# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_20180930a
_database_code_depnum_ccdc_archive 'CCDC 1902832'
loop_
_audit_author_name
_audit_author_address
'Jitan Zhang'
;Anhui Normal University
China
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-06-18 downloaded from the CCDC.
;
_audit_creation_date             2019-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H20 F N O4 S'
_chemical_formula_sum            'C29 H20 F N O4 S'
_chemical_formula_weight         497.52
_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 0.0033 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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.8851(5)
_cell_length_b                   14.7661(7)
_cell_length_c                   14.9956(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.0080(10)
_cell_angle_gamma                90
_cell_volume                     2742.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9653
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      3.10
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6441
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1038
_diffrn_reflns_av_unetI/netI     0.1150
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21724
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.808
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2526
_reflns_number_total             4790
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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         0.303
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4790
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1870
_refine_ls_R_factor_gt           0.1182
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1572P)²+1.0739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2800
_refine_ls_wR_factor_ref         0.3161
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C8(H8), C28(H28), C4(H4), C18(H18), C13(H13), C12(H12), C25(H25),
 C3(H3), C7(H7), C29(H29), C21(H21), C14(H14), C20(H20), C22(H22), C26(H26),
 C6(H6)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.58636(12) 0.27803(10) 0.77324(11) 0.0599(5) Uani 1 1 d . . . . .
F1 F 0.0975(3) 0.5403(3) 1.2046(3) 0.1043(14) Uani 1 1 d . . . . .
O3 O 0.3868(4) 0.5793(3) 0.9482(3) 0.0739(13) Uani 1 1 d . . . . .
O4 O 0.1718(4) 0.5521(3) 0.8091(3) 0.0818(14) Uani 1 1 d . . . . .
O1 O 0.5293(3) 0.2297(3) 0.6930(3) 0.0730(12) Uani 1 1 d . . . . .
O2 O 0.6776(3) 0.3325(3) 0.7721(3) 0.0750(13) Uani 1 1 d . . . . .
N1 N 0.4990(3) 0.3516(3) 0.7975(3) 0.0514(12) Uani 1 1 d . . . . .
C10 C 0.3557(4) 0.4110(3) 0.8366(3) 0.0427(12) Uani 1 1 d . . . . .
C9 C 0.4395(4) 0.4789(4) 0.8507(4) 0.0470(13) Uani 1 1 d . . . . .
C24 C 0.1702(4) 0.5043(3) 0.9586(4) 0.0457(13) Uani 1 1 d . . . . .
C23 C 0.1964(4) 0.4951(4) 0.8698(4) 0.0548(15) Uani 1 1 d . . . . .
C19 C 0.6041(5) 0.7216(5) 0.7805(5) 0.0732(19) Uani 1 1 d . . . . .
H19 H 0.622302 0.727112 0.724867 0.088 Uiso 1 1 calc R . . . .
C17 C 0.5106(4) 0.6423(3) 0.8766(4) 0.0456(13) Uani 1 1 d . . . . .
C8 C 0.5232(4) 0.4393(4) 0.8268(4) 0.0557(15) Uani 1 1 d . . . . .
H8 H 0.588396 0.467876 0.829784 0.067 Uiso 1 1 calc R . . . .
C28 C 0.1783(5) 0.4526(5) 1.1124(5) 0.0661(17) Uani 1 1 d . . . . .
H28 H 0.199195 0.409737 1.159323 0.079 Uiso 1 1 calc R . . . .
C27 C 0.1217(5) 0.5284(5) 1.1237(5) 0.0672(17) Uani 1 1 d . . . . .
C4 C 0.6821(5) 0.2336(5) 0.9512(5) 0.0758(19) Uani 1 1 d . . . . .
H4 H 0.708050 0.292696 0.957894 0.091 Uiso 1 1 calc R . . . .
C18 C 0.5420(4) 0.6485(4) 0.7955(4) 0.0591(16) Uani 1 1 d . . . . .
H18 H 0.521474 0.603576 0.750578 0.071 Uiso 1 1 calc R . . . .
C11 C 0.2502(4) 0.4105(4) 0.8474(4) 0.0476(13) Uani 1 1 d . . . . .
C13 C 0.2341(5) 0.2536(4) 0.7980(5) 0.0676(17) Uani 1 1 d . . . . .
H13 H 0.192310 0.201284 0.786108 0.081 Uiso 1 1 calc R . . . .
