# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_Reajean1b_0m
_database_code_depnum_ccdc_archive 'CCDC 1443506'

_audit_update_record             
;
2016-03-03 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N2 O2, 0.589(H2 O)'
_chemical_formula_sum            'C22 H21.18 N2 O2.59'
_chemical_formula_weight         354.99

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.1639(9)
_cell_length_b                   21.320(2)
_cell_length_c                   10.0007(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.6520(10)
_cell_angle_gamma                90
_cell_volume                     1840.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9480
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.64

_exptl_crystal_description       rhomb
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.618
_exptl_crystal_size_mid          0.582
_exptl_crystal_size_min          0.252
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6985
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS-2014/2 - Bruker AXS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(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            21466
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.910
_diffrn_reflns_theta_max         27.640
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4267
_reflns_number_gt                3714
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+1.0969P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4267
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1072
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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 0.69754(13) 0.24181(5) 0.07259(11) 0.0314(2) Uani 1 1 d . . . . .
C10 C 1.03445(15) 0.38681(6) 0.35982(14) 0.0216(3) Uani 1 1 d . . . . .
H10 H 1.0779 0.3513 0.4165 0.026 Uiso 1 1 calc R U . . .
O2 O 0.43611(13) 0.41497(6) -0.05281(13) 0.0441(3) Uani 1 1 d . . . . .
C7 C 0.78164(15) 0.28847(6) 0.09120(14) 0.0208(3) Uani 1 1 d . . . . .
N1 N 0.82758(12) 0.31971(5) 0.21719(11) 0.0184(2) Uani 1 1 d . . . . .
N2 N 0.69491(14) 0.43038(5) 0.04145(13) 0.0254(3) Uani 1 1 d . . . . .
C15 C 0.70312(19) 0.45262(7) -0.09521(17) 0.0333(3) Uani 1 1 d . . . . .
H15A H 0.6172 0.4347 -0.1730 0.050 Uiso 1 1 calc R U . . .
H15B H 0.8017 0.4395 -0.1046 0.050 Uiso 1 1 calc R U . . .
H15C H 0.6959 0.4985 -0.0990 0.050 Uiso 1 1 calc R U . . .
C3 C 0.94885(19) 0.33176(7) -0.24914(16) 0.0319(3) Uani 1 1 d . . . . .
H3 H 0.9855 0.3394 -0.3259 0.038 Uiso 1 1 calc R U . . .
C2 C 1.04845(18) 0.33840(7) -0.11020(16) 0.0276(3) Uani 1 1 d . . . . .
H2 H 1.1530 0.3507 -0.0920 0.033 Uiso 1 1 calc R U . . .
C1 C 0.99471(16) 0.32698(6) 0.00220(15) 0.0227(3) Uani 1 1 d . . . . .
H1 H 1.0627 0.3316 0.0972 0.027 Uiso 1 1 calc R U . . .
C6 C 0.84126(16) 0.30879(6) -0.02436(14) 0.0209(3) Uani 1 1 d . . . . .
C9 C 0.90040(14) 0.38008(6) 0.24220(14) 0.0181(3) Uani 1 1 d . . . . .
C14 C 0.83582(15) 0.43307(6) 0.16089(15) 0.0217(3) Uani 1 1 d . . . . .
C16 C 0.55423(17) 0.41738(7) 0.05270(17) 0.0293(3) Uani 1 1 d . . . . .
C17 C 0.54105(15) 0.40650(6) 0.19544(17) 0.0270(3) Uani 1 1 d . . . . .
C22 C 0.60658(16) 0.44663(7) 0.31071(17) 0.0282(3) Uani 1 1 d . . . . .
H22 H 0.6704 0.4805 0.3023 0.034 Uiso 1 1 calc R U . . .
C21 C 0.57880(17) 0.43717(7) 0.43709(18) 0.0325(3) Uani 1 1 d . . . . .
H21 H 0.6238 0.4646 0.5150 0.039 Uiso 1 1 calc R U . . .
C20 C 0.48552(17) 0.38785(8) 0.45071(19) 0.0348(4) Uani 1 1 d . . . . .
H20 H 0.4670 0.3815 0.5377 0.042 Uiso 1 1 calc R U . . .
C11 C 1.10512(16) 0.44506(7) 0.39498(16) 0.0273(3) Uani 1 1 d . . . . .
H11 H 1.1954 0.4493 0.4764 0.033 Uiso 1 1 calc R U . . .
C12 C 1.04397(17) 0.49693(7) 0.31125(18) 0.0310(3) Uani 1 1 d . . . . .
H12 H 1.0935 0.5366 0.3339 0.037 Uiso 1 1 calc R U . . .
C13 C 0.91055(17) 0.49076(6) 0.19463(17) 0.0282(3) Uani 1 1 d . . . . .
H13 H 0.8694 0.5263 0.1369 0.034 Uiso 1 1 calc R U . . .
C19 C 0.41962(17) 0.34799(7) 0.3367(2) 0.0361(4) Uani 1 1 d . . . . .
H19 H 0.3561 0.3142 0.3457 0.043 Uiso 1 1 calc R U . . .
C18 C 0.44606(16) 0.35733(7) 0.20977(19) 0.0324(3) Uani 1 1 d . . . . .
H18 H 0.3994 0.3302 0.1318 0.039 Uiso 1 1 calc R U . . .
C8 C 0.79701(16) 0.29032(7) 0.33836(14) 0.0242(3) Uani 1 1 d . . . . .
H8A H 0.7065 0.2628 0.3033 0.036 Uiso 1 1 calc R U . . .
H8B H 0.7768 0.3230 0.3988 0.036 Uiso 1 1 calc R U . . .
H8C H 0.8874 0.2656 0.3936 0.036 Uiso 1 1 calc R U . . .
C5 C 0.74205(17) 0.30217(7) -0.16450(15) 0.0268(3) Uani 1 1 d . . . . .
H5 H 0.6376 0.2896 -0.1834 0.032 Uiso 1 1 calc R U . . .
C4 C 0.79621(19) 0.31398(7) -0.27605(16) 0.0321(3) Uani 1 1 d . . . . .
H4 H 0.7283 0.3099 -0.3712 0.039 Uiso 1 1 calc R U . . .
O1S O 0.3033(3) 0.38035(10) 0.6794(2) 0.0536(9) Uani 0.589(5) 1 d . . P . .
H1S H 0.2765 0.3384 0.6687 0.064 Uiso 0.589(5) 1 d R U P . .
H2S H 0.3593 0.3881 0.7717 0.064 Uiso 0.589(5) 1 d R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2336(16) . ?
C10 C11 1.3899(19) . ?
C10 C9 1.3933(18) . ?
C10 H10 0.9500 . ?
O2 C16 1.2327(18) . ?
C7 N1 1.3607(17) . ?
C7 C6 1.4989(19) . ?
N1 C9 1.4326(16) . ?
N1 C8 1.4724(16) . ?
N2 C16 1.3598(19) . ?
N2 C14 1.4353(17) . ?
N2 C15 1.4721(19) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C3 C4 1.385(2) . ?
C3 C2 1.390(2) . ?
C3 H3 0.9500 . ?
C2 C1 1.392(2) . ?
C2 H2 0.9500 . ?
C1 C6 1.395(2) . ?
C1 H1 0.9500 . ?
C6 C5 1.3978(19) . ?
C9 C14 1.4014(18) . ?
C14 C13 1.3929(19) . ?
C16 C17 1.491(2) . ?
C17 C22 1.399(2) . ?
C17 C18 1.400(2) . ?
C22 C21 1.385(2) . ?
C22 H22 0.9500 . ?
C21 C20 1.390(2) . ?
C21 H21 0.9500 . ?
C20 C19 1.387(2) . ?
C20 H20 0.9500 . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C19 C18 1.384(2) . ?
C19 H19 0.9500 . ?
C18 H18 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C5 C4 1.388(2) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
O1S H1S 0.9234 . ?
O1S H2S 0.9076 . ?

