# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_a
_database_code_depnum_ccdc_archive 'CCDC 2032397'
loop_
_audit_author_name
_audit_author_address
'Zhuangzhi Shi'
;Nanjing University
China
;
_audit_update_record             
;
2020-09-16 deposited with the CCDC.	2021-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H30 B F2 N O5'
_chemical_formula_weight         425.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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'
B B 0.0070 0.0029 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   14.1856(8)
_cell_length_b                   17.0247(8)
_cell_length_c                   9.5406(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.364(3)
_cell_angle_gamma                90
_cell_volume                     2297.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    3893
_cell_measurement_theta_min      3.53
_cell_measurement_theta_max      50.77

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.515
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17884
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.718
_diffrn_reflns_theta_max         54.137
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4231
_reflns_number_gt                2347
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1283P)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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0040(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4231
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_ref         0.2237
_refine_ls_wR_factor_gt          0.1819
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
B1 B 0.4490(2) 0.3602(2) 0.6383(4) 0.0504(9) Uani 1 1 d . . . . .
C1 C 0.8789(2) 0.1134(2) 0.7704(4) 0.0652(10) Uani 1 1 d . . . . .
H1A H 0.826117 0.077835 0.784161 0.098 Uiso 1 1 calc R U . . .
H1B H 0.934971 0.082641 0.751550 0.098 Uiso 1 1 calc R U . . .
H1C H 0.862072 0.148166 0.690534 0.098 Uiso 1 1 calc R U . . .
C2 C 0.9732(2) 0.2259(2) 0.8752(4) 0.0694(11) Uani 1 1 d . . . . .
H2A H 0.950191 0.257660 0.793981 0.104 Uiso 1 1 calc R U . . .
H2B H 1.033153 0.200981 0.856082 0.104 Uiso 1 1 calc R U . . .
H2C H 0.983032 0.259763 0.958170 0.104 Uiso 1 1 calc R U . . .
C3 C 0.9389(2) 0.1098(2) 1.0219(4) 0.0630(9) Uani 1 1 d . . . . .
H3A H 0.958184 0.142017 1.104267 0.095 Uiso 1 1 calc R U . . .
H3B H 0.993646 0.080673 0.992565 0.095 Uiso 1 1 calc R U . . .
H3C H 0.889836 0.072670 1.045982 0.095 Uiso 1 1 calc R U . . .
C4 C 0.9001(2) 0.16249(16) 0.9025(3) 0.0435(7) Uani 1 1 d . . . . .
C5 C 0.8124(2) 0.20559(16) 0.9463(3) 0.0428(7) Uani 1 1 d . . . . .
C6 C 0.8782(3) 0.5911(2) 0.9658(5) 0.0764(12) Uani 1 1 d . . . . .
C7 C 0.7608(2) 0.51480(18) 1.0218(4) 0.0579(9) Uani 1 1 d . . . . .
C8 C 0.8074(2) 0.47769(18) 0.9214(4) 0.0552(8) Uani 1 1 d . . . . .
C9 C 0.7842(2) 0.40463(17) 0.8720(3) 0.0497(8) Uani 1 1 d . . . . .
H9 H 0.817076 0.380092 0.800821 0.060 Uiso 1 1 calc R U . . .
C10 C 0.7091(2) 0.36790(17) 0.9323(3) 0.0440(7) Uani 1 1 d . . . . .
C11 C 0.6623(2) 0.40623(17) 1.0355(3) 0.0501(8) Uani 1 1 d . . . . .
H11 H 0.611656 0.379908 1.075364 0.060 Uiso 1 1 calc R U . . .
C12 C 0.6864(2) 0.48170(18) 1.0830(3) 0.0569(9) Uani 1 1 d . . . . .
H12 H 0.653598 0.507994 1.152378 0.068 Uiso 1 1 calc R U . . .
C13 C 0.6745(2) 0.28834(16) 0.8783(3) 0.0422(7) Uani 1 1 d . . . . .
H13 H 0.639595 0.262578 0.952979 0.051 Uiso 1 1 calc R U . . .
C14 C 0.6070(2) 0.29679(17) 0.7465(3) 0.0467(7) Uani 1 1 d . . . . .
H14A H 0.584584 0.243941 0.716307 0.056 Uiso 1 1 calc R U . . .
H14B H 0.642326 0.319031 0.670119 0.056 Uiso 1 1 calc R U . . .
C15 C 0.5212(2) 0.34889(18) 0.7664(3) 0.0521(8) Uani 1 1 d . . . . .
H15A H 0.544563 0.401405 0.797036 0.063 Uiso 1 1 calc R U . . .
H15B H 0.487195 0.326603 0.844039 0.063 Uiso 1 1 calc R U . . .
