# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

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

data_170301_myj20170227_1
_database_code_depnum_ccdc_archive 'CCDC 1853333'
loop_
_audit_author_name
_audit_author_address
'Yang-Jie Mao'
;zhejiang university of technology
China
;
_audit_update_record             
;
2019-08-23 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;
_audit_creation_date             2017-03-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C14 H12 N4 O3 Pd), C H2 Cl2'
_chemical_formula_sum            'C29 H26 Cl2 N8 O6 Pd2'
_chemical_formula_weight         866.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 pd1'
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'
Pd Pd -0.9988 1.0072 '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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   23.9255(13)
_cell_length_b                   7.4483(7)
_cell_length_c                   18.7126(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3334.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3923
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3451
_cell_measurement_theta_min      2.8586
_shelx_estimated_absorpt_T_max   0.682
_shelx_estimated_absorpt_T_min   0.576
_exptl_absorpt_coefficient_mu    1.293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19430
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.864
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -62.00   36.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8433  -38.0000  -60.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega  -15.00   76.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8433   38.0000  120.0000 91

#__ type_ start__ end____ width___ exp.time_
  3 omega  -70.00   21.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.5621  -77.0000 -180.0000 91
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0037065000
_diffrn_orient_matrix_UB_12      -0.0157815000
_diffrn_orient_matrix_UB_13      0.0370666000
_diffrn_orient_matrix_UB_21      0.0105932000
_diffrn_orient_matrix_UB_22      -0.0883093000
_diffrn_orient_matrix_UB_23      -0.0042774000
_diffrn_orient_matrix_UB_31      0.0274326000
_diffrn_orient_matrix_UB_32      0.0319734000
_diffrn_orient_matrix_UB_33      0.0067229000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2195
_reflns_number_total             3047
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         2.500
_refine_diff_density_min         -1.623
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3047
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0652P)²+15.8201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1480
_refine_ls_wR_factor_ref         0.1668
_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. Others
 Fixed Sof: H15A(0.5) H15B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.71160(2) 0.86742(9) 0.03856(3) 0.0575(3) Uani 1 1 d . . . . .
O1 O 0.6453(2) 0.9930(8) 0.1050(3) 0.0691(14) Uani 1 1 d . . . . .
O2 O 0.5996(2) 0.9553(9) 0.2018(3) 0.0818(17) Uani 1 1 d . . . . .
O3 O 0.6476(3) 0.7393(10) 0.1596(4) 0.108(2) Uani 1 1 d . . . . .
N1 N 0.6927(2) 0.8040(9) -0.1091(3) 0.0592(15) Uani 1 1 d . . . . .
N2 N 0.6667(2) 0.8247(9) -0.0514(3) 0.0567(15) Uani 1 1 d . . . . .
N3 N 0.6303(2) 0.8956(9) 0.1562(3) 0.0607(16) Uani 1 1 d . . . . .
N4 N 0.7659(3) 0.8829(9) 0.1204(3) 0.0669(17) Uani 1 1 d . . . . .
C1 C 0.7706(3) 0.8232(10) -0.0306(4) 0.0525(16) Uani 1 1 d . . . . .
C2 C 0.8282(3) 0.8257(12) -0.0214(4) 0.069(2) Uani 1 1 d . . . . .
H2 H 0.843498 0.838530 0.023974 0.083 Uiso 1 1 calc R . . . .
C3 C 0.8626(3) 0.8089(13) -0.0806(4) 0.074(2) Uani 1 1 d . . . . .
H3 H 0.901175 0.811668 -0.074417 0.089 Uiso 1 1 calc R . . . .
C4 C 0.8411(3) 0.7882(12) -0.1480(4) 0.071(2) Uani 1 1 d . . . . .
H4 H 0.864970 0.775673 -0.186878 0.086 Uiso 1 1 calc R . . . .
C5 C 0.7852(3) 0.7859(12) -0.1579(4) 0.064(2) Uani 1 1 d . . . . .
H5 H 0.770357 0.771765 -0.203553 0.077 Uiso 1 1 calc R . . . .
C6 C 0.7501(3) 0.8050(10) -0.0994(4) 0.0547(16) Uani 1 1 d . . . . .
C7 C 0.6071(3) 0.8230(10) -0.0579(4) 0.0583(18) Uani 1 1 d . . . . .
C8 C 0.5810(3) 0.8858(10) -0.1180(5) 0.067(2) Uani 1 1 d . . . . .
H8 H 0.601862 0.930385 -0.155999 0.080 Uiso 1 1 calc R . . . .
C9 C 0.5243(4) 0.8825(12) -0.1217(6) 0.082(3) Uani 1 1 d . . . . .
H9 H 0.506439 0.926729 -0.162162 0.099 Uiso 1 1 calc R . . . .
C10 C 0.4932(3) 0.8148(13) -0.0667(6) 0.084(3) Uani 1 1 d . . . . .
H10 H 0.454350 0.814674 -0.069403 0.100 Uiso 1 1 calc R . . . .
C11 C 0.5191(3) 0.7484(13) -0.0084(5) 0.080(3) Uani 1 1 d . . . . .
H11 H 0.497830 0.698622 0.028175 0.097 Uiso 1 1 calc R . . . .
C12 C 0.5765(3) 0.7530(12) -0.0022(4) 0.065(2) Uani 1 1 d . . . . .
H12 H 0.594167 0.709802 0.038660 0.079 Uiso 1 1 calc R . . . .
C13 C 0.7996(3) 0.8718(10) 0.1622(4) 0.0575(18) Uani 1 1 d . . . . .