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
C11 C10 C9 120.60(13) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
O1 C7 N1 121.16(12) . . ?
O1 C7 C6 119.21(12) . . ?
N1 C7 C6 119.53(11) . . ?
C7 N1 C9 125.62(11) . . ?
C7 N1 C8 117.94(11) . . ?
C9 N1 C8 116.42(10) . . ?
C16 N2 C14 123.50(12) . . ?
C16 N2 C15 119.23(12) . . ?
C14 N2 C15 116.56(12) . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C3 C2 120.19(14) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C2 C1 119.86(14) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C1 C6 120.16(13) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C1 C6 C5 119.54(13) . . ?
C1 C6 C7 122.61(12) . . ?
C5 C6 C7 117.46(12) . . ?
C10 C9 C14 119.15(12) . . ?
C10 C9 N1 117.81(11) . . ?
C14 C9 N1 122.82(11) . . ?
C13 C14 C9 119.60(12) . . ?
C13 C14 N2 117.92(12) . . ?
C9 C14 N2 122.47(12) . . ?
O2 C16 N2 121.45(15) . . ?
O2 C16 C17 118.85(14) . . ?
N2 C16 C17 119.70(13) . . ?
C22 C17 C18 118.88(15) . . ?
C22 C17 C16 122.92(13) . . ?
C18 C17 C16 117.90(14) . . ?
C21 C22 C17 120.22(14) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
C22 C21 C20 120.47(15) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C19 C20 C21 119.65(16) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C12 C11 C10 120.03(13) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 119.77(13) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.75(13) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C18 C19 C20 120.24(15) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C18 C17 120.54(15) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C5 C6 119.98(14) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C3 C4 C5 120.27(14) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
H1S O1S H2S 109.4 . . ?

