# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_argp1
_database_code_depnum_ccdc_archive 'CCDC 1008371'
_audit_update_record             
;
2014-06-14 deposited with the CCDC.
2017-11-17 downloaded from the CCDC.
;

_audit_creation_date             2013-07-09T16:09:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
6,7-dihydro-4-nitro-6-[(1-phenyl-2-methyl)propyl]-dibenzo[d,f][1,2]thiazepine 5,5-dioxide
;
_chemical_formula_moiety         'C23 H22 N2 O4 S1'
_chemical_formula_sum            'C23 H22 N2 O4 S'
_chemical_formula_weight         422.49
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.3715(5)
_cell_length_b                   14.9202(5)
_cell_length_c                   19.0907(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4093.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2718
_cell_measurement_theta_min      3.256
_cell_measurement_theta_max      24.978
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.191
_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_absorpt_correction_T_min  0.93687
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 16.1428
_diffrn_orient_matrix_ub_11      -0.0199293
_diffrn_orient_matrix_ub_12      0.0082212
_diffrn_orient_matrix_ub_13      -0.0333621
_diffrn_orient_matrix_ub_21      0.0408005
_diffrn_orient_matrix_ub_22      -0.0167201
_diffrn_orient_matrix_ub_23      -0.0163209
_diffrn_orient_matrix_ub_31      -0.0193462
_diffrn_orient_matrix_ub_32      -0.0437529
_diffrn_orient_matrix_ub_33      0.0000059
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_number            12256
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_reflns_number_total             4570
_reflns_number_gt                2981
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_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_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_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0322P)²+1.6265P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4570
_refine_ls_number_parameters     359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1252
_refine_ls_wR_factor_gt          0.099
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.064

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9732(2) 0.34821(17) 0.57713(14) 0.0268(6) Uani 1 1 d . . .
C2 C 1.03065(18) 0.43250(15) 0.58433(12) 0.0211(5) Uani 1 1 d . . .
C3 C 1.10642(19) 0.44657(17) 0.54110(13) 0.0248(6) Uani 1 1 d . . .
C4 C 1.1553(2) 0.52672(18) 0.54351(15) 0.0303(7) Uani 1 1 d . . .
C5 C 1.1280(2) 0.59350(18) 0.58847(14) 0.0304(7) Uani 1 1 d . . .
C6 C 1.0516(2) 0.58056(17) 0.63172(13) 0.0279(6) Uani 1 1 d . . .
C7 C 1.00266(18) 0.50035(16) 0.63056(12) 0.0223(6) Uani 1 1 d . . .
C8 C 0.92390(18) 0.48807(15) 0.68022(12) 0.0224(6) Uani 1 1 d . . .
C9 C 0.8558(2) 0.55411(18) 0.68555(15) 0.0311(7) Uani 1 1 d . . .
C10 C 0.7845(2) 0.54816(19) 0.73379(15) 0.0346(7) Uani 1 1 d . . .
C11 C 0.7813(2) 0.47738(18) 0.78057(15) 0.0314(7) Uani 1 1 d . . .
C12 C 0.84932(18) 0.41307(16) 0.77643(12) 0.0244(6) Uani 1 1 d . . .
C13 C 0.91936(18) 0.41448(15) 0.72660(12) 0.0220(5) Uani 1 1 d . . .
C14 C 0.91271(19) 0.20467(16) 0.63066(14) 0.0238(6) Uani 1 1 d . . .
C15 C 0.81837(18) 0.23254(15) 0.60241(13) 0.0223(6) Uani 1 1 d . . .
C16 C 0.7531(2) 0.26783(16) 0.64839(13) 0.0259(6) Uani 1 1 d . . .
C17 C 0.6687(2) 0.29990(18) 0.62398(15) 0.0318(7) Uani 1 1 d . . .
C18 C 0.6481(2) 0.29684(18) 0.55352(16) 0.0338(7) Uani 1 1 d . . .
C19 C 0.7119(2) 0.26088(18) 0.50727(15) 0.0316(7) Uani 1 1 d . . .
C20 C 0.7964(2) 0.22881(16) 0.53152(14) 0.0264(6) Uani 1 1 d . . .
