# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_a20190047_rm1098rem
_database_code_depnum_ccdc_archive 'CCDC 2010938'
loop_
_audit_author_name
_audit_author_address
'Leire San Felices'
;Universidad del Pais Vasco UPV EHU
Spain
;
_audit_update_record             
;
2020-06-19 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;

_audit_creation_date             2020-06-19T16:02:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
(4S,4aR,11aR)-7-bromo-11a-hydroxy-4-(nitromethyl)-1,2,3,4,4a,10,11,11a-octahydro-5H-dibenzo[a,d][7]annulen-5-one
_chemical_formula_moiety         'C16 H18 Br N O4'
_chemical_formula_sum            'C16 H18 Br N O4'
_chemical_formula_weight         368.22
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

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

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a                   10.42782(17)
_cell_length_b                   7.69850(11)
_cell_length_c                   11.51764(17)
_cell_angle_alpha                90
_cell_angle_beta                 106.5299(17)
_cell_angle_gamma                90
_cell_volume                     886.41(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    11475
_cell_measurement_theta_min      3.991
_cell_measurement_theta_max      74.678

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

_exptl_crystal_size_max          0.651
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.11
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.38
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 3 6 0.0513
0 -5 2 0.098
0 4 -3 0.023
0 1 -1 0.0279
0 -2 -7 0.0498
-1 2 7 0.0426
4 2 3 0.1396
-7 0 4 0.3263
-3 2 7 0.1059

_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    3.303
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.308
_exptl_absorpt_correction_T_max  0.781

