# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_CS538
_database_code_depnum_ccdc_archive 'CCDC 2071539'
loop_
_audit_author_name
_audit_author_address
'Shiva shivakeshava'
;Tunghai university
Taiwan
;
_audit_update_record             
;
2021-03-19 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H23 N O3'
_chemical_formula_sum            'C19 H23 N O3'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         313.38

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'

_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                   12.8358(6)
_cell_length_b                   9.6075(6)
_cell_length_c                   14.3495(8)
_cell_angle_alpha                90
_cell_angle_beta                 115.331(2)
_cell_angle_gamma                90
_cell_volume                     1599.43(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      3.141
_cell_measurement_theta_max      27.859
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8623
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32456
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.869
_diffrn_reflns_theta_max         27.870
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3793
_reflns_number_gt                3336
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.0615P)²+0.7260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3793
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 0.15719(8) -0.18969(9) 1.06234(7) 0.0279(2) Uani 1 1 d . . . . .
O2 O 0.44266(8) 0.21029(10) 0.91513(7) 0.0284(2) Uani 1 1 d . . . . .
O3 O 0.23223(8) -0.16270(10) 0.74604(7) 0.0270(2) Uani 1 1 d . . . . .
H3A H 0.2062(17) -0.208(2) 0.6874(17) 0.048(5) Uiso 1 1 d . . . . .
N N 0.22210(9) 0.03310(10) 1.08236(7) 0.0193(2) Uani 1 1 d . . . . .
C1 C 0.21399(10) -0.09972(12) 1.04391(8) 0.0198(2) Uani 1 1 d . . . . .
C2 C 0.28021(10) -0.13146(12) 0.98170(9) 0.0209(2) Uani 1 1 d . . . . .
H2A H 0.239334 -0.205389 0.931164 0.025 Uiso 1 1 calc R U . . .
H2B H 0.357112 -0.167935 1.028386 0.025 Uiso 1 1 calc R U . . .
C3 C 0.29584(10) -0.00516(12) 0.92395(8) 0.0176(2) Uani 1 1 d . . . . .
H3B H 0.358599 -0.027890 0.902692 0.021 Uiso 1 1 calc R U . . .
C4 C 0.33702(9) 0.11451(12) 0.99879(8) 0.0176(2) Uani 1 1 d . . . . .
C5 C 0.41936(10) 0.21299(12) 0.98961(9) 0.0204(2) Uani 1 1 d . . . . .
C6 C 0.47637(11) 0.31426(13) 1.07687(10) 0.0247(3) Uani 1 1 d . . . . .
H6A H 0.509029 0.392327 1.052894 0.030 Uiso 1 1 calc R U . . .
H6B H 0.540758 0.267009 1.133901 0.030 Uiso 1 1 calc R U . . .
C7 C 0.39215(10) 0.37233(12) 1.11738(9) 0.0208(2) Uani 1 1 d . . . . .
C8 C 0.33644(11) 0.25029(12) 1.14859(9) 0.0212(2) Uani 1 1 d . . . . .
H8A H 0.392206 0.214388 1.216296 0.025 Uiso 1 1 calc R U . . .
H8B H 0.268506 0.285372 1.157117 0.025 Uiso 1 1 calc R U . . .
C9 C 0.29879(9) 0.13166(11) 1.07248(8) 0.0169(2) Uani 1 1 d . . . . .
C10 C 0.18779(10) 0.02867(11) 0.82640(8) 0.0169(2) Uani 1 1 d . . . . .
C11 C 0.16068(10) -0.05354(12) 0.73823(9) 0.0186(2) Uani 1 1 d . . . . .
C12 C 0.06406(10) -0.02451(13) 0.64676(9) 0.0217(2) Uani 1 1 d . . . . .
H12A H 0.046555 -0.081231 0.587707 0.026 Uiso 1 1 calc R U . . .
C13 C -0.00639(10) 0.08718(14) 0.64210(9) 0.0242(3) Uani 1 1 d . . . . .
H13A H -0.071495 0.107835 0.579488 0.029 Uiso 1 1 calc R U . . .
C14 C 0.01795(11) 0.16878(14) 0.72860(10) 0.0258(3) Uani 1 1 d . . . . .
H14A H -0.030701 0.244761 0.725720 0.031 Uiso 1 1 calc R U . . .
C15 C 0.11397(10) 0.13865(13) 0.81950(9) 0.0223(2) Uani 1 1 d . . . . .
H15A H 0.129795 0.194553 0.878652 0.027 Uiso 1 1 calc R U . . .
C16 C 0.29894(13) 0.45971(14) 1.03426(11) 0.0293(3) Uani 1 1 d . . . . .
H16A H 0.256356 0.401669 0.973594 0.044 Uiso 1 1 calc R U . . .
H16B H 0.245724 0.495972 1.061054 0.044 Uiso 1 1 calc R U . . .
H16C H 0.334984 0.537508 1.014862 0.044 Uiso 1 1 calc R U . . .
C17 C 0.45765(14) 0.46411(15) 1.21127(11) 0.0340(3) Uani 1 1 d . . . . .
H17A H 0.517660 0.408995 1.265041 0.051 Uiso 1 1 calc R U . . .
H17B H 0.493303 0.541891 1.191431 0.051 Uiso 1 1 calc R U . . .
H17C H 0.404043 0.500355 1.237622 0.051 Uiso 1 1 calc R U . . .
C18 C 0.15265(11) 0.06442(14) 1.14008(10) 0.0256(3) Uani 1 1 d . . . . .
H18A H 0.081358 0.007844 1.111251 0.031 Uiso 1 1 calc R U . . .
H18B H 0.129788 0.163676 1.129909 0.031 Uiso 1 1 calc R U . . .
C19 C 0.21603(13) 0.03554(15) 1.25465(10) 0.0318(3) Uani 1 1 d . . . . .
H19A H 0.165918 0.058157 1.288326 0.048 Uiso 1 1 calc R U . . .
