# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_GL-100K
_database_code_depnum_ccdc_archive 'CCDC 2106413'
loop_
_audit_author_name
_audit_author_address
'Shurong Ban'
;Shanxi Medical University
China
;
_audit_update_record             
;
2021-08-30 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21H14ClN3O3, CH2Cl2, H2O'
_chemical_formula_sum            'C22 H18 Cl3 N3 O4'
_chemical_formula_weight         494.74

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'
Cl Cl 0.3639 0.7018 '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                   14.82704(11)
_cell_length_b                   9.94081(7)
_cell_length_c                   14.20343(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.8125(7)
_cell_angle_gamma                90
_cell_volume                     2088.85(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4291
_cell_measurement_theta_min      5.361
_cell_measurement_theta_max      75.932

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    4.298
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_process_details   ' Higashi, T. (1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ωκ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23668
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.361
_diffrn_reflns_theta_max         75.932
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4291
_reflns_number_gt                4106
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1500P)²+1.2000P] 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_number_reflns         4291
_refine_ls_number_parameters     328
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0718
_refine_ls_wR_factor_ref         0.2334
_refine_ls_wR_factor_gt          0.2303
_refine_ls_goodness_of_fit_ref   1.255
_refine_ls_restrained_S_all      1.279
_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 -0.02909(11) 0.71711(17) 0.52775(11) 0.0224(4) Uani 1 1 d . . . . .
O2 O -0.09996(11) 0.90022(16) 0.23790(11) 0.0206(4) Uani 1 1 d . . . . .
O3 O 0.18979(17) 0.67662(19) 0.53565(14) 0.0412(6) Uani 1 1 d . . . . .
O4 O 0.13895(13) 0.94221(17) 0.51984(12) 0.0265(4) Uani 1 1 d D . . . .
N1 N -0.06894(13) 0.83618(18) 0.39209(13) 0.0180(4) Uani 1 1 d . . . . .
N2 N 0.19172(14) 0.47278(19) 0.46299(14) 0.0198(4) Uani 1 1 d . . . . .
N3 N -0.11740(14) 0.5321(2) 0.17190(14) 0.0220(4) Uani 1 1 d . . . . .
C1 C -0.03001(14) 0.7304(2) 0.44363(15) 0.0169(4) Uani 1 1 d . . . . .
C2 C -0.06708(14) 0.8233(2) 0.29652(15) 0.0159(4) Uani 1 1 d . . . . .
C3 C -0.01419(14) 0.6937(2) 0.27574(14) 0.0148(4) Uani 1 1 d . . . . .
C4 C 0.01422(14) 0.6365(2) 0.37488(14) 0.0155(4) Uani 1 1 d . . . . .
H4A H -0.0048 0.5407 0.3820 0.019 Uiso 1 1 calc R U . . .
C5 C 0.11582(15) 0.6526(2) 0.38190(15) 0.0163(4) Uani 1 1 d . . . . .
C6 C 0.14765(14) 0.7031(2) 0.30382(15) 0.0160(4) Uani 1 1 d . . . . .
C7 C 0.07467(14) 0.7255(2) 0.22701(14) 0.0158(4) Uani 1 1 d . . . . .
H7A H 0.0821 0.6641 0.1731 0.019 Uiso 1 1 calc R U . . .
H7B H 0.0750 0.8195 0.2042 0.019 Uiso 1 1 calc R U . . .
C8 C 0.24367(15) 0.7294(2) 0.28666(15) 0.0185(5) Uani 1 1 d . . . . .
C9 C 0.28201(16) 0.6677(3) 0.21043(17) 0.0259(5) Uani 1 1 d . . . . .
H9A H 0.2475 0.6063 0.1715 0.031 Uiso 1 1 calc R U . . .
C10 C 0.37077(18) 0.6965(4) 0.1918(2) 0.0381(7) Uani 1 1 d . . . . .
H10A H 0.3966 0.6544 0.1399 0.046 Uiso 1 1 calc R U . . .