C21 C 0.9632(2) 0.13051(17) 0.58992(16) 0.0333(7) Uani 1 1 d . . .
C22 C 1.0565(2) 0.1088(2) 0.6224(2) 0.0439(8) Uani 1 1 d . . .
C23 C 0.9036(3) 0.0458(2) 0.5877(2) 0.0503(10) Uani 1 1 d . . .
N1 N 0.97526(14) 0.28547(12) 0.63754(10) 0.0216(5) Uani 1 1 d . . .
N2 N 0.84793(17) 0.34549(15) 0.83349(12) 0.0327(6) Uani 1 1 d . . .
O1 O 0.97744(12) 0.25610(11) 0.76443(9) 0.0293(4) Uani 1 1 d . . .
O2 O 1.09053(12) 0.36176(11) 0.71437(9) 0.0298(4) Uani 1 1 d . . .
O3 O 0.79011(15) 0.28563(13) 0.83058(11) 0.0439(5) Uani 1 1 d . . .
O4 O 0.90304(17) 0.35678(14) 0.88149(10) 0.0510(6) Uani 1 1 d . . .
S1 S 0.99916(5) 0.32464(4) 0.71473(3) 0.02251(17) Uani 1 1 d . . .
H1A H 0.9953(18) 0.3145(17) 0.5344(15) 0.035(8) Uiso 1 1 d . . .
H1B H 0.9088(19) 0.3648(15) 0.5689(13) 0.027(7) Uiso 1 1 d . . .
H3 H 1.1195(16) 0.3989(14) 0.5069(13) 0.021(6) Uiso 1 1 d . . .
H4 H 1.207(2) 0.5347(16) 0.5135(14) 0.038(8) Uiso 1 1 d . . .
H5 H 1.1607(17) 0.6496(16) 0.5915(13) 0.026(7) Uiso 1 1 d . . .
H6 H 1.0352(19) 0.6284(18) 0.6638(15) 0.039(8) Uiso 1 1 d . . .
H9 H 0.8583(19) 0.6049(17) 0.6531(15) 0.038(8) Uiso 1 1 d . . .
H10 H 0.7377(18) 0.5932(16) 0.7355(13) 0.032(8) Uiso 1 1 d . . .
H11 H 0.7331(19) 0.4731(16) 0.8139(14) 0.031(7) Uiso 1 1 d . . .
H15 H 0.9058(17) 0.1832(15) 0.6803(13) 0.025(7) Uiso 1 1 d . . .
H16 H 0.7702(19) 0.2696(16) 0.6998(15) 0.038(8) Uiso 1 1 d . . .
H17 H 0.6297(18) 0.3248(16) 0.6544(14) 0.029(8) Uiso 1 1 d . . .
H18 H 0.589(2) 0.3182(16) 0.5362(14) 0.036(8) Uiso 1 1 d . . .
H19 H 0.695(2) 0.2562(17) 0.4585(16) 0.047(9) Uiso 1 1 d . . .
H20 H 0.8405(19) 0.2047(16) 0.4958(15) 0.039(8) Uiso 1 1 d . . .
H21 H 0.9750(18) 0.1506(16) 0.5409(15) 0.030(7) Uiso 1 1 d . . .
H22A H 1.097(2) 0.160(2) 0.6283(16) 0.050(10) Uiso 1 1 d . . .
H22B H 1.047(2) 0.0890(19) 0.6718(17) 0.052(9) Uiso 1 1 d . . .
H22C H 1.092(2) 0.060(2) 0.5949(16) 0.056(9) Uiso 1 1 d . . .
H23A H 0.846(2) 0.054(2) 0.5704(17) 0.049(11) Uiso 1 1 d . . .
H23B H 0.889(2) 0.0237(19) 0.6354(18) 0.052(10) Uiso 1 1 d . . .
H23C H 0.935(2) -0.002(2) 0.5593(16) 0.055(9) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 1.486(3) . ?
C1 C2 1.511(3) . ?
C1 H1A 1.01(3) . ?
C1 H1B 0.97(3) . ?
C2 C3 1.382(3) . ?
C2 C7 1.402(3) . ?
C3 C4 1.388(4) . ?
