# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_anyang_0508
_database_code_depnum_ccdc_archive 'CCDC 1859419'
_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;
_audit_creation_date             2018-05-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H17 N O S'
_chemical_formula_sum            'C12 H17 N O S'
_chemical_formula_weight         223.33
_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'
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.7338(6)
_cell_length_b                   10.3698(8)
_cell_length_c                   13.3729(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.226(7)
_cell_angle_gamma                90.00
_cell_volume                     1211.15(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1076
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      23.2090
_cell_measurement_theta_min      3.6150
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4799
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.40
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -89.00  -64.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2711  178.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -16.00   65.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -99.0000  -30.0000 81

#__ type_ start__ end____ width___ exp.time_
  3 omega    4.00   44.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -99.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
  4 omega  -18.00    8.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -39.00   40.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000 -150.0000 79
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0118427000
_diffrn_orient_matrix_UB_12      0.0610737000
_diffrn_orient_matrix_UB_13      -0.0228050000
_diffrn_orient_matrix_UB_21      -0.0495139000
_diffrn_orient_matrix_UB_22      -0.0181471000
_diffrn_orient_matrix_UB_23      -0.0396795000
_diffrn_orient_matrix_UB_31      -0.0631230000
_diffrn_orient_matrix_UB_32      0.0253551000
_diffrn_orient_matrix_UB_33      0.0267000000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1337
_reflns_number_total             2347
_reflns_odcompleteness_completeness 97.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0609
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0751P)²+0.1276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1837
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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. Shared sites
{S1', C8}
{C8', S1}
3. Uiso/Uaniso restraints and constraints
Uanis(C8') = Uanis(S1)
Uanis(S1') = Uanis(C8)
4. Others
 Fixed Sof: H9A(0.15) H9B(0.85) H10(0.15) H10A(0.85) S1'(0.2) C8'(0.2)
 H8'(0.2) S1(0.8) C8(0.8) H8(0.8)
5.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C11(H11A,H11B)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9A), C9(H9B), C10(H10), C10(H10A), C8'(H8'), C8(H8)
5.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.3619(3) 0.0054(2) -0.10675(18) 0.0868(8) Uani 1 d . . .
N1 N 0.5052(3) 0.2151(3) -0.04653(18) 0.0530(7) Uani 1 d . . .
H1 H 0.533(3) 0.143(3) -0.012(2) 0.064 Uiso 1 d . . R
C1 C 0.3375(3) 0.2238(3) -0.05183(19) 0.0451(7) Uani 1 d C . .
C2 C 0.2795(4) 0.0985(4) -0.0989(2) 0.0606(9) Uani 1 d . . .
C3 C 0.1172(4) 0.0965(4) -0.1337(3) 0.0863(12) Uani 1 d . . .
H3A H 0.0495 0.1023 -0.0765 0.104 Uiso 1 calc . . R
H3B H 0.0964 0.0157 -0.1677 0.104 Uiso 1 calc . . R
C4 C 0.0864(5) 0.2073(6) -0.2036(3) 0.1114(17) Uani 1 d . . .
H4A H -0.0209 0.2073 -0.2225 0.134 Uiso 1 calc . . R
H4B H 0.1465 0.1963 -0.2639 0.134 Uiso 1 calc . . R
C5 C 0.1263(4) 0.3345(5) -0.1556(3) 0.0892(13) Uani 1 d . . .
H5A H 0.0593 0.3493 -0.0990 0.107 Uiso 1 calc . . R
H5B H 0.1097 0.4035 -0.2034 0.107 Uiso 1 calc . . R
C6 C 0.2916(3) 0.3373(3) -0.1202(2) 0.0646(10) Uani 1 d . . .
H6A H 0.3093 0.4173 -0.0844 0.077 Uiso 1 calc . . R
H6B H 0.3578 0.3372 -0.1783 0.077 Uiso 1 calc . . R
C7 C 0.2635(3) 0.2316(3) 0.0513(2) 0.0454(7) Uani 1 d . . .
