# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_mo_C20VB158_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2267801'
loop_
_audit_author_name
_audit_author_address
'Merce Font-Bardia' 'universitat de barcelona'
_audit_update_record             
;
2023-06-06 deposited with the CCDC.	2023-07-21 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         'C15 H13 N O5'
_chemical_formula_sum            'C15 H13 N O5'
_chemical_formula_weight         287.26

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'
O O 0.0106 0.0060 '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'

_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                   7.4176(5)
_cell_length_b                   7.5344(5)
_cell_length_c                   13.4049(9)
_cell_angle_alpha                94.585(2)
_cell_angle_beta                 101.837(2)
_cell_angle_gamma                115.880(2)
_cell_volume                     647.36(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9858
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      30.52

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.078
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7246
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34534
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_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         3.062
_diffrn_reflns_theta_max         30.571
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3980
_reflns_number_gt                3380
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0668P)²+0.1850P] 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         3980
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1154
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
O1 O 0.25197(11) 0.49759(11) 0.61464(5) 0.01586(16) Uani 1 1 d . . . . .
H1O H 0.323273 0.567738 0.577931 0.019 Uiso 1 1 calc R U . . .
N1 N 0.45711(13) 0.69762(13) 0.48906(7) 0.01443(17) Uani 1 1 d . . . . .
O2 O 0.50837(11) 0.73560(10) 0.74431(6) 0.01595(16) Uani 1 1 d . . . . .
O3 O -0.05997(11) 0.17973(11) 0.99786(5) 0.01565(16) Uani 1 1 d . . . . .
O4 O 0.23834(11) 0.48252(11) 1.06283(5) 0.01637(16) Uani 1 1 d . . . . .
O5 O 0.90935(11) 1.16970(11) 0.29797(6) 0.01873(17) Uani 1 1 d . . . . .
C1 C 0.34402(14) 0.58035(14) 0.71345(7) 0.01162(18) Uani 1 1 d . . . . .
C2 C 0.22959(14) 0.46674(13) 0.78569(7) 0.01076(17) Uani 1 1 d . . . . .
C3 C 0.04919(14) 0.28466(14) 0.74751(7) 0.01248(18) Uani 1 1 d . . . . .
H3 H -0.001122 0.234611 0.674714 0.015 Uiso 1 1 calc R U . . .
C4 C -0.06034(14) 0.17307(14) 0.81354(7) 0.01334(18) Uani 1 1 d . . . . .
H4 H -0.183068 0.048525 0.787565 0.016 Uiso 1 1 calc R U . . .
C5 C 0.01984(14) 0.25400(14) 0.91785(7) 0.01183(18) Uani 1 1 d . . . . .
C6 C 0.10344(16) 0.30008(16) 1.09048(8) 0.0182(2) Uani 1 1 d . . . . .
H6A H 0.044348 0.330343 1.145449 0.022 Uiso 1 1 calc R U . . .
H6B H 0.181433 0.227514 1.116641 0.022 Uiso 1 1 calc R U . . .
C7 C 0.19984(14) 0.43649(14) 0.95651(7) 0.01164(18) Uani 1 1 d . . . . .
C8 C 0.30875(14) 0.54705(14) 0.89307(7) 0.01188(18) Uani 1 1 d . . . . .
H8 H 0.431299 0.671415 0.920068 0.014 Uiso 1 1 calc R U . . .
C9 C 0.73962(15) 1.02225(14) 0.26744(7) 0.01287(18) Uani 1 1 d . . . . .
