# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_SP_DG_108
_database_code_depnum_ccdc_archive 'CCDC 2266922'
loop_
_audit_author_name
_audit_author_address
'Debraj Ghorai'
;IIT Kharagpur
India
;
_audit_update_record             
;
2023-06-01 deposited with the CCDC.	2023-10-23 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         'C19 H19 N O'
_chemical_formula_sum            'C19 H19 N O'
_chemical_formula_weight         277.35

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'
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      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                   11.7963(7)
_cell_length_b                   8.2830(4)
_cell_length_c                   15.9743(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.775(2)
_cell_angle_gamma                90
_cell_volume                     1502.04(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    6040
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      27.64
_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26754
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.919
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2795
_reflns_number_gt                2033
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_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)+(0.1136P)²+0.2533P] 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       0.049(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2795
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1937
_refine_ls_wR_factor_gt          0.1654
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
C1 C 0.63429(19) 0.5711(2) 0.33381(13) 0.0433(5) Uani 1 1 d . . . . .
C2 C 0.5360(2) 0.5659(3) 0.26243(13) 0.0511(6) Uani 1 1 d . . . . .
H2 H 0.477508 0.489051 0.259523 0.061 Uiso 1 1 calc R U . . .
C3 C 0.5257(2) 0.6765(3) 0.19539(15) 0.0617(7) Uani 1 1 d . . . . .
H3 H 0.460217 0.672765 0.147343 0.074 Uiso 1 1 calc R U . . .
C4 C 0.6109(3) 0.7911(3) 0.19903(18) 0.0681(7) Uani 1 1 d . . . . .
H4 H 0.602138 0.864179 0.153525 0.082 Uiso 1 1 calc R U . . .
C5 C 0.7096(2) 0.7995(3) 0.26927(18) 0.0633(7) Uani 1 1 d . . . . .
H5 H 0.767367 0.877057 0.271604 0.076 Uiso 1 1 calc R U . . .
C6 C 0.7199(2) 0.6898(2) 0.33582(14) 0.0475(6) Uani 1 1 d . . . . .
C7 C 0.7892(2) 0.5524(2) 0.46388(14) 0.0481(6) Uani 1 1 d . . . . .
C8 C 0.67505(19) 0.4758(2) 0.41436(13) 0.0432(5) Uani 1 1 d . . . . .
C9 C 0.62718(19) 0.3420(2) 0.43893(13) 0.0460(5) Uani 1 1 d . . . . .
C10 C 0.51714(19) 0.2741(2) 0.38021(13) 0.0463(6) Uani 1 1 d . . . . .
C11 C 0.5211(2) 0.1692(3) 0.31311(14) 0.0557(6) Uani 1 1 d . . . . .
H11 H 0.593547 0.137416 0.306123 0.067 Uiso 1 1 calc R U . . .
C12 C 0.4189(3) 0.1120(3) 0.25685(17) 0.0677(7) Uani 1 1 d . . . . .
H12 H 0.422918 0.042458 0.212034 0.081 Uiso 1 1 calc R U . . .
C13 C 0.3117(2) 0.1566(3) 0.26644(17) 0.0690(8) Uani 1 1 d . . . . .
H13 H 0.242904 0.117979 0.228117 0.083 Uiso 1 1 calc R U . . .
C14 C 0.3057(2) 0.2593(3) 0.33329(18) 0.0653(7) Uani 1 1 d . . . . .
H14 H 0.232814 0.289924 0.340058 0.078 Uiso 1 1 calc R U . . .
C15 C 0.4076(2) 0.3162(3) 0.38979(16) 0.0550(6) Uani 1 1 d . . . . .
H15 H 0.402912 0.384082 0.435135 0.066 Uiso 1 1 calc R U . . .
C16 C 0.6813(2) 0.2505(3) 0.52232(15) 0.0581(6) Uani 1 1 d . . . . .
H16 H 0.739393 0.321322 0.560662 0.070 Uiso 1 1 calc R U . . .
C17 C 0.5916(3) 0.2021(3) 0.57045(16) 0.0711(8) Uani 1 1 d . . . . .
H17A H 0.552211 0.296666 0.583046 0.107 Uiso 1 1 calc R U . . .
H17B H 0.631139 0.148997 0.623833 0.107 Uiso 1 1 calc R U . . .
H17C H 0.534895 0.129890 0.534834 0.107 Uiso 1 1 calc R U . . .
C18 C 0.7461(3) 0.1023(4) 0.5026(2) 0.0934(10) Uani 1 1 d . . . . .
H18A H 0.690314 0.027764 0.467977 0.140 Uiso 1 1 calc R U . . .
H18B H 0.787580 0.051253 0.556095 0.140 Uiso 1 1 calc R U . . .
H18C H 0.801201 0.134437 0.471212 0.140 Uiso 1 1 calc R U . . .
C19 C 0.9189(2) 0.7689(3) 0.43362(18) 0.0674(7) Uani 1 1 d . . . . .
H19A H 0.970350 0.730078 0.487194 0.101 Uiso 1 1 calc R U . . .
H19B H 0.901043 0.880551 0.439852 0.101 Uiso 1 1 calc R U . . .
H19C H 0.956908 0.757642 0.387875 0.101 Uiso 1 1 calc R U . . .
N1 N 0.81062(17) 0.6755(2) 0.41233(12) 0.0525(5) Uani 1 1 d . . . . .
O1 O 0.85573(16) 0.5192(2) 0.53485(11) 0.0671(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.389(3) . ?
C1 C6 1.403(3) . ?
C1 C8 1.474(3) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.393(3) . ?
C7 O1 1.221(3) . ?
C7 N1 1.377(3) . ?
C7 C8 1.504(3) . ?
C8 C9 1.350(3) . ?
C9 C10 1.490(3) . ?
C9 C16 1.514(3) . ?
C10 C15 1.387(3) . ?
C10 C11 1.390(3) . ?
C11 C12 1.377(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.521(3) . ?
C16 C18 1.524(4) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N1 1.452(3) . ?
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
C2 C1 C6 118.43(18) . . ?
C2 C1 C8 134.53(19) . . ?
C6 C1 C8 107.04(19) . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 118.1(2) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 N1 128.2(2) . . ?
C5 C6 C1 122.1(2) . . ?
N1 C6 C1 109.71(17) . . ?
O1 C7 N1 123.1(2) . . ?
O1 C7 C8 130.57(19) . . ?
N1 C7 C8 106.33(19) . . ?
C9 C8 C1 129.1(2) . . ?
C9 C8 C7 125.37(19) . . ?
C1 C8 C7 105.43(17) . . ?
C8 C9 C10 119.27(19) . . ?
C8 C9 C16 123.8(2) . . ?
C10 C9 C16 116.85(18) . . ?
C15 C10 C11 118.0(2) . . ?
C15 C10 C9 120.93(19) . . ?
C11 C10 C9 121.0(2) . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.8(2) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C9 C16 C17 113.1(2) . . ?
C9 C16 C18 109.6(2) . . ?
C17 C16 C18 110.4(2) . . ?
C9 C16 H16 107.8 . . ?
C17 C16 H16 107.8 . . ?
C18 C16 H16 107.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C7 N1 C6 111.44(18) . . ?
C7 N1 C19 123.1(2) . . ?
C6 N1 C19 125.26(18) . . ?