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 C7 N1 C9 -167.92(12) . . . . ?
C6 C7 N1 C9 15.57(19) . . . . ?
O1 C7 N1 C8 10.38(19) . . . . ?
C6 C7 N1 C8 -166.13(11) . . . . ?
C4 C3 C2 C1 0.2(2) . . . . ?
C3 C2 C1 C6 0.1(2) . . . . ?
C2 C1 C6 C5 -0.03(19) . . . . ?
C2 C1 C6 C7 172.52(12) . . . . ?
O1 C7 C6 C1 -135.93(14) . . . . ?
N1 C7 C6 C1 40.65(18) . . . . ?
O1 C7 C6 C5 36.76(18) . . . . ?
N1 C7 C6 C5 -146.66(12) . . . . ?
C11 C10 C9 C14 -1.12(19) . . . . ?
C11 C10 C9 N1 -175.96(12) . . . . ?
C7 N1 C9 C10 -130.90(13) . . . . ?
C8 N1 C9 C10 50.78(15) . . . . ?
C7 N1 C9 C14 54.47(18) . . . . ?
C8 N1 C9 C14 -123.85(13) . . . . ?
C10 C9 C14 C13 3.16(19) . . . . ?
N1 C9 C14 C13 177.72(12) . . . . ?
C10 C9 C14 N2 -177.65(12) . . . . ?
N1 C9 C14 N2 -3.1(2) . . . . ?
C16 N2 C14 C13 -114.37(15) . . . . ?
C15 N2 C14 C13 55.88(17) . . . . ?
C16 N2 C14 C9 66.42(18) . . . . ?
C15 N2 C14 C9 -123.33(14) . . . . ?
C14 N2 C16 O2 -179.34(13) . . . . ?
C15 N2 C16 O2 10.7(2) . . . . ?
C14 N2 C16 C17 1.4(2) . . . . ?
C15 N2 C16 C17 -168.59(12) . . . . ?
O2 C16 C17 C22 -130.65(15) . . . . ?
N2 C16 C17 C22 48.63(19) . . . . ?
O2 C16 C17 C18 42.95(19) . . . . ?
N2 C16 C17 C18 -137.78(14) . . . . ?
C18 C17 C22 C21 0.7(2) . . . . ?
C16 C17 C22 C21 174.23(13) . . . . ?
C17 C22 C21 C20 -0.1(2) . . . . ?
C22 C21 C20 C19 -0.2(2) . . . . ?
C9 C10 C11 C12 -1.2(2) . . . . ?
C10 C11 C12 C13 1.5(2) . . . . ?
C11 C12 C13 C14 0.6(2) . . . . ?
C9 C14 C13 C12 -2.9(2) . . . . ?
N2 C14 C13 C12 177.84(13) . . . . ?
C21 C20 C19 C18 -0.2(2) . . . . ?
C20 C19 C18 C17 0.8(2) . . . . ?
C22 C17 C18 C19 -1.1(2) . . . . ?
C16 C17 C18 C19 -174.94(13) . . . . ?
C1 C6 C5 C4 -0.3(2) . . . . ?
C7 C6 C5 C4 -173.27(13) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C6 C5 C4 C3 0.6(2) . . . . ?