H19B H 0.237342 -0.063080 1.265518 0.048 Uiso 1 1 calc R U . . .
H19C H 0.285809 0.092870 1.284191 0.048 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 C1 1.2303(15) . ?
O2 C5 1.2271(14) . ?
O3 C11 1.3667(14) . ?
O3 H3A 0.88(2) . ?
N C1 1.3764(15) . ?
N C9 1.4160(14) . ?
N C18 1.4843(15) . ?
C1 C2 1.5038(16) . ?
C2 C3 1.5303(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5063(15) . ?
C3 C10 1.5255(15) . ?
C3 H3B 1.0000 . ?
C4 C9 1.3529(15) . ?
C4 C5 1.4659(16) . ?
C5 C6 1.5054(17) . ?
C6 C7 1.5346(17) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C16 1.5290(17) . ?
C7 C17 1.5266(17) . ?
C7 C8 1.5366(16) . ?
C8 C9 1.5078(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C15 1.3943(16) . ?
C10 C11 1.4032(15) . ?
C11 C12 1.3948(16) . ?
C12 C13 1.3865(18) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3859(18) . ?
C13 H13A 0.9500 . ?
C14 C15 1.3888(17) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.5156(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C11 O3 H3A 109.7(13) . . ?
C1 N C9 121.10(10) . . ?
C1 N C18 116.82(10) . . ?
C9 N C18 121.97(10) . . ?
O1 C1 N 121.02(11) . . ?
O1 C1 C2 121.50(11) . . ?
N C1 C2 117.45(10) . . ?
C1 C2 C3 113.52(9) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C10 113.30(9) . . ?
C4 C3 C2 107.85(9) . . ?
C10 C3 C2 112.80(9) . . ?
C4 C3 H3B 107.5 . . ?
C10 C3 H3B 107.5 . . ?
C2 C3 H3B 107.5 . . ?
C9 C4 C5 120.55(10) . . ?
C9 C4 C3 121.08(10) . . ?
C5 C4 C3 118.37(10) . . ?
O2 C5 C4 121.22(11) . . ?
O2 C5 C6 121.69(11) . . ?
C4 C5 C6 117.06(10) . . ?
C5 C6 C7 112.31(10) . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C16 C7 C17 108.84(11) . . ?
C16 C7 C8 109.87(10) . . ?
C17 C7 C8 109.43(10) . . ?
C16 C7 C6 110.31(10) . . ?
C17 C7 C6 109.45(11) . . ?
C8 C7 C6 108.91(10) . . ?
C9 C8 C7 114.24(9) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C4 C9 N 119.80(10) . . ?
C4 C9 C8 123.18(10) . . ?
N C9 C8 117.01(9) . . ?
C15 C10 C11 117.63(10) . . ?
C15 C10 C3 123.37(10) . . ?
C11 C10 C3 119.00(10) . . ?
O3 C11 C12 121.76(10) . . ?
O3 C11 C10 117.34(10) . . ?
C12 C11 C10 120.91(11) . . ?
C13 C12 C11 119.94(11) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C12 C13 C14 120.15(11) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C15 C14 C13 119.52(11) . . ?
C15 C14 H14A 120.2 . . ?
C13 C14 H14A 120.2 . . ?
C14 C15 C10 121.85(11) . . ?
C14 C15 H15A 119.1 . . ?
C10 C15 H15A 119.1 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 C17 H17A 109.5 . . ?
C7 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C7 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N C18 C19 113.36(11) . . ?
N C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
N C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C9 N C1 O1 171.86(11) . . . . ?
C18 N C1 O1 -4.29(16) . . . . ?
C9 N C1 C2 -6.18(15) . . . . ?
C18 N C1 C2 177.67(10) . . . . ?
O1 C1 C2 C3 152.28(11) . . . . ?
N C1 C2 C3 -29.69(14) . . . . ?
C1 C2 C3 C4 47.90(12) . . . . ?
C1 C2 C3 C10 -77.98(12) . . . . ?
C10 C3 C4 C9 89.69(13) . . . . ?
C2 C3 C4 C9 -35.90(14) . . . . ?
C10 C3 C4 C5 -89.96(12) . . . . ?
C2 C3 C4 C5 144.45(10) . . . . ?
C9 C4 C5 O2 -169.85(11) . . . . ?
C3 C4 C5 O2 9.80(17) . . . . ?
C9 C4 C5 C6 11.91(16) . . . . ?
C3 C4 C5 C6 -168.44(10) . . . . ?
O2 C5 C6 C7 141.00(12) . . . . ?
C4 C5 C6 C7 -40.77(15) . . . . ?
C5 C6 C7 C16 -65.10(13) . . . . ?
C5 C6 C7 C17 175.17(11) . . . . ?
C5 C6 C7 C8 55.56(13) . . . . ?
C16 C7 C8 C9 77.14(13) . . . . ?
C17 C7 C8 C9 -163.41(11) . . . . ?
C6 C7 C8 C9 -43.79(13) . . . . ?
C5 C4 C9 N -177.99(10) . . . . ?
C3 C4 C9 N 2.37(16) . . . . ?
C5 C4 C9 C8 0.22(17) . . . . ?
C3 C4 C9 C8 -179.43(10) . . . . ?
C1 N C9 C4 21.29(16) . . . . ?
C18 N C9 C4 -162.76(11) . . . . ?
C1 N C9 C8 -157.02(10) . . . . ?
C18 N C9 C8 18.93(15) . . . . ?
C7 C8 C9 C4 17.15(16) . . . . ?
C7 C8 C9 N -164.60(10) . . . . ?
C4 C3 C10 C15 -19.09(15) . . . . ?
C2 C3 C10 C15 103.80(13) . . . . ?
C4 C3 C10 C11 160.40(10) . . . . ?
C2 C3 C10 C11 -76.71(13) . . . . ?
C15 C10 C11 O3 -178.85(10) . . . . ?
C3 C10 C11 O3 1.63(15) . . . . ?
C15 C10 C11 C12 0.87(17) . . . . ?
C3 C10 C11 C12 -178.65(10) . . . . ?
O3 C11 C12 C13 179.94(11) . . . . ?
C10 C11 C12 C13 0.23(17) . . . . ?
C11 C12 C13 C14 -1.01(18) . . . . ?
C12 C13 C14 C15 0.65(19) . . . . ?
C13 C14 C15 C10 0.50(19) . . . . ?
C11 C10 C15 C14 -1.24(18) . . . . ?
C3 C10 C15 C14 178.25(11) . . . . ?
C1 N C18 C19 89.97(13) . . . . ?
C9 N C18 C19 -86.14(14) . . . . ?