C3 H3 0.98(2) . ?
C4 C5 1.372(4) . ?
C4 H4 0.94(3) . ?
C5 C6 1.388(4) . ?
C5 H5 0.96(2) . ?
C6 C7 1.388(3) . ?
C6 H6 0.97(3) . ?
C7 C8 1.488(3) . ?
C8 C9 1.393(4) . ?
C8 C13 1.412(3) . ?
C9 C10 1.380(4) . ?
C9 H9 0.98(3) . ?
C10 C11 1.384(4) . ?
C10 H10 0.95(3) . ?
C11 C12 1.372(4) . ?
C11 H11 0.94(3) . ?
C12 C13 1.385(3) . ?
C12 N2 1.484(3) . ?
C13 S1 1.779(3) . ?
C14 N1 1.509(3) . ?
C14 C15 1.517(4) . ?
C14 C21 1.535(4) . ?
C14 H15 1.01(2) . ?
C15 C16 1.388(3) . ?
C15 C20 1.391(3) . ?
C16 C17 1.385(4) . ?
C16 H16 1.01(3) . ?
C17 C18 1.378(4) . ?
C17 H17 0.89(3) . ?
C18 C19 1.381(4) . ?
C18 H18 0.96(3) . ?
C19 C20 1.386(4) . ?
C19 H19 0.96(3) . ?
C20 H20 1.00(3) . ?
C21 C22 1.512(4) . ?
C21 C23 1.527(4) . ?
C21 H21 1.00(3) . ?
C22 H22A 0.97(3) . ?
C22 H22B 1.00(3) . ?
C22 H22C 1.03(3) . ?
C23 H23A 0.90(3) . ?
C23 H23B 0.99(3) . ?
C23 H23C 1.00(3) . ?
N1 S1 1.622(2) . ?
N2 O3 1.221(3) . ?
N2 O4 1.223(3) . ?
O1 S1 1.4296(17) . ?
O2 S1 1.4251(18) . ?

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
N1 C1 C2 116.3(2) . . ?
N1 C1 H1A 107.9(15) . . ?
C2 C1 H1A 108.4(15) . . ?
N1 C1 H1B 107.8(15) . . ?
C2 C1 H1B 108.9(14) . . ?
H1A C1 H1B 107(2) . . ?
C3 C2 C7 119.5(2) . . ?
C3 C2 C1 120.2(2) . . ?
C7 C2 C1 120.1(2) . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 115.9(14) . . ?
C4 C3 H3 123.2(14) . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.8(16) . . ?
C3 C4 H4 119.1(16) . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 122.0(15) . . ?
C6 C5 H5 118.2(15) . . ?
C5 C6 C7 120.8(2) . . ?
C5 C6 H6 117.7(17) . . ?
C7 C6 H6 121.5(17) . . ?
C6 C7 C2 119.2(2) . . ?
C6 C7 C8 118.8(2) . . ?
C2 C7 C8 122.0(2) . . ?
C9 C8 C13 118.1(2) . . ?
C9 C8 C7 119.6(2) . . ?
C13 C8 C7 122.0(2) . . ?
C10 C9 C8 121.7(3) . . ?
C10 C9 H9 120.0(16) . . ?
C8 C9 H9 118.4(16) . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 120.1(16) . . ?
C11 C10 H10 119.6(16) . . ?
C12 C11 C10 118.2(3) . . ?
C12 C11 H11 121.0(15) . . ?
C10 C11 H11 120.7(15) . . ?
C11 C12 C13 123.1(2) . . ?
C11 C12 N2 115.0(2) . . ?
C13 C12 N2 121.6(2) . . ?
C12 C13 C8 118.4(2) . . ?
C12 C13 S1 123.00(19) . . ?
C8 C13 S1 118.44(19) . . ?
N1 C14 C15 110.13(19) . . ?
N1 C14 C21 109.8(2) . . ?
C15 C14 C21 116.1(2) . . ?
N1 C14 H15 103.3(14) . . ?
C15 C14 H15 109.5(15) . . ?
C21 C14 H15 107.2(13) . . ?
C16 C15 C20 118.5(3) . . ?
C16 C15 C14 118.9(2) . . ?