C14 C 0.8443(4) 0.8585(12) 0.2145(4) 0.075(2) Uani 1 1 d . . . . .
H14A H 0.866719 0.754647 0.204433 0.112 Uiso 1 1 calc GR . . . .
H14B H 0.828519 0.847777 0.261519 0.112 Uiso 1 1 calc GR . . . .
H14C H 0.867168 0.964200 0.212234 0.112 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.49351(19) 0.5549(7) 0.17600(18) 0.1660(17) Uani 1 1 d . . . . .
C15 C 0.500000 0.6835(17) 0.250000 0.083(4) Uani 1 2 d S T P . .
H15A H 0.532601 0.760002 0.245325 0.100 Uiso 0.5 1 calc R . . . .
H15B H 0.467397 0.759994 0.254676 0.100 Uiso 0.5 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
Pd1 O1 2.221(5) . ?
Pd1 N2 2.022(6) . ?
Pd1 N4 2.011(7) . ?
Pd1 C1 1.943(6) . ?
O1 N3 1.253(8) . ?
O2 N3 1.212(8) . ?
O3 N3 1.238(9) . ?
N1 N2 1.255(8) . ?
N1 C6 1.384(9) . ?
N2 C7 1.433(9) . ?
N4 C13 1.127(9) . ?
C1 C2 1.388(10) . ?
C1 C6 1.386(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.351(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(9) . ?
C7 C8 1.370(11) . ?
C7 C12 1.375(11) . ?
C8 H8 0.9300 . ?
C8 C9 1.358(11) . ?
C9 H9 0.9300 . ?
C9 C10 1.367(13) . ?
C10 H10 0.9300 . ?
C10 C11 1.347(13) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.453(11) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
Cl1 C15 1.691(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

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
N2 Pd1 O1 98.8(2) . . ?
N4 Pd1 O1 90.6(2) . . ?
N4 Pd1 N2 170.3(2) . . ?
C1 Pd1 O1 164.3(3) . . ?
C1 Pd1 N2 78.7(3) . . ?
C1 Pd1 N4 92.7(3) . . ?
N3 O1 Pd1 112.9(5) . . ?
N2 N1 C6 112.2(6) . . ?
N1 N2 Pd1 118.2(5) . . ?
N1 N2 C7 114.8(6) . . ?
C7 N2 Pd1 126.9(5) . . ?
O2 N3 O1 120.0(7) . . ?
O2 N3 O3 120.7(7) . . ?
O3 N3 O1 119.3(7) . . ?
C13 N4 Pd1 170.6(7) . . ?
C2 C1 Pd1 129.5(6) . . ?
C6 C1 Pd1 112.2(5) . . ?
C6 C1 C2 117.9(6) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.3(7) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(7) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(7) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.3(7) . . ?
C6 C5 H5 120.3 . . ?
N1 C6 C1 118.3(6) . . ?
N1 C6 C5 119.8(6) . . ?
C1 C6 C5 121.9(7) . . ?
C8 C7 N2 121.4(7) . . ?
C8 C7 C12 120.7(7) . . ?
C12 C7 N2 117.9(7) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.4(8) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.9(9) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(8) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.2(9) . . ?
C12 C11 H11 119.4 . . ?
C7 C12 C11 118.3(8) . . ?
C7 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
N4 C13 C14 178.3(8) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Cl1 C15 Cl1 111.0(8) 4_655 . ?
Cl1 C15 H15A 109.4 . . ?
Cl1 C15 H15A 109.4 4_655 . ?
Cl1 C15 H15B 109.4 4_655 . ?
Cl1 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?

_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_mjr17026_0m
_database_code_depnum_ccdc_archive 'CCDC 1949005'
loop_
_audit_author_name
_audit_author_address
'Yang-Jie Mao'
;zhejiang university of technology
China
;
_audit_update_record             
;
2019-08-23 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;
_audit_creation_date             2017-09-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 N4 O2 Pd, H2 O'
_chemical_formula_sum            'C14 H14 N4 O3 Pd'
_chemical_formula_weight         392.69
_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 0.0150 0.0070 '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 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0410 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.0660 3.1310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   33.8026(6)
_cell_length_b                   4.69190(10)
_cell_length_c                   20.2989(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.1400(10)
_cell_angle_gamma                90
_cell_volume                     3158.71(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      60.648
_cell_measurement_theta_min      4.878
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.429
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.4874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1598 before and 0.0663 after correction. The Ratio of minimum to maximum transmission is 0.6482. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19305
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.617
_diffrn_reflns_theta_min         4.876
_diffrn_ambient_temperature      302.25
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2721
_reflns_number_total             3586
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.538
_refine_diff_density_min         -1.074
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3586
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0345P)²+3.5513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0819
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.63818(2) 0.74855(4) 0.46456(2) 0.04144(9) Uani 1 1 d . . . . .
O1 O 0.67212(10) 0.7116(9) 0.34665(14) 0.1204(16) Uani 1 1 d . . . . .
O2 O 0.70894(8) 0.9286(7) 0.42396(16) 0.0971(10) Uani 1 1 d . . . . .
N1 N 0.59445(7) 0.7183(5) 0.52079(12) 0.0419(5) Uani 1 1 d . . . . .
N2 N 0.56027(7) 0.8286(6) 0.49818(12) 0.0461(5) Uani 1 1 d . . . . .
N3 N 0.67982(7) 0.4597(6) 0.51986(12) 0.0524(6) Uani 1 1 d . . . . .
N4 N 0.67696(8) 0.8085(6) 0.40173(14) 0.0558(7) Uani 1 1 d . . . . .