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.040

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_cu_Reajean2b_0m
_database_code_depnum_ccdc_archive 'CCDC 1443507'

_audit_update_record             
;
2015-12-19 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N2 O2'
_chemical_formula_sum            'C22 H20 N2 O2'
_chemical_formula_weight         344.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.24110(10)
_cell_length_b                   14.0973(2)
_cell_length_c                   16.1938(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1881.35(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7678
_cell_measurement_theta_min      4.16
_cell_measurement_theta_max      68.26

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.629
_exptl_crystal_size_mid          0.297
_exptl_crystal_size_min          0.294
_exptl_absorpt_coefficient_mu    0.626
_shelx_estimated_absorpt_T_min   0.694
_shelx_estimated_absorpt_T_max   0.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6789
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS-2014/2 - Bruker AXS'

_exptl_special_details           ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            13866
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.158
_diffrn_reflns_theta_max         68.254
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3414
_reflns_number_gt                3312
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.986

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0335P)²+0.1885P] 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     SHELXL
_refine_ls_extinction_coef       0.0040(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1377 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.03(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3414
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0718
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.20872(15) 0.46645(8) 0.73066(8) 0.0295(3) Uani 1 1 d . . . . .
O2 O -0.23106(14) 0.64010(9) 0.80516(7) 0.0285(3) Uani 1 1 d . . . . .
N1 N 0.26921(17) 0.61529(10) 0.77220(8) 0.0216(3) Uani 1 1 d . . . . .
N2 N -0.02898(16) 0.72763(10) 0.75027(8) 0.0202(3) Uani 1 1 d . . . . .
C1 C 0.0411(3) 0.63305(17) 0.47617(12) 0.0481(6) Uani 1 1 d . . . . .
H1 H 0.0020 0.6499 0.4230 0.058 Uiso 1 1 calc R U . . .
C2 C -0.0365(3) 0.56338(16) 0.52125(13) 0.0444(5) Uani 1 1 d . . . . .
H3 H -0.1281 0.5317 0.4987 0.053 Uiso 1 1 calc R U . . .
C3 C 0.0191(2) 0.53966(14) 0.59952(11) 0.0340(4) Uani 1 1 d . . . . .
H4 H -0.0343 0.4915 0.6302 0.041 Uiso 1 1 calc R U . . .
C4 C 0.1527(2) 0.58607(12) 0.63328(10) 0.0252(4) Uani 1 1 d . . . . .
C5 C 0.21171(19) 0.55223(11) 0.71588(10) 0.0221(3) Uani 1 1 d . . . . .
C6 C 0.27129(19) 0.71583(11) 0.76154(9) 0.0196(3) Uani 1 1 d . . . . .
C7 C 0.12932(19) 0.76925(12) 0.75128(9) 0.0200(3) Uani 1 1 d . . . . .
C8 C -0.09677(18) 0.67756(11) 0.81314(10) 0.0206(3) Uani 1 1 d . . . . .
