# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_global
_database_code_depnum_ccdc_archive 'CCDC 1052283'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

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



_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H19 F N2 O3, C H2 Cl2'
_chemical_formula_sum            'C23 H21 Cl2 F N2 O3'
_chemical_formula_weight         463.32

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.9049(18)
_cell_length_b                   24.490(4)
_cell_length_c                   8.7934(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.040(3)
_cell_angle_gamma                90.00
_cell_volume                     2121.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8152
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      30.09

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          1.35
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6541
_exptl_absorpt_correction_T_max  0.9345
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19828
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         28.00
_reflns_number_total             5114
_reflns_number_gt                4113
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0798P)²+5.2951P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5114
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0706
_refine_ls_wR_factor_ref         0.1877
_refine_ls_wR_factor_gt          0.1748
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.62094(11) 0.01110(5) 0.13645(15) 0.0566(3) Uani 1 1 d . . .
Cl2 Cl 0.83924(19) -0.01247(9) 0.37175(15) 0.1050(7) Uani 1 1 d . . .
F1 F 0.50850(17) 0.11993(7) 0.35187(19) 0.0273(4) Uani 1 1 d . . .
O1 O 0.77515(19) 0.18666(8) 1.0990(2) 0.0207(4) Uani 1 1 d . . .
O2 O 1.07698(18) 0.26229(7) 1.0645(2) 0.0160(4) Uani 1 1 d . . .
O3 O 0.92249(19) 0.03837(7) 0.8928(2) 0.0181(4) Uani 1 1 d . . .
N1 N 1.1056(2) 0.07561(8) 1.1221(2) 0.0147(4) Uani 1 1 d . . .
H1 H 1.0761 0.0447 1.0798 0.018 Uiso 1 1 calc R . .
N2 N 1.1131(2) 0.17101(8) 1.1166(2) 0.0120(4) Uani 1 1 d . . .
C1 C 0.6074(3) 0.11137(11) 0.4694(3) 0.0184(5) Uani 1 1 d . . .
C2 C 0.7316(3) 0.13603(10) 0.4621(3) 0.0177(5) Uani 1 1 d . . .
H2 H 0.7488 0.1573 0.3759 0.021 Uiso 1 1 calc R . .
C3 C 0.8314(2) 0.12889(10) 0.5848(3) 0.0152(5) Uani 1 1 d . . .
H3 H 0.9171 0.1463 0.5838 0.018 Uiso 1 1 calc R . .
C4 C 0.8059(2) 0.09627(10) 0.7091(3) 0.0128(4) Uani 1 1 d . . .
C5 C 0.9094(2) 0.08661(10) 0.8437(3) 0.0129(5) Uani 1 1 d . . .
C6 C 0.9824(2) 0.13027(9) 0.9170(3) 0.0120(4) Uani 1 1 d . . .
C7 C 0.9752(2) 0.19144(9) 0.8898(3) 0.0118(4) Uani 1 1 d . . .
H7 H 1.0259 0.1995 0.7999 0.014 Uiso 1 1 calc R . .
C8 C 0.8361(2) 0.21904(10) 0.8611(3) 0.0143(5) Uani 1 1 d . . .
H8A H 0.8474 0.2589 0.8753 0.017 Uiso 1 1 calc R . .
H8B H 0.7985 0.2125 0.7539 0.017 Uiso 1 1 calc R . .
C9 C 0.7364(2) 0.19832(10) 0.9667(3) 0.0142(5) Uani 1 1 d . . .
C10 C 0.5915(2) 0.19083(10) 0.9026(3) 0.0155(5) Uani 1 1 d . . .
C11 C 0.5125(3) 0.15343(11) 0.9741(3) 0.0199(5) Uani 1 1 d . . .
H11 H 0.5486 0.1358 1.0657 0.024 Uiso 1 1 calc R . .
C12 C 0.3810(3) 0.14206(12) 0.9110(3) 0.0243(6) Uani 1 1 d . . .