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

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.1483667
_diffrn_orient_matrix_ub_12      0.038815
_diffrn_orient_matrix_ub_13      -0.0632953
_diffrn_orient_matrix_ub_21      0.0400323
_diffrn_orient_matrix_ub_22      0.1707609
_diffrn_orient_matrix_ub_23      -0.0501965
_diffrn_orient_matrix_ub_31      0.0111281
_diffrn_orient_matrix_ub_32      -0.0968558
_diffrn_orient_matrix_ub_33      -0.113781
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_number            16349
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4
_diffrn_reflns_theta_max         74.77
_diffrn_reflns_theta_full        74.77
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_reflns_number_total             3542
_reflns_number_gt                3346
_reflns_threshold_expression     >2sigma(I)
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -15.00   1.00    1.00    --  -41.88 -57.00  30.00   98
  2  ω   -116.00 -17.00   1.00    1.00    --  -41.88 -38.00 -90.00   99
  3  ω    -83.00 -18.00   1.00    1.00    --  -41.88 -38.00  90.00   65
  4  ω      6.00  66.00   1.00    1.00    --   41.88-125.00  90.00   60
  5  ω      4.00  51.00   1.00    1.00    --   41.88-125.00 -90.00   47
  6  ω     43.00  70.00   1.00    1.00    --  109.18-125.00   0.00   27
  7  ω     34.00  69.00   1.00    1.00    --  109.18 -30.00  30.00   35
  8  ω     38.00 143.00   1.00    1.00    --  109.18 -83.00  17.00  105
  9  ω     87.00 158.00   1.00    1.00    --  109.18  61.00 -90.00   71
 10  ω    128.00 155.00   1.00    1.00    --  109.18  45.00  60.00   27
 11  ω     36.00  61.00   1.00    1.00    --  109.18 -45.00   0.00   25
 12  ω     45.00 117.00   1.00    1.00    --  109.18-125.00-150.00   72
 13  ω     33.00  62.00   1.00    1.00    --  109.18 -30.00 -30.00   29
 14  ω     36.00  64.00   1.00    1.00    --  109.18 -45.00 -60.00   28
 15  ω     84.00 111.00   1.00    1.00    --  109.18  45.00  60.00   27
 16  ω     61.00 145.00   1.00    1.00    --  109.18  15.00 -90.00   84
 17  ω     33.00  61.00   1.00    1.00    --  109.18 -30.00-150.00   28
 18  ω     78.00 155.00   1.00    1.00    --  109.18  77.00 150.00   77
 19  ω     84.00 114.00   1.00    1.00    --  109.18-125.00   0.00   30
 20  ω     76.00 135.00   1.00    1.00    --  109.18 -15.00-180.00   59
 21  ω     39.00  66.00   1.00    1.00    --  109.18 -30.00   0.00   27
 22  ω     30.00  57.00   1.00    1.00    --  109.18 -15.00-180.00   27
 23  ω    -50.00 -18.00   1.00    1.00    --  -41.88 -57.00 120.00   32
 24  ω     41.00  93.00   1.00    1.00    --   41.88-125.00 -60.00   52
 25  ω     39.00  69.00   1.00    1.00    --  109.18 -45.00 150.00   30
 26  ω     41.00  82.00   1.00    1.00    --  109.18 -94.00 -60.00   41
 27  ω     33.00  62.00   1.00    1.00    --  109.18 -30.00  90.00   29
 28  ω     68.00 116.00   1.00    1.00    --  109.18-125.00  30.00   48
 29  ω     49.00  76.00   1.00    1.00    --  109.18 -45.00  30.00   27
 30  ω     36.00  61.00   1.00    1.00    --  109.18 -45.00-150.00   25
 31  ω     36.00  86.00   1.00    1.00    --  109.18 -94.00-120.00   50
 32  ω   -114.00 -14.00   1.00    1.00    --  -41.88 -57.00-150.00  100
 33  ω   -118.00  -9.00   1.00    1.00    --  -41.88 -77.00 150.00  109
 34  ω    -98.00  -2.00   1.00    1.00    --  -41.88 125.00 120.00   96
 35  ω    -30.00  70.00   1.00    1.00    --   41.88 -57.00 -90.00  100
 36  ω      9.00 118.00   1.00    1.00    --   41.88  77.00   0.00  109
 37  ω   -118.00  -9.00   1.00    1.00    --  -41.88 -77.00-120.00  109
 38  ω   -118.00  -9.00   1.00    1.00    --  -41.88 -77.00  30.00  109
 39  ω   -118.00  -9.00   1.00    1.00    --  -41.88 -77.00-180.00  109
 40  ω   -118.00  -9.00   1.00    1.00    --  -41.88 -77.00 -60.00  109
 41  ω    -66.00  32.00   1.00    1.00    --  -41.88  38.00-180.00   98
 42  ω   -114.00 -14.00   1.00    1.00    --  -41.88 -57.00  60.00  100
 43  ω   -118.00  -9.00   1.00    1.00    --  -41.88 -77.00  60.00  109
 44  ω   -116.00 -17.00   1.00    1.00    --  -41.88 -38.00  60.00   99
 45  ω   -114.00 -14.00   1.00    1.00    --  -41.88 -57.00 -30.00  100
 46  ω   -114.00 -14.00   1.00    1.00    --  -41.88 -57.00  30.00  100
 47  ω   -122.00  -1.00   1.00    1.00    --  -41.88 -19.00 -30.00  121
 48  ω   -114.00 -14.00   1.00    1.00    --  -41.88 -57.00   0.00  100
 49  ω    -46.00 130.00   1.00    1.00    --   41.88   0.00-180.00  176
;

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

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'ShelXH-1997 (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   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 > 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.
;
_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)+(0.1314P)²+0.3789P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0109(17)
_refine_ls_number_reflns         3542
_refine_ls_number_parameters     201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1885
_refine_ls_wR_factor_gt          0.185
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_restrained_S_all      1.195
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_diff_density_max         1.847
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.193

