# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_xxx
_database_code_depnum_ccdc_archive 'CCDC 1571573'
_audit_update_record             
;
2017-08-30 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Br Cl N3'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C14 H9 Br Cl N3'
_chemical_formula_iupac          ?
_chemical_formula_weight         334.59
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z

_cell_length_a                   7.656(2)
_cell_length_b                   9.850(3)
_cell_length_c                   18.330(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1382.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1857
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      25.4
_cell_special_details            
;
;

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.090
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    3.155
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.544
_exptl_absorpt_correction_T_max  0.764

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_reflns_number            9574
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0566
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         25.38
_reflns_number_total             2525
_reflns_number_gt                1999
_reflns_threshold_expression     >2sigma(I)
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'


#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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)+(0.0316P)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     SHELXL
_refine_ls_extinction_coef       0.0323(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.010(12)
_refine_ls_number_reflns         2525
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0768
_refine_ls_wR_factor_gt          0.0717
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.061

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br Uani 0.02868(6) 0.29403(5) 0.82097(2) 1.000 0.0625(2) . .
Cl1 Cl Uani 1.16926(19) 0.18316(15) 0.59170(8) 1.000 0.0900(6) . .
N1 N Uani 0.4208(4) 0.5642(3) 0.63665(18) 1.000 0.0392(11) . .
N2 N Uani 0.2951(5) 0.6515(3) 0.6135(2) 1.000 0.0507(12) . .
N3 N Uani 0.3356(5) 0.6869(4) 0.5467(2) 1.000 0.0560(12) . .
C1 C Uani 0.9840(6) 0.2846(4) 0.5881(2) 1.000 0.0533(14) . .
C2 C Uani 0.8323(7) 0.2414(4) 0.6199(3) 1.000 0.0617(19) . .
C3 C Uani 0.6870(6) 0.3250(4) 0.6194(2) 1.000 0.0540(16) . .
C4 C Uani 0.6945(5) 0.4530(4) 0.5875(2) 1.000 0.0377(12) . .
C5 C Uani 0.8494(6) 0.4935(4) 0.5554(2) 1.000 0.0437(14) . .
C6 C Uani 0.9949(6) 0.4102(4) 0.5547(2) 1.000 0.0527(17) . .
C7 C Uani 0.5419(6) 0.5427(3) 0.5841(2) 1.000 0.0417(12) . .
C8 C Uani 0.4853(6) 0.6226(4) 0.5274(2) 1.000 0.0523(16) . .
C9 C Uani 0.4072(5) 0.5076(4) 0.7089(2) 1.000 0.0370(12) . .
C10 C Uani 0.5452(6) 0.5139(4) 0.7569(2) 1.000 0.0480(14) . .
