7 1.535(2) . ?
C6 C14 1.541(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.517(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.531(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.533(2) . ?
C9 C11 1.537(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11 1.0000 . ?
C11 C12 1.515(2) . ?
C11 C15 1.525(2) . ?
C13 H13A 0.9500 . ?
C13 H13B 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.517(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.523(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.543(2) . ?
C19 H19 1.0000 . ?
C19 C20 1.519(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C12 O1 C8 109.14(12) . . ?
C20 O4 C21 115.76(16) . . ?
C15 N1 C16 112.67(13) . . ?
C15 N1 C19 113.69(13) . . ?
C16 N1 C19 107.44(13) . . ?
H1A C1 H1B 107.7 . . ?
C2 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C2 C1 C6 113.28(15) . . ?
C6 C1 H1A 108.9 . . ?
C6 C1 H1B 108.9 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C1 C2 C3 110.95(16) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.32(15) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C3 C4 C5 113.49(15) . . ?
C13 C4 C3 122.06(16) . . ?
C13 C4 C5 124.45(15) . . ?
C4 C5 H5 106.6 . . ?
C4 C5 C6 110.52(13) . . ?
C4 C5 C10 114.64(13) . . ?
C6 C5 H5 106.6 . . ?
C10 C5 H5 106.6 . . ?
C10 C5 C6 111.47(13) . . ?
C1 C6 C5 108.09(14) . . ?
C7 C6 C1 108.45(14) . . ?
C7 C6 C5 107.98(13) . . ?
C7 C6 C14 110.93(14) . . ?
C14 C6 C1 109.55(14) . . ?
C14 C6 C5 111.73(14) . . ?
C6 C7 H7A 108.2 . . ?
C6 C7 H7B 108.2 . . ?
H7A C7 H7B 107.3 . . ?
C8 C7 C6 116.45(14) . . ?
C8 C7 H7A 108.2 . . ?
C8 C7 H7B 108.2 . . ?
O1 C8 C7 111.00(13) . . ?
O1 C8 H8 108.5 . . ?
O1 C8 C9 103.83(12) . . ?
C7 C8 H8 108.5 . . ?
C7 C8 C9 116.21(14) . . ?
C9 C8 H8 108.5 . . ?
C8 C9 H9 110.7 . . ?
C8 C9 C10 112.06(13) . . ?
C8 C9 C11 100.15(13) . . ?
C10 C9 H9 110.7 . . ?
C10 C9 C11 112.02(13) . . ?
C11 C9 H9 110.7 . . ?
C5 C10 C9 112.39(13) . . ?
C5 C10 H10A 109.1 . . ?
C5 C10 H10B 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C9 C11 H11 108.1 . . ?
C12 C11 C9 101.85(12) . . ?
C12 C11 H11 108.1 . . ?
C12 C11 C15 112.86(14) . . ?
C15 C11 C9 117.26(13) . . ?
C15 C11 H11 108.1 . . ?
O1 C12 C11 110.05(15) . . ?
O2 C12 O1 121.60(16) . . ?
O2 C12 C11 128.35(16) . . ?
C4 C13 H13A 120.0 . . ?
C4 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C11 111.45(13) . . ?
N1 C15 H15A 109.3 . . ?
N1 C15 H15B 109.3 . . ?
C11 C15 H15A 109.3 . . ?
C11 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
N1 C16 H16A 111.2 . . ?
N1 C16 H16B 111.2 . . ?
N1 C16 C17 103.06(15) . . ?
H16A C16 H16B 109.1 . . ?
C17 C16 H16A 111.2 . . ?
C17 C16 H16B 111.2 . . ?
C16 C17 H17A 111.2 . . ?
C16 C17 H17B 111.2 . . ?
C16 C17 C18 102.65(15) . . ?
H17A C17 H17B 109.1 . . ?
C18 C17 H17A 111.2 . . ?
C18 C17 H17B 111.2 . . ?
C17 C18 H18A 110.8 . . ?
C17 C18 H18B 110.8 . . ?
C17 C18 C19 104.91(14) . . ?
H18A C18 H18B 108.8 . . ?
C19 C18 H18A 110.8 . . ?
C19 C18 H18B 110.8 . . ?
N1 C19 C18 105.51(14) . . ?
N1 C19 H19 109.9 . . ?
N1 C19 C20 110.52(13) . . ?
C18 C19 H19 109.9 . . ?
C20 C19 C18 111.01(14) . . ?
C20 C19 H19 109.9 . . ?
O3 C20 O4 123.70(17) . . ?
O3 C20 C19 125.13(16) . . ?
O4 C20 C19 111.14(15) . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
