# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_ISB5_Compound_I
_database_code_depnum_ccdc_archive 'CCDC 1401865'
_audit_update_record             
;
2015-05-19 deposited with the CCDC.
2015-10-16 downloaded from the CCDC.
;


_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
(E)-N'-(2-(allyloxy)benzylidene)-2-(4-bromophenyl)acetohydrazide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 Br N2 O2'
_chemical_formula_sum            'C18 H17 Br N2 O2'
_chemical_formula_weight         373.24

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.6957(3)
_cell_length_b                   4.84494(11)
_cell_length_c                   23.1542(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.219(2)
_cell_angle_gamma                90
_cell_volume                     1611.23(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4653
_cell_measurement_theta_min      6.0030
_cell_measurement_theta_max      76.3900

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.571
_shelx_estimated_absorpt_T_min   0.535
_shelx_estimated_absorpt_T_max   0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro, Agilent (2013)'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1725
_diffrn_standards_number         0
_diffrn_reflns_number            7820
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.277
_diffrn_reflns_theta_max         76.730
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3335
_reflns_number_gt                2903
_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       'CrysAlisPro, Agilent (2013)'
_computing_cell_refinement       'CrysAlisPro, Agilent (2013)'
_computing_data_reduction        'CrysAlisPro, Agilent (2013)'
_computing_structure_solution    
;
SHELXS (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2015) & TITAN (Hunter & Simpson, 1999)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  
;
SHELXL-2014 (Sheldrick, 2008), enCIFer (Allen et al., 2004), 
PLATON (Spek, 2009),  PublCIF (Westrip 2010), WINGX (Farrugia 1997)
;


