# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1442
_database_code_depnum_ccdc_archive 'CCDC 2243707'
loop_
_audit_author_name
_audit_author_address
'Dr. Shobhana Krishnaswamy'
;IIT MADRAS
India
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-10-11 downloaded from the CCDC.
;
_audit_creation_date             2023-02-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_formula_moiety         'C18 N O4'
_chemical_formula_sum            'C18 N O4'
_chemical_formula_weight         317.388
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           ' P 2c -2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,z+1/2
3 -x+1/2,y+1/2,z+1/2
4 x+1/2,-y+1/2,z

_symmetry_Int_Tables_number      33
_cell_length_a                   12.2934(5)
_cell_length_b                   14.3475(5)
_cell_length_c                   9.7444(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1718.71(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5048
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.08
_cell_measurement_theta_min      2.53
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       Block
_exptl_crystal_F_000             680.459
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 1.0000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11670
_diffrn_reflns_point_group_measured_fraction_full 0.9964
_diffrn_reflns_point_group_measured_fraction_max 0.9964
_diffrn_reflns_theta_full        24.9916
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.18
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.992
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              17
_reflns_limit_k_min              -16
_reflns_limit_l_max              11
_reflns_limit_l_min              -11
_reflns_number_gt                2591
_reflns_number_total             3028
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.4459
_refine_diff_density_min         -0.2402
_refine_diff_density_rms         0.0643
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_d_res_high            0.8411
_refine_ls_d_res_low             9.3353
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.6691
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3028
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0672
_refine_ls_restrained_S_all      1.6691
_refine_ls_shift/su_max          0.1093
_refine_ls_shift/su_mean         0.0175
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0609P)²+0.2627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1701
_refine_ls_wR_factor_ref         0.1746
_olex2_refinement_description    
;
;
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_refinement_flags_posn
C1 C 0.4379(3) 0.4496(3) 0.0713(5) 0.0592(9) Uani 1.000000 .
C2 C 0.5395(3) 0.4358(3) 0.1308(5) 0.0718(12) Uani 1.000000 .
C3 C 0.5487(4) 0.3990(4) 0.2616(5) 0.0779(14) Uani 1.000000 .
C4 C 0.4536(4) 0.3748(4) 0.3316(5) 0.0759(13) Uani 1.000000 .
C5 C 0.3534(3) 0.3883(3) 0.2714(4) 0.0614(10) Uani 1.000000 .
C6 C 0.3453(3) 0.4264(2) 0.1421(4) 0.0470(8) Uani 1.000000 .
C7 C 0.2378(3) 0.4433(2) 0.0726(4) 0.0455(8) Uani 1.000000 .
C8 C 0.1337(3) 0.4072(2) 0.1383(4) 0.0484(8) Uani 1.000000 .
C9 C 0.0365(3) 0.4063(3) 0.0433(4) 0.0542(10) Uani 1.000000 .
C10 C -0.0465(3) 0.3287(3) 0.0719(6) 0.0805(14) Uani 1.000000 .
C11 C -0.1253(5) 0.3694(4) 0.1679(7) 0.107(2) Uani 1.000000 .
C12 C -0.1378(3) 0.4702(3) 0.1252(6) 0.0782(14) Uani 1.000000 .
C13 C -0.0228(3) 0.4986(2) 0.0743(4) 0.0497(8) Uani 1.000000 .
C14 C 0.0977(3) 0.6252(2) 0.1485(4) 0.0463(8) Uani 1.000000 .
C15 C 0.2594(4) 0.7164(3) 0.2040(4) 0.0669(12) Uani 1.000000 .
C16 C 0.1935(5) 0.8042(3) 0.2461(7) 0.108(2) Uani 1.000000 .
C17 C 0.2972(4) 0.7221(4) 0.0567(5) 0.0856(15) Uani 1.000000 .
C18 C 0.3535(5) 0.6934(5) 0.3009(7) 0.115(2) Uani 1.000000 .
N1 N 0.0428(2) 0.54204(18) 0.1819(3) 0.0446(7) Uani 1.000000 .
O1 O 0.2335(2) 0.4879(2) -0.0331(3) 0.0626(7) Uani 1.000000 .
