# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1589822'
_audit_update_record             
;
2018-05-22 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H28 N6 O10 S'
_chemical_formula_weight         640.62

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.9630(2)
_cell_length_b                   12.5373(4)
_cell_length_c                   16.3477(5)
_cell_angle_alpha                84.055(3)
_cell_angle_beta                 78.144(3)
_cell_angle_gamma                89.449(3)
_cell_volume                     1389.05(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9934
_cell_measurement_theta_min      4.3700
_cell_measurement_theta_max      32.1580

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             668
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.189
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19383
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.319
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4847
_reflns_number_gt                4498
_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       'CrysAlis CCD (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS (Sheldrick, 1990, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0135P)²+4.5151P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4847
_refine_ls_number_parameters     408
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1369
_refine_ls_wR_factor_gt          0.1355
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_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
S1 S -0.56949(11) 0.74798(6) 1.00173(5) 0.0187(2) Uani 1 1 d . . . . .
O11 O -0.0432(3) 1.0503(2) 0.67939(17) 0.0296(6) Uani 1 1 d . . . . .
H11O H -0.042149 1.104222 0.703767 0.044 Uiso 1 1 calc R U . . .
O2S O -0.4590(4) 0.7415(2) 0.91610(16) 0.0303(6) Uani 1 1 d . . . . .
O13 O -0.4487(4) 0.8407(2) 0.56440(16) 0.0286(6) Uani 1 1 d . . . . .
O3S O -0.7847(3) 0.76126(18) 0.99752(14) 0.0219(5) Uani 1 1 d . . . . .
O1S O -0.5540(4) 0.6471(2) 1.05386(17) 0.0346(6) Uani 1 1 d . . . . .
O23 O -0.1125(4) 0.3235(2) 0.55518(16) 0.0292(6) Uani 1 1 d . . . . .
O22 O -0.9535(4) 0.77261(19) 0.75095(16) 0.0277(6) Uani 1 1 d . . . . .
O12 O 0.1609(4) 1.2803(2) 0.76941(16) 0.0295(6) Uani 1 1 d . . . . .
N23 N -1.0465(4) 1.0771(2) 0.91938(17) 0.0220(6) Uani 1 1 d . . . . .
H23N H -1.091926 1.131870 0.944341 0.026 Uiso 1 1 calc R U . . .
O21 O -0.6492(4) 0.5289(2) 0.66428(18) 0.0353(6) Uani 1 1 d . . . . .
H21O H -0.679228 0.580284 0.691281 0.053 Uiso 1 1 calc R U . . .
O4S O -0.5074(4) 0.8387(2) 1.03875(19) 0.0389(7) Uani 1 1 d . . . . .
N21 N -0.5911(4) 0.6934(2) 0.73982(17) 0.0226(6) Uani 1 1 d . . . . .
N13 N 0.1020(4) 1.5984(2) 0.92404(17) 0.0208(6) Uani 1 1 d . . . . .
H13N H 0.123008 1.652894 0.949049 0.025 Uiso 1 1 calc R U . . .
N22 N -0.6539(4) 0.7800(2) 0.78460(17) 0.0221(6) Uani 1 1 d . . . . .
H22N H -0.577517 0.811913 0.809703 0.026 Uiso 1 1 calc R U . . .
N12 N -0.1689(4) 1.3022(2) 0.79479(17) 0.0215(6) Uani 1 1 d . . . . .
H12N H -0.268692 1.337828 0.817215 0.026 Uiso 1 1 calc R U . . .
C19 C 0.0351(5) 1.4254(3) 0.84533(19) 0.0191(7) Uani 1 1 d . . . . .
C13 C -0.2542(5) 0.9488(3) 0.6233(2) 0.0248(7) Uani 1 1 d . . . . .
H13 H -0.151485 0.902268 0.607675 0.030 Uiso 1 1 calc R U . . .
N11 N -0.1890(4) 1.2157(2) 0.75191(17) 0.0225(6) Uani 1 1 d . . . . .
C110 C -0.1055(5) 1.5046(3) 0.8594(2) 0.0212(7) Uani 1 1 d . . . . .
H110 H -0.223780 1.499188 0.842086 0.025 Uiso 1 1 calc R U . . .
C17 C -0.3576(5) 1.1958(3) 0.7359(2) 0.0216(7) Uani 1 1 d . . . . .
H17 H -0.463934 1.239193 0.753700 0.026 Uiso 1 1 calc R U . . .
C11 C -0.3810(5) 1.1059(3) 0.6904(2) 0.0206(7) Uani 1 1 d . . . . .
C26 C -0.1263(5) 0.5693(3) 0.6592(2) 0.0213(7) Uani 1 1 d . . . . .
H26 H -0.042261 0.616809 0.675071 0.026 Uiso 1 1 calc R U . . .
C112 C 0.2413(5) 1.5241(3) 0.9115(2) 0.0232(7) Uani 1 1 d . . . . .
H112 H 0.357980 1.531632 0.929780 0.028 Uiso 1 1 calc R U . . .
C29 C -0.9046(5) 0.9050(3) 0.83754(19) 0.0189(7) Uani 1 1 d . . . . .
C25 C -0.0475(5) 0.4832(3) 0.6179(2) 0.0218(7) Uani 1 1 d . . . . .
H25 H 0.087319 0.472536 0.606496 0.026 Uiso 1 1 calc R U . . .
C21 C -0.3290(5) 0.5874(3) 0.6781(2) 0.0204(7) Uani 1 1 d . . . . .
C211 C -0.8521(5) 1.0678(3) 0.8952(2) 0.0221(7) Uani 1 1 d . . . . .
H211 H -0.768213 1.119445 0.905999 0.027 Uiso 1 1 calc R U . . .
C210 C -0.7766(5) 0.9807(3) 0.8541(2) 0.0207(7) Uani 1 1 d . . . . .
H210 H -0.641591 0.972907 0.837625 0.025 Uiso 1 1 calc R U . . .
C18 C 0.0153(5) 1.3284(3) 0.7999(2) 0.0215(7) Uani 1 1 d . . . . .
C23 C -0.3738(5) 0.4288(3) 0.6091(2) 0.0272(8) Uani 1 1 d . . . . .
H23 H -0.456278 0.381707 0.591917 0.033 Uiso 1 1 calc R U . . .
C15 C -0.5907(5) 1.0000(3) 0.6265(2) 0.0231(7) Uani 1 1 d . . . . .
H15 H -0.711433 0.989157 0.612491 0.028 Uiso 1 1 calc R U . . .
C111 C -0.0677(5) 1.5914(3) 0.8994(2) 0.0213(7) Uani 1 1 d . . . . .
H111 H -0.160579 1.644850 0.909032 0.026 Uiso 1 1 calc R U . . .
C14 C -0.4367(5) 0.9300(3) 0.6046(2) 0.0230(7) Uani 1 1 d . . . . .
C12 C -0.2246(5) 1.0353(3) 0.6646(2) 0.0234(7) Uani 1 1 d . . . . .
C28 C -0.8407(5) 0.8116(3) 0.7868(2) 0.0203(7) Uani 1 1 d . . . . .
C212 C -1.1734(5) 1.0039(3) 0.9061(2) 0.0253(8) Uani 1 1 d . . . . .
H212 H -1.307594 1.012050 0.924867 0.030 Uiso 1 1 calc R U . . .
C213 C -1.1041(5) 0.9172(3) 0.8647(2) 0.0241(7) Uani 1 1 d . . . . .
H213 H -1.191460 0.866676 0.855015 0.029 Uiso 1 1 calc R U . . .
C27 C -0.4057(5) 0.6767(3) 0.7239(2) 0.0213(7) Uani 1 1 d . . . . .
H27 H -0.320805 0.721799 0.741735 0.026 Uiso 1 1 calc R U . . .
C214 C 0.0915(6) 0.2966(3) 0.5451(2) 0.0332(9) Uani 1 1 d . . . . .
H216 H 0.115079 0.232497 0.517327 0.050 Uiso 1 1 calc R U . . .
H215 H 0.170024 0.354355 0.511917 0.050 Uiso 1 1 calc R U . . .
H214 H 0.125623 0.285007 0.599277 0.050 Uiso 1 1 calc R U . . .
C113 C 0.2108(5) 1.4367(3) 0.8715(2) 0.0232(7) Uani 1 1 d . . . . .
H113 H 0.307493 1.385131 0.861950 0.028 Uiso 1 1 calc R U . . .
C22 C -0.4526(5) 0.5158(3) 0.6508(2) 0.0244(7) Uani 1 1 d . . . . .
C24 C -0.1741(5) 0.4123(3) 0.5934(2) 0.0230(7) Uani 1 1 d . . . . .
C16 C -0.5616(5) 1.0855(3) 0.6690(2) 0.0212(7) Uani 1 1 d . . . . .
H16 H -0.665345 1.131560 0.684294 0.025 Uiso 1 1 calc R U . . .
C114 C -0.6346(6) 0.8140(3) 0.5476(2) 0.0327(9) Uani 1 1 d . . . . .
H114 H -0.623048 0.750106 0.519397 0.049 Uiso 1 1 calc R U . . .
H115 H -0.728907 0.802096 0.599592 0.049 Uiso 1 1 calc R U . . .
H116 H -0.676993 0.871941 0.512580 0.049 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
S1 O4S 1.452(3) . ?
S1 O2S 1.462(3) . ?
S1 O1S 1.466(3) . ?
S1 O3S 1.521(2) . ?
O11 C12 1.352(4) . ?
O13 C14 1.367(4) . ?
O13 C114 1.427(4) . ?
O23 C24 1.355(4) . ?
O23 C214 1.437(4) . ?
O22 C28 1.207(4) . ?
O12 C18 1.217(4) . ?
N23 C211 1.337(4) . ?
N23 C212 1.343(5) . ?
O21 C22 1.352(4) . ?
N21 C27 1.284(4) . ?
N21 N22 1.389(4) . ?
N13 C111 1.331(4) . ?
N13 C112 1.338(4) . ?
N22 C28 1.350(4) . ?
N12 C18 1.348(4) . ?
N12 N11 1.374(4) . ?
C19 C113 1.390(5) . ?
C19 C110 1.391(5) . ?
C19 C18 1.511(4) . ?
C13 C12 1.374(5) . ?
C13 C14 1.394(5) . ?
N11 C17 1.286(4) . ?
C110 C111 1.378(5) . ?
C17 C11 1.442(5) . ?
C11 C16 1.404(5) . ?
C11 C12 1.421(5) . ?
C26 C25 1.383(5) . ?
C26 C21 1.403(5) . ?
C112 C113 1.372(5) . ?
C29 C213 1.381(5) . ?
C29 C210 1.392(5) . ?
C29 C28 1.514(4) . ?
C25 C24 1.400(5) . ?
C21 C22 1.415(5) . ?
C21 C27 1.448(5) . ?
C211 C210 1.384(5) . ?
C23 C24 1.379(5) . ?
C23 C22 1.394(5) . ?
C15 C16 1.375(5) . ?
C15 C14 1.392(5) . ?
C212 C213 1.371(5) . ?

