# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_3
_database_code_depnum_ccdc_archive 'CCDC 1962713'
loop_
_audit_author_name
_audit_author_address
'Filipe Almeida Paz'
;University of Aveiro CICECO Aveiro Institute of Materials
Portugal
;
_audit_update_record             
;
2019-10-31 deposited with the CCDC.	2020-03-30 downloaded from the CCDC.
;

#=============================================================================
_audit_creation_method           'SHELXL-2018/3, manual editing plus enCIFer'
_audit_creation_date             '31 October 2019'
_shelx_SHELXL_version_number     2018/3
#=============================================================================

_chemical_name_systematic        
;
12a-bromo-6b,12a-dihydro-12H-chromeno[2',3':4,5]furo[3,2-c]quinolin-12-one 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H10 Br N O3'
_chemical_formula_sum            'C18 H10 Br N O3'
_chemical_formula_weight         368.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#=============================================================================
# CRYSTAL DATA
#=============================================================================

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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                   15.6773(18)
_cell_length_b                   6.7908(8)
_cell_length_c                   15.3495(19)
_cell_angle_alpha                90
_cell_angle_beta                 118.405(4)
_cell_angle_gamma                90
_cell_volume                     1437.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9979
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      25.59

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   0.5483
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.875
_shelx_estimated_absorpt_T_min   0.584
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
; 
  SADABS-2016/2
  Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  J. Appl. Cryst. 48 (2015) 3-10.
;

#=============================================================================
# EXPERIMENTAL DATA
#============================================================================= 

_exptl_absorpt_special_details   
;
?
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Sealed tube'
_diffrn_radiation_monochromator  'Multi-layer X-ray mirror'
_diffrn_measurement_device_type  'Bruker D8 QUEST '
_diffrn_measurement_method       'ω / φ scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25437
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.942
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2616
_reflns_number_gt                2198
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 2016.9-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37a   (Bruker, 2015)'
_computing_data_reduction        'SAINT V8.37a   (Bruker, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015b)'


#=============================================================================
# REFINEMENT DATA
#=============================================================================