C1 C 0.59627(8) 0.9977(6) 0.41398(13) 0.0425(6) Uani 1 1 d . . . . .
C2 C 0.59576(10) 1.1705(7) 0.35817(15) 0.0529(7) Uani 1 1 d . . . . .
H2 H 0.618841 1.187864 0.339893 0.064 Uiso 1 1 calc R . . . .
C3 C 0.56107(11) 1.3171(8) 0.32960(18) 0.0657(9) Uani 1 1 d . . . . .
H3 H 0.561292 1.431878 0.292315 0.079 Uiso 1 1 calc R . . . .
C4 C 0.52625(12) 1.2967(8) 0.35516(19) 0.0667(9) Uani 1 1 d . . . . .
H4 H 0.503188 1.394340 0.334701 0.080 Uiso 1 1 calc R . . . .
C5 C 0.52567(9) 1.1318(8) 0.41101(15) 0.0551(7) Uani 1 1 d . . . . .
H5 H 0.502548 1.119401 0.429334 0.066 Uiso 1 1 calc R . . . .
C6 C 0.56042(8) 0.9841(6) 0.43940(13) 0.0442(6) Uani 1 1 d . . . . .
C7 C 0.59782(8) 0.5692(6) 0.58323(13) 0.0455(6) Uani 1 1 d . . . . .
C8 C 0.56713(9) 0.3951(7) 0.59572(15) 0.0529(7) Uani 1 1 d . . . . .
H8 H 0.543563 0.373564 0.563828 0.063 Uiso 1 1 calc R . . . .
C9 C 0.57211(13) 0.2535(7) 0.65652(19) 0.0656(9) Uani 1 1 d . . . . .
H9 H 0.551940 0.132921 0.665394 0.079 Uiso 1 1 calc R . . . .
C10 C 0.60684(13) 0.2902(8) 0.70401(18) 0.0714(11) Uani 1 1 d . . . . .
H10 H 0.609917 0.193968 0.744743 0.086 Uiso 1 1 calc R . . . .
C11 C 0.63672(11) 0.4662(9) 0.69187(16) 0.0707(10) Uani 1 1 d . . . . .
H11 H 0.659815 0.493026 0.724540 0.085 Uiso 1 1 calc R . . . .
C12 C 0.63253(9) 0.6047(8) 0.63067(15) 0.0601(8) Uani 1 1 d . . . . .
H12 H 0.653090 0.721330 0.621653 0.072 Uiso 1 1 calc R . . . .
C13 C 0.70111(9) 0.3019(7) 0.54936(16) 0.0491(7) Uani 1 1 d . . . . .
C14 C 0.72840(10) 0.0997(8) 0.58879(18) 0.0683(9) Uani 1 1 d . . . . .
H14A H 0.730371 -0.067800 0.562474 0.102 Uiso 1 1 calc GR . . . .
H14B H 0.718297 0.048495 0.628251 0.102 Uiso 1 1 calc GR . . . .
H14C H 0.754577 0.184814 0.601742 0.102 Uiso 1 1 calc GR . . . .
O3 O 0.74172(13) 0.9130(7) 0.27905(19) 0.1193(13) Uani 1 1 d . . . . .
H3A H 0.722172 0.885793 0.299132 0.179 Uiso 1 1 d G . . . .
H3B H 0.748182 0.756008 0.263101 0.179 Uiso 1 1 d G . . . .


_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
Pd1 N1 2.040(2) . ?
Pd1 N3 2.114(3) . ?
Pd1 N4 2.017(3) . ?
Pd1 C1 1.966(3) . ?
O1 N4 1.189(4) . ?
O2 N4 1.225(4) . ?
N1 N2 1.268(3) . ?
N1 C7 1.433(3) . ?
N2 C6 1.400(3) . ?
N3 C13 1.122(4) . ?
C1 C2 1.390(4) . ?
C1 C6 1.407(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(4) . ?
C7 C8 1.382(4) . ?
C7 C12 1.377(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.383(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.363(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.451(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O3 H3A 0.8504 . ?
O3 H3B 0.8498 . ?

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 Pd1 N3 97.96(9) . . ?
N4 Pd1 N1 173.30(10) . . ?
N4 Pd1 N3 88.73(10) . . ?
C1 Pd1 N1 78.86(10) . . ?
C1 Pd1 N3 175.79(10) . . ?
C1 Pd1 N4 94.44(11) . . ?
N2 N1 Pd1 118.50(18) . . ?
N2 N1 C7 115.5(2) . . ?
C7 N1 Pd1 125.92(18) . . ?
N1 N2 C6 111.6(2) . . ?
C13 N3 Pd1 178.2(3) . . ?
O1 N4 Pd1 123.6(2) . . ?
O1 N4 O2 118.3(3) . . ?
O2 N4 Pd1 117.8(2) . . ?
C2 C1 Pd1 131.8(2) . . ?
C2 C1 C6 116.7(3) . . ?
C6 C1 Pd1 111.47(19) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.5(3) . . ?
C6 C5 H5 120.8 . . ?
N2 C6 C1 118.8(2) . . ?
C5 C6 N2 118.1(2) . . ?
C5 C6 C1 123.0(3) . . ?
C8 C7 N1 121.1(3) . . ?
C12 C7 N1 118.1(3) . . ?
C12 C7 C8 120.8(3) . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C9 118.8(3) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.7(3) . . ?
C12 C11 H11 120.2 . . ?
C7 C12 C11 119.8(3) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
N3 C13 C14 178.8(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H3A O3 H3B 109.5 . . ?

