# 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_red
_database_code_depnum_ccdc_archive 'CCDC 1446736'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-08-03 downloaded from the CCDC.
;
_audit_creation_date             2016-01-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H15 Br Cl N3 O2)'
_chemical_formula_sum            'C38 H30 Br2 Cl2 N6 O4'
_chemical_formula_weight         865.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H12 N2 O1'
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'
Br Br -0.2901 2.4595 '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'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.4739(4)
_cell_length_b                   11.7125(11)
_cell_length_c                   15.0667(15)
_cell_angle_alpha                69.068(9)
_cell_angle_beta                 83.892(7)
_cell_angle_gamma                81.991(7)
_cell_volume                     891.75(15)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2494
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.7830
_cell_measurement_theta_min      2.7480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.474
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6091
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.739
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0419
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  53.00   1.00    5.00    --  -14.38  57.00 -60.00   83
  2  ω     55.00  81.00   1.00    5.00    --   18.60  57.00   0.00   26
  3  ω     -2.00  25.00   1.00    5.00    --  -14.38 -99.00-180.00   27
  4  ω    -20.00  19.00   1.00    5.00    --  -14.38 -99.00 -60.00   39
  5  ω    -82.00  11.00   1.00    5.00    --  -14.38 -77.00  60.00   93
  6  ω    -41.00  49.00   1.00    5.00    --  -14.38  77.00-180.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0104460000
_diffrn_orient_matrix_UB_12      0.0555650000
_diffrn_orient_matrix_UB_13      -0.0390985000
_diffrn_orient_matrix_UB_21      0.0289495000
_diffrn_orient_matrix_UB_22      -0.0339079000
_diffrn_orient_matrix_UB_23      -0.0311600000
_diffrn_orient_matrix_UB_31      -0.1274365000
_diffrn_orient_matrix_UB_32      0.0041722000
_diffrn_orient_matrix_UB_33      -0.0071031000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2320
_reflns_number_total             3153
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.128
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0574
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0753P)²+0.3464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1597
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00E(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C00P(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 N004(H004), C00F(H00F), C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O)
2.d Idealised Me refined as rotating group:
 C00Q(H00C,H00D,H00G)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
Br01 Br 0.74930(13) 0.33227(5) 0.64996(4) 0.0789(3) Uani 1 1 d . . . . .
Cl00 Cl 0.2350(3) 0.15236(14) 0.44417(10) 0.0730(4) Uani 1 1 d . . . . .
O003 O 0.1414(6) 0.6979(3) 0.1246(2) 0.0562(9) Uani 1 1 d . . . . .
N004 N 1.0063(7) 0.3435(3) 0.0934(3) 0.0460(9) Uani 1 1 d . . . . .
H004 H 1.1001 0.3790 0.0445 0.055 Uiso 1 1 calc R . . . .
N005 N 0.6930(6) 0.3110(3) 0.2039(2) 0.0412(9) Uani 1 1 d . . . . .
N006 N 0.6871(6) 0.5083(3) 0.0848(3) 0.0460(9) Uani 1 1 d . . . . .
O007 O 0.4317(7) 0.7328(4) 0.0053(3) 0.0778(12) Uani 1 1 d . . . . .
C008 C 0.4592(8) 0.5396(4) 0.1271(3) 0.0436(11) Uani 1 1 d . . . . .
C009 C 0.8481(8) 0.2024(4) 0.2267(3) 0.0424(10) Uani 1 1 d . . . . .
C00A C 0.7964(8) 0.3914(4) 0.1244(3) 0.0405(10) Uani 1 1 d . . . . .
C00B C 0.5392(7) 0.3303(4) 0.3579(3) 0.0398(10) Uani 1 1 d . . . . .
C00C C 0.4379(8) 0.2537(4) 0.4437(3) 0.0438(10) Uani 1 1 d . . . . .
C00D C 1.0430(8) 0.2234(4) 0.1569(3) 0.0439(11) Uani 1 1 d . . . . .