#----------------------------------------------------------------------------#
#                   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 0.0181 0.0091 '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 0.0311 0.018 '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'
Br Br -0.6763 1.2805 '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
Br1 Br -0.32779(4) -0.21104(9) -0.10170(5) 0.0384(3) Uani 1 d . .
C15 C -0.6649(8) 0.4643(9) -0.2098(7) 0.0402(16) Uani 1 d . .
H15A H -0.6007 0.5579 -0.2021 0.048 Uiso 1 calc . .
H15B H -0.7131 0.484 -0.1503 0.048 Uiso 1 calc . .
C10 C -1.1238(6) 0.2906(12) -0.2456(5) 0.0391(11) Uani 1 d . .
H10A H -1.2132 0.243 -0.2607 0.047 Uiso 1 calc . .
H10B H -1.0909 0.3177 -0.16 0.047 Uiso 1 calc . .
C3 C -0.6461(6) 0.1319(8) -0.2203(5) 0.0273(12) Uani 1 d . .
C4 C -0.5898(5) 0.2949(9) -0.1809(4) 0.0302(9) Uani 1 d . .
C5 C -0.4536(5) 0.3000(9) -0.1167(4) 0.0330(11) Uani 1 d . .
H5 H -0.4144 0.4067 -0.0899 0.04 Uiso 1 calc . .
O1 O -0.8247(4) -0.0170(5) -0.3566(3) 0.0326(8) Uani 1 d . .
C9 C -1.0319(5) 0.1542(7) -0.2783(5) 0.0302(11) Uani 1 d . .
H9 H -1.0697 0.1267 -0.3644 0.036 Uiso 1 calc . .
C1 C -0.4353(6) -0.0062(7) -0.1322(5) 0.0305(11) Uani 1 d . .
C6 C -0.3757(6) 0.1514(8) -0.0920(5) 0.0332(12) Uani 1 d . .
H6 H -0.2855 0.1576 -0.0493 0.04 Uiso 1 calc . .
C2 C -0.5687(5) -0.0175(7) -0.1982(5) 0.0293(11) Uani 1 d . .
H2 H -0.606 -0.1242 -0.2274 0.035 Uiso 1 calc . .
C14 C -0.7638(7) 0.4718(8) -0.3358(6) 0.0400(14) Uani 1 d . .
H14A H -0.7257 0.4095 -0.3913 0.048 Uiso 1 calc . .
H14B H -0.7742 0.5921 -0.3618 0.048 Uiso 1 calc . .
C16 C -1.0282(6) -0.0148(8) -0.2076(5) 0.0363(12) Uani 1 d . .
H16A H -1.119 -0.0523 -0.2149 0.044 Uiso 1 calc . .
H16B H -0.985 -0.1045 -0.2422 0.044 Uiso 1 calc . .
C13 C -0.9046(6) 0.3955(7) -0.3465(5) 0.0326(12) Uani 1 d . .
C11 C -1.1298(7) 0.4559(10) -0.3188(6) 0.0461(16) Uani 1 d . .
H11A H -1.1773 0.4322 -0.4027 0.055 Uiso 1 calc . .
H11B H -1.1803 0.5428 -0.2894 0.055 Uiso 1 calc . .
C7 C -0.7901(5) 0.1064(7) -0.2871(5) 0.0271(11) Uani 1 d . .
C8 C -0.8927(5) 0.2329(7) -0.2631(4) 0.0275(10) Uani 1 d . .
H8 H -0.8587 0.2725 -0.179 0.033 Uiso 1 calc . .
C12 C -0.9935(7) 0.5284(8) -0.3124(5) 0.0406(14) Uani 1 d . .
H12A H -1.0038 0.6272 -0.3665 0.049 Uiso 1 calc . .
H12B H -0.9513 0.5691 -0.2307 0.049 Uiso 1 calc . .
O3 O -1.0158(6) 0.0707(8) -0.0083(5) 0.0521(14) Uani 1 d . .
O2 O -0.9575(4) 0.3371(6) -0.4684(3) 0.0391(10) Uani 1 d . .
H2A H -1.0054 0.4129 -0.5085 0.059 Uiso 1 calc . .
O4 O -0.8375(4) -0.0316(7) -0.0419(4) 0.0464(11) Uani 1 d . .
N1 N -0.9546(5) 0.0077(7) -0.0770(5) 0.0373(11) 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
Br1 C1 1.909(6) . ?
C15 C4 1.509(10) . ?
C15 C14 1.524(9) . ?
C10 C9 1.539(9) . ?
C10 C11 1.518(11) . ?
C3 C4 1.405(9) . ?
C3 C2 1.386(8) . ?
C3 C7 1.493(8) . ?
C4 C5 1.403(7) . ?
C5 C6 1.385(9) . ?
O1 C7 1.228(7) . ?
C9 C16 1.530(8) . ?
C9 C8 1.536(7) . ?
C1 C6 1.382(8) . ?
C1 C2 1.385(7) . ?
C14 C13 1.554(9) . ?
C16 N1 1.492(8) . ?
C13 C8 1.562(7) . ?
C13 C12 1.506(8) . ?
C13 O2 1.427(6) . ?
C11 C12 1.509(10) . ?
C7 C8 1.529(8) . ?
O3 N1 1.248(8) . ?
O4 N1 1.210(6) . ?

