# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_NEt2OH-NFL
_audit_block_doi                 10.5517/ccdc.csd.cc2hbk1g
_database_code_depnum_ccdc_archive 'CCDC 2304045'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.cgd.4c00827 2024
loop_
_audit_author_name
_audit_author_address
'Dr. Manas K Panda'
;Jadavpur University
India
;
_audit_update_record             
;
2023-10-27 deposited with the CCDC.	2026-05-14 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         'C18 H21 N3 O2'
_chemical_formula_sum            'C18 H21 N3 O2'
_chemical_formula_weight         311.38

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                   14.8532(3)
_cell_length_b                   12.5608(2)
_cell_length_c                   9.33010(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.9650(10)
_cell_angle_gamma                90
_cell_volume                     1723.91(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      27.05

_exptl_crystal_description       blocky
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25906
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_av_R_equivalents  0.2024
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.737
_diffrn_reflns_theta_max         27.119
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3772
_reflns_number_gt                3111
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.1268P)²+0.3713P] 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         3772
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0727
_refine_ls_wR_factor_ref         0.2149
_refine_ls_wR_factor_gt          0.1969
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
O1 O 1.18782(8) 0.43676(11) 0.63229(14) 0.0469(4) Uani 1 1 d . . . . .
H1 H 1.195670 0.384909 0.685962 0.070 Uiso 1 1 calc R U . . .
O2 O 0.87117(9) 0.68615(11) 0.87986(13) 0.0488(4) Uani 1 1 d . . . . .
N2 N 0.75604(9) 0.77550(11) 0.66736(15) 0.0363(3) Uani 1 1 d . . . . .
N1 N 0.83143(9) 0.71631(11) 0.64142(14) 0.0360(3) Uani 1 1 d . . . . .
H4 H 0.842339 0.705364 0.554480 0.043 Uiso 1 1 calc R U . . .
C4 C 0.96691(10) 0.61569(13) 0.71920(16) 0.0337(4) Uani 1 1 d . . . . .
C7 C 0.88689(10) 0.67657(12) 0.75533(16) 0.0327(4) Uani 1 1 d . . . . .
C3 C 0.99457(11) 0.52756(15) 0.80399(17) 0.0402(4) Uani 1 1 d . . . . .
H3 H 0.963072 0.509316 0.879901 0.048 Uiso 1 1 calc R U . . .
C2 C 1.06789(11) 0.46650(14) 0.77786(18) 0.0411(4) Uani 1 1 d . . . . .
H2 H 1.085243 0.407333 0.835012 0.049 Uiso 1 1 calc R U . . .
C5 C 1.01499(11) 0.64282(14) 0.60638(18) 0.0385(4) Uani 1 1 d . . . . .
H5 H 0.997102 0.701340 0.548267 0.046 Uiso 1 1 calc R U . . .
C6 C 1.08942(11) 0.58281(15) 0.58055(18) 0.0410(4) Uani 1 1 d . . . . .
H6 H 1.121947 0.601915 0.506218 0.049 Uiso 1 1 calc R U . . .
C1 C 1.11549(10) 0.49438(14) 0.66524(17) 0.0367(4) Uani 1 1 d . . . . .
C9 C 0.60217(11) 0.82381(14) 0.58052(19) 0.0407(4) Uani 1 1 d . . . . .
C14 C 0.59009(12) 0.89354(15) 0.6909(2) 0.0454(4) Uani 1 1 d . . . . .
H14 H 0.640093 0.912637 0.757223 0.054 Uiso 1 1 calc R U . . .
N3 N 0.34547(11) 0.95465(16) 0.6195(2) 0.0653(5) Uani 1 1 d . . . . .
C8 C 0.68789(11) 0.77204(14) 0.56778(19) 0.0402(4) Uani 1 1 d . . . . .
H8 H 0.693486 0.734683 0.483409 0.048 Uiso 1 1 calc R U . . .
C12 C 0.42845(12) 0.90996(16) 0.6061(2) 0.0499(5) Uani 1 1 d . . . . .
C13 C 0.50618(13) 0.93558(16) 0.7055(2) 0.0501(5) Uani 1 1 d . . . . .
H13 H 0.500572 0.981528 0.781927 0.060 Uiso 1 1 calc R U . . .
C11 C 0.44099(13) 0.84068(19) 0.4950(3) 0.0605(6) Uani 1 1 d . . . . .
H11 H 0.391302 0.821662 0.427936 0.073 Uiso 1 1 calc R U . . .
C10 C 0.52566(13) 0.79912(18) 0.4813(2) 0.0561(5) Uani 1 1 d . . . . .
H10 H 0.531779 0.753773 0.404457 0.067 Uiso 1 1 calc R U . . .
C17 C 0.26619(15) 0.9342(2) 0.5114(4) 0.0810(8) Uani 1 1 d . . . . .
H17B H 0.286308 0.929413 0.417017 0.097 Uiso 1 1 calc R U . . .
H17A H 0.225395 0.994640 0.509327 0.097 Uiso 1 1 calc R U . . .
C15 C 0.33318(19) 1.0215(2) 0.7412(4) 0.0828(8) Uani 1 1 d . . . . .
H15B H 0.278243 1.063166 0.716178 0.099 Uiso 1 1 calc R U . . .
H15A H 0.383788 1.070853 0.757900 0.099 Uiso 1 1 calc R U . . .
C18 C 0.2138(2) 0.8350(3) 0.5357(7) 0.1312(17) Uani 1 1 d . . . . .
H18B H 0.159432 0.832340 0.466863 0.197 Uiso 1 1 calc R U . . .
H18C H 0.197926 0.835688 0.631970 0.197 Uiso 1 1 calc R U . . .
H18A H 0.250553 0.773647 0.523700 0.197 Uiso 1 1 calc R U . . .
C16 C 0.3265(3) 0.9628(4) 0.8787(5) 0.1359(17) Uani 1 1 d . . . . .
H16A H 0.277603 0.912355 0.863025 0.204 Uiso 1 1 calc R U . . .
H16C H 0.315148 1.012442 0.952376 0.204 Uiso 1 1 calc R U . . .
H16B H 0.382542 0.925954 0.909065 0.204 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 1.3652(18) . ?
O1 H1 0.8200 . ?
O2 C7 1.2224(19) . ?
N2 C8 1.276(2) . ?
N2 N1 1.3929(17) . ?
N1 C7 1.347(2) . ?
N1 H4 0.8600 . ?
C4 C3 1.389(2) . ?
C4 C5 1.394(2) . ?
C4 C7 1.491(2) . ?
C3 C2 1.381(2) . ?
C3 H3 0.9300 . ?
C2 C1 1.390(2) . ?
C2 H2 0.9300 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9300 . ?
C6 C1 1.387(2) . ?
C6 H6 0.9300 . ?
C9 C14 1.382(3) . ?
C9 C10 1.398(3) . ?
C9 C8 1.449(2) . ?
C14 C13 1.378(2) . ?
C14 H14 0.9300 . ?
N3 C12 1.376(2) . ?
N3 C15 1.444(4) . ?
N3 C17 1.463(3) . ?