_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)+(0.0967P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3335
_refine_ls_number_parameters     211
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1408
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_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_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
O2 O 0.55825(13) -0.1399(5) 0.31960(9) 0.0199(4) Uani 1 1 d . . . . .
C23 C 0.7144(2) 0.1941(7) 0.34141(14) 0.0250(6) Uani 1 1 d . . . . .
H231 H 0.6682 0.2208 0.3640 0.030 Uiso 1 1 calc R U . . .
H232 H 0.7699 0.3006 0.3496 0.030 Uiso 1 1 calc R U . . .
C22 C 0.7014(2) 0.0093(7) 0.29872(14) 0.0235(6) Uani 1 1 d . . . . .
H22 H 0.7498 -0.0089 0.2775 0.028 Uiso 1 1 calc R U . . .
C21 C 0.6188(2) -0.1746(6) 0.28012(13) 0.0213(6) Uani 1 1 d . . . . .
H211 H 0.5859 -0.1274 0.2394 0.026 Uiso 1 1 calc R U . . .
H212 H 0.6392 -0.3694 0.2804 0.026 Uiso 1 1 calc R U . . .
C2 C 0.47949(19) -0.2988(5) 0.31055(13) 0.0156(5) Uani 1 1 d . . . . .
C3 C 0.45718(19) -0.4979(6) 0.26647(13) 0.0195(5) Uani 1 1 d . . . . .
H2 H 0.4978 -0.5310 0.2403 0.023 Uiso 1 1 calc R U . . .
C4 C 0.3752(2) -0.6480(6) 0.26087(13) 0.0201(6) Uani 1 1 d . . . . .
H3 H 0.3602 -0.7841 0.2308 0.024 Uiso 1 1 calc R U . . .
C5 C 0.31496(18) -0.6009(6) 0.29891(12) 0.0181(5) Uani 1 1 d . . . . .
H4 H 0.2592 -0.7050 0.2951 0.022 Uiso 1 1 calc R U . . .
C6 C 0.33736(18) -0.4000(6) 0.34239(12) 0.0158(5) Uani 1 1 d . . . . .
H5 H 0.2962 -0.3671 0.3683 0.019 Uiso 1 1 calc R U . . .
C1 C 0.4186(2) -0.2462(5) 0.34882(12) 0.0146(5) Uani 1 1 d . . . . .
C7 C 0.44286(17) -0.0300(6) 0.39368(11) 0.0151(5) Uani 1 1 d . . . . .
H7 H 0.4981 0.0747 0.3956 0.018 Uiso 1 1 calc R U . . .
N1 N 0.39065(15) 0.0197(5) 0.43028(10) 0.0152(4) Uani 1 1 d . U . . .
N2 N 0.42176(17) 0.2341(5) 0.46838(11) 0.0152(5) Uani 1 1 d D U . . .
H2N H 0.4685(19) 0.308(8) 0.4665(19) 0.018 Uiso 1 1 d D U . . .
C8 C 0.37453(18) 0.3221(6) 0.50888(12) 0.0137(5) Uani 1 1 d . U . . .
O1 O 0.40437(13) 0.5189(4) 0.54152(9) 0.0189(4) Uani 1 1 d . . . . .
C9 C 0.28501(19) 0.1755(6) 0.51272(13) 0.0172(5) Uani 1 1 d . . . . .
H9A H 0.2862 -0.0150 0.4975 0.021 Uiso 1 1 calc R U . . .
H9B H 0.2795 0.1645 0.5545 0.021 Uiso 1 1 calc R U . . .
C11 C 0.20195(18) 0.3278(6) 0.47720(12) 0.0146(5) Uani 1 1 d . U . . .
C12 C 0.1669(2) 0.2676(6) 0.41739(14) 0.0196(6) Uani 1 1 d . . . . .
H12 H 0.1967 0.1312 0.3984 0.024 Uiso 1 1 calc R U . . .
C13 C 0.08940(19) 0.4045(7) 0.38547(13) 0.0220(6) Uani 1 1 d . . . . .
H13 H 0.0660 0.3625 0.3450 0.026 Uiso 1 1 calc R U . . .
C14 C 0.04664(18) 0.6039(6) 0.41369(13) 0.0188(5) Uani 1 1 d . U . . .
Br14 Br -0.06394(2) 0.78087(7) 0.37217(2) 0.02643(16) Uani 1 1 d . U . . .
C15 C 0.0804(2) 0.6729(7) 0.47215(14) 0.0207(6) Uani 1 1 d . . . . .
H15 H 0.0513 0.8126 0.4906 0.025 Uiso 1 1 calc R U . . .
C16 C 0.15831(19) 0.5330(6) 0.50341(12) 0.0192(5) Uani 1 1 d . . . . .
H16 H 0.1822 0.5790 0.5436 0.023 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
O2 C2 1.369(4) . y
O2 C21 1.414(4) . y
C23 C22 1.317(5) . y
C23 H231 0.9500 . ?
C23 H232 0.9500 . ?
C22 C21 1.494(4) . y
C22 H22 0.9500 . ?
C21 H211 0.9900 . ?
C21 H212 0.9900 . ?
C2 C3 1.392(4) . ?
C2 C1 1.410(4) . ?
C3 C4 1.389(4) . ?
C3 H2 0.9500 . ?
C4 C5 1.394(5) . ?
C4 H3 0.9500 . ?
C5 C6 1.389(4) . ?
C5 H4 0.9500 . ?
C6 C1 1.388(4) . ?
C6 H5 0.9500 . ?
C1 C7 1.465(4) . y
C7 N1 1.281(4) . y
C7 H7 0.9500 . ?
N1 N2 1.377(3) . y
N2 C8 1.348(4) . y
N2 H2N 0.783(19) . ?
C8 O1 1.238(3) . y
C8 C9 1.514(4) . ?
C9 C11 1.512(4) . y
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 C16 1.390(4) . ?
C11 C12 1.402(4) . ?
C12 C13 1.389(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(4) . ?
C14 Br14 1.908(3) . y
C15 C16 1.394(4) . ?
C15 H15 0.9500 . ?
C16 H16 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
C2 O2 C21 117.5(2) . . ?
C22 C23 H231 120.0 . . ?
C22 C23 H232 120.0 . . ?
H231 C23 H232 120.0 . . ?
C23 C22 C21 126.9(3) . . y
C23 C22 H22 116.5 . . ?
C21 C22 H22 116.5 . . ?
O2 C21 C22 109.1(2) . . y
O2 C21 H211 109.9 . . ?
C22 C21 H211 109.9 . . ?
O2 C21 H212 109.9 . . ?
C22 C21 H212 109.9 . . ?
H211 C21 H212 108.3 . . ?
O2 C2 C3 124.2(3) . . ?
O2 C2 C1 115.5(2) . . ?
C3 C2 C1 120.2(3) . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H2 120.1 . . ?
C2 C3 H2 120.1 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H3 119.7 . . ?
C5 C4 H3 119.7 . . ?
C6 C5 C4 119.2(2) . . ?
C6 C5 H4 120.4 . . ?
C4 C5 H4 120.4 . . ?
C1 C6 C5 121.4(3) . . ?
C1 C6 H5 119.3 . . ?
C5 C6 H5 119.3 . . ?
C6 C1 C2 118.8(3) . . ?
C6 C1 C7 122.3(3) . . ?
C2 C1 C7 118.9(2) . . ?
N1 C7 C1 120.9(2) . . y
N1 C7 H7 119.6 . . ?
C1 C7 H7 119.6 . . ?
C7 N1 N2 113.7(2) . . y
C8 N2 N1 122.3(2) . . y
C8 N2 H2N 119(3) . . ?
N1 N2 H2N 119(3) . . ?
O1 C8 N2 120.0(2) . . ?
O1 C8 C9 121.7(2) . . y
N2 C8 C9 118.3(2) . . y
C11 C9 C8 110.5(2) . . ?
C11 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C11 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C16 C11 C12 118.2(3) . . ?
C16 C11 C9 120.4(2) . . ?
C12 C11 C9 121.4(3) . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 118.9(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 121.7(3) . . ?
C15 C14 Br14 118.5(2) . . ?
C13 C14 Br14 119.8(2) . . ?
C14 C15 C16 118.5(3) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C11 C16 C15 121.7(3) . . ?
C11 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?

