# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_zyl-149
_database_code_depnum_ccdc_archive 'CCDC 1444877'
_audit_update_record             
;
2015-12-31 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        6o
_chemical_name_common            ?
_chemical_melting_point          '180-181 \%C'
_chemical_formula_moiety         'C21 H20 Br N3 O2'
_chemical_formula_sum            'C21 H20 Br N3 O2'
_chemical_formula_weight         426.31

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.5763(14)
_cell_length_b                   8.0259(7)
_cell_length_c                   15.6946(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.896(2)
_cell_angle_gamma                90.00
_cell_volume                     1963.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      26.99

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    2.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8587
_exptl_absorpt_correction_T_max  0.9116
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16844
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.06
_reflns_number_total             3457
_reflns_number_gt                2428
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0501P)²+2.1703P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3457
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1265
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.21302(3) 0.47428(7) 0.56219(3) 0.0801(2) Uani 1 1 d . . .
C9 C 0.36188(19) 0.5348(4) 0.3049(2) 0.0354(7) Uani 1 1 d . . .
N2 N 0.28259(17) 0.2753(3) 0.25384(19) 0.0398(7) Uani 1 1 d . . .
O2 O 0.05571(17) 0.6624(3) 0.1170(2) 0.0657(8) Uani 1 1 d . . .
N1 N 0.47061(17) 0.6860(3) 0.3952(2) 0.0456(7) Uani 1 1 d . . .
N3 N 0.19554(17) 0.2534(3) 0.23672(19) 0.0401(7) Uani 1 1 d . . .
C8 C 0.3485(2) 0.5597(4) 0.3893(2) 0.0345(7) Uani 1 1 d . . .
O1 O 0.41344(16) 0.1655(3) 0.28994(18) 0.0594(7) Uani 1 1 d . . .
C6 C 0.2951(2) 0.5527(5) 0.5114(2) 0.0465(9) Uani 1 1 d . . .
C14 C 0.1557(2) 0.3842(4) 0.1961(2) 0.0360(8) Uani 1 1 d . . .
C15 C 0.0615(2) 0.3868(4) 0.1673(2) 0.0400(8) Uani 1 1 d . . .
C12 C 0.3043(2) 0.4399(4) 0.2254(2) 0.0394(8) Uani 1 1 d . . .
H12 H 0.3318 0.4263 0.1796 0.047 Uiso 1 1 calc R . .
C13 C 0.2142(2) 0.5160(4) 0.1820(2) 0.0446(9) Uani 1 1 d . . .
H13A H 0.2088 0.6191 0.2118 0.054 Uiso 1 1 calc R . .
H13B H 0.2018 0.5375 0.1180 0.054 Uiso 1 1 calc R . .
C1 C 0.4365(2) 0.6124(4) 0.3122(3) 0.0434(8) Uani 1 1 d . . .
H1 H 0.4611 0.6151 0.2670 0.052 Uiso 1 1 calc R . .
C4 C 0.4258(2) 0.6985(5) 0.5329(3) 0.0537(10) Uani 1 1 d . . .
H4 H 0.4719 0.7620 0.5684 0.064 Uiso 1 1 calc R . .
C20 C 0.0123(2) 0.5243(5) 0.1253(2) 0.0466(9) Uani 1 1 d . . .
C11 C 0.3386(2) 0.1488(4) 0.2856(2) 0.0456(9) Uani 1 1 d . . .
C3 C 0.4181(2) 0.6546(4) 0.4447(2) 0.0407(8) Uani 1 1 d . . .
C5 C 0.3638(3) 0.6458(5) 0.5657(3) 0.0568(10) Uani 1 1 d . . .
H5 H 0.3677 0.6723 0.6246 0.068 Uiso 1 1 calc R . .
C16 C 0.0184(2) 0.2449(5) 0.1797(3) 0.0555(10) Uani 1 1 d . . .
H16 H 0.0501 0.1533 0.2091 0.067 Uiso 1 1 calc R . .
C19 C -0.0770(3) 0.5146(6) 0.0943(3) 0.0627(12) Uani 1 1 d . . .
H19 H -0.1098 0.6052 0.0651 0.075 Uiso 1 1 calc R . .
C7 C 0.2855(2) 0.5076(4) 0.4242(2) 0.0397(8) Uani 1 1 d . . .
H7 H 0.2388 0.4447 0.3895 0.048 Uiso 1 1 calc R . .
C10 C 0.3062(3) -0.0055(5) 0.3161(3) 0.0670(12) Uani 1 1 d . . .
H10A H 0.3397 -0.0993 0.3098 0.100 Uiso 1 1 calc R . .
H10B H 0.2472 -0.0228 0.2795 0.100 Uiso 1 1 calc R . .
H10C H 0.3107 0.0062 0.3784 0.100 Uiso 1 1 calc R . .
C21 C 0.0087(3) 0.8087(6) 0.0795(4) 0.0881(16) Uani 1 1 d . . .
H21A H -0.0260 0.7882 0.0175 0.132 Uiso 1 1 calc R . .
H21B H 0.0478 0.8982 0.0820 0.132 Uiso 1 1 calc R . .
H21C H -0.0275 0.8384 0.1135 0.132 Uiso 1 1 calc R . .
C17 C -0.0695(3) 0.2362(6) 0.1499(3) 0.0695(12) Uani 1 1 d . . .
H17 H -0.0968 0.1399 0.1588 0.083 Uiso 1 1 calc R . .
C18 C -0.1164(3) 0.3705(7) 0.1069(3) 0.0707(13) Uani 1 1 d . . .
H18 H -0.1760 0.3645 0.0860 0.085 Uiso 1 1 calc R . .
C2 C 0.5486(2) 0.7862(5) 0.4253(3) 0.0716(13) Uani 1 1 d . . .
H2A H 0.5823 0.7555 0.4861 0.107 Uiso 1 1 calc R . .
H2B H 0.5336 0.9020 0.4237 0.107 Uiso 1 1 calc R . .
H2C H 0.5811 0.7672 0.3860 0.107 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 C6 1.902(4) . ?
C9 C1 1.355(5) . ?
C9 C8 1.430(5) . ?
C9 C12 1.496(5) . ?
N2 C11 1.352(4) . ?
N2 N3 1.386(4) . ?
N2 C12 1.478(4) . ?
O2 C20 1.352(4) . ?
O2 C21 1.421(5) . ?
N1 C1 1.366(5) . ?
N1 C3 1.373(4) . ?
N1 C2 1.458(4) . ?
N3 C14 1.288(4) . ?
C8 C7 1.397(5) . ?
C8 C3 1.408(4) . ?
O1 C11 1.226(4) . ?
C6 C7 1.372(5) . ?
C6 C5 1.387(5) . ?
C14 C15 1.470(4) . ?
C14 C13 1.502(5) . ?
C15 C16 1.393(5) . ?
C15 C20 1.397(5) . ?
C12 C13 1.541(5) . ?
C4 C5 1.364(6) . ?
C4 C3 1.391(5) . ?
C20 C19 1.394(5) . ?
C11 C10 1.493(6) . ?
C16 C17 1.371(5) . ?
C19 C18 1.375(6) . ?
C17 C18 1.365(6) . ?