C8 H8 0.9300 . ?
C12 C11 1.386(3) . ?
C12 C13 1.414(3) . ?
C13 H13 0.9300 . ?
C11 C10 1.384(3) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C17 C18 1.503(4) . ?
C17 H17B 0.9700 . ?
C17 H17A 0.9700 . ?
C15 C16 1.495(5) . ?
C15 H15B 0.9700 . ?
C15 H15A 0.9700 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 H18A 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16C 0.9600 . ?
C16 H16B 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
C1 O1 H1 109.5 . . ?
C8 N2 N1 115.53(13) . . ?
C7 N1 N2 118.63(12) . . ?
C7 N1 H4 120.7 . . ?
N2 N1 H4 120.7 . . ?
C3 C4 C5 118.87(14) . . ?
C3 C4 C7 117.53(13) . . ?
C5 C4 C7 123.60(14) . . ?
O2 C7 N1 122.48(14) . . ?
O2 C7 C4 121.92(14) . . ?
N1 C7 C4 115.55(13) . . ?
C2 C3 C4 121.35(14) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C2 C1 119.31(15) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C6 C5 C4 120.18(15) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C1 C6 C5 120.19(14) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
O1 C1 C6 117.56(14) . . ?
O1 C1 C2 122.35(15) . . ?
C6 C1 C2 120.08(15) . . ?
C14 C9 C10 117.15(16) . . ?
C14 C9 C8 123.48(16) . . ?
C10 C9 C8 119.29(16) . . ?
C13 C14 C9 121.96(17) . . ?
C13 C14 H14 119.0 . . ?
C9 C14 H14 119.0 . . ?
C12 N3 C15 121.4(2) . . ?
C12 N3 C17 120.7(2) . . ?
C15 N3 C17 117.8(2) . . ?
N2 C8 C9 122.83(15) . . ?
N2 C8 H8 118.6 . . ?
C9 C8 H8 118.6 . . ?
N3 C12 C11 122.63(19) . . ?
N3 C12 C13 120.52(19) . . ?
C11 C12 C13 116.84(16) . . ?
C14 C13 C12 121.02(18) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C10 C11 C12 121.59(19) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C10 C9 121.42(19) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
N3 C17 C18 115.2(3) . . ?
N3 C17 H17B 108.5 . . ?
C18 C17 H17B 108.5 . . ?
N3 C17 H17A 108.5 . . ?
C18 C17 H17A 108.5 . . ?
H17B C17 H17A 107.5 . . ?
N3 C15 C16 114.7(3) . . ?
N3 C15 H15B 108.6 . . ?
C16 C15 H15B 108.6 . . ?
N3 C15 H15A 108.6 . . ?
C16 C15 H15A 108.6 . . ?
H15B C15 H15A 107.6 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
H18B C18 H18A 109.5 . . ?
H18C C18 H18A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16C C16 H16B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N2 N1 C7 -150.86(16) . . . . ?
N2 N1 C7 O2 3.6(2) . . . . ?
N2 N1 C7 C4 -179.02(13) . . . . ?
C3 C4 C7 O2 33.6(2) . . . . ?
C5 C4 C7 O2 -146.07(17) . . . . ?
C3 C4 C7 N1 -143.78(16) . . . . ?
C5 C4 C7 N1 36.5(2) . . . . ?
C5 C4 C3 C2 -0.5(3) . . . . ?
C7 C4 C3 C2 179.83(15) . . . . ?
C4 C3 C2 C1 0.6(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C7 C4 C5 C6 179.29(15) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C5 C6 C1 O1 178.31(15) . . . . ?
C5 C6 C1 C2 -1.0(3) . . . . ?
C3 C2 C1 O1 -179.13(15) . . . . ?
C3 C2 C1 C6 0.1(3) . . . . ?
C10 C9 C14 C13 1.4(3) . . . . ?
C8 C9 C14 C13 -175.35(17) . . . . ?
N1 N2 C8 C9 176.35(15) . . . . ?
C14 C9 C8 N2 9.5(3) . . . . ?
C10 C9 C8 N2 -167.18(19) . . . . ?
C15 N3 C12 C11 176.2(2) . . . . ?
C17 N3 C12 C11 -2.7(3) . . . . ?
C15 N3 C12 C13 -5.3(3) . . . . ?
C17 N3 C12 C13 175.8(2) . . . . ?
C9 C14 C13 C12 -0.9(3) . . . . ?
N3 C12 C13 C14 -178.24(18) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
N3 C12 C11 C10 178.1(2) . . . . ?
C13 C12 C11 C10 -0.4(3) . . . . ?
C12 C11 C10 C9 1.1(4) . . . . ?
C14 C9 C10 C11 -1.5(3) . . . . ?
C8 C9 C10 C11 175.4(2) . . . . ?
C12 N3 C17 C18 86.1(3) . . . . ?
C15 N3 C17 C18 -92.9(3) . . . . ?
C12 N3 C15 C16 -77.0(3) . . . . ?
C17 N3 C15 C16 102.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N2 0.82 2.00 2.8037(19) 166.0 2_746 yes
N1 H4 O1 0.86 2.49 3.178(2) 137.3 3_766 yes
N1 H4 O2 0.86 2.21 2.8642(18) 132.7 4_575 yes
C2 H2 N1 0.93 2.69 3.517(2) 147.8 2_746 yes

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_NMe2OH-G
_audit_block_doi                 10.5517/ccdc.csd.cc2hbk0f
_database_code_depnum_ccdc_archive 'CCDC 2304044'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.cgd.4c00827 2024
loop_
_audit_author_name
_audit_author_address
'Dr. Manas K Panda'
;Jadavpur University
India
;
_audit_update_record             
;
2023-10-27 deposited with the CCDC.	2026-05-14 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         'C32 H34 N6 O4. H2O'
_chemical_formula_sum            'C32 H36 N6 O5'
_chemical_formula_weight         584.67

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.1510(6)
_cell_length_b                   18.1218(17)
_cell_length_c                   13.3714(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.413(3)
_cell_angle_gamma                90
_cell_volume                     1483.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9559
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.12

_exptl_crystal_description       blocky
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            100361
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.061
_diffrn_reflns_theta_max         27.158
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             6472
_reflns_number_gt                6313
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_max     0.983
_reflns_Friedel_fraction_full    0.983

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0612P)²+0.1242P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2995 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6472
_refine_ls_number_parameters     405
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 1.2677(3) 0.69251(10) 0.20272(17) 0.0655(5) Uani 1 1 d G . . . .
H00A H 1.383530 0.666671 0.209914 0.098 Uiso 1 1 d G U . . .
H00B H 1.311128 0.736381 0.214259 0.098 Uiso 1 1 d G U . . .
O1 O 0.3149(3) 0.56821(10) 0.36511(13) 0.0611(4) Uani 1 1 d . . . . .
H1 H 0.408657 0.566204 0.325452 0.092 Uiso 1 1 calc R U . . .
O2 O 0.7084(3) 0.35768(9) 0.71603(11) 0.0578(4) Uani 1 1 d . . . . .