C20 C15 C14 122.5(2) . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16 122.0(15) . . ?
C15 C16 H16 117.3(16) . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 121.1(17) . . ?
C16 C17 H17 118.5(17) . . ?
C17 C18 C19 119.7(3) . . ?
C17 C18 H18 120.9(17) . . ?
C19 C18 H18 119.4(17) . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 H19 118.9(18) . . ?
C20 C19 H19 120.9(18) . . ?
C19 C20 C15 120.7(3) . . ?
C19 C20 H20 117.0(16) . . ?
C15 C20 H20 122.3(16) . . ?
C22 C21 C23 109.3(3) . . ?
C22 C21 C14 111.5(3) . . ?
C23 C21 C14 110.2(3) . . ?
C22 C21 H21 107.4(15) . . ?
C23 C21 H21 108.5(15) . . ?
C14 C21 H21 109.9(14) . . ?
C21 C22 H22A 114.5(18) . . ?
C21 C22 H22B 108.9(19) . . ?
H22A C22 H22B 102(3) . . ?
C21 C22 H22C 112.2(18) . . ?
H22A C22 H22C 109(3) . . ?
H22B C22 H22C 110(2) . . ?
C21 C23 H23A 114(2) . . ?
C21 C23 H23B 111.8(18) . . ?
H23A C23 H23B 101(3) . . ?
C21 C23 H23C 110.3(18) . . ?
H23A C23 H23C 108(3) . . ?
H23B C23 H23C 111(2) . . ?
C1 N1 C14 115.1(2) . . ?
C1 N1 S1 118.84(16) . . ?
C14 N1 S1 119.53(16) . . ?
O3 N2 O4 125.1(2) . . ?
O3 N2 C12 118.2(2) . . ?
O4 N2 C12 116.6(2) . . ?
O2 S1 O1 118.84(11) . . ?
O2 S1 N1 109.32(11) . . ?
O1 S1 N1 107.40(10) . . ?
O2 S1 C13 107.58(11) . . ?
O1 S1 C13 108.28(11) . . ?
N1 S1 C13 104.52(11) . . ?

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
N1 C1 C2 C3 114.4(3) . . . . ?
N1 C1 C2 C7 -71.2(3) . . . . ?
C7 C2 C3 C4 0.5(4) . . . . ?
C1 C2 C3 C4 175.0(2) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C5 C6 C7 C2 -0.8(4) . . . . ?
C5 C6 C7 C8 177.2(2) . . . . ?
C3 C2 C7 C6 0.3(4) . . . . ?
C1 C2 C7 C6 -174.2(2) . . . . ?
C3 C2 C7 C8 -177.7(2) . . . . ?
C1 C2 C7 C8 7.9(4) . . . . ?
C6 C7 C8 C9 49.7(3) . . . . ?
C2 C7 C8 C9 -132.3(3) . . . . ?
C6 C7 C8 C13 -125.2(3) . . . . ?
C2 C7 C8 C13 52.8(3) . . . . ?
C13 C8 C9 C10 -1.0(4) . . . . ?
C7 C8 C9 C10 -176.1(3) . . . . ?
C8 C9 C10 C11 2.7(4) . . . . ?
C9 C10 C11 C12 -1.4(4) . . . . ?
C10 C11 C12 C13 -1.8(4) . . . . ?
C10 C11 C12 N2 172.9(2) . . . . ?
C11 C12 C13 C8 3.5(4) . . . . ?
N2 C12 C13 C8 -170.9(2) . . . . ?
C11 C12 C13 S1 -172.4(2) . . . . ?
N2 C12 C13 S1 13.3(3) . . . . ?
C9 C8 C13 C12 -2.1(4) . . . . ?
C7 C8 C13 C12 172.9(2) . . . . ?
C9 C8 C13 S1 174.0(2) . . . . ?
C7 C8 C13 S1 -11.0(3) . . . . ?
N1 C14 C15 C16 -81.5(3) . . . . ?
C21 C14 C15 C16 153.0(2) . . . . ?
N1 C14 C15 C20 94.8(3) . . . . ?
C21 C14 C15 C20 -30.7(3) . . . . ?