C16 C 0.3680(3) 0.3474(2) 0.4222(4) 0.0708(11) Uani 1 1 d . . . . .
C19 C 0.3232(3) 0.4132(2) 0.5085(4) 0.0667(10) Uani 1 1 d . . . . .
F1 F 0.87264(18) 0.65707(12) 0.8895(3) 0.0937(8) Uani 1 1 d . . . . .
F2 F 0.95860(17) 0.59601(13) 1.0463(3) 0.1034(9) Uani 1 1 d . . . . .
N1 N 0.75310(16) 0.23679(13) 0.8455(3) 0.0443(6) Uani 1 1 d . . . . .
H1 H 0.761359 0.226142 0.757043 0.053 Uiso 1 1 calc R U . . .
O1 O 0.45140(17) 0.32503(15) 0.5120(3) 0.0759(8) Uani 1 1 d . . . . .
O2 O 0.3742(2) 0.40829(17) 0.6425(3) 0.0898(10) Uani 1 1 d . . . . .
O3 O 0.79894(14) 0.21360(12) 1.0723(2) 0.0548(6) Uani 1 1 d . . . . .
O4 O 0.80323(19) 0.58795(13) 1.0492(3) 0.0740(8) Uani 1 1 d . . . . .
O5 O 0.87956(16) 0.52703(14) 0.8800(3) 0.0729(8) Uani 1 1 d . . . . .
C23 C 0.2199(3) 0.4028(4) 0.5270(7) 0.131(2) Uani 1 1 d . . . . .
H23A H 0.209316 0.351083 0.567907 0.196 Uiso 1 1 calc R U . . .
H23B H 0.183984 0.406911 0.435421 0.196 Uiso 1 1 calc R U . . .
H23C H 0.198950 0.443791 0.589800 0.196 Uiso 1 1 calc R U . . .
C21 C 0.3069(4) 0.2740(3) 0.4066(8) 0.134(2) Uani 1 1 d . . . . .
H21A H 0.345417 0.229742 0.378608 0.201 Uiso 1 1 calc R U . . .
H21B H 0.255008 0.282981 0.334538 0.201 Uiso 1 1 calc R U . . .
H21C H 0.280939 0.262128 0.496449 0.201 Uiso 1 1 calc R U . . .
C22 C 0.4019(5) 0.3733(5) 0.2849(6) 0.169(3) Uani 1 1 d . . . . .
H22A H 0.449358 0.414748 0.301470 0.253 Uiso 1 1 calc R U . . .
H22B H 0.348448 0.393482 0.224368 0.253 Uiso 1 1 calc R U . . .
H22C H 0.430156 0.328527 0.238850 0.253 Uiso 1 1 calc R U . . .
C20 C 0.3380(5) 0.4958(3) 0.4549(6) 0.129(2) Uani 1 1 d . . . . .
H20A H 0.324174 0.533830 0.527640 0.193 Uiso 1 1 calc R U . . .
H20B H 0.295645 0.504995 0.370464 0.193 Uiso 1 1 calc R U . . .
H20C H 0.403761 0.501979 0.431841 0.193 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
B1 O2 1.344(4) . ?
B1 O1 1.348(4) . ?
B1 C15 1.545(5) . ?
C1 C4 1.523(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C4 1.533(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.520(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.530(4) . ?
C5 O3 1.239(3) . ?
C5 N1 1.338(4) . ?
C6 F2 1.328(5) . ?
C6 F1 1.337(4) . ?
C6 O5 1.365(5) . ?
C6 O4 1.377(5) . ?
C7 C8 1.361(4) . ?
C7 C12 1.366(5) . ?
C7 O4 1.399(4) . ?
C8 C9 1.362(4) . ?
C8 O5 1.403(4) . ?
C9 C10 1.396(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(4) . ?
C10 C13 1.517(4) . ?
C11 C12 1.396(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 N1 1.471(3) . ?
C13 C14 1.528(4) . ?
C13 H13 1.0000 . ?
C14 C15 1.530(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O1 1.457(4) . ?
C16 C22 1.496(7) . ?
C16 C21 1.521(6) . ?
C16 C19 1.554(5) . ?
C19 O2 1.422(4) . ?
C19 C23 1.500(6) . ?
C19 C20 1.517(6) . ?
N1 H1 0.8800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
O2 B1 O1 111.7(3) . . ?
O2 B1 C15 122.0(3) . . ?
O1 B1 C15 126.3(3) . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C3 C4 C1 109.5(3) . . ?
C3 C4 C2 109.4(3) . . ?
C1 C4 C2 109.9(3) . . ?
C3 C4 C5 109.5(2) . . ?
C1 C4 C5 112.1(2) . . ?
C2 C4 C5 106.4(2) . . ?
O3 C5 N1 121.2(2) . . ?
O3 C5 C4 120.4(3) . . ?