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
C6 C1 C2 C3 0.5(3) . . . . ?
C8 C1 C2 C3 -179.3(2) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C5 C6 N1 -179.9(2) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C8 C1 C6 C5 179.41(19) . . . . ?
C2 C1 C6 N1 179.73(17) . . . . ?
C8 C1 C6 N1 -0.5(2) . . . . ?
C2 C1 C8 C9 5.0(4) . . . . ?
C6 C1 C8 C9 -174.8(2) . . . . ?
C2 C1 C8 C7 -178.7(2) . . . . ?
C6 C1 C8 C7 1.6(2) . . . . ?
O1 C7 C8 C9 -4.9(4) . . . . ?
N1 C7 C8 C9 174.36(19) . . . . ?
O1 C7 C8 C1 178.6(2) . . . . ?
N1 C7 C8 C1 -2.1(2) . . . . ?
C1 C8 C9 C10 -0.4(3) . . . . ?
C7 C8 C9 C10 -176.10(18) . . . . ?
C1 C8 C9 C16 177.11(19) . . . . ?
C7 C8 C9 C16 1.4(3) . . . . ?
C8 C9 C10 C15 -93.8(2) . . . . ?
C16 C9 C10 C15 88.5(2) . . . . ?
C8 C9 C10 C11 84.8(3) . . . . ?
C16 C9 C10 C11 -92.9(2) . . . . ?
C15 C10 C11 C12 1.3(3) . . . . ?
C9 C10 C11 C12 -177.3(2) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C13 C14 C15 C10 0.9(3) . . . . ?
C11 C10 C15 C14 -1.6(3) . . . . ?
C9 C10 C15 C14 177.1(2) . . . . ?
C8 C9 C16 C17 135.9(2) . . . . ?
C10 C9 C16 C17 -46.5(3) . . . . ?
C8 C9 C16 C18 -100.4(3) . . . . ?
C10 C9 C16 C18 77.2(3) . . . . ?
O1 C7 N1 C6 -178.7(2) . . . . ?
C8 C7 N1 C6 2.0(2) . . . . ?
O1 C7 N1 C19 5.6(3) . . . . ?
C8 C7 N1 C19 -173.75(19) . . . . ?
C5 C6 N1 C7 179.2(2) . . . . ?
C1 C6 N1 C7 -1.0(2) . . . . ?
C5 C6 N1 C19 -5.2(3) . . . . ?
C1 C6 N1 C19 174.6(2) . . . . ?

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.059



####################################################################### 
# 
# 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_SP_DG_222
_database_code_depnum_ccdc_archive 'CCDC 2266990'
loop_
_audit_author_name
_audit_author_address
'Debraj Ghorai'
;IIT Kharagpur
India
;
_audit_update_record             
;
2023-06-01 deposited with the CCDC.	2023-10-23 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         'C20 H28 B N O4'
_chemical_formula_sum            'C20 H28 B N O4'
_chemical_formula_weight         357.24

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'
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   8.6631(4)
_cell_length_b                   13.5282(6)
_cell_length_c                   35.3230(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4139.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      26.30
_exptl_crystal_description       block
_exptl_crystal_colour            colourless