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
C2 O2 C21 C22 -178.1(2) . . . . ?
C23 C22 C21 O2 -5.6(4) . . . . ?
C21 O2 C2 C3 2.4(4) . . . . ?
C21 O2 C2 C1 -176.5(2) . . . . ?
O2 C2 C3 C4 -179.8(3) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C5 C6 C1 C2 -0.6(4) . . . . ?
C5 C6 C1 C7 178.9(2) . . . . ?
O2 C2 C1 C6 -179.8(2) . . . . ?
C3 C2 C1 C6 1.2(4) . . . . ?
O2 C2 C1 C7 0.6(4) . . . . ?
C3 C2 C1 C7 -178.3(2) . . . . ?
C6 C1 C7 N1 2.2(4) . . . . ?
C2 C1 C7 N1 -178.3(3) . . . . ?
C1 C7 N1 N2 -178.2(2) . . . . ?
C7 N1 N2 C8 178.0(2) . . . . ?
N1 N2 C8 O1 -178.7(2) . . . . ?
N1 N2 C8 C9 0.9(4) . . . . ?
O1 C8 C9 C11 83.7(3) . . . . ?
N2 C8 C9 C11 -95.9(3) . . . . ?
C8 C9 C11 C16 -90.0(3) . . . . ?
C8 C9 C11 C12 89.9(3) . . . . ?
C16 C11 C12 C13 -1.5(4) . . . . ?
C9 C11 C12 C13 178.6(3) . . . . ?
C11 C12 C13 C14 0.1(5) . . . . ?
C12 C13 C14 C15 1.4(4) . . . . ?
C12 C13 C14 Br14 -176.6(2) . . . . ?
C13 C14 C15 C16 -1.4(4) . . . . ?
Br14 C14 C15 C16 176.6(2) . . . . ?
C12 C11 C16 C15 1.5(4) . . . . ?
C9 C11 C16 C15 -178.6(3) . . . . ?
C14 C15 C16 C11 -0.1(4) . . . . ?

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
N2 H2N O1 0.783(19) 2.09(2) 2.874(3) 176(4) 3_666
C7 H7 O1 0.95 2.68 3.464(3) 140.6 3_666

_refine_diff_density_max         1.164
_refine_diff_density_min         -1.149
_refine_diff_density_rms         0.125

####################################################################### 
# 
# 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_isb13_Compound_II
_database_code_depnum_ccdc_archive 'CCDC 1401866'
_audit_update_record             
;
2015-05-19 deposited with the CCDC.
2015-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
E)-N'-(biphenyl-4-ylmethylene)-2-(4-bromophenyl)acetohydrazide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 Br N2 O'
_chemical_formula_sum            'C21 H17 Br N2 O'
_chemical_formula_weight         393.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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, z+1/2'