C11 C Uani 0.5277(6) 0.4524(4) 0.8252(2) 1.000 0.0530(12) . .
C12 C Uani 0.3760(6) 0.3895(4) 0.8448(2) 1.000 0.0493(14) . .
C13 C Uani 0.2383(6) 0.3858(4) 0.7958(2) 1.000 0.0423(12) . .
C14 C Uani 0.2511(5) 0.4461(4) 0.7275(2) 1.000 0.0403(12) . .
H2 H Uiso 0.82680 0.15630 0.64170 1.000 0.0740 calc R
H3 H Uiso 0.58340 0.29530 0.64060 1.000 0.0650 calc R
H5 H Uiso 0.85600 0.57880 0.53380 1.000 0.0520 calc R
H6 H Uiso 1.09780 0.43810 0.53230 1.000 0.0630 calc R
H8 H Uiso 0.54110 0.63130 0.48260 1.000 0.0630 calc R
H10 H Uiso 0.64800 0.55820 0.74410 1.000 0.0580 calc R
H11 H Uiso 0.62080 0.45430 0.85780 1.000 0.0630 calc R
H12 H Uiso 0.36510 0.34950 0.89050 1.000 0.0590 calc R
H14 H Uiso 0.15740 0.44510 0.69520 1.000 0.0480 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C13 1.899(4) . . yes
Cl1 C1 1.736(5) . . yes
N1 N2 1.359(5) . . yes
N1 C7 1.354(5) . . yes
N1 C9 1.441(5) . . yes
N2 N3 1.310(5) . . yes
N3 C8 1.356(6) . . yes
C1 C2 1.367(7) . . no
C1 C6 1.383(6) . . no
C2 C3 1.384(7) . . no
C3 C4 1.391(6) . . no
C4 C5 1.383(6) . . no
C4 C7 1.466(6) . . no
C5 C6 1.384(6) . . no
C7 C8 1.374(5) . . no
C9 C10 1.376(6) . . no
C9 C14 1.383(5) . . no
C10 C11 1.397(5) . . no
C11 C12 1.365(6) . . no
C12 C13 1.385(6) . . no
C13 C14 1.389(5) . . no
C2 H2 0.9300 . . no
C3 H3 0.9300 . . no
C5 H5 0.9300 . . no
C6 H6 0.9300 . . no
C8 H8 0.9300 . . no
C10 H10 0.9300 . . no
C11 H11 0.9300 . . no
C12 H12 0.9300 . . no
C14 H14 0.9300 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C7 111.2(3) . . . yes
N2 N1 C9 118.7(3) . . . yes
C7 N1 C9 130.0(3) . . . yes
N1 N2 N3 107.0(3) . . . yes
N2 N3 C8 108.6(3) . . . yes
Cl1 C1 C2 119.9(3) . . . yes
Cl1 C1 C6 118.8(3) . . . yes
C2 C1 C6 121.2(4) . . . no
C1 C2 C3 119.7(4) . . . no
C2 C3 C4 120.6(4) . . . no
C3 C4 C5 118.4(4) . . . no
C3 C4 C7 122.1(4) . . . no
C5 C4 C7 119.4(3) . . . no
C4 C5 C6 121.6(4) . . . no
C1 C6 C5 118.6(4) . . . no
N1 C7 C4 127.6(3) . . . yes
N1 C7 C8 103.5(3) . . . yes
C4 C7 C8 129.0(4) . . . no
N3 C8 C7 109.7(4) . . . yes
N1 C9 C10 121.0(3) . . . yes
N1 C9 C14 117.3(3) . . . yes
C10 C9 C14 121.7(4) . . . no
C9 C10 C11 118.7(4) . . . no
C10 C11 C12 121.0(4) . . . no
C11 C12 C13 119.3(4) . . . no
Br1 C13 C12 119.9(3) . . . yes
Br1 C13 C14 118.8(3) . . . yes
C12 C13 C14 121.3(4) . . . no
C9 C14 C13 118.1(4) . . . no
C1 C2 H2 120.00 . . . no
C3 C2 H2 120.00 . . . no
C2 C3 H3 120.00 . . . no
C4 C3 H3 120.00 . . . no
C4 C5 H5 119.00 . . . no
C6 C5 H5 119.00 . . . no
C1 C6 H6 121.00 . . . no
C5 C6 H6 121.00 . . . no
N3 C8 H8 125.00 . . . no
C7 C8 H8 125.00 . . . no
C9 C10 H10 121.00 . . . no
C11 C10 H10 121.00 . . . no
C10 C11 H11 120.00 . . . no
C12 C11 H11 119.00 . . . no
C11 C12 H12 120.00 . . . no
C13 C12 H12 120.00 . . . no
C9 C14 H14 121.00 . . . no
C13 C14 H14 121.00 . . . no