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.045

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_CS607
_database_code_depnum_ccdc_archive 'CCDC 2071542'
loop_
_audit_author_name
_audit_author_address
'Shiva shivakeshava'
;Tunghai university
Taiwan
;
_audit_update_record             
;
2021-03-19 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 Br N2 O3'
_chemical_formula_weight         349.18

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                   11.7353(7)
_cell_length_b                   12.0789(8)
_cell_length_c                   10.6288(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.410(2)
_cell_angle_gamma                90
_cell_volume                     1459.23(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9890
_cell_measurement_theta_min      2.864
_cell_measurement_theta_max      27.886

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.828
_shelx_estimated_absorpt_T_min   0.390
_shelx_estimated_absorpt_T_max   0.728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7145
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25829
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.426
_diffrn_reflns_theta_max         27.901
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3469
_reflns_number_gt                3059
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.0508P)²+0.8071P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3469
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
Br1 Br 0.36543(2) -0.12112(2) 0.05173(2) 0.02894(9) Uani 1 1 d . . . . .
O1 O 0.01705(12) -0.10594(11) 0.39212(13) 0.0232(3) Uani 1 1 d . . . . .
O2 O 0.49269(12) 0.16831(13) 0.48390(14) 0.0299(3) Uani 1 1 d . . . . .
O3 O 0.47004(12) 0.07437(14) 0.29691(13) 0.0303(3) Uani 1 1 d . . . . .
N1 N 0.15778(14) 0.01759(13) 0.48767(15) 0.0211(3) Uani 1 1 d . . . . .
H1A H 0.109(2) 0.0425(19) 0.525(2) 0.024(6) Uiso 1 1 d . . . . .
N2 N 0.13470(16) -0.28743(15) 0.19645(18) 0.0335(4) Uani 1 1 d . . . . .
C1 C 0.11768(15) -0.07183(15) 0.41177(17) 0.0193(3) Uani 1 1 d . . . . .
C2 C 0.21215(16) -0.12676(14) 0.35866(17) 0.0190(3) Uani 1 1 d . . . . .
H2A H 0.268160 -0.162267 0.434356 0.023 Uiso 1 1 calc R U . . .
C3 C 0.28404(15) -0.04029(14) 0.30352(16) 0.0180(3) Uani 1 1 d . . . . .
H3A H 0.354823 -0.079096 0.288669 0.022 Uiso 1 1 calc R U . . .
C4 C 0.32760(15) 0.04611(14) 0.40790(16) 0.0190(3) Uani 1 1 d . . . . .
C5 C 0.26588(15) 0.07087(15) 0.49576(17) 0.0201(3) Uani 1 1 d . . . . .
C6 C 0.16550(16) -0.21590(15) 0.26666(18) 0.0226(4) Uani 1 1 d . . . . .
C7 C 0.21891(15) 0.01020(14) 0.17444(16) 0.0182(3) Uani 1 1 d . . . . .
C8 C 0.12938(16) 0.08830(15) 0.16830(18) 0.0222(3) Uani 1 1 d . . . . .
H8A H 0.108284 0.108639 0.245843 0.027 Uiso 1 1 calc R U . . .
C9 C 0.07085(17) 0.13661(16) 0.0518(2) 0.0266(4) Uani 1 1 d . . . . .
H9A H 0.009630 0.188454 0.050152 0.032 Uiso 1 1 calc R U . . .
C10 C 0.1012(2) 0.10965(16) -0.0619(2) 0.0290(4) Uani 1 1 d . . . . .
H10A H 0.062424 0.144216 -0.141342 0.035 Uiso 1 1 calc R U . . .
C11 C 0.18854(18) 0.03191(17) -0.05956(18) 0.0280(4) Uani 1 1 d . . . . .
H11A H 0.208778 0.011551 -0.137579 0.034 Uiso 1 1 calc R U . . .
C12 C 0.24626(16) -0.01602(15) 0.05780(17) 0.0212(3) Uani 1 1 d . . . . .
C13 C 0.43762(16) 0.10428(15) 0.40475(18) 0.0217(4) Uani 1 1 d . . . . .
C14 C 0.57209(19) 0.12587(18) 0.2713(2) 0.0314(5) Uani 1 1 d . . . . .
H14A H 0.585404 0.096506 0.190203 0.047 Uiso 1 1 calc R U . . .
H14B H 0.559792 0.206066 0.263277 0.047 Uiso 1 1 calc R U . . .
H14C H 0.640808 0.110212 0.342966 0.047 Uiso 1 1 calc R U . . .
C15 C 0.29823(18) 0.15372(17) 0.60389(19) 0.0266(4) Uani 1 1 d . . . . .
H15A H 0.237464 0.154602 0.652595 0.040 Uiso 1 1 calc R U . . .
H15B H 0.373958 0.133311 0.662181 0.040 Uiso 1 1 calc R U . . .
H15C H 0.304404 0.227398 0.567538 0.040 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
Br1 C12 1.9017(18) . ?
O1 C1 1.219(2) . ?
O2 C13 1.205(2) . ?
O3 C13 1.344(2) . ?
O3 C14 1.434(2) . ?
N1 C1 1.360(2) . ?
N1 C5 1.406(2) . ?
N1 H1A 0.83(2) . ?
N2 C6 1.140(3) . ?
C1 C2 1.516(2) . ?
C2 C6 1.466(2) . ?
C2 C3 1.547(2) . ?
C2 H2A 1.0000 . ?
C3 C4 1.516(2) . ?
C3 C7 1.522(2) . ?
C3 H3A 1.0000 . ?
C4 C5 1.350(2) . ?
C4 C13 1.478(2) . ?
C5 C15 1.500(2) . ?
C7 C12 1.392(2) . ?
C7 C8 1.401(2) . ?
C8 C9 1.387(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.381(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.386(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.389(3) . ?
C11 H11A 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C13 O3 C14 118.18(16) . . ?
C1 N1 C5 125.00(15) . . ?
C1 N1 H1A 113.0(16) . . ?
C5 N1 H1A 121.8(16) . . ?
O1 C1 N1 123.20(16) . . ?
O1 C1 C2 123.74(16) . . ?
N1 C1 C2 113.02(15) . . ?
C6 C2 C1 112.55(15) . . ?
C6 C2 C3 113.05(15) . . ?
C1 C2 C3 111.34(14) . . ?
C6 C2 H2A 106.5 . . ?
C1 C2 H2A 106.5 . . ?
C3 C2 H2A 106.5 . . ?
C4 C3 C7 112.71(14) . . ?
C4 C3 C2 107.69(14) . . ?
C7 C3 C2 114.41(14) . . ?
C4 C3 H3A 107.2 . . ?
C7 C3 H3A 107.2 . . ?
C2 C3 H3A 107.2 . . ?
C5 C4 C13 122.18(16) . . ?
C5 C4 C3 121.16(15) . . ?
C13 C4 C3 116.62(15) . . ?
C4 C5 N1 119.18(16) . . ?
C4 C5 C15 126.93(16) . . ?
N1 C5 C15 113.88(15) . . ?
N2 C6 C2 176.6(2) . . ?
C12 C7 C8 116.62(16) . . ?
C12 C7 C3 122.43(15) . . ?
C8 C7 C3 120.94(15) . . ?
C9 C8 C7 121.59(18) . . ?
C9 C8 H8A 119.2 . . ?
C7 C8 H8A 119.2 . . ?
C10 C9 C8 120.27(18) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C9 C10 C11 119.63(18) . . ?
C9 C10 H10A 120.2 . . ?
C11 C10 H10A 120.2 . . ?
C12 C11 C10 119.48(18) . . ?
C12 C11 H11A 120.3 . . ?
C10 C11 H11A 120.3 . . ?
C11 C12 C7 122.40(17) . . ?
C11 C12 Br1 116.50(14) . . ?
C7 C12 Br1 121.10(13) . . ?
O2 C13 O3 123.46(17) . . ?
O2 C13 C4 127.52(17) . . ?
O3 C13 C4 109.02(15) . . ?
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 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C5 N1 C1 O1 -168.77(17) . . . . ?
C5 N1 C1 C2 13.4(3) . . . . ?
O1 C1 C2 C6 8.0(2) . . . . ?
N1 C1 C2 C6 -174.20(15) . . . . ?
O1 C1 C2 C3 136.08(18) . . . . ?
N1 C1 C2 C3 -46.1(2) . . . . ?
C6 C2 C3 C4 -179.59(14) . . . . ?
C1 C2 C3 C4 52.57(18) . . . . ?
C6 C2 C3 C7 54.3(2) . . . . ?
C1 C2 C3 C7 -73.58(18) . . . . ?
C7 C3 C4 C5 97.2(2) . . . . ?
C2 C3 C4 C5 -29.9(2) . . . . ?
C7 C3 C4 C13 -80.34(19) . . . . ?
C2 C3 C4 C13 152.52(15) . . . . ?
C13 C4 C5 N1 175.66(16) . . . . ?
C3 C4 C5 N1 -1.8(3) . . . . ?
C13 C4 C5 C15 -2.7(3) . . . . ?
C3 C4 C5 C15 179.84(17) . . . . ?
C1 N1 C5 C4 11.9(3) . . . . ?
C1 N1 C5 C15 -169.48(17) . . . . ?
C4 C3 C7 C12 129.06(17) . . . . ?
C2 C3 C7 C12 -107.45(19) . . . . ?
C4 C3 C7 C8 -49.4(2) . . . . ?
C2 C3 C7 C8 74.1(2) . . . . ?
C12 C7 C8 C9 0.2(3) . . . . ?
C3 C7 C8 C9 178.72(17) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
C8 C9 C10 C11 1.6(3) . . . . ?
C9 C10 C11 C12 -1.5(3) . . . . ?
C10 C11 C12 C7 0.7(3) . . . . ?
C10 C11 C12 Br1 -179.63(16) . . . . ?
C8 C7 C12 C11 -0.1(3) . . . . ?
C3 C7 C12 C11 -178.55(17) . . . . ?
C8 C7 C12 Br1 -179.73(13) . . . . ?
C3 C7 C12 Br1 1.8(2) . . . . ?
C14 O3 C13 O2 -3.4(3) . . . . ?
C14 O3 C13 C4 176.89(16) . . . . ?
C5 C4 C13 O2 9.3(3) . . . . ?
C3 C4 C13 O2 -173.13(19) . . . . ?
C5 C4 C13 O3 -171.02(17) . . . . ?
C3 C4 C13 O3 6.5(2) . . . . ?