C9 C 0.1839(4) 0.1736(5) 0.2119(3) 0.0837(12) Uani 1 d . . .
H9A H 0.1661 0.1225 0.2678 0.100 Uiso 0.15 calc A 1 R
H9B H 0.1661 0.1225 0.2678 0.100 Uiso 0.85 calc A 2 R
C10 C 0.1440(4) 0.2953(5) 0.2088(3) 0.0814(12) Uani 1 d C . .
H10 H 0.0957 0.3377 0.2613 0.098 Uiso 0.15 calc B 1 R
H10A H 0.0957 0.3377 0.2613 0.098 Uiso 0.85 calc B 2 R
C11 C 0.5841(3) 0.3187(3) 0.0046(2) 0.0644(9) Uani 1 d . . .
H11A H 0.5419 0.3297 0.0711 0.077 Uiso 1 calc . . R
H11B H 0.5699 0.3987 -0.0318 0.077 Uiso 1 calc . . R
C12 C 0.7532(3) 0.2878(4) 0.0122(3) 0.0798(11) Uani 1 d . . .
H12A H 0.7940 0.2748 -0.0536 0.120 Uiso 1 calc . . GR
H12B H 0.7671 0.2108 0.0511 0.120 Uiso 1 calc . . GR
H12C H 0.8058 0.3582 0.0439 0.120 Uiso 1 calc . . GR
S1' S 0.2561(3) 0.1237(2) 0.12456(16) 0.0724(7) Uani 0.20 d C 2 .
C8' C 0.18847(12) 0.36566(10) 0.10198(8) 0.0723(4) Uani 0.20 d C 2 .
H8' H 0.1764 0.4494 0.0783 0.087 Uiso 0.20 calc C 2 R
S1 S 0.18847(12) 0.36566(10) 0.10198(8) 0.0723(4) Uani 0.80 d C 1 .
C8 C 0.2561(3) 0.1237(2) 0.12456(16) 0.0724(7) Uani 0.80 d C 1 .
H8 H 0.2917 0.0401 0.1152 0.087 Uiso 0.80 calc C 1 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
O1 C2 1.209(4) . ?
N1 H1 0.91(3) . ?
N1 C1 1.469(3) . ?
N1 C11 1.448(4) . ?
C1 C2 1.530(4) . ?
C1 C6 1.542(4) . ?
C1 C7 1.528(3) . ?
C2 C3 1.491(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.505(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.508(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.517(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 S1' 1.488(3) . ?
C7 C8' 1.681(3) . ?
C9 H9A 0.9300 . ?
C9 H9B 0.9300 . ?
C9 C10 1.310(6) . ?
C9 S1' 1.426(4) . ?
C10 H10 0.9300 . ?
C10 H10A 0.9300 . ?
C10 C8' 1.652(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.514(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C8' H8' 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
C1 N1 H1 109.7(19) . . ?
C11 N1 H1 104(2) . . ?
C11 N1 C1 116.7(2) . . ?
N1 C1 C2 107.2(2) . . ?
N1 C1 C6 109.4(2) . . ?
N1 C1 C7 112.7(2) . . ?
C2 C1 C6 108.6(2) . . ?
C7 C1 C2 106.0(2) . . ?
C7 C1 C6 112.7(2) . . ?
O1 C2 C1 121.2(3) . . ?
O1 C2 C3 121.9(3) . . ?
C3 C2 C1 117.0(3) . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C2 C3 C4 110.5(3) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C3 C4 C5 111.3(3) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C4 C5 C6 111.5(3) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C1 C6 H6A 108.6 . . ?
C1 C6 H6B 108.6 . . ?
C5 C6 C1 114.5(3) . . ?
C5 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C1 C7 C8' 125.0(2) . . ?
S1' C7 C1 125.1(2) . . ?
S1' C7 C8' 109.79(18) . . ?
H9A C9 H9B 0.0 . . ?
C10 C9 H9A 121.9 . . ?
C10 C9 H9B 121.9 . . ?
C10 C9 S1' 116.2(3) . . ?