C00E C 0.4721(8) 0.3363(4) 0.2602(3) 0.0447(11) Uani 1 1 d . . . . .
H00E H 0.3566 0.2760 0.2683 0.054 Uiso 1 1 calc R . . . .
C00F C 0.3552(8) 0.4627(4) 0.2059(3) 0.0449(11) Uani 1 1 d . . . . .
H00F H 0.2010 0.4890 0.2285 0.054 Uiso 1 1 calc R . . . .
C00G C 0.3466(9) 0.6659(5) 0.0781(4) 0.0510(12) Uani 1 1 d . . . . .
C00H C 0.8359(9) 0.0909(4) 0.3006(3) 0.0524(12) Uani 1 1 d . . . . .
H00H H 0.7047 0.0783 0.3464 0.063 Uiso 1 1 calc R . . . .
C00I C 0.6632(10) 0.3318(4) 0.5318(3) 0.0532(13) Uani 1 1 d . . . . .
C00J C 0.5017(9) 0.2533(4) 0.5295(3) 0.0541(13) Uani 1 1 d . . . . .
H00J H 0.4355 0.1999 0.5861 0.065 Uiso 1 1 calc R . . . .
C00K C 0.7012(8) 0.4084(4) 0.3627(3) 0.0499(12) Uani 1 1 d . . . . .
H00K H 0.7682 0.4620 0.3064 0.060 Uiso 1 1 calc R . . . .
C00L C 0.7666(9) 0.4092(4) 0.4488(4) 0.0544(12) Uani 1 1 d . . . . .
H00L H 0.8786 0.4612 0.4503 0.065 Uiso 1 1 calc R . . . .
C00M C 1.2206(10) 0.0195(5) 0.2361(4) 0.0608(14) Uani 1 1 d . . . . .
H00M H 1.3480 -0.0434 0.2406 0.073 Uiso 1 1 calc R . . . .
C00N C 1.2325(9) 0.1303(5) 0.1621(4) 0.0569(13) Uani 1 1 d . . . . .
H00N H 1.3649 0.1420 0.1168 0.068 Uiso 1 1 calc R . . . .
C00O C 1.0254(10) -0.0004(5) 0.3035(4) 0.0593(13) Uani 1 1 d . . . . .
H00O H 1.0217 -0.0767 0.3517 0.071 Uiso 1 1 calc R . . . .
C00P C 0.0234(10) 0.8224(5) 0.0798(4) 0.0768(18) Uani 1 1 d . . . . .
H00A H -0.0246 0.8330 0.0169 0.092 Uiso 1 1 calc R . . . .
H00B H 0.1369 0.8819 0.0732 0.092 Uiso 1 1 calc R . . . .
C00Q C -0.1988(10) 0.8406(6) 0.1416(5) 0.090(2) Uani 1 1 d . . . . .
H00C H -0.3055 0.9109 0.1062 0.135 Uiso 1 1 calc GR . . . .
H00D H -0.1483 0.8538 0.1960 0.135 Uiso 1 1 calc GR . . . .
H00G H -0.2858 0.7689 0.1625 0.135 Uiso 1 1 calc GR . . . .


_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
Br01 C00I 1.891(5) . ?
Cl00 C00C 1.733(5) . ?
O003 C00G 1.340(6) . ?
O003 C00P 1.458(6) . ?
N004 H004 0.8600 . ?
N004 C00A 1.321(5) . ?
N004 C00D 1.391(5) . ?
N005 C009 1.380(5) . ?
N005 C00A 1.357(6) . ?
N005 C00E 1.460(5) . ?
N006 C008 1.402(5) . ?
N006 C00A 1.362(6) . ?
O007 C00G 1.189(6) . ?
C008 C00F 1.334(6) . ?
C008 C00G 1.475(6) . ?
C009 C00D 1.398(6) . ?
C009 C00H 1.385(6) . ?
C00B C00C 1.393(6) . ?
