# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_02882JorgeHumbrias
_database_code_depnum_ccdc_archive 'CCDC 1952333'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles'
;Servicio Interdepartamental de Investigacion (SIdI), Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2019-09-09 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            VL_785-1
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 Br Cl N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         388.68
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.0480(2)
_cell_length_b                   12.9076(3)
_cell_length_c                   18.7303(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1703.95(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9803
_cell_measurement_theta_min      2.6871
_cell_measurement_theta_max      23.0027
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.429
_exptl_crystal_size_mid          0.355
_exptl_crystal_size_min          0.219
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792

_exptl_absorpt_coefficient_mu    2.580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_T_max  0.60

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            56068
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             3131
_reflns_number_gt                2946
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0858
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_restrained_S_all      1.192
_refine_ls_number_reflns         3131
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+0.5981P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.220
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1154 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(2)

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'
Cl Cl 0.1484 0.1585 '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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.45685(8) 0.44691(4) 0.70546(2) 0.05026(17) Uani d . . . 1 . .
C C1 0.4494(9) 0.2521(3) 0.4466(3) 0.0477(11) Uani d . . . 1 . .
C C2 0.3411(10) 0.2662(4) 0.3328(3) 0.0665(17) Uani d . . . 1 . .
H H2A 0.2042 0.2602 0.3297 0.08 Uiso calc U . R 1 . .
H H2B 0.3954 0.2492 0.2866 0.08 Uiso calc U . R 1 . .
C C3 0.3983(7) 0.3749(4) 0.3555(2) 0.0407(10) Uani d . . . 1 . .
H H3 0.2926 0.4227 0.3473 0.049 Uiso calc U . R 1 . .
C C4 0.5785(6) 0.4166(3) 0.3186(2) 0.0373(10) Uani d . . . 1 . .
C C5 0.7478(9) 0.3477(5) 0.3294(4) 0.0701(17) Uani d . . . 1 . .
H H5A 0.7724 0.3403 0.3796 0.105 Uiso calc U . R 1 . .
H H5B 0.8564 0.3778 0.3065 0.105 Uiso calc U . R 1 . .
H H5C 0.7227 0.2808 0.309 0.105 Uiso calc U . R 1 . .
C C6 0.5369(9) 0.4285(5) 0.2391(3) 0.0616(14) Uani d . . . 1 . .
H H6A 0.6415 0.4628 0.2163 0.092 Uiso calc U . R 1 . .
H H6B 0.4238 0.4689 0.2329 0.092 Uiso calc U . R 1 . .
H H6C 0.5194 0.3613 0.2182 0.092 Uiso calc U . R 1 . .
C C7 0.6249(10) 0.5244(4) 0.3482(3) 0.0676(17) Uani d . . . 1 . .
H H7A 0.6631 0.5185 0.3972 0.101 Uiso calc U . R 1 . .
H H7B 0.5144 0.5677 0.345 0.101 Uiso calc U . R 1 . .
H H7C 0.726 0.5545 0.3209 0.101 Uiso calc U . R 1 . .
C C8 0.3786(7) 0.4325(3) 0.4829(2) 0.0393(10) Uani d . . . 1 . .
C C9 0.4202(8) 0.4053(3) 0.5600(2) 0.0457(12) Uani d . . . 1 . .
H H9A 0.3223 0.3592 0.5777 0.055 Uiso calc U . R 1 . .
H H9B 0.5406 0.3692 0.5627 0.055 Uiso calc U . R 1 . .
C C10 0.4278(7) 0.5007(4) 0.6061(2) 0.0415(11) Uani d . . . 1 . .
H H10 0.3065 0.5374 0.6024 0.05 Uiso calc U . R 1 . .
C C11 0.5854(6) 0.5751(3) 0.5908(2) 0.0369(10) Uani d . . . 1 . .
C C12 0.7525(8) 0.5463(4) 0.5566(3) 0.0489(11) Uani d . . . 1 . .
H H12 0.7695 0.4773 0.5438 0.059 Uiso calc U . R 1 . .
C C13 0.8943(8) 0.6169(5) 0.5411(3) 0.0611(15) Uani d . . . 1 . .
H H13 1.005 0.5955 0.5185 0.073 Uiso calc U . R 1 . .