H12 H 0.3280 0.1159 0.9580 0.029 Uiso 1 1 calc R . .
C13 C 0.3266(3) 0.16899(13) 0.7790(3) 0.0248(6) Uani 1 1 d . . .
H13 H 0.2367 0.1611 0.7362 0.030 Uiso 1 1 calc R . .
C14 C 0.5785(3) 0.07865(11) 0.5891(3) 0.0181(5) Uani 1 1 d . . .
H14 H 0.4920 0.0619 0.5899 0.022 Uiso 1 1 calc R . .
C15 C 0.6800(2) 0.07088(10) 0.7085(3) 0.0151(5) Uani 1 1 d . . .
H15 H 0.6633 0.0478 0.7914 0.018 Uiso 1 1 calc R . .
C16 C 1.0678(2) 0.12179(10) 1.0526(3) 0.0122(4) Uani 1 1 d . . .
C17 C 1.1939(3) 0.07337(10) 1.2658(3) 0.0181(5) Uani 1 1 d . . .
H17A H 1.2896 0.0696 1.2443 0.022 Uiso 1 1 calc R . .
H17B H 1.1702 0.0412 1.3258 0.022 Uiso 1 1 calc R . .
C18 C 1.1774(3) 0.12525(10) 1.3576(3) 0.0191(5) Uani 1 1 d . . .
H18A H 1.0849 0.1265 1.3905 0.023 Uiso 1 1 calc R . .
H18B H 1.2435 0.1251 1.4502 0.023 Uiso 1 1 calc R . .
C19 C 1.2005(3) 0.17532(10) 1.2612(3) 0.0167(5) Uani 1 1 d . . .
H19A H 1.1782 0.2089 1.3162 0.020 Uiso 1 1 calc R . .
H19B H 1.2969 0.1773 1.2412 0.020 Uiso 1 1 calc R . .
C20 C 1.0580(2) 0.21432(9) 1.0312(3) 0.0119(4) Uani 1 1 d . . .
C21 C 0.4034(3) 0.20716(12) 0.7100(3) 0.0240(6) Uani 1 1 d . . .
H21 H 0.3652 0.2262 0.6216 0.029 Uiso 1 1 calc R . .
C22 C 0.5366(3) 0.21773(11) 0.7703(3) 0.0191(5) Uani 1 1 d . . .
H22 H 0.5900 0.2432 0.7214 0.023 Uiso 1 1 calc R . .
C23 C 0.7901(4) 0.02419(18) 0.2063(4) 0.0448(9) Uani 1 1 d . . .
H23A H 0.8498 0.0144 0.1270 0.054 Uiso 1 1 calc R . .
H23B H 0.8013 0.0637 0.2278 0.054 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C23 1.752(4) . ?
Cl2 C23 1.735(4) . ?
F1 C1 1.363(3) . ?
O1 C9 1.220(3) . ?
O2 C20 1.220(3) . ?
O3 C5 1.260(3) . ?
N1 C16 1.321(3) . ?
N1 C17 1.460(3) . ?
N1 H1 0.8800 . ?
N2 C20 1.378(3) . ?
N2 C16 1.385(3) . ?
N2 C19 1.465(3) . ?
C1 C14 1.377(4) . ?
C1 C2 1.378(4) . ?
C2 C3 1.396(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(3) . ?
C3 H3 0.9500 . ?
C4 C15 1.393(3) . ?
C4 C5 1.501(3) . ?
C5 C6 1.408(3) . ?
C6 C16 1.403(3) . ?
C6 C7 1.517(3) . ?
C7 C20 1.523(3) . ?
C7 C8 1.532(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.512(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.498(3) . ?
C10 C11 1.396(4) . ?
C10 C22 1.397(4) . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(4) . ?
C12 H12 0.9500 . ?
C13 C21 1.384(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C17 C18 1.523(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.521(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C21 C22 1.393(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?

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
C16 N1 C17 123.2(2) . . ?