_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_1905055737_0m
_database_code_depnum_ccdc_archive 'CCDC 1949006'
loop_
_audit_author_name
_audit_author_address
'Yang-Jie Mao'
;zhejiang university of technology
China
;
_audit_update_record             
;
2019-08-23 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;
_audit_creation_date             2019-05-07
_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         'C24 H28 F N O2'
_chemical_formula_sum            'C24 H28 F N O2'
_chemical_formula_weight         381.47
_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 0.0148 0.0070 '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'
F F 0.0599 0.0411 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   7.3870(2)
_cell_length_b                   9.3722(2)
_cell_length_c                   15.5339(4)
_cell_angle_alpha                73.1920(10)
_cell_angle_beta                 85.0490(10)
_cell_angle_gamma                75.3100(10)
_cell_volume                     995.76(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.90
_cell_measurement_theta_min      5.18
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.446
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1229 before and 0.0473 after correction. The Ratio of minimum to maximum transmission is 0.8660. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18763
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.900
_diffrn_reflns_theta_min         5.176
_diffrn_ambient_temperature      169.97
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.949
_reflns_Friedel_fraction_full    0.938
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                7113
_reflns_number_total             7233
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 3360 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     521
_refine_ls_number_reflns         7233
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0634P)²+0.1523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1003
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Rotating group:
 N1A(H1AA,H1AB)
2.b Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C10(H10), C15(H15), C4A(H4A), C5A(H5A), C10A(H10A), C15A(H15A)
2.c Secondary CH2 refined with riding coordinates:
 C1(H1C,H1D), C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C16(H16A,H16B), C17(H17A,
 H17B), C1A(H1AC,H1AD), C2A(H2AB,H2AC), C6A(H6AA,H6AB), C7A(H7AA,H7AB),
 C16A(H16C,H16D), C17A(H17C,H17D)
2.d Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C20(H20), C21(H21), C24(H24), C11A(H11A),
 C12A(H12A), C14A(H14A), C20A(H20A), C21A(H21A), C24A(H24A)
2.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C18A(H18D,H18E,H18F)
2.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.0884(2) 0.4758(2) 0.07971(12) 0.0476(4) Uani 1 1 d . . . . .
O1 O 0.6978(3) 0.4144(3) 0.18016(14) 0.0487(5) Uani 1 1 d . . . . .
O2 O 1.0906(3) 0.0804(2) 0.89057(12) 0.0426(4) Uani 1 1 d . . . . .
H2 H 0.980301 0.073564 0.887533 0.064 Uiso 1 1 calc GR . . . .
N1 N 0.0375(3) 0.7853(3) 0.00931(15) 0.0406(5) Uani 1 1 d . . . . .
C1 C 0.7861(3) 0.3048(3) 0.60987(17) 0.0342(5) Uani 1 1 d . . . . .
H1C H 0.747015 0.211722 0.608983 0.041 Uiso 1 1 calc R . . . .
H1D H 0.674490 0.392057 0.597597 0.041 Uiso 1 1 calc R . . . .
C2 C 0.8590(3) 0.2818(3) 0.70422(16) 0.0331(5) Uani 1 1 d . . . . .
H2A H 0.880971 0.379571 0.708308 0.040 Uiso 1 1 calc R . . . .
H2B H 0.763151 0.253011 0.750066 0.040 Uiso 1 1 calc R . . . .
C3 C 1.0408(3) 0.1568(3) 0.72359(16) 0.0286(5) Uani 1 1 d . . . . .
C4 C 1.1830(3) 0.1970(3) 0.64786(17) 0.0303(5) Uani 1 1 d . . . . .
H4 H 1.199083 0.300247 0.646798 0.036 Uiso 1 1 calc R . . . .
C5 C 1.1176(3) 0.2123(3) 0.55489(16) 0.0280(5) Uani 1 1 d . . . . .
H5 H 1.093820 0.112095 0.554525 0.034 Uiso 1 1 calc R . . . .
C6 C 1.2600(3) 0.2535(3) 0.48117(17) 0.0335(5) Uani 1 1 d . . . . .
H6A H 1.272830 0.358586 0.475063 0.040 Uiso 1 1 calc R . . . .
H6B H 1.383526 0.181511 0.497286 0.040 Uiso 1 1 calc R . . . .
C7 C 1.1980(3) 0.2450(3) 0.39274(17) 0.0332(5) Uani 1 1 d . . . . .
H7A H 1.271661 0.298224 0.343226 0.040 Uiso 1 1 calc R . . . .
H7B H 1.225875 0.136010 0.392665 0.040 Uiso 1 1 calc R . . . .
C8 C 0.9921(3) 0.3157(3) 0.37478(16) 0.0276(5) Uani 1 1 d . . . . .
C9 C 0.8651(3) 0.3587(3) 0.44094(16) 0.0283(5) Uani 1 1 d . . . . .
C10 C 0.9328(3) 0.3361(3) 0.53513(15) 0.0272(5) Uani 1 1 d . . . . .
H10 H 0.961426 0.434802 0.535185 0.033 Uiso 1 1 calc R . . . .
C11 C 0.6791(3) 0.4270(3) 0.41578(16) 0.0326(5) Uani 1 1 d . . . . .
H11 H 0.592130 0.458627 0.459325 0.039 Uiso 1 1 calc R . . . .
C12 C 0.6158(3) 0.4508(3) 0.33005(18) 0.0359(5) Uani 1 1 d . . . . .
H12 H 0.488332 0.497831 0.315117 0.043 Uiso 1 1 calc R . . . .
C13 C 0.7433(3) 0.4043(3) 0.26659(17) 0.0332(5) Uani 1 1 d . . . . .
