# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_Yidong1_a
_database_code_depnum_ccdc_archive 'CCDC 1909839'
loop_
_audit_author_name
_audit_author_address
'Steven J. Geib'
;UNIVERSITY OF PITTSBURGH
United States of America
;
_audit_update_record             
;
2019-04-12 deposited with the CCDC.	2020-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H24'
_chemical_formula_weight         372.48

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.6092(4)
_cell_length_b                   24.7359(10)
_cell_length_c                   9.7874(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.350(2)
_cell_angle_gamma                90
_cell_volume                     2084.67(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4203
_cell_measurement_theta_min      3.074
_cell_measurement_theta_max      68.150

_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.503
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker X8 Prospector Ultra IMuS'
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13085
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.574
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.97
_reflns_number_total             3689
_reflns_number_gt                3093
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0680P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3689
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.15400(15) 0.37839(5) 0.40502(14) 0.0244(3) Uani 1 1 d . . . . .
C2 C 0.27125(14) 0.35338(5) 0.47186(14) 0.0235(3) Uani 1 1 d . . . . .
C3 C 0.41572(14) 0.32159(5) 0.54275(14) 0.0227(3) Uani 1 1 d . . . . .
H3A H 0.385076 0.282834 0.540300 0.027 Uiso 1 1 calc R U . . .
C4 C 0.50122(16) 0.32641(6) 0.44298(15) 0.0294(3) Uani 1 1 d . . . . .
H4A H 0.597697 0.305451 0.488710 0.044 Uiso 1 1 calc R U . . .
H4B H 0.434977 0.312411 0.340784 0.044 Uiso 1 1 calc R U . . .
H4C H 0.525572 0.364464 0.435724 0.044 Uiso 1 1 calc R U . . .
C5 C -0.04642(15) 0.42372(5) 0.17783(15) 0.0276(3) Uani 1 1 d . . . . .
H5A H 0.000093 0.409655 0.117573 0.033 Uiso 1 1 calc R U . . .
C6 C -0.17549(15) 0.45695(6) 0.11178(16) 0.0317(3) Uani 1 1 d . . . . .
H6A H -0.216889 0.465673 0.006518 0.038 Uiso 1 1 calc R U . . .
C7 C -0.24420(16) 0.47743(6) 0.19839(17) 0.0370(4) Uani 1 1 d . . . . .
H7A H -0.332380 0.500350 0.153010 0.044 Uiso 1 1 calc R U . . .
C8 C -0.18404(17) 0.46443(7) 0.35157(17) 0.0399(4) Uani 1 1 d . . . . .
H8A H -0.231589 0.478352 0.411057 0.048 Uiso 1 1 calc R U . . .
C9 C -0.05505(16) 0.43128(6) 0.41874(16) 0.0315(3) Uani 1 1 d . . . . .
H9A H -0.014761 0.422512 0.523899 0.038 Uiso 1 1 calc R U . . .
C10 C 0.01571(14) 0.41078(5) 0.33292(15) 0.0241(3) Uani 1 1 d . . . . .
C11 C 0.51909(13) 0.33681(5) 0.71464(14) 0.0208(3) Uani 1 1 d . . . . .
C12 C 0.29676(14) 0.30261(5) 0.76971(15) 0.0256(3) Uani 1 1 d . . . . .
H12A H 0.268226 0.278522 0.685961 0.031 Uiso 1 1 calc R U . . .
C13 C 0.21291(16) 0.30231(6) 0.85431(16) 0.0321(3) Uani 1 1 d . . . . .
H13A H 0.127802 0.278219 0.827595 0.039 Uiso 1 1 calc R U . . .
C14 C 0.25216(16) 0.33676(6) 0.97705(16) 0.0341(3) Uani 1 1 d . . . . .
H14A H 0.193665 0.336956 1.033853 0.041 Uiso 1 1 calc R U . . .