C16 N1 H1 118.4 . . ?
C17 N1 H1 118.4 . . ?
C20 N2 C16 110.82(19) . . ?
C20 N2 C19 125.5(2) . . ?
C16 N2 C19 123.5(2) . . ?
F1 C1 C14 118.6(2) . . ?
F1 C1 C2 118.1(2) . . ?
C14 C1 C2 123.3(2) . . ?
C1 C2 C3 118.2(2) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C15 C4 C3 119.2(2) . . ?
C15 C4 C5 118.0(2) . . ?
C3 C4 C5 122.8(2) . . ?
O3 C5 C6 121.7(2) . . ?
O3 C5 C4 117.1(2) . . ?
C6 C5 C4 121.1(2) . . ?
C16 C6 C5 120.7(2) . . ?
C16 C6 C7 107.1(2) . . ?
C5 C6 C7 131.6(2) . . ?
C6 C7 C20 102.85(18) . . ?
C6 C7 C8 119.22(19) . . ?
C20 C7 C8 111.70(19) . . ?
C6 C7 H7 107.5 . . ?
C20 C7 H7 107.5 . . ?
C8 C7 H7 107.5 . . ?
C9 C8 C7 112.64(19) . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
O1 C9 C10 121.5(2) . . ?
O1 C9 C8 120.3(2) . . ?
C10 C9 C8 118.2(2) . . ?
C11 C10 C22 119.8(2) . . ?
C11 C10 C9 118.1(2) . . ?
C22 C10 C9 122.0(2) . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C21 C13 C12 120.2(3) . . ?
C21 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C1 C14 C15 117.8(2) . . ?
C1 C14 H14 121.1 . . ?
C15 C14 H14 121.1 . . ?
C14 C15 C4 121.2(2) . . ?
C14 C15 H15 119.4 . . ?
C4 C15 H15 119.4 . . ?
N1 C16 N2 119.5(2) . . ?
N1 C16 C6 129.5(2) . . ?
N2 C16 C6 110.9(2) . . ?
N1 C17 C18 109.8(2) . . ?
N1 C17 H17A 109.7 . . ?
C18 C17 H17A 109.7 . . ?
N1 C17 H17B 109.7 . . ?
C18 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C19 C18 C17 110.3(2) . . ?
C19 C18 H18A 109.6 . . ?
C17 C18 H18A 109.6 . . ?
C19 C18 H18B 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
N2 C19 C18 108.4(2) . . ?
N2 C19 H19A 110.0 . . ?
C18 C19 H19A 110.0 . . ?
N2 C19 H19B 110.0 . . ?
C18 C19 H19B 110.0 . . ?
H19A C19 H19B 108.4 . . ?
O2 C20 N2 124.6(2) . . ?
O2 C20 C7 127.3(2) . . ?
N2 C20 C7 108.06(19) . . ?
C13 C21 C22 120.0(3) . . ?
C13 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C10 119.9(3) . . ?
C21 C22 H22 120.0 . . ?
C10 C22 H22 120.0 . . ?
Cl2 C23 Cl1 111.9(2) . . ?
Cl2 C23 H23A 109.2 . . ?
Cl1 C23 H23A 109.2 . . ?
Cl2 C23 H23B 109.2 . . ?
Cl1 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 177.8(2) . . . . ?
C14 C1 C2 C3 -2.2(4) . . . . ?
C1 C2 C3 C4 1.7(4) . . . . ?
C2 C3 C4 C15 0.3(4) . . . . ?
C2 C3 C4 C5 179.4(2) . . . . ?
C15 C4 C5 O3 43.4(3) . . . . ?
C3 C4 C5 O3 -135.8(2) . . . . ?
C15 C4 C5 C6 -132.9(2) . . . . ?
C3 C4 C5 C6 47.9(3) . . . . ?
O3 C5 C6 C16 -3.2(4) . . . . ?
C4 C5 C6 C16 172.9(2) . . . . ?