_refine_diff_density_max         0.764
_refine_diff_density_min         -0.790
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_CS577
_database_code_depnum_ccdc_archive 'CCDC 2071541'
loop_
_audit_author_name
_audit_author_address
'Shiva shivakeshava'
;Tunghai university
Taiwan
;
_audit_update_record             
;
2021-03-19 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H14 N2 O3'
_chemical_formula_sum            'C15 H14 N2 O3'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         270.28

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'

_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                   13.4631(9)
_cell_length_b                   11.5917(7)
_cell_length_c                   8.6603(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.303(3)
_cell_angle_gamma                90
_cell_volume                     1351.51(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9583
_cell_measurement_theta_min      2.936
_cell_measurement_theta_max      27.864
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8966
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25167
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.936
_diffrn_reflns_theta_max         27.895
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3201
_reflns_number_gt                2804
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.1075P)²+0.7499P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3201
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1767
_refine_ls_wR_factor_gt          0.1681
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
O1 O 0.10198(8) 0.60346(10) 0.99830(12) 0.0279(3) Uani 1 1 d . . . . .
O2 O 0.23767(12) 0.45322(13) 0.34834(14) 0.0476(4) Uani 1 1 d . . . . .
O3 O 0.11027(15) 0.3352(2) 0.3609(2) 0.0813(7) Uani 1 1 d . . . . .
N1 N 0.06377(10) 0.47195(11) 0.81459(15) 0.0249(3) Uani 1 1 d . . . . .
H1A H 0.0149(15) 0.4466(17) 0.876(2) 0.026(5) Uiso 1 1 d . . . . .
N2 N 0.31053(13) 0.75164(15) 0.8949(2) 0.0479(5) Uani 1 1 d . . . . .
C1 C 0.11428(10) 0.56427(12) 0.86845(16) 0.0221(3) Uani 1 1 d . . . . .
C2 C 0.18341(11) 0.61976(12) 0.75145(17) 0.0237(3) Uani 1 1 d . . . . .
H2A H 0.141406 0.671799 0.686158 0.028 Uiso 1 1 calc R U . . .
C3 C 0.23216(11) 0.53187(12) 0.64031(17) 0.0240(3) Uani 1 1 d . . . . .
H3A H 0.258564 0.576272 0.550437 0.029 Uiso 1 1 calc R U . . .
C4 C 0.15177(11) 0.45204(13) 0.57923(16) 0.0240(3) Uani 1 1 d . . . . .
C5 C 0.07357(11) 0.42373(12) 0.66692(17) 0.0237(3) Uani 1 1 d . . . . .
C6 C 0.25528(12) 0.69365(14) 0.8316(2) 0.0309(4) Uani 1 1 d . . . . .
C7 C 0.31875(11) 0.46690(14) 0.7120(2) 0.0290(4) Uani 1 1 d . . . . .
C8 C 0.30610(13) 0.37461(16) 0.8117(2) 0.0329(4) Uani 1 1 d . . . . .
H8A H 0.240933 0.349511 0.836555 0.039 Uiso 1 1 calc R U . . .
C9 C 0.38781(16) 0.3182(2) 0.8760(2) 0.0473(5) Uani 1 1 d . . . . .
H9A H 0.378139 0.256393 0.946377 0.057 Uiso 1 1 calc R U . . .
C10 C 0.48185(17) 0.3517(3) 0.8379(4) 0.0706(9) Uani 1 1 d . . . . .
H10A H 0.537693 0.313634 0.881890 0.085 Uiso 1 1 calc R U . . .
C11 C 0.49522(19) 0.4417(3) 0.7347(6) 0.0949(13) Uani 1 1 d . . . . .
H11A H 0.560520 0.463615 0.705798 0.114 Uiso 1 1 calc R U . . .
C12 C 0.41452(16) 0.4998(2) 0.6734(4) 0.0656(8) Uani 1 1 d . . . . .
H12A H 0.424663 0.562503 0.604552 0.079 Uiso 1 1 calc R U . . .
C13 C 0.16205(14) 0.40577(15) 0.42117(19) 0.0318(4) Uani 1 1 d . . . . .
C14 C 0.2527(2) 0.4200(2) 0.1895(2) 0.0521(6) Uani 1 1 d . . . . .
H14A H 0.310647 0.460664 0.148447 0.078 Uiso 1 1 calc R U . . .
H14B H 0.263970 0.336549 0.183902 0.078 Uiso 1 1 calc R U . . .
H14C H 0.193741 0.440115 0.128441 0.078 Uiso 1 1 calc R U . . .
C15 C -0.00796(12) 0.33988(15) 0.6314(2) 0.0317(4) Uani 1 1 d . . . . .
H15A H -0.054636 0.337540 0.717741 0.048 Uiso 1 1 calc R U . . .
H15B H -0.043041 0.364241 0.537434 0.048 Uiso 1 1 calc R U . . .
H15C H 0.020437 0.262951 0.615599 0.048 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 C1 1.2249(18) . ?
O2 C13 1.320(2) . ?
O2 C14 1.444(2) . ?
O3 C13 1.193(2) . ?
N1 C1 1.3498(19) . ?
N1 C5 1.4025(19) . ?
N1 H1A 0.90(2) . ?
N2 C6 1.141(2) . ?
C1 C2 1.522(2) . ?
C2 C6 1.464(2) . ?
C2 C3 1.550(2) . ?
C2 H2A 1.0000 . ?
C3 C7 1.518(2) . ?
C3 C4 1.517(2) . ?
C3 H3A 1.0000 . ?
C4 C5 1.342(2) . ?
C4 C13 1.477(2) . ?
C5 C15 1.497(2) . ?
C7 C12 1.387(3) . ?
C7 C8 1.386(3) . ?
C8 C9 1.393(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.367(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.386(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.382(4) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C13 O2 C14 117.15(17) . . ?
C1 N1 C5 125.55(13) . . ?
C1 N1 H1A 115.0(13) . . ?
C5 N1 H1A 119.0(13) . . ?
O1 C1 N1 122.75(13) . . ?
O1 C1 C2 122.72(13) . . ?
N1 C1 C2 114.45(12) . . ?
C6 C2 C1 109.68(12) . . ?
C6 C2 C3 113.44(12) . . ?
C1 C2 C3 113.46(12) . . ?
C6 C2 H2A 106.6 . . ?
C1 C2 H2A 106.6 . . ?
C3 C2 H2A 106.6 . . ?
C7 C3 C4 112.64(12) . . ?
C7 C3 C2 113.51(12) . . ?
C4 C3 C2 108.29(12) . . ?
C7 C3 H3A 107.4 . . ?
C4 C3 H3A 107.4 . . ?
C2 C3 H3A 107.4 . . ?
C5 C4 C13 120.87(14) . . ?
C5 C4 C3 120.81(13) . . ?
C13 C4 C3 118.32(13) . . ?
C4 C5 N1 119.76(14) . . ?
C4 C5 C15 128.23(14) . . ?
N1 C5 C15 111.96(13) . . ?
N2 C6 C2 179.31(18) . . ?
C12 C7 C8 118.70(18) . . ?
C12 C7 C3 118.52(18) . . ?
C8 C7 C3 122.77(14) . . ?
C7 C8 C9 120.79(18) . . ?
C7 C8 H8A 119.6 . . ?
C9 C8 H8A 119.6 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C9 C10 C11 119.6(2) . . ?
C9 C10 H10A 120.2 . . ?
C11 C10 H10A 120.2 . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C11 C12 C7 120.2(3) . . ?
C11 C12 H12A 119.9 . . ?
C7 C12 H12A 119.9 . . ?
O3 C13 O2 121.78(16) . . ?
O3 C13 C4 126.65(17) . . ?
O2 C13 C4 111.57(15) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C5 N1 C1 O1 179.27(14) . . . . ?
C5 N1 C1 C2 2.6(2) . . . . ?
O1 C1 C2 C6 20.57(19) . . . . ?
N1 C1 C2 C6 -162.74(13) . . . . ?
O1 C1 C2 C3 148.57(14) . . . . ?
N1 C1 C2 C3 -34.74(18) . . . . ?
C6 C2 C3 C7 47.68(17) . . . . ?
C1 C2 C3 C7 -78.35(16) . . . . ?
C6 C2 C3 C4 173.55(13) . . . . ?
C1 C2 C3 C4 47.52(16) . . . . ?
C7 C3 C4 C5 93.84(17) . . . . ?
C2 C3 C4 C5 -32.54(19) . . . . ?
C7 C3 C4 C13 -85.82(16) . . . . ?
C2 C3 C4 C13 147.80(13) . . . . ?
C13 C4 C5 N1 -177.80(13) . . . . ?
C3 C4 C5 N1 2.5(2) . . . . ?
C13 C4 C5 C15 4.9(2) . . . . ?
C3 C4 C5 C15 -174.76(14) . . . . ?
C1 N1 C5 C4 15.0(2) . . . . ?
C1 N1 C5 C15 -167.26(14) . . . . ?
C4 C3 C7 C12 133.88(19) . . . . ?
C2 C3 C7 C12 -102.6(2) . . . . ?
C4 C3 C7 C8 -44.7(2) . . . . ?
C2 C3 C7 C8 78.83(18) . . . . ?
C12 C7 C8 C9 2.0(3) . . . . ?
C3 C7 C8 C9 -179.38(15) . . . . ?
C7 C8 C9 C10 -1.7(3) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 1.8(5) . . . . ?
C10 C11 C12 C7 -1.5(5) . . . . ?
C8 C7 C12 C11 -0.5(4) . . . . ?
C3 C7 C12 C11 -179.1(3) . . . . ?
C14 O2 C13 O3 2.7(3) . . . . ?
C14 O2 C13 C4 -176.77(16) . . . . ?
C5 C4 C13 O3 -6.2(3) . . . . ?
C3 C4 C13 O3 173.4(2) . . . . ?
C5 C4 C13 O2 173.20(15) . . . . ?
C3 C4 C13 O2 -7.1(2) . . . . ?