S1' C9 H9A 121.9 . . ?
S1' C9 H9B 121.9 . . ?
C9 C10 H10 123.5 . . ?
C9 C10 H10A 123.5 . . ?
C9 C10 C8' 112.9(3) . . ?
H10 C10 H10A 0.0 . . ?
C8' C10 H10 123.5 . . ?
C8' C10 H10A 123.5 . . ?
N1 C11 H11A 109.7 . . ?
N1 C11 H11B 109.7 . . ?
N1 C11 C12 109.7(3) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 S1' C7 106.7(3) . . ?
C7 C8' H8' 132.8 . . ?
C10 C8' C7 94.39(19) . . ?
C10 C8' H8' 132.8 . . ?

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
O1 C2 C3 C4 -126.7(4) . . . . ?
N1 C1 C2 O1 14.2(4) . . . . ?
N1 C1 C2 C3 -166.3(3) . . . . ?
N1 C1 C6 C5 163.6(3) . . . . ?
N1 C1 C7 S1' -70.4(3) . . . . ?
N1 C1 C7 C8' 105.4(3) . . . . ?
C1 N1 C11 C12 174.3(3) . . . . ?
C1 C2 C3 C4 53.7(4) . . . . ?
C1 C7 S1' C9 177.5(3) . . . . ?
C1 C7 C8' C10 -177.6(2) . . . . ?
C2 C1 C6 C5 46.8(3) . . . . ?
C2 C1 C7 S1' 46.6(3) . . . . ?
C2 C1 C7 C8' -137.7(2) . . . . ?
C2 C3 C4 C5 -55.8(4) . . . . ?
C3 C4 C5 C6 56.4(4) . . . . ?
C4 C5 C6 C1 -53.1(4) . . . . ?
C6 C1 C2 O1 132.3(3) . . . . ?
C6 C1 C2 C3 -48.1(3) . . . . ?
C6 C1 C7 S1' 165.2(2) . . . . ?
C6 C1 C7 C8' -19.0(3) . . . . ?
C7 C1 C2 O1 -106.4(3) . . . . ?
C7 C1 C2 C3 73.2(3) . . . . ?
C7 C1 C6 C5 -70.3(4) . . . . ?
C9 C10 C8' C7 1.0(3) . . . . ?
C10 C9 S1' C7 -0.6(4) . . . . ?
C11 N1 C1 C2 -174.2(2) . . . . ?
C11 N1 C1 C6 68.1(3) . . . . ?
C11 N1 C1 C7 -58.0(3) . . . . ?
S1' C7 C8' C10 -1.3(2) . . . . ?
S1' C9 C10 C8' -0.3(5) . . . . ?
C8' C7 S1' C9 1.2(3) . . . . ?

_olex2_date_sample_data_collection 2018-05-08
_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_zhangfm_0912
_database_code_depnum_ccdc_archive 'CCDC 1859431'
_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;
_audit_creation_date             2017-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H12 N2 O5'
_chemical_formula_sum            'C12 H12 N2 O5'
_chemical_formula_weight         264.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   7.6972(3)
_cell_length_b                   12.8370(4)
_cell_length_c                   25.2660(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2496.50(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1522
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.7840
_cell_measurement_theta_min      4.1630
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            5960
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.48
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000   90.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00   28.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000  -60.0000 48

#__ type_ start__ end____ width___ exp.time_
  3 omega   -1.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000    0.0000 73
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0566313000
_diffrn_orient_matrix_UB_12      -0.0137644000
_diffrn_orient_matrix_UB_13      -0.0210100000
_diffrn_orient_matrix_UB_21      -0.0702535000
_diffrn_orient_matrix_UB_22      0.0033032000
_diffrn_orient_matrix_UB_23      -0.0180942000
_diffrn_orient_matrix_UB_31      0.0188550000
_diffrn_orient_matrix_UB_32      0.0534169000
_diffrn_orient_matrix_UB_33      -0.0043028000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1602
_reflns_number_total             2458
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2458
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0539P)²+0.9818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1546
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O -0.0356(3) 0.13106(15) 0.49888(8) 0.0736(6) Uani 1 d . . .