N1 C5 C4 118.3(2) . . ?
F2 C6 F1 106.0(3) . . ?
F2 C6 O5 110.2(3) . . ?
F1 C6 O5 110.4(4) . . ?
F2 C6 O4 109.6(4) . . ?
F1 C6 O4 109.3(3) . . ?
O5 C6 O4 111.2(3) . . ?
C8 C7 C12 122.8(3) . . ?
C8 C7 O4 108.7(3) . . ?
C12 C7 O4 128.5(3) . . ?
C7 C8 C9 123.3(3) . . ?
C7 C8 O5 108.9(3) . . ?
C9 C8 O5 127.8(3) . . ?
C8 C9 C10 116.1(3) . . ?
C8 C9 H9 122.0 . . ?
C10 C9 H9 122.0 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 C13 120.0(2) . . ?
C9 C10 C13 119.8(2) . . ?
C10 C11 C12 122.8(3) . . ?
C10 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
C7 C12 C11 114.8(3) . . ?
C7 C12 H12 122.6 . . ?
C11 C12 H12 122.6 . . ?
N1 C13 C10 112.0(2) . . ?
N1 C13 C14 108.6(2) . . ?
C10 C13 C14 111.2(2) . . ?
N1 C13 H13 108.3 . . ?
C10 C13 H13 108.3 . . ?
C14 C13 H13 108.3 . . ?
C13 C14 C15 114.0(2) . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 B1 117.4(3) . . ?
C14 C15 H15A 108.0 . . ?
B1 C15 H15A 108.0 . . ?
C14 C15 H15B 108.0 . . ?
B1 C15 H15B 108.0 . . ?
H15A C15 H15B 107.2 . . ?
O1 C16 C22 106.9(4) . . ?
O1 C16 C21 105.9(4) . . ?
C22 C16 C21 112.0(5) . . ?
O1 C16 C19 102.9(3) . . ?
C22 C16 C19 115.1(4) . . ?
C21 C16 C19 113.0(4) . . ?
O2 C19 C23 108.8(4) . . ?
O2 C19 C20 106.5(4) . . ?
C23 C19 C20 108.1(4) . . ?
O2 C19 C16 103.5(3) . . ?
C23 C19 C16 114.9(4) . . ?
C20 C19 C16 114.7(4) . . ?
C5 N1 C13 122.0(2) . . ?
C5 N1 H1 119.0 . . ?
C13 N1 H1 119.0 . . ?
B1 O1 C16 109.6(3) . . ?
B1 O2 C19 110.9(3) . . ?
C6 O4 C7 105.5(3) . . ?
C6 O5 C8 105.5(3) . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_20200728ZH_SZZ_WS64_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2032399'
loop_
_audit_author_name
_audit_author_address
'Zhuangzhi Shi'
;Nanjing University
China
;
_audit_update_record             
;
2020-09-16 deposited with the CCDC.	2021-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H34 Cl2 N2 O6 Rh2'
_chemical_formula_weight         699.23

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'
Cl Cl 0.1484 0.1585 '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'
Rh Rh -1.1178 0.9187 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.2163(4)
_cell_length_b                   11.7129(5)
_cell_length_c                   13.3216(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.0060(10)
_cell_angle_gamma                90
_cell_volume                     1367.63(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5684
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.49

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.440
_shelx_estimated_absorpt_T_min   0.846
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12154
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.368
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3123
_reflns_number_gt                2756
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0374P)²+0.5681P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3123
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0804
_refine_ls_wR_factor_gt          0.0764
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_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
Rh01 Rh 0.66526(2) 0.58777(2) 0.56807(2) 0.02539(9) Uani 1 1 d . . . . .
Cl1 Cl 0.44366(9) 0.60755(7) 0.40649(6) 0.03428(18) Uani 1 1 d . . . . .
O1 O 0.5442(2) 0.65445(19) 0.65899(15) 0.0321(5) Uani 1 1 d . . . . .
O3 O 0.8408(3) 0.4948(2) 0.43325(17) 0.0483(7) Uani 1 1 d . . . . .
O2 O 0.7148(3) 0.8077(2) 0.4921(2) 0.0573(7) Uani 1 1 d . . . . .
N1 N 0.7470(3) 0.6012(2) 0.79056(19) 0.0340(6) Uani 1 1 d . . . . .
C7 C 0.8259(3) 0.5748(3) 0.7107(2) 0.0326(7) Uani 1 1 d . . . . .
H7 H 0.866343 0.496834 0.721079 0.039 Uiso 1 1 calc R U . . .
C10 C 0.7604(4) 0.7413(3) 0.5653(3) 0.0368(7) Uani 1 1 d . . . . .
C5 C 0.6080(3) 0.6424(3) 0.7570(2) 0.0311(6) Uani 1 1 d . . . . .