C15 C 0.37830(16) 0.37106(6) 1.01603(16) 0.0328(3) Uani 1 1 d . . . . .
H15A H 0.407595 0.394535 1.101154 0.039 Uiso 1 1 calc R U . . .
C16 C 0.46151(15) 0.37122(5) 0.93166(14) 0.0260(3) Uani 1 1 d . . . . .
H16A H 0.547876 0.394862 0.960371 0.031 Uiso 1 1 calc R U . . .
C17 C 0.42208(14) 0.33755(5) 0.80514(14) 0.0207(3) Uani 1 1 d . . . . .
C18 C 0.50291(15) 0.43949(5) 0.69369(14) 0.0243(3) Uani 1 1 d . . . . .
H18A H 0.399714 0.436668 0.682293 0.029 Uiso 1 1 calc R U . . .
C19 C 0.56232(16) 0.49004(6) 0.68730(15) 0.0306(3) Uani 1 1 d . . . . .
H19A H 0.499819 0.521326 0.672177 0.037 Uiso 1 1 calc R U . . .
C20 C 0.71157(16) 0.49517(6) 0.70275(15) 0.0341(3) Uani 1 1 d . . . . .
H20A H 0.752582 0.529825 0.699411 0.041 Uiso 1 1 calc R U . . .
C21 C 0.80085(16) 0.44920(6) 0.72319(16) 0.0342(3) Uani 1 1 d . . . . .
H21A H 0.903526 0.452351 0.733326 0.041 Uiso 1 1 calc R U . . .
C22 C 0.74135(15) 0.39832(6) 0.72902(15) 0.0284(3) Uani 1 1 d . . . . .
H22A H 0.803579 0.367131 0.741656 0.034 Uiso 1 1 calc R U . . .
C23 C 0.59194(14) 0.39254(5) 0.71660(13) 0.0216(3) Uani 1 1 d . . . . .
C24 C 0.76385(15) 0.30437(5) 0.93900(15) 0.0281(3) Uani 1 1 d . . . . .
H24A H 0.762857 0.337723 0.986676 0.034 Uiso 1 1 calc R U . . .
C25 C 0.88137(15) 0.26744(6) 1.01577(16) 0.0325(3) Uani 1 1 d . . . . .
H25A H 0.960501 0.275987 1.114340 0.039 Uiso 1 1 calc R U . . .
C26 C 0.88434(16) 0.21825(6) 0.95003(16) 0.0323(3) Uani 1 1 d . . . . .
H26A H 0.965182 0.193011 1.002377 0.039 Uiso 1 1 calc R U . . .
C27 C 0.76769(16) 0.20640(6) 0.80680(16) 0.0306(3) Uani 1 1 d . . . . .
H27A H 0.767491 0.172458 0.761303 0.037 Uiso 1 1 calc R U . . .
C28 C 0.65087(15) 0.24356(5) 0.72881(15) 0.0260(3) Uani 1 1 d . . . . .
H28A H 0.572364 0.234798 0.630097 0.031 Uiso 1 1 calc R U . . .
C29 C 0.64678(14) 0.29357(5) 0.79290(14) 0.0221(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.1941(18) . ?
C1 C10 1.4399(18) . ?
C2 C3 1.4738(17) . ?
C3 C4 1.5346(17) . ?
C3 C11 1.5733(17) . ?
C3 H3A 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.3856(19) . ?
C5 C10 1.3994(18) . ?
C5 H5A 0.9500 . ?
C6 C7 1.381(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.384(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.385(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.3899(19) . ?
C9 H9A 0.9500 . ?
C11 C23 1.5425(16) . ?
C11 C17 1.5449(17) . ?
C11 C29 1.5499(16) . ?
C12 C13 1.388(2) . ?
C12 C17 1.3952(17) . ?
C12 H12A 0.9500 . ?
C13 C14 1.382(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.387(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3811(19) . ?
C15 H15A 0.9500 . ?