O2 O 0.0131(3) 0.33968(16) 0.42936(11) 0.0974(8) Uani 1 d . . .
O3 O 0.2020(3) 0.2243(2) 0.41768(13) 0.1268(12) Uani 1 d . . .
O4 O 0.2528(4) -0.1812(2) 0.26090(11) 0.1153(10) Uani 1 d . . .
O5 O 0.1427(4) -0.0833(2) 0.20170(10) 0.1165(11) Uani 1 d . . .
N1 N 0.0547(3) 0.25235(17) 0.41886(9) 0.0640(7) Uani 1 d . . .
N2 N 0.1748(4) -0.1050(2) 0.24743(12) 0.0765(8) Uani 1 d . . .
C1 C -0.0876(3) 0.17134(16) 0.40755(9) 0.0403(5) Uani 1 d . . .
C2 C -0.1239(3) 0.11478(18) 0.46024(10) 0.0480(6) Uani 1 d . . .
C3 C -0.2760(3) 0.0437(2) 0.45830(12) 0.0639(8) Uani 1 d . . .
H3A H -0.2989 0.0173 0.4936 0.077 Uiso 1 calc . . R
H3B H -0.2485 -0.0153 0.4358 0.077 Uiso 1 calc . . R
C4 C -0.4388(4) 0.0969(2) 0.43734(11) 0.0646(8) Uani 1 d . . .
H4A H -0.5295 0.0455 0.4322 0.077 Uiso 1 calc . . R
H4B H -0.4797 0.1473 0.4631 0.077 Uiso 1 calc . . R
C5 C -0.4023(3) 0.1513(2) 0.38563(11) 0.0608(7) Uani 1 d . . .
H5A H -0.5059 0.1875 0.3739 0.073 Uiso 1 calc . . R
H5B H -0.3720 0.1001 0.3589 0.073 Uiso 1 calc . . R
C6 C -0.2549(3) 0.22834(18) 0.39181(10) 0.0544(7) Uani 1 d . . .
H6A H -0.2845 0.2791 0.4188 0.065 Uiso 1 calc . . R
H6B H -0.2370 0.2651 0.3587 0.065 Uiso 1 calc . . R
C7 C -0.0156(3) 0.09813(16) 0.36553(9) 0.0392(5) Uani 1 d . . .
C8 C 0.0673(3) 0.00670(18) 0.37953(10) 0.0524(6) Uani 1 d . . .
H8 H 0.0802 -0.0103 0.4151 0.063 Uiso 1 calc . . R
C9 C 0.1315(3) -0.05988(19) 0.34098(12) 0.0602(7) Uani 1 d . . .
H9 H 0.1866 -0.1217 0.3503 0.072 Uiso 1 calc . . R
C10 C 0.1118(3) -0.0327(2) 0.28919(11) 0.0539(7) Uani 1 d . . .
C11 C 0.0331(4) 0.0575(2) 0.27407(10) 0.0630(8) Uani 1 d . . .
H11 H 0.0225 0.0745 0.2384 0.076 Uiso 1 calc . . R
C12 C -0.0303(4) 0.12323(19) 0.31252(10) 0.0552(7) Uani 1 d . . .
H12 H -0.0837 0.1853 0.3027 0.066 Uiso 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
O1 C2 1.208(3) . ?
O2 N1 1.196(3) . ?
O3 N1 1.190(3) . ?
O4 N2 1.198(3) . ?
O5 N2 1.214(3) . ?
N1 C1 1.537(3) . ?
N2 C10 1.486(3) . ?
C1 C2 1.542(3) . ?
C1 C6 1.534(3) . ?
C1 C7 1.522(3) . ?
C2 C3 1.486(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.522(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.507(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.513(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.382(3) . ?
C7 C12 1.382(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.387(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.363(4) . ?
C10 C11 1.362(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(3) . ?
C12 H12 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
O2 N1 C1 119.0(2) . . ?