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6521
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            72526
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.306
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3861
_reflns_number_gt                2894
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_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)+(0.0613P)²+3.2059P] 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       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3861
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.1817
_refine_ls_wR_factor_gt          0.1685
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.006
_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 0.5671(3) 0.62622(18) 0.49892(7) 0.0412(6) Uani 1 1 d . . . . .
C2 C 0.5686(3) 0.6250(2) 0.53765(7) 0.0483(7) Uani 1 1 d . . . . .
H2 H 0.661202 0.618251 0.550729 0.058 Uiso 1 1 calc R U . . .
C3 C 0.4299(3) 0.6339(2) 0.55726(8) 0.0512(7) Uani 1 1 d . . . . .
H3 H 0.429428 0.633031 0.583582 0.061 Uiso 1 1 calc R U . . .
C4 C 0.2927(3) 0.64399(19) 0.53760(7) 0.0468(6) Uani 1 1 d . . . . .
C5 C 0.2914(3) 0.64589(19) 0.49811(7) 0.0445(6) Uani 1 1 d . . . . .
H5 H 0.198721 0.653152 0.485129 0.053 Uiso 1 1 calc R U . . .
C6 C 0.4284(3) 0.63694(17) 0.47832(7) 0.0397(6) Uani 1 1 d . . . . .
C7 C 0.4700(3) 0.62874(18) 0.43804(7) 0.0413(6) Uani 1 1 d . . . . .
C8 C 0.6409(3) 0.61240(18) 0.43746(7) 0.0424(6) Uani 1 1 d . . . . .
C9 C 0.8513(3) 0.5992(2) 0.48467(8) 0.0556(7) Uani 1 1 d . . . . .
H9A H 0.915875 0.603342 0.462647 0.083 Uiso 1 1 calc R U . . .
H9B H 0.863293 0.535477 0.496230 0.083 Uiso 1 1 calc R U . . .
H9C H 0.880497 0.649710 0.502385 0.083 Uiso 1 1 calc R U . . .
C10 C 0.1446(4) 0.6461(2) 0.59469(8) 0.0685(9) Uani 1 1 d . . . . .
H10A H 0.184393 0.583408 0.602865 0.103 Uiso 1 1 calc R U . . .
H10B H 0.039809 0.653091 0.603098 0.103 Uiso 1 1 calc R U . . .
H10C H 0.206218 0.698279 0.605227 0.103 Uiso 1 1 calc R U . . .
C11 C 0.3927(3) 0.6308(2) 0.40500(7) 0.0467(6) Uani 1 1 d . . . . .
C12 C 0.2206(3) 0.6509(2) 0.40227(8) 0.0594(8) Uani 1 1 d . . . . .
H12 H 0.188174 0.681045 0.426211 0.071 Uiso 1 1 calc R U . . .
C13 C 0.1813(4) 0.7228(3) 0.37082(10) 0.0902(12) Uani 1 1 d . . . . .
H13A H 0.237034 0.783350 0.374561 0.135 Uiso 1 1 calc R U . . .
H13B H 0.072402 0.736095 0.371116 0.135 Uiso 1 1 calc R U . . .
H13C H 0.209374 0.694547 0.346867 0.135 Uiso 1 1 calc R U . . .
C14 C 0.1331(4) 0.5545(3) 0.39794(12) 0.0928(12) Uani 1 1 d . . . . .
H14A H 0.166721 0.521445 0.375349 0.139 Uiso 1 1 calc R U . . .
H14B H 0.024537 0.567977 0.396232 0.139 Uiso 1 1 calc R U . . .
H14C H 0.152704 0.513142 0.419482 0.139 Uiso 1 1 calc R U . . .
C15 C 0.6016(4) 0.6160(3) 0.31028(8) 0.0711(9) Uani 1 1 d . . . . .
C16 C 0.5639(6) 0.6672(4) 0.27340(10) 0.1095(15) Uani 1 1 d . . . . .
H16A H 0.454589 0.677887 0.271772 0.164 Uiso 1 1 calc R U . . .
H16B H 0.596921 0.626706 0.252617 0.164 Uiso 1 1 calc R U . . .
H16C H 0.616442 0.729688 0.272395 0.164 Uiso 1 1 calc R U . . .
C17 C 0.7742(4) 0.6207(4) 0.31785(11) 0.1002(14) Uani 1 1 d . . . . .
H17A H 0.806277 0.688494 0.319351 0.150 Uiso 1 1 calc R U . . .
H17B H 0.828639 0.588446 0.297640 0.150 Uiso 1 1 calc R U . . .
H17C H 0.796827 0.588001 0.341329 0.150 Uiso 1 1 calc R U . . .
C18 C 0.5337(4) 0.5112(3) 0.31504(9) 0.0755(10) Uani 1 1 d . . . . .
C19 C 0.3828(6) 0.4946(4) 0.29324(12) 0.1267(19) Uani 1 1 d . . . . .
H19A H 0.328800 0.439190 0.303880 0.190 Uiso 1 1 calc R U . . .
H19B H 0.405746 0.481517 0.267127 0.190 Uiso 1 1 calc R U . . .
H19C H 0.319537 0.552615 0.295077 0.190 Uiso 1 1 calc R U . . .
C20 C 0.6415(7) 0.4255(4) 0.30759(12) 0.1231(18) Uani 1 1 d . . . . .
H20A H 0.733816 0.433627 0.322298 0.185 Uiso 1 1 calc R U . . .
H20B H 0.667486 0.423783 0.281178 0.185 Uiso 1 1 calc R U . . .
H20C H 0.591668 0.364824 0.314555 0.185 Uiso 1 1 calc R U . . .
N1 N 0.6911(2) 0.61316(16) 0.47371(6) 0.0437(5) Uani 1 1 d . . . . .
O1 O 0.7205(2) 0.60131(16) 0.40901(5) 0.0584(6) Uani 1 1 d . . . . .
O2 O 0.1497(2) 0.65136(16) 0.55434(5) 0.0601(6) Uani 1 1 d . . . . .
O3 O 0.4903(3) 0.50846(16) 0.35492(5) 0.0650(6) Uani 1 1 d . . . . .
O4 O 0.5274(3) 0.67084(16) 0.34084(5) 0.0639(6) Uani 1 1 d . . . . .
B1 B 0.4815(4) 0.6038(3) 0.36738(9) 0.0524(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.368(4) . ?
C1 N1 1.406(3) . ?
C1 C6 1.412(3) . ?
C2 C3 1.392(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 O2 1.376(3) . ?
C4 C5 1.395(4) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.472(3) . ?
C7 C11 1.346(3) . ?
C7 C8 1.497(3) . ?
C8 O1 1.228(3) . ?
C8 N1 1.352(3) . ?
C9 N1 1.453(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O2 1.427(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.519(4) . ?
C11 B1 1.578(4) . ?
C12 C13 1.515(4) . ?
C12 C14 1.516(5) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O4 1.458(4) . ?
C15 C16 1.511(5) . ?
C15 C17 1.521(5) . ?
C15 C18 1.545(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O3 1.459(4) . ?
C18 C20 1.511(5) . ?
C18 C19 1.533(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O3 B1 1.366(4) . ?
O4 B1 1.364(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 128.6(2) . . ?
C2 C1 C6 121.7(2) . . ?
N1 C1 C6 109.7(2) . . ?
C1 C2 C3 119.2(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
O2 C4 C3 124.4(2) . . ?
O2 C4 C5 114.9(2) . . ?
C3 C4 C5 120.7(2) . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 C7 134.9(2) . . ?
C1 C6 C7 106.4(2) . . ?
C11 C7 C6 135.6(2) . . ?
C11 C7 C8 118.9(2) . . ?
C6 C7 C8 105.5(2) . . ?
O1 C8 N1 126.5(2) . . ?
O1 C8 C7 125.8(2) . . ?
N1 C8 C7 107.7(2) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 C12 123.2(2) . . ?
C7 C11 B1 118.9(2) . . ?
C12 C11 B1 117.8(2) . . ?
C13 C12 C14 111.4(3) . . ?
C13 C12 C11 112.5(3) . . ?
C14 C12 C11 110.1(3) . . ?
C13 C12 H12 107.5 . . ?
C14 C12 H12 107.5 . . ?
C11 C12 H12 107.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 C16 108.1(3) . . ?
O4 C15 C17 106.4(3) . . ?
C16 C15 C17 110.2(3) . . ?
O4 C15 C18 102.6(2) . . ?
C16 C15 C18 115.7(3) . . ?
C17 C15 C18 113.1(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 C20 108.0(3) . . ?
O3 C18 C19 105.2(3) . . ?
C20 C18 C19 109.1(4) . . ?
O3 C18 C15 103.1(2) . . ?
C20 C18 C15 116.7(4) . . ?
C19 C18 C15 113.8(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 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 N1 C1 110.8(2) . . ?
C8 N1 C9 123.9(2) . . ?
C1 N1 C9 125.2(2) . . ?
C4 O2 C10 117.0(2) . . ?
B1 O3 C18 107.6(2) . . ?
B1 O4 C15 107.4(3) . . ?
O4 B1 O3 113.0(3) . . ?
O4 B1 C11 124.6(3) . . ?
O3 B1 C11 121.1(3) . . ?