C11 C 0.42226(18) 0.7858(4) 0.2477(2) 0.0386(7) Uani 1 1 d . . . . .
H11A H 0.4830 0.8053 0.2349 0.046 Uiso 1 1 calc R U . . .
C12 C 0.38285(17) 0.8459(3) 0.3227(2) 0.0311(6) Uani 1 1 d . . . . .
C13 C 0.29496(16) 0.8184(2) 0.34387(17) 0.0239(5) Uani 1 1 d . . . . .
H13A H 0.2700 0.8596 0.3966 0.029 Uiso 1 1 calc R U . . .
C14 C 0.17041(15) 0.6040(2) 0.46782(15) 0.0180(5) Uani 1 1 d . . . . .
C15 C 0.23584(15) 0.3907(2) 0.53321(16) 0.0208(5) Uani 1 1 d . . . . .
C16 C 0.25955(17) 0.2607(2) 0.50545(18) 0.0251(5) Uani 1 1 d . . . . .
H16A H 0.2475 0.2330 0.4418 0.030 Uiso 1 1 calc R U . . .
C17 C 0.30055(17) 0.1726(2) 0.5707(2) 0.0291(6) Uani 1 1 d . . . . .
H17A H 0.3165 0.0846 0.5517 0.035 Uiso 1 1 calc R U . . .
C18 C 0.31840(18) 0.2127(3) 0.6640(2) 0.0314(6) Uani 1 1 d . . . . .
H18A H 0.3464 0.1523 0.7088 0.038 Uiso 1 1 calc R U . . .
C19 C 0.2951(2) 0.3414(3) 0.69111(19) 0.0319(6) Uani 1 1 d . . . . .
H19A H 0.3074 0.3688 0.7547 0.038 Uiso 1 1 calc R U . . .
C20 C 0.25372(19) 0.4312(3) 0.62644(17) 0.0272(5) Uani 1 1 d . . . . .
H20A H 0.2379 0.5191 0.6457 0.033 Uiso 1 1 calc R U . . .
C21 C -0.07280(14) 0.6043(2) 0.21761(14) 0.0164(5) Uani 1 1 d . . . . .
H4B H 0.133(3) 0.963(4) 0.4607(15) 0.051(11) Uiso 1 1 d D . . . .
H4C H 0.149(3) 0.857(2) 0.525(3) 0.055(12) Uiso 1 1 d D . . . .
Cl1 Cl 0.44475(5) 0.96179(9) 0.39293(6) 0.0502(3) Uani 1 1 d . . . . .
C22A C 0.5656(5) 1.0968(7) 0.0182(5) 0.0273(15) Uani 0.375(4) 1 d D U P A 1
H22A H 0.6165 1.1614 0.0228 0.033 Uiso 0.375(4) 1 calc R U P A 1
H22B H 0.5743 1.0422 -0.0388 0.033 Uiso 0.375(4) 1 calc R U P A 1
Cl2A Cl 0.58697(13) 0.9921(2) 0.10728(14) 0.0371(7) Uani 0.375(4) 1 d D U P A 1
Cl3A Cl 0.48239(18) 1.1829(3) -0.0084(2) 0.0628(10) Uani 0.375(4) 1 d D U P A 1
C22B C 0.4971(3) 1.0809(5) 0.0767(4) 0.0468(15) Uani 0.625(4) 1 d D . P A 2
H22C H 0.4929 1.1584 0.1199 0.056 Uiso 0.625(4) 1 calc R U P A 2
H22D H 0.4366 1.0392 0.0659 0.056 Uiso 0.625(4) 1 calc R U P A 2
Cl2B Cl 0.5740(15) 0.968(2) 0.1195(14) 0.553(17) Uani 0.625(4) 1 d D U P A 2
Cl3B Cl 0.5391(10) 1.1283(17) -0.0268(9) 0.342(6) Uiso 0.625(4) 1 d D . P A 2
H1A H -0.092(3) 0.919(4) 0.421(3) 0.037(9) Uiso 1 1 d . . . . .