O3 N1 O2 123.0(3) . . ?
O3 N1 C1 118.0(2) . . ?
O4 N2 O5 124.0(3) . . ?
O4 N2 C10 118.2(3) . . ?
O5 N2 C10 117.8(3) . . ?
N1 C1 C2 106.69(19) . . ?
C6 C1 N1 108.89(18) . . ?
C6 C1 C2 107.24(18) . . ?
C7 C1 N1 106.74(18) . . ?
C7 C1 C2 112.18(17) . . ?
C7 C1 C6 114.8(2) . . ?
O1 C2 C1 121.0(2) . . ?
O1 C2 C3 125.2(2) . . ?
C3 C2 C1 113.8(2) . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C2 C3 C4 112.6(2) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 C3 110.9(2) . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 C6 110.6(2) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C1 C6 H6A 109.6 . . ?
C1 C6 H6B 109.6 . . ?
C5 C6 C1 110.14(18) . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C1 120.9(2) . . ?
C8 C7 C12 118.9(2) . . ?
C12 C7 C1 120.1(2) . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.5(2) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.7 . . ?
C10 C9 C8 118.5(2) . . ?
C10 C9 H9 120.7 . . ?
C9 C10 N2 119.1(3) . . ?
C11 C10 N2 118.5(3) . . ?
C11 C10 C9 122.4(2) . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.8(2) . . ?
C12 C11 H11 120.6 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.8(2) . . ?
C11 C12 H12 119.6 . . ?

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
O1 C2 C3 C4 126.1(3) . . . . ?
O2 N1 C1 C2 -94.2(3) . . . . ?
O2 N1 C1 C6 21.2(3) . . . . ?
O2 N1 C1 C7 145.6(3) . . . . ?
O3 N1 C1 C2 84.4(3) . . . . ?
O3 N1 C1 C6 -160.2(3) . . . . ?
O3 N1 C1 C7 -35.7(3) . . . . ?
O4 N2 C10 C9 -5.6(4) . . . . ?
O4 N2 C10 C11 175.7(3) . . . . ?
O5 N2 C10 C9 173.8(3) . . . . ?
O5 N2 C10 C11 -4.8(4) . . . . ?
N1 C1 C2 O1 -6.5(3) . . . . ?
N1 C1 C2 C3 171.88(19) . . . . ?
N1 C1 C6 C5 -174.5(2) . . . . ?
N1 C1 C7 C8 93.5(2) . . . . ?
N1 C1 C7 C12 -85.6(3) . . . . ?
N2 C10 C11 C12 178.0(2) . . . . ?
C1 C2 C3 C4 -52.2(3) . . . . ?
C1 C7 C8 C9 179.6(2) . . . . ?
C1 C7 C12 C11 -179.6(2) . . . . ?
C2 C1 C6 C5 -59.4(2) . . . . ?
C2 C1 C7 C8 -23.0(3) . . . . ?
C2 C1 C7 C12 157.9(2) . . . . ?
C2 C3 C4 C5 51.3(3) . . . . ?
C3 C4 C5 C6 -56.4(3) . . . . ?
C4 C5 C6 C1 62.2(3) . . . . ?
C6 C1 C2 O1 -123.1(2) . . . . ?
C6 C1 C2 C3 55.3(2) . . . . ?
C6 C1 C7 C8 -145.7(2) . . . . ?
C6 C1 C7 C12 35.2(3) . . . . ?
C7 C1 C2 O1 110.0(2) . . . . ?
C7 C1 C2 C3 -71.6(3) . . . . ?
C7 C1 C6 C5 66.0(3) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C8 C7 C12 C11 1.3(4) . . . . ?
C8 C9 C10 N2 -178.0(2) . . . . ?
C8 C9 C10 C11 0.6(4) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C10 C11 C12 C7 -0.3(4) . . . . ?
C12 C7 C8 C9 -1.3(4) . . . . ?