C14 C 0.9292(3) 0.3391(3) 0.28886(17) 0.0320(5) Uani 1 1 d . . . . .
H14 H 1.015616 0.309762 0.244514 0.038 Uiso 1 1 calc R . . . .
C15 C 1.1546(4) 0.1506(3) 0.80346(17) 0.0339(5) Uani 1 1 d . . . . .
H15 H 1.158986 0.257661 0.800684 0.041 Uiso 1 1 calc R . . . .
C16 C 1.3541(4) 0.0611(4) 0.7851(2) 0.0438(6) Uani 1 1 d . . . . .
H16A H 1.449557 0.102932 0.803926 0.053 Uiso 1 1 calc R . . . .
H16B H 1.373774 -0.048987 0.818281 0.053 Uiso 1 1 calc R . . . .
C17 C 1.3670(4) 0.0817(3) 0.68263(19) 0.0403(6) Uani 1 1 d . . . . .
H17A H 1.476184 0.122927 0.655795 0.048 Uiso 1 1 calc R . . . .
H17B H 1.377043 -0.016816 0.668931 0.048 Uiso 1 1 calc R . . . .
C18 C 1.0017(4) -0.0004(3) 0.73552(19) 0.0405(6) Uani 1 1 d . . . . .
H18A H 0.945217 -0.000674 0.680765 0.061 Uiso 1 1 calc GR . . . .
H18B H 0.915401 -0.021689 0.786573 0.061 Uiso 1 1 calc GR . . . .
H18C H 1.119251 -0.079610 0.746884 0.061 Uiso 1 1 calc GR . . . .
C19 C 0.5299(4) 0.5109(3) 0.14361(17) 0.0364(5) Uani 1 1 d . . . . .
C20 C 0.5119(4) 0.6669(3) 0.10771(19) 0.0411(6) Uani 1 1 d . . . . .
H20 H 0.610120 0.711713 0.114018 0.049 Uiso 1 1 calc R . . . .
C21 C 0.3501(4) 0.7585(3) 0.06230(18) 0.0391(6) Uani 1 1 d . . . . .
H21 H 0.338664 0.865724 0.038175 0.047 Uiso 1 1 calc R . . . .
C22 C 0.2057(3) 0.6957(3) 0.05177(15) 0.0330(5) Uani 1 1 d . . . . .
C23 C 0.2293(4) 0.5394(3) 0.08990(16) 0.0330(5) Uani 1 1 d . . . . .
C24 C 0.3862(4) 0.4452(3) 0.13550(16) 0.0351(5) Uani 1 1 d . . . . .
H24 H 0.395926 0.338419 0.160702 0.042 Uiso 1 1 calc R . . . .
F1A F 0.7593(2) 0.60003(19) 0.92893(11) 0.0441(4) Uani 1 1 d . . . . .
O1A O 0.1940(2) 0.5100(2) 0.85316(11) 0.0371(4) Uani 1 1 d . . . . .
O2A O -0.0278(3) 0.9898(2) 0.12130(12) 0.0381(4) Uani 1 1 d . . . . .
N1A N 0.9175(3) 0.2885(3) 0.99100(14) 0.0342(4) Uani 1 1 d . . . . .
H1AA H 0.924095 0.211049 1.040045 0.041 Uiso 1 1 d GR . . . .
H1AB H 0.990135 0.256954 0.948658 0.041 Uiso 1 1 d GR . . . .
C1A C 0.2068(3) 0.7709(3) 0.41284(16) 0.0374(6) Uani 1 1 d . . . . .
H1AC H 0.221152 0.662222 0.414581 0.045 Uiso 1 1 calc R . . . .
H1AD H 0.327593 0.781438 0.430239 0.045 Uiso 1 1 calc R . . . .
C2A C 0.1607(3) 0.8727(3) 0.31624(16) 0.0354(5) Uani 1 1 d . . . . .
H2AB H 0.163915 0.979449 0.312185 0.042 Uiso 1 1 calc R . . . .
H2AC H 0.256576 0.835322 0.274089 0.042 Uiso 1 1 calc R . . . .
C3A C -0.0319(3) 0.8707(2) 0.28917(15) 0.0259(4) Uani 1 1 d . . . . .
C4A C -0.1780(3) 0.9176(3) 0.35849(15) 0.0285(5) Uani 1 1 d . . . . .
H4A H -0.169779 1.021873 0.359689 0.034 Uiso 1 1 calc R . . . .
C5A C -0.1414(3) 0.8142(3) 0.45374(15) 0.0257(4) Uani 1 1 d . . . . .
H5A H -0.143779 0.707389 0.454980 0.031 Uiso 1 1 calc R . . . .
C6A C -0.2854(3) 0.8672(3) 0.52166(17) 0.0343(5) Uani 1 1 d . . . . .
H6AA H -0.276394 0.969188 0.524727 0.041 Uiso 1 1 calc R . . . .
H6AB H -0.412916 0.877209 0.501750 0.041 Uiso 1 1 calc R . . . .
C7A C -0.2524(3) 0.7532(3) 0.61435(16) 0.0343(5) Uani 1 1 d . . . . .
H7AA H -0.327344 0.800770 0.659271 0.041 Uiso 1 1 calc R . . . .
H7AB H -0.297482 0.661901 0.615147 0.041 Uiso 1 1 calc R . . . .
C8A C -0.0494(3) 0.7018(3) 0.64162(16) 0.0259(4) Uani 1 1 d . . . . .
C9A C 0.0970(3) 0.7198(3) 0.57868(15) 0.0263(5) Uani 1 1 d . . . . .