H2A H 0.174(2) 0.433(3) 0.413(2) 0.021(7) 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
O1 C1 1.201(3) . ?
O2 C2 1.209(3) . ?
O3 C14 1.223(3) . ?
N1 C2 1.366(3) . ?
N1 C1 1.385(3) . ?
N2 C14 1.345(3) . ?
N2 C15 1.415(3) . ?
N3 C21 1.147(3) . ?
C1 C4 1.530(3) . ?
C2 C3 1.546(3) . ?
C3 C21 1.460(3) . ?
C3 C4 1.551(3) . ?
C3 C7 1.561(3) . ?
C4 C5 1.512(3) . ?
C5 C6 1.332(3) . ?
C5 C14 1.499(3) . ?
C6 C8 1.483(3) . ?
C6 C7 1.501(3) . ?
C8 C13 1.393(3) . ?
C8 C9 1.397(3) . ?
C9 C10 1.389(4) . ?
C10 C11 1.386(4) . ?
C11 C12 1.384(4) . ?
C12 C13 1.384(4) . ?
C12 Cl1 1.744(3) . ?
C15 C20 1.393(3) . ?
C15 C16 1.402(3) . ?
C16 C17 1.386(3) . ?
C17 C18 1.393(4) . ?
C18 C19 1.387(4) . ?
C19 C20 1.393(3) . ?
C22A Cl3A 1.529(7) . ?
C22A Cl2A 1.652(6) . ?
Cl2A Cl3A 2.422(4) 3_675 ?
Cl3A Cl2A 2.422(4) 3_675 ?
C22B Cl2B 1.683(15) . ?
C22B Cl3B 1.701(12) . ?
Cl2B Cl3B 2.27(3) 3_675 ?
Cl3B Cl2B 2.27(3) 3_675 ?

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 N1 C1 114.74(18) . . ?
C14 N2 C15 128.5(2) . . ?
O1 C1 N1 125.8(2) . . ?
O1 C1 C4 126.2(2) . . ?
N1 C1 C4 107.90(17) . . ?
O2 C2 N1 126.2(2) . . ?
O2 C2 C3 125.58(19) . . ?
N1 C2 C3 108.19(17) . . ?
C21 C3 C2 108.95(17) . . ?
C21 C3 C4 113.92(17) . . ?
C2 C3 C4 104.05(16) . . ?
C21 C3 C7 111.14(16) . . ?
C2 C3 C7 111.72(16) . . ?
C4 C3 C7 106.89(16) . . ?
C5 C4 C1 111.14(17) . . ?
C5 C4 C3 103.31(16) . . ?
C1 C4 C3 104.69(16) . . ?
C6 C5 C14 126.7(2) . . ?
C6 C5 C4 113.07(19) . . ?
C14 C5 C4 120.09(18) . . ?
C5 C6 C8 126.9(2) . . ?
C5 C6 C7 112.50(19) . . ?
C8 C6 C7 120.52(19) . . ?
C6 C7 C3 103.70(16) . . ?
C13 C8 C9 119.7(2) . . ?
C13 C8 C6 120.6(2) . . ?
C9 C8 C6 119.6(2) . . ?
C10 C9 C8 119.8(2) . . ?
C11 C10 C9 121.0(2) . . ?
C12 C11 C10 118.2(2) . . ?
C11 C12 C13 122.2(2) . . ?
C11 C12 Cl1 119.5(2) . . ?
C13 C12 Cl1 118.3(2) . . ?
C12 C13 C8 119.0(2) . . ?
O3 C14 N2 124.7(2) . . ?
O3 C14 C5 122.5(2) . . ?
N2 C14 C5 112.78(19) . . ?
C20 C15 C16 119.9(2) . . ?
C20 C15 N2 123.6(2) . . ?
C16 C15 N2 116.5(2) . . ?
C17 C16 C15 120.1(2) . . ?
C16 C17 C18 120.2(2) . . ?