C11 C 0.7779(3) 0.5293(3) 0.4871(2) 0.0326(7) Uani 1 1 d . . . . .
C2 C 0.5084(4) 0.6735(3) 0.8274(3) 0.0390(8) Uani 1 1 d . . . . .
C6 C 0.8380(4) 0.5765(3) 0.9002(3) 0.0472(9) Uani 1 1 d . . . . .
H6A H 0.914540 0.520689 0.900762 0.071 Uiso 1 1 calc R U . . .
H6B H 0.772570 0.547319 0.938039 0.071 Uiso 1 1 calc R U . . .
H6C H 0.886268 0.645278 0.933478 0.071 Uiso 1 1 calc R U . . .
C3 C 0.4424(5) 0.5618(4) 0.8535(3) 0.0563(11) Uani 1 1 d . . . . .
H3A H 0.394279 0.520766 0.789464 0.084 Uiso 1 1 calc R U . . .
H3B H 0.368538 0.578163 0.888910 0.084 Uiso 1 1 calc R U . . .
H3C H 0.523032 0.516182 0.898582 0.084 Uiso 1 1 calc R U . . .
C8 C 0.9537(4) 0.6583(4) 0.7163(3) 0.0498(10) Uani 1 1 d . . . . .
H8A H 1.009994 0.674111 0.789420 0.060 Uiso 1 1 calc R U . . .
H8B H 1.023576 0.625584 0.682659 0.060 Uiso 1 1 calc R U . . .
C1 C 0.3756(5) 0.7476(4) 0.7615(3) 0.0570(11) Uani 1 1 d . . . . .
H1A H 0.415132 0.816072 0.740027 0.085 Uiso 1 1 calc R U . . .
H1B H 0.310820 0.767250 0.803131 0.085 Uiso 1 1 calc R U . . .
H1C H 0.317805 0.705897 0.700140 0.085 Uiso 1 1 calc R U . . .
C9 C 0.8886(5) 0.7647(4) 0.6625(3) 0.0551(11) Uani 1 1 d . . . . .
H9A H 0.967363 0.807066 0.644218 0.066 Uiso 1 1 calc R U . . .
H9B H 0.852446 0.811495 0.709906 0.066 Uiso 1 1 calc R U . . .
C4 C 0.5927(5) 0.7398(4) 0.9271(3) 0.0621(12) Uani 1 1 d . . . . .
H4A H 0.656046 0.688462 0.978297 0.093 Uiso 1 1 calc R U . . .
H4B H 0.519937 0.774979 0.955672 0.093 Uiso 1 1 calc R U . . .
H4C H 0.655008 0.797667 0.910043 0.093 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
Rh01 C11 1.845(3) . ?
Rh01 C10 2.006(3) . ?
Rh01 C7 2.021(3) . ?
Rh01 O1 2.0387(19) . ?
Rh01 Cl1 2.4779(8) . ?
Rh01 Cl1 2.5625(8) 3_666 ?
O1 C5 1.263(4) . ?
O3 C11 1.128(3) . ?
O2 C10 1.216(4) . ?
N1 C5 1.311(4) . ?
N1 C6 1.471(4) . ?
N1 C7 1.495(4) . ?
C7 C8 1.515(5) . ?
C7 H7 0.9800 . ?
C10 C9 1.484(5) . ?
C5 C2 1.545(4) . ?
C2 C4 1.527(5) . ?
C2 C3 1.528(5) . ?
C2 C1 1.536(5) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C8 C9 1.470(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 Rh01 C10 89.65(13) . . ?
C11 Rh01 C7 98.06(13) . . ?
C10 Rh01 C7 83.53(14) . . ?
C11 Rh01 O1 178.87(11) . . ?
C10 Rh01 O1 89.43(10) . . ?
C7 Rh01 O1 81.19(10) . . ?
C11 Rh01 Cl1 89.35(9) . . ?
C10 Rh01 Cl1 98.49(10) . . ?
C7 Rh01 Cl1 172.34(9) . . ?
O1 Rh01 Cl1 91.43(6) . . ?
C11 Rh01 Cl1 93.44(10) . 3_666 ?
C10 Rh01 Cl1 173.77(10) . 3_666 ?
C7 Rh01 Cl1 90.68(10) . 3_666 ?
O1 Rh01 Cl1 87.41(7) . 3_666 ?
Cl1 Rh01 Cl1 86.96(3) . 3_666 ?
Rh01 Cl1 Rh01 93.04(3) . 3_666 ?
C5 O1 Rh01 113.97(19) . . ?
C5 N1 C6 127.4(3) . . ?
C5 N1 C7 118.2(2) . . ?
C6 N1 C7 114.4(3) . . ?
N1 C7 C8 111.9(3) . . ?