O3 O 0.9809(3) 0.45521(11) -0.18395(13) 0.0633(4) Uani 1 1 d . . . . .
H3 H 0.890046 0.425674 -0.208543 0.095 Uiso 1 1 calc R U . . .
O4 O 0.5397(3) 0.54862(12) 0.20457(12) 0.0639(5) Uani 1 1 d . . . . .
N1 N 0.3939(4) 0.31045(10) 0.82895(13) 0.0516(4) Uani 1 1 d . . . . .
N6 N 0.3521(4) 0.35244(12) 0.74234(15) 0.0556(4) Uani 1 1 d . . . . .
N3 N 0.7235(4) 0.85587(13) 0.71060(15) 0.0609(5) Uani 1 1 d . . . . .
N4 N 0.7642(3) 0.64854(10) 0.31662(12) 0.0447(4) Uani 1 1 d . . . . .
N5 N 0.8445(3) 0.61654(10) 0.23305(13) 0.0455(4) Uani 1 1 d . . . . .
C1 C 0.4149(5) 0.09738(17) 1.2786(2) 0.0685(7) Uani 1 1 d . . . . .
H1A H 0.451121 0.061268 1.230351 0.103 Uiso 1 1 calc R U . . .
H1B H 0.383377 0.073006 1.339348 0.103 Uiso 1 1 calc R U . . .
H1C H 0.535971 0.130372 1.292890 0.103 Uiso 1 1 calc R U . . .
N2 N 0.2268(3) 0.13850(11) 1.23866(14) 0.0553(5) Uani 1 1 d . . . . .
C3 C 0.2272(3) 0.17691(11) 1.15030(14) 0.0427(4) Uani 1 1 d . . . . .
C4 C 0.0449(4) 0.21786(13) 1.11078(17) 0.0509(5) Uani 1 1 d . . . . .
H4 H -0.079561 0.219447 1.145170 0.061 Uiso 1 1 calc R U . . .
C5 C 0.0488(4) 0.25564(13) 1.02165(19) 0.0536(5) Uani 1 1 d . . . . .
H5 H -0.074595 0.281780 0.996598 0.064 Uiso 1 1 calc R U . . .
C6 C 0.2319(4) 0.25591(11) 0.96789(15) 0.0465(4) Uani 1 1 d . . . . .
C7 C 0.2253(4) 0.29746(12) 0.87484(17) 0.0531(5) Uani 1 1 d . . . . .
H7 H 0.091294 0.315538 0.847283 0.064 Uiso 1 1 calc R U . . .
C8 C 0.5177(4) 0.37612(11) 0.69169(14) 0.0450(4) Uani 1 1 d . . . . .
C9 C 0.4574(3) 0.42623(10) 0.60544(13) 0.0407(4) Uani 1 1 d . . . . .
C10 C 0.6122(3) 0.43947(11) 0.53806(14) 0.0448(4) Uani 1 1 d . . . . .
H10 H 0.747213 0.416116 0.547559 0.054 Uiso 1 1 calc R U . . .
C11 C 0.5695(3) 0.48657(12) 0.45738(15) 0.0460(4) Uani 1 1 d . . . . .
H11 H 0.674894 0.494510 0.413064 0.055 Uiso 1 1 calc R U . . .
C12 C 0.3685(3) 0.52213(11) 0.44248(14) 0.0433(4) Uani 1 1 d . . . . .
C13 C 0.4122(3) 0.17674(12) 1.09506(15) 0.0464(4) Uani 1 1 d . . . . .
H13 H 0.535271 0.149976 1.118987 0.056 Uiso 1 1 calc R U . . .
C14 C 0.4137(3) 0.21539(12) 1.00668(16) 0.0470(4) Uani 1 1 d . . . . .
H14 H 0.537924 0.214520 0.972111 0.056 Uiso 1 1 calc R U . . .
C15 C 0.0327(5) 0.13298(16) 1.29037(19) 0.0636(6) Uani 1 1 d . . . . .
H15A H -0.020283 0.181567 1.303226 0.095 Uiso 1 1 calc R U . . .
H15B H 0.066029 0.107507 1.352890 0.095 Uiso 1 1 calc R U . . .
H15C H -0.077194 0.106173 1.249516 0.095 Uiso 1 1 calc R U . . .
C16 C 0.2580(3) 0.46340(12) 0.59078(14) 0.0472(4) Uani 1 1 d . . . . .
H16 H 0.153159 0.456023 0.635565 0.057 Uiso 1 1 calc R U . . .
C17 C 0.2144(3) 0.51083(13) 0.51089(16) 0.0496(5) Uani 1 1 d . . . . .
H17 H 0.081262 0.535453 0.502570 0.059 Uiso 1 1 calc R U . . .
C18 C 0.5217(5) 0.85041(17) 0.7559(2) 0.0681(7) Uani 1 1 d . . . . .
H18A H 0.412063 0.879471 0.718244 0.102 Uiso 1 1 calc R U . . .
H18B H 0.542229 0.868335 0.823713 0.102 Uiso 1 1 calc R U . . .
H18C H 0.475774 0.799788 0.756108 0.102 Uiso 1 1 calc R U . . .
C19 C 0.7615(4) 0.81608(12) 0.62646(15) 0.0460(4) Uani 1 1 d . . . . .
C20 C 0.6031(3) 0.76813(12) 0.57867(16) 0.0482(4) Uani 1 1 d . . . . .
H20 H 0.468500 0.763529 0.604442 0.058 Uiso 1 1 calc R U . . .
C21 C 0.6430(3) 0.72809(12) 0.49496(16) 0.0468(4) Uani 1 1 d . . . . .
H21 H 0.534915 0.697125 0.465226 0.056 Uiso 1 1 calc R U . . .
C22 C 0.8432(3) 0.73311(11) 0.45375(14) 0.0423(4) Uani 1 1 d . . . . .
C23 C 0.8966(3) 0.69267(12) 0.36558(15) 0.0451(4) Uani 1 1 d . . . . .
H23 H 1.034302 0.699239 0.343618 0.054 Uiso 1 1 calc R U . . .
C24 C 0.7201(3) 0.56739(11) 0.17976(13) 0.0407(4) Uani 1 1 d . . . . .
C25 C 0.8034(3) 0.53647(10) 0.08699(13) 0.0394(4) Uani 1 1 d . . . . .
C26 C 0.6687(3) 0.48703(13) 0.03139(15) 0.0491(4) Uani 1 1 d . . . . .
H26 H 0.537333 0.472983 0.054899 0.059 Uiso 1 1 calc R U . . .
C27 C 0.7258(4) 0.45820(14) -0.05822(16) 0.0530(5) Uani 1 1 d . . . . .
H27 H 0.633915 0.424970 -0.094425 0.064 Uiso 1 1 calc R U . . .
C28 C 0.9213(4) 0.47926(11) -0.09368(15) 0.0477(4) Uani 1 1 d . . . . .
C29 C 0.8875(5) 0.90377(19) 0.7596(2) 0.0752(8) Uani 1 1 d . . . . .
H29A H 1.010445 0.874897 0.786200 0.113 Uiso 1 1 calc R U . . .