C10 C 0.63825(14) 0.90711(14) 0.34430(7) 0.01159(17) Uani 1 1 d . . . . .
C11 C 0.44777(15) 0.73375(14) 0.31284(7) 0.01352(18) Uani 1 1 d . . . . .
H11 H 0.376813 0.684203 0.241195 0.016 Uiso 1 1 calc R U . . .
C12 C 0.36274(15) 0.63413(14) 0.38742(8) 0.01457(19) Uani 1 1 d . . . . .
H12 H 0.232374 0.516211 0.365389 0.017 Uiso 1 1 calc R U . . .
C14 C 0.64183(16) 0.86330(15) 0.51950(8) 0.0169(2) Uani 1 1 d . . . . .
H14 H 0.710398 0.907507 0.591595 0.020 Uiso 1 1 calc R U . . .
C15 C 0.73707(15) 0.97284(15) 0.45038(8) 0.01540(19) Uani 1 1 d . . . . .
H15 H 0.867263 1.090552 0.474767 0.018 Uiso 1 1 calc R U . . .
C16 C 0.62636(16) 0.94678(15) 0.15402(8) 0.01568(19) Uani 1 1 d . . . . .
H16A H 0.705521 1.038780 0.113280 0.024 Uiso 1 1 calc R U . . .
H16B H 0.488415 0.939781 0.142547 0.024 Uiso 1 1 calc R U . . .
H16C H 0.611316 0.812589 0.132333 0.024 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
O1 C1 1.3170(11) . ?
O1 H1O 0.8400 . ?
N1 C12 1.3370(12) . ?
N1 C14 1.3410(13) . ?
O2 C1 1.2233(11) . ?
O3 C5 1.3716(11) . ?
O3 C6 1.4408(12) . ?
O4 C7 1.3786(11) . ?
O4 C6 1.4356(12) . ?
O5 C9 1.2172(12) . ?
C1 C2 1.4921(13) . ?
C2 C3 1.3924(13) . ?
C2 C8 1.4095(13) . ?
C3 C4 1.4029(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.3736(13) . ?
C4 H4 0.9500 . ?
C5 C7 1.3933(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.3702(13) . ?
C8 H8 0.9500 . ?
C9 C16 1.5038(14) . ?
C9 C10 1.5069(13) . ?
C10 C11 1.3917(13) . ?
C10 C15 1.3955(13) . ?
C11 C12 1.3878(13) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 C15 1.3859(14) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1O 109.5 . . ?
C12 N1 C14 118.36(8) . . ?
C5 O3 C6 104.62(7) . . ?
C7 O4 C6 104.80(7) . . ?
O2 C1 O1 123.78(8) . . ?
O2 C1 C2 122.43(8) . . ?
O1 C1 C2 113.79(8) . . ?
C3 C2 C8 120.91(8) . . ?
C3 C2 C1 120.49(8) . . ?
C8 C2 C1 118.60(8) . . ?
C2 C3 C4 121.83(9) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 116.25(8) . . ?
C5 C4 H4 121.9 . . ?
C3 C4 H4 121.9 . . ?
O3 C5 C4 127.95(8) . . ?
O3 C5 C7 109.83(8) . . ?
C4 C5 C7 122.19(8) . . ?
O4 C6 O3 106.97(7) . . ?
O4 C6 H6A 110.3 . . ?
O3 C6 H6A 110.3 . . ?
O4 C6 H6B 110.3 . . ?
O3 C6 H6B 110.3 . . ?
H6A C6 H6B 108.6 . . ?
C8 C7 O4 128.51(8) . . ?
C8 C7 C5 122.26(9) . . ?
O4 C7 C5 109.19(8) . . ?
C7 C8 C2 116.56(8) . . ?
C7 C8 H8 121.7 . . ?
C2 C8 H8 121.7 . . ?
O5 C9 C16 122.18(9) . . ?
O5 C9 C10 119.87(9) . . ?
C16 C9 C10 117.94(8) . . ?
C11 C10 C15 118.21(8) . . ?
C11 C10 C9 121.94(8) . . ?
C15 C10 C9 119.85(8) . . ?
C12 C11 C10 119.18(9) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
N1 C12 C11 122.57(9) . . ?
N1 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
N1 C14 C15 122.86(9) . . ?
N1 C14 H14 118.6 . . ?
C15 C14 H14 118.6 . . ?
C14 C15 C10 118.80(9) . . ?
C14 C15 H15 120.6 . . ?
C10 C15 H15 120.6 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_C20ZB104_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2267802'
loop_
_audit_author_name
_audit_author_address
'Merce Font-Bardia' 'universitat de barcelona'
_audit_update_record             
;
2023-06-06 deposited with the CCDC.	2023-07-21 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         'C11 H11 N O3, C5 H5 N O'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31