_cell_length_a                   20.4423(11)
_cell_length_b                   5.5758(3)
_cell_length_c                   7.6350(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.621(7)
_cell_angle_gamma                90
_cell_volume                     860.43(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4457
_cell_measurement_theta_min      6.5320
_cell_measurement_theta_max      75.6700

_exptl_crystal_description       'triangular block'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    3.335
_shelx_estimated_absorpt_T_min   0.555
_shelx_estimated_absorpt_T_max   0.825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro, Agilent (2013)'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1725
_diffrn_standards_number         0
_diffrn_reflns_number            7517
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.375
_diffrn_reflns_theta_max         76.127
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_point_group_measured_fraction_full 0.872
_reflns_number_total             3007
_reflns_number_gt                2814
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_max     0.727
_reflns_Friedel_fraction_full    0.763

_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       'CrysAlisPro, Agilent (2013)'
_computing_cell_refinement       'CrysAlisPro, Agilent (2013)'
_computing_data_reduction        'CrysAlisPro, Agilent (2013)'
_computing_structure_solution    
;
SHELXS (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2015b) & TITAN (Hunter & Simpson, 1999)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  
;
SHELXL-2014 (Sheldrick, 2008), enCIFer (Allen et al., 2004), 
PLATON (Spek, 2009),  PublCIF (Westrip 2010), WINGX (Farrugia 1997)
;