C10A C 0.0542(3) 0.8137(3) 0.48121(15) 0.0276(5) Uani 1 1 d . . . . .
H10A H 0.049528 0.922315 0.478968 0.033 Uiso 1 1 calc R . . . .
C11A C 0.2788(3) 0.6585(3) 0.60972(16) 0.0324(5) Uani 1 1 d . . . . .
H11A H 0.379306 0.666748 0.567545 0.039 Uiso 1 1 calc R . . . .
C12A C 0.3204(3) 0.5855(3) 0.69977(17) 0.0343(5) Uani 1 1 d . . . . .
H12A H 0.446437 0.543330 0.718714 0.041 Uiso 1 1 calc R . . . .
C13A C 0.1736(3) 0.5759(3) 0.76100(15) 0.0287(5) Uani 1 1 d . . . . .
C14A C -0.0088(3) 0.6309(3) 0.73219(15) 0.0276(5) Uani 1 1 d . . . . .
H14A H -0.108396 0.620209 0.774718 0.033 Uiso 1 1 calc R . . . .
C15A C -0.1146(4) 0.9981(3) 0.20575(16) 0.0332(5) Uani 1 1 d . . . . .
H15A H -0.104713 1.097276 0.214734 0.040 Uiso 1 1 calc R . . . .
C16A C -0.3248(4) 0.9985(4) 0.21263(19) 0.0464(7) Uani 1 1 d . . . . .
H16C H -0.350855 0.929942 0.179737 0.056 Uiso 1 1 calc R . . . .
H16D H -0.402421 1.103419 0.187383 0.056 Uiso 1 1 calc R . . . .
C17A C -0.3657(4) 0.9393(4) 0.31447(19) 0.0439(7) Uani 1 1 d . . . . .
H17C H -0.465854 1.015227 0.335071 0.053 Uiso 1 1 calc R . . . .
H17D H -0.403570 0.840909 0.328481 0.053 Uiso 1 1 calc R . . . .
C18A C -0.0270(4) 0.7130(3) 0.27722(17) 0.0357(5) Uani 1 1 d . . . . .
H18D H 0.015561 0.633159 0.332887 0.054 Uiso 1 1 calc GR . . . .
H18E H 0.059237 0.694911 0.227804 0.054 Uiso 1 1 calc GR . . . .
H18F H -0.152803 0.710270 0.263329 0.054 Uiso 1 1 calc GR . . . .
C19A C 0.3745(3) 0.4568(3) 0.88791(15) 0.0314(5) Uani 1 1 d . . . . .
C20A C 0.4413(4) 0.3011(3) 0.92507(16) 0.0335(5) Uani 1 1 d . . . . .
H20A H 0.366209 0.232189 0.925740 0.040 Uiso 1 1 calc R . . . .
C21A C 0.6189(4) 0.2460(3) 0.96145(16) 0.0330(5) Uani 1 1 d . . . . .
H21A H 0.664225 0.138746 0.987150 0.040 Uiso 1 1 calc R . . . .
C22A C 0.7323(3) 0.3443(3) 0.96117(15) 0.0290(5) Uani 1 1 d . . . . .
C23A C 0.6554(3) 0.5006(3) 0.92597(15) 0.0289(5) Uani 1 1 d . . . . .
C24A C 0.4811(3) 0.5590(3) 0.88890(15) 0.0315(5) Uani 1 1 d . . . . .
H24A H 0.434346 0.666449 0.864533 0.038 Uiso 1 1 calc R . . . .
H1A H 0.055(5) 0.873(4) -0.038(2) 0.043(8) Uiso 1 1 d . . . . .
H1B H -0.034(5) 0.729(4) -0.010(2) 0.051(9) Uiso 1 1 d . . . . .
H2AA H -0.047(6) 0.901(5) 0.105(3) 0.066(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C23 1.364(3) . ?
O1 C13 1.383(3) . ?
O1 C19 1.391(3) . ?
O2 H2 0.8400 . ?
O2 C15 1.421(3) . ?
N1 C22 1.405(3) . ?
N1 H1A 0.96(4) . ?
N1 H1B 0.95(4) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C1 C2 1.543(3) . ?
C1 C10 1.535(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.528(3) . ?
C3 C4 1.536(3) . ?
C3 C15 1.537(3) . ?
C3 C18 1.529(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.518(3) . ?
C4 C17 1.533(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.519(3) . ?
C5 C10 1.539(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.514(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.512(3) . ?
C8 C9 1.407(3) . ?
C8 C14 1.390(3) . ?
C9 C10 1.526(3) . ?
C9 C11 1.397(3) . ?
C10 H10 1.0000 . ?
C11 H11 0.9500 . ?
C11 C12 1.387(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(4) . ?
C13 C14 1.383(4) . ?
C14 H14 0.9500 . ?
C15 H15 1.0000 . ?
C15 C16 1.548(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.544(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.382(4) . ?
C19 C24 1.386(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.392(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.384(4) . ?
C22 C23 1.383(4) . ?
C23 C24 1.373(4) . ?
C24 H24 0.9500 . ?
F1A C23A 1.362(3) . ?
O1A C13A 1.390(3) . ?
O1A C19A 1.396(3) . ?
O2A C15A 1.423(3) . ?
O2A H2AA 0.98(5) . ?
N1A H1AA 0.8822 . ?
N1A H1AB 0.8828 . ?
N1A C22A 1.402(3) . ?
C1A H1AC 0.9900 . ?
C1A H1AD 0.9900 . ?
C1A C2A 1.541(3) . ?
C1A C10A 1.540(3) . ?
