# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_exp_6370
_database_code_depnum_ccdc_archive 'CCDC 1406419'
_audit_update_record             
;
2015-06-12 deposited with the CCDC.
2015-07-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
6aR,7S,10aS)-2-bromo-7-(4-chlorophenyl)-6a-nitro-7,8,10,10a-tetrahydro-6H-benzo[c]chromen-9(6aH)-one
_chemical_name_common            ?
_chemical_melting_point          436--439
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 Br Cl N O4'
_chemical_formula_weight         436.68
_chemical_absolute_configuration rm

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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   10.2089(8)
_cell_length_b                   6.5207(6)
_cell_length_c                   13.9304(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.383(7)
_cell_angle_gamma                90.00
_cell_volume                     917.43(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1129
_cell_measurement_theta_min      3.1550
_cell_measurement_theta_max      50.4040

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    4.610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7093
_exptl_absorpt_correction_T_max  0.7385
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5399
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_sigmaI/netI    0.0974
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         67.24
_reflns_number_total             3243
_reflns_number_gt                1926
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0691P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         3243
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.1798
_refine_ls_wR_factor_gt          0.1488
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.43143(12) 0.8897(2) 0.06825(9) 0.1068(6) Uani 1 1 d . . .
Cl1 Cl 0.7811(2) 0.3340(4) 0.45127(16) 0.0703(7) Uani 1 1 d . . .
N1 N 0.2244(7) 0.6396(11) 0.2469(6) 0.0584(19) Uani 1 1 d . . .
O1 O 0.2704(7) 0.7346(11) 0.3170(6) 0.090(2) Uani 1 1 d . . .
O2 O 0.2442(7) 0.6752(10) 0.1624(5) 0.0703(18) Uani 1 1 d . . .
O3 O 0.0323(6) -0.0138(10) 0.0511(4) 0.0663(17) Uani 1 1 d . . .
O4 O 0.0162(6) 0.6421(11) 0.3747(4) 0.0726(19) Uani 1 1 d . . .
C1 C -0.2938(9) 0.8044(14) 0.1641(7) 0.061(2) Uani 1 1 d . . .
C2 C -0.2840(9) 0.8763(16) 0.2584(7) 0.073(3) Uani 1 1 d . . .
H2 H -0.3485 0.9649 0.2748 0.087 Uiso 1 1 calc R . .
C3 C -0.1830(10) 0.8209(15) 0.3271(7) 0.071(3) Uani 1 1 d . . .
H3 H -0.1773 0.8709 0.3901 0.086 Uiso 1 1 calc R . .
C4 C -0.0860(9) 0.6854(15) 0.3011(6) 0.062(2) Uani 1 1 d . . .
C5 C -0.0932(8) 0.6087(13) 0.2090(7) 0.054(2) Uani 1 1 d . . .
C6 C -0.1970(9) 0.6704(14) 0.1397(6) 0.059(2) Uani 1 1 d . . .
H6 H -0.2023 0.6222 0.0764 0.071 Uiso 1 1 calc R . .
C7 C 0.0920(8) 0.4630(15) 0.3594(6) 0.060(2) Uani 1 1 d . . .
H7A H 0.0400 0.3420 0.3688 0.072 Uiso 1 1 calc R . .
H7B H 0.1708 0.4600 0.4075 0.072 Uiso 1 1 calc R . .
C8 C 0.1332(8) 0.4543(12) 0.2584(5) 0.0481(19) Uani 1 1 d . . .
C9 C 0.0127(7) 0.4643(12) 0.1791(6) 0.0467(19) Uani 1 1 d . . .
H9 H 0.0422 0.5222 0.1210 0.056 Uiso 1 1 calc R . .
C10 C -0.0411(9) 0.2475(13) 0.1531(7) 0.059(2) Uani 1 1 d . . .
H10A H -0.0624 0.1798 0.2108 0.071 Uiso 1 1 calc R . .
H10B H -0.1214 0.2568 0.1065 0.071 Uiso 1 1 calc R . .
C11 C 0.0634(9) 0.1223(13) 0.1096(6) 0.053(2) Uani 1 1 d . . .
C12 C 0.2042(9) 0.1821(13) 0.1442(7) 0.054(2) Uani 1 1 d . . .
H12A H 0.2308 0.2895 0.1029 0.064 Uiso 1 1 calc R . .
H12B H 0.2616 0.0648 0.1402 0.064 Uiso 1 1 calc R . .
C13 C 0.2189(8) 0.2571(13) 0.2474(6) 0.051(2) Uani 1 1 d . . .
H13 H 0.1793 0.1495 0.2830 0.061 Uiso 1 1 calc R . .
C14 C 0.3622(8) 0.2763(12) 0.2984(6) 0.0470(19) Uani 1 1 d . . .
C15 C 0.3962(9) 0.2141(14) 0.3921(6) 0.062(2) Uani 1 1 d . . .
H15 H 0.3314 0.1571 0.4243 0.075 Uiso 1 1 calc R . .
C16 C 0.5245(9) 0.2330(14) 0.4412(7) 0.062(2) Uani 1 1 d . . .
H16 H 0.5454 0.1906 0.5053 0.074 Uiso 1 1 calc R . .
C17 C 0.6188(8) 0.3155(13) 0.3926(6) 0.053(2) Uani 1 1 d . . .
C18 C 0.5893(7) 0.3766(15) 0.2973(5) 0.056(2) Uani 1 1 d . . .
H18 H 0.6547 0.4319 0.2651 0.068 Uiso 1 1 calc R . .
C19 C 0.4618(8) 0.3550(13) 0.2502(5) 0.053(2) Uani 1 1 d . . .
H19 H 0.4418 0.3934 0.1854 0.064 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.876(8) . ?
Cl1 C17 1.742(8) . ?
N1 O1 1.193(9) . ?
N1 O2 1.245(10) . ?
N1 C8 1.548(10) . ?
O3 C11 1.216(9) . ?
O4 C4 1.381(10) . ?
O4 C7 1.435(10) . ?
C1 C2 1.385(12) . ?
C1 C6 1.398(11) . ?
C2 C3 1.349(12) . ?
C3 C4 1.413(13) . ?
C4 C5 1.369(12) . ?
C5 C6 1.385(11) . ?
C5 C9 1.536(11) . ?
C7 C8 1.527(10) . ?
C8 C9 1.530(10) . ?
C8 C13 1.575(11) . ?
C9 C10 1.540(11) . ?
C10 C11 1.535(12) . ?
C11 C12 1.500(12) . ?
C12 C13 1.505(12) . ?
C13 C14 1.535(10) . ?
C14 C15 1.362(11) . ?
C14 C19 1.396(11) . ?
C15 C16 1.392(11) . ?
C16 C17 1.365(12) . ?
C17 C18 1.376(11) . ?
C18 C19 1.376(10) . ?