C20 C15 C16 C17 -1.0(4) . . . . ?
C14 C15 C16 C17 175.4(2) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C17 C18 C19 C20 -0.6(4) . . . . ?
C18 C19 C20 C15 -0.1(4) . . . . ?
C16 C15 C20 C19 1.0(4) . . . . ?
C14 C15 C20 C19 -175.4(2) . . . . ?
N1 C14 C21 C22 53.9(3) . . . . ?
C15 C14 C21 C22 179.6(2) . . . . ?
N1 C14 C21 C23 175.5(3) . . . . ?
C15 C14 C21 C23 -58.9(3) . . . . ?
C2 C1 N1 C14 176.5(2) . . . . ?
C2 C1 N1 S1 24.9(3) . . . . ?
C15 C14 N1 C1 -43.9(3) . . . . ?
C21 C14 N1 C1 85.1(3) . . . . ?
C15 C14 N1 S1 107.4(2) . . . . ?
C21 C14 N1 S1 -123.6(2) . . . . ?
C11 C12 N2 O3 77.6(3) . . . . ?
C13 C12 N2 O3 -107.6(3) . . . . ?
C11 C12 N2 O4 -99.4(3) . . . . ?
C13 C12 N2 O4 75.4(3) . . . . ?
C1 N1 S1 O2 -61.9(2) . . . . ?
C14 N1 S1 O2 147.90(17) . . . . ?
C1 N1 S1 O1 167.9(2) . . . . ?
C14 N1 S1 O1 17.7(2) . . . . ?
C1 N1 S1 C13 53.0(2) . . . . ?
C14 N1 S1 C13 -97.18(19) . . . . ?
C12 C13 S1 O2 -130.0(2) . . . . ?
C8 C13 S1 O2 54.1(2) . . . . ?
C12 C13 S1 O1 -0.4(2) . . . . ?
C8 C13 S1 O1 -176.30(19) . . . . ?
C12 C13 S1 N1 113.8(2) . . . . ?
C8 C13 S1 N1 -62.0(2) . . . . ?

# END of CIF
####################################################################### 
# 
# 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_atm1
_database_code_depnum_ccdc_archive 'CCDC 1008372'
_audit_update_record             
;
2014-06-14 deposited with the CCDC.
2017-11-17 downloaded from the CCDC.
;

_audit_creation_date             2013-06-24T11:19:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
6,7-dihydro-5-(1-methylethyl)-6-[(2-nitrophenyl)sulfonyl]-5H-dibenz[c,e]azepine
;
_chemical_formula_moiety         'C23 H22 N2 O4 S1'
_chemical_formula_sum            'C23 H22 N2 O4 S'
_chemical_formula_weight         422.48
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.1508(10)
_cell_length_b                   14.2203(12)
_cell_length_c                   14.6966(14)
_cell_angle_alpha                90
_cell_angle_beta                 106.099(10)
_cell_angle_gamma                90
_cell_volume                     2038.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      3
_cell_measurement_theta_max      27
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81442
_exptl_absorpt_correction_T_max  1.00000
_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.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_number            6500
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.189
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.99
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_point_group_measured_fraction_ful 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.99
_reflns_number_total             4126
_reflns_number_gt                2742
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0175P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4126
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.101
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.075

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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
C1 C 0.9030(3) 0.8199(2) 0.5478(2) 0.0163(7) Uani 1 d . .
H1A H 0.977 0.8638 0.5503 0.02 Uiso 1 calc . .
H1B H 0.8996 0.8087 0.6122 0.02 Uiso 1 calc . .
C2 C 0.7696(3) 0.8638(2) 0.4925(2) 0.0144(7) Uani 1 d . .
C3 C 0.7689(3) 0.9444(2) 0.4391(2) 0.0195(8) Uani 1 d . .
H3 H 0.8515 0.9694 0.4345 0.023 Uiso 1 calc . .
C4 C 0.6473(3) 0.9882(2) 0.3927(2) 0.0218(8) Uani 1 d . .
H4 H 0.6482 1.0421 0.3571 0.026 Uiso 1 calc . .
C5 C 0.5247(4) 0.9515(2) 0.3995(2) 0.0219(8) Uani 1 d . .