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
C4 C15 C14 114.2(5) . . ?
C11 C10 C9 111.5(5) . . ?
C4 C3 C7 123.4(5) . . ?
C2 C3 C4 120.9(5) . . ?
C2 C3 C7 115.6(5) . . ?
C3 C4 C15 123.9(4) . . ?
C5 C4 C15 118.4(6) . . ?
C5 C4 C3 117.6(6) . . ?
C6 C5 C4 122.1(6) . . ?
C16 C9 C10 111.9(5) . . ?
C16 C9 C8 113.3(4) . . ?
C8 C9 C10 109.7(5) . . ?
C6 C1 Br1 118.6(4) . . ?
C6 C1 C2 121.6(5) . . ?
C2 C1 Br1 119.7(4) . . ?
C1 C6 C5 118.4(5) . . ?
C1 C2 C3 119.3(5) . . ?
C15 C14 C13 115.4(5) . . ?
N1 C16 C9 111.4(4) . . ?
C14 C13 C8 110.3(4) . . ?
C12 C13 C14 111.2(5) . . ?
C12 C13 C8 109.3(5) . . ?
O2 C13 C14 106.8(5) . . ?
O2 C13 C8 107.1(4) . . ?
O2 C13 C12 112.1(4) . . ?
C12 C11 C10 113.2(5) . . ?
C3 C7 C8 118.4(5) . . ?
O1 C7 C3 120.2(5) . . ?
O1 C7 C8 121.3(5) . . ?
C9 C8 C13 109.8(4) . . ?
C7 C8 C9 114.5(4) . . ?
C7 C8 C13 109.7(4) . . ?
C13 C12 C11 112.1(5) . . ?
O3 N1 C16 118.4(5) . . ?
O4 N1 C16 119.2(5) . . ?
O4 N1 O3 122.3(6) . . ?




# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# 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_a20180380_rm998f1
_database_code_depnum_ccdc_archive 'CCDC 2010939'
loop_
_audit_author_name
_audit_author_address
'Leire San Felices'
;Universidad del Pais Vasco UPV EHU
Spain
;
_audit_update_record             
;
2020-06-19 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;

_audit_creation_date             2020-06-19T16:04:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 (2S,2aS,2a1S,5aR)-5a-hydroxy-2-(methoxycarbonyl)-2a,2a1,3,4,5,5a,6,7-
octahydro-2H-benzo[6,7]cyclohepta[1,2,3-cd]isoindole 1-oxide
;
_chemical_formula_moiety         'C18 H21 N O4'
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_weight         315.36
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

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

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
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'
_cell_length_a                   9.19139(11)
_cell_length_b                   11.21187(14)
_cell_length_c                   15.13619(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1559.82(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    9239
_cell_measurement_theta_min      5.594
_cell_measurement_theta_max      74.13

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

_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.82285
_exptl_absorpt_correction_T_max  1