_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)+(0.0147P)²+1.7098P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2616
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0562
_refine_ls_wR_factor_gt          0.0505
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.22062(2) 0.46211(4) 0.59237(2) 0.02759(9) Uani 1 1 d . . . . .
O1 O 0.36318(13) 0.7826(2) 0.56984(13) 0.0313(4) Uani 1 1 d . . . . .
O2 O 0.41115(11) 0.2364(2) 0.50656(12) 0.0236(4) Uani 1 1 d . . . . .
O3 O 0.23047(11) 0.5335(2) 0.41938(11) 0.0205(3) Uani 1 1 d . . . . .
N1 N 0.14046(14) 0.0114(3) 0.26247(16) 0.0247(5) Uani 1 1 d . . . . .
C1 C 0.29321(16) 0.4646(4) 0.51652(17) 0.0204(5) Uani 1 1 d . . . . .
C2 C 0.37770(17) 0.6071(4) 0.56968(17) 0.0224(5) Uani 1 1 d . . . . .
C3 C 0.47376(17) 0.5138(3) 0.61795(17) 0.0214(5) Uani 1 1 d . . . . .
C4 C 0.48676(17) 0.3291(4) 0.58592(17) 0.0219(5) Uani 1 1 d . . . . .
C5 C 0.57694(18) 0.2406(4) 0.62713(18) 0.0264(6) Uani 1 1 d . . . . .
H5 H 0.585197 0.115572 0.604393 0.032 Uiso 1 1 calc R U . . .
C6 C 0.65509(18) 0.3375(4) 0.70217(19) 0.0287(6) Uani 1 1 d . . . . .
H6 H 0.717191 0.276937 0.731903 0.034 Uiso 1 1 calc R U . . .
C7 C 0.64400(18) 0.5217(4) 0.7345(2) 0.0306(6) Uani 1 1 d . . . . .
H7 H 0.698460 0.586941 0.785548 0.037 Uiso 1 1 calc R U . . .
C8 C 0.55435(18) 0.6099(4) 0.69289(18) 0.0272(6) Uani 1 1 d . . . . .
H8 H 0.547002 0.736342 0.714973 0.033 Uiso 1 1 calc R U . . .
C9 C 0.31992(16) 0.2486(3) 0.50777(18) 0.0209(5) Uani 1 1 d . . . . .
H9 H 0.318753 0.162621 0.560095 0.025 Uiso 1 1 calc R U . . .
C10 C 0.24044(17) 0.1987(3) 0.40711(18) 0.0209(5) Uani 1 1 d . . . . .
C11 C 0.19514(16) 0.3683(3) 0.36110(18) 0.0198(5) Uani 1 1 d . . . . .
C12 C 0.11918(16) 0.3720(3) 0.26299(17) 0.0200(5) Uani 1 1 d . . . . .
C13 C 0.06878(16) 0.5416(4) 0.21103(17) 0.0220(5) Uani 1 1 d . . . . .
H13 H 0.086902 0.667709 0.241137 0.026 Uiso 1 1 calc R U . . .
C14 C -0.00615(17) 0.5233(4) 0.11728(18) 0.0257(6) Uani 1 1 d . . . . .
H14 H -0.040146 0.637359 0.081992 0.031 Uiso 1 1 calc R U . . .
C15 C -0.03359(18) 0.3368(4) 0.07227(19) 0.0279(6) Uani 1 1 d . . . . .
H15 H -0.087071 0.326236 0.007551 0.033 Uiso 1 1 calc R U . . .
C16 C 0.01558(18) 0.1710(4) 0.12034(19) 0.0273(6) Uani 1 1 d . . . . .
H16 H -0.003326 0.046782 0.088319 0.033 Uiso 1 1 calc R U . . .
C17 C 0.09418(17) 0.1826(4) 0.21712(18) 0.0215(5) Uani 1 1 d . . . . .
C18 C 0.21086(17) 0.0209(4) 0.35483(19) 0.0239(5) Uani 1 1 d . . . . .
H18 H 0.242663 -0.097309 0.387038 0.029 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.978(2) . ?
O1 C2 1.214(3) . ?
O2 C4 1.382(3) . ?
O2 C9 1.442(3) . ?
O3 C11 1.376(3) . ?
O3 C1 1.419(3) . ?
N1 C18 1.320(3) . ?
N1 C17 1.372(3) . ?
C1 C2 1.526(3) . ?
C1 C9 1.549(3) . ?
C2 C3 1.469(3) . ?
C3 C4 1.397(3) . ?
C3 C8 1.401(3) . ?
C4 C5 1.382(3) . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.374(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.491(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.361(3) . ?
C10 C18 1.401(3) . ?
C11 C12 1.407(3) . ?
C12 C13 1.410(3) . ?
C12 C17 1.428(3) . ?
C13 C14 1.363(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.408(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.366(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.411(3) . ?
C16 H16 0.9500 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O2 C9 113.74(17) . . ?
C11 O3 C1 106.13(18) . . ?
C18 N1 C17 118.3(2) . . ?
O3 C1 C2 110.15(19) . . ?
O3 C1 C9 107.56(19) . . ?
C2 C1 C9 116.44(19) . . ?
O3 C1 Br1 108.42(14) . . ?
C2 C1 Br1 106.68(15) . . ?
C9 C1 Br1 107.32(15) . . ?
O1 C2 C3 124.8(2) . . ?
O1 C2 C1 120.5(2) . . ?
C3 C2 C1 114.7(2) . . ?
C4 C3 C8 118.8(2) . . ?
C4 C3 C2 119.7(2) . . ?
C8 C3 C2 121.4(2) . . ?
C5 C4 O2 117.8(2) . . ?
C5 C4 C3 121.2(2) . . ?
O2 C4 C3 120.8(2) . . ?
C4 C5 C6 118.8(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 120.1(2) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C3 120.1(2) . . ?
C7 C8 H8 119.9 . . ?
C3 C8 H8 119.9 . . ?
O2 C9 C10 108.59(18) . . ?
O2 C9 C1 111.48(18) . . ?
C10 C9 C1 100.25(19) . . ?
O2 C9 H9 112.0 . . ?
C10 C9 H9 112.0 . . ?
C1 C9 H9 112.0 . . ?
C11 C10 C18 118.9(2) . . ?
C11 C10 C9 108.6(2) . . ?
C18 C10 C9 132.5(2) . . ?
C10 C11 O3 113.8(2) . . ?
C10 C11 C12 122.5(2) . . ?
O3 C11 C12 123.7(2) . . ?
C11 C12 C13 125.5(2) . . ?
C11 C12 C17 113.9(2) . . ?
C13 C12 C17 120.5(2) . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
N1 C17 C16 118.2(2) . . ?
N1 C17 C12 123.9(2) . . ?
C16 C17 C12 117.8(2) . . ?
N1 C18 C10 122.5(2) . . ?
N1 C18 H18 118.8 . . ?
C10 C18 H18 118.8 . . ?