_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)+(0.1359P)²+6.9116P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1109 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3007
_refine_ls_number_parameters     229
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0858
_refine_ls_wR_factor_ref         0.2495
_refine_ls_wR_factor_gt          0.2443
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.133
_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_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
C1' C 0.1760(9) 0.759(2) 0.498(2) 0.026(3) Uani 1 1 d . . . . .
C2' C 0.1511(7) 0.566(2) 0.588(2) 0.030(3) Uani 1 1 d . . . . .
H2' H 0.1798 0.4386 0.6318 0.036 Uiso 1 1 calc R U . . .
C3' C 0.0856(7) 0.559(2) 0.613(2) 0.032(3) Uani 1 1 d . . . . .
H3' H 0.0700 0.4276 0.6735 0.038 Uiso 1 1 calc R U . . .
C4' C 0.0423(7) 0.743(2) 0.550(2) 0.023(3) Uani 1 1 d . . . . .
H4' H -0.0030 0.7367 0.5649 0.028 Uiso 1 1 calc R U . . .
C5' C 0.0673(8) 0.940(2) 0.462(2) 0.030(3) Uani 1 1 d . . . . .
H5' H 0.0390 1.0698 0.4205 0.035 Uiso 1 1 calc R U . . .
C6' C 0.1321(7) 0.943(2) 0.438(2) 0.028(3) Uani 1 1 d . . . . .
H6' H 0.1478 1.0751 0.3778 0.034 Uiso 1 1 calc R U . . .
C1 C 0.2463(7) 0.760(2) 0.4701(19) 0.021(3) Uani 1 1 d . . . . .
C2 C 0.2736(7) 0.945(2) 0.375(2) 0.029(3) Uani 1 1 d . . . . .
H2 H 0.2464 1.0760 0.3302 0.035 Uiso 1 1 calc R U . . .
C3 C 0.3379(6) 0.939(2) 0.347(2) 0.026(3) Uani 1 1 d . . . . .
H3 H 0.3548 1.0728 0.2913 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3798(7) 0.746(2) 0.3972(19) 0.023(3) Uani 1 1 d . . . . .
C5 C 0.3530(7) 0.563(2) 0.494(2) 0.032(3) Uani 1 1 d . . . . .
H5 H 0.3806 0.4337 0.5387 0.039 Uiso 1 1 calc R U . . .
C6 C 0.2900(7) 0.566(2) 0.524(2) 0.026(3) Uani 1 1 d . . . . .
H6 H 0.2740 0.4345 0.5845 0.031 Uiso 1 1 calc R U . . .
C7 C 0.4453(7) 0.725(2) 0.349(2) 0.027(3) Uani 1 1 d . . . . .
H7 H 0.4609 0.8460 0.2780 0.033 Uiso 1 1 calc R U . . .
N1 N 0.4828(6) 0.547(2) 0.4001(19) 0.032(3) Uani 1 1 d . . . . .
N2 N 0.5393(6) 0.523(2) 0.3346(19) 0.029(3) Uani 1 1 d . . . . .
H2A H 0.541(8) 0.61(4) 0.24(3) 0.035 Uiso 1 1 d . U . . .
C8 C 0.5805(7) 0.330(3) 0.387(2) 0.027(3) Uani 1 1 d . . . . .
O1 O 0.5766(5) 0.2223(19) 0.5257(17) 0.034(3) Uani 1 1 d . . . . .
C9 C 0.6319(8) 0.278(3) 0.272(2) 0.032(4) Uani 1 1 d . . . . .
H9A H 0.6303 0.4057 0.1809 0.039 Uiso 1 1 calc R U . . .
H9B H 0.6208 0.1246 0.2092 0.039 Uiso 1 1 calc R U . . .
C11 C 0.7012(8) 0.263(3) 0.370(2) 0.028(3) Uani 1 1 d . . . . .
C12 C 0.7470(7) 0.444(2) 0.354(2) 0.028(3) Uani 1 1 d . . . . .
H12 H 0.7329 0.5819 0.2851 0.033 Uiso 1 1 calc R U . . .
C13 C 0.8109(8) 0.431(2) 0.433(2) 0.034(3) Uani 1 1 d . . . . .
H13 H 0.8419 0.5509 0.4138 0.040 Uiso 1 1 calc R U . . .
C14 C 0.8305(6) 0.231(2) 0.547(3) 0.034(3) Uani 1 1 d . U . . .
Br1 Br 0.91910(7) 0.2119(3) 0.65708(10) 0.0388(5) Uani 1 1 d . . . . .
C15 C 0.7866(7) 0.045(3) 0.559(2) 0.030(3) Uani 1 1 d . . . . .
H15 H 0.8004 -0.0942 0.6258 0.036 Uiso 1 1 calc R U . . .
C16 C 0.7225(8) 0.064(3) 0.473(2) 0.034(4) Uani 1 1 d . . . . .
H16 H 0.6922 -0.0625 0.4835 0.041 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
C1' C6' 1.393(19) . ?
C1' C2' 1.41(2) . ?
C1' C1 1.48(2) . y
C2' C3' 1.379(19) . ?
C2' H2' 0.9500 . ?
C3' C4' 1.392(19) . ?
C3' H3' 0.9500 . ?
C4' C5' 1.42(2) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.36(2) . ?
C5' H5' 0.9500 . ?
C6' H6' 0.9500 . ?
C1 C6 1.420(19) . ?
C1 C2 1.42(2) . ?
C2 C3 1.362(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.42(2) . ?
C4 C7 1.447(19) . y
C5 C6 1.34(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.281(18) . y
C7 H7 0.9500 . ?
N1 N2 1.332(17) . y
N2 C8 1.385(19) . y
N2 H2A 0.9(2) . ?
C8 O1 1.23(2) . y
C8 C9 1.50(2) . y
C9 C11 1.50(3) . y
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 C16 1.39(2) . ?
C11 C12 1.397(19) . ?
C12 C13 1.36(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.43(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(19) . ?
C14 Br1 1.882(15) . y
C15 C16 1.38(2) . ?
C15 H15 0.9500 . ?
C16 H16 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
C6' C1' C2' 117.2(14) . . ?
C6' C1' C1 122.9(13) . . ?
C2' C1' C1 119.8(13) . . y
C3' C2' C1' 121.0(13) . . ?
C3' C2' H2' 119.5 . . ?
C1' C2' H2' 119.5 . . ?
C2' C3' C4' 120.9(13) . . ?
C2' C3' H3' 119.6 . . ?
C4' C3' H3' 119.6 . . ?
C3' C4' C5' 118.4(13) . . ?
C3' C4' H4' 120.8 . . ?
C5' C4' H4' 120.8 . . ?
C6' C5' C4' 119.8(12) . . ?
C6' C5' H5' 120.1 . . ?
C4' C5' H5' 120.1 . . ?
C5' C6' C1' 122.6(13) . . ?
C5' C6' H6' 118.7 . . ?
C1' C6' H6' 118.7 . . ?
C6 C1 C2 115.0(13) . . ?
C6 C1 C1' 122.5(13) . . ?
C2 C1 C1' 122.3(13) . . y
C3 C2 C1 121.5(13) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 123.0(13) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C3 C4 C5 115.4(13) . . ?
C3 C4 C7 123.3(12) . . ?
C5 C4 C7 121.3(12) . . ?
C6 C5 C4 122.5(13) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C1 122.4(13) . . ?
C5 C6 H6 118.8 . . ?
C1 C6 H6 118.8 . . ?
N1 C7 C4 121.4(13) . . ?
N1 C7 H7 119.3 . . ?
C4 C7 H7 119.3 . . ?
C7 N1 N2 118.5(13) . . y
N1 N2 C8 119.5(13) . . y
N1 N2 H2A 113(10) . . ?
C8 N2 H2A 126(10) . . ?
O1 C8 N2 120.9(14) . . y
O1 C8 C9 123.5(15) . . y
N2 C8 C9 115.4(14) . . y
C8 C9 C11 114.1(15) . . ?
C8 C9 H9A 108.7 . . ?
C11 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C11 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C16 C11 C12 118.0(15) . . ?
C16 C11 C9 121.4(14) . . ?
C12 C11 C9 120.5(14) . . ?
C13 C12 C11 122.2(13) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C14 118.5(12) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C15 C14 C13 119.7(14) . . ?
C15 C14 Br1 121.5(12) . . ?
C13 C14 Br1 118.4(10) . . ?
C14 C15 C16 119.6(14) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C11 121.7(14) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?