C00B C00E 1.530(6) . ?
C00B C00K 1.385(6) . ?
C00C C00J 1.374(6) . ?
C00D C00N 1.383(6) . ?
C00E H00E 0.9800 . ?
C00E C00F 1.501(6) . ?
C00F H00F 0.9300 . ?
C00H H00H 0.9300 . ?
C00H C00O 1.374(7) . ?
C00I C00J 1.372(7) . ?
C00I C00L 1.375(7) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00L 1.385(7) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00N 1.381(7) . ?
C00M C00O 1.378(7) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00P H00A 0.9700 . ?
C00P H00B 0.9700 . ?
C00P C00Q 1.491(7) . ?
C00Q H00C 0.9600 . ?
C00Q H00D 0.9600 . ?
C00Q H00G 0.9600 . ?

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
C00G O003 C00P 115.6(4) . . ?
C00A N004 H004 127.4 . . ?
C00A N004 C00D 105.2(4) . . ?
C00D N004 H004 127.4 . . ?
C009 N005 C00E 125.9(4) . . ?
C00A N005 C009 106.9(3) . . ?
C00A N005 C00E 127.0(4) . . ?
C00A N006 C008 117.2(4) . . ?
N006 C008 C00G 114.2(4) . . ?
C00F C008 N006 123.0(4) . . ?
C00F C008 C00G 122.8(4) . . ?
N005 C009 C00D 105.7(4) . . ?
N005 C009 C00H 131.9(4) . . ?
C00H C009 C00D 122.4(4) . . ?
N004 C00A N005 112.9(4) . . ?
N004 C00A N006 126.2(4) . . ?
N005 C00A N006 120.9(4) . . ?
C00C C00B C00E 123.7(4) . . ?
C00K C00B C00C 117.3(4) . . ?
C00K C00B C00E 119.0(4) . . ?
C00B C00C Cl00 120.3(4) . . ?
C00J C00C Cl00 118.3(4) . . ?
C00J C00C C00B 121.3(4) . . ?
N004 C00D C009 109.3(4) . . ?
C00N C00D N004 131.6(4) . . ?
C00N C00D C009 119.1(4) . . ?
N005 C00E C00B 110.7(3) . . ?
N005 C00E H00E 109.5 . . ?
N005 C00E C00F 107.4(4) . . ?
C00B C00E H00E 109.5 . . ?
C00F C00E C00B 110.3(3) . . ?
C00F C00E H00E 109.5 . . ?
C008 C00F C00E 123.9(4) . . ?
C008 C00F H00F 118.0 . . ?
C00E C00F H00F 118.0 . . ?
O003 C00G C008 113.2(4) . . ?
O007 C00G O003 123.6(4) . . ?
O007 C00G C008 123.2(4) . . ?
C009 C00H H00H 121.3 . . ?
C00O C00H C009 117.3(4) . . ?
C00O C00H H00H 121.3 . . ?
C00J C00I Br01 120.0(4) . . ?
C00J C00I C00L 120.5(4) . . ?
C00L C00I Br01 119.4(4) . . ?
C00C C00J H00J 120.0 . . ?
C00I C00J C00C 119.9(5) . . ?
C00I C00J H00J 120.0 . . ?
C00B C00K H00K 119.0 . . ?
C00L C00K C00B 122.0(5) . . ?
C00L C00K H00K 119.0 . . ?
C00I C00L C00K 118.9(5) . . ?
C00I C00L H00L 120.5 . . ?
C00K C00L H00L 120.5 . . ?
C00N C00M H00M 119.1 . . ?
C00O C00M H00M 119.1 . . ?
C00O C00M C00N 121.8(5) . . ?
C00D C00N H00N 120.8 . . ?
C00M C00N C00D 118.4(4) . . ?
C00M C00N H00N 120.8 . . ?
C00H C00O C00M 121.0(5) . . ?
C00H C00O H00O 119.5 . . ?
C00M C00O H00O 119.5 . . ?