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
C1 C9 C8 106.4(3) . . ?
C1 C9 C12 127.5(3) . . ?
C8 C9 C12 126.0(3) . . ?
C11 N2 N3 121.0(3) . . ?
C11 N2 C12 125.1(3) . . ?
N3 N2 C12 113.5(2) . . ?
C20 O2 C21 118.8(3) . . ?
C1 N1 C3 108.9(3) . . ?
C1 N1 C2 125.6(3) . . ?
C3 N1 C2 125.5(3) . . ?
C14 N3 N2 108.5(3) . . ?
C7 C8 C3 119.0(3) . . ?
C7 C8 C9 133.9(3) . . ?
C3 C8 C9 107.1(3) . . ?
C7 C6 C5 123.2(3) . . ?
C7 C6 Br1 118.3(3) . . ?
C5 C6 Br1 118.4(3) . . ?
N3 C14 C15 118.5(3) . . ?
N3 C14 C13 113.5(3) . . ?
C15 C14 C13 128.0(3) . . ?
C16 C15 C20 117.8(3) . . ?
C16 C15 C14 119.1(3) . . ?
C20 C15 C14 123.0(3) . . ?
N2 C12 C9 110.8(3) . . ?
N2 C12 C13 100.9(3) . . ?
C9 C12 C13 114.5(3) . . ?
C14 C13 C12 103.5(3) . . ?
C9 C1 N1 110.4(3) . . ?
C5 C4 C3 118.1(3) . . ?
O2 C20 C19 123.3(3) . . ?
O2 C20 C15 116.7(3) . . ?
C19 C20 C15 120.0(4) . . ?
O1 C11 N2 119.6(3) . . ?
O1 C11 C10 122.7(3) . . ?
N2 C11 C10 117.6(3) . . ?
N1 C3 C4 130.9(3) . . ?
N1 C3 C8 107.1(3) . . ?
C4 C3 C8 122.0(3) . . ?
C4 C5 C6 120.2(4) . . ?
C17 C16 C15 122.0(4) . . ?
C18 C19 C20 119.8(4) . . ?
C6 C7 C8 117.6(3) . . ?
C18 C17 C16 119.3(4) . . ?
C17 C18 C19 121.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.078
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol/dichloromethane'