H29B H 0.827625 0.929630 0.813383 0.113 Uiso 1 1 calc R U . . .
H29C H 0.933582 0.938711 0.711965 0.113 Uiso 1 1 calc R U . . .
C30 C 0.9615(4) 0.82149(13) 0.58396(17) 0.0521(5) Uani 1 1 d . . . . .
H30 H 1.069494 0.852843 0.612820 0.063 Uiso 1 1 calc R U . . .
C31 C 0.9995(4) 0.78109(13) 0.50038(17) 0.0498(4) Uani 1 1 d . . . . .
H31 H 1.133412 0.785808 0.474001 0.060 Uiso 1 1 calc R U . . .
C32 C 1.0015(3) 0.55546(13) 0.05219(16) 0.0490(4) Uani 1 1 d . . . . .
H32 H 1.095424 0.587679 0.089114 0.059 Uiso 1 1 calc R U . . .
C33 C 1.0596(4) 0.52646(13) -0.03765(17) 0.0534(5) Uani 1 1 d . . . . .
H33 H 1.193267 0.539025 -0.060182 0.064 Uiso 1 1 calc R U . . .
H5A H 0.965(5) 0.6336(16) 0.216(2) 0.057(7) Uiso 1 1 d . . . . .
H6 H 0.225(6) 0.368(2) 0.724(2) 0.074(10) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 H00A 0.8504 . ?
O001 H00B 0.8482 . ?
O1 C12 1.346(2) . ?
O1 H1 0.8200 . ?
O2 C8 1.233(3) . ?
O3 C28 1.365(2) . ?
O3 H3 0.8200 . ?
O4 C24 1.236(2) . ?
N1 C7 1.276(3) . ?
N1 N6 1.389(2) . ?
N6 C8 1.346(3) . ?
N6 H6 0.84(4) . ?
N3 C19 1.375(3) . ?
N3 C18 1.435(3) . ?
N3 C29 1.441(3) . ?
N4 C23 1.277(3) . ?
N4 N5 1.391(2) . ?
N5 C24 1.336(3) . ?
N5 H5A 0.85(3) . ?
C1 N2 1.437(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C3 1.371(2) . ?
N2 C15 1.438(3) . ?
C3 C4 1.406(3) . ?
C3 C13 1.414(3) . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C6 C14 1.396(3) . ?
C6 C7 1.452(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.487(3) . ?
C9 C10 1.392(3) . ?
C9 C16 1.397(3) . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.391(3) . ?
C11 H11 0.9300 . ?
C12 C17 1.393(3) . ?
C13 C14 1.374(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.377(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C30 1.406(3) . ?
C19 C20 1.412(3) . ?
C20 C21 1.375(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.399(3) . ?
C21 H21 0.9300 . ?
C22 C31 1.398(3) . ?
C22 C23 1.452(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.495(2) . ?
C25 C26 1.388(3) . ?
C25 C32 1.388(3) . ?
C26 C27 1.382(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.387(3) . ?
C27 H27 0.9300 . ?
C28 C33 1.377(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.375(3) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 C33 1.389(3) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?

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
H00A O001 H00B 104.4 . . ?
C12 O1 H1 109.5 . . ?
C28 O3 H3 109.5 . . ?
C7 N1 N6 114.0(2) . . ?
C8 N6 N1 120.3(2) . . ?
C8 N6 H6 118(2) . . ?
N1 N6 H6 121(2) . . ?
C19 N3 C18 122.0(2) . . ?
C19 N3 C29 121.5(2) . . ?
C18 N3 C29 116.5(2) . . ?
C23 N4 N5 114.52(17) . . ?
C24 N5 N4 118.53(16) . . ?
C24 N5 H5A 124.8(19) . . ?
N4 N5 H5A 116.4(19) . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 N2 C1 121.11(19) . . ?
C3 N2 C15 121.3(2) . . ?
C1 N2 C15 117.5(2) . . ?
N2 C3 C4 121.69(18) . . ?
N2 C3 C13 121.08(18) . . ?
C4 C3 C13 117.23(17) . . ?
C5 C4 C3 120.64(19) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 122.0(2) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C14 117.70(18) . . ?
C5 C6 C7 119.1(2) . . ?
C14 C6 C7 123.3(2) . . ?
N1 C7 C6 123.3(2) . . ?
N1 C7 H7 118.3 . . ?
C6 C7 H7 118.3 . . ?
O2 C8 N6 121.81(19) . . ?
O2 C8 C9 122.11(19) . . ?
N6 C8 C9 116.08(19) . . ?
C10 C9 C16 118.12(17) . . ?
C10 C9 C8 118.12(18) . . ?
C16 C9 C8 123.69(17) . . ?
C11 C10 C9 121.37(18) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 119.94(17) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
O1 C12 C11 123.18(17) . . ?
O1 C12 C17 117.60(18) . . ?
C11 C12 C17 119.22(17) . . ?
C14 C13 C3 121.26(18) . . ?
C14 C13 H13 119.4 . . ?
C3 C13 H13 119.4 . . ?
C13 C14 C6 121.18(18) . . ?
C13 C14 H14 119.4 . . ?
C6 C14 H14 119.4 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C9 120.91(17) . . ?
C17 C16 H16 119.5 . . ?
C9 C16 H16 119.5 . . ?
C16 C17 C12 120.41(19) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C30 121.1(2) . . ?
N3 C19 C20 122.0(2) . . ?
C30 C19 C20 116.89(18) . . ?
C21 C20 C19 121.6(2) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C22 121.17(19) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C31 C22 C21 117.30(18) . . ?
C31 C22 C23 118.51(18) . . ?
C21 C22 C23 124.19(18) . . ?
N4 C23 C22 123.38(18) . . ?
N4 C23 H23 118.3 . . ?
C22 C23 H23 118.3 . . ?
O4 C24 N5 121.61(18) . . ?
O4 C24 C25 120.42(18) . . ?
N5 C24 C25 117.95(16) . . ?
C26 C25 C32 118.62(18) . . ?
C26 C25 C24 116.91(16) . . ?
C32 C25 C24 124.44(18) . . ?
C27 C26 C25 121.39(19) . . ?
C27 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C26 C27 C28 119.4(2) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
O3 C28 C33 118.4(2) . . ?
O3 C28 C27 121.9(2) . . ?
C33 C28 C27 119.73(19) . . ?
N3 C29 H29A 109.5 . . ?
N3 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N3 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C19 120.93(19) . . ?
C31 C30 H30 119.5 . . ?
C19 C30 H30 119.5 . . ?
C30 C31 C22 122.1(2) . . ?
C30 C31 H31 119.0 . . ?
C22 C31 H31 119.0 . . ?
C25 C32 C33 120.1(2) . . ?
C25 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C28 C33 C32 120.6(2) . . ?
C28 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N6 C8 173.7(2) . . . . ?
C23 N4 N5 C24 177.37(18) . . . . ?
C1 N2 C3 C4 -179.5(2) . . . . ?
C15 N2 C3 C4 5.6(3) . . . . ?
C1 N2 C3 C13 0.6(3) . . . . ?
C15 N2 C3 C13 -174.3(2) . . . . ?