O3 C5 C6 C7 -173.6(2) . . . . ?
C4 C5 C6 C7 2.5(4) . . . . ?
C16 C6 C7 C20 -3.7(2) . . . . ?
C5 C6 C7 C20 167.6(2) . . . . ?
C16 C6 C7 C8 -127.9(2) . . . . ?
C5 C6 C7 C8 43.4(4) . . . . ?
C6 C7 C8 C9 42.6(3) . . . . ?
C20 C7 C8 C9 -77.2(2) . . . . ?
C7 C8 C9 O1 36.4(3) . . . . ?
C7 C8 C9 C10 -141.5(2) . . . . ?
O1 C9 C10 C11 -22.5(4) . . . . ?
C8 C9 C10 C11 155.4(2) . . . . ?
O1 C9 C10 C22 161.0(2) . . . . ?
C8 C9 C10 C22 -21.1(3) . . . . ?
C22 C10 C11 C12 1.7(4) . . . . ?
C9 C10 C11 C12 -174.8(2) . . . . ?
C10 C11 C12 C13 -1.8(4) . . . . ?
C11 C12 C13 C21 0.0(4) . . . . ?
F1 C1 C14 C15 -179.3(2) . . . . ?
C2 C1 C14 C15 0.7(4) . . . . ?
C1 C14 C15 C4 1.4(4) . . . . ?
C3 C4 C15 C14 -1.9(4) . . . . ?
C5 C4 C15 C14 178.9(2) . . . . ?
C17 N1 C16 N2 0.2(4) . . . . ?
C17 N1 C16 C6 -178.8(2) . . . . ?
C20 N2 C16 N1 -177.3(2) . . . . ?
C19 N2 C16 N1 -1.0(3) . . . . ?
C20 N2 C16 C6 1.9(3) . . . . ?
C19 N2 C16 C6 178.1(2) . . . . ?
C5 C6 C16 N1 8.0(4) . . . . ?
C7 C6 C16 N1 -179.5(2) . . . . ?
C5 C6 C16 N2 -171.0(2) . . . . ?
C7 C6 C16 N2 1.4(3) . . . . ?
C16 N1 C17 C18 27.9(3) . . . . ?
N1 C17 C18 C19 -54.0(3) . . . . ?
C20 N2 C19 C18 149.6(2) . . . . ?
C16 N2 C19 C18 -26.1(3) . . . . ?
C17 C18 C19 N2 52.4(3) . . . . ?
C16 N2 C20 O2 177.3(2) . . . . ?
C19 N2 C20 O2 1.2(4) . . . . ?
C16 N2 C20 C7 -4.3(3) . . . . ?
C19 N2 C20 C7 179.5(2) . . . . ?
C6 C7 C20 O2 -176.9(2) . . . . ?
C8 C7 C20 O2 -47.8(3) . . . . ?
C6 C7 C20 N2 4.9(2) . . . . ?
C8 C7 C20 N2 133.9(2) . . . . ?
C12 C13 C21 C22 1.7(4) . . . . ?
C13 C21 C22 C10 -1.7(4) . . . . ?
C11 C10 C22 C21 0.0(4) . . . . ?
C9 C10 C22 C21 176.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O3 0.88 2.12 2.723(3) 124.7 .
N1 H1 O3 0.88 2.05 2.807(3) 143.8 3_757

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.458
_refine_diff_density_min         -1.284
_refine_diff_density_rms         0.089
####################################################################### 
# 
# 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_global
_database_code_depnum_ccdc_archive 'CCDC 1052294'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H23 Br N2 O4'
_chemical_formula_sum            'C23 H23 Br N2 O4'
_chemical_formula_weight         471.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   7.5265(12)
_cell_length_b                   20.326(3)
_cell_length_c                   13.302(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.255(2)
_cell_angle_gamma                90.00
_cell_volume                     2034.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8471
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      29.77

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    2.054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3486
_exptl_absorpt_correction_T_max  0.7087
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20946
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         29.99
_reflns_number_total             5722
_reflns_number_gt                4854
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0622P)²+15.8182P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5722
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.1922
_refine_ls_wR_factor_gt          0.1866
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.40530(6) 0.37616(2) 0.69540(4) 0.02207(14) Uani 1 1 d . . .
