# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_mjr18056
_audit_block_doi                 10.5517/ccdc.csd.cc1zzs80
_database_code_depnum_ccdc_archive 'CCDC 1846833'
loop_
_audit_author_name
_audit_author_address
'Guang-Shou Feng'
;Dalian Institute of Chemical Physics, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2018-06-02 deposited with the CCDC.	2021-09-14 downloaded from the CCDC.
;
_audit_creation_date             2018-05-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H22 N2 O3 S'
_chemical_formula_sum            'C23 H22 N2 O3 S'
_chemical_formula_weight         406.48
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2924 0.4247 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   14.1925(3)
_cell_length_b                   14.1925(3)
_cell_length_c                   10.5312(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2121.27(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6976
_cell_measurement_temperature    305(2)
_cell_measurement_theta_max      51.165
_cell_measurement_theta_min      3.833
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.863
_exptl_absorpt_coefficient_mu    1.016
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1419 before and 0.0578 after correction. The Ratio of minimum to maximum transmission is 0.8202. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            23362
_diffrn_reflns_point_group_measured_fraction_full 0.917
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.904
_diffrn_reflns_theta_min         3.832
_diffrn_ambient_temperature      304.8
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.825
_reflns_Friedel_fraction_max     0.816
_reflns_number_gt                2839
_reflns_number_total             3691
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 955 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(12)
_refine_ls_extinction_coef       0.0027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3691
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0349P)²+0.1358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0842
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S1 S 0.05441(6) 0.53503(6) 0.74278(8) 0.0505(3) Uani 1 1 d . . . . .
O1 O 0.38187(18) 0.57484(18) 0.7981(2) 0.0620(7) Uani 1 1 d . . . . .
O2 O 0.03640(19) 0.5649(2) 0.8699(2) 0.0708(8) Uani 1 1 d . . . . .
O3 O -0.01778(16) 0.54245(19) 0.6490(3) 0.0610(7) Uani 1 1 d . . . . .
N1 N 0.3170(2) 0.5441(2) 0.6078(3) 0.0506(7) Uani 1 1 d . . . . .
H1 H 0.370719 0.523531 0.582048 0.061 Uiso 1 1 calc R . . . .
N2 N 0.14127(19) 0.5993(2) 0.6914(2) 0.0476(7) Uani 1 1 d . . . . .
C1 C 0.2402(2) 0.5401(2) 0.5168(3) 0.0429(8) Uani 1 1 d . . . . .
H1A H 0.214087 0.476213 0.520134 0.051 Uiso 1 1 calc R . . . .
C2 C 0.1609(2) 0.6083(2) 0.5542(3) 0.0430(8) Uani 1 1 d . . . . .
H2 H 0.104058 0.587078 0.509652 0.052 Uiso 1 1 calc R . . . .
C3 C 0.2225(2) 0.6156(3) 0.7736(3) 0.0527(9) Uani 1 1 d . . . . .
H3A H 0.209329 0.588570 0.856279 0.063 Uiso 1 1 calc R . . . .
H3B H 0.230042 0.683015 0.784947 0.063 Uiso 1 1 calc R . . . .
C4 C 0.3137(2) 0.5760(2) 0.7264(3) 0.0459(8) Uani 1 1 d . . . . .
C5 C 0.2724(2) 0.5571(2) 0.3819(3) 0.0424(8) Uani 1 1 d . . . . .
C6 C 0.3601(3) 0.5893(3) 0.3500(3) 0.0589(10) Uani 1 1 d . . . . .
H6 H 0.405004 0.598900 0.412945 0.071 Uiso 1 1 calc R . . . .
C7 C 0.3823(3) 0.6077(3) 0.2242(4) 0.0666(11) Uani 1 1 d . . . . .
H7 H 0.442396 0.629179 0.203903 0.080 Uiso 1 1 calc R . . . .
C8 C 0.3184(3) 0.5952(3) 0.1305(3) 0.0610(10) Uani 1 1 d . . . . .
H8 H 0.333838 0.608828 0.046621 0.073 Uiso 1 1 calc R . . . .
C9 C 0.2305(3) 0.5620(3) 0.1610(3) 0.0656(11) Uani 1 1 d . . . . .