_olex2_date_sample_data_collection 2017-09-14
_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_zhangfm_0111
_database_code_depnum_ccdc_archive 'CCDC 1859421'
_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;
_audit_creation_date             2017-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H13 N O3'
_chemical_formula_sum            'C12 H13 N O3'
_chemical_formula_weight         219.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   11.0589(9)
_cell_length_b                   12.7626(13)
_cell_length_c                   15.3400(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2165.1(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    886
_cell_measurement_temperature    291.01(10)
_cell_measurement_theta_max      25.8340
_cell_measurement_theta_min      3.9060
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5158
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.46
_diffrn_ambient_temperature      291.01(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9957
_diffrn_measured_fraction_theta_max 0.8965
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   14.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   14.00   76.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000  150.0000 62

#__ type_ start__ end____ width___ exp.time_
  3 omega  -18.00    8.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -45.00   -1.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000  150.0000 44
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0632657000
_diffrn_orient_matrix_UB_12      0.0040192000
_diffrn_orient_matrix_UB_13      -0.0067401000
_diffrn_orient_matrix_UB_21      0.0011272000
_diffrn_orient_matrix_UB_22      0.0521300000
_diffrn_orient_matrix_UB_23      0.0159846000
_diffrn_orient_matrix_UB_31      0.0104046000
_diffrn_orient_matrix_UB_32      0.0187944000
_diffrn_orient_matrix_UB_33      -0.0428859000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1292
_reflns_number_total             2128
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0582
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0484P)²+0.2483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1468
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 1.11886(14) -0.00310(16) 0.09338(11) 0.0612(6) Uani 1 d . . .
O2 O 0.85150(15) 0.14768(19) 0.27900(11) 0.0698(7) Uani 1 d . . .
O3 O 1.02712(16) 0.0775(2) 0.29107(11) 0.0695(7) Uani 1 d . . .
N1 N 0.93852(17) 0.10186(18) 0.24880(12) 0.0463(6) Uani 1 d . . .
C1 C 1.02892(19) -0.0150(2) 0.13737(14) 0.0432(6) Uani 1 d . . .
C2 C 0.9936(2) -0.1181(2) 0.17534(18) 0.0572(8) Uani 1 d . . .
H2A H 0.9973 -0.1142 0.2384 0.069 Uiso 1 calc . . R
H2B H 1.0502 -0.1715 0.1563 0.069 Uiso 1 calc . . R
C3 C 0.8659(2) -0.1487(2) 0.14736(18) 0.0615(8) Uani 1 d . . .
H3A H 0.8646 -0.1615 0.0850 0.074 Uiso 1 calc . . R
H3B H 0.8424 -0.2129 0.1766 0.074 Uiso 1 calc . . R
C4 C 0.7771(2) -0.0626(2) 0.16961(16) 0.0541(7) Uani 1 d . . .
H4A H 0.7754 -0.0524 0.2323 0.065 Uiso 1 calc . . R
H4B H 0.6966 -0.0831 0.1510 0.065 Uiso 1 calc . . R
C5 C 0.81194(18) 0.0392(2) 0.12543(14) 0.0427(6) Uani 1 d . . .
H5A H 0.7537 0.0928 0.1411 0.051 Uiso 1 calc . . R
H5B H 0.8081 0.0297 0.0628 0.051 Uiso 1 calc . . R
C6 C 0.93898(17) 0.0771(2) 0.15015(13) 0.0374(6) Uani 1 d . . .
C7 C 0.97945(18) 0.1783(2) 0.10691(14) 0.0386(6) Uani 1 d . . .
C8 C 0.9081(2) 0.2288(2) 0.04587(15) 0.0502(7) Uani 1 d . . .
H8 H 0.8336 0.2004 0.0305 0.060 Uiso 1 calc . . R
C9 C 0.9464(3) 0.3210(3) 0.00752(18) 0.0639(8) Uani 1 d . . .
H9 H 0.8976 0.3543 -0.0334 0.077 Uiso 1 calc . . R
C10 C 1.0566(3) 0.3639(3) 0.0296(2) 0.0670(9) Uani 1 d . . .