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
O4S S1 O2S 112.06(17) . . ?
O4S S1 O1S 111.22(17) . . ?
O2S S1 O1S 110.12(16) . . ?
O4S S1 O3S 108.66(14) . . ?
O2S S1 O3S 107.55(14) . . ?
O1S S1 O3S 107.03(15) . . ?
C14 O13 C114 117.9(3) . . ?
C24 O23 C214 118.0(3) . . ?
C211 N23 C212 122.4(3) . . ?
C27 N21 N22 116.5(3) . . ?
C111 N13 C112 122.7(3) . . ?
C28 N22 N21 116.8(3) . . ?
C18 N12 N11 116.5(3) . . ?
C113 C19 C110 118.7(3) . . ?
C113 C19 C18 116.5(3) . . ?
C110 C19 C18 124.7(3) . . ?
C12 C13 C14 120.7(3) . . ?
C17 N11 N12 118.9(3) . . ?
C111 C110 C19 119.3(3) . . ?
N11 C17 C11 119.7(3) . . ?
C16 C11 C12 117.3(3) . . ?
C16 C11 C17 120.6(3) . . ?
C12 C11 C17 122.1(3) . . ?
C25 C26 C21 122.1(3) . . ?
N13 C112 C113 119.5(3) . . ?
C213 C29 C210 119.0(3) . . ?
C213 C29 C28 116.7(3) . . ?
C210 C29 C28 124.2(3) . . ?
C26 C25 C24 118.9(3) . . ?
C26 C21 C22 117.6(3) . . ?
C26 C21 C27 120.3(3) . . ?
C22 C21 C27 122.1(3) . . ?
N23 C211 C210 119.5(3) . . ?
C211 C210 C29 119.4(3) . . ?
O12 C18 N12 124.2(3) . . ?
O12 C18 C19 120.0(3) . . ?
N12 C18 C19 115.8(3) . . ?
C24 C23 C22 120.3(3) . . ?
C16 C15 C14 119.0(3) . . ?
N13 C111 C110 119.9(3) . . ?
O13 C14 C15 124.5(3) . . ?
O13 C14 C13 115.3(3) . . ?
C15 C14 C13 120.2(3) . . ?
O11 C12 C13 117.8(3) . . ?
O11 C12 C11 121.8(3) . . ?
C13 C12 C11 120.3(3) . . ?
O22 C28 N22 124.9(3) . . ?
O22 C28 C29 119.8(3) . . ?
N22 C28 C29 115.2(3) . . ?
N23 C212 C213 119.7(3) . . ?
C212 C213 C29 120.0(3) . . ?
N21 C27 C21 119.7(3) . . ?
C112 C113 C19 119.9(3) . . ?
O21 C22 C23 118.0(3) . . ?
O21 C22 C21 121.5(3) . . ?
C23 C22 C21 120.4(3) . . ?
O23 C24 C23 115.8(3) . . ?
O23 C24 C25 123.5(3) . . ?
C23 C24 C25 120.6(3) . . ?
C15 C16 C11 122.5(3) . . ?

_refine_diff_density_max         0.491
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.068

# start Validation Reply Form
_vrf_PLAT910_shelx               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 25 Note
RESPONSE: These reflections were cut off by the beamstop
;
# end Validation Reply Form
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1589827'
_audit_update_record             
;
2018-05-22 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 Br N3 O4'
_chemical_formula_weight         384.23

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'

_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                   13.3678(9)
_cell_length_b                   7.6361(5)
_cell_length_c                   16.4545(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.019(7)
_cell_angle_gamma                90
_cell_volume                     1663.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1439
_cell_measurement_theta_min      4.3890
_cell_measurement_theta_max      22.2990

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    2.495
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97870
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11229
_diffrn_reflns_av_unetI/netI     0.0968
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.102
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2913
_reflns_number_gt                2068
_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       'CrysAlis CCD (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS (Sheldrick, 1990, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0136P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2913
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.0796
_refine_ls_wR_factor_gt          0.0704
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
Br Br 0.47978(3) 0.29612(5) 0.76371(3) 0.02699(15) Uani 1 1 d . . . . .
O1 O 0.2969(2) 0.4519(4) 0.37758(19) 0.0271(8) Uani 1 1 d . . . . .
H1 H 0.346507 0.408408 0.405220 0.041 Uiso 1 1 calc R U . . .
O3 O 0.1330(2) 0.6050(3) 0.3069(2) 0.0265(8) Uani 1 1 d . . . . .
N2 N 0.4946(2) 0.2774(4) 0.5543(2) 0.0236(9) Uani 1 1 d . . . . .
H2 H 0.508419 0.284440 0.606813 0.028 Uiso 1 1 calc R U . . .
O2 O 0.5395(2) 0.1826(4) 0.4345(2) 0.0314(8) Uani 1 1 d . . . . .
C3 C 0.1440(3) 0.5989(5) 0.3903(3) 0.0210(11) Uani 1 1 d . . . . .
N1 N 0.4093(3) 0.3537(4) 0.5129(2) 0.0211(9) Uani 1 1 d . . . . .
C10 C 0.7143(3) 0.0260(5) 0.5087(3) 0.0239(12) Uani 1 1 d . . . . .
H10 H 0.700666 0.030486 0.451705 0.029 Uiso 1 1 calc R U . . .
N3 N 0.8179(3) -0.0629(4) 0.6281(3) 0.0260(10) Uani 1 1 d . . . . .
H3 H 0.871783 -0.114576 0.650866 0.031 Uiso 1 1 calc R U . . .
C1 C 0.2552(3) 0.5107(5) 0.5138(3) 0.0224(11) Uani 1 1 d . . . . .
C13 C 0.6696(3) 0.0913(5) 0.6402(3) 0.0226(11) Uani 1 1 d . . . . .
H13 H 0.625608 0.140668 0.672947 0.027 Uiso 1 1 calc R U . . .
C9 C 0.6483(3) 0.1023(5) 0.5563(3) 0.0193(11) Uani 1 1 d . . . . .
C7 C 0.3483(3) 0.4312(5) 0.5549(3) 0.0257(12) Uani 1 1 d . . . . .
H7 H 0.363393 0.436691 0.611800 0.031 Uiso 1 1 calc R U . . .
C5 C 0.0976(3) 0.6598(5) 0.5239(3) 0.0266(12) Uani 1 1 d . . . . .
H5 H 0.051853 0.706638 0.555680 0.032 Uiso 1 1 calc R U . . .
C2 C 0.2336(3) 0.5188(5) 0.4284(3) 0.0195(11) Uani 1 1 d . . . . .
C12 C 0.7561(3) 0.0071(5) 0.6763(3) 0.0238(11) Uani 1 1 d . . . . .
H12 H 0.771011 -0.000553 0.733115 0.029 Uiso 1 1 calc R U . . .
C6 C 0.1862(3) 0.5845(5) 0.5617(3) 0.0244(12) Uani 1 1 d . . . . .
H6 H 0.200238 0.582519 0.618665 0.029 Uiso 1 1 calc R U . . .
C4 C 0.0765(3) 0.6659(5) 0.4389(3) 0.0228(12) Uani 1 1 d . . . . .
H4 H 0.016282 0.715661 0.414319 0.027 Uiso 1 1 calc R U . . .
C8 C 0.5564(3) 0.1902(5) 0.5089(3) 0.0220(11) Uani 1 1 d . . . . .
C11 C 0.8004(3) -0.0567(5) 0.5464(3) 0.0252(12) Uani 1 1 d . . . . .
H11 H 0.845527 -0.107479 0.515142 0.030 Uiso 1 1 calc R U . . .
C14 C 0.0401(3) 0.6784(5) 0.2656(3) 0.0318(12) Uani 1 1 d . . . . .
H14C H 0.040774 0.675921 0.207403 0.048 Uiso 1 1 calc R U . . .
H14A H -0.016070 0.610988 0.278920 0.048 Uiso 1 1 calc R U . . .
H14B H 0.033635 0.797306 0.283214 0.048 Uiso 1 1 calc R U . . .
O4 O 0.8609(3) 0.9191(4) 0.3695(2) 0.0402(9) Uani 1 1 d . . . . .
H4O H 0.892621 0.999890 0.352483 0.060 Uiso 1 1 calc R U . . .
C15 C 0.7891(4) 0.8572(6) 0.3061(4) 0.0513(16) Uani 1 1 d . . . . .
H15A H 0.758196 0.752964 0.323841 0.077 Uiso 1 1 calc R U . . .
H15B H 0.821377 0.830958 0.259005 0.077 Uiso 1 1 calc R U . . .
H15C H 0.738242 0.945043 0.292023 0.077 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
O1 C2 1.369(5) . ?
O3 C3 1.360(5) . ?
O3 C14 1.443(4) . ?
N2 C8 1.363(5) . ?
N2 N1 1.373(4) . ?
O2 C8 1.215(5) . ?
C3 C4 1.385(6) . ?
C3 C2 1.411(6) . ?
N1 C7 1.285(5) . ?
C10 C11 1.382(5) . ?
C10 C9 1.388(6) . ?
N3 C11 1.333(6) . ?
N3 C12 1.334(5) . ?
C1 C2 1.396(6) . ?
C1 C6 1.413(6) . ?
C1 C7 1.463(5) . ?
C13 C9 1.374(6) . ?
C13 C12 1.383(5) . ?
C9 C8 1.516(6) . ?
C5 C6 1.383(5) . ?
C5 C4 1.389(6) . ?
O4 C15 1.398(5) . ?

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
C3 O3 C14 116.9(3) . . ?
C8 N2 N1 117.4(4) . . ?
O3 C3 C4 125.6(4) . . ?
O3 C3 C2 115.4(4) . . ?
C4 C3 C2 119.0(5) . . ?
C7 N1 N2 118.2(4) . . ?
C11 C10 C9 119.6(5) . . ?
C11 N3 C12 123.3(4) . . ?
C2 C1 C6 119.0(4) . . ?
C2 C1 C7 121.9(4) . . ?
C6 C1 C7 119.1(5) . . ?
C9 C13 C12 120.2(5) . . ?
C13 C9 C10 118.9(4) . . ?
C13 C9 C8 125.7(4) . . ?
C10 C9 C8 115.4(4) . . ?
N1 C7 C1 120.3(5) . . ?
C6 C5 C4 120.5(4) . . ?
O1 C2 C1 122.6(4) . . ?
O1 C2 C3 116.7(4) . . ?
C1 C2 C3 120.7(4) . . ?
N3 C12 C13 118.8(5) . . ?
C5 C6 C1 120.0(5) . . ?
C3 C4 C5 120.8(4) . . ?
O2 C8 N2 122.3(4) . . ?
O2 C8 C9 121.4(4) . . ?
N2 C8 C9 116.3(4) . . ?
N3 C11 C10 119.2(4) . . ?