N1 C7 Rh01 106.10(19) . . ?
C8 C7 Rh01 109.3(2) . . ?
N1 C7 H7 109.8 . . ?
C8 C7 H7 109.8 . . ?
Rh01 C7 H7 109.8 . . ?
O2 C10 C9 124.5(3) . . ?
O2 C10 Rh01 122.9(3) . . ?
C9 C10 Rh01 112.6(3) . . ?
O1 C5 N1 119.1(3) . . ?
O1 C5 C2 115.3(3) . . ?
N1 C5 C2 125.5(3) . . ?
O3 C11 Rh01 176.5(3) . . ?
C4 C2 C3 111.6(3) . . ?
C4 C2 C1 108.1(3) . . ?
C3 C2 C1 108.1(3) . . ?
C4 C2 C5 114.2(3) . . ?
C3 C2 C5 106.8(3) . . ?
C1 C2 C5 107.7(3) . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C9 C8 C7 109.3(3) . . ?
C9 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C8 C9 C10 111.3(3) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

_refine_diff_density_max         1.028
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.137

####################################################################### 
# 
# 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_20200629LI_SZZ_WYD_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2032398'
loop_
_audit_author_name
_audit_author_address
'Zhuangzhi Shi'
;Nanjing University
China
;
_audit_update_record             
;
2020-09-16 deposited with the CCDC.	2021-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H19 N O'
_chemical_formula_weight         217.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.9241(3)
_cell_length_b                   11.0168(4)
_cell_length_c                   24.6334(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2693.21(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    6679
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      44.81

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.331
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32086
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.122
_diffrn_reflns_theta_max         54.006
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4930
_reflns_number_gt                3108
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.999

_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1272P)²+0.0710P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0058(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1078 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(19)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         4930
_refine_ls_number_parameters     318
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.2009
_refine_ls_wR_factor_gt          0.1636
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.021
_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 0.6726(14) 0.2993(11) 0.5114(5) 0.102(4) Uani 0.533(9) 1 d . U P A 1
H1A H 0.707122 0.219320 0.500939 0.153 Uiso 0.533(9) 1 calc R U P A 1
H1B H 0.578825 0.307258 0.499436 0.153 Uiso 0.533(9) 1 calc R U P A 1
H1C H 0.727335 0.362656 0.494236 0.153 Uiso 0.533(9) 1 calc R U P A 1
C2 C 0.8206(12) 0.2778(10) 0.5922(5) 0.097(3) Uani 0.533(9) 1 d . U P A 1
H2A H 0.817127 0.288811 0.631632 0.145 Uiso 0.533(9) 1 calc R U P A 1
H2B H 0.842167 0.193039 0.583839 0.145 Uiso 0.533(9) 1 calc R U P A 1
H2C H 0.890267 0.330809 0.576864 0.145 Uiso 0.533(9) 1 calc R U P A 1
C3 C 0.5888(12) 0.2034(10) 0.5963(5) 0.099(3) Uani 0.533(9) 1 d . U P A 1
H3A H 0.593844 0.212780 0.635779 0.148 Uiso 0.533(9) 1 calc R U P A 1
H3B H 0.494637 0.209715 0.584581 0.148 Uiso 0.533(9) 1 calc R U P A 1
H3C H 0.624563 0.123729 0.585967 0.148 Uiso 0.533(9) 1 calc R U P A 1
C4 C 0.6789(5) 0.3115(7) 0.5666(3) 0.110(2) Uani 1 1 d . . . . .
C5 C 0.6254(4) 0.4365(5) 0.5848(2) 0.0879(16) Uani 1 1 d . . . . .
C6 C 0.6757(4) 0.6404(5) 0.61468(18) 0.0724(12) Uani 1 1 d . . . . .
H6A H 0.625541 0.688922 0.586933 0.087 Uiso 1 1 calc R U . . .
C7 C 0.7677(5) 0.7101(7) 0.6496(3) 0.118(2) Uani 1 1 d . . . . .
H7A H 0.775950 0.798315 0.642826 0.142 Uiso 1 1 calc R U . . .
H7B H 0.851870 0.669895 0.661554 0.142 Uiso 1 1 calc R U . . .
C8 C 0.6373(4) 0.6644(5) 0.67288(18) 0.0739(12) Uani 1 1 d . . . . .
H8A H 0.646625 0.592797 0.697517 0.089 Uiso 1 1 calc R U . . .
C9 C 0.5269(4) 0.7475(4) 0.68718(17) 0.0663(11) Uani 1 1 d . . . . .
C10 C 0.5176(5) 0.8645(5) 0.6665(2) 0.0906(15) Uani 1 1 d . . . . .
H10A H 0.584452 0.892965 0.641969 0.109 Uiso 1 1 calc R U . . .
