data_global

#==========================================================================

# SUBMISSION DETAILS


_publ_contact_author_name         'Pro. Sheng-Jiao Yan'
_publ_contact_author_address
;
Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan 
University), Ministry of Education, School of Chemical Science and
Technology, Yunnan University, Kunming, 650091, P. R. China
;
_publ_contact_author_email         yansj@ynu.edu.cn
_publ_contact_author_fax          '+86 871 65031633'
_publ_contact_author_phone        '+86 871 65031633'

_publ_requested_journal           'J. Org. Chem.'
_publ_requested_category          ?
_publ_requested_coeditor_name     ?

#==========================================================================

# TITLE AND AUTHOR LIST

_publ_section_title
;

Cascade reaction of Morita¨CBaylis¨CHillman acetates with 1,1-enediamines or heterocyclic
ketene aminals: Synthesis of highly functionalized 2-aminopyrroles

;

_publ_section_title_footnote
.

loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
' Jin Liu'  .
;Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan 
University), Ministry of Education, School of Chemical Science and
Technology, Yunnan University, Kunming, 650091, P. R. China
;
' Qi Li'  .
;Faculty of Life Science and Technology, Kunming University of 
Science and Technology, Kunming, 650504, P. R. China
;
' Zheng-Mao Cao'  .
;Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan 
University), Ministry of Education, School of Chemical Science and
Technology, Yunnan University, Kunming, 650091, P. R. China
;

'Jun Lin^*^'  .
;Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan 
University), Ministry of Education, School of Chemical Science and
Technology, Yunnan University, Kunming, 650091, P. R. China
;
' Sheng-Jiao Yan ^*^'  .
;Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan 
University), Ministry of Education, School of Chemical Science and
Technology, Yunnan University, Kunming, 650091, P. R. China
;
#==========================================================================  


# TEXT

_publ_section_abstract
;
A novel approach for the construction of two kinds of fully substituted pyrroles including 2-aminopyrroles
and bicyclic pyrroles from Morita¨CBaylis¨CHillman (MBH) acetates with 1,1-enediamines (EDAMs) or heterocyclic
ketene aminals (HKAs) via base-promoted tandem Michael-elimination, aromatization sequence has been
developed, affording the desired products in moderate to excellent yields. This methodology is a highly efficient, 
concise way to access 2-aminopyrroles or bicyclic pyrroles with diversity in molecular structures from readily
 available building blocks under mild reaction conditions.
; 
data_1
 
_audit_creation_method            SHELXL-2014
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C20 H17 F2 N3 O4' 
_chemical_formula_weight          401.36

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'
 'F'  'F'   0.0171   0.0103
 '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'
 
_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+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 
_cell_length_a                    9.1649(13)
_cell_length_b                    10.6661(15)
_cell_length_c                    19.060(3)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1863.2(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     1901    
_cell_measurement_theta_min       2.4659    
_cell_measurement_theta_max       20.2808  
 
_exptl_crystal_description        block 
_exptl_crystal_colour             yellow
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.431          
_exptl_crystal_F_000              832
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.360
_exptl_crystal_size_mid           0.300
_exptl_crystal_size_min           0.250
_exptl_absorpt_coefficient_mu     0.114
_shelx_estimated_absorpt_T_min    0.960
_shelx_estimated_absorpt_T_max    0.972
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.955  
_exptl_absorpt_correction_T_max   0.964  
_exptl_absorpt_process_details    sadabs  
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'sealed tube'                        
_diffrn_measurement_device_type   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans'  
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             10561
_diffrn_reflns_av_unetI/netI      0.0497
_diffrn_reflns_av_R_equivalents   0.0444
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          2.137
_diffrn_reflns_theta_max          24.997
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  0.975
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   0.975
_diffrn_reflns_point_group_measured_fraction_max   1.000
_diffrn_reflns_point_group_measured_fraction_full  0.974
_reflns_number_total              3280
_reflns_number_gt                 2302
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.735
_reflns_Friedel_fraction_max      1.000
_reflns_Friedel_fraction_full     0.973
 
_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        'Bruker SMART'
_computing_cell_refinement        'Bruker SMART'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement   'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics     'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material   'SHELXL-2014 (Sheldrick, 2014)'
 