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
N1 C1 C2 C3 -176.3(2) . . . . ?
C6 C1 C2 C3 0.4(4) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 O2 178.7(2) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
O2 C4 C5 C6 -178.7(2) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C4 C5 C6 C7 174.8(3) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
N1 C1 C6 C5 176.9(2) . . . . ?
C2 C1 C6 C7 -176.5(2) . . . . ?
N1 C1 C6 C7 0.7(3) . . . . ?
C5 C6 C7 C11 3.4(5) . . . . ?
C1 C6 C7 C11 178.7(3) . . . . ?
C5 C6 C7 C8 -175.2(3) . . . . ?
C1 C6 C7 C8 0.2(3) . . . . ?
C11 C7 C8 O1 0.8(4) . . . . ?
C6 C7 C8 O1 179.6(2) . . . . ?
C11 C7 C8 N1 -179.9(2) . . . . ?
C6 C7 C8 N1 -1.0(3) . . . . ?
C6 C7 C11 C12 4.1(5) . . . . ?
C8 C7 C11 C12 -177.5(3) . . . . ?
C6 C7 C11 B1 -171.4(3) . . . . ?
C8 C7 C11 B1 7.0(4) . . . . ?
C7 C11 C12 C13 135.5(3) . . . . ?
B1 C11 C12 C13 -48.9(4) . . . . ?
C7 C11 C12 C14 -99.6(3) . . . . ?
B1 C11 C12 C14 76.1(3) . . . . ?
O4 C15 C18 O3 -24.5(3) . . . . ?
C16 C15 C18 O3 -141.9(3) . . . . ?
C17 C15 C18 O3 89.7(3) . . . . ?
O4 C15 C18 C20 -142.6(3) . . . . ?
C16 C15 C18 C20 100.0(4) . . . . ?
C17 C15 C18 C20 -28.4(4) . . . . ?
O4 C15 C18 C19 88.9(3) . . . . ?
C16 C15 C18 C19 -28.5(5) . . . . ?
C17 C15 C18 C19 -156.9(3) . . . . ?
O1 C8 N1 C1 -179.1(3) . . . . ?
C7 C8 N1 C1 1.5(3) . . . . ?
O1 C8 N1 C9 -0.9(4) . . . . ?
C7 C8 N1 C9 179.8(2) . . . . ?
C2 C1 N1 C8 175.6(3) . . . . ?
C6 C1 N1 C8 -1.4(3) . . . . ?
C2 C1 N1 C9 -2.7(4) . . . . ?
C6 C1 N1 C9 -179.7(2) . . . . ?
C3 C4 O2 C10 -1.3(4) . . . . ?
C5 C4 O2 C10 177.8(2) . . . . ?
C20 C18 O3 B1 142.8(3) . . . . ?
C19 C18 O3 B1 -100.9(3) . . . . ?
C15 C18 O3 B1 18.6(3) . . . . ?
C16 C15 O4 B1 144.9(3) . . . . ?
C17 C15 O4 B1 -96.8(3) . . . . ?
C18 C15 O4 B1 22.2(3) . . . . ?
C15 O4 B1 O3 -11.6(3) . . . . ?
C15 O4 B1 C11 -178.7(3) . . . . ?
C18 O3 B1 O4 -5.3(4) . . . . ?
C18 O3 B1 C11 162.2(3) . . . . ?
C7 C11 B1 O4 -105.4(3) . . . . ?
C12 C11 B1 O4 78.8(4) . . . . ?
C7 C11 B1 O3 88.6(3) . . . . ?
C12 C11 B1 O3 -87.2(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
_geom_hbond_publ_flag
C17 H17C O1 0.96 2.49 3.264(4) 138.0 . yes

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.040



####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2266991'
loop_
_audit_author_name
_audit_author_address
'Debraj Ghorai'
;IIT Kharagpur
India
;
_audit_update_record             
;
2023-06-01 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 N O'
_chemical_formula_weight         277.35

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'
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      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                   9.004(12)
_cell_length_b                   9.504(11)
_cell_length_c                   18.11(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.20(3)
_cell_angle_gamma                90
_cell_volume                     1546(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3823
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      28.3