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/c'
_space_group_name_Hall           '-P 2ybc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.3245(7)
_cell_length_b                   4.8311(2)
_cell_length_c                   18.3867(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.778(2)
_cell_angle_gamma                90
_cell_volume                     1465.41(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6608
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      29.07

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6929
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36859
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.277
_diffrn_reflns_theta_max         29.154
_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             3952
_reflns_number_gt                3010
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0383P)²+0.6810P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3952
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
O1 O 0.81709(6) 0.6025(2) 0.44501(6) 0.0209(2) Uani 1 1 d . . . . .
H1 H 0.8604(11) 0.483(4) 0.4546(2) 0.031 Uiso 1 1 calc R U . . .
O2 O 0.86207(6) 0.6638(2) 0.57214(6) 0.0246(2) Uani 1 1 d . . . . .
O3 O 0.70411(6) 0.54916(19) 0.60234(6) 0.0196(2) Uani 1 1 d . . . . .
O4 O 0.92392(6) 0.2255(2) 0.45583(6) 0.0240(2) Uani 1 1 d . . . . .
N1 N 0.72530(7) 0.9832(2) 0.56578(6) 0.0158(2) Uani 1 1 d . . . . .
H1N H 0.725185 1.160933 0.576274 0.019 Uiso 1 1 calc R U . . .
N2 N 0.97628(7) -0.1109(2) 0.39926(6) 0.0172(2) Uani 1 1 d . . . . .
H2 H 1.009956 -0.152961 0.444386 0.021 Uiso 1 1 calc R U . . .
C1 C 0.81363(8) 0.7107(3) 0.51010(8) 0.0169(3) Uani 1 1 d . . . . .
C2 C 0.74276(8) 0.9018(3) 0.49865(8) 0.0158(3) Uani 1 1 d . . . . .
C3 C 0.70444(8) 1.0063(3) 0.42962(8) 0.0166(3) Uani 1 1 d . . . . .
H3 H 0.725586 0.951950 0.389821 0.020 Uiso 1 1 calc R U . . .
C4 C 0.63420(8) 1.1935(3) 0.40674(8) 0.0163(3) Uani 1 1 d . . . . .
C5 C 0.57328(8) 1.1998(3) 0.44195(8) 0.0213(3) Uani 1 1 d . . . . .
H5 H 0.577266 1.084444 0.484797 0.026 Uiso 1 1 calc R U . . .
C6 C 0.50690(9) 1.3738(3) 0.41461(9) 0.0248(3) Uani 1 1 d . . . . .
H6 H 0.465405 1.374881 0.438493 0.030 Uiso 1 1 calc R U . . .
C7 C 0.50068(9) 1.5458(3) 0.35288(9) 0.0257(3) Uani 1 1 d . . . . .
H7 H 0.455385 1.665708 0.334852 0.031 Uiso 1 1 calc R U . . .
C8 C 0.56060(9) 1.5425(3) 0.31751(9) 0.0255(3) Uani 1 1 d . . . . .
H8 H 0.556854 1.661234 0.275386 0.031 Uiso 1 1 calc R U . . .
C9 C 0.62624(8) 1.3649(3) 0.34385(8) 0.0205(3) Uani 1 1 d . . . . .
H9 H 0.666517 1.360085 0.318533 0.025 Uiso 1 1 calc R U . . .
C10 C 0.70884(7) 0.8006(3) 0.61438(7) 0.0147(3) Uani 1 1 d . . . . .
C11 C 0.69522(8) 0.9220(3) 0.68471(8) 0.0193(3) Uani 1 1 d . . . . .
H11A H 0.698694 1.124216 0.682957 0.029 Uiso 1 1 calc R U . . .
H11B H 0.736664 0.852462 0.730165 0.029 Uiso 1 1 calc R U . . .
H11C H 0.641400 0.868440 0.686880 0.029 Uiso 1 1 calc R U . . .
C12 C 0.92261(8) 0.0984(3) 0.39526(8) 0.0173(3) Uani 1 1 d . . . . .
C13 C 0.86906(8) 0.1588(3) 0.32120(8) 0.0189(3) Uani 1 1 d . . . . .
H13 H 0.829761 0.301148 0.315041 0.023 Uiso 1 1 calc R U . . .
C14 C 0.87375(8) 0.0139(3) 0.25911(8) 0.0189(3) Uani 1 1 d . . . . .
H14 H 0.838277 0.058576 0.209936 0.023 Uiso 1 1 calc R U . . .
C15 C 0.93060(8) -0.2016(3) 0.26695(8) 0.0193(3) Uani 1 1 d . . . . .
H15 H 0.933566 -0.304146 0.223793 0.023 Uiso 1 1 calc R U . . .
C16 C 0.98122(8) -0.2588(3) 0.33820(8) 0.0181(3) Uani 1 1 d . . . . .
H16 H 1.020099 -0.402889 0.345059 0.022 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
O1 C1 1.3239(16) . ?
O1 H1 0.920(19) . ?
O2 C1 1.2133(16) . ?
O3 C10 1.2329(16) . ?
O4 C12 1.2657(17) . ?
N1 C10 1.3469(17) . ?
N1 C2 1.4133(17) . ?
N1 H1N 0.8800 . ?
N2 C16 1.3553(17) . ?
N2 C12 1.3605(17) . ?
N2 H2 0.8800 . ?
C1 C2 1.4989(18) . ?
C2 C3 1.3388(18) . ?
C3 C4 1.4707(18) . ?
C3 H3 0.9500 . ?
C4 C9 1.3943(19) . ?
C4 C5 1.3970(19) . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.3883(19) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.5028(18) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.4243(19) . ?
C13 C14 1.363(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.4099(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.3638(19) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C10 N1 C2 122.83(11) . . ?
C10 N1 H1N 118.6 . . ?
C2 N1 H1N 118.6 . . ?
C16 N2 C12 124.19(12) . . ?
C16 N2 H2 117.9 . . ?
C12 N2 H2 117.9 . . ?
O2 C1 O1 124.55(12) . . ?
O2 C1 C2 123.28(12) . . ?
O1 C1 C2 112.17(11) . . ?
C3 C2 N1 123.13(12) . . ?
C3 C2 C1 120.89(12) . . ?
N1 C2 C1 115.68(11) . . ?
C2 C3 C4 129.10(13) . . ?
C2 C3 H3 115.4 . . ?
C4 C3 H3 115.4 . . ?
C9 C4 C5 118.30(12) . . ?
C9 C4 C3 117.78(12) . . ?
C5 C4 C3 123.84(12) . . ?
C6 C5 C4 120.29(14) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 120.59(14) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C6 119.81(13) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 119.70(14) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 121.29(14) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
O3 C10 N1 122.84(12) . . ?
O3 C10 C11 121.31(12) . . ?
N1 C10 C11 115.84(11) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 N2 118.98(12) . . ?
O4 C12 C13 124.99(12) . . ?
N2 C12 C13 116.02(12) . . ?
C14 C13 C12 120.52(13) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.81(13) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 118.16(13) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
N2 C16 C15 120.29(13) . . ?
N2 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.052