_refine_special_details
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0438P)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      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack    0.6(14)
_chemical_absolute_configuration  ?
_refine_ls_number_reflns          3280
_refine_ls_number_parameters      264
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0695
_refine_ls_R_factor_gt            0.0394
_refine_ls_wR_factor_ref          0.0897
_refine_ls_wR_factor_gt           0.0799
_refine_ls_goodness_of_fit_ref    0.956
_refine_ls_restrained_S_all       0.956
_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
F1 F 0.8305(3) 0.97196(19) 0.73257(13) 0.0883(8) Uani 1 1 d . . . . .
F2 F 0.8926(3) -0.0459(2) 0.37739(12) 0.0816(7) Uani 1 1 d . . . . .
O1 O 0.4973(3) 0.1930(2) 0.71577(14) 0.0619(7) Uani 1 1 d . . . . .
O2 O 0.5669(3) 0.0969(2) 0.62027(14) 0.0602(7) Uani 1 1 d . . . . .
O3 O 1.0099(3) 0.6706(3) 0.50131(15) 0.0774(9) Uani 1 1 d . . . . .
O4 O 0.8031(3) 0.5752(2) 0.47223(13) 0.0539(7) Uani 1 1 d . . . . .
N1 N 0.7610(3) 0.4788(2) 0.65340(14) 0.0438(7) Uani 1 1 d . . . . .
N2 N 0.5849(3) 0.4323(2) 0.73999(14) 0.0515(8) Uani 1 1 d . . . . .
H2A H 0.5930 0.5061 0.7578 0.062 Uiso 1 1 calc R U . . .
H2B H 0.5250 0.3793 0.7581 0.062 Uiso 1 1 calc R U . . .
N3 N 0.5753(3) 0.1876(3) 0.66067(16) 0.0481(7) Uani 1 1 d . . . . .
C1 C 0.7826(4) 0.6072(3) 0.67284(17) 0.0407(8) Uani 1 1 d . . . . .
C1AA C 0.7854(4) 0.2402(3) 0.46384(19) 0.0494(9) Uani 1 1 d . . . . .
H1AA H 0.7503 0.3194 0.4522 0.059 Uiso 1 1 calc R U . . .
C2 C 0.7106(4) 0.7008(3) 0.63696(18) 0.0466(9) Uani 1 1 d . . . . .
H2 H 0.6504 0.6804 0.5994 0.056 Uiso 1 1 calc R U . . .
C3 C 0.7275(4) 0.8246(3) 0.6566(2) 0.0550(10) Uani 1 1 d . . . . .
H3 H 0.6804 0.8885 0.6323 0.066 Uiso 1 1 calc R U . . .
C4 C 0.8143(5) 0.8501(3) 0.7120(2) 0.0554(10) Uani 1 1 d . . . . .
C5 C 0.8891(4) 0.7606(4) 0.7489(2) 0.0592(11) Uani 1 1 d . . . . .
H5 H 0.9493 0.7821 0.7863 0.071 Uiso 1 1 calc R U . . .
C6 C 0.8719(4) 0.6369(3) 0.72857(19) 0.0535(10) Uani 1 1 d . . . . .
H6 H 0.9207 0.5737 0.7526 0.064 Uiso 1 1 calc R U . . .
C7 C 0.6649(4) 0.4003(3) 0.68454(17) 0.0430(8) Uani 1 1 d . . . . .
C8 C 0.6682(4) 0.2876(3) 0.64648(17) 0.0429(8) Uani 1 1 d . . . . .
C9 C 0.7694(4) 0.3016(3) 0.58936(17) 0.0425(8) Uani 1 1 d . . . . .
C10 C 0.8261(4) 0.4184(3) 0.59490(17) 0.0432(8) Uani 1 1 d . . . . .
C11 C 0.8053(4) 0.2099(3) 0.53308(19) 0.0431(8) Uani 1 1 d . . . . .
C12 C 0.8609(4) 0.0913(3) 0.54884(19) 0.0574(11) Uani 1 1 d . . . . .
H12 H 0.8782 0.0697 0.5954 0.069 Uiso 1 1 calc R U . . .
C13 C 0.8905(4) 0.0058(3) 0.4965(2) 0.0616(11) Uani 1 1 d . . . . .
H13 H 0.9267 -0.0734 0.5074 0.074 Uiso 1 1 calc R U . . .
C14 C 0.8659(4) 0.0393(4) 0.4292(2) 0.0552(10) Uani 1 1 d . . . . .
C15 C 0.8166(4) 0.1549(4) 0.41069(19) 0.0555(10) Uani 1 1 d . . . . .
H15 H 0.8040 0.1764 0.3638 0.067 Uiso 1 1 calc R U . . .
C16 C 0.9522(4) 0.4767(3) 0.55776(18) 0.0489(9) Uani 1 1 d . . . . .
H16A H 1.0002 0.4113 0.5310 0.059 Uiso 1 1 calc R U . . .