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
C6' C1' C2' C3' 1(2) . . . . ?
C1 C1' C2' C3' -178.9(14) . . . . ?
C1' C2' C3' C4' 0(2) . . . . ?
C2' C3' C4' C5' -1(2) . . . . ?
C3' C4' C5' C6' 2(2) . . . . ?
C4' C5' C6' C1' -1(2) . . . . ?
C2' C1' C6' C5' 0(2) . . . . ?
C1 C1' C6' C5' 179.3(15) . . . . ?
C6' C1' C1 C6 -177.0(15) . . . . ?
C2' C1' C1 C6 3(2) . . . . ?
C6' C1' C1 C2 -2(2) . . . . ?
C2' C1' C1 C2 177.8(15) . . . . ?
C6 C1 C2 C3 -3(2) . . . . ?
C1' C1 C2 C3 -178.3(15) . . . . ?
C1 C2 C3 C4 5(2) . . . . ?
C2 C3 C4 C5 -5(2) . . . . ?
C2 C3 C4 C7 172.1(14) . . . . ?
C3 C4 C5 C6 5(2) . . . . ?
C7 C4 C5 C6 -172.9(15) . . . . ?
C4 C5 C6 C1 -3(2) . . . . ?
C2 C1 C6 C5 2(2) . . . . ?
C1' C1 C6 C5 177.7(15) . . . . ?
C3 C4 C7 N1 178.8(15) . . . . ?
C5 C4 C7 N1 -4(2) . . . . ?
C4 C7 N1 N2 172.2(14) . . . . ?
C7 N1 N2 C8 -179.7(14) . . . . ?
N1 N2 C8 O1 -21(2) . . . . ?
N1 N2 C8 C9 163.3(14) . . . . ?
O1 C8 C9 C11 -48(2) . . . . ?
N2 C8 C9 C11 127.4(15) . . . . ?
C8 C9 C11 C16 75.0(18) . . . . ?
C8 C9 C11 C12 -107.9(17) . . . . ?
C16 C11 C12 C13 1(2) . . . . ?
C9 C11 C12 C13 -176.6(14) . . . . ?
C11 C12 C13 C14 -4(2) . . . . ?
C12 C13 C14 C15 7(2) . . . . ?
C12 C13 C14 Br1 179.9(11) . . . . ?
C13 C14 C15 C16 -6(2) . . . . ?
Br1 C14 C15 C16 -178.3(12) . . . . ?
C14 C15 C16 C11 2(2) . . . . ?
C12 C11 C16 C15 1(2) . . . . ?
C9 C11 C16 C15 178.1(14) . . . . ?

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
C9 H9B O1 0.99 2.48 3.46(2) 170.2 2_554
N2 H2A O1 0.9(2) 2.1(2) 2.951(18) 160(15) 2_564
C9 H9A O1 0.99 2.55 3.45(2) 151.0 2_564
C13 H13 Br1 0.95 3.00 3.836(14) 147.4 2_564

_refine_diff_density_max         3.267
_refine_diff_density_min         -0.995
_refine_diff_density_rms         0.193