H10 H 1.0826 0.4256 0.0034 0.080 Uiso 1 calc . . R
C11 C 1.1281(2) 0.3146(3) 0.09086(19) 0.0620(8) Uani 1 d . . .
H11 H 1.2017 0.3440 0.1069 0.074 Uiso 1 calc . . R
C12 C 1.0911(2) 0.2220(2) 0.12846(15) 0.0506(7) Uani 1 d . . .
H12 H 1.1409 0.1884 0.1685 0.061 Uiso 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
O1 C1 1.211(3) . ?
O2 N1 1.218(2) . ?
O3 N1 1.216(2) . ?
N1 C6 1.546(3) . ?
C1 C2 1.491(4) . ?
C1 C6 1.552(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.527(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.513(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.516(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.534(3) . ?
C6 C7 1.519(4) . ?
C7 C8 1.384(3) . ?
C7 C12 1.395(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.383(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(4) . ?
C12 H12 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
O2 N1 C6 118.24(18) . . ?
O3 N1 O2 123.8(2) . . ?
O3 N1 C6 117.86(18) . . ?
O1 C1 C2 122.9(2) . . ?
O1 C1 C6 120.1(2) . . ?
C2 C1 C6 116.83(19) . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C1 C2 C3 111.0(2) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 C2 110.6(2) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 C5 110.9(2) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C4 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C4 C5 C6 113.16(19) . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
N1 C6 C1 106.28(17) . . ?
C5 C6 N1 107.66(16) . . ?
C5 C6 C1 108.5(2) . . ?
C7 C6 N1 104.78(19) . . ?
C7 C6 C1 113.56(17) . . ?
C7 C6 C5 115.48(19) . . ?
C8 C7 C6 121.6(2) . . ?
C8 C7 C12 118.6(2) . . ?
C12 C7 C6 119.8(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.5(3) . . ?
C11 C12 H12 119.8 . . ?

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
O1 C1 C2 C3 -124.2(3) . . . . ?
O1 C1 C6 N1 -117.4(2) . . . . ?
O1 C1 C6 C5 127.1(2) . . . . ?
O1 C1 C6 C7 -2.7(3) . . . . ?
O2 N1 C6 C1 -158.3(2) . . . . ?
O2 N1 C6 C5 -42.2(3) . . . . ?
O2 N1 C6 C7 81.2(2) . . . . ?
O3 N1 C6 C1 24.2(3) . . . . ?
O3 N1 C6 C5 140.3(2) . . . . ?
O3 N1 C6 C7 -96.3(3) . . . . ?
N1 C6 C7 C8 -121.6(2) . . . . ?
N1 C6 C7 C12 58.5(2) . . . . ?
C1 C2 C3 C4 -54.4(3) . . . . ?
C1 C6 C7 C8 122.9(2) . . . . ?
C1 C6 C7 C12 -57.0(3) . . . . ?
C2 C1 C6 N1 67.4(2) . . . . ?
C2 C1 C6 C5 -48.1(3) . . . . ?
C2 C1 C6 C7 -177.96(19) . . . . ?
C2 C3 C4 C5 58.7(3) . . . . ?
C3 C4 C5 C6 -58.4(3) . . . . ?
C4 C5 C6 N1 -64.1(3) . . . . ?
C4 C5 C6 C1 50.5(2) . . . . ?
C4 C5 C6 C7 179.28(19) . . . . ?
C5 C6 C7 C8 -3.3(3) . . . . ?
C5 C6 C7 C12 176.8(2) . . . . ?
C6 C1 C2 C3 50.9(3) . . . . ?
C6 C7 C8 C9 179.7(2) . . . . ?
C6 C7 C12 C11 -178.9(2) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C7 C12 C11 1.2(4) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C9 C10 C11 C12 1.4(4) . . . . ?
C10 C11 C12 C7 -1.7(4) . . . . ?
C12 C7 C8 C9 -0.4(4) . . . . ?

_olex2_date_sample_data_collection 2017-01-11
_olex2_submission_special_instructions 'No special instructions were received'