N2 C3 C4 C5 -179.6(2) . . . . ?
C13 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C4 C5 C6 C14 0.8(3) . . . . ?
C4 C5 C6 C7 -179.5(2) . . . . ?
N6 N1 C7 C6 -178.8(2) . . . . ?
C5 C6 C7 N1 168.7(2) . . . . ?
C14 C6 C7 N1 -11.7(3) . . . . ?
N1 N6 C8 O2 4.8(3) . . . . ?
N1 N6 C8 C9 -174.67(18) . . . . ?
O2 C8 C9 C10 14.1(3) . . . . ?
N6 C8 C9 C10 -166.42(19) . . . . ?
O2 C8 C9 C16 -162.9(2) . . . . ?
N6 C8 C9 C16 16.6(3) . . . . ?
C16 C9 C10 C11 -1.5(3) . . . . ?
C8 C9 C10 C11 -178.64(19) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 O1 -179.4(2) . . . . ?
C10 C11 C12 C17 1.4(3) . . . . ?
N2 C3 C13 C14 -179.8(2) . . . . ?
C4 C3 C13 C14 0.3(3) . . . . ?
C3 C13 C14 C6 -0.4(3) . . . . ?
C5 C6 C14 C13 -0.2(3) . . . . ?
C7 C6 C14 C13 -179.9(2) . . . . ?
C10 C9 C16 C17 1.1(3) . . . . ?
C8 C9 C16 C17 178.0(2) . . . . ?
C9 C16 C17 C12 0.6(3) . . . . ?
O1 C12 C17 C16 178.9(2) . . . . ?
C11 C12 C17 C16 -1.8(3) . . . . ?
C18 N3 C19 C30 -179.2(2) . . . . ?
C29 N3 C19 C30 -1.0(4) . . . . ?
C18 N3 C19 C20 0.9(4) . . . . ?
C29 N3 C19 C20 179.1(2) . . . . ?
N3 C19 C20 C21 -179.5(2) . . . . ?
C30 C19 C20 C21 0.5(3) . . . . ?
C19 C20 C21 C22 0.2(3) . . . . ?
C20 C21 C22 C31 -0.8(3) . . . . ?
C20 C21 C22 C23 -179.9(2) . . . . ?
N5 N4 C23 C22 178.55(18) . . . . ?
C31 C22 C23 N4 -178.8(2) . . . . ?
C21 C22 C23 N4 0.3(3) . . . . ?
N4 N5 C24 O4 -1.9(3) . . . . ?
N4 N5 C24 C25 176.76(16) . . . . ?
O4 C24 C25 C26 0.4(3) . . . . ?
N5 C24 C25 C26 -178.31(18) . . . . ?
O4 C24 C25 C32 178.6(2) . . . . ?
N5 C24 C25 C32 -0.1(3) . . . . ?
C32 C25 C26 C27 -1.6(3) . . . . ?
C24 C25 C26 C27 176.7(2) . . . . ?
C25 C26 C27 C28 -0.2(4) . . . . ?
C26 C27 C28 O3 -176.9(2) . . . . ?
C26 C27 C28 C33 2.3(4) . . . . ?
N3 C19 C30 C31 179.4(2) . . . . ?
C20 C19 C30 C31 -0.6(3) . . . . ?
C19 C30 C31 C22 0.0(4) . . . . ?
C21 C22 C31 C30 0.7(3) . . . . ?
C23 C22 C31 C30 179.8(2) . . . . ?
C26 C25 C32 C33 1.4(3) . . . . ?
C24 C25 C32 C33 -176.76(19) . . . . ?
O3 C28 C33 C32 176.7(2) . . . . ?
C27 C28 C33 C32 -2.5(3) . . . . ?
C25 C32 C33 C28 0.7(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
O1 H1 O4 0.82 1.90 2.684(2) 159.7 . yes
O1 H1 N4 0.82 2.66 3.242(2) 129.4 . yes
O3 H3 O2 0.82 1.89 2.702(3) 170.4 1_554 yes
C7 H7 O3 0.93 2.64 3.290(3) 127.2 1_456 yes
C23 H23 O001 0.93 2.48 3.300(3) 147.6 . yes
C27 H27 N1 0.93 2.69 3.610(3) 169.0 1_554 yes
N5 H5A O001 0.85(3) 2.17(3) 3.006(2) 167(3) . yes
N6 H6 O3 0.84(4) 2.58(3) 3.174(3) 129(3) 1_456 yes

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.027

####################################################################### 
# 
# 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_NEt2OH-FL
_audit_block_doi                 10.5517/ccdc.csd.cc2k6dls
_database_code_depnum_ccdc_archive 'CCDC 2359645'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.cgd.4c00827 2024
loop_
_audit_author_name
_audit_author_address
'Manas K Panda'
;Jadavpur University, Department of Chemistry
India
;
_audit_update_record             
;
2024-05-31 deposited with the CCDC.	2026-05-14 downloaded from the CCDC.
;
_audit_creation_date             2024-05-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_formula_moiety         'C18 H21 N3 O2, 0.5(C H4 O)'
_chemical_formula_sum            'C18.5 H23 N3 O2.5'
_chemical_formula_weight         327.408
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 0.00313 0.00162 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)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 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)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 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)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y+1/4,x+3/4,z+3/4
3 y+1/4,-x+1/4,z+1/4
4 -x,-y+1/2,z
5 -x,-y,-z
6 y-1/4,-x-3/4,-z-3/4
7 -y-1/4,x-1/4,-z-1/4
8 x,y-1/2,-z
9 x+1/2,y+1/2,z+1/2
10 -y+3/4,x+5/4,z+5/4
11 y+3/4,-x+3/4,z+3/4
12 -x+1/2,-y+1,z+1/2
13 -x+1/2,-y+1/2,-z+1/2
14 y+1/4,-x-1/4,-z-1/4
15 -y+1/4,x+1/4,-z+1/4
16 x+1/2,y,-z+1/2

_symmetry_Int_Tables_number      88
_cell_length_a                   22.3869(19)
_cell_length_b                   22.3869(19)
_cell_length_c                   14.9090(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7472.0(13)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    186.98
_cell_measurement_theta_max      27.236
_cell_measurement_theta_min      2.450
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1003 before and 0.0673 after correction.