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.993
_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 SMART APEX-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36329
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.421
_diffrn_reflns_theta_max         28.292
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3823
_reflns_number_gt                2358
_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       'Bruker SMART'
_computing_cell_refinement       ?
_computing_data_reduction        'Bruker Saint Plus'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0757P)²+0.2268P] 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         3823
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1661
_refine_ls_wR_factor_gt          0.1427
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
O001 O 0.32278(14) 0.51304(15) 0.32803(8) 0.0692(4) Uani 1 1 d . . . . .
N002 N 0.51749(16) 0.66235(15) 0.31176(8) 0.0537(4) Uani 1 1 d . . . . .
C003 C 0.58253(18) 0.44631(18) 0.36375(9) 0.0454(4) Uani 1 1 d . . . . .
C004 C 0.71861(18) 0.52766(18) 0.35157(9) 0.0476(4) Uani 1 1 d . . . . .
C005 C 0.45573(19) 0.53796(18) 0.33390(9) 0.0489(4) Uani 1 1 d . . . . .
C006 C 0.40963(19) 0.26369(17) 0.40590(9) 0.0483(4) Uani 1 1 d . . . . .
C007 C 0.3449(2) 0.16412(19) 0.35768(10) 0.0552(5) Uani 1 1 d . . . . .
H007 H 0.394381 0.135267 0.316981 0.066 Uiso 1 1 calc R U . . .
C008 C 0.56176(19) 0.32040(18) 0.39607(9) 0.0483(4) Uani 1 1 d . . . . .
C009 C 0.6725(2) 0.65722(18) 0.32072(9) 0.0496(4) Uani 1 1 d . . . . .
C00A C 0.8712(2) 0.5046(2) 0.36342(12) 0.0624(5) Uani 1 1 d . . . . .
H00A H 0.906345 0.420274 0.384120 0.075 Uiso 1 1 calc R U . . .
C00B C 0.2073(2) 0.1075(2) 0.36974(13) 0.0684(6) Uani 1 1 d . . . . .
H00B H 0.164898 0.040601 0.337140 0.082 Uiso 1 1 calc R U . . .
C00C C 0.9716(2) 0.6081(3) 0.34420(12) 0.0711(6) Uani 1 1 d . . . . .
H00C H 1.073415 0.591873 0.351950 0.085 Uiso 1 1 calc R U . . .
C00D C 0.3325(2) 0.3050(2) 0.46603(11) 0.0660(5) Uani 1 1 d . . . . .
H00D H 0.374227 0.371487 0.499022 0.079 Uiso 1 1 calc R U . . .
C00E C 0.7719(2) 0.7604(2) 0.30182(11) 0.0631(5) Uani 1 1 d . . . . .
H00E H 0.738285 0.845483 0.281460 0.076 Uiso 1 1 calc R U . . .
C00F C 0.4311(2) 0.7839(2) 0.28633(13) 0.0710(6) Uani 1 1 d . . . . .
H00F H 0.451945 0.805615 0.236367 0.106 Uiso 1 1 calc R U . . .
H00G H 0.457201 0.862939 0.317670 0.106 Uiso 1 1 calc R U . . .
H00H H 0.326954 0.763811 0.288114 0.106 Uiso 1 1 calc R U . . .
C00G C 0.6908(2) 0.2307(2) 0.42826(12) 0.0662(6) Uani 1 1 d . . . . .
H00I H 0.781608 0.270407 0.409933 0.079 Uiso 1 1 calc R U . . .
C00H C 0.1324(2) 0.1494(3) 0.42979(13) 0.0742(6) Uani 1 1 d . . . . .
H00J H 0.040124 0.110709 0.437959 0.089 Uiso 1 1 calc R U . . .
C00I C 0.9219(2) 0.7331(3) 0.31412(12) 0.0715(6) Uani 1 1 d . . . . .
H00K H 0.990574 0.800707 0.301772 0.086 Uiso 1 1 calc R U . . .
C00J C 0.1953(3) 0.2488(3) 0.47734(13) 0.0767(6) Uani 1 1 d . . . . .
H00L H 0.144718 0.278422 0.517531 0.092 Uiso 1 1 calc R U . . .
C00K C 0.6833(3) 0.0803(3) 0.40351(18) 0.1056(9) Uani 1 1 d . . . . .
H00M H 0.672771 0.076680 0.350414 0.158 Uiso 1 1 calc R U . . .
H00N H 0.599220 0.035377 0.423176 0.158 Uiso 1 1 calc R U . . .
H00O H 0.772935 0.032556 0.421059 0.158 Uiso 1 1 calc R U . . .
C00L C 0.7072(5) 0.2418(4) 0.51001(18) 0.1619(19) Uani 1 1 d . . . . .
H00P H 0.728865 0.337506 0.523920 0.243 Uiso 1 1 calc R U . . .
H00Q H 0.787132 0.182119 0.529004 0.243 Uiso 1 1 calc R U . . .
H00R H 0.616276 0.212977 0.530096 0.243 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
O001 C005 1.217(2) . ?
N002 C005 1.379(3) . ?
N002 C009 1.394(3) . ?
N002 C00F 1.449(3) . ?
C003 C008 1.351(3) . ?
C003 C004 1.479(3) . ?
C003 C005 1.505(3) . ?
C004 C00A 1.393(3) . ?
C004 C009 1.403(3) . ?
C006 C007 1.387(3) . ?
C006 C00D 1.391(3) . ?
C006 C008 1.495(3) . ?
C007 C00B 1.383(3) . ?
C007 H007 0.9300 . ?
C008 C00G 1.523(3) . ?
C009 C00E 1.388(3) . ?
C00A C00C 1.397(3) . ?
C00A H00A 0.9300 . ?
C00B C00H 1.380(3) . ?
C00B H00B 0.9300 . ?
C00C C00I 1.368(3) . ?
C00C H00C 0.9300 . ?
C00D C00J 1.375(3) . ?
C00D H00D 0.9300 . ?
C00E C00I 1.378(3) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9600 . ?
C00F H00G 0.9600 . ?
C00F H00H 0.9600 . ?
C00G C00L 1.481(4) . ?
C00G C00K 1.498(4) . ?
C00G H00I 0.9800 . ?
C00H C00J 1.373(3) . ?
C00H H00J 0.9300 . ?
C00I H00K 0.9300 . ?
C00J H00L 0.9300 . ?
C00K H00M 0.9600 . ?
C00K H00N 0.9600 . ?
C00K H00O 0.9600 . ?
C00L H00P 0.9600 . ?
C00L H00Q 0.9600 . ?
C00L H00R 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
C005 N002 C009 110.97(15) . . ?
C005 N002 C00F 123.90(18) . . ?
C009 N002 C00F 125.06(16) . . ?
C008 C003 C004 132.07(16) . . ?
C008 C003 C005 122.88(16) . . ?
C004 C003 C005 105.01(17) . . ?
C00A C004 C009 117.38(17) . . ?
C00A C004 C003 135.53(18) . . ?
C009 C004 C003 107.09(16) . . ?
O001 C005 N002 123.81(16) . . ?
O001 C005 C003 129.36(17) . . ?
N002 C005 C003 106.82(16) . . ?
C007 C006 C00D 118.36(18) . . ?
C007 C006 C008 121.16(16) . . ?
C00D C006 C008 120.42(17) . . ?
C00B C007 C006 120.40(19) . . ?
C00B C007 H007 119.8 . . ?
C006 C007 H007 119.8 . . ?
C003 C008 C006 121.87(15) . . ?
C003 C008 C00G 122.40(17) . . ?
C006 C008 C00G 115.66(17) . . ?
C00E C009 N002 127.24(18) . . ?
C00E C009 C004 122.75(19) . . ?
N002 C009 C004 110.00(15) . . ?
C004 C00A C00C 120.0(2) . . ?
C004 C00A H00A 120.0 . . ?
C00C C00A H00A 120.0 . . ?
C00H C00B C007 120.5(2) . . ?
C00H C00B H00B 119.8 . . ?
C007 C00B H00B 119.8 . . ?
C00I C00C C00A 120.8(2) . . ?
C00I C00C H00C 119.6 . . ?
C00A C00C H00C 119.6 . . ?
C00J C00D C006 120.9(2) . . ?
C00J C00D H00D 119.6 . . ?
C006 C00D H00D 119.6 . . ?
C00I C00E C009 118.0(2) . . ?
C00I C00E H00E 121.0 . . ?
C009 C00E H00E 121.0 . . ?
N002 C00F H00F 109.5 . . ?
N002 C00F H00G 109.5 . . ?
H00F C00F H00G 109.5 . . ?
N002 C00F H00H 109.5 . . ?
H00F C00F H00H 109.5 . . ?
H00G C00F H00H 109.5 . . ?
C00L C00G C00K 111.5(2) . . ?
C00L C00G C008 111.1(2) . . ?
C00K C00G C008 113.75(18) . . ?
C00L C00G H00I 106.7 . . ?
C00K C00G H00I 106.7 . . ?
C008 C00G H00I 106.7 . . ?
C00J C00H C00B 119.4(2) . . ?
C00J C00H H00J 120.3 . . ?
C00B C00H H00J 120.3 . . ?
C00C C00I C00E 121.06(19) . . ?
C00C C00I H00K 119.5 . . ?
C00E C00I H00K 119.5 . . ?
C00H C00J C00D 120.5(2) . . ?
C00H C00J H00L 119.7 . . ?
C00D C00J H00L 119.7 . . ?
C00G C00K H00M 109.5 . . ?
C00G C00K H00N 109.5 . . ?
H00M C00K H00N 109.5 . . ?
C00G C00K H00O 109.5 . . ?
H00M C00K H00O 109.5 . . ?
H00N C00K H00O 109.5 . . ?
C00G C00L H00P 109.5 . . ?
C00G C00L H00Q 109.5 . . ?
H00P C00L H00Q 109.5 . . ?
C00G C00L H00R 109.5 . . ?
H00P C00L H00R 109.5 . . ?
H00Q C00L H00R 109.5 . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.036