O2 O 0.10577(19) 0.47219(15) 0.2471(2) 0.0479(6) Uani 1.000000 .
O3 O 0.0596(2) 0.68039(18) 0.0708(4) 0.0717(9) Uani 1.000000 .
O4 O 0.1889(2) 0.63352(17) 0.2216(3) 0.0550(7) Uani 1.000000 .


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 1.391(6) . ?
C1 C6 1.372(5) . ?
C2 C3 1.384(7) . ?
C3 C4 1.397(7) . ?
C4 C5 1.379(6) . ?
C5 C6 1.378(5) . ?
C6 C7 1.505(5) . ?
C7 C8 1.522(5) . ?
C7 O1 1.214(4) . ?
C8 C9 1.512(5) . ?
C8 O2 1.453(4) . ?
C9 C10 1.536(6) . ?
C9 C13 1.541(5) . ?
C10 C11 1.467(8) . ?
C11 C12 1.513(8) . ?
C12 C13 1.553(5) . ?
C13 N1 1.463(5) . ?
C14 N1 1.409(4) . ?
C14 O3 1.191(5) . ?
C14 O4 1.333(4) . ?
C15 C16 1.554(7) . ?
C15 C17 1.511(7) . ?
C15 C18 1.529(8) . ?
C15 O4 1.481(4) . ?
N1 O2 1.417(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
C6 C1 C2 120.1(4) . . ?
C3 C2 C1 120.8(4) . . ?
C4 C3 C2 118.4(4) . . ?
C5 C4 C3 120.4(4) . . ?
C6 C5 C4 120.6(4) . . ?
C5 C6 C1 119.8(4) . . ?
C7 C6 C1 117.6(3) . . ?
C7 C6 C5 122.6(3) . . ?
C8 C7 C6 119.7(3) . . ?
O1 C7 C6 120.3(3) . . ?
O1 C7 C8 120.0(3) . . ?
C9 C8 C7 114.2(3) . . ?
O2 C8 C7 106.7(3) . . ?
O2 C8 C9 105.4(3) . . ?
C10 C9 C8 114.9(4) . . ?
C13 C9 C8 104.3(3) . . ?
C13 C9 C10 105.9(3) . . ?
C11 C10 C9 105.4(3) . . ?
C12 C11 C10 105.8(4) . . ?
C13 C12 C11 104.2(4) . . ?
C12 C13 C9 105.5(3) . . ?
N1 C13 C9 104.2(3) . . ?
N1 C13 C12 112.7(3) . . ?
O3 C14 N1 121.4(3) . . ?
O4 C14 N1 110.8(3) . . ?
O4 C14 O3 127.7(3) . . ?
C17 C15 C16 111.5(5) . . ?
C18 C15 C16 114.0(5) . . ?
C18 C15 C17 111.4(4) . . ?
O4 C15 C16 108.4(3) . . ?
O4 C15 C17 109.5(3) . . ?
O4 C15 C18 101.4(4) . . ?
C14 N1 C13 117.4(3) . . ?
O2 N1 C13 108.8(2) . . ?
O2 N1 C14 116.2(2) . . ?
N1 O2 C8 104.8(2) . . ?
C15 O4 C14 120.1(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
C1 C2 C3 C4 1.0(6) . . . . ?
C1 C6 C5 C4 1.2(5) . . . . ?
C1 C6 C7 C8 172.0(3) . . . . ?
C1 C6 C7 O1 -10.3(4) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
C4 C5 C6 C7 -179.5(4) . . . . ?
C5 C6 C7 C8 -7.3(4) . . . . ?
C5 C6 C7 O1 170.4(4) . . . . ?
C6 C7 C8 C9 -165.0(3) . . . . ?
C6 C7 C8 O2 78.9(3) . . . . ?
C7 C8 C9 C10 149.0(3) . . . . ?
C7 C8 C9 C13 -95.6(3) . . . . ?
C7 C8 O2 N1 87.3(3) . . . . ?
C8 C9 C10 C11 91.1(5) . . . . ?
C8 C9 C13 C12 -119.5(3) . . . . ?
C8 C9 C13 N1 -0.7(3) . . . . ?