C2A H2AB 0.9900 . ?
C2A H2AC 0.9900 . ?
C2A C3A 1.524(3) . ?
C3A C4A 1.533(3) . ?
C3A C15A 1.533(3) . ?
C3A C18A 1.533(3) . ?
C4A H4A 1.0000 . ?
C4A C5A 1.519(3) . ?
C4A C17A 1.540(3) . ?
C5A H5A 1.0000 . ?
C5A C6A 1.527(3) . ?
C5A C10A 1.540(3) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C6A C7A 1.521(3) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C7A C8A 1.512(3) . ?
C8A C9A 1.403(3) . ?
C8A C14A 1.394(3) . ?
C9A C10A 1.529(3) . ?
C9A C11A 1.388(3) . ?
C10A H10A 1.0000 . ?
C11A H11A 0.9500 . ?
C11A C12A 1.390(3) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.383(3) . ?
C13A C14A 1.378(3) . ?
C14A H14A 0.9500 . ?
C15A H15A 1.0000 . ?
C15A C16A 1.546(4) . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C16A C17A 1.548(4) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C19A C20A 1.379(4) . ?
C19A C24A 1.389(4) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.386(3) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.392(3) . ?
C22A C23A 1.391(3) . ?
C23A C24A 1.370(3) . ?
C24A H24A 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
C13 O1 C19 119.64(19) . . ?
C15 O2 H2 109.5 . . ?
C22 N1 H1A 113(2) . . ?
C22 N1 H1B 115(2) . . ?
H1A N1 H1B 111(3) . . ?
H1C C1 H1D 107.8 . . ?
C2 C1 H1C 109.0 . . ?
C2 C1 H1D 109.0 . . ?
C10 C1 H1C 109.0 . . ?
C10 C1 H1D 109.0 . . ?
C10 C1 C2 112.89(19) . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 C1 111.17(19) . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C2 C3 C4 108.74(19) . . ?
C2 C3 C15 116.3(2) . . ?
C2 C3 C18 110.0(2) . . ?
C4 C3 C15 98.57(19) . . ?
C18 C3 C4 113.29(19) . . ?
C18 C3 C15 109.6(2) . . ?
C3 C4 H4 106.4 . . ?
C5 C4 C3 114.04(19) . . ?
C5 C4 H4 106.4 . . ?
C5 C4 C17 119.0(2) . . ?
C17 C4 C3 103.9(2) . . ?
C17 C4 H4 106.4 . . ?
C4 C5 H5 108.5 . . ?
C4 C5 C6 113.0(2) . . ?
C4 C5 C10 109.07(18) . . ?
C6 C5 H5 108.5 . . ?
C6 C5 C10 109.3(2) . . ?
C10 C5 H5 108.5 . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 C5 110.0(2) . . ?
C7 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
C6 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 C6 113.58(19) . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C9 C8 C7 122.6(2) . . ?
C14 C8 C7 117.7(2) . . ?
C14 C8 C9 119.7(2) . . ?
C8 C9 C10 120.3(2) . . ?
C11 C9 C8 117.5(2) . . ?
C11 C9 C10 122.2(2) . . ?
C1 C10 C5 111.69(19) . . ?
C1 C10 H10 106.6 . . ?
C5 C10 H10 106.6 . . ?
C9 C10 C1 114.15(19) . . ?
C9 C10 C5 110.78(18) . . ?
C9 C10 H10 106.6 . . ?
C9 C11 H11 118.5 . . ?
C12 C11 C9 122.9(2) . . ?
C12 C11 H11 118.5 . . ?
C11 C12 H12 120.8 . . ?
C11 C12 C13 118.4(2) . . ?
C13 C12 H12 120.8 . . ?
O1 C13 C12 124.5(2) . . ?
O1 C13 C14 115.4(2) . . ?
C14 C13 C12 120.1(2) . . ?
C8 C14 H14 119.3 . . ?
C13 C14 C8 121.4(2) . . ?
C13 C14 H14 119.3 . . ?
O2 C15 C3 116.5(2) . . ?
O2 C15 H15 108.6 . . ?
O2 C15 C16 110.4(2) . . ?
C3 C15 H15 108.6 . . ?
C3 C15 C16 103.9(2) . . ?
C16 C15 H15 108.6 . . ?
C15 C16 H16A 110.6 . . ?
C15 C16 H16B 110.6 . . ?
H16A C16 H16B 108.7 . . ?
C17 C16 C15 105.8(2) . . ?
C17 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
C4 C17 C16 103.5(2) . . ?
C4 C17 H17A 111.1 . . ?
C4 C17 H17B 111.1 . . ?
C16 C17 H17A 111.1 . . ?
C16 C17 H17B 111.1 . . ?
H17A C17 H17B 109.0 . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 O1 121.1(3) . . ?
C20 C19 C24 120.2(2) . . ?
C24 C19 O1 118.4(2) . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.1(2) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 121.0(2) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 N1 122.6(2) . . ?
C23 C22 N1 120.6(2) . . ?
C23 C22 C21 116.7(2) . . ?
F1 C23 C22 117.3(2) . . ?
F1 C23 C24 118.6(2) . . ?
C24 C23 C22 124.1(2) . . ?
C19 C24 H24 121.0 . . ?
C23 C24 C19 117.9(2) . . ?
C23 C24 H24 121.0 . . ?
C13A O1A C19A 118.40(18) . . ?
C15A O2A H2AA 111(3) . . ?
H1AA N1A H1AB 109.3 . . ?
C22A N1A H1AA 109.9 . . ?
C22A N1A H1AB 109.5 . . ?
H1AC C1A H1AD 107.9 . . ?