The Ratio of minimum to maximum transmission is 0.8803.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_description       block
_exptl_crystal_F_000             2801.794
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.9867
_diffrn_reflns_Laue_measured_fraction_max 0.9912
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            51130
_diffrn_reflns_point_group_measured_fraction_full 0.9867
_diffrn_reflns_point_group_measured_fraction_max 0.9912
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         29.25
_diffrn_reflns_theta_min         2.45
_diffrn_ambient_temperature      186.98
_diffrn_measured_fraction_theta_full 0.9867
_diffrn_measured_fraction_theta_max 0.9912
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              30
_reflns_limit_h_min              0
_reflns_limit_k_max              30
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                3384
_reflns_number_total             5045
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.4504
_refine_diff_density_min         -0.3065
_refine_diff_density_rms         0.0616
_refine_ls_d_res_high            0.7272
_refine_ls_d_res_low             8.3116
_refine_ls_goodness_of_fit_ref   1.2845
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    39
_refine_ls_number_parameters     235
_refine_ls_number_reflns         5045
_refine_ls_number_restraints     225
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0626
_refine_ls_restrained_S_all      1.2555
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1296P)²+3.2767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1849
_refine_ls_wR_factor_ref         0.2741
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O3-H3a
 0.84 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O3(0.5) C4(0.5) H4a(0.5) H4b(0.5) H4c(0.5)
 Fixed Uiso: H3a(0.228239)
6.a Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b), C17(H17a,H17b)
6.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C14(H14), C3(H3), C5(H5), C10(H10), C2(H2), C6(H6), C13(H13), C11(H11)
6.c Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C18(H18a,H18b,H18c), C4(H4a,H4b,H4c)
6.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_group
O2 O 0.83853(7) 0.43098(7) 0.57753(10) 0.0516(4) Uani 1.000000 1 . U . .
O1 O 0.83770(9) 0.18096(7) 0.78455(12) 0.0621(5) Uani 1.000000 1 . U . .
H1 H 0.8399(17) 0.15608(15) 0.74250(12) 0.0932(7) Uiso 1.000000 1 GR . . .
N2 N 0.77402(7) 0.51147(7) 0.66792(12) 0.0428(4) Uani 1.000000 1 . U . .
N1 N 0.78243(8) 0.45331(7) 0.69859(12) 0.0427(4) Uani 1.000000 1 . U . .
C7 C 0.81626(8) 0.41546(9) 0.65046(13) 0.0402(4) Uani 1.000000 1 . U . .
N3 N 0.66779(10) 0.78023(9) 0.64558(16) 0.0620(6) Uani 1.000000 1 . U . .
C8 C 0.74365(9) 0.54458(9) 0.72149(14) 0.0450(5) Uani 1.000000 1 . U . .
H8 H 0.73150(9) 0.52825(9) 0.77739(14) 0.0540(5) Uiso 1.000000 1 R . . .
C19 C 0.82389(9) 0.35461(9) 0.68814(14) 0.0416(4) Uani 1.000000 1 . U . .
C9 C 0.72698(9) 0.60571(9) 0.70087(14) 0.0443(5) Uani 1.000000 1 . U . .
C12 C 0.68810(10) 0.72393(10) 0.66455(16) 0.0501(5) Uani 1.000000 1 . U . .
C1 C 0.83366(10) 0.23703(9) 0.75001(16) 0.0478(5) Uani 1.000000 1 . U . .
C14 C 0.69763(10) 0.63956(10) 0.76534(15) 0.0491(5) Uani 1.000000 1 . U . .
H14 H 0.68999(10) 0.62236(10) 0.82245(15) 0.0589(6) Uiso 1.000000 1 R . . .
C3 C 0.83921(10) 0.30814(10) 0.63040(15) 0.0499(5) Uani 1.000000 1 . U . .
H3 H 0.84670(10) 0.31660(10) 0.56898(15) 0.0599(6) Uiso 1.000000 1 R . . .
C5 C 0.81478(10) 0.34130(9) 0.77849(15) 0.0488(5) Uani 1.000000 1 . U . .
H5 H 0.80502(10) 0.37240(9) 0.81928(15) 0.0585(6) Uiso 1.000000 1 R . . .
C10 C 0.73741(10) 0.63220(10) 0.61763(16) 0.0511(5) Uani 1.000000 1 . U . .
H10 H 0.75808(10) 0.61030(10) 0.57275(16) 0.0613(6) Uiso 1.000000 1 R . . .
C2 C 0.84375(11) 0.24987(10) 0.66079(16) 0.0530(5) Uani 1.000000 1 . U . .
H2 H 0.85381(11) 0.21874(10) 0.62021(16) 0.0636(6) Uiso 1.000000 1 R . . .
C6 C 0.81983(11) 0.28318(10) 0.80931(15) 0.0522(5) Uani 1.000000 1 . U . .
H6 H 0.81386(11) 0.27470(10) 0.87110(15) 0.0626(6) Uiso 1.000000 1 R . . .
C13 C 0.67924(10) 0.69735(10) 0.74904(16) 0.0517(5) Uani 1.000000 1 . U . .
H13 H 0.66035(10) 0.71949(10) 0.79542(16) 0.0621(6) Uiso 1.000000 1 R . . .
C11 C 0.71837(11) 0.68959(10) 0.59899(17) 0.0544(6) Uani 1.000000 1 . U . .
H11 H 0.72567(11) 0.70623(10) 0.54141(17) 0.0653(7) Uiso 1.000000 1 R . . .
C15 C 0.66544(13) 0.80263(11) 0.5525(2) 0.0644(7) Uani 1.000000 1 . U . .
H15a H 0.65774(13) 0.76872(11) 0.5115(2) 0.0773(8) Uiso 1.000000 1 R . . .
H15b H 0.63174(13) 0.83101(11) 0.5467(2) 0.0773(8) Uiso 1.000000 1 R . . .
C17 C 0.64102(14) 0.81757(12) 0.7146(2) 0.0706(7) Uani 1.000000 1 . U . .
H17a H 0.66175(14) 0.81030(12) 0.7722(2) 0.0847(9) Uiso 1.000000 1 R . . .
H17b H 0.64691(14) 0.86007(12) 0.6985(2) 0.0847(9) Uiso 1.000000 1 R . . .
C16 C 0.72210(15) 0.83329(15) 0.5246(3) 0.0805(9) Uani 1.000000 1 . U . .
H16a H 0.7182(5) 0.8475(11) 0.4627(6) 0.1207(13) Uiso 1.000000 1 GR . . .
H16b H 0.7296(6) 0.8673(7) 0.5644(11) 0.1207(13) Uiso 1.000000 1 GR . . .
H16c H 0.7555(2) 0.8051(4) 0.5286(17) 0.1207(13) Uiso 1.000000 1 GR . . .
C18 C 0.57543(15) 0.80589(17) 0.7266(3) 0.0896(10) Uani 1.000000 1 . U . .
H18a H 0.5548(2) 0.8118(13) 0.6693(5) 0.1343(15) Uiso 1.000000 1 GR . . .
H18b H 0.56949(17) 0.7647(4) 0.7469(19) 0.1343(15) Uiso 1.000000 1 GR . . .
H18c H 0.5592(3) 0.8335(9) 0.7713(14) 0.1343(15) Uiso 1.000000 1 GR . . .
H1a H 0.7649(12) 0.4408(12) 0.747(2) 0.058(7) Uiso 1.000000 1 . . . .
O3 O 0.9675(4) 0.2494(3) 0.4713(6) 0.152(3) Uani 0.500000 1 D U P -1
C4 C 0.9230(5) 0.2803(4) 0.4242(7) 0.122(3) Uani 0.500000 1 . U P -1
H4a H 0.9376(14) 0.290(3) 0.364(2) 0.183(5) Uiso 0.500000 1 GR . P -1
H4b H 0.8873(13) 0.2551(15) 0.419(5) 0.183(5) Uiso 0.500000 1 GR . P -1
H4c H 0.913(3) 0.317(2) 0.456(3) 0.183(5) Uiso 0.500000 1 GR . P -1
H3a H 1.0 0.25 0.501(3) 0.228(4) Uiso 0.5 1 DRS T P -1


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
O2 C7 1.246(2) . ?