H9 H 0.186091 0.552491 0.097258 0.079 Uiso 1 1 calc R . . . .
C10 C 0.2076(3) 0.5427(3) 0.2847(3) 0.0578(10) Uani 1 1 d . . . . .
H10 H 0.147948 0.519764 0.304029 0.069 Uiso 1 1 calc R . . . .
C11 C 0.1739(2) 0.7114(2) 0.5211(3) 0.0518(9) Uani 1 1 d . . . . .
C12 C 0.2570(3) 0.7599(3) 0.5349(5) 0.0720(12) Uani 1 1 d . . . . .
H12 H 0.310663 0.728141 0.562028 0.086 Uiso 1 1 calc R . . . .
C13 C 0.2618(4) 0.8553(3) 0.5090(6) 0.1017(16) Uani 1 1 d . . . . .
H13 H 0.318417 0.887291 0.519448 0.122 Uiso 1 1 calc R . . . .
C14 C 0.1842(6) 0.9023(4) 0.4685(6) 0.120(2) Uani 1 1 d . . . . .
H14 H 0.187445 0.966739 0.452911 0.144 Uiso 1 1 calc R . . . .
C15 C 0.1009(5) 0.8549(4) 0.4504(7) 0.126(2) Uani 1 1 d . . . . .
H15 H 0.047885 0.886517 0.420834 0.151 Uiso 1 1 calc R . . . .
C16 C 0.0968(3) 0.7599(3) 0.4766(5) 0.0869(14) Uani 1 1 d . . . . .
H16 H 0.040474 0.727794 0.463850 0.104 Uiso 1 1 calc R . . . .
C17 C 0.0906(2) 0.4171(2) 0.7493(4) 0.0506(8) Uani 1 1 d . . . . .
C18 C 0.1306(3) 0.3818(3) 0.8592(4) 0.0689(11) Uani 1 1 d . . . . .
H18 H 0.137585 0.420279 0.929992 0.083 Uiso 1 1 calc R . . . .
C19 C 0.1600(3) 0.2892(4) 0.8633(5) 0.0831(13) Uani 1 1 d . . . . .
H19 H 0.186045 0.265674 0.937913 0.100 Uiso 1 1 calc R . . . .
C20 C 0.1518(3) 0.2310(3) 0.7601(6) 0.0826(14) Uani 1 1 d . . . . .
C21 C 0.1103(3) 0.2664(3) 0.6513(5) 0.0812(14) Uani 1 1 d . . . . .
H21 H 0.102507 0.227268 0.581299 0.097 Uiso 1 1 calc R . . . .
C22 C 0.0800(3) 0.3595(3) 0.6446(4) 0.0630(11) Uani 1 1 d . . . . .
H22 H 0.052992 0.382604 0.570477 0.076 Uiso 1 1 calc R . . . .
C23 C 0.1843(4) 0.1284(3) 0.7651(9) 0.137(3) Uani 1 1 d . . . . .
H23A H 0.249641 0.124822 0.742065 0.205 Uiso 1 1 calc GR . . . .
H23B H 0.147614 0.091509 0.706879 0.205 Uiso 1 1 calc GR . . . .
H23C H 0.176084 0.104409 0.849655 0.205 Uiso 1 1 calc GR . . . .


_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
S1 O2 1.428(3) . ?
S1 O3 1.427(3) . ?
S1 N2 1.626(3) . ?
S1 C17 1.752(4) . ?
O1 C4 1.228(4) . ?
N1 H1 0.8600 . ?
N1 C1 1.453(4) . ?
N1 C4 1.329(4) . ?
N2 C2 1.477(4) . ?
N2 C3 1.460(4) . ?
C1 H1A 0.9800 . ?
C1 C2 1.536(4) . ?
C1 C5 1.512(4) . ?
C2 H2 0.9800 . ?
C2 C11 1.517(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.496(5) . ?
C5 C6 1.367(5) . ?
C5 C10 1.391(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.352(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.372(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.371(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(5) . ?
C11 C16 1.376(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.356(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.383(5) . ?
C17 C22 1.381(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.380(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.370(7) . ?