C8 O2 N1 C13 35.2(3) . . . . ?
C8 O2 N1 C14 -99.9(2) . . . . ?
C9 C10 C11 C12 36.3(4) . . . . ?
C9 C13 C12 C11 19.3(4) . . . . ?
C9 C13 N1 C14 113.5(3) . . . . ?
C9 C13 N1 O2 -21.0(3) . . . . ?
C10 C11 C12 C13 -34.7(5) . . . . ?
C11 C12 C13 N1 -93.8(4) . . . . ?
C12 C13 N1 C14 -132.6(3) . . . . ?
C12 C13 N1 O2 92.9(3) . . . . ?
C13 N1 C14 O3 33.9(3) . . . . ?
C13 N1 C14 O4 -150.4(3) . . . . ?
C14 O4 C15 C16 62.2(4) . . . . ?
C14 O4 C15 C17 -59.7(4) . . . . ?
C14 O4 C15 C18 -177.6(4) . . . . ?


_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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2245191'
loop_
_audit_author_name
_audit_author_address
'Dr. Shobhana Krishnaswamy'
;IIT MADRAS
India
;
_audit_update_record             
;
2023-02-28 deposited with the CCDC.	2023-10-11 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            'C19 H27 N O4'
_chemical_formula_weight         333.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   26.239(5)
_cell_length_b                   14.599(3)
_cell_length_c                   10.4681(18)
_cell_angle_alpha                90
_cell_angle_beta                 112.952(8)
_cell_angle_gamma                90
_cell_volume                     3692.3(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9696
_cell_measurement_theta_min      3.54
_cell_measurement_theta_max      67.93

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.112
_exptl_absorpt_coefficient_mu    0.675
_shelx_estimated_absorpt_T_min   0.873
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6279
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50618
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.537
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3387
_reflns_number_gt                2724
_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, 2012)'
_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)+(0.0706P)²+1.3513P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00084(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3387
_refine_ls_number_parameters     235
_refine_ls_number_restraints     52
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1419
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.091
_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 0.50048(9) 0.6243(2) 1.0225(4) 0.1326(12) Uani 1 1 d . . . . .
H1A H 0.506655 0.607368 1.115985 0.199 Uiso 1 1 calc R U . . .
H1B H 0.509485 0.687792 1.019729 0.199 Uiso 1 1 calc R U . . .
H1C H 0.523480 0.587558 0.990459 0.199 Uiso 1 1 calc R U . . .
C2 C 0.44028(8) 0.60870(14) 0.9299(3) 0.0917(7) Uani 1 1 d . . . . .
C3 C 0.42097(10) 0.62080(17) 0.7884(3) 0.0976(8) Uani 1 1 d . . . . .
H3 H 0.445723 0.637724 0.748748 0.117 Uiso 1 1 calc R U . . .
C4 C 0.36605(9) 0.60856(15) 0.7039(3) 0.0841(6) Uani 1 1 d . . . . .
H4 H 0.354268 0.617854 0.608808 0.101 Uiso 1 1 calc R U . . .
C5 C 0.32826(7) 0.58254(11) 0.7594(2) 0.0637(4) Uani 1 1 d . . . . .
C6 C 0.34721(8) 0.56862(13) 0.9006(2) 0.0748(5) Uani 1 1 d . . . . .
H6 H 0.322644 0.549903 0.939780 0.090 Uiso 1 1 calc R U . . .
C7 C 0.40238(9) 0.58217(15) 0.9847(3) 0.0879(6) Uani 1 1 d . . . . .
H7 H 0.414194 0.573272 1.079925 0.105 Uiso 1 1 calc R U . . .
C8 C 0.26814(7) 0.57175(12) 0.66717(18) 0.0637(4) Uani 1 1 d . . . . .
H8 H 0.250847 0.529510 0.711101 0.076 Uiso 1 1 calc R U . . .
C9 C 0.23784(7) 0.66417(11) 0.64275(16) 0.0606(4) Uani 1 1 d . . . . .
H9 H 0.261343 0.711217 0.626786 0.073 Uiso 1 1 calc R U . . .