C16 C17 1.3980(18) . ?
C16 H16A 0.9500 . ?
C18 C19 1.3876(18) . ?
C18 C23 1.4001(18) . ?
C18 H18A 0.9500 . ?
C19 C20 1.380(2) . ?
C19 H19A 0.9500 . ?
C20 C21 1.385(2) . ?
C20 H20A 0.9500 . ?
C21 C22 1.3938(19) . ?
C21 H21A 0.9500 . ?
C22 C23 1.3934(18) . ?
C22 H22A 0.9500 . ?
C24 C25 1.3861(18) . ?
C24 C29 1.3977(18) . ?
C24 H24A 0.9500 . ?
C25 C26 1.382(2) . ?
C25 H25A 0.9500 . ?
C26 C27 1.383(2) . ?
C26 H26A 0.9500 . ?
C27 C28 1.3882(18) . ?
C27 H27A 0.9500 . ?
C28 C29 1.3953(17) . ?
C28 H28A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 176.30(14) . . ?
C1 C2 C3 175.53(13) . . ?
C2 C3 C4 108.51(10) . . ?
C2 C3 C11 113.04(10) . . ?
C4 C3 C11 113.55(10) . . ?
C2 C3 H3A 107.1 . . ?
C4 C3 H3A 107.1 . . ?
C11 C3 H3A 107.1 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 120.28(13) . . ?
C6 C5 H5A 119.9 . . ?
C10 C5 H5A 119.9 . . ?
C7 C6 C5 120.27(13) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C6 C7 C8 119.72(13) . . ?
C6 C7 H7A 120.1 . . ?
C8 C7 H7A 120.1 . . ?
C7 C8 C9 120.49(14) . . ?
C7 C8 H8A 119.8 . . ?
C9 C8 H8A 119.8 . . ?
C8 C9 C10 120.26(13) . . ?
C8 C9 H9A 119.9 . . ?
C10 C9 H9A 119.9 . . ?
C9 C10 C5 118.98(12) . . ?
C9 C10 C1 119.96(12) . . ?
C5 C10 C1 121.03(12) . . ?
C23 C11 C17 111.61(10) . . ?
C23 C11 C29 110.81(10) . . ?
C17 C11 C29 105.76(9) . . ?
C23 C11 C3 107.15(10) . . ?
C17 C11 C3 111.14(9) . . ?
C29 C11 C3 110.42(10) . . ?
C13 C12 C17 121.36(12) . . ?
C13 C12 H12A 119.3 . . ?
C17 C12 H12A 119.3 . . ?
C14 C13 C12 120.57(13) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C13 C14 C15 118.97(13) . . ?
C13 C14 H14A 120.5 . . ?
C15 C14 H14A 120.5 . . ?
C16 C15 C14 120.30(13) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C15 C16 C17 121.78(12) . . ?
C15 C16 H16A 119.1 . . ?
C17 C16 H16A 119.1 . . ?
C12 C17 C16 117.00(12) . . ?
C12 C17 C11 121.60(11) . . ?
C16 C17 C11 121.31(11) . . ?
C19 C18 C23 121.35(13) . . ?
C19 C18 H18A 119.3 . . ?
C23 C18 H18A 119.3 . . ?
C20 C19 C18 120.43(13) . . ?
C20 C19 H19A 119.8 . . ?
C18 C19 H19A 119.8 . . ?
C19 C20 C21 119.18(13) . . ?
C19 C20 H20A 120.4 . . ?
C21 C20 H20A 120.4 . . ?
C20 C21 C22 120.56(13) . . ?
C20 C21 H21A 119.7 . . ?
C22 C21 H21A 119.7 . . ?
C23 C22 C21 120.97(13) . . ?
C23 C22 H22A 119.5 . . ?
C21 C22 H22A 119.5 . . ?
C22 C23 C18 117.49(12) . . ?
C22 C23 C11 122.49(11) . . ?