C20 C21 1.382(7) . ?
C20 C23 1.529(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.390(6) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
O2 S1 N2 106.33(15) . . ?
O2 S1 C17 107.42(17) . . ?
O3 S1 O2 119.93(17) . . ?
O3 S1 N2 105.81(14) . . ?
O3 S1 C17 107.94(17) . . ?
N2 S1 C17 109.05(15) . . ?
C1 N1 H1 116.3 . . ?
C4 N1 H1 116.3 . . ?
C4 N1 C1 127.3(3) . . ?
C2 N2 S1 121.1(2) . . ?
C3 N2 S1 119.4(2) . . ?
C3 N2 C2 114.7(3) . . ?
N1 C1 H1A 107.2 . . ?
N1 C1 C2 110.9(2) . . ?
N1 C1 C5 112.7(3) . . ?
C2 C1 H1A 107.2 . . ?
C5 C1 H1A 107.2 . . ?
C5 C1 C2 111.2(3) . . ?
N2 C2 C1 109.5(3) . . ?
N2 C2 H2 106.7 . . ?
N2 C2 C11 109.4(3) . . ?
C1 C2 H2 106.7 . . ?
C11 C2 C1 117.3(3) . . ?
C11 C2 H2 106.7 . . ?
N2 C3 H3A 108.5 . . ?
N2 C3 H3B 108.5 . . ?
N2 C3 C4 115.2(3) . . ?
H3A C3 H3B 107.5 . . ?
C4 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
O1 C4 N1 123.1(3) . . ?
O1 C4 C3 118.8(3) . . ?
N1 C4 C3 118.1(3) . . ?
C6 C5 C1 124.0(3) . . ?
C6 C5 C10 118.0(3) . . ?
C10 C5 C1 117.9(3) . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.3(3) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.3(4) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C5 C10 H10 119.5 . . ?
C9 C10 C5 120.9(3) . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C2 124.4(3) . . ?
C12 C11 C16 118.0(4) . . ?
C16 C11 C2 117.6(3) . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.8(4) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.3(5) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0(5) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.2(5) . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 121.6(5) . . ?
C11 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C18 C17 S1 120.0(3) . . ?
C22 C17 S1 120.2(3) . . ?
C22 C17 C18 119.8(4) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.7(4) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.5(5) . . ?
C20 C19 H19 119.2 . . ?
C19 C20 C21 118.4(4) . . ?
C19 C20 C23 121.4(6) . . ?
C21 C20 C23 120.3(6) . . ?
C20 C21 H21 119.4 . . ?
C20 C21 C22 121.3(5) . . ?
C22 C21 H21 119.4 . . ?
C17 C22 C21 119.2(4) . . ?
C17 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_d8v20299_0m
_database_code_depnum_ccdc_archive 'CCDC 2023354'
_audit_update_record             
;
2020-08-14 deposited with the CCDC.	2021-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 N2 O2'
_chemical_formula_weight         278.30

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      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                   6.1923(2)
_cell_length_b                   9.0465(3)
_cell_length_c                   13.1134(4)
_cell_angle_alpha                106.2360(10)
_cell_angle_beta                 98.2550(10)
_cell_angle_gamma                94.1460(10)
_cell_volume                     693.09(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6899
_cell_measurement_theta_min      4.723
_cell_measurement_theta_max      54.890

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6086
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            17265
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.361
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2704
_reflns_number_gt                2211
_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-2013 (Sheldrick, 2013)'
_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)+(0.0640P)²+0.1339P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.088(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2704
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1310
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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 0.95063(18) 0.63177(14) 0.60858(9) 0.0534(3) Uani 1 1 d . . . . .
O2 O -0.1737(2) 0.96595(18) 0.16486(11) 0.0767(5) Uani 1 1 d . . . . .
N1 N 0.7414(2) 0.57391(15) 0.44104(10) 0.0395(3) Uani 1 1 d . . . . .
N2 N 0.4820(2) 0.79432(15) 0.51714(10) 0.0445(3) Uani 1 1 d . . . . .
C1 C 0.7911(2) 0.65508(18) 0.54778(12) 0.0411(4) Uani 1 1 d . . . . .