H5 H 0.4426 0.9812 0.3693 0.026 Uiso 1 calc . .
C6 C 0.5236(3) 0.8702(2) 0.4515(2) 0.0195(8) Uani 1 d . .
H6 H 0.4405 0.8454 0.4554 0.023 Uiso 1 calc . .
C7 C 0.6460(3) 0.8253(2) 0.4980(2) 0.0153(7) Uani 1 d . .
C8 C 0.6423(3) 0.7358(2) 0.5490(2) 0.0143(7) Uani 1 d . .
C9 C 0.5555(3) 0.7267(2) 0.6069(2) 0.0202(8) Uani 1 d . .
H9 H 0.4999 0.7771 0.6126 0.024 Uiso 1 calc . .
C10 C 0.5498(3) 0.6448(2) 0.6562(2) 0.0253(8) Uani 1 d . .
H10 H 0.4919 0.6405 0.6952 0.03 Uiso 1 calc . .
C11 C 0.6310(3) 0.5691(2) 0.6469(2) 0.0228(8) Uani 1 d . .
H11 H 0.6274 0.5135 0.6796 0.027 Uiso 1 calc . .
C12 C 0.7172(3) 0.5763(2) 0.5892(2) 0.0194(8) Uani 1 d . .
H12 H 0.7706 0.5249 0.5828 0.023 Uiso 1 calc . .
C13 C 0.7255(3) 0.6591(2) 0.5405(2) 0.0151(7) Uani 1 d . .
C14 C 0.8187(3) 0.6610(2) 0.47484(19) 0.0142(7) Uani 1 d . .
H14 H 0.8618 0.5989 0.4799 0.017 Uiso 1 calc . .
C15 C 0.7404(3) 0.6739(2) 0.36931(19) 0.0152(7) Uani 1 d . .
H15 H 0.6794 0.7283 0.3635 0.018 Uiso 1 calc . .
C16 C 0.6529(3) 0.5865(2) 0.3365(2) 0.0253(8) Uani 1 d . .
H16A H 0.6035 0.5931 0.2709 0.038 Uiso 1 calc . .
H16B H 0.5891 0.5792 0.3735 0.038 Uiso 1 calc . .
H16C H 0.711 0.5321 0.3444 0.038 Uiso 1 calc . .
C17 C 0.8376(3) 0.6911(2) 0.30873(19) 0.0222(8) Uani 1 d . .
H17A H 0.8786 0.7522 0.3227 0.033 Uiso 1 calc . .
H17B H 0.7876 0.688 0.243 0.033 Uiso 1 calc . .
H17C H 0.9081 0.644 0.3223 0.033 Uiso 1 calc . .
C18 C 1.1089(3) 0.6592(2) 0.6686(2) 0.0152(7) Uani 1 d . .
C19 C 1.0602(3) 0.5723(2) 0.6868(2) 0.0160(7) Uani 1 d . .
H19 H 1.0226 0.5313 0.6371 0.019 Uiso 1 calc . .
C20 C 1.0673(3) 0.5458(2) 0.7794(2) 0.0213(8) Uani 1 d . .
H20 H 1.0331 0.4878 0.7911 0.026 Uiso 1 calc . .
C21 C 1.1250(3) 0.6055(2) 0.8536(2) 0.0204(8) Uani 1 d . .
H21 H 1.1293 0.5875 0.9152 0.024 Uiso 1 calc . .
C22 C 1.1763(3) 0.6917(2) 0.8372(2) 0.0186(8) Uani 1 d . .
H22 H 1.2153 0.7322 0.8871 0.022 Uiso 1 calc . .
C23 C 1.1686(3) 0.7166(2) 0.74505(19) 0.0126(7) Uani 1 d . .
N1 N 0.9331(2) 0.73018(17) 0.50655(16) 0.0133(6) Uani 1 d . .
N2 N 1.2327(3) 0.80840(19) 0.73545(16) 0.0173(6) Uani 1 d . .
O1 O 1.1006(2) 0.60624(14) 0.49895(13) 0.0185(5) Uani 1 d . .
O2 O 1.1803(2) 0.76810(15) 0.54982(13) 0.0181(5) Uani 1 d . .