C19 C18 C17 119.6(2) . . ?
C18 C19 C20 121.0(3) . . ?
C19 C20 C15 119.3(2) . . ?
N3 C21 C3 178.6(2) . . ?
Cl3A C22A Cl2A 130.7(5) . . ?
C22A Cl2A Cl3A 87.5(2) . 3_675 ?
C22A Cl3A Cl2A 92.6(3) . 3_675 ?
Cl2B C22B Cl3B 102.6(8) . . ?
C22B Cl2B Cl3B 67.4(9) . 3_675 ?
C22B Cl3B Cl2B 94.9(9) . 3_675 ?

_refine_diff_density_max         1.181
_refine_diff_density_min         -1.259
_refine_diff_density_rms         0.106

####################################################################### 
# 
# 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_NZGS-BSR-GL-426-100K
_database_code_depnum_ccdc_archive 'CCDC 2114587'
loop_
_audit_author_name
_audit_author_address
'shurong ban'
;shanxi medical university
China
;
_audit_update_record             
;
2021-10-08 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 N3 O3'
_chemical_formula_sum            'C21 H15 N3 O3'
_chemical_formula_weight         357.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           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                   13.28270(10)
_cell_length_b                   11.37750(10)
_cell_length_c                   12.23180(10)
_cell_angle_alpha                90
_cell_angle_beta                 116.1210(10)
_cell_angle_gamma                90
_cell_volume                     1659.72(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3406
_cell_measurement_theta_min      3.706
_cell_measurement_theta_max      75.889

_exptl_crystal_description       bulk
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.802
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   ' Higashi, T. (1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ωκ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17933
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.706
_diffrn_reflns_theta_max         75.889
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3406
_reflns_number_gt                3216
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0589P)²+0.6540P] 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_number_reflns         3406
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1019
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.66645(7) 0.67528(7) 0.15190(8) 0.0201(2) Uani 1 1 d . . . . .
O2 O 0.62454(7) 1.06614(7) 0.05259(8) 0.0197(2) Uani 1 1 d . . . . .
O3 O 0.87240(7) 0.96002(7) 0.12309(7) 0.01539(18) Uani 1 1 d . . . . .
N1 N 0.63306(8) 0.87457(9) 0.11861(9) 0.0160(2) Uani 1 1 d . . . . .
N2 N 0.91208(10) 0.54997(9) 0.09047(10) 0.0257(2) Uani 1 1 d . . . . .
N3 N 0.93499(8) 0.81711(9) 0.27769(9) 0.0197(2) Uani 1 1 d . . . . .
H3B H 0.9581(14) 0.8824(16) 0.3254(16) 0.031(4) Uiso 1 1 d . . . . .
C1 C 0.49970(10) 0.82191(11) 0.19655(11) 0.0204(3) Uani 1 1 d . . . . .
H1A H 0.4734 0.7616 0.1395 0.025 Uiso 1 1 calc R U . . .
C2 C 0.45229(10) 0.84135(12) 0.27599(12) 0.0241(3) Uani 1 1 d . . . . .
H2A H 0.3946 0.7932 0.2731 0.029 Uiso 1 1 calc R U . . .
C3 C 0.49079(11) 0.93235(12) 0.35943(12) 0.0257(3) Uani 1 1 d . . . . .
H3A H 0.4574 0.9468 0.4109 0.031 Uiso 1 1 calc R U . . .
C4 C 0.57915(12) 1.00203(11) 0.36641(12) 0.0254(3) Uani 1 1 d . . . . .
H4A H 0.6058 1.0620 0.4238 0.030 Uiso 1 1 calc R U . . .
C5 C 0.62824(11) 0.98302(11) 0.28834(11) 0.0215(3) Uani 1 1 d . . . . .
H5A H 0.6877 1.0294 0.2932 0.026 Uiso 1 1 calc R U . . .
C6 C 0.58684(9) 0.89359(10) 0.20321(10) 0.0171(2) Uani 1 1 d . . . . .