####################################################################### 
# 
# 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_SP_DG_325
_database_code_depnum_ccdc_archive 'CCDC 2266989'
loop_
_audit_author_name
_audit_author_address
'Debraj Ghorai'
;IIT Kharagpur
India
;
_audit_update_record             
;
2023-06-01 deposited with the CCDC.	2023-10-23 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            'C27 H34 B N O3'
_chemical_formula_weight         431.36

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'
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.867(3)
_cell_length_b                   11.445(4)
_cell_length_c                   12.457(4)
_cell_angle_alpha                102.292(11)
_cell_angle_beta                 95.249(14)
_cell_angle_gamma                98.197(11)
_cell_volume                     1212.8(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    1154
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      19.18


_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6143
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17144
_diffrn_reflns_av_unetI/netI     0.1208
_diffrn_reflns_av_R_equivalents  0.1311
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.339
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_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             4267
_reflns_number_gt                2295
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'



_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)+(0.0298P)²+0.1530P] 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         4267
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1324
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1658
_refine_ls_wR_factor_gt          0.1336
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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 0.1907(4) 0.5828(3) 0.9760(3) 0.0560(9) Uani 1 1 d . . . . .
H1A H 0.209417 0.529298 1.024817 0.067 Uiso 1 1 calc R U . . .
H1B H 0.103998 0.543530 0.920674 0.067 Uiso 1 1 calc R U . . .
C2 C 0.1623(4) 0.7035(3) 1.0405(3) 0.0679(11) Uani 1 1 d . . . . .
H2A H 0.053607 0.702894 1.044983 0.081 Uiso 1 1 calc R U . . .
H2B H 0.216805 0.723324 1.114921 0.081 Uiso 1 1 calc R U . . .
C3 C 0.2236(4) 0.7923(3) 0.9748(3) 0.0621(10) Uani 1 1 d . . . . .
H3A H 0.148355 0.792703 0.913324 0.074 Uiso 1 1 calc R U . . .
H3B H 0.250097 0.873687 1.021293 0.074 Uiso 1 1 calc R U . . .
C4 C 0.3645(3) 0.7475(2) 0.9337(3) 0.0485(8) Uani 1 1 d . . . . .
H4A H 0.380310 0.765967 0.862690 0.058 Uiso 1 1 calc R U . . .
H4B H 0.455384 0.783278 0.986242 0.058 Uiso 1 1 calc R U . . .
C5 C 0.3966(3) 0.5303(3) 0.8692(2) 0.0402(7) Uani 1 1 d . . . . .
C6 C 0.5363(3) 0.5485(3) 0.8139(2) 0.0377(7) Uani 1 1 d . . . . .
C7 C 0.5585(3) 0.4395(3) 0.7585(2) 0.0402(7) Uani 1 1 d . . . . .
C8 C 0.6846(3) 0.4192(3) 0.6873(2) 0.0437(8) Uani 1 1 d . . . . .
H8A H 0.728107 0.349396 0.699830 0.052 Uiso 1 1 calc R U . . .
H8B H 0.765565 0.489419 0.707003 0.052 Uiso 1 1 calc R U . . .
C9 C 0.6214(3) 0.3979(3) 0.5654(3) 0.0535(9) Uani 1 1 d . . . . .
H9A H 0.542754 0.326068 0.546671 0.064 Uiso 1 1 calc R U . . .
H9B H 0.572487 0.466031 0.555341 0.064 Uiso 1 1 calc R U . . .
C10 C 0.7387(3) 0.3819(3) 0.4856(2) 0.0430(8) Uani 1 1 d . . . . .
C11 C 0.7788(4) 0.4693(3) 0.4277(3) 0.0524(9) Uani 1 1 d . . . . .
H11 H 0.734947 0.539406 0.439669 0.063 Uiso 1 1 calc R U . . .
C12 C 0.8838(4) 0.4541(3) 0.3516(3) 0.0612(10) Uani 1 1 d . . . . .
H12 H 0.909504 0.513273 0.312519 0.073 Uiso 1 1 calc R U . . .
C13 C 0.9497(4) 0.3502(4) 0.3347(3) 0.0635(10) Uani 1 1 d . . . . .
H13 H 1.020973 0.339534 0.284617 0.076 Uiso 1 1 calc R U . . .
C14 C 0.9097(4) 0.2635(3) 0.3915(3) 0.0662(11) Uani 1 1 d . . . . .
H14 H 0.952913 0.193110 0.379431 0.079 Uiso 1 1 calc R U . . .
C15 C 0.8058(4) 0.2796(3) 0.4667(3) 0.0607(10) Uani 1 1 d . . . . .
H15 H 0.780541 0.220023 0.505541 0.073 Uiso 1 1 calc R U . . .
C16 C 0.6347(3) 0.6683(2) 0.8214(2) 0.0384(7) Uani 1 1 d . . . . .
C17 C 0.7300(3) 0.7285(3) 0.9180(3) 0.0459(8) Uani 1 1 d . . . . .
H17 H 0.730502 0.695682 0.980146 0.055 Uiso 1 1 calc R U . . .
C18 C 0.8244(4) 0.8377(3) 0.9221(3) 0.0569(9) Uani 1 1 d . . . . .
H18 H 0.888465 0.877058 0.986862 0.068 Uiso 1 1 calc R U . . .
C19 C 0.8240(4) 0.8876(3) 0.8320(4) 0.0626(10) Uani 1 1 d . . . . .
H19 H 0.887358 0.960816 0.835651 0.075 Uiso 1 1 calc R U . . .
C20 C 0.7306(4) 0.8302(3) 0.7362(3) 0.0627(10) Uani 1 1 d . . . . .
H20 H 0.729862 0.864565 0.674930 0.075 Uiso 1 1 calc R U . . .
C21 C 0.6370(4) 0.7205(3) 0.7308(3) 0.0502(9) Uani 1 1 d . . . . .
H21 H 0.574774 0.681376 0.665186 0.060 Uiso 1 1 calc R U . . .
C22 C 0.3980(4) 0.1227(3) 0.7428(3) 0.0500(9) Uani 1 1 d . . . . .