_refine_diff_density_max         0.403
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.056

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_CS629
_database_code_depnum_ccdc_archive 'CCDC 2088154'
loop_
_audit_author_name
_audit_author_address
'Shiva shivakeshava'
;Tunghai university
Taiwan
;
_audit_update_record             
;
2021-06-05 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H15 Cl N2 O4'
_chemical_formula_sum            'C17 H15 Cl N2 O4'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         346.76

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'
Cl Cl 0.1484 0.1585 '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                   7.5619(5)
_cell_length_b                   7.8517(5)
_cell_length_c                   26.9250(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.461(3)
_cell_angle_gamma                90
_cell_volume                     1588.49(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9068
_cell_measurement_theta_min      2.703
_cell_measurement_theta_max      27.895
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.265
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6291
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28899
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.704
_diffrn_reflns_theta_max         27.894
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3767
_reflns_number_gt                3594
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.0385P)²+0.9220P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3767
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0898
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
Cl1 Cl 1.31222(4) 0.59815(4) 1.03029(2) 0.02135(9) Uani 1 1 d . . . . .
O1 O 0.70994(12) 1.01709(12) 0.88520(3) 0.0232(2) Uani 1 1 d . . . . .
O2 O 0.52025(12) 0.85152(14) 0.92188(4) 0.0276(2) Uani 1 1 d . . . . .
O3 O 0.83084(12) 0.67385(12) 0.70562(3) 0.0217(2) Uani 1 1 d . . . . .
O4 O 0.59384(12) 0.56350(14) 0.75882(3) 0.0270(2) Uani 1 1 d . . . . .
N1 N 1.00921(13) 0.75609(13) 1.02034(4) 0.0169(2) Uani 1 1 d . . . . .
N2 N 1.33237(15) 0.47294(16) 0.90196(4) 0.0260(2) Uani 1 1 d . . . . .
C1 C 1.10586(15) 0.65653(14) 0.94324(4) 0.0150(2) Uani 1 1 d . . . . .
C2 C 1.12449(15) 0.67786(15) 0.99517(4) 0.0157(2) Uani 1 1 d . . . . .
C3 C 0.86231(15) 0.82198(15) 0.99436(4) 0.0153(2) Uani 1 1 d . . . . .
C4 C 0.83369(15) 0.81322(14) 0.94216(4) 0.0144(2) Uani 1 1 d . . . . .
C5 C 0.95565(15) 0.72870(14) 0.91544(4) 0.0140(2) Uani 1 1 d . . . . .
C6 C 0.92836(15) 0.71263(15) 0.86014(4) 0.0148(2) Uani 1 1 d . . . . .
C7 C 1.05729(15) 0.76905(15) 0.83134(4) 0.0172(2) Uani 1 1 d . . . . .
H7A H 1.165614 0.814924 0.847097 0.021 Uiso 1 1 calc R U . . .
C8 C 1.02898(15) 0.75891(16) 0.77925(4) 0.0179(2) Uani 1 1 d . . . . .
H8A H 1.117344 0.799454 0.759750 0.021 Uiso 1 1 calc R U . . .
C9 C 0.87260(15) 0.68997(15) 0.75591(4) 0.0166(2) Uani 1 1 d . . . . .
C10 C 0.74122(15) 0.63113(16) 0.78517(4) 0.0171(2) Uani 1 1 d . . . . .
C11 C 0.76876(15) 0.64343(15) 0.83684(4) 0.0162(2) Uani 1 1 d . . . . .
H11A H 0.679799 0.605102 0.856473 0.019 Uiso 1 1 calc R U . . .
C12 C 1.23276(15) 0.55654(16) 0.91975(4) 0.0177(2) Uani 1 1 d . . . . .
C13 C 0.73378(17) 0.90628(17) 1.02514(5) 0.0206(2) Uani 1 1 d . . . . .
H13A H 0.646(3) 0.830(3) 1.0316(7) 0.044(5) Uiso 1 1 d . . . . .
H13B H 0.675(2) 1.003(2) 1.0087(7) 0.034(5) Uiso 1 1 d . . . . .
H13C H 0.798(3) 0.941(3) 1.0572(8) 0.046(5) Uiso 1 1 d . . . . .
C14 C 0.66892(15) 0.89308(15) 0.91563(4) 0.0167(2) Uani 1 1 d . . . . .
C15 C 0.5594(2) 1.0990(2) 0.85686(6) 0.0357(4) Uani 1 1 d . . . . .
H15A H 0.602040 1.187987 0.835635 0.054 Uiso 1 1 calc R U . . .
H15B H 0.491335 1.014339 0.835886 0.054 Uiso 1 1 calc R U . . .
H15C H 0.482954 1.150090 0.879894 0.054 Uiso 1 1 calc R U . . .
C16 C 0.96291(19) 0.7252(2) 0.67462(5) 0.0286(3) Uani 1 1 d . . . . .
H16A H 0.917594 0.707668 0.639444 0.043 Uiso 1 1 calc R U . . .
H16B H 0.990793 0.845994 0.680336 0.043 Uiso 1 1 calc R U . . .
H16C H 1.070868 0.657128 0.682835 0.043 Uiso 1 1 calc R U . . .
C17 C 0.44460(17) 0.5310(2) 0.78520(5) 0.0277(3) Uani 1 1 d . . . . .
H17A H 0.347707 0.482751 0.762257 0.042 Uiso 1 1 calc R U . . .
H17B H 0.478412 0.450168 0.812344 0.042 Uiso 1 1 calc R U . . .