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
C11 O3 C1 C2 145.95(19) . . . . ?
C11 O3 C1 C9 18.1(2) . . . . ?
C11 O3 C1 Br1 -97.66(17) . . . . ?
O3 C1 C2 O1 48.7(3) . . . . ?
C9 C1 C2 O1 171.5(2) . . . . ?
Br1 C1 C2 O1 -68.7(3) . . . . ?
O3 C1 C2 C3 -131.1(2) . . . . ?
C9 C1 C2 C3 -8.3(3) . . . . ?
Br1 C1 C2 C3 111.47(19) . . . . ?
O1 C2 C3 C4 -157.4(2) . . . . ?
C1 C2 C3 C4 22.4(3) . . . . ?
O1 C2 C3 C8 19.6(4) . . . . ?
C1 C2 C3 C8 -160.6(2) . . . . ?
C9 O2 C4 C5 141.8(2) . . . . ?
C9 O2 C4 C3 -43.2(3) . . . . ?
C8 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C4 C5 177.5(2) . . . . ?
C8 C3 C4 O2 -174.4(2) . . . . ?
C2 C3 C4 O2 2.7(3) . . . . ?
O2 C4 C5 C6 175.6(2) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C5 C6 C7 -1.2(4) . . . . ?
C5 C6 C7 C8 0.7(4) . . . . ?
C6 C7 C8 C3 0.3(4) . . . . ?
C4 C3 C8 C7 -0.8(4) . . . . ?
C2 C3 C8 C7 -177.9(2) . . . . ?
C4 O2 C9 C10 163.47(19) . . . . ?
C4 O2 C9 C1 54.0(3) . . . . ?
O3 C1 C9 O2 95.9(2) . . . . ?
C2 C1 C9 O2 -28.2(3) . . . . ?
Br1 C1 C9 O2 -147.63(15) . . . . ?
O3 C1 C9 C10 -18.9(2) . . . . ?
C2 C1 C9 C10 -143.0(2) . . . . ?
Br1 C1 C9 C10 97.58(17) . . . . ?
O2 C9 C10 C11 -103.9(2) . . . . ?
C1 C9 C10 C11 13.0(2) . . . . ?
O2 C9 C10 C18 72.4(3) . . . . ?
C1 C9 C10 C18 -170.7(2) . . . . ?
C18 C10 C11 O3 -179.7(2) . . . . ?
C9 C10 C11 O3 -2.9(3) . . . . ?
C18 C10 C11 C12 0.4(3) . . . . ?
C9 C10 C11 C12 177.2(2) . . . . ?
C1 O3 C11 C10 -10.0(2) . . . . ?
C1 O3 C11 C12 169.9(2) . . . . ?
C10 C11 C12 C13 179.6(2) . . . . ?
O3 C11 C12 C13 -0.3(4) . . . . ?
C10 C11 C12 C17 0.3(3) . . . . ?
O3 C11 C12 C17 -179.6(2) . . . . ?
C11 C12 C13 C14 -177.4(2) . . . . ?
C17 C12 C13 C14 1.9(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C16 -1.7(4) . . . . ?
C14 C15 C16 C17 1.1(4) . . . . ?
C18 N1 C17 C16 -176.7(2) . . . . ?
C18 N1 C17 C12 1.6(3) . . . . ?
C15 C16 C17 N1 179.3(2) . . . . ?
C15 C16 C17 C12 0.9(3) . . . . ?
C11 C12 C17 N1 -1.4(3) . . . . ?
C13 C12 C17 N1 179.3(2) . . . . ?
C11 C12 C17 C16 177.0(2) . . . . ?
C13 C12 C17 C16 -2.4(3) . . . . ?
C17 N1 C18 C10 -0.8(3) . . . . ?
C11 C10 C18 N1 -0.1(4) . . . . ?
C9 C10 C18 N1 -176.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C9 H9 O1 1.00 2.66 3.281(3) 120.5 1_545 yes
C18 H18 O1 0.95 2.66 3.423(3) 137.9 1_545 yes
C18 H18 O3 0.95 2.58 3.426(3) 148.5 1_545 yes

_refine_diff_density_max         0.518
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.062