C10 C 0.22083(7) 0.69567(12) 0.75841(17) 0.0619(4) Uani 1 1 d . U . . .
H10 H 0.245652 0.670844 0.848113 0.074 Uiso 1 1 calc R U . . .
C11 C 0.21393(9) 0.80052(14) 0.7667(3) 0.0931(7) Uani 1 1 d D U . . .
H11A H 0.233447 0.832865 0.718529 0.112 Uiso 1 1 calc R U . A 1
H11B H 0.227985 0.820868 0.862481 0.112 Uiso 1 1 calc R U . A 1
C12 C 0.15000(16) 0.8173(2) 0.6944(6) 0.0854(14) Uani 0.645(8) 1 d D U P B 1
H12A H 0.139202 0.870621 0.733217 0.102 Uiso 0.645(8) 1 calc R U P B 1
H12B H 0.138934 0.826384 0.595395 0.102 Uiso 0.645(8) 1 calc R U P B 1
C12' C 0.1651(3) 0.8092(4) 0.8045(11) 0.079(2) Uani 0.355(8) 1 d D U P B 2
H12C H 0.175359 0.798270 0.902822 0.094 Uiso 0.355(8) 1 calc R U P B 2
H12D H 0.148751 0.869719 0.781751 0.094 Uiso 0.355(8) 1 calc R U P B 2
C13 C 0.12622(8) 0.73830(14) 0.7208(3) 0.0899(7) Uani 1 1 d D U . . .
H13A H 0.088854 0.731229 0.651875 0.108 Uiso 1 1 calc R U . B 1
H13B H 0.124505 0.742189 0.811547 0.108 Uiso 1 1 calc R U . B 1
C14 C 0.16131(7) 0.65711(11) 0.71558(17) 0.0600(4) Uani 1 1 d . U . . .
H14 H 0.159966 0.608107 0.778174 0.072 Uiso 1 1 calc R U . . .
C15 C 0.13540(7) 0.53202(12) 0.53771(16) 0.0623(4) Uani 1 1 d . . . . .
C16 C 0.08627(7) 0.40128(11) 0.58092(18) 0.0641(4) Uani 1 1 d . . . . .
C17 C 0.05163(9) 0.39356(15) 0.6663(2) 0.0864(6) Uani 1 1 d . . . . .
H17A H 0.073543 0.410164 0.760631 0.130 Uiso 1 1 calc R U . . .
H17B H 0.038885 0.331639 0.663224 0.130 Uiso 1 1 calc R U . . .
H17C H 0.020400 0.433956 0.629434 0.130 Uiso 1 1 calc R U . . .
C18 C 0.05186(9) 0.37950(15) 0.4298(2) 0.0857(6) Uani 1 1 d . . . . .
H18A H 0.019569 0.417809 0.397082 0.128 Uiso 1 1 calc R U . . .
H18B H 0.040795 0.316362 0.421286 0.128 Uiso 1 1 calc R U . . .
H18C H 0.073452 0.390552 0.375485 0.128 Uiso 1 1 calc R U . . .
C19 C 0.13800(9) 0.34377(15) 0.6413(2) 0.0848(6) Uani 1 1 d . . . . .
H19A H 0.158769 0.348730 0.583693 0.127 Uiso 1 1 calc R U . . .
H19B H 0.127980 0.280925 0.645446 0.127 Uiso 1 1 calc R U . . .
H19C H 0.160141 0.365057 0.733017 0.127 Uiso 1 1 calc R U . . .
N1 N 0.14723(6) 0.62274(9) 0.57350(13) 0.0617(4) Uani 1 1 d . . . . .
O1 O 0.26405(7) 0.53428(11) 0.53815(16) 0.0897(5) Uani 1 1 d . . . . .
H1D H 0.2257(14) 0.526(2) 0.490(3) 0.135 Uiso 1 1 d . U . . .
O2 O 0.18600(5) 0.66001(9) 0.52334(11) 0.0689(4) Uani 1 1 d . . . . .
O3 O 0.15112(6) 0.49116(10) 0.45857(13) 0.0800(4) Uani 1 1 d . . . . .
O4 O 0.10142(5) 0.50003(8) 0.59406(12) 0.0663(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.514(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.377(4) . ?