H17C H 0.404859 0.637807 0.799189 0.042 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
Cl1 C2 1.7318(11) . ?
O1 C14 1.3315(15) . ?
O1 C15 1.4476(16) . ?
O2 C14 1.2005(16) . ?
O3 C9 1.3613(14) . ?
O3 C16 1.4298(16) . ?
O4 C10 1.3599(14) . ?
O4 C17 1.4226(16) . ?
N1 C2 1.3151(16) . ?
N1 C3 1.3476(15) . ?
N2 C12 1.1440(17) . ?
C1 C2 1.3996(16) . ?
C1 C5 1.4071(15) . ?
C1 C12 1.4402(16) . ?
C3 C4 1.3995(16) . ?
C3 C13 1.5003(16) . ?
C4 C5 1.3992(15) . ?
C4 C14 1.5018(15) . ?
C5 C6 1.4854(15) . ?
C6 C7 1.3851(16) . ?
C6 C11 1.4054(16) . ?
C7 C8 1.3970(16) . ?
C7 H7A 0.9500 . ?
C8 C9 1.3852(17) . ?
C8 H8A 0.9500 . ?
C9 C10 1.4132(16) . ?
C10 C11 1.3868(16) . ?
C11 H11A 0.9500 . ?
C13 H13A 0.93(2) . ?
C13 H13B 0.961(19) . ?
C13 H13C 0.98(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C14 O1 C15 115.17(11) . . ?
C9 O3 C16 117.09(10) . . ?
C10 O4 C17 117.33(10) . . ?
C2 N1 C3 117.85(10) . . ?
C2 C1 C5 117.89(10) . . ?
C2 C1 C12 120.46(10) . . ?
C5 C1 C12 121.59(10) . . ?
N1 C2 C1 124.94(10) . . ?
N1 C2 Cl1 115.95(9) . . ?
C1 C2 Cl1 119.11(9) . . ?
N1 C3 C4 121.86(10) . . ?
N1 C3 C13 115.46(10) . . ?
C4 C3 C13 122.67(11) . . ?
C5 C4 C3 120.21(10) . . ?
C5 C4 C14 120.87(10) . . ?
C3 C4 C14 118.91(10) . . ?
C4 C5 C1 117.19(10) . . ?
C4 C5 C6 122.03(10) . . ?
C1 C5 C6 120.78(10) . . ?
C7 C6 C11 119.80(10) . . ?
C7 C6 C5 120.46(10) . . ?
C11 C6 C5 119.72(10) . . ?
C6 C7 C8 120.39(11) . . ?
C6 C7 H7A 119.8 . . ?
C8 C7 H7A 119.8 . . ?
C9 C8 C7 120.28(11) . . ?
C9 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
O3 C9 C8 125.33(11) . . ?
O3 C9 C10 115.16(10) . . ?
C8 C9 C10 119.51(10) . . ?
O4 C10 C11 124.91(11) . . ?
O4 C10 C9 115.03(10) . . ?
C11 C10 C9 120.06(11) . . ?
C10 C11 C6 119.95(11) . . ?
C10 C11 H11A 120.0 . . ?
C6 C11 H11A 120.0 . . ?
N2 C12 C1 177.90(14) . . ?
C3 C13 H13A 110.1(13) . . ?
C3 C13 H13B 112.9(11) . . ?
H13A C13 H13B 106.7(16) . . ?
C3 C13 H13C 108.9(12) . . ?
H13A C13 H13C 107.9(17) . . ?
H13B C13 H13C 110.2(17) . . ?
O2 C14 O1 124.86(11) . . ?
O2 C14 C4 124.04(11) . . ?
O1 C14 C4 111.09(10) . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C3 N1 C2 C1 -0.47(18) . . . . ?
C3 N1 C2 Cl1 179.16(8) . . . . ?
C5 C1 C2 N1 2.19(18) . . . . ?
C12 C1 C2 N1 -174.84(11) . . . . ?
C5 C1 C2 Cl1 -177.42(9) . . . . ?
C12 C1 C2 Cl1 5.55(16) . . . . ?
C2 N1 C3 C4 -1.91(17) . . . . ?
C2 N1 C3 C13 178.71(11) . . . . ?
N1 C3 C4 C5 2.51(17) . . . . ?
C13 C3 C4 C5 -178.16(11) . . . . ?
N1 C3 C4 C14 -178.58(11) . . . . ?
C13 C3 C4 C14 0.76(17) . . . . ?
C3 C4 C5 C1 -0.69(17) . . . . ?
C14 C4 C5 C1 -179.59(10) . . . . ?
C3 C4 C5 C6 178.47(11) . . . . ?
C14 C4 C5 C6 -0.42(17) . . . . ?
C2 C1 C5 C4 -1.49(16) . . . . ?
C12 C1 C5 C4 175.51(11) . . . . ?
C2 C1 C5 C6 179.34(11) . . . . ?
C12 C1 C5 C6 -3.67(17) . . . . ?
C4 C5 C6 C7 124.46(13) . . . . ?
C1 C5 C6 C7 -56.41(16) . . . . ?
C4 C5 C6 C11 -54.01(16) . . . . ?
C1 C5 C6 C11 125.12(12) . . . . ?
C11 C6 C7 C8 0.55(17) . . . . ?
C5 C6 C7 C8 -177.92(11) . . . . ?
C6 C7 C8 C9 -0.94(18) . . . . ?
C16 O3 C9 C8 3.05(18) . . . . ?
C16 O3 C9 C10 -177.47(11) . . . . ?
C7 C8 C9 O3 179.95(11) . . . . ?
C7 C8 C9 C10 0.48(18) . . . . ?
C17 O4 C10 C11 11.76(19) . . . . ?
C17 O4 C10 C9 -168.82(12) . . . . ?
O3 C9 C10 O4 1.39(16) . . . . ?
C8 C9 C10 O4 -179.09(11) . . . . ?
O3 C9 C10 C11 -179.16(11) . . . . ?
C8 C9 C10 C11 0.36(18) . . . . ?
O4 C10 C11 C6 178.64(11) . . . . ?
C9 C10 C11 C6 -0.75(18) . . . . ?
C7 C6 C11 C10 0.30(17) . . . . ?
C5 C6 C11 C10 178.78(11) . . . . ?
C15 O1 C14 O2 -2.69(18) . . . . ?
C15 O1 C14 C4 178.42(11) . . . . ?
C5 C4 C14 O2 118.35(14) . . . . ?
C3 C4 C14 O2 -60.56(17) . . . . ?
C5 C4 C14 O1 -62.74(14) . . . . ?
C3 C4 C14 O1 118.35(12) . . . . ?

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.047

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_CS619
_database_code_depnum_ccdc_archive 'CCDC 2078427'
loop_
_audit_author_name
_audit_author_address
'Shiva shivakeshava'
;Tunghai university
Taiwan
;
_audit_update_record             
;
2021-04-19 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H16 Br N O4'
_chemical_formula_sum            'C15 H16 Br N O4'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         354.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