C C14 0.8693(9) 0.7198(5) 0.5596(3) 0.0600(14) Uani d . . . 1 . .
H H14 0.9627 0.7683 0.5489 0.072 Uiso calc U . R 1 . .
C C15 0.7083(9) 0.7496(4) 0.5934(3) 0.0544(14) Uani d . . . 1 . .
H H15 0.6915 0.8188 0.6058 0.065 Uiso calc U . R 1 . .
C C16 0.5705(7) 0.6788(3) 0.6092(2) 0.0434(11) Uani d . . . 1 . .
Cl Cl1 0.3676(3) 0.72412(11) 0.65196(10) 0.0750(5) Uani d . . . 1 . .
N N1 0.4227(5) 0.3583(3) 0.43263(18) 0.0356(8) Uani d . . . 1 . .
O O1 0.4141(7) 0.1992(3) 0.3868(2) 0.0692(12) Uani d . . . 1 . .
O O2 0.4970(7) 0.2116(3) 0.5007(2) 0.0640(12) Uani d . . . 1 . .
O O3 0.3163(6) 0.5149(3) 0.46474(18) 0.0530(9) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C10 . 1.996(4) ?
C1 O2 . 1.188(6) ?
C1 O1 . 1.335(6) ?
C1 N1 . 1.408(6) ?
C2 O1 . 1.426(7) ?
C2 C3 . 1.521(7) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C3 N1 . 1.470(5) ?
C3 C4 . 1.543(6) ?
C3 H3 . 0.98 ?
C4 C5 . 1.502(7) ?
C4 C6 . 1.526(7) ?
C4 C7 . 1.532(7) ?
C5 H5A . 0.96 ?
C5 H5B . 0.96 ?
C5 H5C . 0.96 ?
C6 H6A . 0.96 ?
C6 H6B . 0.96 ?
C6 H6C . 0.96 ?
C7 H7A . 0.96 ?
C7 H7B . 0.96 ?
C7 H7C . 0.96 ?
C8 O3 . 1.200(5) ?
C8 N1 . 1.378(6) ?
C8 C9 . 1.515(6) ?
C9 C10 . 1.505(6) ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C10 C11 . 1.496(6) ?
C10 H10 . 0.98 ?
C11 C16 . 1.387(6) ?
C11 C12 . 1.391(7) ?
C12 C13 . 1.384(8) ?
C12 H12 . 0.93 ?
C13 C14 . 1.383(9) ?
C13 H13 . 0.93 ?
C14 C15 . 1.355(9) ?
C14 H14 . 0.93 ?
C15 C16 . 1.366(7) ?
C15 H15 . 0.93 ?
C16 Cl1 . 1.740(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 C1 O1 . . 122.8(4) ?
O2 C1 N1 . . 128.7(5) ?
O1 C1 N1 . . 108.5(4) ?
O1 C2 C3 . . 105.3(4) ?
O1 C2 H2A . . 110.7 ?
C3 C2 H2A . . 110.7 ?
O1 C2 H2B . . 110.7 ?
C3 C2 H2B . . 110.7 ?
H2A C2 H2B . . 108.8 ?
N1 C3 C2 . . 99.9(4) ?
N1 C3 C4 . . 113.2(4) ?
C2 C3 C4 . . 114.5(4) ?
N1 C3 H3 . . 109.6 ?
C2 C3 H3 . . 109.6 ?
C4 C3 H3 . . 109.6 ?
C5 C4 C6 . . 110.1(4) ?
C5 C4 C7 . . 108.7(5) ?
C6 C4 C7 . . 107.6(4) ?
C5 C4 C3 . . 112.7(4) ?
C6 C4 C3 . . 108.3(4) ?
C7 C4 C3 . . 109.3(4) ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C4 C6 H6A . . 109.5 ?
C4 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C4 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C4 C7 H7A . . 109.5 ?
C4 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C4 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O3 C8 N1 . . 120.4(4) ?
O3 C8 C9 . . 123.1(4) ?
N1 C8 C9 . . 116.5(4) ?
C10 C9 C8 . . 111.4(4) ?
C10 C9 H9A . . 109.3 ?
C8 C9 H9A . . 109.3 ?
C10 C9 H9B . . 109.3 ?
C8 C9 H9B . . 109.3 ?