O1 O 0.3480(4) 0.49844(16) 0.9171(2) 0.0185(6) Uani 1 1 d . . .
O2 O 0.2748(4) 0.79376(16) 0.8600(2) 0.0198(6) Uani 1 1 d . . .
H2A H 0.2926 0.7736 0.8061 0.030 Uiso 1 1 calc R . .
O3 O 0.1410(5) 0.60684(17) 0.6798(2) 0.0219(7) Uani 1 1 d . . .
O4 O 0.1903(5) 0.71460(16) 0.7013(2) 0.0229(7) Uani 1 1 d . . .
N1 N 0.3668(5) 0.70151(19) 0.9552(3) 0.0177(7) Uani 1 1 d . . .
N2 N 0.5133(5) 0.60892(19) 0.9765(3) 0.0168(7) Uani 1 1 d . . .
H2B H 0.5479 0.5684 0.9645 0.020 Uiso 1 1 calc R . .
C1 C -0.2141(6) 0.4240(2) 0.7561(3) 0.0176(8) Uani 1 1 d . . .
C2 C -0.2517(6) 0.4710(2) 0.8279(3) 0.0170(8) Uani 1 1 d . . .
H2 H -0.3704 0.4785 0.8480 0.020 Uiso 1 1 calc R . .
C3 C -0.1109(6) 0.5072(2) 0.8702(3) 0.0149(7) Uani 1 1 d . . .
H3 H -0.1345 0.5396 0.9196 0.018 Uiso 1 1 calc R . .
C4 C 0.0636(5) 0.4965(2) 0.8410(3) 0.0142(7) Uani 1 1 d . . .
C5 C 0.2197(5) 0.5328(2) 0.8858(3) 0.0144(7) Uani 1 1 d . . .
C6 C 0.2188(5) 0.6029(2) 0.8924(3) 0.0144(7) Uani 1 1 d . . .
C7 C 0.3615(5) 0.6356(2) 0.9399(3) 0.0142(7) Uani 1 1 d . . .
C8 C 0.2230(6) 0.7484(2) 0.9347(3) 0.0161(8) Uani 1 1 d . . .
C9 C 0.1923(6) 0.7875(2) 1.0315(3) 0.0172(8) Uani 1 1 d . . .
C10 C 0.1528(7) 0.7537(3) 1.1194(4) 0.0233(9) Uani 1 1 d . . .
H10 H 0.1429 0.7071 1.1182 0.028 Uiso 1 1 calc R . .
C11 C 0.1279(7) 0.7874(3) 1.2086(4) 0.0269(10) Uani 1 1 d . . .
H11 H 0.0988 0.7639 1.2677 0.032 Uiso 1 1 calc R . .
C12 C 0.1452(7) 0.8552(3) 1.2118(4) 0.0262(10) Uani 1 1 d . . .
H12 H 0.1283 0.8781 1.2731 0.031 Uiso 1 1 calc R . .
C13 C 0.0975(6) 0.4469(2) 0.7706(3) 0.0168(8) Uani 1 1 d . . .
H13 H 0.2164 0.4379 0.7524 0.020 Uiso 1 1 calc R . .
C14 C -0.0410(6) 0.4108(2) 0.7273(3) 0.0182(8) Uani 1 1 d . . .
H14 H -0.0180 0.3777 0.6788 0.022 Uiso 1 1 calc R . .
C15 C 0.5400(6) 0.7217(2) 0.9981(4) 0.0200(8) Uani 1 1 d . . .
H15A H 0.5263 0.7542 1.0528 0.024 Uiso 1 1 calc R . .