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

_cell_length_a                   9.2266(7)
_cell_length_b                   8.5709(7)
_cell_length_c                   18.4502(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.636(4)
_cell_angle_gamma                90
_cell_volume                     1457.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      3.396
_cell_measurement_theta_max      27.988
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.836
_shelx_estimated_absorpt_T_min   0.331
_shelx_estimated_absorpt_T_max   0.601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4626
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27590
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.246
_diffrn_reflns_theta_max         28.108
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3525
_reflns_number_gt                3111
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.1067P)²+0.8336P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3525
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1483
_refine_ls_wR_factor_gt          0.1410
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
Br Br 0.00581(3) 0.17503(3) 0.55819(2) 0.02401(15) Uani 1 1 d . . . . .
O1 O 0.5880(2) 0.8610(3) 0.71265(11) 0.0244(4) Uani 1 1 d . . . . .
O2 O 0.4451(2) 0.6476(3) 0.37595(12) 0.0276(5) Uani 1 1 d . . . . .
O3 O 0.5927(3) 0.8370(3) 0.33903(11) 0.0271(5) Uani 1 1 d . . . . .
O4 O 0.0596(2) 0.8365(2) 0.66522(12) 0.0203(4) Uani 1 1 d . . . . .
H4A H 0.001(5) 0.846(4) 0.696(2) 0.020(9) Uiso 1 1 d . . . . .
N N 0.5796(3) 0.8353(3) 0.59055(13) 0.0166(5) Uani 1 1 d . . . . .
C1 C 0.5229(3) 0.8118(3) 0.65760(14) 0.0174(5) Uani 1 1 d . . . . .
C2 C 0.3831(3) 0.7242(4) 0.66236(14) 0.0216(6) Uani 1 1 d . . . . .
H2A H 0.326412 0.771246 0.701045 0.026 Uiso 1 1 calc R U . . .
H2B H 0.405078 0.614993 0.676485 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2900(3) 0.7238(3) 0.59137(13) 0.0159(5) Uani 1 1 d . . . . .
H3A H 0.258477 0.833290 0.580488 0.019 Uiso 1 1 calc R U . . .
C4 C 0.3868(3) 0.6698(3) 0.53181(15) 0.0183(5) Uani 1 1 d . . . . .
H4B H 0.419883 0.561874 0.542259 0.022 Uiso 1 1 calc R U . . .
H4C H 0.330103 0.668767 0.484920 0.022 Uiso 1 1 calc R U . . .
C5 C 0.5166(3) 0.7740(3) 0.52570(13) 0.0150(5) Uani 1 1 d . . . . .
C6 C 0.7124(3) 0.9283(4) 0.58859(15) 0.0202(5) Uani 1 1 d . . . . .
H6A H 0.698(4) 1.030(5) 0.559(2) 0.032(10) Uiso 1 1 d . . . . .
H6B H 0.787(4) 0.865(5) 0.572(2) 0.029(9) Uiso 1 1 d . . . . .
H6C H 0.739(4) 0.963(5) 0.637(2) 0.035(10) Uiso 1 1 d . . . . .
C7 C 0.5781(3) 0.8106(3) 0.46221(15) 0.0177(5) Uani 1 1 d . . . . .
H7A H 0.659683 0.878301 0.464518 0.021 Uiso 1 1 calc R U . . .
C8 C 0.5278(3) 0.7533(3) 0.39061(14) 0.0185(5) Uani 1 1 d . . . . .
C9 C 0.5544(5) 0.7929(5) 0.26516(17) 0.0361(8) Uani 1 1 d . . . . .
H9A H 0.606345 0.859508 0.231876 0.054 Uiso 1 1 calc R U . . .
H9B H 0.581133 0.683638 0.257566 0.054 Uiso 1 1 calc R U . . .
H9C H 0.449592 0.805480 0.255869 0.054 Uiso 1 1 calc R U . . .
C10 C 0.1556(3) 0.6248(3) 0.60064(13) 0.0148(5) Uani 1 1 d . . . . .
C11 C 0.0431(3) 0.6876(3) 0.64087(14) 0.0162(5) Uani 1 1 d . . . . .
C12 C -0.0799(3) 0.5994(3) 0.65383(14) 0.0189(5) Uani 1 1 d . . . . .
H12A H -0.155852 0.643794 0.680135 0.023 Uiso 1 1 calc R U . . .
C13 C -0.0924(3) 0.4475(3) 0.62868(14) 0.0196(5) Uani 1 1 d . . . . .
H13A H -0.175601 0.386630 0.637940 0.024 Uiso 1 1 calc R U . . .
C14 C 0.0190(3) 0.3865(3) 0.58975(13) 0.0164(5) Uani 1 1 d . . . . .
C15 C 0.1422(3) 0.4725(3) 0.57502(14) 0.0168(5) Uani 1 1 d . . . . .
H15A H 0.216533 0.427679 0.547745 0.020 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
Br C14 1.906(3) . ?
O1 C1 1.230(3) . ?
O2 C8 1.207(4) . ?
O3 C8 1.354(3) . ?
O3 C9 1.443(4) . ?
O4 C11 1.360(3) . ?
O4 H4A 0.81(4) . ?
N C1 1.380(3) . ?
N C5 1.408(3) . ?
N C6 1.463(3) . ?
C1 C2 1.499(4) . ?
C2 C3 1.533(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C10 1.519(3) . ?
C3 C4 1.520(4) . ?
C3 H3A 1.0000 . ?
C4 C5 1.503(4) . ?
C4 H4B 0.9900 . ?
C4 H4C 0.9900 . ?
C5 C7 1.362(4) . ?
C6 H6A 1.03(4) . ?
C6 H6B 0.94(4) . ?
C6 H6C 0.96(4) . ?
C7 C8 1.465(4) . ?
C7 H7A 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.392(4) . ?
C10 C11 1.410(4) . ?
C11 C12 1.393(4) . ?
C12 C13 1.385(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.383(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.392(3) . ?
C15 H15A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O3 C9 115.3(2) . . ?
C11 O4 H4A 105(3) . . ?
C1 N C5 123.3(2) . . ?
C1 N C6 117.0(2) . . ?
C5 N C6 119.7(2) . . ?
O1 C1 N 120.0(3) . . ?
O1 C1 C2 120.8(2) . . ?
N C1 C2 119.2(2) . . ?
C1 C2 C3 113.7(2) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C10 C3 C4 114.9(2) . . ?
C10 C3 C2 109.5(2) . . ?
C4 C3 C2 107.1(2) . . ?
C10 C3 H3A 108.4 . . ?
C4 C3 H3A 108.4 . . ?
C2 C3 H3A 108.4 . . ?
C5 C4 C3 111.7(2) . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4C 109.3 . . ?
C3 C4 H4C 109.3 . . ?
H4B C4 H4C 107.9 . . ?
C7 C5 N 118.2(2) . . ?
C7 C5 C4 124.5(2) . . ?
N C5 C4 117.2(2) . . ?
N C6 H6A 113(2) . . ?
N C6 H6B 109(2) . . ?
H6A C6 H6B 113(3) . . ?
N C6 H6C 109(2) . . ?
H6A C6 H6C 104(3) . . ?
H6B C6 H6C 109(3) . . ?
C5 C7 C8 124.8(2) . . ?
C5 C7 H7A 117.6 . . ?
C8 C7 H7A 117.6 . . ?
O2 C8 O3 122.4(2) . . ?
O2 C8 C7 128.7(2) . . ?
O3 C8 C7 108.9(2) . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.7(2) . . ?
C15 C10 C3 123.1(2) . . ?
C11 C10 C3 118.1(2) . . ?
O4 C11 C12 122.2(3) . . ?
O4 C11 C10 117.3(2) . . ?
C12 C11 C10 120.6(2) . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C14 C13 C12 118.5(2) . . ?
C14 C13 H13A 120.8 . . ?
C12 C13 H13A 120.8 . . ?
C13 C14 C15 122.3(2) . . ?
C13 C14 Br 118.6(2) . . ?
C15 C14 Br 119.0(2) . . ?
C10 C15 C14 119.4(2) . . ?
C10 C15 H15A 120.3 . . ?
C14 C15 H15A 120.3 . . ?