H16B H 1.0209 0.5046 0.5932 0.059 Uiso 1 1 calc R U . . .
C17 C 0.9250(4) 0.5858(3) 0.50856(19) 0.0476(9) Uani 1 1 d . . . . .
C18 C 0.7805(5) 0.6700(4) 0.4190(2) 0.0677(12) Uani 1 1 d . . . . .
H18A H 0.8695 0.6822 0.3923 0.081 Uiso 1 1 calc R U . . .
H18B H 0.7546 0.7490 0.4408 0.081 Uiso 1 1 calc R U . . .
C19 C 0.6621(5) 0.6286(6) 0.3721(2) 0.1055(18) Uani 1 1 d . . . . .
H19A H 0.6595 0.6814 0.3313 0.158 Uiso 1 1 calc R U . . .
H19B H 0.5705 0.6340 0.3963 0.158 Uiso 1 1 calc R U . . .
H19C H 0.6791 0.5434 0.3580 0.158 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
F1 C4 1.365(4) . ?
F2 C14 1.365(4) . ?
O1 N3 1.272(4) . ?
O2 N3 1.238(3) . ?
O3 C17 1.201(4) . ?
O4 C17 1.319(4) . ?
O4 C18 1.447(4) . ?
N1 C7 1.353(4) . ?
N1 C10 1.419(4) . ?
N1 C1 1.433(4) . ?
N2 C7 1.331(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 C8 1.392(4) . ?
C1 C6 1.378(5) . ?
C1 C2 1.378(4) . ?
C1AA C11 1.371(4) . ?
C1AA C15 1.391(5) . ?
C1AA H1AA 0.9300 . ?
C2 C3 1.381(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.350(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(5) . ?
C5 C6 1.384(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.404(5) . ?
C8 C9 1.438(4) . ?
C9 C10 1.353(4) . ?
C9 C11 1.489(5) . ?
C10 C16 1.491(4) . ?
C11 C12 1.396(4) . ?
C12 C13 1.379(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.351(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.360(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.515(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 C19 1.474(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C17 O4 C18 115.4(3) . . ?
C7 N1 C10 109.7(3) . . ?
C7 N1 C1 124.6(3) . . ?
C10 N1 C1 125.4(3) . . ?
C7 N2 H2A 120.0 . . ?
C7 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
O2 N3 O1 120.9(3) . . ?
O2 N3 C8 121.1(3) . . ?
O1 N3 C8 118.0(3) . . ?
C6 C1 C2 120.0(3) . . ?
C6 C1 N1 120.1(3) . . ?
C2 C1 N1 119.9(3) . . ?
C11 C1AA C15 121.3(3) . . ?
C11 C1AA H1AA 119.4 . . ?
C15 C1AA H1AA 119.4 . . ?
C1 C2 C3 120.3(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 118.1(3) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 F1 118.7(4) . . ?
C3 C4 C5 123.8(3) . . ?
F1 C4 C5 117.5(4) . . ?
C4 C5 C6 117.6(4) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C1 C6 C5 120.2(3) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N2 C7 N1 123.2(3) . . ?
N2 C7 C8 130.0(3) . . ?
N1 C7 C8 106.8(3) . . ?
N3 C8 C7 122.8(3) . . ?
N3 C8 C9 128.4(3) . . ?
C7 C8 C9 108.5(3) . . ?
C10 C9 C8 106.5(3) . . ?
C10 C9 C11 125.2(3) . . ?
C8 C9 C11 128.3(3) . . ?
C9 C10 N1 108.5(3) . . ?
C9 C10 C16 130.1(3) . . ?
N1 C10 C16 120.6(3) . . ?
C1AA C11 C12 118.0(3) . . ?
C1AA C11 C9 120.6(3) . . ?
C12 C11 C9 121.4(3) . . ?
C13 C12 C11 121.1(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 118.6(3) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C13 C14 C15 122.8(3) . . ?
C13 C14 F2 118.8(3) . . ?
C15 C14 F2 118.4(3) . . ?
C14 C15 C1AA 118.2(3) . . ?
C14 C15 H15 120.9 . . ?
C1AA C15 H15 120.9 . . ?
C10 C16 C17 119.1(3) . . ?