H15B H 0.6175 0.7403 0.9461 0.024 Uiso 1 1 calc R . .
C16 C 0.6129(6) 0.6560(2) 1.0385(3) 0.0182(8) Uani 1 1 d . . .
H16A H 0.7424 0.6521 1.0283 0.022 Uiso 1 1 calc R . .
H16B H 0.5880 0.6503 1.1107 0.022 Uiso 1 1 calc R . .
C17 C 0.1871(7) 0.8895(3) 1.1257(4) 0.0257(10) Uani 1 1 d . . .
H17 H 0.2004 0.9359 1.1279 0.031 Uiso 1 1 calc R . .
C18 C 0.2099(6) 0.8555(2) 1.0346(4) 0.0212(9) Uani 1 1 d . . .
H18 H 0.2374 0.8790 0.9752 0.025 Uiso 1 1 calc R . .
C19 C 0.0544(6) 0.7096(2) 0.9033(3) 0.0158(8) Uani 1 1 d . . .
H19A H -0.0081 0.6967 0.9650 0.019 Uiso 1 1 calc R . .
H19B H -0.0255 0.7395 0.8647 0.019 Uiso 1 1 calc R . .
C20 C 0.0842(5) 0.6478(2) 0.8402(3) 0.0146(7) Uani 1 1 d . . .
H20 H -0.0312 0.6235 0.8353 0.017 Uiso 1 1 calc R . .
C21 C 0.1436(6) 0.6615(2) 0.7341(3) 0.0172(8) Uani 1 1 d . . .
C22 C 0.2062(7) 0.6100(2) 0.5777(4) 0.0233(9) Uani 1 1 d . . .
H22A H 0.3135 0.6380 0.5750 0.028 Uiso 1 1 calc R . .
H22B H 0.1142 0.6283 0.5314 0.028 Uiso 1 1 calc R . .
C23 C 0.2500(9) 0.5399(3) 0.5491(5) 0.0365(13) Uani 1 1 d . . .
H23A H 0.3541 0.5249 0.5883 0.055 Uiso 1 1 calc R . .
H23B H 0.2757 0.5378 0.4773 0.055 Uiso 1 1 calc R . .
H23C H 0.1485 0.5114 0.5632 0.055 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.902(4) . ?
O1 C5 1.255(5) . ?
O2 C8 1.417(5) . ?
O2 H2A 0.8400 . ?
O3 C21 1.324(6) . ?
O3 C22 1.456(6) . ?
O4 C21 1.219(6) . ?
N1 C7 1.355(6) . ?
N1 C8 1.463(6) . ?
N1 C15 1.471(5) . ?
N2 C7 1.346(5) . ?
N2 C16 1.460(6) . ?
N2 H2B 0.8800 . ?
C1 C2 1.385(6) . ?
C1 C14 1.392(6) . ?
C2 C3 1.398(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(6) . ?
C3 H3 0.9500 . ?
C4 C13 1.403(6) . ?
C4 C5 1.501(6) . ?
C5 C6 1.427(6) . ?
C6 C7 1.402(6) . ?
C6 C20 1.520(6) . ?
C8 C9 1.534(6) . ?
C8 C19 1.543(6) . ?
C9 C18 1.389(6) . ?
C9 C10 1.394(6) . ?
C10 C11 1.386(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(8) . ?
C11 H11 0.9500 . ?
C12 C17 1.384(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(6) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.535(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.409(7) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.531(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.516(6) . ?
C20 H20 1.0000 . ?
C22 C23 1.513(7) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C8 O2 H2A 109.5 . . ?
C21 O3 C22 118.1(4) . . ?
C7 N1 C8 126.6(4) . . ?
C7 N1 C15 110.9(4) . . ?
C8 N1 C15 122.5(4) . . ?
C7 N2 C16 111.2(4) . . ?
C7 N2 H2B 124.4 . . ?
C16 N2 H2B 124.4 . . ?
C2 C1 C14 122.0(4) . . ?