C11 C 0.4120(7) 0.9404(5) 0.6810(3) 0.112(2) Uani 1 1 d . . . . .
H11A H 0.406053 1.019301 0.665642 0.134 Uiso 1 1 calc R U . . .
C12 C 0.3182(7) 0.9032(7) 0.7166(3) 0.111(2) Uani 1 1 d . . . . .
H12A H 0.247508 0.956585 0.726787 0.133 Uiso 1 1 calc R U . . .
C13 C 0.3237(5) 0.7902(7) 0.7380(2) 0.0987(18) Uani 1 1 d . . . . .
H13A H 0.256771 0.764472 0.763015 0.118 Uiso 1 1 calc R U . . .
C14 C 0.4276(5) 0.7114(5) 0.7233(2) 0.0807(13) Uani 1 1 d . . . . .
H14A H 0.430250 0.631953 0.738241 0.097 Uiso 1 1 calc R U . . .
C15 C 0.0404(7) 0.6963(9) 0.5278(3) 0.155(4) Uani 1 1 d . . . . .
H15A H 0.066391 0.757992 0.501067 0.233 Uiso 1 1 calc R U . . .
H15B H -0.015545 0.634533 0.510139 0.233 Uiso 1 1 calc R U . . .
H15C H -0.010708 0.734664 0.557164 0.233 Uiso 1 1 calc R U . . .
C16 C 0.2516(8) 0.7368(5) 0.5787(3) 0.114(2) Uani 1 1 d . . . . .
H16A H 0.332864 0.698906 0.593695 0.171 Uiso 1 1 calc R U . . .
H16B H 0.277369 0.798783 0.552156 0.171 Uiso 1 1 calc R U . . .
H16C H 0.199923 0.774555 0.608100 0.171 Uiso 1 1 calc R U . . .
C17 C 0.1637(4) 0.6383(4) 0.55043(18) 0.0672(11) Uani 1 1 d . . . . .
C18 C 0.2507(6) 0.5851(5) 0.5054(2) 0.0955(16) Uani 1 1 d . . . . .
H18A H 0.331061 0.547505 0.521227 0.143 Uiso 1 1 calc R U . . .
H18B H 0.199070 0.523763 0.485446 0.143 Uiso 1 1 calc R U . . .
H18C H 0.277995 0.649940 0.480425 0.143 Uiso 1 1 calc R U . . .
C19 C 0.1248(3) 0.5424(4) 0.59192(17) 0.0594(10) Uani 1 1 d . . . . .
C20 C 0.1960(4) 0.3929(4) 0.65691(18) 0.0646(10) Uani 1 1 d . . . . .
H20A H 0.118656 0.412291 0.681429 0.077 Uiso 1 1 calc R U . . .
C21 C 0.3093(5) 0.3278(5) 0.6829(2) 0.0849(14) Uani 1 1 d . . . . .
H21A H 0.302435 0.310318 0.722240 0.102 Uiso 1 1 calc R U . . .
H21B H 0.401567 0.345715 0.669870 0.102 Uiso 1 1 calc R U . . .
C22 C 0.2160(4) 0.2603(4) 0.64512(19) 0.0702(11) Uani 1 1 d . . . . .
H22A H 0.254525 0.241894 0.608518 0.084 Uiso 1 1 calc R U . . .
C23 C 0.1167(5) 0.1702(4) 0.66542(19) 0.0734(12) Uani 1 1 d . . . . .
C24 C 0.0578(6) 0.1786(4) 0.7164(2) 0.0859(14) Uani 1 1 d . . . . .
H24A H 0.083986 0.242509 0.740037 0.103 Uiso 1 1 calc R U . . .
C25 C -0.0386(7) 0.0958(5) 0.7336(2) 0.1017(18) Uani 1 1 d . . . . .
H25A H -0.078314 0.103669 0.768540 0.122 Uiso 1 1 calc R U . . .
C26 C -0.0755(7) 0.0040(5) 0.7004(3) 0.1047(18) Uani 1 1 d . . . . .
H26A H -0.140189 -0.053692 0.712294 0.126 Uiso 1 1 calc R U . . .
C27 C -0.0201(6) -0.0063(5) 0.6497(3) 0.1040(18) Uani 1 1 d . . . . .
H27A H -0.047854 -0.070100 0.626307 0.125 Uiso 1 1 calc R U . . .
C28 C 0.0758(6) 0.0756(4) 0.6324(2) 0.0889(15) Uani 1 1 d . . . . .
H28A H 0.114351 0.066853 0.597302 0.107 Uiso 1 1 calc R U . . .
N1 N 0.7158(3) 0.5222(4) 0.59798(17) 0.0823(11) Uani 1 1 d . . . . .
H1D H 0.802217 0.504776 0.596268 0.099 Uiso 1 1 calc R U . . .