C7 C 0.66773(9) 0.76448(10) 0.09870(10) 0.0157(2) Uani 1 1 d . . . . .
C8 C 0.71058(9) 0.77846(10) 0.00355(10) 0.0153(2) Uani 1 1 d . . . . .
H8A H 0.6720 0.7254 -0.0656 0.018 Uiso 1 1 calc R U . . .
C9 C 0.69152(9) 0.90840(10) -0.03585(10) 0.0150(2) Uani 1 1 d . . . . .
H9A H 0.6388 0.9166 -0.1221 0.018 Uiso 1 1 calc R U . . .
C10 C 0.64611(9) 0.96415(10) 0.04644(10) 0.0156(2) Uani 1 1 d . . . . .
C11 C 0.81160(9) 0.95099(10) -0.01021(10) 0.0142(2) Uani 1 1 d . . . . .
C12 C 0.86307(10) 0.84000(10) -0.03555(10) 0.0164(2) Uani 1 1 d . . . . .
H12A H 0.9422 0.8484 -0.0143 0.020 Uiso 1 1 calc R U . . .
H12B H 0.8225 0.8118 -0.1185 0.020 Uiso 1 1 calc R U . . .
C13 C 0.84093(9) 0.76623(10) 0.05726(10) 0.0156(2) Uani 1 1 d . . . . .
C14 C 0.82194(9) 1.06326(10) -0.06874(10) 0.0151(2) Uani 1 1 d . . . . .
C15 C 0.83071(10) 1.17142(10) -0.01216(11) 0.0190(2) Uani 1 1 d . . . . .
H15A H 0.8301 1.1751 0.0635 0.023 Uiso 1 1 calc R U . . .
C16 C 0.84043(10) 1.27408(10) -0.06854(11) 0.0202(2) Uani 1 1 d . . . . .
H16A H 0.8469 1.3461 -0.0301 0.024 Uiso 1 1 calc R U . . .
C17 C 0.84056(10) 1.26940(10) -0.18213(11) 0.0189(2) Uani 1 1 d . . . . .
H17A H 0.8467 1.3382 -0.2199 0.023 Uiso 1 1 calc R U . . .
C18 C 0.83153(10) 1.16158(11) -0.23880(11) 0.0195(3) Uani 1 1 d . . . . .
H18A H 0.8314 1.1582 -0.3148 0.023 Uiso 1 1 calc R U . . .
C19 C 0.82267(10) 1.05856(10) -0.18240(11) 0.0178(2) Uani 1 1 d . . . . .
H19A H 0.8172 0.9865 -0.2205 0.021 Uiso 1 1 calc R U . . .
C20 C 0.89049(9) 0.84698(10) 0.16807(10) 0.0154(2) Uani 1 1 d . . . . .
C21 C 0.88177(10) 0.64536(10) 0.07848(11) 0.0190(2) 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
O1 C7 1.2096(14) . ?
O2 C10 1.2055(14) . ?
O3 C20 1.3778(13) . ?
O3 C11 1.4704(13) . ?
N1 C7 1.3926(15) . ?
N1 C10 1.4082(14) . ?
N1 C6 1.4332(14) . ?
N2 C21 1.1444(17) . ?
N3 C20 1.2509(15) . ?
N3 H3B 0.911(18) . ?
C1 C6 1.3886(17) . ?
C1 C2 1.3888(17) . ?
C1 H1A 0.9300 . ?
C2 C3 1.384(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.387(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.3899(17) . ?
C4 H4A 0.9300 . ?
C5 C6 1.3848(17) . ?
C5 H5A 0.9300 . ?
C7 C8 1.5123(15) . ?
C8 C9 1.5410(15) . ?
C8 C13 1.5644(15) . ?
C8 H8A 0.9800 . ?
C9 C10 1.5211(15) . ?
C9 C11 1.5611(15) . ?
C9 H9A 0.9800 . ?
C11 C14 1.4998(15) . ?
C11 C12 1.5313(15) . ?