H9A C9 H9B . . 108.0 ?
C11 C10 C9 . . 116.2(4) ?
C11 C10 Br1 . . 109.0(3) ?
C9 C10 Br1 . . 104.8(3) ?
C11 C10 H10 . . 108.9 ?
C9 C10 H10 . . 108.9 ?
Br1 C10 H10 . . 108.9 ?
C16 C11 C12 . . 115.8(4) ?
C16 C11 C10 . . 121.1(4) ?
C12 C11 C10 . . 123.0(4) ?
C13 C12 C11 . . 122.2(5) ?
C13 C12 H12 . . 118.9 ?
C11 C12 H12 . . 118.9 ?
C14 C13 C12 . . 119.2(5) ?
C14 C13 H13 . . 120.4 ?
C12 C13 H13 . . 120.4 ?
C15 C14 C13 . . 119.8(5) ?
C15 C14 H14 . . 120.1 ?
C13 C14 H14 . . 120.1 ?
C14 C15 C16 . . 120.4(5) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
C15 C16 C11 . . 122.6(5) ?
C15 C16 Cl1 . . 117.3(4) ?
C11 C16 Cl1 . . 120.0(4) ?
C8 N1 C1 . . 125.4(4) ?
C8 N1 C3 . . 122.9(4) ?
C1 N1 C3 . . 109.9(4) ?
C1 O1 C2 . . 110.6(4) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C2 C3 N1 . . . . -23.3(6) ?
O1 C2 C3 C4 . . . . 98.0(5) ?
N1 C3 C4 C5 . . . . 56.9(6) ?
C2 C3 C4 C5 . . . . -56.8(6) ?
N1 C3 C4 C6 . . . . 178.9(4) ?
C2 C3 C4 C6 . . . . 65.2(5) ?
N1 C3 C4 C7 . . . . -64.1(5) ?
C2 C3 C4 C7 . . . . -177.8(5) ?
O3 C8 C9 C10 . . . . -16.3(7) ?
N1 C8 C9 C10 . . . . 161.4(4) ?
C8 C9 C10 C11 . . . . -65.3(6) ?
C8 C9 C10 Br1 . . . . 174.4(3) ?
C9 C10 C11 C16 . . . . 155.9(4) ?
Br1 C10 C11 C16 . . . . -86.0(5) ?
C9 C10 C11 C12 . . . . -22.9(6) ?
Br1 C10 C11 C12 . . . . 95.2(5) ?
C16 C11 C12 C13 . . . . -0.8(7) ?
C10 C11 C12 C13 . . . . 178.1(4) ?
C11 C12 C13 C14 . . . . -0.4(8) ?
C12 C13 C14 C15 . . . . 0.8(8) ?
C13 C14 C15 C16 . . . . 0.0(8) ?
C14 C15 C16 C11 . . . . -1.3(8) ?
C14 C15 C16 Cl1 . . . . -179.5(4) ?
C12 C11 C16 C15 . . . . 1.6(7) ?
C10 C11 C16 C15 . . . . -177.2(4) ?
C12 C11 C16 Cl1 . . . . 179.8(4) ?
C10 C11 C16 Cl1 . . . . 0.9(6) ?
O3 C8 N1 C1 . . . . -162.8(5) ?
C9 C8 N1 C1 . . . . 19.5(7) ?
O3 C8 N1 C3 . . . . 0.4(7) ?
C9 C8 N1 C3 . . . . -177.3(4) ?
O2 C1 N1 C8 . . . . -25.4(9) ?
O1 C1 N1 C8 . . . . 155.4(5) ?
O2 C1 N1 C3 . . . . 169.5(6) ?
O1 C1 N1 C3 . . . . -9.7(6) ?
C2 C3 N1 C8 . . . . -145.2(5) ?
C4 C3 N1 C8 . . . . 92.5(5) ?
C2 C3 N1 C1 . . . . 20.3(6) ?
C4 C3 N1 C1 . . . . -102.0(5) ?
O2 C1 O1 C2 . . . . 174.0(6) ?
N1 C1 O1 C2 . . . . -6.8(6) ?
C3 C2 O1 C1 . . . . 19.7(7) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C15 H15 O3 4_566 0.93 2.67 3.316(6) 127.2 ?