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 N1 O2 125.3(9) . . ?
O1 N1 C8 119.5(8) . . ?
O2 N1 C8 115.2(7) . . ?
C4 O4 C7 114.9(6) . . ?
C2 C1 C6 119.1(8) . . ?
C2 C1 Br1 121.2(7) . . ?
C6 C1 Br1 119.7(7) . . ?
C3 C2 C1 121.6(9) . . ?
C2 C3 C4 118.5(9) . . ?
C5 C4 O4 123.6(9) . . ?
C5 C4 C3 121.6(9) . . ?
O4 C4 C3 114.8(8) . . ?
C4 C5 C6 118.6(8) . . ?
C4 C5 C9 122.3(8) . . ?
C6 C5 C9 119.1(8) . . ?
C5 C6 C1 120.6(8) . . ?
O4 C7 C8 113.3(7) . . ?
C7 C8 C9 111.3(6) . . ?
C7 C8 N1 108.5(7) . . ?
C9 C8 N1 108.9(6) . . ?
C7 C8 C13 110.6(7) . . ?
C9 C8 C13 111.4(6) . . ?
N1 C8 C13 106.0(6) . . ?
C8 C9 C5 110.7(6) . . ?
C8 C9 C10 110.6(6) . . ?
C5 C9 C10 112.7(7) . . ?
C11 C10 C9 109.7(7) . . ?
O3 C11 C12 123.3(8) . . ?
O3 C11 C10 121.6(8) . . ?
C12 C11 C10 115.1(7) . . ?
C11 C12 C13 110.4(8) . . ?
C12 C13 C14 115.1(7) . . ?
C12 C13 C8 112.2(7) . . ?
C14 C13 C8 113.2(7) . . ?
C15 C14 C19 117.9(8) . . ?
C15 C14 C13 120.7(8) . . ?
C19 C14 C13 121.3(7) . . ?
C14 C15 C16 122.3(9) . . ?
C17 C16 C15 118.2(8) . . ?
C16 C17 C18 121.4(8) . . ?
C16 C17 Cl1 119.1(7) . . ?
C18 C17 Cl1 119.5(7) . . ?
C19 C18 C17 119.3(8) . . ?
C18 C19 C14 120.9(7) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        67.24
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.074
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane/ethyl acetate'