C9 C -0.01012(19) 0.67009(12) 0.89420(9) 0.0225(3) Uani 1 1 d . . . . .
C10 C 0.0591(2) 0.74846(14) 0.93293(10) 0.0269(4) Uani 1 1 d . . . . .
H14 H 0.0598 0.8083 0.9059 0.032 Uiso 1 1 calc R U . . .
C11 C 0.1270(2) 0.73928(17) 1.01113(11) 0.0374(5) Uani 1 1 d . . . . .
H17 H 0.1724 0.7930 1.0379 0.045 Uiso 1 1 calc R U . . .
C12 C 0.1284(3) 0.65201(19) 1.04977(11) 0.0436(5) Uani 1 1 d . . . . .
H2 H 0.1786 0.6453 1.1023 0.052 Uiso 1 1 calc R U . . .
C13 C 0.1749(3) 0.67811(16) 0.50833(12) 0.0431(5) Uani 1 1 d . . . . .
H20 H 0.2289 0.7253 0.4768 0.052 Uiso 1 1 calc R U . . .
C14 C 0.2320(2) 0.65512(14) 0.58671(10) 0.0318(4) Uani 1 1 d . . . . .
H19 H 0.3248 0.6864 0.6084 0.038 Uiso 1 1 calc R U . . .
C15 C 0.3518(2) 0.57801(13) 0.84629(10) 0.0275(4) Uani 1 1 d . . . . .
H6 H 0.3039 0.5169 0.8616 0.041 Uiso 1 1 calc R U . . .
H5 H 0.3388 0.6230 0.8920 0.041 Uiso 1 1 calc R U . . .
H7 H 0.4675 0.5695 0.8344 0.041 Uiso 1 1 calc R U . . .
C16 C 0.42071(19) 0.76185(13) 0.76382(10) 0.0244(3) Uani 1 1 d . . . . .
H8 H 0.5166 0.7261 0.7735 0.029 Uiso 1 1 calc R U . . .
C17 C 0.4316(2) 0.85893(13) 0.75211(10) 0.0275(4) Uani 1 1 d . . . . .
H9 H 0.5342 0.8896 0.7541 0.033 Uiso 1 1 calc R U . . .
C18 C 0.2917(2) 0.91121(12) 0.73739(11) 0.0285(4) Uani 1 1 d . . . . .
H10 H 0.2988 0.9775 0.7274 0.034 Uiso 1 1 calc R U . . .
C19 C 0.1422(2) 0.86674(12) 0.73721(10) 0.0242(4) Uani 1 1 d . . . . .
H18 H 0.0469 0.9030 0.7274 0.029 Uiso 1 1 calc R U . . .
C20 C -0.13189(19) 0.74881(13) 0.67828(10) 0.0261(4) Uani 1 1 d . . . . .
H12 H -0.2059 0.6956 0.6683 0.039 Uiso 1 1 calc R U . . .
H11 H -0.0633 0.7585 0.6296 0.039 Uiso 1 1 calc R U . . .
H13 H -0.1950 0.8064 0.6890 0.039 Uiso 1 1 calc R U . . .
C21 C 0.0570(3) 0.57416(17) 1.01222(12) 0.0429(5) Uani 1 1 d . . . . .
H16 H 0.0564 0.5145 1.0395 0.051 Uiso 1 1 calc R U . . .
C22 C -0.0137(2) 0.58327(14) 0.93479(11) 0.0324(4) Uani 1 1 d . . . . .
H15 H -0.0645 0.5302 0.9096 0.039 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.233(2) . ?
O2 C8 1.233(2) . ?
N1 C5 1.359(2) . ?
N1 C6 1.428(2) . ?
N1 C15 1.476(2) . ?
N2 C8 1.359(2) . ?
N2 C7 1.431(2) . ?
N2 C20 1.4723(19) . ?
C1 C13 1.375(4) . ?
C1 C2 1.381(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(3) . ?
C2 H3 0.9500 . ?
C3 C4 1.392(3) . ?
C3 H4 0.9500 . ?
C4 C14 1.394(3) . ?
C4 C5 1.501(2) . ?
C6 C16 1.392(2) . ?
C6 C7 1.401(2) . ?
C7 C19 1.397(2) . ?
C8 C9 1.498(2) . ?
C9 C22 1.390(3) . ?
C9 C10 1.392(3) . ?
C10 C11 1.391(2) . ?
C10 H14 0.9500 . ?
C11 C12 1.380(3) . ?
C11 H17 0.9500 . ?
C12 C21 1.386(3) . ?
C12 H2 0.9500 . ?
C13 C14 1.392(3) . ?
C13 H20 0.9500 . ?
C14 H19 0.9500 . ?
C15 H6 0.9800 . ?
C15 H5 0.9800 . ?
C15 H7 0.9800 . ?
C16 C17 1.385(2) . ?
C16 H8 0.9500 . ?
C17 C18 1.389(3) . ?
C17 H9 0.9500 . ?
C18 C19 1.382(3) . ?
C18 H10 0.9500 . ?
C19 H18 0.9500 . ?
C20 H12 0.9800 . ?
C20 H11 0.9800 . ?
C20 H13 0.9800 . ?
C21 C22 1.389(3) . ?
C21 H16 0.9500 . ?
C22 H15 0.9500 . ?