C2 C 0.6415(3) 0.76544(19) 0.58147(12) 0.0454(4) Uani 1 1 d . . . . .
H2 H 0.6602 0.8199 0.6543 0.054 Uiso 1 1 calc R U . . .
C3 C 0.4470(2) 0.71569(17) 0.40865(11) 0.0382(4) Uani 1 1 d . . . . .
C4 C 0.5738(2) 0.60089(17) 0.37014(11) 0.0373(3) Uani 1 1 d . . . . .
C5 C 0.5486(2) 0.49970(17) 0.25704(11) 0.0386(4) Uani 1 1 d . . . . .
C6 C 0.3505(3) 0.41016(19) 0.20614(12) 0.0457(4) Uani 1 1 d . . . . .
H6 H 0.2330 0.4110 0.2431 0.055 Uiso 1 1 calc R U . . .
C7 C 0.3284(3) 0.3195(2) 0.10000(13) 0.0548(5) Uani 1 1 d . . . . .
H7 H 0.1963 0.2585 0.0661 0.066 Uiso 1 1 calc R U . . .
C8 C 0.5011(3) 0.3193(2) 0.04430(13) 0.0585(5) Uani 1 1 d . . . . .
H8 H 0.4845 0.2598 -0.0274 0.070 Uiso 1 1 calc R U . . .
C9 C 0.6977(3) 0.4071(2) 0.09479(13) 0.0560(5) Uani 1 1 d . . . . .
H9 H 0.8141 0.4068 0.0572 0.067 Uiso 1 1 calc R U . . .
C10 C 0.7234(3) 0.49600(19) 0.20117(12) 0.0455(4) Uani 1 1 d . . . . .
H10 H 0.8580 0.5534 0.2354 0.055 Uiso 1 1 calc R U . . .
C11 C 0.2765(2) 0.77201(17) 0.34200(12) 0.0395(4) Uani 1 1 d . . . . .
C12 C 0.1046(2) 0.83953(18) 0.38771(13) 0.0435(4) Uani 1 1 d . . . . .
H12 H 0.0929 0.8410 0.4579 0.052 Uiso 1 1 calc R U . . .
C13 C -0.0495(3) 0.90446(19) 0.33177(14) 0.0496(4) Uani 1 1 d . . . . .
H13 H -0.1630 0.9484 0.3642 0.060 Uiso 1 1 calc R U . . .
C14 C -0.0341(3) 0.90385(19) 0.22752(13) 0.0502(4) Uani 1 1 d . . . . .
C15 C 0.1354(3) 0.8367(2) 0.18036(14) 0.0552(5) Uani 1 1 d . . . . .
H15 H 0.1466 0.8354 0.1102 0.066 Uiso 1 1 calc R U . . .
C16 C 0.2875(3) 0.7719(2) 0.23666(13) 0.0491(4) Uani 1 1 d . . . . .
H16 H 0.3999 0.7272 0.2036 0.059 Uiso 1 1 calc R U . . .
C17 C -0.3104(4) 1.0708(2) 0.2153(2) 0.0768(7) Uani 1 1 d . . . . .
H17A H -0.3897 1.1122 0.1632 0.115 Uiso 1 1 calc R U . . .
H17B H -0.2223 1.1538 0.2716 0.115 Uiso 1 1 calc R U . . .
H17C H -0.4126 1.0179 0.2456 0.115 Uiso 1 1 calc R U . . .
H1 H 0.833(3) 0.501(2) 0.4193(14) 0.052(5) 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 1.2467(18) . ?
O2 C14 1.365(2) . ?
O2 C17 1.407(2) . ?
N1 C1 1.3645(19) . ?
N1 C4 1.3739(18) . ?
N1 H1 0.91(2) . ?
N2 C2 1.295(2) . ?
N2 C3 1.3784(19) . ?
C1 C2 1.433(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(2) . ?
C3 C11 1.483(2) . ?
C4 C5 1.489(2) . ?
C5 C6 1.388(2) . ?
C5 C10 1.389(2) . ?
C6 C7 1.385(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.392(2) . ?
C11 C16 1.393(2) . ?