C2 C7 1.384(3) . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(3) . ?
C5 C8 1.503(2) . ?
C6 C7 1.384(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O1 1.422(2) . ?
C8 C9 1.536(2) . ?
C8 H8 0.9800 . ?
C9 O2 1.446(2) . ?
C9 C10 1.516(2) . ?
C9 H9 0.9800 . ?
C10 C11 1.548(3) . ?
C10 C14 1.553(2) . ?
C10 H10 0.9800 . ?
C11 C12' 1.487(6) . ?
C11 C12 1.567(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.390(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12' C13 1.477(6) . ?
C12' H12C 0.9700 . ?
C12' H12D 0.9700 . ?
C13 C14 1.515(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N1 1.474(2) . ?
C14 H14 0.9800 . ?
C15 O3 1.216(2) . ?
C15 O4 1.331(2) . ?
C15 N1 1.378(2) . ?
C16 O4 1.487(2) . ?
C16 C17 1.507(3) . ?
C16 C19 1.509(3) . ?
C16 C18 1.518(3) . ?
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 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N1 O2 1.4224(18) . ?
O1 H1D 0.94(3) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 117.4(2) . . ?
C3 C2 C1 121.6(3) . . ?
C7 C2 C1 121.0(3) . . ?
C2 C3 C4 121.9(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 118.22(19) . . ?
C6 C5 C8 121.55(15) . . ?
C4 C5 C8 120.22(18) . . ?
C5 C6 C7 120.79(19) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C2 C7 C6 121.2(2) . . ?
C2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
O1 C8 C5 108.81(14) . . ?
O1 C8 C9 109.72(15) . . ?
C5 C8 C9 111.13(14) . . ?
O1 C8 H8 109.1 . . ?
C5 C8 H8 109.1 . . ?
C9 C8 H8 109.1 . . ?
O2 C9 C10 103.45(13) . . ?
O2 C9 C8 111.00(13) . . ?
C10 C9 C8 115.34(14) . . ?
O2 C9 H9 108.9 . . ?
C10 C9 H9 108.9 . . ?
C8 C9 H9 108.9 . . ?
C9 C10 C11 114.97(16) . . ?
C9 C10 C14 103.63(13) . . ?
C11 C10 C14 104.38(13) . . ?
C9 C10 H10 111.1 . . ?
C11 C10 H10 111.1 . . ?
C14 C10 H10 111.1 . . ?
C12' C11 C10 103.4(3) . . ?
C10 C11 C12 104.71(18) . . ?
C10 C11 H11A 110.8 . . ?
C12 C11 H11A 110.8 . . ?
C10 C11 H11B 110.8 . . ?
C12 C11 H11B 110.8 . . ?
H11A C11 H11B 108.9 . . ?
C13 C12 C11 104.7(3) . . ?
C13 C12 H12A 110.8 . . ?
C11 C12 H12A 110.8 . . ?
C13 C12 H12B 110.8 . . ?
C11 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
C13 C12' C11 104.5(4) . . ?
C13 C12' H12C 110.9 . . ?
C11 C12' H12C 110.9 . . ?
C13 C12' H12D 110.9 . . ?
C11 C12' H12D 110.9 . . ?
H12C C12' H12D 108.9 . . ?
C12 C13 C14 108.4(2) . . ?
C12' C13 C14 106.3(3) . . ?
C12 C13 H13A 110.0 . . ?
C14 C13 H13A 110.0 . . ?
C12 C13 H13B 110.0 . . ?
C14 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
N1 C14 C13 112.71(16) . . ?
N1 C14 C10 104.07(13) . . ?
C13 C14 C10 105.24(14) . . ?
N1 C14 H14 111.5 . . ?
C13 C14 H14 111.5 . . ?
C10 C14 H14 111.5 . . ?
O3 C15 O4 126.41(16) . . ?
O3 C15 N1 123.80(17) . . ?
O4 C15 N1 109.60(14) . . ?
O4 C16 C17 102.64(14) . . ?
O4 C16 C19 109.65(15) . . ?
C17 C16 C19 111.23(17) . . ?
O4 C16 C18 109.17(14) . . ?