N2 N 0.2239(3) 0.4819(3) 0.61632(14) 0.0645(9) Uani 1 1 d . . . . .
H2D H 0.308068 0.497020 0.607265 0.077 Uiso 1 1 calc R U . . .
O1 O 0.5046(3) 0.4585(4) 0.58690(18) 0.0991(12) Uani 1 1 d . . . . .
O2 O 0.0079(3) 0.5241(3) 0.60428(15) 0.0887(11) Uani 1 1 d . . . . .
C1' C 0.7969(18) 0.3537(17) 0.5169(7) 0.129(5) Uani 0.467(9) 1 d . U P A 2
H1'A H 0.750370 0.393823 0.486774 0.194 Uiso 0.467(9) 1 calc R U P A 2
H1'B H 0.862882 0.409527 0.532781 0.194 Uiso 0.467(9) 1 calc R U P A 2
H1'C H 0.843283 0.281110 0.503459 0.194 Uiso 0.467(9) 1 calc R U P A 2
C3' C 0.5664(16) 0.2680(14) 0.5268(6) 0.111(4) Uani 0.467(9) 1 d . U P A 2
H3'A H 0.548822 0.331489 0.499864 0.166 Uiso 0.467(9) 1 calc R U P A 2
H3'B H 0.595931 0.193861 0.508338 0.166 Uiso 0.467(9) 1 calc R U P A 2
H3'C H 0.483707 0.251335 0.547270 0.166 Uiso 0.467(9) 1 calc R U P A 2
C2' C 0.733(3) 0.258(2) 0.6077(8) 0.158(7) Uani 0.467(9) 1 d . U P A 2
H2'A H 0.767237 0.178341 0.596527 0.237 Uiso 0.467(9) 1 calc R U P A 2
H2'B H 0.807420 0.307355 0.621614 0.237 Uiso 0.467(9) 1 calc R U P A 2
H2'C H 0.665187 0.247268 0.636277 0.237 Uiso 0.467(9) 1 calc R U P A 2


_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 C4 1.369(13) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C4 1.585(13) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.659(13) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C2' 1.29(2) . ?
C4 C5 1.542(8) . ?
C4 C3' 1.562(15) . ?
C4 C1' 1.757(18) . ?
C5 O1 1.224(5) . ?
C5 N1 1.343(6) . ?
C6 N1 1.423(6) . ?
C6 C7 1.471(7) . ?
C6 C8 1.507(6) . ?
C6 H6A 1.0000 . ?
C7 C8 1.502(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.470(6) . ?
C8 H8A 1.0000 . ?
C9 C10 1.389(7) . ?
C9 C14 1.386(6) . ?
C10 C11 1.387(8) . ?
C10 H10A 0.9500 . ?
C11 C12 1.342(10) . ?
C11 H11A 0.9500 . ?
C12 C13 1.353(9) . ?
C12 H12A 0.9500 . ?
C13 C14 1.395(8) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 C17 1.489(7) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.557(8) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C19 1.520(6) . ?
C17 C18 1.524(7) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O2 1.216(4) . ?
C19 N2 1.331(5) . ?
C20 N2 1.427(5) . ?
C20 C21 1.480(6) . ?
C20 C22 1.503(6) . ?
C20 H20A 1.0000 . ?
C21 C22 1.509(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.485(7) . ?
C22 H22A 1.0000 . ?
C23 C28 1.383(7) . ?
C23 C24 1.389(7) . ?
C24 C25 1.387(8) . ?
C24 H24A 0.9500 . ?
C25 C26 1.352(8) . ?
C25 H25A 0.9500 . ?
C26 C27 1.370(8) . ?
C26 H26A 0.9500 . ?
C27 C28 1.378(7) . ?
C27 H27A 0.9500 . ?
C28 H28A 0.9500 . ?
N1 H1D 0.8800 . ?
N2 H2D 0.8800 . ?
C1' H1'A 0.9800 . ?
C1' H1'B 0.9800 . ?
C1' H1'C 0.9800 . ?
C3' H3'A 0.9800 . ?
C3' H3'B 0.9800 . ?
C3' H3'C 0.9800 . ?
C2' H2'A 0.9800 . ?
C2' H2'B 0.9800 . ?
C2' H2'C 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
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2' C4 C5 108.9(11) . . ?
C1 C4 C5 111.1(8) . . ?
C2' C4 C3' 130.5(14) . . ?
C5 C4 C3' 102.1(7) . . ?
C1 C4 C2 114.4(8) . . ?
C5 C4 C2 113.6(6) . . ?
C1 C4 C3 110.0(8) . . ?
C5 C4 C3 109.1(5) . . ?
C2 C4 C3 97.8(8) . . ?
C2' C4 C1' 113.0(13) . . ?