_refine_diff_density_max         0.682
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.096

# start Validation Reply Form
_vrf_PLAT910_shelx               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 11 Note
RESPONSE: These reflections were cut off by the beamstop
;
# end Validation Reply Form
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1589826'
_audit_update_record             
;
2018-05-22 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H26 Br1 N6 O6'
_chemical_formula_weight         622.45

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.1019(9)
_cell_length_b                   13.0795(4)
_cell_length_c                   12.6107(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.281(4)
_cell_angle_gamma                90
_cell_volume                     2791.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1834
_cell_measurement_theta_min      4.3890
_cell_measurement_theta_max      26.4750

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_F_000             1276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    1.526
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86939
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   0.86939
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7189
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.128
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2448
_reflns_number_gt                1988
_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       'CrysAlis CCD (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS (Sheldrick, 1990, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0399P)²+0.6786P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2448
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
Br Br 0.500000 0.03458(3) 0.250000 0.06039(18) Uani 1 2 d S T P . .
O3 O 0.72540(12) 0.28059(16) 0.86881(13) 0.0640(5) Uani 1 1 d . . . . .
O1 O 0.67166(13) 0.40909(14) 0.51347(13) 0.0605(5) Uani 1 1 d . . . . .
H1 H 0.656531 0.389907 0.452035 0.091 Uiso 1 1 calc R U . . .
N2 N 0.60208(11) 0.25707(17) 0.25771(14) 0.0448(5) Uani 1 1 d . . . . .
H2N H 0.594208 0.195046 0.236148 0.054 Uiso 1 1 calc R U . . .
O2 O 0.60417(14) 0.42452(16) 0.21733(14) 0.0747(6) Uani 1 1 d . . . . .
N3 N 0.52440(12) 0.28133(17) -0.14383(15) 0.0474(5) Uani 1 1 d . . . . .
H3N H 0.510341 0.272309 -0.211441 0.057 Uiso 0.5 1 calc R U P . .
N1 N 0.62503(11) 0.28006(17) 0.36415(14) 0.0450(5) Uani 1 1 d . . . . .
C1 C 0.65860(13) 0.22907(19) 0.54382(18) 0.0401(6) Uani 1 1 d . . . . .
C12 C 0.53232(14) 0.2026(2) -0.07826(18) 0.0483(6) Uani 1 1 d . . . . .
H12 H 0.522961 0.137141 -0.106102 0.058 Uiso 1 1 calc R U . . .
C8 C 0.59256(14) 0.3363(2) 0.18907(19) 0.0463(6) Uani 1 1 d . . . . .
C9 C 0.56839(13) 0.3109(2) 0.07246(17) 0.0402(6) Uani 1 1 d . . . . .
C3 C 0.69707(15) 0.3489(2) 0.68910(18) 0.0478(6) Uani 1 1 d . . . . .
H3 H 0.707181 0.415568 0.712769 0.057 Uiso 0.5 1 calc R U P . .
C5 C 0.68678(16) 0.1701(2) 0.72694(19) 0.0545(7) Uani 1 1 d . . . . .
H5 H 0.690220 0.116780 0.776147 0.065 Uiso 1 1 calc R U . . .
C2 C 0.67527(14) 0.3283(2) 0.58070(18) 0.0426(6) Uani 1 1 d . . . . .
C6 C 0.66502(15) 0.1513(2) 0.61965(19) 0.0508(7) Uani 1 1 d . . . . .
H6 H 0.654241 0.084436 0.597022 0.061 Uiso 1 1 calc R U . . .
C13 C 0.55417(15) 0.2144(2) 0.03080(18) 0.0472(6) Uani 1 1 d . . . . .
H13 H 0.559212 0.157679 0.075668 0.057 Uiso 1 1 calc R U . . .
C4 C 0.70345(15) 0.2688(2) 0.76094(18) 0.0477(6) Uani 1 1 d . . . . .
C14 C 0.7481(2) 0.3801(3) 0.9074(2) 0.0769(10) Uani 1 1 d . . . . .
H14C H 0.762035 0.378088 0.983844 0.115 Uiso 1 1 calc R U . . .
H14B H 0.792720 0.402838 0.875387 0.115 Uiso 1 1 calc R U . . .
H14A H 0.704844 0.426630 0.888837 0.115 Uiso 1 1 calc R U . . .
C7 C 0.63490(13) 0.2064(2) 0.43130(18) 0.0441(6) Uani 1 1 d . . . . .
H7 H 0.626983 0.139200 0.408270 0.053 Uiso 1 1 calc R U . . .
C11 C 0.53827(18) 0.3748(2) -0.1047(2) 0.0632(8) Uani 1 1 d . . . . .
H11 H 0.532722 0.430191 -0.151412 0.076 Uiso 1 1 calc R U . . .
C10 C 0.56052(17) 0.3917(2) 0.00234(19) 0.0594(8) Uani 1 1 d . . . . .
H10 H 0.570310 0.457978 0.027636 0.071 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
O3 C4 1.367(3) . ?
O3 C14 1.424(4) . ?
O1 C2 1.351(3) . ?
N2 C8 1.345(3) . ?
N2 N1 1.376(2) . ?
O2 C8 1.216(3) . ?
N3 C12 1.316(3) . ?
N3 C11 1.326(3) . ?
N1 C7 1.277(3) . ?
C1 C6 1.390(3) . ?
C1 C2 1.394(3) . ?
C1 C7 1.449(3) . ?
C12 C13 1.381(3) . ?
C8 C9 1.506(3) . ?
C9 C10 1.373(3) . ?
C9 C13 1.374(3) . ?
C3 C4 1.379(4) . ?
C3 C2 1.391(3) . ?
C5 C6 1.373(3) . ?
C5 C4 1.377(4) . ?
C11 C10 1.367(3) . ?

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
C4 O3 C14 117.7(2) . . ?
C8 N2 N1 116.8(2) . . ?
C12 N3 C11 119.4(2) . . ?
C7 N1 N2 118.3(2) . . ?
C6 C1 C2 117.4(2) . . ?
C6 C1 C7 120.5(2) . . ?
C2 C1 C7 122.1(2) . . ?
N3 C12 C13 121.8(2) . . ?
O2 C8 N2 122.9(2) . . ?
O2 C8 C9 120.4(2) . . ?
N2 C8 C9 116.7(2) . . ?
C10 C9 C13 117.7(2) . . ?
C10 C9 C8 116.5(2) . . ?
C13 C9 C8 125.7(2) . . ?
C4 C3 C2 118.9(2) . . ?
C6 C5 C4 119.3(2) . . ?
O1 C2 C3 116.6(2) . . ?
O1 C2 C1 122.0(2) . . ?
C3 C2 C1 121.4(2) . . ?
C5 C6 C1 122.0(2) . . ?
C9 C13 C12 119.4(2) . . ?
O3 C4 C5 115.5(2) . . ?
O3 C4 C3 123.5(2) . . ?
C5 C4 C3 120.9(2) . . ?
N1 C7 C1 119.1(2) . . ?
N3 C11 C10 121.7(3) . . ?
C11 C10 C9 119.9(3) . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.048

# start Validation Reply Form
_vrf_PLAT910_shelx               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 13 Note
RESPONSE: These reflections were cut off by the beamstop
;
# end Validation Reply Form
####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1589825'
_audit_update_record             
;
2018-05-22 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Cl N3 O3'
_chemical_formula_weight         307.73

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.4513(4)
_cell_length_b                   8.2008(4)
_cell_length_c                   11.4644(6)
_cell_angle_alpha                92.499(4)
_cell_angle_beta                 95.861(4)
_cell_angle_gamma                96.295(4)
_cell_volume                     691.62(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7524
_cell_measurement_theta_min      3.8492
_cell_measurement_theta_max      30.5648

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.290
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93547
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10598
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.869
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3614
_reflns_number_gt                3098
_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       'CrysAlis CCD (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS (Sheldrick, 1990, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0757P)²+0.1936P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3614
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1285
_refine_ls_wR_factor_gt          0.1242
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
O1 O 0.05887(19) 0.52449(15) 0.35810(11) 0.0497(3) Uani 1 1 d . . . . .
H1 H 0.089594 0.616433 0.389620 0.075 Uiso 1 1 d R U . . .
O2 O 0.2415(2) 0.88403(16) 0.60029(12) 0.0612(4) Uani 1 1 d . . . . .
O3 O -0.28943(19) 0.27404(15) 0.01118(11) 0.0493(3) Uani 1 1 d . . . . .
N1 N 0.11709(17) 0.84185(15) 0.37142(11) 0.0357(3) Uani 1 1 d . . . . .
N2 N 0.19362(18) 0.99160(16) 0.42305(11) 0.0358(3) Uani 1 1 d . . . . .
H2 H 0.203082 1.077615 0.382796 0.043 Uiso 1 1 d R U . . .
N3 N 0.48070(19) 1.46253(17) 0.69162(12) 0.0412(3) Uani 1 1 d . . . . .
H3A H 0.527841 1.556017 0.724107 0.049 Uiso 1 1 d R U . . .
C1 C -0.04284(19) 0.69234(18) 0.20442(13) 0.0320(3) Uani 1 1 d . . . . .
C2 C -0.03027(19) 0.53809(18) 0.25080(12) 0.0316(3) Uani 1 1 d . . . . .
C3 C -0.1120(2) 0.39495(18) 0.18883(13) 0.0356(3) Uani 1 1 d . . . . .
H3 H -0.102265 0.293160 0.220114 0.043 Uiso 1 1 calc R U . . .
C4 C -0.2079(2) 0.40579(19) 0.08035(13) 0.0353(3) Uani 1 1 d . . . . .
C5 C -0.2251(2) 0.5577(2) 0.03349(14) 0.0422(4) Uani 1 1 d . . . . .
H5 H -0.292538 0.564140 -0.038672 0.051 Uiso 1 1 calc R U . . .
C6 C -0.1421(2) 0.69699(19) 0.09424(14) 0.0397(3) Uani 1 1 d . . . . .
H6 H -0.151710 0.797941 0.061619 0.048 Uiso 1 1 calc R U . . .
C7 C 0.0397(2) 0.84275(19) 0.26627(13) 0.0353(3) Uani 1 1 d . . . . .
H7 H 0.036926 0.941563 0.229648 0.042 Uiso 1 1 calc R U . . .
C8 C 0.2534(2) 0.99941(18) 0.53783(13) 0.0350(3) Uani 1 1 d . . . . .
C9 C 0.33506(19) 1.16770(18) 0.58715(12) 0.0308(3) Uani 1 1 d . . . . .
C10 C 0.4573(2) 1.1749(2) 0.68766(13) 0.0371(3) Uani 1 1 d . . . . .
H10 H 0.489090 1.079074 0.720559 0.044 Uiso 1 1 calc R U . . .
C11 C 0.5305(2) 1.3263(2) 0.73780(15) 0.0423(4) Uani 1 1 d . . . . .
H11 H 0.614843 1.333336 0.803990 0.051 Uiso 1 1 calc R U . . .
C12 C 0.3609(2) 1.45973(19) 0.59716(15) 0.0399(3) Uani 1 1 d . . . . .
H12 H 0.327433 1.557701 0.568614 0.048 Uiso 1 1 calc R U . . .
C13 C 0.2861(2) 1.31202(19) 0.54145(13) 0.0358(3) Uani 1 1 d . . . . .
H13 H 0.204243 1.309259 0.474304 0.043 Uiso 1 1 calc R U . . .
C14 C -0.2632(3) 0.1157(2) 0.0505(2) 0.0590(5) Uani 1 1 d . . . . .
H14A H -0.135644 0.108379 0.067919 0.088 Uiso 1 1 calc R U . . .
H14B H -0.313449 0.033669 -0.009784 0.088 Uiso 1 1 calc R U . . .
H14C H -0.322815 0.097865 0.120023 0.088 Uiso 1 1 calc R U . . .
Cl Cl 0.66865(6) 0.79559(4) 0.77895(3) 0.04359(14) Uani 1 1 d . . . . .