O1 H1 0.8400 . ?
O1 C1 1.360(3) . ?
N2 N1 1.393(2) . ?
N2 C8 1.284(3) . ?
N1 C7 1.344(3) . ?
N1 H1a 0.87(3) . ?
C7 C19 1.483(3) . ?
N3 C12 1.370(3) . ?
N3 C15 1.477(4) . ?
N3 C17 1.455(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.451(3) . ?
C19 C3 1.393(3) . ?
C19 C5 1.395(3) . ?
C9 C14 1.389(3) . ?
C9 C10 1.395(3) . ?
C12 C13 1.407(3) . ?
C12 C11 1.416(3) . ?
C1 C2 1.379(3) . ?
C1 C6 1.395(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.379(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(3) . ?
C2 H2 0.9500 . ?
C6 H6 0.9500 . ?
C13 H13 0.9500 . ?
C11 H11 0.9500 . ?
C15 H15a 0.9900 . ?
C15 H15b 0.9900 . ?
C15 C16 1.501(4) . ?
C17 H17a 0.9900 . ?
C17 H17b 0.9900 . ?
C17 C18 1.502(5) . ?
C16 H16a 0.9800 . ?
C16 H16b 0.9800 . ?
C16 H16c 0.9800 . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 0.9800 . ?
O3 C4 1.402(11) . ?
O3 H3a 0.853(19) 4_755 ?
C4 H4a 0.9800 . ?
C4 H4b 0.9800 . ?
C4 H4c 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 H1 109.5 . . ?
C8 N2 N1 114.02(17) . . ?
C7 N1 N2 119.36(17) . . ?
H1a N1 N2 120.9(18) . . ?
H1a N1 C7 119.7(18) . . ?
N1 C7 O2 121.06(18) . . ?
C19 C7 O2 122.73(18) . . ?
C19 C7 N1 116.20(17) . . ?
C15 N3 C12 121.2(2) . . ?
C17 N3 C12 121.3(2) . . ?
C17 N3 C15 117.1(2) . . ?
H8 C8 N2 118.36(12) . . ?
C9 C8 N2 123.27(19) . . ?
C9 C8 H8 118.36(12) . . ?
C3 C19 C7 118.69(19) . . ?
C5 C19 C7 123.04(18) . . ?
C5 C19 C3 118.24(19) . . ?
C14 C9 C8 119.30(19) . . ?
C10 C9 C8 123.11(19) . . ?
C10 C9 C14 117.56(19) . . ?
C13 C12 N3 121.8(2) . . ?
C11 C12 N3 121.1(2) . . ?
C11 C12 C13 117.1(2) . . ?
C2 C1 O1 123.1(2) . . ?
C6 C1 O1 117.3(2) . . ?
C6 C1 C2 119.6(2) . . ?
H14 C14 C9 118.97(12) . . ?
C13 C14 C9 122.1(2) . . ?
C13 C14 H14 118.97(14) . . ?
H3 C3 C19 119.36(12) . . ?
C2 C3 C19 121.3(2) . . ?
C2 C3 H3 119.36(13) . . ?
H5 C5 C19 119.69(12) . . ?
C6 C5 C19 120.6(2) . . ?
C6 C5 H5 119.69(13) . . ?
H10 C10 C9 119.25(12) . . ?
C11 C10 C9 121.5(2) . . ?
C11 C10 H10 119.25(14) . . ?
C3 C2 C1 120.0(2) . . ?
H2 C2 C1 120.01(12) . . ?
H2 C2 C3 120.01(13) . . ?
C5 C6 C1 120.3(2) . . ?
H6 C6 C1 119.87(13) . . ?
H6 C6 C5 119.87(13) . . ?
C14 C13 C12 120.8(2) . . ?
H13 C13 C12 119.59(13) . . ?
H13 C13 C14 119.59(14) . . ?
C10 C11 C12 120.9(2) . . ?
H11 C11 C12 119.55(13) . . ?
H11 C11 C10 119.55(14) . . ?
H15a C15 N3 109.06(14) . . ?
H15b C15 N3 109.06(13) . . ?
H15b C15 H15a 107.8 . . ?
C16 C15 N3 112.7(3) . . ?
C16 C15 H15a 109.06(18) . . ?
C16 C15 H15b 109.06(16) . . ?
H17a C17 N3 109.04(15) . . ?
H17b C17 N3 109.04(14) . . ?
H17b C17 H17a 107.8 . . ?
C18 C17 N3 112.8(3) . . ?
C18 C17 H17a 109.04(19) . . ?
C18 C17 H17b 109.04(16) . . ?
H16a C16 C15 109.5 . . ?
H16b C16 C15 109.5 . . ?
H16b C16 H16a 109.5 . . ?
H16c C16 C15 109.5 . . ?
H16c C16 H16a 109.5 . . ?
H16c C16 H16b 109.5 . . ?
H18a C18 C17 109.5 . . ?
H18b C18 C17 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C17 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
H3a O3 C4 149.4(10) 4_755 . ?
H4a C4 O3 109.5 . . ?
H4b C4 O3 109.5 . . ?
H4b C4 H4a 109.5 . . ?
H4c C4 O3 109.5 . . ?
H4c C4 H4a 109.5 . . ?
H4c C4 H4b 109.5 . . ?
O3 H3a O3 117(5) 4_755 . ?

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
O2 C7 N1 N2 -2.4(2) . . . . ?
O2 C7 C19 C3 -20.9(2) . . . . ?
O2 C7 C19 C5 160.9(2) . . . . ?
O1 C1 C2 C3 -179.6(2) . . . . ?
O1 C1 C6 C5 -179.7(2) . . . . ?
N2 N1 C7 C19 179.10(17) . . . . ?
N2 C8 C9 C14 -175.6(2) . . . . ?
N2 C8 C9 C10 6.4(3) . . . . ?
N1 C7 C19 C3 157.54(19) . . . . ?
N1 C7 C19 C5 -20.6(2) . . . . ?
C7 C19 C3 C2 -176.43(19) . . . . ?
C7 C19 C5 C6 177.0(2) . . . . ?
N3 C12 C13 C14 177.0(2) . . . . ?
N3 C12 C11 C10 -178.3(2) . . . . ?
C8 C9 C14 C13 -178.3(2) . . . . ?
C8 C9 C10 C11 176.9(2) . . . . ?
C19 C3 C2 C1 -0.7(3) . . . . ?
C19 C5 C6 C1 -0.5(3) . . . . ?