O003 C00P H00A 110.2 . . ?
O003 C00P H00B 110.2 . . ?
O003 C00P C00Q 107.6(5) . . ?
H00A C00P H00B 108.5 . . ?
C00Q C00P H00A 110.2 . . ?
C00Q C00P H00B 110.2 . . ?
C00P C00Q H00C 109.5 . . ?
C00P C00Q H00D 109.5 . . ?
C00P C00Q H00G 109.5 . . ?
H00C C00Q H00D 109.5 . . ?
H00C C00Q H00G 109.5 . . ?
H00D C00Q H00G 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.125
_oxdiff_exptl_absorpt_empirical_full_min 0.852
####################################################################### 
# 
# 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_red
_database_code_depnum_ccdc_archive 'CCDC 1456725'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-08-03 downloaded from the CCDC.
;
_audit_creation_date             2016-01-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        NEW
_chemical_formula_moiety         'C15 H16 N4 O3'
_chemical_formula_sum            'C15 H16 N4 O3'
_chemical_formula_weight         300.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5410(8)
_cell_length_b                   7.7485(8)
_cell_length_c                   13.2889(12)
_cell_angle_alpha                82.835(8)
_cell_angle_beta                 83.414(8)
_cell_angle_gamma                81.361(9)
_cell_volume                     758.03(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2589
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.0350
_cell_measurement_theta_min      3.2320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5343
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.675
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0419
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     47.00  83.00   1.00   12.50    --   26.06  57.00 -60.00   36
  2  ω     -1.00  94.00   1.00   12.50    --   26.06  77.00-120.00   95
  3  ω     67.00  98.00   1.00   12.50    --   26.06 179.00 -90.00   31
  4  ω    -89.00  22.00   1.00   12.50    --  -21.68   0.00 -90.00  111
  5  ω    -20.00  65.00   1.00   12.50    --   26.06 -99.00 120.00   85
  6  ω     13.00  65.00   1.00   12.50    --   26.06 -99.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0068471000
_diffrn_orient_matrix_UB_12      0.0330796000
_diffrn_orient_matrix_UB_13      0.0466200000
_diffrn_orient_matrix_UB_21      0.0598421000
_diffrn_orient_matrix_UB_22      0.0571737000
_diffrn_orient_matrix_UB_23      -0.0256357000
_diffrn_orient_matrix_UB_31      -0.0742354000
_diffrn_orient_matrix_UB_32      0.0656802000
_diffrn_orient_matrix_UB_33      -0.0095557000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1944
_reflns_number_total             2664
_reflns_odcompleteness_completeness 60.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2664
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0563
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0859P)²+0.0076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1510
_refine_ls_wR_factor_ref         0.1709
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6C(H6C)
2.b Secondary CH2 refined with riding coordinates:
 C2C(H2CA,H2CB)
2.c Aromatic/amide H refined with riding coordinates:
 N4N(H4N), C13C(H13C), C5C(H5C), C8C(H8C), C12C(H12C), C9C(H9C), C14C(H14C)
2.d Idealised Me refined as rotating group:
 C11C(H11A,H11B,H11C), C1C(H1CA,H1CB,H1CC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1O O 0.7055(2) -0.06879(19) 0.53592(12) 0.0682(5) Uani 1 1 d . . . . .
O3O O 0.3700(2) 0.7994(2) 0.86502(11) 0.0673(5) Uani 1 1 d . . . . .
N1N N 0.9697(2) 0.5120(2) 0.75111(12) 0.0484(4) Uani 1 1 d . . . . .
O2O O 0.5024(2) 0.7225(2) 1.00970(12) 0.0782(6) Uani 1 1 d . . . . .
N4N N 0.8065(2) 0.5715(3) 0.90656(13) 0.0616(5) Uani 1 1 d . . . . .
H4N H 0.7998 0.5673 0.9718 0.074 Uiso 1 1 calc R . . . .
N3N N 1.1212(2) 0.4500(3) 0.88523(13) 0.0613(5) Uani 1 1 d . . . . .