_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
O1 C2 1.3521(17) . ?
O1 H1 0.8203 . ?
O2 C8 1.2122(19) . ?
O3 C4 1.3595(18) . ?
O3 C14 1.420(2) . ?
N1 C7 1.2828(19) . ?
N1 N2 1.3776(17) . ?
N2 C8 1.3420(19) . ?
N2 H2 0.8600 . ?
N3 C12 1.329(2) . ?
N3 C11 1.330(2) . ?
N3 H3A 0.8598 . ?
C1 C6 1.401(2) . ?
C1 C2 1.402(2) . ?
C1 C7 1.439(2) . ?
C2 C3 1.391(2) . ?
C3 C4 1.381(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(2) . ?
C5 C6 1.364(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.507(2) . ?
C9 C13 1.385(2) . ?
C9 C10 1.389(2) . ?
C10 C11 1.376(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.377(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C2 O1 H1 109.4 . . ?
C4 O3 C14 117.24(13) . . ?
C7 N1 N2 116.43(13) . . ?
C8 N2 N1 118.14(13) . . ?
C8 N2 H2 120.9 . . ?
N1 N2 H2 120.9 . . ?
C12 N3 C11 122.53(14) . . ?
C12 N3 H3A 118.7 . . ?
C11 N3 H3A 118.7 . . ?
C6 C1 C2 117.61(13) . . ?
C6 C1 C7 119.94(13) . . ?
C2 C1 C7 122.45(13) . . ?
O1 C2 C3 118.08(13) . . ?
O1 C2 C1 120.89(13) . . ?
C3 C2 C1 121.02(13) . . ?
C4 C3 C2 119.24(13) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
O3 C4 C3 124.19(14) . . ?
O3 C4 C5 115.02(13) . . ?
C3 C4 C5 120.78(14) . . ?
C6 C5 C4 119.47(14) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 121.87(14) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
N1 C7 C1 120.64(14) . . ?
N1 C7 H7 119.7 . . ?
C1 C7 H7 119.7 . . ?
O2 C8 N2 124.47(14) . . ?
O2 C8 C9 120.87(14) . . ?
N2 C8 C9 114.65(13) . . ?
C13 C9 C10 119.53(14) . . ?
C13 C9 C8 123.34(13) . . ?
C10 C9 C8 117.01(13) . . ?
C11 C10 C9 118.90(15) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N3 C11 C10 120.01(15) . . ?
N3 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
N3 C12 C13 120.14(15) . . ?
N3 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C9 118.85(14) . . ?
C12 C13 H13 120.6 . . ?
C9 C13 H13 120.6 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.888
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1589824'
_audit_update_record             
;
2018-05-22 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Br N3 O3'
_chemical_formula_weight         352.19

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.4259(3)
_cell_length_b                   8.4044(3)
_cell_length_c                   11.6532(4)
_cell_angle_alpha                92.717(3)
_cell_angle_beta                 96.841(3)
_cell_angle_gamma                96.491(3)
_cell_volume                     716.10(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10124
_cell_measurement_theta_min      4.4750
_cell_measurement_theta_max      32.2740

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    2.884
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24039
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.212
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3784
_reflns_number_gt                3450
_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       'CrysAlis CCD (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS (Sheldrick, 1990, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0324P)²+0.2476P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3784
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0667
_refine_ls_wR_factor_gt          0.0650
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
C1 C 0.4575(2) 0.18801(19) 0.20994(13) 0.0322(3) Uani 1 1 d . . . . .
C2 C 0.4719(2) 0.0380(2) 0.25618(13) 0.0321(3) Uani 1 1 d . . . . .
C3 C 0.3924(2) -0.1034(2) 0.19485(14) 0.0356(3) Uani 1 1 d . . . . .
H3 H 0.402634 -0.201967 0.226565 0.043 Uiso 1 1 calc R U . . .
C4 C 0.2977(2) -0.0954(2) 0.08555(14) 0.0352(3) Uani 1 1 d . . . . .
C5 C 0.2778(3) 0.0524(2) 0.03895(14) 0.0423(4) Uani 1 1 d . . . . .
H5 H 0.210130 0.056980 -0.033034 0.051 Uiso 1 1 calc R U . . .
C6 C 0.3585(3) 0.1906(2) 0.09968(14) 0.0400(4) Uani 1 1 d . . . . .
H6 H 0.347531 0.288500 0.067190 0.048 Uiso 1 1 calc R U . . .
C7 C 0.5388(2) 0.3369(2) 0.27114(14) 0.0360(3) Uani 1 1 d . . . . .
H7 H 0.533902 0.432704 0.234746 0.043 Uiso 1 1 calc R U . . .
C8 C 0.7501(2) 0.4972(2) 0.54096(15) 0.0368(3) Uani 1 1 d . . . . .
C9 C 0.8334(2) 0.66191(19) 0.58969(13) 0.0321(3) Uani 1 1 d . . . . .
C10 C 0.9534(2) 0.6704(2) 0.69140(15) 0.0389(4) Uani 1 1 d . . . . .
H10 H 0.983074 0.577166 0.725078 0.047 Uiso 1 1 calc R U . . .
C11 C 1.0276(3) 0.8180(2) 0.74170(16) 0.0451(4) Uani 1 1 d . . . . .
H11 H 1.110641 0.825286 0.808639 0.054 Uiso 1 1 calc R U . . .
C12 C 0.8624(3) 0.9478(2) 0.59818(16) 0.0423(4) Uani 1 1 d . . . . .
H12 H 0.830874 1.043327 0.568881 0.051 Uiso 1 1 calc R U . . .
C13 C 0.7872(3) 0.8033(2) 0.54221(15) 0.0375(4) Uani 1 1 d . . . . .
H13 H 0.707196 0.800002 0.474126 0.045 Uiso 1 1 calc R U . . .
C14 C 0.2481(4) -0.3805(2) 0.0562(2) 0.0561(5) Uani 1 1 d . . . . .
H14A H 0.186523 -0.461859 -0.000072 0.084 Uiso 1 1 calc R U . . .
H14B H 0.376448 -0.390222 0.066580 0.084 Uiso 1 1 calc R U . . .
H14C H 0.200027 -0.393242 0.128527 0.084 Uiso 1 1 calc R U . . .
N1 N 0.6179(2) 0.33831(17) 0.37556(12) 0.0370(3) Uani 1 1 d . . . . .
N2 N 0.6940(2) 0.48629(17) 0.42664(12) 0.0374(3) Uani 1 1 d . . . . .
H2N H 0.705150 0.569132 0.386314 0.045 Uiso 1 1 calc R U . . .
N3 N 0.9800(2) 0.95115(19) 0.69409(14) 0.0439(4) Uani 1 1 d . . . . .
HN H 1.027362 1.042703 0.726739 0.053 Uiso 1 1 calc R U . . .
O1 O 0.5619(2) 0.02599(16) 0.36328(11) 0.0489(3) Uani 1 1 d . . . . .
H1O H 0.603378 0.115804 0.391492 0.073 Uiso 1 1 calc R U . . .
O3 O 0.2201(2) -0.22604(16) 0.01668(11) 0.0483(3) Uani 1 1 d . . . . .
Br1 Br 0.82814(3) 0.70194(2) 0.21547(2) 0.04155(7) Uani 1 1 d . . . . .
O2 O 0.7346(3) 0.38609(18) 0.60361(13) 0.0665(5) Uani 1 1 d . . . . .


_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 C2 1.404(2) . ?
C1 C6 1.405(2) . ?
C1 C7 1.442(2) . ?
C2 O1 1.3577(19) . ?
C2 C3 1.390(2) . ?
C3 C4 1.388(2) . ?
C4 O3 1.358(2) . ?
C4 C5 1.395(2) . ?
C5 C6 1.368(2) . ?
C7 N1 1.286(2) . ?
C8 O2 1.216(2) . ?
C8 N2 1.343(2) . ?
C8 C9 1.507(2) . ?
C9 C10 1.389(2) . ?
C9 C13 1.394(2) . ?
C10 C11 1.373(3) . ?
C11 N3 1.337(3) . ?
C12 N3 1.331(3) . ?
C12 C13 1.378(2) . ?
C14 O3 1.426(2) . ?
N1 N2 1.3824(19) . ?

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 C1 C6 117.69(15) . . ?
C2 C1 C7 122.72(15) . . ?
C6 C1 C7 119.59(15) . . ?
O1 C2 C3 117.50(15) . . ?
O1 C2 C1 121.15(15) . . ?
C3 C2 C1 121.34(15) . . ?
C4 C3 C2 119.02(15) . . ?
O3 C4 C3 123.91(15) . . ?
O3 C4 C5 115.40(15) . . ?
C3 C4 C5 120.68(15) . . ?
C6 C5 C4 119.66(15) . . ?
C5 C6 C1 121.57(16) . . ?
N1 C7 C1 120.58(16) . . ?
O2 C8 N2 124.40(16) . . ?
O2 C8 C9 120.68(15) . . ?
N2 C8 C9 114.92(14) . . ?
C10 C9 C13 119.41(16) . . ?
C10 C9 C8 117.05(15) . . ?
C13 C9 C8 123.42(15) . . ?
C11 C10 C9 119.31(17) . . ?
N3 C11 C10 119.74(17) . . ?
N3 C12 C13 120.16(17) . . ?
C12 C13 C9 118.66(17) . . ?
C7 N1 N2 116.47(15) . . ?
C8 N2 N1 118.19(14) . . ?
C12 N3 C11 122.68(16) . . ?
C4 O3 C14 117.80(15) . . ?

_refine_diff_density_max         0.605
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.051

# start Validation Reply Form
_vrf_PLAT910_shelx               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 11 Note
RESPONSE: These reflections were cut off by the beamstop
;
# end Validation Reply Form

####################################################################### 
# 
# 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_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1589830'
_audit_update_record             
;
2018-05-22 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Br N3 O3'
_chemical_formula_weight         352.19

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.4259(3)
_cell_length_b                   8.4044(3)
_cell_length_c                   11.6532(4)
_cell_angle_alpha                92.717(3)
_cell_angle_beta                 96.841(3)
_cell_angle_gamma                96.491(3)
_cell_volume                     716.10(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10124
_cell_measurement_theta_min      4.4750
_cell_measurement_theta_max      32.2740