C18 C23 C11 119.84(11) . . ?
C25 C24 C29 121.38(12) . . ?
C25 C24 H24A 119.3 . . ?
C29 C24 H24A 119.3 . . ?
C26 C25 C24 120.52(13) . . ?
C26 C25 H25A 119.7 . . ?
C24 C25 H25A 119.7 . . ?
C25 C26 C27 118.91(12) . . ?
C25 C26 H26A 120.5 . . ?
C27 C26 H26A 120.5 . . ?
C26 C27 C28 120.72(13) . . ?
C26 C27 H27A 119.6 . . ?
C28 C27 H27A 119.6 . . ?
C27 C28 C29 121.13(12) . . ?
C27 C28 H28A 119.4 . . ?
C29 C28 H28A 119.4 . . ?
C28 C29 C24 117.32(12) . . ?
C28 C29 C11 124.31(11) . . ?
C24 C29 C11 118.35(11) . . ?

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_wyd2_282
_database_code_depnum_ccdc_archive 'CCDC 1909840'
loop_
_audit_author_name
_audit_author_address
'Steven J. Geib'
;UNIVERSITY OF PITTSBURGH
United States of America
;
_audit_update_record             
;
2019-04-12 deposited with the CCDC.	2020-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 N O4'
_chemical_formula_weight         365.41

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   17.0265(10)
_cell_length_b                   14.1187(8)
_cell_length_c                   8.9890(5)
_cell_angle_alpha                90
_cell_angle_beta                 118.511(2)
_cell_angle_gamma                90
_cell_volume                     1898.82(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      4.305
_cell_measurement_theta_max      70.063

_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.712
_shelx_estimated_absorpt_T_min   0.859
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker AXS X8 Prospector Ultra IMuS'
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15496
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.305
_diffrn_reflns_theta_max         70.057
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3528
_reflns_number_gt                3509
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.953
_reflns_Friedel_fraction_max     0.957
_reflns_Friedel_fraction_full    0.961

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0680P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1693 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3528
_refine_ls_number_parameters     247
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0773
_refine_ls_wR_factor_gt          0.0771
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.52720(8) 0.90024(8) 0.89399(15) 0.0389(3) Uani 1 1 d . . . . .
C1 C 0.33546(9) 0.74482(10) 0.71371(18) 0.0276(3) Uani 1 1 d . . . . .
H1A H 0.320972 0.765618 0.597043 0.033 Uiso 1 1 calc R U . . .
N1 N 0.41538(9) 0.79531(9) 0.83588(16) 0.0312(3) Uani 1 1 d . . . . .
O2 O 0.40962(7) 0.88826(8) 0.63070(14) 0.0357(3) Uani 1 1 d . . . . .
C2 C 0.35301(9) 0.63878(10) 0.72830(18) 0.0265(3) Uani 1 1 d . . . . .
O3 O 0.37742(8) 0.34577(8) 0.74819(15) 0.0376(3) Uani 1 1 d . . . . .
C3 C 0.29408(9) 0.58053(10) 0.59521(18) 0.0269(3) Uani 1 1 d . . . . .
H3A H 0.246715 0.608438 0.497307 0.032 Uiso 1 1 calc R U . . .
O4 O 0.24913(7) 0.42072(7) 0.48339(14) 0.0355(3) Uani 1 1 d . . . . .
C4 C 0.30381(10) 0.48353(10) 0.60426(19) 0.0283(3) Uani 1 1 d . . . . .
C5 C 0.37428(10) 0.44232(10) 0.7495(2) 0.0296(3) Uani 1 1 d . . . . .
C6 C 0.43299(9) 0.49986(12) 0.87958(18) 0.0308(3) Uani 1 1 d . . . . .
H6A H 0.481174 0.472075 0.976377 0.037 Uiso 1 1 calc R U . . .
C7 C 0.42261(9) 0.59848(11) 0.87101(17) 0.0291(3) Uani 1 1 d . . . . .