N2N N 1.1422(2) 0.4478(2) 0.71334(13) 0.0579(5) Uani 1 1 d . . . . .
C7C C 0.7812(3) 0.3917(2) 0.64461(14) 0.0437(5) Uani 1 1 d . . . . .
C4C C 0.6594(3) 0.6405(3) 0.85370(15) 0.0494(5) Uani 1 1 d . . . . .
C13C C 0.7351(3) 0.2475(3) 0.70899(15) 0.0497(5) Uani 1 1 d . . . . .
H13C H 0.7212 0.2520 0.7791 0.060 Uiso 1 1 calc R . . . .
C15C C 0.9617(3) 0.5108(3) 0.85194(15) 0.0502(5) Uani 1 1 d . . . . .
C10C C 0.7304(3) 0.0879(3) 0.56603(16) 0.0508(5) Uani 1 1 d . . . . .
C6C C 0.8182(3) 0.5548(3) 0.68731(15) 0.0480(5) Uani 1 1 d . . . . .
H6C H 0.8487 0.6422 0.6306 0.058 Uiso 1 1 calc R . . . .
C5C C 0.6607(3) 0.6352(3) 0.75442(15) 0.0491(5) Uani 1 1 d . . . . .
H5C H 0.5571 0.6847 0.7240 0.059 Uiso 1 1 calc R . . . .
C8C C 0.7965(3) 0.3837(3) 0.54096(15) 0.0538(5) Uani 1 1 d . . . . .
H8C H 0.8252 0.4807 0.4969 0.065 Uiso 1 1 calc R . . . .
C3C C 0.5042(3) 0.7228(3) 0.91887(16) 0.0558(6) Uani 1 1 d . . . . .
C12C C 0.7096(3) 0.0975(3) 0.67036(16) 0.0566(6) Uani 1 1 d . . . . .
H12C H 0.6781 0.0016 0.7145 0.068 Uiso 1 1 calc R . . . .
C9C C 0.7695(3) 0.2323(3) 0.50095(16) 0.0558(6) Uani 1 1 d . . . . .
H9C H 0.7780 0.2293 0.4308 0.067 Uiso 1 1 calc R . . . .
C14C C 1.2242(3) 0.4155(3) 0.79708(16) 0.0626(6) Uani 1 1 d . . . . .
H14C H 1.3460 0.3714 0.7962 0.075 Uiso 1 1 calc R . . . .
C11C C 0.7379(4) -0.0882(3) 0.42972(19) 0.0757(8) Uani 1 1 d . . . . .
H11A H 0.6577 -0.0014 0.3928 0.114 Uiso 1 1 calc GR . . . .
H11B H 0.7175 -0.2033 0.4186 0.114 Uiso 1 1 calc GR . . . .
H11C H 0.8604 -0.0727 0.4063 0.114 Uiso 1 1 calc GR . . . .
C2C C 0.2111(3) 0.8841(4) 0.92084(18) 0.0776(8) Uani 1 1 d . . . . .
H2CA H 0.2423 0.9770 0.9553 0.093 Uiso 1 1 calc R . . . .
H2CB H 0.1594 0.7996 0.9715 0.093 Uiso 1 1 calc R . . . .
C1C C 0.0801(4) 0.9579(4) 0.8460(2) 0.0933(10) Uani 1 1 d . . . . .
H1CA H 0.1292 1.0476 0.7993 0.140 Uiso 1 1 calc GR . . . .
H1CB H -0.0303 1.0076 0.8813 0.140 Uiso 1 1 calc GR . . . .
H1CC H 0.0568 0.8662 0.8090 0.140 Uiso 1 1 calc GR . . . .


_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
O1O C10C 1.370(2) . ?
O1O C11C 1.427(3) . ?
O3O C3C 1.330(3) . ?
O3O C2C 1.448(2) . ?
N1N N2N 1.382(2) . ?