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
C5 N1 C6 124.93(13) . . ?
C5 N1 C15 118.25(14) . . ?
C6 N1 C15 116.49(13) . . ?
C8 N2 C7 125.41(13) . . ?
C8 N2 C20 117.50(13) . . ?
C7 N2 C20 116.82(13) . . ?
C13 C1 C2 120.00(19) . . ?
C13 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H3 120.0 . . ?
C3 C2 H3 120.0 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H4 119.8 . . ?
C4 C3 H4 119.8 . . ?
C3 C4 C14 119.11(16) . . ?
C3 C4 C5 117.18(16) . . ?
C14 C4 C5 123.49(16) . . ?
O1 C5 N1 121.22(15) . . ?
O1 C5 C4 118.57(15) . . ?
N1 C5 C4 120.20(14) . . ?
C16 C6 C7 119.42(14) . . ?
C16 C6 N1 118.02(14) . . ?
C7 C6 N1 122.53(15) . . ?
C19 C7 C6 118.98(15) . . ?
C19 C7 N2 118.09(14) . . ?
C6 C7 N2 122.85(14) . . ?
O2 C8 N2 120.86(15) . . ?
O2 C8 C9 119.32(14) . . ?
N2 C8 C9 119.80(14) . . ?
C22 C9 C10 119.63(16) . . ?
C22 C9 C8 117.79(16) . . ?
C10 C9 C8 122.28(15) . . ?
C11 C10 C9 120.07(18) . . ?
C11 C10 H14 120.0 . . ?
C9 C10 H14 120.0 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H17 120.0 . . ?
C10 C11 H17 120.0 . . ?
C11 C12 C21 120.21(18) . . ?
C11 C12 H2 119.9 . . ?
C21 C12 H2 119.9 . . ?
C1 C13 C14 120.6(2) . . ?
C1 C13 H20 119.7 . . ?
C14 C13 H20 119.7 . . ?
C13 C14 C4 119.82(19) . . ?
C13 C14 H19 120.1 . . ?
C4 C14 H19 120.1 . . ?
N1 C15 H6 109.5 . . ?
N1 C15 H5 109.5 . . ?
H6 C15 H5 109.5 . . ?
N1 C15 H7 109.5 . . ?
H6 C15 H7 109.5 . . ?
H5 C15 H7 109.5 . . ?
C17 C16 C6 120.96(15) . . ?
C17 C16 H8 119.5 . . ?
C6 C16 H8 119.5 . . ?
C16 C17 C18 119.61(16) . . ?
C16 C17 H9 120.2 . . ?
C18 C17 H9 120.2 . . ?
C19 C18 C17 119.97(16) . . ?
C19 C18 H10 120.0 . . ?
C17 C18 H10 120.0 . . ?
C18 C19 C7 120.90(15) . . ?
C18 C19 H18 119.6 . . ?
C7 C19 H18 119.6 . . ?
N2 C20 H12 109.5 . . ?
N2 C20 H11 109.5 . . ?
H12 C20 H11 109.5 . . ?
N2 C20 H13 109.5 . . ?
H12 C20 H13 109.5 . . ?
H11 C20 H13 109.5 . . ?
C12 C21 C22 120.1(2) . . ?
C12 C21 H16 120.0 . . ?
C22 C21 H16 120.0 . . ?
C21 C22 C9 119.98(19) . . ?
C21 C22 H15 120.0 . . ?
C9 C22 H15 120.0 . . ?

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
C13 C1 C2 C3 0.9(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C14 -1.5(3) . . . . ?
C2 C3 C4 C5 -176.28(17) . . . . ?
C6 N1 C5 O1 -177.43(15) . . . . ?
C15 N1 C5 O1 9.4(2) . . . . ?
C6 N1 C5 C4 3.6(2) . . . . ?
C15 N1 C5 C4 -169.56(14) . . . . ?
C3 C4 C5 O1 37.6(2) . . . . ?
C14 C4 C5 O1 -136.95(17) . . . . ?
C3 C4 C5 N1 -143.35(16) . . . . ?
C14 C4 C5 N1 42.1(2) . . . . ?
C5 N1 C6 C16 -120.01(17) . . . . ?
C15 N1 C6 C16 53.22(19) . . . . ?
C5 N1 C6 C7 61.8(2) . . . . ?
C15 N1 C6 C7 -125.01(16) . . . . ?
C16 C6 C7 C19 4.9(2) . . . . ?
N1 C6 C7 C19 -176.93(14) . . . . ?
C16 C6 C7 N2 -178.47(14) . . . . ?
N1 C6 C7 N2 -0.3(2) . . . . ?
C8 N2 C7 C19 -122.99(17) . . . . ?
C20 N2 C7 C19 50.8(2) . . . . ?
C8 N2 C7 C6 60.3(2) . . . . ?
C20 N2 C7 C6 -125.86(16) . . . . ?
C7 N2 C8 O2 -176.27(15) . . . . ?
C20 N2 C8 O2 9.9(2) . . . . ?
C7 N2 C8 C9 5.7(2) . . . . ?
C20 N2 C8 C9 -168.13(14) . . . . ?
O2 C8 C9 C22 41.8(2) . . . . ?
N2 C8 C9 C22 -140.09(16) . . . . ?
O2 C8 C9 C10 -131.97(17) . . . . ?
N2 C8 C9 C10 46.1(2) . . . . ?
C22 C9 C10 C11 1.3(2) . . . . ?
C8 C9 C10 C11 174.93(15) . . . . ?
C9 C10 C11 C12 1.2(3) . . . . ?
C10 C11 C12 C21 -2.4(3) . . . . ?
C2 C1 C13 C14 -0.9(3) . . . . ?
C1 C13 C14 C4 -0.2(3) . . . . ?
C3 C4 C14 C13 1.4(3) . . . . ?
C5 C4 C14 C13 175.89(17) . . . . ?
C7 C6 C16 C17 -3.1(2) . . . . ?
N1 C6 C16 C17 178.57(14) . . . . ?
C6 C16 C17 C18 -0.4(3) . . . . ?
C16 C17 C18 C19 2.1(3) . . . . ?
C17 C18 C19 C7 -0.3(3) . . . . ?
C6 C7 C19 C18 -3.2(2) . . . . ?
N2 C7 C19 C18 180.00(15) . . . . ?
C11 C12 C21 C22 1.2(3) . . . . ?
C12 C21 C22 C9 1.2(3) . . . . ?
C10 C9 C22 C21 -2.5(3) . . . . ?
C8 C9 C22 C21 -176.41(16) . . . . ?