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    2.884
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24039
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.212
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3784
_reflns_number_gt                3450
_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       'CrysAlis CCD (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS (Sheldrick, 1990, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0324P)²+0.2476P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3784
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0667
_refine_ls_wR_factor_gt          0.0650
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
C1 C 0.4575(2) 0.18801(19) 0.20994(13) 0.0322(3) Uani 1 1 d . . . . .
C2 C 0.4719(2) 0.0380(2) 0.25618(13) 0.0321(3) Uani 1 1 d . . . . .
C3 C 0.3924(2) -0.1034(2) 0.19485(14) 0.0356(3) Uani 1 1 d . . . . .
H3 H 0.402634 -0.201967 0.226565 0.043 Uiso 1 1 calc R U . . .
C4 C 0.2977(2) -0.0954(2) 0.08555(14) 0.0352(3) Uani 1 1 d . . . . .
C5 C 0.2778(3) 0.0524(2) 0.03895(14) 0.0423(4) Uani 1 1 d . . . . .
H5 H 0.210130 0.056980 -0.033034 0.051 Uiso 1 1 calc R U . . .
C6 C 0.3585(3) 0.1906(2) 0.09968(14) 0.0400(4) Uani 1 1 d . . . . .
H6 H 0.347531 0.288500 0.067190 0.048 Uiso 1 1 calc R U . . .
C7 C 0.5388(2) 0.3369(2) 0.27114(14) 0.0360(3) Uani 1 1 d . . . . .
H7 H 0.533902 0.432704 0.234746 0.043 Uiso 1 1 calc R U . . .
C8 C 0.7501(2) 0.4972(2) 0.54096(15) 0.0368(3) Uani 1 1 d . . . . .
C9 C 0.8334(2) 0.66191(19) 0.58969(13) 0.0321(3) Uani 1 1 d . . . . .
C10 C 0.9534(2) 0.6704(2) 0.69140(15) 0.0389(4) Uani 1 1 d . . . . .
H10 H 0.983074 0.577166 0.725078 0.047 Uiso 1 1 calc R U . . .
C11 C 1.0276(3) 0.8180(2) 0.74170(16) 0.0451(4) Uani 1 1 d . . . . .
H11 H 1.110641 0.825286 0.808639 0.054 Uiso 1 1 calc R U . . .
C12 C 0.8624(3) 0.9478(2) 0.59818(16) 0.0423(4) Uani 1 1 d . . . . .
H12 H 0.830874 1.043327 0.568881 0.051 Uiso 1 1 calc R U . . .
C13 C 0.7872(3) 0.8033(2) 0.54221(15) 0.0375(4) Uani 1 1 d . . . . .
H13 H 0.707196 0.800002 0.474126 0.045 Uiso 1 1 calc R U . . .
C14 C 0.2481(4) -0.3805(2) 0.0562(2) 0.0561(5) Uani 1 1 d . . . . .
H14A H 0.186523 -0.461859 -0.000072 0.084 Uiso 1 1 calc R U . . .
H14B H 0.376448 -0.390222 0.066580 0.084 Uiso 1 1 calc R U . . .
H14C H 0.200027 -0.393242 0.128527 0.084 Uiso 1 1 calc R U . . .
N1 N 0.6179(2) 0.33831(17) 0.37556(12) 0.0370(3) Uani 1 1 d . . . . .
N2 N 0.6940(2) 0.48629(17) 0.42664(12) 0.0374(3) Uani 1 1 d . . . . .
H2N H 0.705150 0.569132 0.386314 0.045 Uiso 1 1 calc R U . . .
N3 N 0.9800(2) 0.95115(19) 0.69409(14) 0.0439(4) Uani 1 1 d . . . . .
HN H 1.027362 1.042703 0.726739 0.053 Uiso 1 1 calc R U . . .
O1 O 0.5619(2) 0.02599(16) 0.36328(11) 0.0489(3) Uani 1 1 d . . . . .
H1O H 0.603378 0.115804 0.391492 0.073 Uiso 1 1 calc R U . . .
O3 O 0.2201(2) -0.22604(16) 0.01668(11) 0.0483(3) Uani 1 1 d . . . . .
Br1 Br 0.82814(3) 0.70194(2) 0.21547(2) 0.04155(7) Uani 1 1 d . . . . .
O2 O 0.7346(3) 0.38609(18) 0.60361(13) 0.0665(5) Uani 1 1 d . . . . .


_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 C2 1.404(2) . ?
C1 C6 1.405(2) . ?
C1 C7 1.442(2) . ?
C2 O1 1.3577(19) . ?
C2 C3 1.390(2) . ?
C3 C4 1.388(2) . ?
C4 O3 1.358(2) . ?
C4 C5 1.395(2) . ?
C5 C6 1.368(2) . ?
C7 N1 1.286(2) . ?
C8 O2 1.216(2) . ?
C8 N2 1.343(2) . ?
C8 C9 1.507(2) . ?
C9 C10 1.389(2) . ?
C9 C13 1.394(2) . ?
C10 C11 1.373(3) . ?
C11 N3 1.337(3) . ?
C12 N3 1.331(3) . ?
C12 C13 1.378(2) . ?
C14 O3 1.426(2) . ?
N1 N2 1.3824(19) . ?

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 C1 C6 117.69(15) . . ?
C2 C1 C7 122.72(15) . . ?
C6 C1 C7 119.59(15) . . ?
O1 C2 C3 117.50(15) . . ?
O1 C2 C1 121.15(15) . . ?
C3 C2 C1 121.34(15) . . ?
C4 C3 C2 119.02(15) . . ?
O3 C4 C3 123.91(15) . . ?
O3 C4 C5 115.40(15) . . ?
C3 C4 C5 120.68(15) . . ?
C6 C5 C4 119.66(15) . . ?
C5 C6 C1 121.57(16) . . ?
N1 C7 C1 120.58(16) . . ?
O2 C8 N2 124.40(16) . . ?
O2 C8 C9 120.68(15) . . ?
N2 C8 C9 114.92(14) . . ?
C10 C9 C13 119.41(16) . . ?
C10 C9 C8 117.05(15) . . ?
C13 C9 C8 123.42(15) . . ?
C11 C10 C9 119.31(17) . . ?
N3 C11 C10 119.74(17) . . ?
N3 C12 C13 120.16(17) . . ?
C12 C13 C9 118.66(17) . . ?
C7 N1 N2 116.47(15) . . ?
C8 N2 N1 118.19(14) . . ?
C12 N3 C11 122.68(16) . . ?
C4 O3 C14 117.80(15) . . ?

_refine_diff_density_max         0.605
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.051

# start Validation Reply Form
_vrf_PLAT910_shelx               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 11 Note
RESPONSE: These reflections were cut off by the beamstop
;
# end Validation Reply Form

####################################################################### 
# 
# 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_(HL1)NO3
_database_code_depnum_ccdc_archive 'CCDC 1589831'
_audit_update_record             
;
2018-05-22 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_diffrn_measurement_device_type  
;
PANalytical Empyrean diffractometer in the focusing
capillary transmision geometry
;
_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Cu K\a_1K\a_2'
_diffrn_radiation_wavelength     1.54060
_exptl_crystal_density_diffrn    1.53
_pd_proc_2theta_range_min        6.5
_pd_proc_2theta_range_max        55
_pd_proc_2theta_range_inc        0.007


_computing_structure_refinement  EXPO
_cell_measurement_temperature    293
_exptl_crystal_description       'microcrystalline powder'
_exptl_crystal_colour            yellow
_pd_proc_ls_profile_function     'Pearson VII'
_pd_proc_ls_background_function  'Chebychev polynomial'
_pd_proc_ls_prof_R_factor        0.0758
_pd_proc_ls_prof_wR_factor       0.0847
_refine_ls_goodness_of_fit_all   5.158
_audit_creation_method           Expo2014

_chemical_name_systematic        ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 N4 O6'
_chemical_formula_weight         333.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_cell_length_a                   11.4653(3)
_cell_length_b                   8.3036(2)
_cell_length_c                   8.2387(2)
_cell_angle_alpha                112.057(2)
_cell_angle_beta                 91.152(2)
_cell_angle_gamma                91.848(3)
_cell_volume                     726.12(4)
_cell_formula_units_Z            2

_symmetry_Int_Tables_number      2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_hall  '-P 1'

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 'x, y, z'
2 '-x, -y, -z'

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_occupancy
_atom_site_adp_type
O O3 0.4038(7) 0.1779(7) 0.6351(8) 0.0500 1.0000 Uiso
O O1 0.2309(9) 0.6525(17) 1.0739(11) 0.0500 1.0000 Uiso
N N2 -0.0638(3) 0.8388(7) 1.0458(4) 0.0500 1.0000 Uiso
H H2 -0.1240 0.8263 0.9700 0.0600 1.0000 Uiso
O O2 0.0272(9) 0.9980(3) 1.3042(7) 0.0500 1.0000 Uiso
N N3 -0.3509(13) 1.2749(3) 1.3869(7) 0.0500 1.0000 Uiso
H H3B -0.4120 1.3415 1.4284 0.0600 1.0000 Uiso
N N1 0.0279(5) 0.7284(10) 1.0042(5) 0.0500 1.0000 Uiso
C C1 0.1286(3) 0.5045(7) 0.8006(4) 0.0500 1.0000 Uiso
C C12 -0.3477(2) 1.1792(5) 1.2204(13) 0.0500 1.0000 Uiso
H H12 -0.4128 1.1820 1.1428 0.0600 1.0000 Uiso
C C8 -0.0582(2) 0.9649(5) 1.2046(2) 0.0500 1.0000 Uiso
C C9 -0.1661(2) 1.0720(6) 1.2601(17) 0.0500 1.0000 Uiso
C C3 0.3175(4) 0.4177(9) 0.8628(5) 0.0500 1.0000 Uiso
H H3 0.3847 0.4335 0.9434 0.0600 1.0000 Uiso
C C5 0.2222(2) 0.2646(4) 0.5843(2) 0.0500 1.0000 Uiso
H H5 0.2215 0.1723 0.4674 0.0600 1.0000 Uiso
C C2 0.2237(4) 0.5254(8) 0.9135(5) 0.0500 1.0000 Uiso
C C6 0.1295(3) 0.3718(6) 0.6357(5) 0.0500 1.0000 Uiso
H H6 0.0626 0.3542 0.5542 0.0600 1.0000 Uiso
C C13 -0.2565(3) 1.0744(7) 1.1492(17) 0.0500 1.0000 Uiso
H H13 -0.2561 1.0039 1.0235 0.0600 1.0000 Uiso
C C4 0.3150(3) 0.2886(6) 0.6983(4) 0.0500 1.0000 Uiso
C C14 0.5016(17) 0.1936(3) 0.7511(3) 0.0500 1.0000 Uiso
H H14 0.5557 0.1122 0.6938 0.0750 1.0000 Uiso
H H14A 0.4767 0.1740 0.8491 0.0750 1.0000 Uiso
H H14B 0.5360 0.3049 0.7859 0.0750 1.0000 Uiso
C C7 0.0302(3) 0.6147(6) 0.8525(3) 0.0500 1.0000 Uiso
H H7 -0.0350 0.6005 0.7689 0.0600 1.0000 Uiso
C C11 -0.2646(16) 1.2739(4) 1.4941(10) 0.0500 1.0000 Uiso
H H11 -0.2682 1.3453 1.6192 0.0600 1.0000 Uiso
C C10 -0.1696(14) 1.1748(3) 1.4340(10) 0.0500 1.0000 Uiso
H H10 -0.1050 1.1777 1.5148 0.0600 1.0000 Uiso
O O4 -0.4364(17) 0.5818(19) 0.6729(16) 0.0500 1.0000 Uiso
O O5 -0.2446(19) 0.6575(18) 0.7861(17) 0.0500 1.0000 Uiso
O O6 -0.3845(17) 0.8704(19) 0.8518(17) 0.0500 1.0000 Uiso
N N4 -0.3552(19) 0.7033(19) 0.7704(15) 0.0500 1.0000 Uiso

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
O3 C4 . . 1.369(8)
O3 C14 . . 1.429(17)
O1 C2 . . 1.345(11)
N2 H2 . . 0.9000
N2 N1 . . 1.380(8)
N2 C8 . . 1.333(4)
O2 C8 . . 1.220(9)
N3 H3B . . 0.9000
N3 C12 . . 1.304(11)
N3 C11 . . 1.315(18)
N1 C7 . . 1.253(6)
C1 C2 . . 1.382(5)
C1 C6 . . 1.392(6)
C1 C7 . . 1.444(6)
C12 H12 . . 0.9800
C12 C13 . . 1.377(9)
C8 C9 . . 1.523(6)
C9 C13 . . 1.374(12)
C9 C10 . . 1.367(15)
C3 H3 . . 0.9800
C3 C2 . . 1.389(8)
C3 C4 . . 1.376(6)
C5 H5 . . 0.9800
C5 C6 . . 1.377(5)
C5 C4 . . 1.364(4)
C6 H6 . . 0.9800
C13 H13 . . 0.9800
C14 H14 . . 0.9300
C14 H14A . . 0.9300
C14 H14B . . 0.9300
C7 H7 . . 0.9800
C11 H11 . . 0.9800
C11 C10 . . 1.37(2)
C10 H10 . . 0.9800
O4 N4 . . 1.35(2)
O5 N4 . . 1.364(4)
O6 N4 . . 1.35(3)