C23 C 0.3538(5) 0.0278(3) 0.8093(3) 0.0733(12) Uani 1 1 d . . . . .
H23A H 0.444574 0.014082 0.849704 0.110 Uiso 1 1 calc R U . . .
H23B H 0.304113 -0.046672 0.759688 0.110 Uiso 1 1 calc R U . . .
H23C H 0.284995 0.056492 0.860223 0.110 Uiso 1 1 calc R U . . .
C24 C 0.5205(4) 0.0828(3) 0.6718(3) 0.0701(11) Uani 1 1 d . . . . .
H24A H 0.544516 0.139533 0.626608 0.105 Uiso 1 1 calc R U . . .
H24B H 0.482862 0.003765 0.625143 0.105 Uiso 1 1 calc R U . . .
H24C H 0.611294 0.079930 0.718748 0.105 Uiso 1 1 calc R U . . .
C25 C 0.2618(4) 0.1574(3) 0.6760(3) 0.0467(8) Uani 1 1 d . . . . .
C26 C 0.1182(4) 0.1592(3) 0.7348(3) 0.0742(12) Uani 1 1 d . . . . .
H26A H 0.145184 0.206525 0.809369 0.111 Uiso 1 1 calc R U . . .
H26B H 0.074630 0.077794 0.735930 0.111 Uiso 1 1 calc R U . . .
H26C H 0.044603 0.194394 0.696070 0.111 Uiso 1 1 calc R U . . .
C27 C 0.2189(4) 0.0826(3) 0.5571(3) 0.0694(11) Uani 1 1 d . . . . .
H27A H 0.138111 0.113374 0.520831 0.104 Uiso 1 1 calc R U . . .
H27B H 0.184478 -0.000583 0.557881 0.104 Uiso 1 1 calc R U . . .
H27C H 0.307064 0.088135 0.518027 0.104 Uiso 1 1 calc R U . . .
N1 N 0.3287(3) 0.6151(2) 0.9235(2) 0.0426(6) Uani 1 1 d . . . . .
O1 O 0.4630(2) 0.23583(17) 0.81877(17) 0.0493(6) Uani 1 1 d . . . . .
O2 O 0.3202(2) 0.28034(16) 0.67162(17) 0.0450(6) Uani 1 1 d . . . . .
O3 O 0.3381(2) 0.41810(17) 0.85896(17) 0.0474(6) Uani 1 1 d . . . . .
B1 B 0.4241(4) 0.3336(3) 0.7709(3) 0.0418(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.477(4) . ?
C1 C2 1.510(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.509(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.508(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.479(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O3 1.289(3) . ?
C5 N1 1.313(4) . ?
C5 C6 1.482(4) . ?
C6 C7 1.342(4) . ?
C6 C16 1.496(4) . ?
C7 C8 1.503(4) . ?
C7 B1 1.617(4) . ?
C8 C9 1.525(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.506(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.374(4) . ?
C10 C11 1.379(4) . ?
C11 C12 1.390(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.362(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.385(4) . ?
C16 C17 1.390(4) . ?
C17 C18 1.390(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.363(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.388(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 O1 1.439(3) . ?
C22 C24 1.522(5) . ?
C22 C23 1.529(4) . ?
C22 C25 1.549(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O2 1.443(3) . ?
C25 C26 1.526(5) . ?
C25 C27 1.528(4) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
O1 B1 1.444(4) . ?
O2 B1 1.436(4) . ?
O3 B1 1.622(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 103.7(2) . . ?
N1 C1 H1A 111.0 . . ?
C2 C1 H1A 111.0 . . ?
N1 C1 H1B 111.0 . . ?
C2 C1 H1B 111.0 . . ?
H1A C1 H1B 109.0 . . ?
C3 C2 C1 103.9(3) . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C4 C3 C2 104.6(3) . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
N1 C4 C3 103.3(2) . . ?
N1 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
N1 C4 H4B 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
O3 C5 N1 119.0(3) . . ?
O3 C5 C6 114.2(3) . . ?
N1 C5 C6 126.8(3) . . ?
C7 C6 C5 107.9(2) . . ?
C7 C6 C16 126.9(3) . . ?
C5 C6 C16 125.2(3) . . ?
C6 C7 C8 124.6(3) . . ?
C6 C7 B1 111.0(3) . . ?
C8 C7 B1 124.3(3) . . ?
C7 C8 C9 110.0(2) . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C8 115.1(3) . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C8 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C15 C10 C11 118.3(3) . . ?
C15 C10 C9 121.3(3) . . ?
C11 C10 C9 120.3(3) . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 121.3(3) . . ?
C10 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C21 C16 C17 118.0(3) . . ?
C21 C16 C6 120.8(3) . . ?
C17 C16 C6 121.2(3) . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 119.7(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C16 C21 C20 121.2(3) . . ?
C16 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
O1 C22 C24 108.0(3) . . ?
O1 C22 C23 108.7(3) . . ?
C24 C22 C23 109.0(3) . . ?
O1 C22 C25 102.5(2) . . ?
C24 C22 C25 112.9(3) . . ?
C23 C22 C25 115.3(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O2 C25 C26 107.9(3) . . ?
O2 C25 C27 107.9(3) . . ?
C26 C25 C27 109.5(3) . . ?
O2 C25 C22 102.4(2) . . ?
C26 C25 C22 113.4(3) . . ?
C27 C25 C22 115.2(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C5 N1 C1 120.6(2) . . ?
C5 N1 C4 128.0(2) . . ?
C1 N1 C4 111.2(2) . . ?
C22 O1 B1 108.5(2) . . ?
B1 O2 C25 107.4(2) . . ?
C5 O3 B1 109.1(2) . . ?
O2 B1 O1 107.3(2) . . ?
O2 B1 C7 114.5(3) . . ?
O1 B1 C7 119.7(3) . . ?
O2 B1 O3 109.6(3) . . ?
O1 B1 O3 107.8(2) . . ?
C7 B1 O3 97.1(2) . . ?