N1N C15C 1.333(2) . ?
N1N C6C 1.474(3) . ?
O2O C3C 1.205(2) . ?
N4N H4N 0.8600 . ?
N4N C4C 1.385(3) . ?
N4N C15C 1.357(2) . ?
N3N C15C 1.328(3) . ?
N3N C14C 1.362(3) . ?
N2N C14C 1.314(3) . ?
C7C C13C 1.383(3) . ?
C7C C6C 1.522(3) . ?
C7C C8C 1.377(3) . ?
C4C C5C 1.324(3) . ?
C4C C3C 1.486(3) . ?
C13C H13C 0.9300 . ?
C13C C12C 1.375(3) . ?
C10C C12C 1.387(3) . ?
C10C C9C 1.373(3) . ?
C6C H6C 0.9800 . ?
C6C C5C 1.506(3) . ?
C5C H5C 0.9300 . ?
C8C H8C 0.9300 . ?
C8C C9C 1.397(3) . ?
C12C H12C 0.9300 . ?
C9C H9C 0.9300 . ?
C14C H14C 0.9300 . ?
C11C H11A 0.9600 . ?
C11C H11B 0.9600 . ?
C11C H11C 0.9600 . ?
C2C H2CA 0.9700 . ?
C2C H2CB 0.9700 . ?
C2C C1C 1.485(3) . ?
C1C H1CA 0.9600 . ?
C1C H1CB 0.9600 . ?
C1C H1CC 0.9600 . ?

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
C10C O1O C11C 117.45(19) . . ?
C3C O3O C2C 116.96(17) . . ?
N2N N1N C6C 122.83(15) . . ?
C15C N1N N2N 109.74(16) . . ?
C15C N1N C6C 127.10(17) . . ?
C4C N4N H4N 121.1 . . ?
C15C N4N H4N 121.1 . . ?
C15C N4N C4C 117.80(17) . . ?
C15C N3N C14C 101.83(18) . . ?
C14C N2N N1N 101.20(16) . . ?
C13C C7C C6C 120.74(17) . . ?
C8C C7C C13C 118.66(18) . . ?
C8C C7C C6C 120.59(18) . . ?
N4N C4C C3C 113.40(17) . . ?
C5C C4C N4N 122.47(19) . . ?
C5C C4C C3C 124.1(2) . . ?
C7C C13C H13C 119.7 . . ?
C12C C13C C7C 120.64(19) . . ?
C12C C13C H13C 119.7 . . ?
N1N C15C N4N 120.89(18) . . ?
N3N C15C N1N 110.84(17) . . ?
N3N C15C N4N 128.24(18) . . ?
O1O C10C C12C 115.7(2) . . ?
O1O C10C C9C 124.77(19) . . ?
C9C C10C C12C 119.50(18) . . ?
N1N C6C C7C 110.77(15) . . ?
N1N C6C H6C 109.0 . . ?
N1N C6C C5C 105.96(15) . . ?
C7C C6C H6C 109.0 . . ?
C5C C6C C7C 113.11(16) . . ?
C5C C6C H6C 109.0 . . ?
C4C C5C C6C 124.61(19) . . ?
C4C C5C H5C 117.7 . . ?
C6C C5C H5C 117.7 . . ?
C7C C8C H8C 119.4 . . ?
C7C C8C C9C 121.1(2) . . ?
C9C C8C H8C 119.4 . . ?
O3O C3C C4C 112.15(18) . . ?
O2O C3C O3O 124.2(2) . . ?
O2O C3C C4C 123.6(2) . . ?
C13C C12C C10C 120.5(2) . . ?
C13C C12C H12C 119.7 . . ?
C10C C12C H12C 119.7 . . ?
C10C C9C C8C 119.47(19) . . ?
C10C C9C H9C 120.3 . . ?
C8C C9C H9C 120.3 . . ?
N3N C14C H14C 121.8 . . ?
N2N C14C N3N 116.4(2) . . ?
N2N C14C H14C 121.8 . . ?