C1 C 0.7007(10) 0.0233(7) 1.0987(7) 0.154(4) Uani 1 1 d . . . . .
H1A H 0.775940 0.029433 1.130569 0.232 Uiso 1 1 calc GR . . . .
H1B H 0.686086 -0.037784 1.077018 0.232 Uiso 1 1 calc GR . . . .
H1C H 0.658284 0.037580 1.140392 0.232 Uiso 1 1 calc GR . . . .
C12 C 0.1923(4) 0.3302(4) 0.8291(4) 0.0660(17) Uani 1 1 d . . . . .
H12 H 0.123712 0.327612 0.837966 0.079 Uiso 1 1 calc R . . . .
C25 C 0.1128(4) 0.5805(4) 0.9735(4) 0.0556(15) Uani 1 1 d . . . . .
H25 H 0.090434 0.623410 0.926762 0.067 Uiso 1 1 calc R . . . .
C3 C 0.7081(6) 0.1755(7) 1.0256(6) 0.098(3) Uani 1 1 d . . . . .
H3 H 0.750742 0.195983 1.082569 0.117 Uiso 1 1 calc R . . . .
C7 C 0.6065(7) 0.0602(6) 0.9325(6) 0.102(3) Uani 1 1 d . . . . .
H7 H 0.580152 0.001208 0.925943 0.122 Uiso 1 1 calc R . . . .
C16 C 0.4410(4) 0.5676(3) 0.8945(4) 0.0478(13) Uani 1 1 d . . . . .
C29 C 0.2030(4) 0.4420(4) 1.0300(4) 0.0577(16) Uani 1 1 d . . . . .
H29 H 0.242711 0.391677 1.021637 0.069 Uiso 1 1 calc R . . . .
C21 C 0.6080(6) 0.7797(4) 0.9294(6) 0.081(2) Uani 1 1 d . . . . .
H21 H 0.630910 0.823722 0.974950 0.097 Uiso 1 1 calc R . . . .
C14 C 0.3351(4) 0.2524(4) 0.7840(4) 0.0601(16) Uani 1 1 d . . . . .
H14 H 0.362661 0.200975 0.762940 0.072 Uiso 1 1 calc R . . . .
C20 C 0.6374(5) 0.7842(5) 0.8482(6) 0.084(2) Uani 1 1 d . . . . .
H20 H 0.681222 0.831576 0.839587 0.100 Uiso 1 1 calc R . . . .
C15 C 0.3939(4) 0.3325(4) 0.8033(4) 0.0497(14) Uani 1 1 d . . . . .
C22 C 0.5433(4) 0.7081(4) 0.9428(5) 0.0610(16) Uani 1 1 d . . . . .
H22 H 0.522177 0.704923 0.997171 0.073 Uiso 1 1 calc R . . . .
C2 C 0.6718(7) 0.0876(6) 1.0169(5) 0.093(2) Uani 1 1 d . . . . .
C5 C 0.6178(4) 0.2046(4) 0.8668(4) 0.0549(15) Uani 1 1 d . . . . .
C26 C 0.0892(5) 0.5924(4) 1.0557(5) 0.0631(17) Uani 1 1 d . . . . .
H26 H 0.051505 0.643356 1.065547 0.076 Uiso 1 1 calc R . . . .
C6 C 0.5793(6) 0.1171(5) 0.8580(5) 0.083(2) Uani 1 1 d . . . . .
H6 H 0.535012 0.096874 0.801493 0.099 Uiso 1 1 calc R . . . .


_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 O1 1.418(4) . ?
S1 O2 1.429(4) . ?
S1 N1 1.675(4) . ?
S1 C5 1.730(6) . ?
F1 C27 1.345(7) . ?
O3 C16 1.214(6) . ?
O4 C23 1.215(6) . ?
N1 C8 1.376(7) . ?
N1 C15 1.409(6) . ?
C10 C9 1.446(7) . ?
C10 C11 1.412(7) . ?
C10 C15 1.403(7) . ?
C9 C8 1.358(7) . ?
C9 C16 1.463(7) . ?
C24 C23 1.468(8) . ?
C24 C25 1.398(7) . ?
C24 C29 1.387(7) . ?
C23 C11 1.510(8) . ?
C19 H19 0.9300 . ?
C19 C18 1.399(8) . ?
C19 C20 1.353(10) . ?
C17 C18 1.386(8) . ?