C8 C 0.48802(11) 0.65802(12) 1.01774(18) 0.0342(3) Uani 1 1 d . . . . .
H8A H 0.546125 0.659107 1.017620 0.041 Uiso 1 1 calc R U . . .
H8B H 0.497669 0.628631 1.125168 0.041 Uiso 1 1 calc R U . . .
C9 C 0.45518(11) 0.75932(12) 1.00925(18) 0.0331(3) Uani 1 1 d . . . . .
H9A H 0.410245 0.761094 1.049420 0.040 Uiso 1 1 calc R U . . .
H9B H 0.505915 0.800280 1.084467 0.040 Uiso 1 1 calc R U . . .
C10 C 0.45654(10) 0.86422(10) 0.79514(18) 0.0283(3) Uani 1 1 d . . . . .
C11 C 0.44797(13) 0.96247(14) 0.5766(2) 0.0454(4) Uani 1 1 d . . . . .
H11A H 0.405389 0.981428 0.460809 0.068 Uiso 1 1 calc R U . . .
H11B H 0.503078 0.939578 0.579749 0.068 Uiso 1 1 calc R U . . .
H11C H 0.461609 1.017036 0.652393 0.068 Uiso 1 1 calc R U . . .
C12 C 0.25406(10) 0.76676(10) 0.7419(2) 0.0321(3) Uani 1 1 d . . . . .
H12A H 0.200522 0.734897 0.652421 0.039 Uiso 1 1 calc R U . . .
H12B H 0.265436 0.740071 0.852220 0.039 Uiso 1 1 calc R U . . .
C13 C 0.23553(10) 0.86826(12) 0.73955(19) 0.0316(3) Uani 1 1 d . . . . .
C14 C 0.21919(10) 0.95115(11) 0.73659(19) 0.0313(3) Uani 1 1 d . . . . .
C15 C 0.19907(10) 1.05052(10) 0.72796(18) 0.0289(3) Uani 1 1 d . . . . .
C16 C 0.23141(12) 1.11251(12) 0.6487(2) 0.0392(4) Uani 1 1 d . . . . .
H16A H 0.266314 1.088689 0.600301 0.047 Uiso 1 1 calc R U . . .
C17 C 0.21289(15) 1.20869(13) 0.6403(3) 0.0471(4) Uani 1 1 d . . . . .
H17A H 0.235255 1.250481 0.586468 0.057 Uiso 1 1 calc R U . . .
C18 C 0.16206(15) 1.24362(12) 0.7099(2) 0.0475(5) Uani 1 1 d . . . . .
H18A H 0.149542 1.309488 0.704253 0.057 Uiso 1 1 calc R U . . .
C19 C 0.12930(15) 1.18290(14) 0.7878(2) 0.0484(5) Uani 1 1 d . . . . .
H19A H 0.094136 1.207212 0.835239 0.058 Uiso 1 1 calc R U . . .
C20 C 0.14743(13) 1.08666(12) 0.7970(2) 0.0386(4) Uani 1 1 d . . . . .
H20A H 0.124595 1.045315 0.850611 0.046 Uiso 1 1 calc R U . . .
C21 C 0.44395(15) 0.30168(12) 0.8977(3) 0.0473(4) Uani 1 1 d . . . . .
H21A H 0.438986 0.232720 0.883822 0.071 Uiso 1 1 calc R U . . .
H21B H 0.435405 0.319924 0.994161 0.071 Uiso 1 1 calc R U . . .
H21C H 0.503293 0.322002 0.918002 0.071 Uiso 1 1 calc R U . . .
C22 C 0.17563(11) 0.46040(11) 0.3375(2) 0.0376(3) Uani 1 1 d . . . . .
H22A H 0.139940 0.409365 0.261258 0.056 Uiso 1 1 calc R U . . .
H22B H 0.198094 0.501832 0.278717 0.056 Uiso 1 1 calc R U . . .