O3 O 1.1587(2) 0.87790(15) 0.71976(15) 0.0258(6) Uani 1 d . .
O4 O 1.3569(2) 0.80868(16) 0.74869(15) 0.0263(6) Uani 1 d . .
S1 S 1.08850(8) 0.69090(5) 0.54861(5) 0.0143(2) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N1 1.481(4) . ?
C1 C2 1.508(4) . ?
C2 C3 1.388(4) . ?
C2 C7 1.391(4) . ?
C3 C4 1.381(4) . ?
C4 C5 1.379(4) . ?
C5 C6 1.388(4) . ?
C6 C7 1.396(4) . ?
C7 C8 1.484(4) . ?
C8 C9 1.390(4) . ?
C8 C13 1.406(4) . ?
C9 C10 1.382(4) . ?
C10 C11 1.385(4) . ?
C11 C12 1.381(5) . ?
C12 C13 1.393(4) . ?
C13 C14 1.527(4) . ?
C14 N1 1.494(4) . ?
C14 C15 1.545(4) . ?
C15 C17 1.522(4) . ?
C15 C16 1.526(4) . ?
C18 C19 1.385(4) . ?
C18 C23 1.385(4) . ?
C18 S1 1.775(3) . ?
C19 C20 1.394(4) . ?
C20 C21 1.377(4) . ?
C21 C22 1.380(4) . ?
C22 C23 1.380(4) . ?
C23 N2 1.482(4) . ?
N1 S1 1.625(2) . ?
N2 O4 1.222(3) . ?
N2 O3 1.224(3) . ?
O1 S1 1.431(2) . ?
O2 S1 1.437(2) . ?

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
N1 C1 C2 113.1(2) . . ?
C3 C2 C7 119.6(3) . . ?
C3 C2 C1 120.7(3) . . ?
C7 C2 C1 119.7(3) . . ?
C4 C3 C2 121.0(3) . . ?
C5 C4 C3 119.6(3) . . ?
C4 C5 C6 120.1(3) . . ?
C5 C6 C7 120.5(3) . . ?
C2 C7 C6 119.1(3) . . ?
C2 C7 C8 121.1(3) . . ?
C6 C7 C8 119.7(3) . . ?
C9 C8 C13 118.7(3) . . ?
C9 C8 C7 119.9(3) . . ?
C13 C8 C7 121.4(3) . . ?
C10 C9 C8 121.7(3) . . ?
C9 C10 C11 119.4(3) . . ?
C12 C11 C10 119.9(3) . . ?
C11 C12 C13 121.1(3) . . ?
C12 C13 C8 119.1(3) . . ?
C12 C13 C14 118.5(3) . . ?
C8 C13 C14 122.3(3) . . ?
N1 C14 C13 112.3(2) . . ?
N1 C14 C15 112.0(2) . . ?
C13 C14 C15 113.6(2) . . ?
C17 C15 C16 111.2(3) . . ?
C17 C15 C14 111.7(2) . . ?
C16 C15 C14 108.3(2) . . ?
C19 C18 C23 117.9(3) . . ?
C19 C18 S1 118.0(2) . . ?
C23 C18 S1 124.1(2) . . ?
C18 C19 C20 120.3(3) . . ?
C21 C20 C19 120.2(3) . . ?
C20 C21 C22 120.4(3) . . ?
C21 C22 C23 118.6(3) . . ?
C22 C23 C18 122.5(3) . . ?
C22 C23 N2 114.4(3) . . ?
C18 C23 N2 123.1(3) . . ?
C1 N1 C14 117.6(2) . . ?
C1 N1 S1 115.44(18) . . ?
C14 N1 S1 118.75(19) . . ?
O4 N2 O3 125.4(3) . . ?
O4 N2 C23 116.6(3) . . ?
O3 N2 C23 117.8(3) . . ?
O1 S1 O2 120.13(14) . . ?
O1 S1 N1 107.87(12) . . ?
O2 S1 N1 107.45(12) . . ?
O1 S1 C18 106.87(13) . . ?
O2 S1 C18 106.54(13) . . ?
N1 S1 C18 107.39(14) . . ?

# END of CIF