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
N1 C1 C2 C3 29.7(4) . . . . ?
C1 C2 C3 C4 -37.3(4) . . . . ?
C2 C3 C4 N1 29.4(3) . . . . ?
O3 C5 C6 C7 4.9(4) . . . . ?
N1 C5 C6 C7 -173.7(3) . . . . ?
O3 C5 C6 C16 -174.1(3) . . . . ?
N1 C5 C6 C16 7.3(5) . . . . ?
C5 C6 C7 C8 177.2(3) . . . . ?
C16 C6 C7 C8 -3.7(5) . . . . ?
C5 C6 C7 B1 1.5(3) . . . . ?
C16 C6 C7 B1 -179.4(3) . . . . ?
C6 C7 C8 C9 -101.0(3) . . . . ?
B1 C7 C8 C9 74.1(4) . . . . ?
C7 C8 C9 C10 177.4(3) . . . . ?
C8 C9 C10 C15 70.3(4) . . . . ?
C8 C9 C10 C11 -111.1(3) . . . . ?
C15 C10 C11 C12 0.3(5) . . . . ?
C9 C10 C11 C12 -178.2(3) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
C12 C13 C14 C15 -0.9(6) . . . . ?
C11 C10 C15 C14 -0.4(5) . . . . ?
C9 C10 C15 C14 178.1(3) . . . . ?
C13 C14 C15 C10 0.7(6) . . . . ?
C7 C6 C16 C21 71.5(4) . . . . ?
C5 C6 C16 C21 -109.6(3) . . . . ?
C7 C6 C16 C17 -106.4(4) . . . . ?
C5 C6 C16 C17 72.4(4) . . . . ?
C21 C16 C17 C18 -0.2(4) . . . . ?
C6 C16 C17 C18 177.8(3) . . . . ?
C16 C17 C18 C19 0.6(5) . . . . ?
C17 C18 C19 C20 -0.2(5) . . . . ?
C18 C19 C20 C21 -0.5(5) . . . . ?
C17 C16 C21 C20 -0.5(4) . . . . ?
C6 C16 C21 C20 -178.5(3) . . . . ?
C19 C20 C21 C16 0.8(5) . . . . ?
O1 C22 C25 O2 33.9(3) . . . . ?
C24 C22 C25 O2 -82.0(3) . . . . ?
C23 C22 C25 O2 151.8(3) . . . . ?
O1 C22 C25 C26 -82.1(3) . . . . ?
C24 C22 C25 C26 162.0(3) . . . . ?
C23 C22 C25 C26 35.8(4) . . . . ?
O1 C22 C25 C27 150.7(2) . . . . ?
C24 C22 C25 C27 34.8(4) . . . . ?
C23 C22 C25 C27 -91.4(3) . . . . ?
O3 C5 N1 C1 2.4(4) . . . . ?
C6 C5 N1 C1 -179.1(3) . . . . ?
O3 C5 N1 C4 -172.0(3) . . . . ?
C6 C5 N1 C4 6.5(5) . . . . ?
C2 C1 N1 C5 173.0(3) . . . . ?
C2 C1 N1 C4 -11.7(4) . . . . ?
C3 C4 N1 C5 163.9(3) . . . . ?
C3 C4 N1 C1 -11.0(3) . . . . ?
C24 C22 O1 B1 94.5(3) . . . . ?
C23 C22 O1 B1 -147.4(3) . . . . ?
C25 C22 O1 B1 -24.9(3) . . . . ?
C26 C25 O2 B1 89.0(3) . . . . ?
C27 C25 O2 B1 -152.8(3) . . . . ?
C22 C25 O2 B1 -30.9(3) . . . . ?
N1 C5 O3 B1 169.8(3) . . . . ?
C6 C5 O3 B1 -8.9(3) . . . . ?
C25 O2 B1 O1 16.4(3) . . . . ?
C25 O2 B1 C7 151.9(2) . . . . ?
C25 O2 B1 O3 -100.4(2) . . . . ?
C22 O1 B1 O2 6.6(3) . . . . ?
C22 O1 B1 C7 -126.1(3) . . . . ?
C22 O1 B1 O3 124.6(2) . . . . ?
C6 C7 B1 O2 109.5(3) . . . . ?
C8 C7 B1 O2 -66.2(4) . . . . ?
C6 C7 B1 O1 -121.0(3) . . . . ?
C8 C7 B1 O1 63.3(4) . . . . ?
C6 C7 B1 O3 -5.8(3) . . . . ?
C8 C7 B1 O3 178.5(3) . . . . ?
C5 O3 B1 O2 -110.5(3) . . . . ?
C5 O3 B1 O1 133.0(3) . . . . ?
C5 O3 B1 C7 8.6(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
_geom_hbond_publ_flag
C4 H4B O1 0.97 2.53 3.269(4) 132.6 2_667 yes

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.044