C2 C1 Br1 118.8(3) . . ?
C14 C1 Br1 119.2(3) . . ?
C1 C2 C3 118.4(4) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 121.1(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C13 119.0(4) . . ?
C3 C4 C5 123.1(4) . . ?
C13 C4 C5 117.8(4) . . ?
O1 C5 C6 122.7(4) . . ?
O1 C5 C4 116.6(4) . . ?
C6 C5 C4 120.7(4) . . ?
C7 C6 C5 119.8(4) . . ?
C7 C6 C20 114.7(4) . . ?
C5 C6 C20 125.2(4) . . ?
N2 C7 N1 108.8(4) . . ?
N2 C7 C6 127.4(4) . . ?
N1 C7 C6 123.8(4) . . ?
O2 C8 N1 109.9(4) . . ?
O2 C8 C9 107.5(3) . . ?
N1 C8 C9 107.8(3) . . ?
O2 C8 C19 112.3(3) . . ?
N1 C8 C19 108.6(3) . . ?
C9 C8 C19 110.7(4) . . ?
C18 C9 C10 119.1(4) . . ?
C18 C9 C8 121.6(4) . . ?
C10 C9 C8 119.2(4) . . ?
C11 C10 C9 120.7(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 120.3(5) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C17 C12 C11 119.9(5) . . ?
C17 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C4 120.7(4) . . ?
C14 C13 H13 119.7 . . ?
C4 C13 H13 119.7 . . ?
C13 C14 C1 118.8(4) . . ?
C13 C14 H14 120.6 . . ?
C1 C14 H14 120.6 . . ?
N1 C15 C16 101.5(3) . . ?
N1 C15 H15A 111.5 . . ?
C16 C15 H15A 111.5 . . ?
N1 C15 H15B 111.5 . . ?
C16 C15 H15B 111.5 . . ?
H15A C15 H15B 109.3 . . ?
N2 C16 C15 101.4(3) . . ?
N2 C16 H16A 111.5 . . ?
C15 C16 H16A 111.5 . . ?
N2 C16 H16B 111.5 . . ?
C15 C16 H16B 111.5 . . ?
H16A C16 H16B 109.3 . . ?
C12 C17 C18 119.9(5) . . ?
C12 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C9 C18 C17 120.0(5) . . ?
C9 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C8 116.0(3) . . ?
C20 C19 H19A 108.3 . . ?
C8 C19 H19A 108.3 . . ?
C20 C19 H19B 108.3 . . ?
C8 C19 H19B 108.3 . . ?
H19A C19 H19B 107.4 . . ?
C21 C20 C6 109.1(3) . . ?
C21 C20 C19 114.2(4) . . ?
C6 C20 C19 110.3(3) . . ?
C21 C20 H20 107.6 . . ?
C6 C20 H20 107.6 . . ?
C19 C20 H20 107.6 . . ?
O4 C21 O3 123.3(4) . . ?
O4 C21 C20 126.0(4) . . ?
O3 C21 C20 110.7(4) . . ?
O3 C22 C23 105.9(4) . . ?
O3 C22 H22A 110.6 . . ?
C23 C22 H22A 110.6 . . ?
O3 C22 H22B 110.6 . . ?
C23 C22 H22B 110.6 . . ?
H22A C22 H22B 108.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C1 C2 C3 1.7(7) . . . . ?
Br1 C1 C2 C3 -178.3(3) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C3 C4 C13 -2.3(6) . . . . ?
C2 C3 C4 C5 -178.4(4) . . . . ?
C3 C4 C5 O1 129.0(4) . . . . ?
C13 C4 C5 O1 -47.2(6) . . . . ?
C3 C4 C5 C6 -50.6(6) . . . . ?
C13 C4 C5 C6 133.2(4) . . . . ?
O1 C5 C6 C7 -3.4(7) . . . . ?
C4 C5 C6 C7 176.2(4) . . . . ?
O1 C5 C6 C20 168.7(4) . . . . ?