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

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0295173
_diffrn_orient_matrix_ub_12      0.1350103
_diffrn_orient_matrix_ub_13      0.0063193
_diffrn_orient_matrix_ub_21      -0.1299989
_diffrn_orient_matrix_ub_22      0.0136756
_diffrn_orient_matrix_ub_23      0.0634675
_diffrn_orient_matrix_ub_31      0.1015605
_diffrn_orient_matrix_ub_32      -0.0217064
_diffrn_orient_matrix_ub_33      0.0793131
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_number            16448
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.91
_diffrn_reflns_theta_max         74.42
_diffrn_reflns_theta_full        74.42
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             3134
_reflns_number_gt                2946
_reflns_threshold_expression     >2sigma(I)
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -131.00  37.00   1.00    1.00    --  -42.38   0.00-120.00  168
  2  ω     83.00 108.00   1.00    1.00    --   42.38 166.00-163.00   25
  3  ω     37.00  63.00   1.00    3.00    --  107.93 -30.00 150.00   26
  4  ω     35.00  69.00   1.00    3.00    --  107.93 -30.00  60.00   34
  5  ω     33.00  66.00   1.00    3.00    --  107.93 -30.00-150.00   33
  6  ω     82.00 156.00   1.00    3.00    --  107.93  61.00   0.00   74
  7  ω     33.00 103.00   1.00    3.00    --  107.93 -94.00 150.00   70
  8  ω     34.00  67.00   1.00    3.00    --  107.93 -30.00-180.00   33
  9  ω     43.00  92.00   1.00    3.00    --  107.93-125.00 120.00   49
 10  ω     79.00 153.00   1.00    3.00    --  107.93  77.00-120.00   74
 11  ω    -89.00 -15.00   1.00    1.00    --  -42.38 -51.00-168.00   74
 12  ω    -98.00 -33.00   1.00    1.00    --  -42.38 125.00 -60.00   65
 13  ω     34.00  70.00   1.00    1.00    --   42.38-125.00-180.00   36
 14  ω      4.00  36.00   1.00    1.00    --   42.38-125.00 120.00   32
 15  ω     41.00  67.00   1.00    3.00    --  107.93 -30.00   0.00   26
 16  ω     81.00 118.00   1.00    3.00    --  107.93  30.00 -30.00   37
 17  ω     36.00  62.00   1.00    3.00    --  107.93 -30.00  90.00   26
 18  ω     39.00  65.00   1.00    3.00    --  107.93 -30.00 -90.00   26
 19  ω     35.00  63.00   1.00    3.00    --  107.93 -30.00 120.00   28
 20  ω     47.00  81.00   1.00    3.00    --  107.93 -94.00  30.00   34
 21  ω     53.00  79.00   1.00    3.00    --  107.93 -61.00  60.00   26
 22  ω    104.00 132.00   1.00    3.00    --  107.93 -61.00  60.00   28
 23  ω     42.00 141.00   1.00    3.00    --  107.93 -77.00-150.00   99
 24  ω    129.00 155.00   1.00    3.00    --  107.93  30.00 -30.00   26
 25  ω     90.00 116.00   1.00    3.00    --  107.93-125.00 120.00   26
 26  ω     79.00 113.00   1.00    3.00    --  107.93-125.00 -90.00   34
 27  ω     87.00 130.00   1.00    3.00    --  107.93  61.00  60.00   43
 28  ω     36.00  69.00   1.00    3.00    --  107.93 -30.00 -30.00   33
 29  ω     83.00 110.00   1.00    3.00    --  107.93 -94.00 -60.00   27
 30  ω    -67.00  32.00   1.00    1.00    --  -42.38  38.00  30.00   99
 31  ω   -116.00 -14.00   1.00    1.00    --  -42.38 -57.00  90.00  102
 32  ω   -119.00 -10.00   1.00    1.00    --  -42.38 -77.00-150.00  109
 33  ω   -119.00 -10.00   1.00    1.00    --  -42.38 -77.00 -60.00  109
 34  ω      2.00  71.00   1.00    1.00    --   42.38-125.00 -90.00   69
;