C5 C4 C1' 101.3(8) . . ?
C3' C4 C1' 96.9(9) . . ?
O1 C5 N1 120.3(5) . . ?
O1 C5 C4 121.8(5) . . ?
N1 C5 C4 117.9(4) . . ?
N1 C6 C7 118.2(4) . . ?
N1 C6 C8 120.4(4) . . ?
C7 C6 C8 60.6(4) . . ?
N1 C6 H6A 115.5 . . ?
C7 C6 H6A 115.5 . . ?
C8 C6 H6A 115.5 . . ?
C6 C7 C8 60.9(3) . . ?
C6 C7 H7A 117.7 . . ?
C8 C7 H7A 117.7 . . ?
C6 C7 H7B 117.7 . . ?
C8 C7 H7B 117.7 . . ?
H7A C7 H7B 114.8 . . ?
C9 C8 C7 121.7(5) . . ?
C9 C8 C6 121.7(4) . . ?
C7 C8 C6 58.5(3) . . ?
C9 C8 H8A 114.5 . . ?
C7 C8 H8A 114.5 . . ?
C6 C8 H8A 114.5 . . ?
C10 C9 C14 117.0(5) . . ?
C10 C9 C8 122.6(4) . . ?
C14 C9 C8 120.3(4) . . ?
C9 C10 C11 121.0(6) . . ?
C9 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 . . ?
C12 C11 C10 120.5(6) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C11 C12 C13 120.5(6) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C12 C13 C14 120.1(6) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C9 C14 C13 120.9(5) . . ?
C9 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C17 C15 H15A 109.5 . . ?
C17 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C17 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 C19 110.0(4) . . ?
C15 C17 C18 111.0(5) . . ?
C19 C17 C18 111.5(4) . . ?
C15 C17 C16 109.2(6) . . ?
C19 C17 C16 109.0(4) . . ?
C18 C17 C16 106.0(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C19 N2 120.6(4) . . ?
O2 C19 C17 121.7(3) . . ?
N2 C19 C17 117.7(3) . . ?
N2 C20 C21 119.3(4) . . ?
N2 C20 C22 120.4(4) . . ?
C21 C20 C22 60.8(3) . . ?
N2 C20 H20A 115.2 . . ?
C21 C20 H20A 115.2 . . ?
C22 C20 H20A 115.2 . . ?
C20 C21 C22 60.4(3) . . ?
C20 C21 H21A 117.7 . . ?
C22 C21 H21A 117.7 . . ?
C20 C21 H21B 117.7 . . ?
C22 C21 H21B 117.7 . . ?
H21A C21 H21B 114.9 . . ?
C23 C22 C20 119.8(4) . . ?
C23 C22 C21 121.9(4) . . ?
C20 C22 C21 58.8(3) . . ?
C23 C22 H22A 114.9 . . ?
C20 C22 H22A 114.9 . . ?
C21 C22 H22A 114.9 . . ?
C28 C23 C24 117.3(5) . . ?
C28 C23 C22 120.0(4) . . ?
C24 C23 C22 122.6(4) . . ?
C25 C24 C23 121.5(5) . . ?
C25 C24 H24A 119.2 . . ?
C23 C24 H24A 119.2 . . ?
C26 C25 C24 119.6(5) . . ?
C26 C25 H25A 120.2 . . ?
C24 C25 H25A 120.2 . . ?
C25 C26 C27 120.3(6) . . ?
C25 C26 H26A 119.8 . . ?
C27 C26 H26A 119.8 . . ?
C26 C27 C28 120.3(5) . . ?
C26 C27 H27A 119.8 . . ?
C28 C27 H27A 119.8 . . ?
C27 C28 C23 120.9(5) . . ?
C27 C28 H28A 119.5 . . ?
C23 C28 H28A 119.5 . . ?
C5 N1 C6 121.8(4) . . ?
C5 N1 H1D 119.1 . . ?
C6 N1 H1D 119.1 . . ?
C19 N2 C20 121.1(3) . . ?
C19 N2 H2D 119.5 . . ?
C20 N2 H2D 119.5 . . ?
C4 C1' H1'A 109.5 . . ?
C4 C1' H1'B 109.5 . . ?
H1'A C1' H1'B 109.5 . . ?
C4 C1' H1'C 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?
C4 C3' H3'A 109.5 . . ?
C4 C3' H3'B 109.5 . . ?
H3'A C3' H3'B 109.5 . . ?
C4 C3' H3'C 109.5 . . ?
H3'A C3' H3'C 109.5 . . ?
H3'B C3' H3'C 109.5 . . ?
C4 C2' H2'A 109.5 . . ?
C4 C2' H2'B 109.5 . . ?
H2'A C2' H2'B 109.5 . . ?
C4 C2' H2'C 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 109.5 . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.047