C17 C16 C18 110.55(17) . . ?
C19 C16 C18 113.08(17) . . ?
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 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 N1 O2 112.63(14) . . ?
C15 N1 C14 122.87(13) . . ?
O2 N1 C14 107.96(12) . . ?
C8 O1 H1D 103.4(19) . . ?
N1 O2 C9 105.31(11) . . ?
C15 O4 C16 120.01(14) . . ?

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 C2 C3 C4 1.0(3) . . . . ?
C1 C2 C3 C4 -178.6(2) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C3 C4 C5 C8 178.36(18) . . . . ?
C4 C5 C6 C7 1.3(3) . . . . ?
C8 C5 C6 C7 -177.58(17) . . . . ?
C3 C2 C7 C6 -0.2(3) . . . . ?
C1 C2 C7 C6 179.4(2) . . . . ?
C5 C6 C7 C2 -1.0(3) . . . . ?
C6 C5 C8 O1 -144.30(17) . . . . ?
C4 C5 C8 O1 36.8(2) . . . . ?
C6 C5 C8 C9 94.78(19) . . . . ?
C4 C5 C8 C9 -84.07(19) . . . . ?
O1 C8 C9 O2 41.77(18) . . . . ?
C5 C8 C9 O2 162.15(13) . . . . ?
O1 C8 C9 C10 158.99(14) . . . . ?
C5 C8 C9 C10 -80.63(18) . . . . ?
O2 C9 C10 C11 -83.54(17) . . . . ?
C8 C9 C10 C11 155.06(15) . . . . ?
O2 C9 C10 C14 29.71(16) . . . . ?
C8 C9 C10 C14 -91.68(16) . . . . ?
C9 C10 C11 C12' 141.9(4) . . . . ?
C14 C10 C11 C12' 29.0(4) . . . . ?
C9 C10 C11 C12 99.7(3) . . . . ?
C14 C10 C11 C12 -13.1(3) . . . . ?
C10 C11 C12 C13 30.9(4) . . . . ?
C10 C11 C12' C13 -40.6(6) . . . . ?
C11 C12 C13 C14 -36.7(4) . . . . ?
C11 C12' C13 C14 36.6(6) . . . . ?
C12 C13 C14 N1 -84.4(3) . . . . ?
C12' C13 C14 N1 -130.3(4) . . . . ?
C12 C13 C14 C10 28.3(3) . . . . ?
C12' C13 C14 C10 -17.5(4) . . . . ?
C9 C10 C14 N1 -9.21(16) . . . . ?
C11 C10 C14 N1 111.49(16) . . . . ?
C9 C10 C14 C13 -127.95(16) . . . . ?
C11 C10 C14 C13 -7.2(2) . . . . ?
O3 C15 N1 O2 -8.1(2) . . . . ?
O4 C15 N1 O2 176.57(12) . . . . ?
O3 C15 N1 C14 -139.98(17) . . . . ?
O4 C15 N1 C14 44.7(2) . . . . ?
C13 C14 N1 C15 -127.95(17) . . . . ?
C10 C14 N1 C15 118.55(17) . . . . ?
C13 C14 N1 O2 98.34(16) . . . . ?
C10 C14 N1 O2 -15.16(16) . . . . ?
C15 N1 O2 C9 -103.64(14) . . . . ?
C14 N1 O2 C9 35.23(16) . . . . ?
C10 C9 O2 N1 -40.25(15) . . . . ?
C8 C9 O2 N1 84.02(15) . . . . ?
O3 C15 O4 C16 10.2(2) . . . . ?
N1 C15 O4 C16 -174.71(13) . . . . ?
C17 C16 O4 C15 175.98(15) . . . . ?
C19 C16 O4 C15 57.7(2) . . . . ?
C18 C16 O4 C15 -66.7(2) . . . . ?

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
C14 H14 O3 0.98 2.46 3.429(2) 168.9 6_566 yes
C18 H18C O3 0.96 2.38 2.986(3) 120.4 . yes
C19 H19A O3 0.96 2.42 2.987(3) 117.1 . yes
O1 H1D O3 0.94(3) 1.92(3) 2.819(2) 158(3) . yes

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.032