O1O C11C H11A 109.5 . . ?
O1O C11C H11B 109.5 . . ?
O1O C11C H11C 109.5 . . ?
H11A C11C H11B 109.5 . . ?
H11A C11C H11C 109.5 . . ?
H11B C11C H11C 109.5 . . ?
O3O C2C H2CA 110.2 . . ?
O3O C2C H2CB 110.2 . . ?
O3O C2C C1C 107.44(19) . . ?
H2CA C2C H2CB 108.5 . . ?
C1C C2C H2CA 110.2 . . ?
C1C C2C H2CB 110.2 . . ?
C2C C1C H1CA 109.5 . . ?
C2C C1C H1CB 109.5 . . ?
C2C C1C H1CC 109.5 . . ?
H1CA C1C H1CB 109.5 . . ?
H1CA C1C H1CC 109.5 . . ?
H1CB C1C H1CC 109.5 . . ?

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
O1O C10C C12C C13C 178.68(18) . . . . ?
O1O C10C C9C C8C -178.4(2) . . . . ?
N1N N2N C14C N3N 0.9(3) . . . . ?
N1N C6C C5C C4C -8.4(3) . . . . ?
N4N C4C C5C C6C 0.3(3) . . . . ?
N4N C4C C3C O3O 175.29(19) . . . . ?
N4N C4C C3C O2O -3.4(3) . . . . ?
N2N N1N C15C N4N 178.55(19) . . . . ?
N2N N1N C15C N3N 0.5(3) . . . . ?
N2N N1N C6C C7C 62.1(2) . . . . ?
N2N N1N C6C C5C -174.90(17) . . . . ?
C7C C13C C12C C10C 0.3(3) . . . . ?
C7C C6C C5C C4C 113.2(2) . . . . ?
C7C C8C C9C C10C -1.2(3) . . . . ?
C4C N4N C15C N1N -2.3(3) . . . . ?
C4C N4N C15C N3N 175.3(2) . . . . ?
C13C C7C C6C N1N 60.0(2) . . . . ?
C13C C7C C6C C5C -58.8(2) . . . . ?
C13C C7C C8C C9C -1.2(3) . . . . ?
C15C N1N N2N C14C -0.8(2) . . . . ?
C15C N1N C6C C7C -110.7(2) . . . . ?
C15C N1N C6C C5C 12.3(3) . . . . ?
C15C N4N C4C C5C 5.9(3) . . . . ?
C15C N4N C4C C3C -172.95(18) . . . . ?
C15C N3N C14C N2N -0.6(3) . . . . ?
C6C N1N N2N C14C -174.70(19) . . . . ?
C6C N1N C15C N4N -7.9(3) . . . . ?
C6C N1N C15C N3N 174.05(19) . . . . ?
C6C C7C C13C C12C -177.10(18) . . . . ?
C6C C7C C8C C9C 177.57(18) . . . . ?
C5C C4C C3C O3O -3.5(3) . . . . ?
C5C C4C C3C O2O 177.8(2) . . . . ?
C8C C7C C13C C12C 1.7(3) . . . . ?
C8C C7C C6C N1N -118.7(2) . . . . ?
C8C C7C C6C C5C 122.5(2) . . . . ?
C3C O3O C2C C1C -179.4(2) . . . . ?
C3C C4C C5C C6C 179.01(19) . . . . ?
C12C C10C C9C C8C 3.1(3) . . . . ?
C9C C10C C12C C13C -2.7(3) . . . . ?
C14C N3N C15C N1N 0.1(2) . . . . ?
C14C N3N C15C N4N -177.8(2) . . . . ?
C11C O1O C10C C12C -175.76(17) . . . . ?
C11C O1O C10C C9C 5.7(3) . . . . ?
C2C O3O C3C O2O -1.4(4) . . . . ?
C2C O3O C3C C4C 179.98(19) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.568
_oxdiff_exptl_absorpt_empirical_full_min 0.775