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

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

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

_atom_sites_solution_primary     dual
_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 > 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.
;
_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)+(0.0410P)²+0.1329P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0009(3)
_refine_ls_number_reflns         3134
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0751
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.13(16)
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.03

#----------------------------------------------------------------------------#
#                   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 0.0181 0.0091 '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 0.0311 0.018 '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'

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
O001 O 0.24394(13) 0.98837(9) 0.20230(6) 0.0311(2) Uani 1 d . .
O4 O 0.31713(11) 1.31551(10) 0.20395(7) 0.0343(3) Uani 1 d . .
O2 O 0.24751(12) 1.01159(11) 0.52349(6) 0.0358(3) Uani 1 d . .
H2 H 0.2604 1.0003 0.5764 0.054 Uiso 1 calc . .
N004 N 0.19653(12) 1.03444(10) 0.27545(7) 0.0220(2) Uani 1 d . .
C005 C 0.13489(14) 0.97997(12) 0.34259(8) 0.0211(3) Uani 1 d . .
C006 C 0.19277(16) 0.77237(13) 0.29545(10) 0.0291(3) Uani 1 d . .
H006 H 0.2582 0.8025 0.2542 0.035 Uiso 1 calc . .
C007 C 0.19442(14) 1.17643(11) 0.38682(8) 0.0208(3) Uani 1 d . .
H007 H 0.2904 1.156 0.4106 0.025 Uiso 1 calc . .
O3 O 0.46266(11) 1.17647(10) 0.26407(7) 0.0325(2) Uani 1 d . .
C009 C 0.01006(16) 0.80488(13) 0.40908(9) 0.0261(3) Uani 1 d . .
C010 C 0.20351(15) 1.16692(12) 0.28684(8) 0.0223(3) Uani 1 d . .
H010 H 0.1195 1.2054 0.259 0.027 Uiso 1 calc . .
C011 C 0.09124(15) 1.07390(11) 0.40953(8) 0.0203(3) Uani 1 d . .
H011 H -0.0083 1.0995 0.3961 0.024 Uiso 1 calc . .
C012 C 0.07845(18) 0.60469(14) 0.36486(12) 0.0393(4) Uani 1 d . .
H012 H 0.0674 0.5227 0.371 0.047 Uiso 1 calc . .
C013 C 0.11107(15) 0.85129(12) 0.34792(9) 0.0228(3) Uani 1 d . .
C014 C -0.00353(17) 0.68119(14) 0.41599(10) 0.0333(3) Uani 1 d . .
H014 H -0.0697 0.6495 0.4562 0.04 Uiso 1 calc . .
C015 C 0.34418(15) 1.21621(12) 0.24992(8) 0.0242(3) Uani 1 d . .
C016 C -0.0069(2) 0.94803(15) 0.53889(10) 0.0401(4) Uani 1 d . .
H01A H 0.0468 0.89 0.5735 0.048 Uiso 1 calc . .
H01B H -0.0785 0.9842 0.5776 0.048 Uiso 1 calc . .
C017 C -0.08723(18) 0.88194(14) 0.46545(10) 0.0340(3) Uani 1 d . .
H01C H -0.1619 0.8322 0.4918 0.041 Uiso 1 calc . .
H01D H -0.1353 0.9399 0.4279 0.041 Uiso 1 calc . .
C018 C 0.14693(16) 1.29167(12) 0.43014(10) 0.0286(3) Uani 1 d . .
H01E H 0.049 1.3123 0.4118 0.034 Uiso 1 calc . .
H01F H 0.2117 1.3562 0.4135 0.034 Uiso 1 calc . .
C019 C 0.17651(18) 0.64940(14) 0.30477(12) 0.0373(4) Uani 1 d . .
H019 H 0.2319 0.5977 0.2704 0.045 Uiso 1 calc . .
C020 C 0.15217(18) 1.27139(14) 0.53015(10) 0.0337(3) Uani 1 d . .
H02A H 0.2525 1.2605 0.5484 0.04 Uiso 1 calc . .
H02B H 0.1146 1.3415 0.56 0.04 Uiso 1 calc . .
C021 C 0.09998(16) 1.04594(13) 0.50855(8) 0.0244(3) Uani 1 d . .
C022 C 0.06346(15) 1.16265(13) 0.55780(9) 0.0274(3) Uani 1 d . .
H02C H -0.0388 1.1803 0.5488 0.033 Uiso 1 calc . .
H02D H 0.0778 1.1496 0.6206 0.033 Uiso 1 calc . .
C023 C 0.44392(19) 1.37884(15) 0.17088(12) 0.0403(4) Uani 1 d . .
H02E H 0.4132 1.4419 0.1323 0.06 Uiso 1 calc . .
H02F H 0.5051 1.3245 0.1389 0.06 Uiso 1 calc . .
H02G H 0.4972 1.4119 0.2196 0.06 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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
O001 N004 1.2972(14) . ?
O4 C015 1.3364(17) . ?
O4 C023 1.4535(18) . ?
O2 C021 1.4276(17) . ?
N004 C005 1.3141(17) . ?
N004 C010 1.4967(16) . ?
C005 C011 1.5155(17) . ?
C005 C013 1.4615(18) . ?
C006 C013 1.406(2) . ?
C006 C019 1.394(2) . ?
C007 C010 1.5194(17) . ?
C007 C011 1.5294(18) . ?
C007 C018 1.5132(18) . ?
O3 C015 1.1959(17) . ?
C009 C013 1.4105(19) . ?
C009 C014 1.396(2) . ?
C009 C017 1.508(2) . ?
C010 C015 1.5131(19) . ?
C011 C021 1.5333(16) . ?
C012 C014 1.379(3) . ?
C012 C019 1.375(3) . ?
C016 C017 1.526(2) . ?
C016 C021 1.543(2) . ?
C018 C020 1.532(2) . ?
C020 C022 1.525(2) . ?
C021 C022 1.5430(19) . ?