C12 C13 1.383(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(2) . ?
C15 C16 1.378(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C14 O2 C17 118.30(16) . . ?
C1 N1 C4 123.95(13) . . ?
C1 N1 H1 114.2(11) . . ?
C4 N1 H1 121.8(11) . . ?
C2 N2 C3 119.91(13) . . ?
O1 C1 N1 122.04(14) . . ?
O1 C1 C2 124.49(14) . . ?
N1 C1 C2 113.46(13) . . ?
N2 C2 C1 124.27(14) . . ?
N2 C2 H2 117.9 . . ?
C1 C2 H2 117.9 . . ?
C4 C3 N2 119.82(13) . . ?
C4 C3 C11 125.54(13) . . ?
N2 C3 C11 114.55(13) . . ?
N1 C4 C3 118.35(13) . . ?
N1 C4 C5 115.26(13) . . ?
C3 C4 C5 126.39(13) . . ?
C6 C5 C10 119.49(14) . . ?
C6 C5 C4 120.53(13) . . ?
C10 C5 C4 119.97(13) . . ?
C7 C6 C5 119.74(15) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C8 C7 C6 120.41(16) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 119.90(15) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.36(16) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C5 120.07(15) . . ?
C9 C10 H10 120.0 . . ?
C5 C10 H10 120.0 . . ?
C12 C11 C16 117.17(14) . . ?
C12 C11 C3 119.55(13) . . ?
C16 C11 C3 123.09(13) . . ?
C13 C12 C11 121.93(15) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C14 C13 C12 119.80(15) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
O2 C14 C13 125.24(15) . . ?
O2 C14 C15 115.56(15) . . ?
C13 C14 C15 119.19(15) . . ?
C16 C15 C14 120.53(15) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 121.37(15) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C4 N1 C1 O1 -176.76(14) . . . . ?
C4 N1 C1 C2 4.1(2) . . . . ?
C3 N2 C2 C1 0.5(2) . . . . ?
O1 C1 C2 N2 176.70(15) . . . . ?
N1 C1 C2 N2 -4.2(2) . . . . ?
C2 N2 C3 C4 3.6(2) . . . . ?
C2 N2 C3 C11 -173.25(14) . . . . ?
C1 N1 C4 C3 -0.4(2) . . . . ?
C1 N1 C4 C5 179.63(13) . . . . ?
N2 C3 C4 N1 -3.6(2) . . . . ?
C11 C3 C4 N1 172.87(13) . . . . ?
N2 C3 C4 C5 176.31(14) . . . . ?
C11 C3 C4 C5 -7.2(2) . . . . ?
N1 C4 C5 C6 123.31(15) . . . . ?
C3 C4 C5 C6 -56.6(2) . . . . ?
N1 C4 C5 C10 -57.55(19) . . . . ?
C3 C4 C5 C10 122.53(17) . . . . ?
C10 C5 C6 C7 -0.7(2) . . . . ?
C4 C5 C6 C7 178.45(14) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C6 C7 C8 C9 1.2(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C5 -1.4(3) . . . . ?
C6 C5 C10 C9 1.8(2) . . . . ?
C4 C5 C10 C9 -177.32(14) . . . . ?
C4 C3 C11 C12 154.61(15) . . . . ?
N2 C3 C11 C12 -28.7(2) . . . . ?
C4 C3 C11 C16 -30.5(2) . . . . ?
N2 C3 C11 C16 146.14(16) . . . . ?
C16 C11 C12 C13 -0.1(2) . . . . ?
C3 C11 C12 C13 175.05(14) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C17 O2 C14 C13 16.5(3) . . . . ?
C17 O2 C14 C15 -163.10(18) . . . . ?
C12 C13 C14 O2 -179.05(16) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
O2 C14 C15 C16 179.31(16) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
C12 C11 C16 C15 0.4(2) . . . . ?
C3 C11 C16 C15 -174.64(16) . . . . ?

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
N1 H1 O1 0.91(2) 1.87(2) 2.7776(18) 171.9(17) 2_766
C17 H17B O1 0.96 2.47 3.423(3) 169.3 2_676

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-4