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
C7 N1 N2 N3 -0.5(4) . . . . no
C9 N1 N2 N3 -179.3(3) . . . . no
N2 N1 C7 C4 -178.4(4) . . . . no
C9 N1 C7 C4 0.3(6) . . . . no
N2 N1 C7 C8 0.6(4) . . . . no
C9 N1 C7 C8 179.2(4) . . . . no
N2 N1 C9 C10 -128.5(4) . . . . no
C7 N1 C9 C10 53.0(6) . . . . no
N2 N1 C9 C14 52.1(5) . . . . no
C7 N1 C9 C14 -126.4(4) . . . . no
N1 N2 N3 C8 0.2(4) . . . . no
N2 N3 C8 C7 0.2(5) . . . . no
Cl1 C1 C6 C5 -176.6(3) . . . . no
C2 C1 C6 C5 1.4(6) . . . . no
C6 C1 C2 C3 -0.6(7) . . . . no
Cl1 C1 C2 C3 177.4(3) . . . . no
C1 C2 C3 C4 -0.7(7) . . . . no
C2 C3 C4 C7 178.2(4) . . . . no
C2 C3 C4 C5 1.0(6) . . . . no
C5 C4 C7 N1 -142.2(4) . . . . no
C3 C4 C7 C8 -138.1(4) . . . . no
C5 C4 C7 C8 39.1(6) . . . . no
C3 C4 C5 C6 -0.2(6) . . . . no
C7 C4 C5 C6 -177.5(4) . . . . no
C3 C4 C7 N1 40.6(6) . . . . no
C4 C5 C6 C1 -1.0(6) . . . . no
C4 C7 C8 N3 178.4(4) . . . . no
N1 C7 C8 N3 -0.5(4) . . . . no
N1 C9 C10 C11 -177.3(3) . . . . no
C14 C9 C10 C11 2.1(6) . . . . no
N1 C9 C14 C13 177.3(3) . . . . no
C10 C9 C14 C13 -2.2(6) . . . . no
C9 C10 C11 C12 -1.3(6) . . . . no
C10 C11 C12 C13 0.6(6) . . . . no
C11 C12 C13 Br1 178.1(3) . . . . no
C11 C12 C13 C14 -0.7(6) . . . . no
Br1 C13 C14 C9 -177.4(3) . . . . no
C12 C13 C14 C9 1.5(6) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Br1 N2 3.092(4) . 4_546 no
Br1 H8 3.1000 . 2_565 no
Cl1 C14 3.647(4) . 1_655 no
Cl1 C4 3.553(4) . 3_556 no
Cl1 C5 3.493(4) . 3_556 no
Cl1 C11 3.587(5) . 4_746 no
Cl1 H11 2.9200 . 4_746 no
N2 C11 3.448(5) . 4_656 no
N2 Br1 3.092(4) . 4_556 no
N1 H3 2.9300 . . no
N2 H14 2.7400 . . no
N3 H5 2.7400 . 3_466 no
N3 H8 2.9300 . 3_466 no
C3 C9 3.243(6) . . no
C3 C10 3.316(6) . . no
C4 C10 3.363(5) . . no
C4 Cl1 3.553(4) . 3_456 no
C5 Cl1 3.493(4) . 3_456 no
C9 C3 3.243(6) . . no
C10 C4 3.363(5) . . no
C10 C3 3.316(6) . . no
C11 N2 3.448(5) . 4_646 no
C11 Cl1 3.587(5) . 4_756 no
C14 Cl1 3.647(4) . 1_455 no
C1 H14 2.8500 . 1_655 no
C4 H10 3.0700 . . no
C5 H8 3.0300 . . no
C6 H14 2.8800 . 1_655 no
C7 H10 3.0500 . . no
C8 H5 2.8700 . . no
C8 H12 2.9300 . 4_656 no
C9 H3 2.7900 . . no
C10 H3 3.0400 . . no
C12 H2 3.0600 . 4_656 no
C13 H2 2.9400 . 4_656 no
H2 C12 3.0600 . 4_646 no
H2 C13 2.9400 . 4_646 no
H3 N1 2.9300 . . no
H3 C9 2.7900 . . no
H3 C10 3.0400 . . no
H5 C8 2.8700 . . no
H5 N3 2.7400 . 3_566 no
H8 C5 3.0300 . . no
H8 Br1 3.1000 . 2_564 no
H8 N3 2.9300 . 3_566 no
H10 C4 3.0700 . . no
H10 C7 3.0500 . . no
H11 Cl1 2.9200 . 4_756 no
H12 C8 2.9300 . 4_646 no
H14 N2 2.7400 . . no
H14 C1 2.8500 . 1_455 no
H14 C6 2.8800 . 1_455 no

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