C9 C14 C13 C12 1.9(3) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
O3 H3a 1 0.8400 0.0200 -0.0132

loop_
_restr_RIGU_atom_site_label_1
_restr_RIGU_atom_site_label_2
_restr_RIGU_target_weight_param
_restr_RIGU_U13_diff
_restr_RIGU_U23_diff
_restr_RIGU_U33_diff
O2 N1 0.004000 -0.000304 0.007561 -0.000679
O2 C7 0.004000 0.002468 0.002313 -0.002330
O2 C19 0.004000 0.007506 -0.001549 0.000195
O1 C1 0.004000 0.000942 0.001275 -0.000904
O1 C2 0.004000 0.009780 0.001367 -0.003648
O1 C6 0.004000 -0.007849 -0.005999 -0.003354
N2 N1 0.004000 -0.000638 0.000788 -0.000639
N2 C7 0.004000 0.002186 -0.004670 -0.003494
N2 C8 0.004000 0.003237 0.000581 0.000075
N2 C9 0.004000 0.000813 -0.004189 -0.000352
N1 C7 0.004000 -0.000019 -0.002996 -0.001356
N1 C8 0.004000 -0.000136 -0.000243 -0.004198
N1 C19 0.004000 0.001428 -0.002039 -0.001612
C7 C19 0.004000 0.002322 -0.000974 0.000901
C7 C3 0.004000 0.001505 -0.004779 -0.003210
C7 C5 0.004000 0.002928 0.002092 -0.004148
N3 C12 0.004000 0.000297 0.000333 -0.000513
N3 C13 0.004000 -0.004350 0.008696 -0.004218
N3 C11 0.004000 -0.002617 -0.003260 -0.002129
N3 C15 0.004000 -0.004578 0.000892 -0.002144
N3 C17 0.004000 -0.001075 0.010070 -0.000674
N3 C16 0.004000 -0.000974 -0.007540 -0.008114
N3 C18 0.004000 -0.006569 -0.005130 -0.006135
C8 C9 0.004000 -0.001152 -0.003460 0.000607
C8 C14 0.004000 0.002082 -0.002197 -0.002296
C8 C10 0.004000 -0.001265 -0.003959 -0.004282
C19 C3 0.004000 -0.001683 -0.004545 0.000058
C19 C5 0.004000 -0.000582 0.004200 -0.000778
C19 C2 0.004000 -0.002644 -0.005112 0.001233
C19 C6 0.004000 0.001249 0.004311 -0.000488
C9 C14 0.004000 0.004188 -0.000873 -0.001605
C9 C10 0.004000 0.001617 -0.001862 -0.001223
C9 C13 0.004000 0.003045 -0.004108 -0.001103
C9 C11 0.004000 0.002704 -0.002789 0.000542
C12 C14 0.004000 -0.004203 0.008621 0.001335
C12 C10 0.004000 0.000413 -0.003106 0.000512
C12 C13 0.004000 -0.004937 0.006251 -0.000255
C12 C11 0.004000 -0.003395 -0.003434 -0.001333
C12 C15 0.004000 -0.002858 -0.004280 -0.003392
C12 C17 0.004000 0.002082 0.003073 -0.000950
C1 C3 0.004000 0.008658 0.005585 -0.000050
C1 C5 0.004000 -0.004615 -0.005874 0.000445
C1 C2 0.004000 0.007600 0.002872 0.000017
C1 C6 0.004000 0.002716 -0.007266 0.002476
C14 C10 0.004000 0.004223 -0.003121 -0.002028
C14 C13 0.004000 -0.002827 -0.006255 -0.001256
C3 C5 0.004000 0.001465 0.004775 -0.000717
C3 C2 0.004000 0.002846 -0.006969 0.001913
C5 C6 0.004000 -0.002010 0.003042 -0.000065
C10 C11 0.004000 0.003562 0.001967 -0.000752
C2 C6 0.004000 0.009357 -0.003090 0.002343
C13 C11 0.004000 -0.005538 -0.007136 -0.001486
C15 C17 0.004000 -0.010529 0.011575 -0.001607
C15 C16 0.004000 -0.003178 0.001844 -0.004577
C17 C18 0.004000 -0.017033 0.008716 0.001232
O3 C4 0.004000 0.011677 0.001571 0.002659

loop_
_restr_U_rigid_atom_site_label_1
_restr_U_rigid_atom_site_label_2
_restr_U_rigid_target_weight_param
_restr_U_rigid_U_parallel
_restr_U_rigid_diff
O2 N1 0.0100 0.0421 -0.0007
O2 C7 0.0100 0.0410 -0.0023
O2 C19 0.0100 0.0425 0.0002
O1 C1 0.0100 0.0403 -0.0009
O1 C2 0.0100 0.0528 -0.0036
O1 C6 0.0100 0.0421 -0.0034
N2 N1 0.0100 0.0352 -0.0006
N2 C7 0.0100 0.0398 -0.0035
N2 C8 0.0100 0.0469 0.0001
N2 C9 0.0100 0.0396 -0.0004
N1 C7 0.0100 0.0418 -0.0014
N1 C8 0.0100 0.0401 -0.0042
N1 C19 0.0100 0.0381 -0.0016
C7 C19 0.0100 0.0403 0.0009
C7 C3 0.0100 0.0439 -0.0032
C7 C5 0.0100 0.0434 -0.0041
N3 C12 0.0100 0.0396 -0.0005
N3 C13 0.0100 0.0511 -0.0042
N3 C11 0.0100 0.0438 -0.0021
N3 C15 0.0100 0.0659 -0.0021
N3 C17 0.0100 0.0566 -0.0007
N3 C16 0.0100 0.0656 -0.0081
N3 C18 0.0100 0.0620 -0.0061
C8 C9 0.0100 0.0400 0.0006
C8 C14 0.0100 0.0443 -0.0023
C8 C10 0.0100 0.0431 -0.0043
C19 C3 0.0100 0.0434 0.0001
C19 C5 0.0100 0.0462 -0.0008
C19 C2 0.0100 0.0397 0.0012
C19 C6 0.0100 0.0428 -0.0005
C9 C14 0.0100 0.0464 -0.0016
C9 C10 0.0100 0.0495 -0.0012
C9 C13 0.0100 0.0410 -0.0011
C9 C11 0.0100 0.0433 0.0005
C12 C14 0.0100 0.0463 0.0013
C12 C10 0.0100 0.0406 0.0005
C12 C13 0.0100 0.0557 -0.0003
C12 C11 0.0100 0.0499 -0.0013
C12 C15 0.0100 0.0495 -0.0034
C12 C17 0.0100 0.0414 -0.0009
C1 C3 0.0100 0.0479 -0.0001
C1 C5 0.0100 0.0403 0.0004
C1 C2 0.0100 0.0560 0.0000
C1 C6 0.0100 0.0471 0.0025
C14 C10 0.0100 0.0493 -0.0020
C14 C13 0.0100 0.0454 -0.0013
C3 C5 0.0100 0.0439 -0.0007
C3 C2 0.0100 0.0468 0.0019
C5 C6 0.0100 0.0424 -0.0001
C10 C11 0.0100 0.0407 -0.0008
C2 C6 0.0100 0.0478 0.0023
C13 C11 0.0100 0.0520 -0.0015
C15 C17 0.0100 0.0767 -0.0016
C15 C16 0.0100 0.0710 -0.0046
C17 C18 0.0100 0.0858 0.0012
O3 C4 0.0100 0.1033 0.0027