C17 C16 1.493(7) . ?
C17 C22 1.370(8) . ?
C8 H8 0.9300 . ?
C28 H28 0.9300 . ?
C28 C27 1.372(9) . ?
C28 C29 1.367(8) . ?
C27 C26 1.368(9) . ?
C4 H4 0.9300 . ?
C4 C3 1.373(10) . ?
C4 C5 1.376(8) . ?
C18 H18 0.9300 . ?
C11 C12 1.388(8) . ?
C13 H13 0.9300 . ?
C13 C12 1.388(9) . ?
C13 C14 1.374(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.514(11) . ?
C12 H12 0.9300 . ?
C25 H25 0.9300 . ?
C25 C26 1.359(8) . ?
C3 H3 0.9300 . ?
C3 C2 1.374(11) . ?
C7 H7 0.9300 . ?
C7 C2 1.373(10) . ?
C7 C6 1.364(10) . ?
C29 H29 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.373(11) . ?
C21 C22 1.394(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.391(7) . ?
C20 H20 0.9300 . ?
C22 H22 0.9300 . ?
C5 C6 1.378(8) . ?
C26 H26 0.9300 . ?
C6 H6 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
O1 S1 O2 120.7(3) . . ?
O1 S1 N1 106.7(2) . . ?
O1 S1 C5 108.8(3) . . ?
O2 S1 N1 104.0(2) . . ?
O2 S1 C5 110.7(3) . . ?
N1 S1 C5 104.6(2) . . ?
C8 N1 S1 125.0(4) . . ?
C8 N1 C15 107.8(4) . . ?
C15 N1 S1 126.8(4) . . ?
C11 C10 C9 133.6(5) . . ?
C15 C10 C9 107.7(4) . . ?
C15 C10 C11 118.7(5) . . ?
C10 C9 C16 127.1(5) . . ?
C8 C9 C10 106.2(5) . . ?
C8 C9 C16 126.2(5) . . ?
C25 C24 C23 119.0(5) . . ?
C29 C24 C23 122.8(5) . . ?
C29 C24 C25 118.2(5) . . ?
O4 C23 C24 122.5(5) . . ?
O4 C23 C11 116.6(5) . . ?
C24 C23 C11 120.9(5) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C20 C19 C18 118.9(7) . . ?
C18 C17 C16 122.9(5) . . ?
C22 C17 C18 118.9(5) . . ?
C22 C17 C16 118.3(5) . . ?
N1 C8 H8 124.4 . . ?
C9 C8 N1 111.3(5) . . ?
C9 C8 H8 124.4 . . ?
C27 C28 H28 121.0 . . ?
C29 C28 H28 121.0 . . ?
C29 C28 C27 118.0(6) . . ?
F1 C27 C28 118.8(7) . . ?
F1 C27 C26 118.9(7) . . ?
C26 C27 C28 122.3(6) . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(7) . . ?
C5 C4 H4 119.9 . . ?
C19 C18 H18 119.7 . . ?
C17 C18 C19 120.7(6) . . ?
C17 C18 H18 119.7 . . ?
C10 C11 C23 122.5(5) . . ?
C12 C11 C10 117.6(5) . . ?
C12 C11 C23 119.7(5) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C14 C13 C12 122.2(6) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.7(5) . . ?
C13 C12 H12 119.1 . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.6(6) . . ?
C26 C25 H25 119.7 . . ?
C4 C3 H3 119.6 . . ?
C4 C3 C2 120.8(7) . . ?
C2 C3 H3 119.6 . . ?
C2 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C2 121.8(8) . . ?
O3 C16 C9 119.1(5) . . ?
O3 C16 C17 119.9(5) . . ?
C9 C16 C17 120.9(5) . . ?
C24 C29 H29 119.2 . . ?
C28 C29 C24 121.6(6) . . ?
C28 C29 H29 119.2 . . ?
C20 C21 H21 120.5 . . ?
C20 C21 C22 119.1(7) . . ?
C22 C21 H21 120.5 . . ?
C13 C14 H14 121.9 . . ?
C13 C14 C15 116.2(5) . . ?
C15 C14 H14 121.9 . . ?
C19 C20 C21 121.6(6) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C10 C15 N1 107.1(4) . . ?
C14 C15 N1 129.4(5) . . ?
C14 C15 C10 123.5(5) . . ?
C17 C22 C21 120.7(6) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C3 C2 C1 120.9(8) . . ?