C10 C16 H16A 107.5 . . ?
C17 C16 H16A 107.5 . . ?
C10 C16 H16B 107.5 . . ?
C17 C16 H16B 107.5 . . ?
H16A C16 H16B 107.0 . . ?
O3 C17 O4 123.6(3) . . ?
O3 C17 C16 122.9(3) . . ?
O4 C17 C16 113.5(3) . . ?
O4 C18 C19 108.8(4) . . ?
O4 C18 H18A 109.9 . . ?
C19 C18 H18A 109.9 . . ?
O4 C18 H18B 109.9 . . ?
C19 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C7 N1 C1 C6 82.5(4) . . . . ?
C10 N1 C1 C6 -104.0(4) . . . . ?
C7 N1 C1 C2 -95.7(4) . . . . ?
C10 N1 C1 C2 77.8(4) . . . . ?
C6 C1 C2 C3 0.0(5) . . . . ?
N1 C1 C2 C3 178.2(3) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 F1 -179.2(3) . . . . ?
C2 C3 C4 C5 1.5(6) . . . . ?
C3 C4 C5 C6 -1.2(6) . . . . ?
F1 C4 C5 C6 179.5(3) . . . . ?
C2 C1 C6 C5 0.3(5) . . . . ?
N1 C1 C6 C5 -177.9(3) . . . . ?
C4 C5 C6 C1 0.3(6) . . . . ?
C10 N1 C7 N2 -178.5(3) . . . . ?
C1 N1 C7 N2 -4.1(5) . . . . ?
C10 N1 C7 C8 0.5(4) . . . . ?
C1 N1 C7 C8 175.0(3) . . . . ?
O2 N3 C8 C7 169.8(3) . . . . ?
O1 N3 C8 C7 -9.0(5) . . . . ?
O2 N3 C8 C9 -3.3(5) . . . . ?
O1 N3 C8 C9 177.9(3) . . . . ?
N2 C7 C8 N3 3.5(6) . . . . ?
N1 C7 C8 N3 -175.4(3) . . . . ?
N2 C7 C8 C9 177.8(3) . . . . ?
N1 C7 C8 C9 -1.1(4) . . . . ?
N3 C8 C9 C10 175.2(3) . . . . ?
C7 C8 C9 C10 1.3(4) . . . . ?
N3 C8 C9 C11 -3.3(6) . . . . ?
C7 C8 C9 C11 -177.2(3) . . . . ?
C8 C9 C10 N1 -1.0(4) . . . . ?
C11 C9 C10 N1 177.6(3) . . . . ?
C8 C9 C10 C16 168.9(3) . . . . ?
C11 C9 C10 C16 -12.5(6) . . . . ?
C7 N1 C10 C9 0.3(4) . . . . ?
C1 N1 C10 C9 -174.1(3) . . . . ?
C7 N1 C10 C16 -170.7(3) . . . . ?
C1 N1 C10 C16 14.9(5) . . . . ?
C15 C1AA C11 C12 1.3(6) . . . . ?
C15 C1AA C11 C9 -179.1(3) . . . . ?
C10 C9 C11 C1AA -56.9(5) . . . . ?
C8 C9 C11 C1AA 121.4(4) . . . . ?
C10 C9 C11 C12 122.7(4) . . . . ?
C8 C9 C11 C12 -59.0(5) . . . . ?
C1AA C11 C12 C13 -2.0(5) . . . . ?
C9 C11 C12 C13 178.4(3) . . . . ?
C11 C12 C13 C14 0.6(6) . . . . ?
C12 C13 C14 C15 1.7(6) . . . . ?
C12 C13 C14 F2 -178.8(3) . . . . ?
C13 C14 C15 C1AA -2.4(6) . . . . ?
F2 C14 C15 C1AA 178.1(3) . . . . ?
C11 C1AA C15 C14 0.8(6) . . . . ?
C9 C10 C16 C17 114.9(4) . . . . ?
N1 C10 C16 C17 -76.2(4) . . . . ?
C18 O4 C17 O3 3.4(5) . . . . ?
C18 O4 C17 C16 -173.4(3) . . . . ?
C10 C16 C17 O3 145.8(4) . . . . ?
C10 C16 C17 O4 -37.4(4) . . . . ?
C17 O4 C18 C19 166.0(3) . . . . ?
 
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 
C18 H18B O3  0.97 2.64 3.369(5) 132.0 3_466
C6 H6 F1  0.93 2.54 3.329(4) 142.8 4_746
C3 H3 O2  0.93 2.46 3.329(4) 154.6 1_565
N2 H2B O1  0.86 2.16 2.715(4) 122.1 .
N2 H2A O1  0.86 2.22 3.001(3) 151.7 4_656
N2 H2B O1  0.86 2.16 2.715(4) 122.1 .
C3 H3 O2  0.93 2.46 3.329(4) 154.6 1_565
C6 H6 F1  0.93 2.54 3.329(4) 142.8 4_746
C18 H18B O3  0.97 2.64 3.369(5) 132.0 3_466
N2 H2A O1  0.86 2.22 3.001(3) 151.7 4_656
N2 H2B O1  0.86 2.16 2.715(4) 122.1 .
C3 H3 O2  0.93 2.46 3.329(4) 154.6 1_565
C6 H6 F1  0.93 2.54 3.329(4) 142.8 4_746
C18 H18B O3  0.97 2.64 3.369(5) 132.0 3_466
 
_refine_diff_density_max    0.114
_refine_diff_density_min   -0.151
_refine_diff_density_rms    0.034

_shelxl_version_number 2014-3