C12 C13 1.5407(15) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C21 1.4590(16) . ?
C13 C20 1.5261(15) . ?
C14 C15 1.3914(16) . ?
C14 C19 1.3955(16) . ?
C15 C16 1.3909(16) . ?
C15 H15A 0.9300 . ?
C16 C17 1.3913(17) . ?
C16 H16A 0.9300 . ?
C17 C18 1.3880(17) . ?
C17 H17A 0.9300 . ?
C18 C19 1.3911(16) . ?
C18 H18A 0.9300 . ?
C19 H19A 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
C20 O3 C11 106.96(8) . . ?
C7 N1 C10 113.57(9) . . ?
C7 N1 C6 122.81(10) . . ?
C10 N1 C6 123.61(10) . . ?
C20 N3 H3B 109.4(11) . . ?
C6 C1 C2 119.24(12) . . ?
C6 C1 H1A 120.4 . . ?
C2 C1 H1A 120.4 . . ?
C3 C2 C1 120.06(12) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 120.05(12) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 C5 120.58(12) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C6 C5 C4 118.67(12) . . ?
C6 C5 H5A 120.7 . . ?
C4 C5 H5A 120.7 . . ?
C5 C6 C1 121.36(11) . . ?
C5 C6 N1 119.96(10) . . ?
C1 C6 N1 118.68(11) . . ?
O1 C7 N1 125.20(11) . . ?
O1 C7 C8 126.97(10) . . ?
N1 C7 C8 107.78(9) . . ?
C7 C8 C9 106.02(9) . . ?
C7 C8 C13 112.92(9) . . ?
C9 C8 C13 102.46(8) . . ?
C7 C8 H8A 111.7 . . ?
C9 C8 H8A 111.7 . . ?
C13 C8 H8A 111.7 . . ?
C10 C9 C8 104.57(9) . . ?
C10 C9 C11 113.91(9) . . ?
C8 C9 C11 102.85(8) . . ?
C10 C9 H9A 111.7 . . ?
C8 C9 H9A 111.7 . . ?
C11 C9 H9A 111.7 . . ?
O2 C10 N1 124.00(10) . . ?
O2 C10 C9 128.11(10) . . ?
N1 C10 C9 107.89(9) . . ?
O3 C11 C14 110.41(9) . . ?
O3 C11 C12 101.88(8) . . ?
C14 C11 C12 117.57(9) . . ?
O3 C11 C9 104.96(8) . . ?
C14 C11 C9 117.95(9) . . ?
C12 C11 C9 102.18(9) . . ?
C11 C12 C13 93.04(8) . . ?
C11 C12 H12A 113.1 . . ?
C13 C12 H12A 113.1 . . ?
C11 C12 H12B 113.1 . . ?
C13 C12 H12B 113.1 . . ?
H12A C12 H12B 110.5 . . ?
C21 C13 C20 115.36(10) . . ?
C21 C13 C12 117.90(10) . . ?
C20 C13 C12 100.30(9) . . ?
C21 C13 C8 114.50(9) . . ?
C20 C13 C8 106.52(9) . . ?
C12 C13 C8 100.20(9) . . ?
C15 C14 C19 119.58(11) . . ?
C15 C14 C11 121.40(10) . . ?
C19 C14 C11 119.02(10) . . ?
C16 C15 C14 120.12(11) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C15 C16 C17 120.28(11) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C18 C17 C16 119.65(11) . . ?
C18 C17 H17A 120.2 . . ?
C16 C17 H17A 120.2 . . ?
C17 C18 C19 120.31(11) . . ?
C17 C18 H18A 119.8 . . ?
C19 C18 H18A 119.8 . . ?
C18 C19 C14 120.06(11) . . ?
C18 C19 H19A 120.0 . . ?
C14 C19 H19A 120.0 . . ?
N3 C20 O3 126.78(11) . . ?
N3 C20 C13 127.15(11) . . ?
O3 C20 C13 106.03(9) . . ?
N2 C21 C13 177.42(13) . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.045

