# Electronic Supplementary Material (ESI) for Green 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_exp_7575
_database_code_depnum_ccdc_archive 'CCDC 1545490'
_audit_update_record             
;
2017-04-23 deposited with the CCDC.
2017-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
8'-bromo-1',2',3',3a'-tetrahydro-5'H-spiro[chromane-3,4'-pyrrolo[1,2-a]quinoline]-2,4-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Br N O3'
_chemical_formula_weight         398.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2200(12)
_cell_length_b                   8.7275(7)
_cell_length_c                   13.0899(9)
_cell_angle_alpha                71.212(7)
_cell_angle_beta                 72.443(10)
_cell_angle_gamma                79.120(10)
_cell_volume                     843.24(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2362
_cell_measurement_theta_min      3.7490
_cell_measurement_theta_max      71.3110

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    3.485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6798
_exptl_absorpt_correction_T_max  0.7004
_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         'Enhance (Cu) X-ray Source'
_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            4724
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.69
_diffrn_reflns_theta_max         67.25
_reflns_number_total             2991
_reflns_number_gt                2616
_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)+(0.0827P)²+0.3864P] 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_number_reflns         2991
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1484
_refine_ls_wR_factor_gt          0.1421
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.21480(7) -0.00527(6) 1.38847(4) 0.0890(3) Uani 1 1 d . . .
N1 N 0.5308(3) 0.2779(3) 0.9746(2) 0.0468(6) Uani 1 1 d . . .
O1 O 0.9953(3) 0.1376(3) 0.7857(2) 0.0594(6) Uani 1 1 d . . .
O2 O 0.9484(3) 0.5754(3) 0.8459(2) 0.0614(6) Uani 1 1 d . . .
O3 O 0.8440(3) 0.0294(3) 0.9533(2) 0.0576(6) Uani 1 1 d . . .
C1 C 0.4069(5) 0.0928(4) 1.2762(3) 0.0575(8) Uani 1 1 d . . .
C2 C 0.3969(4) 0.1450(4) 1.1671(3) 0.0498(7) Uani 1 1 d . . .
H2 H 0.3006 0.1321 1.1486 0.060 Uiso 1 1 calc R . .
C3 C 0.5358(4) 0.2182(3) 1.0844(2) 0.0422(6) Uani 1 1 d . . .
C4 C 0.6821(4) 0.2323(3) 1.1140(2) 0.0434(6) Uani 1 1 d . . .
C5 C 0.6832(5) 0.1756(4) 1.2260(3) 0.0568(8) Uani 1 1 d . . .
H5 H 0.7802 0.1831 1.2460 0.068 Uiso 1 1 calc R . .
C6 C 0.5450(6) 0.1084(5) 1.3084(3) 0.0659(9) Uani 1 1 d . . .
H6 H 0.5457 0.0749 1.3833 0.079 Uiso 1 1 calc R . .
C7 C 0.8360(4) 0.3051(4) 1.0283(3) 0.0461(7) Uani 1 1 d . . .
H7A H 0.9386 0.2401 1.0463 0.055 Uiso 1 1 calc R . .
H7B H 0.8376 0.4134 1.0332 0.055 Uiso 1 1 calc R . .
C8 C 0.8424(3) 0.3170(3) 0.9068(2) 0.0390(6) Uani 1 1 d . . .
C9 C 0.6560(3) 0.3792(4) 0.8922(2) 0.0412(6) Uani 1 1 d . . .
H9 H 0.6273 0.4891 0.9013 0.049 Uiso 1 1 calc R . .
C10 C 0.6256(4) 0.3848(5) 0.7817(3) 0.0604(9) Uani 1 1 d . . .
H10A H 0.6439 0.4908 0.7281 0.072 Uiso 1 1 calc R . .
H10B H 0.7022 0.3027 0.7504 0.072 Uiso 1 1 calc R . .
C11 C 0.4436(6) 0.3518(6) 0.8099(3) 0.0742(11) Uani 1 1 d . . .
H11A H 0.4291 0.2952 0.7610 0.089 Uiso 1 1 calc R . .
H11B H 0.3687 0.4528 0.8021 0.089 Uiso 1 1 calc R . .
C12 C 0.4027(4) 0.2477(4) 0.9291(3) 0.0501(7) Uani 1 1 d . . .
H12A H 0.2878 0.2792 0.9694 0.060 Uiso 1 1 calc R . .
H12B H 0.4120 0.1337 0.9328 0.060 Uiso 1 1 calc R . .
C13 C 0.9528(4) 0.4491(4) 0.8253(3) 0.0443(6) Uani 1 1 d . . .