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
C015 O4 C023 115.92(12) . . ?
O001 N004 C005 128.31(11) . . ?
O001 N004 C010 118.63(10) . . ?
C005 N004 C010 112.99(11) . . ?
N004 C005 C011 107.95(11) . . ?
N004 C005 C013 124.48(12) . . ?
C013 C005 C011 127.55(11) . . ?
C019 C006 C013 120.53(15) . . ?
C010 C007 C011 101.84(10) . . ?
C018 C007 C010 120.48(11) . . ?
C018 C007 C011 111.44(11) . . ?
C013 C009 C017 123.39(13) . . ?
C014 C009 C013 118.32(14) . . ?
C014 C009 C017 118.26(13) . . ?
N004 C010 C007 100.49(10) . . ?
N004 C010 C015 110.88(11) . . ?
C015 C010 C007 112.90(11) . . ?
C005 C011 C007 102.00(10) . . ?
C005 C011 C021 119.84(11) . . ?
C007 C011 C021 109.93(11) . . ?
C019 C012 C014 120.17(14) . . ?
C006 C013 C005 120.66(12) . . ?
C006 C013 C009 119.34(13) . . ?
C009 C013 C005 119.93(12) . . ?
C012 C014 C009 121.78(15) . . ?
O4 C015 C010 109.73(12) . . ?
O3 C015 O4 124.96(13) . . ?
O3 C015 C010 125.17(12) . . ?
C017 C016 C021 115.89(12) . . ?
C009 C017 C016 113.78(14) . . ?
C007 C018 C020 107.00(12) . . ?
C012 C019 C006 119.85(16) . . ?
C022 C020 C018 111.90(12) . . ?
O2 C021 C011 105.05(10) . . ?
O2 C021 C016 111.44(12) . . ?
O2 C021 C022 111.03(11) . . ?
C011 C021 C016 113.77(12) . . ?
C011 C021 C022 106.71(11) . . ?
C022 C021 C016 108.73(12) . . ?
C020 C022 C021 115.41(11) . . ?




# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