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_2
_geom_angle_site_symmetry_3
_geom_angle
C4 O3 C14 . . . 117.4(6)
O3 C4 C3 . . . 123.7(4)
O3 C4 C5 . . . 115.1(4)
O3 C14 H14 . . . 109.00
O3 C14 H14A . . . 109.00
O3 C14 H14B . . . 109.00
O1 C2 C1 . . . 121.8(6)
O1 C2 C3 . . . 117.4(6)
H2 N2 N1 . . . 122.00
H2 N2 C8 . . . 122.00
N1 N2 C8 . . . 116.4(3)
N2 N1 C7 . . . 118.7(4)
N2 C8 O2 . . . 123.9(4)
N2 C8 C9 . . . 116.5(5)
O2 C8 C9 . . . 119.6(6)
H3B N3 C12 . . . 120.00
H3B N3 C11 . . . 120.00
C12 N3 C11 . . . 120.0(11)
N3 C12 H12 . . . 119.00
N3 C12 C13 . . . 122.7(9)
N3 C11 H11 . . . 119.00
N3 C11 C10 . . . 121.2(8)
N1 C7 C1 . . . 120.2(4)
N1 C7 H7 . . . 120.00
C2 C1 C6 . . . 118.0(4)
C2 C1 C7 . . . 121.3(3)
C1 C2 C3 . . . 120.8(4)
C6 C1 C7 . . . 120.8(3)
C1 C6 C5 . . . 121.6(3)
C1 C6 H6 . . . 119.00
C1 C7 H7 . . . 119.9
H12 C12 C13 . . . 119.00
C12 C13 C9 . . . 117.8(11)
C12 C13 H13 . . . 121.00
C8 C9 C13 . . . 125.1(10)
C8 C9 C10 . . . 115.9(8)
C13 C9 C10 . . . 119.0(9)
C9 C13 H13 . . . 121.00
C9 C10 C11 . . . 119.3(10)
C9 C10 H10 . . . 120.00
H3 C3 C2 . . . 120.00
H3 C3 C4 . . . 120.00
C2 C3 C4 . . . 119.3(4)
C3 C4 C5 . . . 121.2(4)
H5 C5 C6 . . . 120.00
H5 C5 C4 . . . 120.00
C6 C5 C4 . . . 119.1(3)
C5 C6 H6 . . . 119.00
H14 C14 H14A . . . 109.00
H14 C14 H14B . . . 109.00
H14A C14 H14B . . . 109.00
H11 C11 C10 . . . 119.00
C11 C10 H10 . . . 120.00
O4 N4 O5 . . . 119.9(15)
O4 N4 O6 . . . 120.0(19)
O5 N4 O6 . . . 120.0(17)

####################################################################### 
# 
# 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_shelx_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 1589828'
_audit_update_record             
;
2018-05-22 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N4 O6'
_chemical_formula_weight         334.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   21.7477(6)
_cell_length_b                   7.4586(2)
_cell_length_c                   19.5150(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.492(4)
_cell_angle_gamma                90
_cell_volume                     2924.69(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10414
_cell_measurement_theta_min      2.0410
_cell_measurement_theta_max      32.9330

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63989
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  synchrotron
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34567
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.996
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             8801
_reflns_number_gt                6483
_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       syncrotron
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS(Sheldrick, 1990, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0551P)²+2.4104P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8801
_refine_ls_number_parameters     437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1346
_refine_ls_wR_factor_gt          0.1241
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
O21 O 0.03346(6) 0.03753(17) 0.36183(6) 0.0155(2) Uani 1 1 d . . . . .
H21 H 0.020989 0.084036 0.392354 0.023 Uiso 1 1 calc R U . . .
O23 O 0.08642(6) -0.11781(17) 0.27872(6) 0.0162(2) Uani 1 1 d . . . . .
O22 O -0.07157(7) 0.30941(19) 0.44150(7) 0.0220(3) Uani 1 1 d . . . . .
N22 N 0.02279(7) 0.23955(19) 0.53996(8) 0.0149(3) Uani 1 1 d . . . . .
H22 H 0.045204 0.244613 0.587006 0.018 Uiso 1 1 calc R U . . .
N23 N -0.11908(7) 0.60425(19) 0.64138(8) 0.0150(3) Uani 1 1 d . . . . .
H23 H -0.136353 0.663363 0.667416 0.018 Uiso 1 1 calc R U . . .
C29 C -0.06431(8) 0.4154(2) 0.55911(9) 0.0135(3) Uani 1 1 d . . . . .
C22 C 0.09697(7) -0.0204(2) 0.39618(9) 0.0125(3) Uani 1 1 d . . . . .
N21 N 0.04689(7) 0.15336(19) 0.49287(8) 0.0147(3) Uani 1 1 d . . . . .
C27 C 0.10600(8) 0.0874(2) 0.52112(9) 0.0157(3) Uani 1 1 d . . . . .
H27 H 0.130693 0.095890 0.571826 0.019 Uiso 1 1 calc R U . . .
C23 C 0.12661(8) -0.1044(2) 0.35184(8) 0.0125(3) Uani 1 1 d . . . . .
C28 C -0.03842(8) 0.3162(2) 0.50790(9) 0.0141(3) Uani 1 1 d . . . . .
C214 C 0.11358(9) -0.2048(2) 0.23114(10) 0.0183(3) Uani 1 1 d . . . . .
H21A H 0.153329 -0.143647 0.233972 0.027 Uiso 1 1 calc R U . . .
H21B H 0.081594 -0.201900 0.180983 0.027 Uiso 1 1 calc R U . . .
H21C H 0.124021 -0.327024 0.246587 0.027 Uiso 1 1 calc R U . . .
C211 C -0.15425(8) 0.5866(2) 0.56810(9) 0.0158(3) Uani 1 1 d . . . . .
H211 H -0.196343 0.637541 0.546419 0.019 Uiso 1 1 calc R U . . .
C21 C 0.13380(8) -0.0008(2) 0.47283(9) 0.0135(3) Uani 1 1 d . . . . .
C212 C -0.05812(8) 0.5334(2) 0.67562(9) 0.0151(3) Uani 1 1 d . . . . .
H212 H -0.035401 0.548752 0.726409 0.018 Uiso 1 1 calc R U . . .
C24 C 0.19144(8) -0.1668(2) 0.38347(9) 0.0155(3) Uani 1 1 d . . . . .
H24 H 0.210608 -0.223156 0.354001 0.019 Uiso 1 1 calc R U . . .
C210 C -0.12730(8) 0.4922(2) 0.52531(9) 0.0157(3) Uani 1 1 d . . . . .
H210 H -0.150898 0.480043 0.474520 0.019 Uiso 1 1 calc R U . . .
C213 C -0.02938(8) 0.4378(2) 0.63504(9) 0.0150(3) Uani 1 1 d . . . . .
H213 H 0.012901 0.388882 0.658179 0.018 Uiso 1 1 calc R U . . .
C26 C 0.19982(8) -0.0632(2) 0.50342(9) 0.0169(3) Uani 1 1 d . . . . .
H26 H 0.224550 -0.048786 0.553871 0.020 Uiso 1 1 calc R U . . .
C25 C 0.22830(8) -0.1454(2) 0.45957(10) 0.0179(3) Uani 1 1 d . . . . .
H25 H 0.271918 -0.186683 0.480443 0.021 Uiso 1 1 calc R U . . .
O24 O 0.18823(6) 0.20940(18) 0.28797(7) 0.0179(2) Uani 1 1 d . . . . .
O25 O 0.10316(6) 0.31868(18) 0.19669(7) 0.0191(3) Uani 1 1 d . . . . .
N24 N 0.15696(7) 0.23059(19) 0.21897(8) 0.0146(3) Uani 1 1 d . . . . .
O26 O 0.17857(7) 0.16552(19) 0.17400(7) 0.0232(3) Uani 1 1 d . . . . .
O11 O 0.47836(6) 0.46258(18) 0.33508(7) 0.0180(2) Uani 1 1 d . . . . .
H11 H 0.491524 0.415409 0.376146 0.027 Uiso 1 1 calc R U . . .
O13 O 0.42083(6) 0.60980(18) 0.20452(7) 0.0196(3) Uani 1 1 d . . . . .
O16 O 0.69361(6) -0.2565(2) 1.00047(7) 0.0252(3) Uani 1 1 d . . . . .
N12 N 0.48961(7) 0.2444(2) 0.52258(8) 0.0161(3) Uani 1 1 d . . . . .
H12 H 0.464633 0.231543 0.547377 0.019 Uiso 1 1 calc R U . . .
12 O 0.59078(7) 0.2020(2) 0.51614(7) 0.0244(3) Uani 1 1 d . . . . .
O15 O 0.60606(6) -0.21276(19) 0.89924(7) 0.0222(3) Uani 1 1 d . . . . .
N11 N 0.46653(7) 0.32639(19) 0.45383(8) 0.0156(3) Uani 1 1 d . . . . .
C18 C 0.55376(8) 0.1848(2) 0.54934(9) 0.0159(3) Uani 1 1 d . . . . .
C13 C 0.38012(8) 0.5735(2) 0.24133(9) 0.0150(3) Uani 1 1 d . . . . .
C12 C 0.41207(8) 0.4958(2) 0.31186(9) 0.0141(3) Uani 1 1 d . . . . .
C19 C 0.57784(8) 0.0929(2) 0.62400(9) 0.0139(3) Uani 1 1 d . . . . .
C11 C 0.37517(8) 0.4580(2) 0.35549(9) 0.0148(3) Uani 1 1 d . . . . .
N14 N 0.66841(7) -0.2147(2) 0.93388(8) 0.0170(3) Uani 1 1 d . . . . .
N13 N 0.63204(7) -0.0703(2) 0.75905(8) 0.0164(3) Uani 1 1 d . . . . .
H13 H 0.649293 -0.119837 0.802002 0.020 Uiso 1 1 calc R U . . .
O14 O 0.70527(7) -0.1740(2) 0.89996(8) 0.0307(3) Uani 1 1 d . . . . .
C112 C 0.56817(8) -0.0173(2) 0.73472(9) 0.0168(3) Uani 1 1 d . . . . .
H112 H 0.543276 -0.036669 0.763596 0.020 Uiso 1 1 calc R U . . .
C113 C 0.53966(8) 0.0663(2) 0.66647(9) 0.0160(3) Uani 1 1 d . . . . .
H113 H 0.495587 0.104233 0.649162 0.019 Uiso 1 1 calc R U . . .
C17 C 0.40511(8) 0.3757(2) 0.42841(9) 0.0169(3) Uani 1 1 d . . . . .
H17 H 0.379700 0.358497 0.456862 0.020 Uiso 1 1 calc R U . . .
C110 C 0.64342(8) 0.0314(2) 0.65030(10) 0.0170(3) Uani 1 1 d . . . . .
H110 H 0.668883 0.044645 0.621684 0.020 Uiso 1 1 calc R U . . .
C14 C 0.31250(8) 0.6090(2) 0.21498(9) 0.0183(3) Uani 1 1 d . . . . .
H14 H 0.291551 0.660916 0.168458 0.022 Uiso 1 1 calc R U . . .
C16 C 0.30651(8) 0.4951(2) 0.32740(10) 0.0197(3) Uani 1 1 d . . . . .
H16 H 0.281874 0.470393 0.356116 0.024 Uiso 1 1 calc R U . . .
C111 C 0.67024(8) -0.0493(2) 0.71925(10) 0.0186(3) Uani 1 1 d . . . . .
H111 H 0.714160 -0.088587 0.737897 0.022 Uiso 1 1 calc R U . . .
C114 C 0.38965(10) 0.6732(3) 0.12988(9) 0.0225(4) Uani 1 1 d . . . . .
H11A H 0.356965 0.587845 0.101046 0.034 Uiso 1 1 calc R U . . .
H11B H 0.422639 0.688227 0.108827 0.034 Uiso 1 1 calc R U . . .
H11C H 0.368439 0.786209 0.129724 0.034 Uiso 1 1 calc R U . . .
C15 C 0.27554(8) 0.5676(3) 0.25768(10) 0.0214(4) Uani 1 1 d . . . . .
H15 H 0.229953 0.589061 0.239030 0.026 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
O21 C22 1.3548(19) . ?
O23 C23 1.3624(19) . ?
O23 C214 1.4321(19) . ?
O22 C28 1.219(2) . ?
N22 C28 1.361(2) . ?
N22 N21 1.3787(18) . ?
N23 C212 1.344(2) . ?
N23 C211 1.346(2) . ?
C29 C213 1.393(2) . ?
C29 C210 1.396(2) . ?
C29 C28 1.514(2) . ?
C22 C21 1.408(2) . ?
C22 C23 1.409(2) . ?
N21 C27 1.287(2) . ?
C27 C21 1.457(2) . ?
C23 C24 1.385(2) . ?
C211 C210 1.382(2) . ?
C21 C26 1.407(2) . ?
C212 C213 1.380(2) . ?
C24 C25 1.401(2) . ?
C26 C25 1.377(2) . ?
O24 N24 1.2650(18) . ?
O25 N24 1.2650(18) . ?
N24 O26 1.2418(18) . ?
O11 C12 1.3586(19) . ?
O13 C13 1.3637(19) . ?
O13 C114 1.432(2) . ?
O16 N14 1.2415(19) . ?
N12 C18 1.363(2) . ?
N12 N11 1.3824(19) . ?
12 C18 1.218(2) . ?
O15 N14 1.2627(18) . ?
N11 C17 1.288(2) . ?
C18 C19 1.511(2) . ?
C13 C14 1.385(2) . ?
C13 C12 1.408(2) . ?
C12 C11 1.404(2) . ?
C19 C113 1.394(2) . ?
C19 C110 1.396(2) . ?
C11 C16 1.407(2) . ?
C11 C17 1.455(2) . ?
N14 O14 1.2566(19) . ?
N13 C112 1.344(2) . ?
N13 C111 1.346(2) . ?
C112 C113 1.384(2) . ?
C110 C111 1.383(2) . ?
C14 C15 1.396(2) . ?
C16 C15 1.377(3) . ?