C14 C 1.0556(4) 0.4198(4) 0.7185(3) 0.0473(7) Uani 1 1 d . . .
C15 C 1.0701(4) 0.2674(4) 0.7035(3) 0.0532(7) Uani 1 1 d . . .
C16 C 0.8931(4) 0.1509(4) 0.8871(3) 0.0433(6) Uani 1 1 d . . .
C17 C 1.1397(5) 0.5418(5) 0.6314(3) 0.0646(9) Uani 1 1 d . . .
H17 H 1.1296 0.6454 0.6396 0.078 Uiso 1 1 calc R . .
C18 C 1.2377(7) 0.5108(6) 0.5332(4) 0.0860(13) Uani 1 1 d . . .
H18 H 1.2959 0.5921 0.4758 0.103 Uiso 1 1 calc R . .
C19 C 1.2489(7) 0.3572(6) 0.5208(4) 0.0970(17) Uani 1 1 d . . .
H19 H 1.3139 0.3366 0.4541 0.116 Uiso 1 1 calc R . .
C20 C 1.1666(6) 0.2356(5) 0.6044(3) 0.0772(12) Uani 1 1 d . . .
H20 H 1.1752 0.1330 0.5950 0.093 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 1.920(4) . ?
N1 C3 1.374(4) . ?
N1 C9 1.437(4) . ?
N1 C12 1.455(4) . ?
O1 C16 1.368(4) . ?
O1 C15 1.378(4) . ?
O2 C13 1.208(4) . ?
O3 C16 1.182(4) . ?
C1 C6 1.367(6) . ?
C1 C2 1.376(5) . ?
C2 C3 1.403(4) . ?
C3 C4 1.407(4) . ?
C4 C5 1.390(4) . ?
C4 C7 1.501(5) . ?
C5 C6 1.379(6) . ?
C7 C8 1.547(4) . ?
C8 C16 1.513(4) . ?
C8 C13 1.520(4) . ?
C8 C9 1.573(4) . ?
C9 C10 1.525(4) . ?
C10 C11 1.489(5) . ?
C11 C12 1.503(5) . ?
C13 C14 1.473(4) . ?
C14 C15 1.385(5) . ?
C14 C17 1.389(5) . ?
C15 C20 1.385(5) . ?
C17 C18 1.375(6) . ?
C18 C19 1.384(7) . ?
C19 C20 1.363(7) . ?

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
C3 N1 C9 121.8(2) . . ?
C3 N1 C12 125.0(3) . . ?
C9 N1 C12 113.2(2) . . ?
C16 O1 C15 122.6(2) . . ?
C6 C1 C2 123.5(3) . . ?
C6 C1 Br1 118.8(3) . . ?
C2 C1 Br1 117.7(3) . . ?
C1 C2 C3 118.2(3) . . ?
N1 C3 C2 120.9(3) . . ?
N1 C3 C4 119.3(3) . . ?
C2 C3 C4 119.8(3) . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 C7 119.5(3) . . ?
C3 C4 C7 121.9(3) . . ?
C6 C5 C4 122.1(3) . . ?
C1 C6 C5 117.7(3) . . ?
C4 C7 C8 114.4(2) . . ?
C16 C8 C13 115.2(2) . . ?
C16 C8 C7 110.2(2) . . ?
C13 C8 C7 110.2(2) . . ?
C16 C8 C9 109.0(2) . . ?
C13 C8 C9 105.0(2) . . ?
C7 C8 C9 106.8(2) . . ?
N1 C9 C10 103.6(2) . . ?
N1 C9 C8 112.0(2) . . ?
C10 C9 C8 116.6(2) . . ?
C11 C10 C9 105.1(3) . . ?
C10 C11 C12 106.1(3) . . ?
N1 C12 C11 104.1(3) . . ?
O2 C13 C14 122.1(3) . . ?
O2 C13 C8 120.7(3) . . ?
C14 C13 C8 117.0(2) . . ?
C15 C14 C17 118.6(3) . . ?
C15 C14 C13 119.8(3) . . ?
C17 C14 C13 121.7(3) . . ?
O1 C15 C14 122.9(3) . . ?
O1 C15 C20 115.9(3) . . ?
C14 C15 C20 121.2(4) . . ?
O3 C16 O1 116.6(3) . . ?
O3 C16 C8 123.9(3) . . ?
O1 C16 C8 119.5(3) . . ?
C18 C17 C14 120.6(4) . . ?
C17 C18 C19 119.3(4) . . ?
C20 C19 C18 121.4(4) . . ?
C19 C20 C15 118.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        67.25
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.083
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ????????'