H22C H 0.138345 0.497265 0.372188 0.056 Uiso 1 1 calc R U . . .


_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 C10 1.214(2) . ?
C1 N1 1.4627(18) . ?
C1 C2 1.5200(19) . ?
C1 C12 1.554(2) . ?
C1 H1A 1.0000 . ?
N1 C10 1.348(2) . ?
N1 C9 1.4622(19) . ?
O2 C10 1.3457(19) . ?
O2 C11 1.4366(19) . ?
C2 C7 1.387(2) . ?
C2 C3 1.403(2) . ?
O3 C5 1.3645(17) . ?
O3 C21 1.422(2) . ?
C3 C4 1.3773(19) . ?
C3 H3A 0.9500 . ?
O4 C4 1.3667(18) . ?
O4 C22 1.426(2) . ?
C4 C5 1.410(2) . ?
C5 C6 1.382(2) . ?
C6 C7 1.401(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.511(2) . ?
C8 C9 1.524(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.465(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.200(2) . ?
C14 C15 1.4374(19) . ?
C15 C20 1.393(2) . ?
C15 C16 1.397(2) . ?
C16 C17 1.388(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.379(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.382(3) . ?
C18 H18A 0.9500 . ?
C19 C20 1.387(2) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
N1 C1 C2 109.94(12) . . ?
N1 C1 C12 111.29(12) . . ?
C2 C1 C12 109.64(11) . . ?
N1 C1 H1A 108.6 . . ?
C2 C1 H1A 108.6 . . ?
C12 C1 H1A 108.6 . . ?
C10 N1 C1 124.46(12) . . ?
C10 N1 C9 120.26(12) . . ?
C1 N1 C9 115.00(12) . . ?
C10 O2 C11 115.35(12) . . ?
C7 C2 C3 119.73(13) . . ?
C7 C2 C1 122.01(13) . . ?
C3 C2 C1 118.20(12) . . ?
C5 O3 C21 116.48(13) . . ?
C4 C3 C2 121.04(13) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C4 O4 C22 116.24(11) . . ?
O4 C4 C3 125.53(13) . . ?
O4 C4 C5 115.10(12) . . ?
C3 C4 C5 119.36(13) . . ?
O3 C5 C6 125.38(14) . . ?
O3 C5 C4 115.08(13) . . ?
C6 C5 C4 119.54(13) . . ?
C5 C6 C7 121.08(13) . . ?
C5 C6 H6A 119.5 . . ?
C7 C6 H6A 119.5 . . ?
C2 C7 C6 119.24(13) . . ?
C2 C7 C8 121.83(13) . . ?
C6 C7 C8 118.93(13) . . ?
C7 C8 C9 112.23(13) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 C8 110.59(12) . . ?
N1 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
O1 C10 N1 124.43(14) . . ?
O1 C10 O2 124.02(14) . . ?
N1 C10 O2 111.55(12) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C1 113.28(12) . . ?
C13 C12 H12A 108.9 . . ?
C1 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C1 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 179.15(15) . . ?
C13 C14 C15 178.32(15) . . ?
C20 C15 C16 118.96(14) . . ?
C20 C15 C14 121.21(14) . . ?
C16 C15 C14 119.83(14) . . ?
C17 C16 C15 120.43(16) . . ?
C17 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?
C18 C17 C16 120.04(16) . . ?
C18 C17 H17A 120.0 . . ?
C16 C17 H17A 120.0 . . ?
C19 C18 C17 120.05(15) . . ?
C19 C18 H18A 120.0 . . ?
C17 C18 H18A 120.0 . . ?
C18 C19 C20 120.41(17) . . ?
C18 C19 H19A 119.8 . . ?
C20 C19 H19A 119.8 . . ?
C15 C20 C19 120.11(16) . . ?
C15 C20 H20A 119.9 . . ?
C19 C20 H20A 119.9 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.113
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.030