_refine_diff_density_max         0.158
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.035

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_Reajean3b_0m
_database_code_depnum_ccdc_archive 'CCDC 1443508'

_audit_update_record             
;
2015-12-19 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 N O2 S'
_chemical_formula_sum            'C10 H10 N O2 S'
_chemical_formula_weight         208.25

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      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'

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

_cell_length_a                   8.3899(7)
_cell_length_b                   8.3899(7)
_cell_length_c                   27.226(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1916.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9666
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      27.64

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.542
_exptl_crystal_size_mid          0.530
_exptl_crystal_size_min          0.376
_exptl_absorpt_coefficient_mu    0.308
_shelx_estimated_absorpt_T_min   0.851
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7184
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS-2014/2 - Bruker AXS'

_exptl_special_details           ?

_diffrn_ambient_temperature      150(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            22948
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.540
_diffrn_reflns_theta_max         27.706
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2250
_reflns_number_gt                2155
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.614
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²+0.3669P] 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 815 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.05(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2250
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0729
_refine_ls_wR_factor_gt          0.0719
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.002
_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
S1 S 0.01033(5) 0.39266(6) 0.97794(2) 0.01905(13) Uani 1 1 d . . . . .
O1 O 0.02558(16) 0.42328(17) 1.02949(5) 0.0251(3) Uani 1 1 d . . . . .
O2 O -0.10523(18) 0.28067(17) 0.96022(5) 0.0273(3) Uani 1 1 d . . . . .
N1 N 0.18387(19) 0.32674(19) 0.95878(5) 0.0189(3) Uani 1 1 d . . . . .
C1 C 0.1942(3) 0.2763(3) 0.90701(7) 0.0262(4) Uani 1 1 d . . . . .
H1A H 0.2011 0.3706 0.8859 0.039 Uiso 1 1 calc R U . . .
H1B H 0.0991 0.2146 0.8984 0.039 Uiso 1 1 calc R U . . .
H1C H 0.2894 0.2103 0.9024 0.039 Uiso 1 1 calc R U . . .
C2 C 0.3248(2) 0.3971(2) 0.97976(6) 0.0179(4) Uani 1 1 d . . . . .
C3 C 0.3913(3) 0.5345(2) 0.95991(7) 0.0236(4) Uani 1 1 d . . . . .
H3 H 0.3423 0.5837 0.9323 0.028 Uiso 1 1 calc R U . . .
C4 C 0.5286(2) 0.6008(2) 0.97995(7) 0.0265(4) Uani 1 1 d . . . . .
H4 H 0.5728 0.6950 0.9662 0.032 Uiso 1 1 calc R U . . .
C5 C -0.0240(2) 0.5758(2) 0.94776(7) 0.0194(4) Uani 1 1 d . . . . .
C6 C 0.0258(2) 0.7167(2) 0.96960(7) 0.0249(4) Uani 1 1 d . . . . .
H6 H 0.0746 0.7156 1.0011 0.030 Uiso 1 1 calc R U . . .
C7 C 0.0029(3) 0.8602(2) 0.94461(8) 0.0287(4) Uani 1 1 d . . . . .
H7 H 0.0369 0.9575 0.9590 0.034 Uiso 1 1 calc R U . . .
C8 C -0.0691(2) 0.8609(3) 0.89897(8) 0.0286(5) Uani 1 1 d . . . . .
H8 H -0.0864 0.9591 0.8825 0.034 Uiso 1 1 calc R U . . .
C9 C -0.1163(3) 0.7193(3) 0.87705(7) 0.0298(4) Uani 1 1 d . . . . .
H9 H -0.1643 0.7209 0.8454 0.036 Uiso 1 1 calc R U . . .
C10 C -0.0935(2) 0.5749(2) 0.90122(7) 0.0244(4) Uani 1 1 d . . . . .
H10 H -0.1248 0.4774 0.8863 0.029 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4327(13) . ?
S1 O2 1.4337(14) . ?
S1 N1 1.6424(16) . ?
S1 C5 1.7656(19) . ?
N1 C2 1.439(2) . ?
N1 C1 1.474(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.390(3) . ?
C2 C2 1.397(4) 7_557 ?
C3 C4 1.391(3) . ?
C3 H3 0.9500 . ?
C4 C4 1.388(4) 7_557 ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C5 C10 1.395(2) . ?
C6 C7 1.396(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.387(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?