C7 C2 C1 120.9(8) . . ?
C7 C2 C3 118.2(8) . . ?
C4 C5 S1 119.9(5) . . ?
C4 C5 C6 119.3(6) . . ?
C6 C5 S1 120.8(5) . . ?
C27 C26 H26 120.4 . . ?
C25 C26 C27 119.2(6) . . ?
C25 C26 H26 120.4 . . ?
C7 C6 C5 119.6(7) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?

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
S1 N1 C8 C9 -173.1(4) . . . . ?
S1 N1 C15 C10 172.6(4) . . . . ?
S1 N1 C15 C14 -5.4(8) . . . . ?
S1 C5 C6 C7 179.1(6) . . . . ?
F1 C27 C26 C25 -179.6(5) . . . . ?
O4 C23 C11 C10 69.0(7) . . . . ?
O4 C23 C11 C12 -105.5(6) . . . . ?
O1 S1 N1 C8 -139.8(5) . . . . ?
O1 S1 N1 C15 49.0(5) . . . . ?
O1 S1 C5 C4 174.0(5) . . . . ?
O1 S1 C5 C6 -5.9(6) . . . . ?
O2 S1 N1 C8 -11.2(5) . . . . ?
O2 S1 N1 C15 177.6(4) . . . . ?
O2 S1 C5 C4 39.2(5) . . . . ?
O2 S1 C5 C6 -140.7(5) . . . . ?
N1 S1 C5 C4 -72.2(5) . . . . ?
N1 S1 C5 C6 107.9(5) . . . . ?
C10 C9 C8 N1 0.6(6) . . . . ?
C10 C9 C16 O3 23.3(8) . . . . ?
C10 C9 C16 C17 -158.8(5) . . . . ?
C10 C11 C12 C13 -2.3(9) . . . . ?
C9 C10 C11 C23 7.0(9) . . . . ?
C9 C10 C11 C12 -178.3(6) . . . . ?
C9 C10 C15 N1 0.2(5) . . . . ?
C9 C10 C15 C14 178.4(5) . . . . ?
C24 C23 C11 C10 -114.3(6) . . . . ?
C24 C23 C11 C12 71.2(7) . . . . ?
C24 C25 C26 C27 -0.5(8) . . . . ?
C23 C24 C25 C26 -178.5(5) . . . . ?
C23 C24 C29 C28 179.4(5) . . . . ?
C23 C11 C12 C13 172.5(6) . . . . ?
C8 N1 C15 C10 0.1(6) . . . . ?
C8 N1 C15 C14 -177.9(6) . . . . ?
C8 C9 C16 O3 -147.1(6) . . . . ?
C8 C9 C16 C17 30.8(8) . . . . ?
C28 C27 C26 C25 0.6(9) . . . . ?
C27 C28 C29 C24 -1.5(9) . . . . ?
C4 C3 C2 C1 179.8(9) . . . . ?
C4 C3 C2 C7 -1.7(12) . . . . ?
C4 C5 C6 C7 -0.8(10) . . . . ?
C18 C19 C20 C21 -2.7(10) . . . . ?
C18 C17 C16 O3 -155.3(5) . . . . ?
C18 C17 C16 C9 26.8(7) . . . . ?
C18 C17 C22 C21 -0.6(8) . . . . ?
C11 C10 C9 C8 -178.9(6) . . . . ?
C11 C10 C9 C16 9.1(9) . . . . ?
C11 C10 C15 N1 178.9(4) . . . . ?
C11 C10 C15 C14 -2.9(8) . . . . ?
C13 C14 C15 N1 178.8(6) . . . . ?
C13 C14 C15 C10 1.0(8) . . . . ?
C12 C13 C14 C15 0.2(9) . . . . ?
C25 C24 C23 O4 1.5(8) . . . . ?
C25 C24 C23 C11 -175.0(5) . . . . ?
C25 C24 C29 C28 1.5(8) . . . . ?
C3 C4 C5 S1 -179.5(6) . . . . ?
C3 C4 C5 C6 0.4(10) . . . . ?
C16 C9 C8 N1 172.7(5) . . . . ?
C16 C17 C18 C19 177.7(5) . . . . ?
C16 C17 C22 C21 -179.7(5) . . . . ?
C29 C24 C23 O4 -176.4(5) . . . . ?
C29 C24 C23 C11 7.1(8) . . . . ?