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
C23 O23 C214 116.98(13) . . ?
C28 N22 N21 116.35(14) . . ?
C212 N23 C211 122.79(14) . . ?
C213 C29 C210 119.37(15) . . ?
C213 C29 C28 124.87(14) . . ?
C210 C29 C28 115.74(15) . . ?
O21 C22 C21 123.40(14) . . ?
O21 C22 C23 117.22(14) . . ?
C21 C22 C23 119.38(14) . . ?
C27 N21 N22 117.70(14) . . ?
N21 C27 C21 119.29(15) . . ?
O23 C23 C24 125.31(14) . . ?
O23 C23 C22 114.52(13) . . ?
C24 C23 C22 120.17(14) . . ?
O22 C28 N22 123.21(15) . . ?
O22 C28 C29 120.23(15) . . ?
N22 C28 C29 116.55(14) . . ?
N23 C211 C210 119.46(15) . . ?
C26 C21 C22 119.34(14) . . ?
C26 C21 C27 118.93(15) . . ?
C22 C21 C27 121.71(14) . . ?
N23 C212 C213 119.68(15) . . ?
C23 C24 C25 120.42(15) . . ?
C211 C210 C29 119.34(15) . . ?
C212 C213 C29 119.35(15) . . ?
C25 C26 C21 120.80(15) . . ?
C26 C25 C24 119.89(15) . . ?
O26 N24 O24 120.58(14) . . ?
O26 N24 O25 120.70(14) . . ?
O24 N24 O25 118.72(13) . . ?
C13 O13 C114 116.83(13) . . ?
C18 N12 N11 117.03(13) . . ?
C17 N11 N12 116.00(14) . . ?
12 C18 N12 123.34(16) . . ?
12 C18 C19 120.33(15) . . ?
N12 C18 C19 116.33(14) . . ?
O13 C13 C14 125.27(15) . . ?
O13 C13 C12 114.81(14) . . ?
C14 C13 C12 119.91(15) . . ?
O11 C12 C11 122.75(14) . . ?
O11 C12 C13 117.72(14) . . ?
C11 C12 C13 119.53(14) . . ?
C113 C19 C110 119.48(15) . . ?
C113 C19 C18 124.92(15) . . ?
C110 C19 C18 115.60(14) . . ?
C12 C11 C16 119.46(15) . . ?
C12 C11 C17 122.15(15) . . ?
C16 C11 C17 118.36(15) . . ?
O16 N14 O14 119.79(14) . . ?
O16 N14 O15 121.13(14) . . ?
O14 N14 O15 119.08(14) . . ?
C112 N13 C111 123.00(15) . . ?
N13 C112 C113 119.63(15) . . ?
C112 C113 C19 119.14(15) . . ?
N11 C17 C11 120.49(15) . . ?
C111 C110 C19 119.48(15) . . ?
C13 C14 C15 120.53(16) . . ?
C15 C16 C11 120.47(16) . . ?
N13 C111 C110 119.24(15) . . ?
C16 C15 C14 120.07(16) . . ?

_refine_diff_density_max         0.443
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_(HL1)HSO4-alpha
_database_code_depnum_ccdc_archive 'CCDC 1589829'
_audit_update_record             
;
2018-05-22 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_diffrn_measurement_device_type  
;
PANalytical Empyrean diffractometer in the focusing
capillary transmision geometry
;
_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Cu K\a_1K\a_2'
_diffrn_radiation_wavelength     1.54060
_exptl_crystal_density_diffrn    1.55
_pd_proc_2theta_range_min        4
_pd_proc_2theta_range_max        65
_pd_proc_2theta_range_inc        0.007

_computing_structure_refinement  EXPO
_cell_measurement_temperature    293
_exptl_crystal_description       'microcrystalline powder'
_exptl_crystal_colour            orange
_pd_proc_ls_profile_function     'Pearson VII'
_pd_proc_ls_background_function  'Chebychev polynomial'
_pd_proc_ls_prof_R_factor        0.05152
_pd_proc_ls_prof_wR_factor       0.06723
_refine_ls_goodness_of_fit_all   3.466
_audit_creation_method           Expo2014

_chemical_name_systematic        ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 N3 O7 S1'
_chemical_formula_weight         368.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_cell_length_a                   7.6971(10)
_cell_length_b                   33.773(3)
_cell_length_c                   6.3002(6)
_cell_angle_alpha                90.000
_cell_angle_beta                 104.838(10)
_cell_angle_gamma                90.000
_cell_volume                     1583.1(3)
_cell_formula_units_Z            4

_symmetry_Int_Tables_number      14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_symmetry_space_group_name_hall  '-P 2yab'

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

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_occupancy
_atom_site_adp_type
O O3 0.8875(7) 0.5172(17) -0.8192(9) 0.0500 1.0000 Uiso
O O1 0.5067(13) 0.5616(17) -0.3800(15) 0.0500 1.0000 Uiso
N N2 0.6227(6) 0.6304(17) 0.1058(12) 0.0500 1.0000 Uiso
H H2 0.6983 0.6505 0.1585 0.0607 1.0000 Uiso
O O2 0.3432(13) 0.6055(19) 0.0554(10) 0.0500 1.0000 Uiso
N N3 0.4301(13) 0.6943(14) 0.7113(8) 0.0500 1.0000 Uiso
H H3 0.4253 0.7090 0.8286 0.0611 1.0000 Uiso
N N1 0.6622(7) 0.6021(15) -0.0333(12) 0.0500 1.0000 Uiso
C C1 0.8100(3) 0.5844(16) -0.3013(8) 0.0500 1.0000 Uiso
C C11 0.3027(6) 0.6689(18) 0.6303(9) 0.0500 1.0000 Uiso
H H11 0.2029 0.6664 0.6998 0.0596 1.0000 Uiso
C C8 0.4659((6) 0.6264(19) 0.1570(9) 0.0500 1.0000 Uiso
C C9 0.4440(7) 0.6495(2) 0.3561(11) 0.0500 1.0000 Uiso
C C3 0.6889(4) 0.5399(3) -0.6020(11) 0.0500 1.0000 Uiso
H H4 0.5877 0.5244 -0.6896 0.0584 1.0000 Uiso
C C5 0.9951(5) 0.5606(3) -0.5319(14) 0.0500 1.0000 Uiso
H H5 1.1112 0.5599 -0.5691 0.0631 1.0000 Uiso
C C2 0.6680(11) 0.5626(7) -0.4261(3) 0.0500 1.0000 Uiso
C C6 0.9733(12) 0.5830(7) -0.3581(3) 0.0500 1.0000 Uiso
H H6 1.0752 0.5985 -0.2722 0.0586 1.0000 Uiso
C C10 0.3027(7) 0.6457(2) 0.4511(10) 0.0500 1.0000 Uiso
H H10 0.2049 0.6269 0.3929 0.0532 1.0000 Uiso
C C4 0.8529(3) 0.5392(2) -0.6518(9) 0.0500 1.0000 Uiso
C C14 0.7481(2) 0.4915(6) -0.9375(3) 0.0500 1.0000 Uiso
H H14 0.7873 0.4783 -1.0462 0.0717 1.0000 Uiso
H H14A 0.6467 0.5065 -1.0020 0.0717 1.0000 Uiso
H H14B 0.7197 0.4732 -0.8413 0.0717 1.0000 Uiso
C C7 0.7894(3) 0.6085(9) -0.1198(5) 0.0500 1.0000 Uiso
H H7 0.8749 0.6300 -0.0640 0.0590 1.0000 Uiso
C C12 0.5656(4) 0.6984(13) 0.6214(6) 0.0500 1.0000 Uiso
H H12 0.6614 0.7174 0.6848 0.0706 1.0000 Uiso
C C13 0.5755(4) 0.6767(13) 0.4407(6) 0.0500 1.0000 Uiso
H H13 0.6756 0.6807 0.3730 0.0597 1.0000 Uiso
S S1 0.5003(19) 0.7841(15) 1.1005(19) 0.0500 1.0000 Uiso
O O4 0.4039(19) 0.8102(17) 1.2199(15) 0.0500 1.0000 Uiso
O O5 0.6689(17) 0.7703(19) 1.2517(19) 0.0500 1.0000 Uiso
H H5A 0.7401 0.7638 1.1808 0.0669 1.0000 Uiso
O O6 0.5420(19) 0.8064(17) 0.9180(19) 0.0500 1.0000 Uiso
O O7 0.3865(17) 0.7498(18) 1.0122(17) 0.0500 1.0000 Uiso