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 120.49(9) . . ?
O1 S1 N1 107.00(8) . . ?
O2 S1 N1 105.78(9) . . ?
O1 S1 C5 108.33(9) . . ?
O2 S1 C5 107.67(9) . . ?
N1 S1 C5 106.84(8) . . ?
C2 N1 C1 116.65(15) . . ?
C2 N1 S1 117.65(12) . . ?
C1 N1 S1 116.90(13) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C2 119.51(11) . 7_557 ?
C3 C2 N1 121.03(16) . . ?
C2 C2 N1 119.46(9) 7_557 . ?
C2 C3 C4 120.77(18) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C4 C4 C3 119.72(12) 7_557 . ?
C4 C4 H4 120.1 7_557 . ?
C3 C4 H4 120.1 . . ?
C6 C5 C10 121.30(17) . . ?
C6 C5 S1 119.54(14) . . ?
C10 C5 S1 119.08(15) . . ?
C5 C6 C7 118.98(18) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 120.15(19) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.54(19) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C10 120.20(18) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 118.81(18) . . ?
C9 C10 H10 120.6 . . ?
C5 C10 H10 120.6 . . ?

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 S1 N1 C2 -37.60(15) . . . . ?
O2 S1 N1 C2 -167.23(13) . . . . ?
C5 S1 N1 C2 78.25(14) . . . . ?
O1 S1 N1 C1 175.94(14) . . . . ?
O2 S1 N1 C1 46.31(16) . . . . ?
C5 S1 N1 C1 -68.21(16) . . . . ?
C1 N1 C2 C3 59.5(2) . . . . ?
S1 N1 C2 C3 -87.03(19) . . . . ?
C1 N1 C2 C2 -119.5(2) . . . 7_557 ?
S1 N1 C2 C2 93.9(2) . . . 7_557 ?
C2 C2 C3 C4 -0.1(3) 7_557 . . . ?
N1 C2 C3 C4 -179.16(18) . . . . ?
C2 C3 C4 C4 0.3(3) . . . 7_557 ?
O1 S1 C5 C6 24.02(18) . . . . ?
O2 S1 C5 C6 155.82(15) . . . . ?
N1 S1 C5 C6 -90.94(17) . . . . ?
O1 S1 C5 C10 -159.17(15) . . . . ?
O2 S1 C5 C10 -27.37(18) . . . . ?
N1 S1 C5 C10 85.87(16) . . . . ?
C10 C5 C6 C7 1.1(3) . . . . ?
S1 C5 C6 C7 177.82(16) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C9 -1.4(3) . . . . ?
C7 C8 C9 C10 0.9(3) . . . . ?
C8 C9 C10 C5 0.5(3) . . . . ?
C6 C5 C10 C9 -1.5(3) . . . . ?
S1 C5 C10 C9 -178.27(16) . . . . ?

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.067

_shelxl_version_number           2014-3