C2A C1A H1AC 109.1 . . ?
C2A C1A H1AD 109.1 . . ?
C10A C1A H1AC 109.1 . . ?
C10A C1A H1AD 109.1 . . ?
C10A C1A C2A 112.3(2) . . ?
C1A C2A H2AB 109.4 . . ?
C1A C2A H2AC 109.4 . . ?
H2AB C2A H2AC 108.0 . . ?
C3A C2A C1A 111.1(2) . . ?
C3A C2A H2AB 109.4 . . ?
C3A C2A H2AC 109.4 . . ?
C2A C3A C4A 109.20(19) . . ?
C2A C3A C15A 115.5(2) . . ?
C2A C3A C18A 109.8(2) . . ?
C4A C3A C15A 98.21(18) . . ?
C4A C3A C18A 113.7(2) . . ?
C18A C3A C15A 110.18(19) . . ?
C3A C4A H4A 106.5 . . ?
C3A C4A C17A 103.48(19) . . ?
C5A C4A C3A 113.95(18) . . ?
C5A C4A H4A 106.5 . . ?
C5A C4A C17A 119.2(2) . . ?
C17A C4A H4A 106.5 . . ?
C4A C5A H5A 109.0 . . ?
C4A C5A C6A 112.66(18) . . ?
C4A C5A C10A 108.51(18) . . ?
C6A C5A H5A 109.0 . . ?
C6A C5A C10A 108.67(18) . . ?
C10A C5A H5A 109.0 . . ?
C5A C6A H6AA 109.5 . . ?
C5A C6A H6AB 109.5 . . ?
H6AA C6A H6AB 108.1 . . ?
C7A C6A C5A 110.65(19) . . ?
C7A C6A H6AA 109.5 . . ?
C7A C6A H6AB 109.5 . . ?
C6A C7A H7AA 108.9 . . ?
C6A C7A H7AB 108.9 . . ?
H7AA C7A H7AB 107.7 . . ?
C8A C7A C6A 113.5(2) . . ?
C8A C7A H7AA 108.9 . . ?
C8A C7A H7AB 108.9 . . ?
C9A C8A C7A 122.1(2) . . ?
C14A C8A C7A 118.1(2) . . ?
C14A C8A C9A 119.8(2) . . ?
C8A C9A C10A 120.1(2) . . ?
C11A C9A C8A 117.6(2) . . ?
C11A C9A C10A 122.2(2) . . ?
C1A C10A C5A 112.06(18) . . ?
C1A C10A H10A 106.0 . . ?
C5A C10A H10A 106.0 . . ?
C9A C10A C1A 114.31(19) . . ?
C9A C10A C5A 111.79(19) . . ?
C9A C10A H10A 106.0 . . ?
C9A C11A H11A 118.5 . . ?
C9A C11A C12A 123.0(2) . . ?
C12A C11A H11A 118.5 . . ?
C11A C12A H12A 120.9 . . ?
C13A C12A C11A 118.2(2) . . ?
C13A C12A H12A 120.9 . . ?
C12A C13A O1A 124.6(2) . . ?
C14A C13A O1A 115.0(2) . . ?
C14A C13A C12A 120.4(2) . . ?
C8A C14A H14A 119.5 . . ?
C13A C14A C8A 121.0(2) . . ?
C13A C14A H14A 119.5 . . ?
O2A C15A C3A 117.1(2) . . ?
O2A C15A H15A 106.9 . . ?
O2A C15A C16A 114.9(2) . . ?
C3A C15A H15A 106.9 . . ?
C3A C15A C16A 103.3(2) . . ?
C16A C15A H15A 106.9 . . ?
C15A C16A H16C 110.7 . . ?
C15A C16A H16D 110.7 . . ?
C15A C16A C17A 105.1(2) . . ?
H16C C16A H16D 108.8 . . ?
C17A C16A H16C 110.7 . . ?
C17A C16A H16D 110.7 . . ?
C4A C17A C16A 103.7(2) . . ?
C4A C17A H17C 111.0 . . ?
C4A C17A H17D 111.0 . . ?
C16A C17A H17C 111.0 . . ?
C16A C17A H17D 111.0 . . ?
H17C C17A H17D 109.0 . . ?
C3A C18A H18D 109.5 . . ?
C3A C18A H18E 109.5 . . ?
C3A C18A H18F 109.5 . . ?
H18D C18A H18E 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C20A C19A O1A 118.5(2) . . ?
C20A C19A C24A 120.7(2) . . ?
C24A C19A O1A 120.7(2) . . ?
C19A C20A H20A 120.2 . . ?
C19A C20A C21A 119.5(2) . . ?
C21A C20A H20A 120.2 . . ?
C20A C21A H21A 119.2 . . ?
C20A C21A C22A 121.5(2) . . ?
C22A C21A H21A 119.2 . . ?
C21A C22A N1A 121.8(2) . . ?
C23A C22A N1A 121.5(2) . . ?
C23A C22A C21A 116.6(2) . . ?
F1A C23A C22A 118.0(2) . . ?
F1A C23A C24A 118.6(2) . . ?
C24A C23A C22A 123.4(2) . . ?
C19A C24A H24A 120.9 . . ?
C23A C24A C19A 118.2(2) . . ?
C23A C24A H24A 120.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1AA O2A 0.88 2.05 2.896(3) 159.9 1_646
N1A H1AB O2 0.88 2.06 2.832(3) 146.2 .
O2A H2AA N1 0.98(5) 2.06(4) 2.872(3) 140(4) .

_olex2_submission_special_instructions 'No special instructions were received'