C4 C5 C6 C20 -11.8(6) . . . . ?
C16 N2 C7 N1 12.4(5) . . . . ?
C16 N2 C7 C6 -168.3(4) . . . . ?
C8 N1 C7 N2 -174.4(4) . . . . ?
C15 N1 C7 N2 4.6(5) . . . . ?
C8 N1 C7 C6 6.3(7) . . . . ?
C15 N1 C7 C6 -174.7(4) . . . . ?
C5 C6 C7 N2 5.1(7) . . . . ?
C20 C6 C7 N2 -167.7(4) . . . . ?
C5 C6 C7 N1 -175.7(4) . . . . ?
C20 C6 C7 N1 11.4(6) . . . . ?
C7 N1 C8 O2 -117.1(5) . . . . ?
C15 N1 C8 O2 64.1(5) . . . . ?
C7 N1 C8 C9 126.1(4) . . . . ?
C15 N1 C8 C9 -52.8(5) . . . . ?
C7 N1 C8 C19 6.1(6) . . . . ?
C15 N1 C8 C19 -172.7(4) . . . . ?
O2 C8 C9 C18 2.2(6) . . . . ?
N1 C8 C9 C18 120.6(4) . . . . ?
C19 C8 C9 C18 -120.8(5) . . . . ?
O2 C8 C9 C10 -175.2(4) . . . . ?
N1 C8 C9 C10 -56.8(5) . . . . ?
C19 C8 C9 C10 61.8(5) . . . . ?
C18 C9 C10 C11 1.3(7) . . . . ?
C8 C9 C10 C11 178.7(4) . . . . ?
C9 C10 C11 C12 -1.2(8) . . . . ?
C10 C11 C12 C17 0.2(8) . . . . ?
C3 C4 C13 C14 2.8(6) . . . . ?
C5 C4 C13 C14 179.1(4) . . . . ?
C4 C13 C14 C1 -1.1(7) . . . . ?
C2 C1 C14 C13 -1.2(7) . . . . ?
Br1 C1 C14 C13 178.7(3) . . . . ?
C7 N1 C15 C16 -18.2(5) . . . . ?
C8 N1 C15 C16 160.8(4) . . . . ?
C7 N2 C16 C15 -23.0(5) . . . . ?
N1 C15 C16 N2 23.3(4) . . . . ?
C11 C12 C17 C18 0.8(8) . . . . ?
C10 C9 C18 C17 -0.3(7) . . . . ?
C8 C9 C18 C17 -177.7(4) . . . . ?
C12 C17 C18 C9 -0.7(7) . . . . ?
O2 C8 C19 C20 85.7(4) . . . . ?
N1 C8 C19 C20 -36.0(5) . . . . ?
C9 C8 C19 C20 -154.2(4) . . . . ?
C7 C6 C20 C21 87.2(4) . . . . ?
C5 C6 C20 C21 -85.2(5) . . . . ?
C7 C6 C20 C19 -39.1(5) . . . . ?
C5 C6 C20 C19 148.5(4) . . . . ?
C8 C19 C20 C21 -70.2(5) . . . . ?
C8 C19 C20 C6 53.2(5) . . . . ?
C22 O3 C21 O4 3.4(7) . . . . ?
C22 O3 C21 C20 -175.7(4) . . . . ?
C6 C20 C21 O4 -113.8(5) . . . . ?
C19 C20 C21 O4 10.3(6) . . . . ?
C6 C20 C21 O3 65.3(4) . . . . ?
C19 C20 C21 O3 -170.6(4) . . . . ?
C21 O3 C22 C23 160.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2B O1 0.88 2.21 2.792(5) 123.3 3_667
N2 H2B O1 0.88 2.15 2.678(5) 117.6 .
O2 H2A O4 0.84 1.98 2.719(5) 146.1 .

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        29.99
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         1.936
_refine_diff_density_min         -1.182
_refine_diff_density_rms         0.163