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
O3 C4 . . 1.37(3)
O3 C14 . . 1.43(14)
O1 C2 . . 1.346(13)
N2 H2 . . 0.9000
N2 N1 . . 1.38(5)
N2 C8 . . 1.334(11)
O2 C8 . . 1.22(5)
N3 H3 . . 0.9000
N3 C11 . . 1.30(5)
N3 C12 . . 1.315(12)
N1 C7 . . 1.255(12)
C1 C2 . . 1.38(3)
C1 C6 . . 1.393(10)
C1 C7 . . 1.45(3)
C11 H11 . . 0.9000
C11 C10 . . 1.37(4)
C8 C9 . . 1.52(3)
C9 C10 . . 1.375(8)
C9 C13 . . 1.37(3)
C3 H4 . . 0.9000
C3 C2 . . 1.390(16)
C3 C4 . . 1.377(5)
C5 H5 . . 0.9000
C5 C6 . . 1.376(16)
C5 C4 . . 1.367(9)
C6 H6 . . 0.9000
C10 H10 . . 0.9000
C14 H14 . . 0.9000
C14 H14A . . 0.9000
C14 H14B . . 0.9000
C7 H7 . . 0.9000
C12 H12 . . 0.9000
C12 C13 . . 1.37(3)
C13 H13 . . 0.9000
S1 O4 . . 1.48(5)
S1 O5 . . 1.48(3)
S1 O6 . . 1.48(4)
S1 O7 . . 1.47(6)
O5 H5A . . 0.8200
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_2
_geom_angle_site_symmetry_3
_geom_angle
C4 O3 C14 . . . 117.5(6)
O3 C4 C3 . . . 123.7(10)
O3 C4 C5 . . . 115.2(9)
O3 C14 H14 . . . 109.00
O3 C14 H14A . . . 109.00
O3 C14 H14B . . . 109.00
O1 C2 C1 . . . 121.9(19)
O1 C2 C3 . . . 117.4(19)
H2 N2 N1 . . . 122.00
H2 N2 C8 . . . 122.00
N1 N2 C8 . . . 116(4)
N2 N1 C7 . . . 119(4)
N2 C8 O2 . . . 124(3)
N2 C8 C9 . . . 116(3)
O2 C8 C9 . . . 119.6(11)
H3 N3 C11 . . . 120.00
H3 N3 C12 . . . 120.00
C11 N3 C12 . . . 120(3)
N3 C11 H11 . . . 119.00
N3 C11 C10 . . . 122.6(8)
N3 C12 H12 . . . 119.00
N3 C12 C13 . . . 121(3)
N1 C7 C1 . . . 120(3)
N1 C7 H7 . . . 120.00
C2 C1 C6 . . . 118(2)
C2 C1 C7 . . . 121.2(6)
C1 C2 C3 . . . 120.7(9)
C6 C1 C7 . . . 121(2)
C1 C6 C5 . . . 121.7(17)
C1 C6 H6 . . . 119.00
C1 C7 H7 . . . 120.0
H11 C11 C10 . . . 119.00
C11 C10 C9 . . . 118.1(12)
C11 C10 H10 . . . 121.00
C8 C9 C10 . . . 125.3(13)
C8 C9 C13 . . . 115.9(14)
C10 C9 C13 . . . 118.8(7)
C9 C10 H10 . . . 121.00
C9 C13 C12 . . . 119.2(10)
C9 C13 H13 . . . 121.00
H4 C3 C2 . . . 120.00
H4 C3 C4 . . . 120.00
C2 C3 C4 . . . 119.4(7)
C3 C4 C5 . . . 121.1(6)
H5 C5 C6 . . . 121.00
H5 C5 C4 . . . 120.00
C6 C5 C4 . . . 119.1(6)
C5 C6 H6 . . . 119.00
H14 C14 H14A . . . 109.00
H14 C14 H14B . . . 110.00
H14A C14 H14B . . . 110.00
H12 C12 C13 . . . 119.00
C12 C13 H13 . . . 120.00
O4 S1 O5 . . . 109.5(18)
O4 S1 O6 . . . 109(4)
O4 S1 O7 . . . 110(2)
O5 S1 O6 . . . 109.5(17)
O5 S1 O7 . . . 110(4)
S1 O5 H5A . . . 109.00
O6 S1 O7 . . . 110(2)

####################################################################### 
# 
# 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_shelx_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 1589823'
_audit_update_record             
;
2018-05-22 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Br N3 O3'
_chemical_formula_weight         352.19

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   5.1013(5)
_cell_length_b                   36.044(4)
_cell_length_c                   8.0122(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.091(8)
_cell_angle_gamma                90
_cell_volume                     1472.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1392
_cell_measurement_theta_min      4.5760
_cell_measurement_theta_max      25.8070

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    2.806
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.41559
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7789
_diffrn_reflns_av_unetI/netI     0.0971
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.241
_diffrn_reflns_theta_max         28.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3796
_reflns_number_gt                2321
_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       'CrysAlis CCD (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS (Sheldrick, 1990, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0298P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3796
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_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 0.9863(7) 0.15702(10) 0.2224(5) 0.0410(9) Uani 1 1 d . . . . .
C2 C 1.1422(7) 0.17848(11) 0.3326(5) 0.0396(9) Uani 1 1 d . . . . .
C3 C 1.3300(7) 0.20263(11) 0.2736(5) 0.0428(10) Uani 1 1 d . . . . .
H3A H 1.430378 0.217003 0.348080 0.051 Uiso 1 1 calc R U . . .
C4 C 1.3672(8) 0.20523(11) 0.1050(5) 0.0450(10) Uani 1 1 d . . . . .
C5 C 1.2160(8) 0.18404(12) -0.0080(5) 0.0543(11) Uani 1 1 d . . . . .
H5 H 1.242678 0.185654 -0.122005 0.065 Uiso 1 1 calc R U . . .
C6 C 1.0276(9) 0.16079(12) 0.0509(6) 0.0556(12) Uani 1 1 d . . . . .
H6 H 0.924221 0.147149 -0.024873 0.067 Uiso 1 1 calc R U . . .
C7 C 0.7792(7) 0.13310(11) 0.2784(5) 0.0450(10) Uani 1 1 d . . . . .
H7 H 0.674325 0.120230 0.200664 0.054 Uiso 1 1 calc R U . . .
C8 C 0.4839(7) 0.10490(11) 0.6434(5) 0.0416(10) Uani 1 1 d . . . . .
C9 C 0.2623(6) 0.07953(10) 0.6889(5) 0.0359(9) Uani 1 1 d . . . . .
C10 C 0.2189(7) 0.07577(11) 0.8587(5) 0.0485(11) Uani 1 1 d . . . . .
H10 H 0.323480 0.088687 0.936424 0.058 Uiso 1 1 calc R U . . .
C11 C 0.0235(8) 0.05318(13) 0.9115(5) 0.0544(12) Uani 1 1 d . . . . .
H11 H -0.005226 0.050569 1.024877 0.065 Uiso 1 1 calc R U . . .
C12 C -0.0914(7) 0.03720(11) 0.6351(5) 0.0459(10) Uani 1 1 d . . . . .
H12 H -0.198274 0.023699 0.560819 0.055 Uiso 1 1 calc R U . . .
C13 C 0.1034(7) 0.05966(11) 0.5760(5) 0.0405(9) Uani 1 1 d . . . . .
H13 H 0.128195 0.061502 0.461869 0.049 Uiso 1 1 calc R U . . .
C14 C 1.6987(8) 0.25177(13) 0.1418(6) 0.0668(14) Uani 1 1 d . . . . .
H14A H 1.820258 0.265423 0.076734 0.100 Uiso 1 1 calc R U . . .
H14B H 1.793636 0.237283 0.224340 0.100 Uiso 1 1 calc R U . . .
H14C H 1.584681 0.268768 0.196121 0.100 Uiso 1 1 calc R U . . .
N1 N 0.7396(6) 0.12959(9) 0.4349(4) 0.0429(8) Uani 1 1 d . . . . .
N2 N 0.5352(6) 0.10696(9) 0.4802(4) 0.0426(8) Uani 1 1 d . . . . .
H2 H 0.444093 0.094656 0.406725 0.051 Uiso 1 1 calc R U . . .
N3 N -0.1263(6) 0.03486(9) 0.7983(4) 0.0452(8) Uani 1 1 d . . . . .
H3 H -0.250359 0.020976 0.832686 0.054 Uiso 1 1 calc R U . . .
O1 O 1.1142(5) 0.17727(8) 0.5012(3) 0.0522(7) Uani 1 1 d . . . . .
H1 H 1.001031 0.162058 0.523108 0.078 Uiso 1 1 calc R U . . .
O2 O 0.6067(5) 0.12203(9) 0.7513(4) 0.0619(9) Uani 1 1 d . . . . .
O3 O 1.5470(6) 0.22786(9) 0.0354(4) 0.0592(8) Uani 1 1 d . . . . .
Br1 Br 0.55458(8) 0.03159(2) 0.22433(5) 0.04707(15) Uani 1 1 d . . . . .


_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 C2 1.400(5) . ?
C1 C6 1.404(5) . ?
C1 C7 1.448(5) . ?
C2 O1 1.364(4) . ?
C2 C3 1.390(5) . ?
C3 C4 1.374(5) . ?
C4 O3 1.362(4) . ?
C4 C5 1.395(6) . ?
C5 C6 1.372(5) . ?
C7 N1 1.284(5) . ?
C8 O2 1.217(4) . ?
C8 N2 1.345(5) . ?
C8 C9 1.509(5) . ?
C9 C10 1.393(5) . ?
C9 C13 1.391(5) . ?
C10 C11 1.367(5) . ?
C11 N3 1.339(5) . ?
C12 N3 1.329(5) . ?
C12 C13 1.379(5) . ?
C14 O3 1.421(5) . ?
N1 N2 1.383(4) . ?

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 C1 C6 117.5(4) . . ?
C2 C1 C7 122.5(4) . . ?
C6 C1 C7 119.9(4) . . ?
O1 C2 C3 117.1(3) . . ?
O1 C2 C1 122.0(4) . . ?
C3 C2 C1 120.9(4) . . ?
C4 C3 C2 119.9(4) . . ?
O3 C4 C3 124.2(4) . . ?
O3 C4 C5 115.3(4) . . ?
C3 C4 C5 120.5(4) . . ?
C6 C5 C4 119.3(4) . . ?
C5 C6 C1 121.9(4) . . ?
N1 C7 C1 120.3(4) . . ?
O2 C8 N2 123.3(4) . . ?
O2 C8 C9 120.4(4) . . ?
N2 C8 C9 116.3(3) . . ?
C10 C9 C13 118.4(4) . . ?
C10 C9 C8 116.2(3) . . ?
C13 C9 C8 125.4(4) . . ?
C11 C10 C9 120.3(4) . . ?
N3 C11 C10 119.3(4) . . ?
N3 C12 C13 120.0(4) . . ?
C12 C13 C9 119.3(4) . . ?
C7 N1 N2 117.5(3) . . ?
C8 N2 N1 117.6(3) . . ?
C12 N3 C11 122.8(4) . . ?
C4 O3 C14 118.5(3) . . ?

_refine_diff_density_max         0.643
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.082


# start Validation Reply Form
_vrf_PLAT910_shelx               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 11 Note
RESPONSE: These reflections were cut off by the beamstop
;
# end Validation Reply Form