C29 C24 C25 C26 -0.5(7) . . . . ?
C29 C28 C27 F1 -179.5(5) . . . . ?
C29 C28 C27 C26 0.4(9) . . . . ?
C14 C13 C12 C11 0.5(10) . . . . ?
C20 C19 C18 C17 3.0(9) . . . . ?
C20 C21 C22 C17 0.9(9) . . . . ?
C15 N1 C8 C9 -0.5(6) . . . . ?
C15 C10 C9 C8 -0.5(6) . . . . ?
C15 C10 C9 C16 -172.5(5) . . . . ?
C15 C10 C11 C23 -171.2(5) . . . . ?
C15 C10 C11 C12 3.4(7) . . . . ?
C22 C17 C18 C19 -1.3(8) . . . . ?
C22 C17 C16 O3 23.7(8) . . . . ?
C22 C17 C16 C9 -154.2(5) . . . . ?
C22 C21 C20 C19 0.8(10) . . . . ?
C2 C7 C6 C5 -0.1(12) . . . . ?
C5 S1 N1 C8 105.0(5) . . . . ?
C5 S1 N1 C15 -66.3(5) . . . . ?
C5 C4 C3 C2 0.9(11) . . . . ?
C6 C7 C2 C1 179.8(9) . . . . ?
C6 C7 C2 C3 1.3(13) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 258.6 10.6 '0.11 C6H14'
2 0.500 0.500 0.500 258.6 10.6 '0.11 C6H14'

_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_20180608a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1903234'
loop_
_audit_author_name
_audit_author_address
'Manyi Wu'
;Anhui Normal University
China
;
_audit_update_record             
;
2019-03-14 deposited with the CCDC.	2019-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 N O2'
_chemical_formula_weight         277.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   12.666(3)
_cell_length_b                   9.559(2)
_cell_length_c                   11.733(2)
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 90.00(3)
_cell_angle_gamma                90.00(3)
_cell_volume                     1420.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9622
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.983
_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      293(2)
_diffrn_radiation_wavelength     0.71076
_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            52431
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.185
_diffrn_reflns_theta_max         27.676
_diffrn_reflns_theta_full        25.243
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3285
_reflns_number_gt                3129
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    0.984

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²+0.2156P] 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_abs_structure_details 
;
 Flack x determined using 1439 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3285
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4500(2) 0.1216(2) 0.7026(3) 0.0649(7) Uani 1 1 d . . . . .
H1A H 0.458250 0.057381 0.640312 0.097 Uiso 1 1 calc R U . . .
H1B H 0.409315 0.078095 0.761873 0.097 Uiso 1 1 calc R U . . .
H1C H 0.518175 0.146809 0.731739 0.097 Uiso 1 1 calc R U . . .
C2 C 0.39390(15) 0.2505(2) 0.66171(19) 0.0410(4) Uani 1 1 d . . . . .
C3 C 0.45628(14) 0.3680(2) 0.62241(16) 0.0398(4) Uani 1 1 d . . . . .
C4 C 0.56078(16) 0.3896(2) 0.6504(2) 0.0477(4) Uani 1 1 d . . . . .
H4 H 0.603358 0.325178 0.688000 0.057 Uiso 1 1 calc R U . . .
C5 C 0.50920(16) 0.5823(2) 0.56175(19) 0.0448(4) Uani 1 1 d . . . . .
C6 C 0.42279(14) 0.49082(19) 0.56216(17) 0.0383(4) Uani 1 1 d . . . . .
C7 C 0.32990(15) 0.5321(2) 0.50473(17) 0.0415(4) Uani 1 1 d . . . . .
C8 C 0.32717(19) 0.6653(2) 0.4583(2) 0.0544(5) Uani 1 1 d . . . . .
H8 H 0.266006 0.695307 0.421888 0.065 Uiso 1 1 calc R U . . .
C9 C 0.4132(2) 0.7554(2) 0.4644(3) 0.0632(7) Uani 1 1 d . . . . .
H9 H 0.407598 0.844785 0.433737 0.076 Uiso 1 1 calc R U . . .
C10 C 0.50542(19) 0.7157(2) 0.5143(2) 0.0579(6) Uani 1 1 d . . . . .
H10 H 0.563498 0.775141 0.516611 0.070 Uiso 1 1 calc R U . . .
C11 C 0.23597(15) 0.4420(2) 0.48287(19) 0.0456(4) Uani 1 1 d . . . . .
C12 C 0.24893(15) 0.3084(2) 0.41900(18) 0.0429(4) Uani 1 1 d . . . . .
C13 C 0.34584(18) 0.2661(2) 0.3763(2) 0.0524(5) Uani 1 1 d . . . . .
H13 H 0.405641 0.320331 0.389028 0.063 Uiso 1 1 calc R U . . .
C14 C 0.3535(2) 0.1432(3) 0.3147(3) 0.0676(7) Uani 1 1 d . . . . .
H14 H 0.418739 0.113986 0.287188 0.081 Uiso 1 1 calc R U . . .
C15 C 0.2654(3) 0.0647(3) 0.2942(2) 0.0714(8) Uani 1 1 d . . . . .
H15 H 0.270673 -0.017139 0.251772 0.086 Uiso 1 1 calc R U . . .
C16 C 0.1697(3) 0.1062(3) 0.3358(3) 0.0745(8) Uani 1 1 d . . . . .
H16 H 0.110119 0.051766 0.322262 0.089 Uiso 1 1 calc R U . . .
C17 C 0.1607(2) 0.2281(3) 0.3979(2) 0.0587(6) Uani 1 1 d . . . . .
H17 H 0.095181 0.256172 0.425428 0.070 Uiso 1 1 calc R U . . .
C18 C 0.70033(18) 0.5690(3) 0.6192(3) 0.0666(7) Uani 1 1 d . . . . .
H18A H 0.735755 0.545634 0.549447 0.100 Uiso 1 1 calc R U . . .
H18B H 0.736894 0.527044 0.682192 0.100 Uiso 1 1 calc R U . . .
H18C H 0.699509 0.668813 0.628502 0.100 Uiso 1 1 calc R U . . .
N1 N 0.59245(13) 0.5169(2) 0.61546(18) 0.0495(4) Uani 1 1 d . . . . .
O1 O 0.29758(12) 0.25582(16) 0.66233(16) 0.0525(4) Uani 1 1 d . . . . .
O2 O 0.14859(12) 0.4846(2) 0.5079(2) 0.0697(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.501(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.221(2) . ?
C2 C3 1.449(3) . ?
C3 C4 1.379(3) . ?
C3 C6 1.434(3) . ?
C4 N1 1.346(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.378(3) . ?
C5 C10 1.392(3) . ?
C5 C6 1.401(3) . ?
C6 C7 1.412(3) . ?
C7 C8 1.385(3) . ?
C7 C11 1.491(3) . ?
C8 C9 1.391(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.360(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O2 1.215(2) . ?
C11 C12 1.490(3) . ?
C12 C17 1.378(3) . ?
C12 C13 1.386(3) . ?
C13 C14 1.382(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.366(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N1 1.455(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 120.95(18) . . ?
O1 C2 C1 120.3(2) . . ?
C3 C2 C1 118.72(18) . . ?
C4 C3 C6 106.20(17) . . ?
C4 C3 C2 124.29(19) . . ?
C6 C3 C2 129.06(17) . . ?
N1 C4 C3 110.41(19) . . ?
N1 C4 H4 124.8 . . ?
C3 C4 H4 124.8 . . ?
N1 C5 C10 128.6(2) . . ?
N1 C5 C6 108.23(18) . . ?
C10 C5 C6 123.1(2) . . ?
C5 C6 C7 118.34(18) . . ?
C5 C6 C3 106.35(17) . . ?
C7 C6 C3 135.26(17) . . ?
C8 C7 C6 117.7(2) . . ?
C8 C7 C11 116.30(19) . . ?
C6 C7 C11 125.84(17) . . ?
C7 C8 C9 121.9(2) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C10 C9 C8 121.5(2) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C5 117.2(2) . . ?
C9 C10 H10 121.4 . . ?
C5 C10 H10 121.4 . . ?
O2 C11 C12 120.6(2) . . ?
O2 C11 C7 119.5(2) . . ?
C12 C11 C7 119.59(16) . . ?
C17 C12 C13 119.4(2) . . ?
C17 C12 C11 118.58(19) . . ?
C13 C12 C11 121.95(19) . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 119.9(3) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 N1 C5 108.75(17) . . ?
C4 N1 C18 125.5(2) . . ?
C5 N1 C18 125.2(2) . . ?

_refine_diff_density_max         0.143
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.033