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
C5 N C1 O1 175.8(3) . . . . ?
C6 N C1 O1 -3.8(4) . . . . ?
C5 N C1 C2 -3.4(4) . . . . ?
C6 N C1 C2 177.0(3) . . . . ?
O1 C1 C2 C3 158.8(3) . . . . ?
N C1 C2 C3 -22.0(4) . . . . ?
C1 C2 C3 C10 176.8(2) . . . . ?
C1 C2 C3 C4 51.7(3) . . . . ?
C10 C3 C4 C5 179.6(2) . . . . ?
C2 C3 C4 C5 -58.6(3) . . . . ?
C1 N C5 C7 177.1(3) . . . . ?
C6 N C5 C7 -3.4(4) . . . . ?
C1 N C5 C4 -4.0(4) . . . . ?
C6 N C5 C4 175.6(2) . . . . ?
C3 C4 C5 C7 -144.7(3) . . . . ?
C3 C4 C5 N 36.5(3) . . . . ?
N C5 C7 C8 178.4(2) . . . . ?
C4 C5 C7 C8 -0.4(4) . . . . ?
C9 O3 C8 O2 1.0(4) . . . . ?
C9 O3 C8 C7 179.5(3) . . . . ?
C5 C7 C8 O2 -14.3(5) . . . . ?
C5 C7 C8 O3 167.3(3) . . . . ?
C4 C3 C10 C15 19.7(4) . . . . ?
C2 C3 C10 C15 -100.8(3) . . . . ?
C4 C3 C10 C11 -164.1(2) . . . . ?
C2 C3 C10 C11 75.4(3) . . . . ?
C15 C10 C11 O4 179.9(2) . . . . ?
C3 C10 C11 O4 3.6(3) . . . . ?
C15 C10 C11 C12 -0.9(4) . . . . ?
C3 C10 C11 C12 -177.2(2) . . . . ?
O4 C11 C12 C13 -179.5(2) . . . . ?
C10 C11 C12 C13 1.3(4) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C12 C13 C14 Br 177.63(19) . . . . ?
C11 C10 C15 C14 -0.1(4) . . . . ?
C3 C10 C15 C14 176.0(2) . . . . ?
C13 C14 C15 C10 0.6(4) . . . . ?
Br C14 C15 C10 -177.19(18) . . . . ?

_refine_diff_density_max         2.472
_refine_diff_density_min         -1.078
_refine_diff_density_rms         0.162

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2/n
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_CS547A
_database_code_depnum_ccdc_archive 'CCDC 2071540'
loop_
_audit_author_name
_audit_author_address
'Shiva shivakeshava'
;Tunghai university
Taiwan
;
_audit_update_record             
;
2021-03-19 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C14 H15 N O4'
_chemical_formula_sum            'C14 H15 N O4'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         261.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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                   8.0107(5)
_cell_length_b                   14.7221(9)
_cell_length_c                   10.7274(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.468(3)
_cell_angle_gamma                90
_cell_volume                     1235.29(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      3.208
_cell_measurement_theta_max      27.873
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8768
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22665
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.208
_diffrn_reflns_theta_max         27.881
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2930
_reflns_number_gt                2436
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.0780P)²+0.3520P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2930
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
N N -0.02902(14) 0.26862(7) -0.18076(10) 0.0239(2) Uani 1 1 d . . . . .
H0A H -0.020(2) 0.2815(13) -0.2621(18) 0.040(5) Uiso 1 1 d . . . . .
O1 O 0.15199(13) 0.04602(7) 0.17419(9) 0.0285(2) Uani 1 1 d . . . . .
H1A H 0.162(3) -0.0085(16) 0.209(2) 0.057(6) Uiso 1 1 d . . . . .
C1 C 0.09206(16) 0.10259(8) 0.25586(12) 0.0229(3) Uani 1 1 d . . . . .
O2 O -0.13743(13) 0.13216(6) -0.24843(9) 0.0288(2) Uani 1 1 d . . . . .
C2 C 0.08861(17) 0.07642(9) 0.37990(12) 0.0260(3) Uani 1 1 d . . . . .
H2A H 0.125990 0.017365 0.408971 0.031 Uiso 1 1 calc R U . . .
O3 O 0.07239(14) 0.38838(6) -0.34308(9) 0.0316(2) Uani 1 1 d . . . . .
C3 C 0.03099(18) 0.13598(10) 0.46112(13) 0.0294(3) Uani 1 1 d . . . . .
H3A H 0.028674 0.117735 0.545678 0.035 Uiso 1 1 calc R U . . .
O4 O 0.17264(13) 0.52155(6) -0.25368(9) 0.0286(2) Uani 1 1 d . . . . .
C4 C -0.02334(18) 0.22227(9) 0.41910(13) 0.0289(3) Uani 1 1 d . . . . .
H4A H -0.062045 0.263541 0.474820 0.035 Uiso 1 1 calc R U . . .
C5 C -0.02078(17) 0.24805(9) 0.29447(12) 0.0260(3) Uani 1 1 d . . . . .
H5A H -0.058557 0.307189 0.266091 0.031 Uiso 1 1 calc R U . . .
C6 C 0.03582(15) 0.18926(8) 0.21038(11) 0.0212(3) Uani 1 1 d . . . . .
C7 C 0.04065(15) 0.21510(8) 0.07461(11) 0.0210(3) Uani 1 1 d . . . . .
H7A H 0.157491 0.201050 0.060879 0.025 Uiso 1 1 calc R U . . .
C8 C 0.00413(16) 0.31575(8) 0.04363(11) 0.0231(3) Uani 1 1 d . . . . .
H8A H -0.113123 0.330705 0.052767 0.028 Uiso 1 1 calc R U . . .
H8B H 0.085288 0.353672 0.104746 0.028 Uiso 1 1 calc R U . . .
C9 C 0.02147(15) 0.33662(8) -0.09023(11) 0.0219(3) Uani 1 1 d . . . . .
C10 C -0.08914(16) 0.18488(8) -0.15862(12) 0.0225(3) Uani 1 1 d . . . . .
C11 C -0.08930(16) 0.15999(8) -0.02275(12) 0.0234(3) Uani 1 1 d . . . . .
H11A H -0.062715 0.094531 -0.010013 0.028 Uiso 1 1 calc R U . . .
H11B H -0.205138 0.170186 -0.006965 0.028 Uiso 1 1 calc R U . . .
C12 C 0.08201(16) 0.41656(9) -0.12217(12) 0.0244(3) Uani 1 1 d . . . . .
H12A H 0.111150 0.461654 -0.057799 0.029 Uiso 1 1 calc R U . . .
C13 C 0.10545(16) 0.43790(9) -0.25006(12) 0.0244(3) Uani 1 1 d . . . . .
C14 C 0.2106(2) 0.54728(10) -0.37436(14) 0.0330(3) Uani 1 1 d . . . . .
H14A H 0.258686 0.608757 -0.367769 0.050 Uiso 1 1 calc R U . . .
H14B H 0.293637 0.504598 -0.396371 0.050 Uiso 1 1 calc R U . . .
H14C H 0.105437 0.545969 -0.440895 0.050 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
N C10 1.3629(16) . ?
N C9 1.3926(15) . ?
N H0A 0.911(18) . ?
O1 C1 1.3688(16) . ?
O1 H1A 0.88(2) . ?
C1 C2 1.3912(17) . ?
C1 C6 1.4050(17) . ?
O2 C10 1.2327(15) . ?
C2 C3 1.384(2) . ?
C2 H2A 0.9500 . ?
O3 C13 1.2179(16) . ?
C3 C4 1.386(2) . ?
C3 H3A 0.9500 . ?
O4 C13 1.3479(16) . ?
O4 C14 1.4431(16) . ?
C4 C5 1.3942(18) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3946(18) . ?
C5 H5A 0.9500 . ?
C6 C7 1.5139(16) . ?
C7 C8 1.5329(17) . ?
C7 C11 1.5373(17) . ?
C7 H7A 1.0000 . ?
C8 C9 1.5039(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C12 1.3451(18) . ?
C10 C11 1.5031(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.4585(17) . ?
C12 H12A 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C10 N C9 126.09(11) . . ?
C10 N H0A 117.3(12) . . ?
C9 N H0A 116.6(12) . . ?
C1 O1 H1A 107.1(14) . . ?
O1 C1 C2 121.72(11) . . ?
O1 C1 C6 117.44(11) . . ?
C2 C1 C6 120.83(12) . . ?
C1 C2 C3 120.33(12) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 H2A 119.8 . . ?
C4 C3 C2 120.00(12) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C13 O4 C14 115.38(10) . . ?
C3 C4 C5 119.51(13) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
C6 C5 C4 121.70(12) . . ?
C6 C5 H5A 119.1 . . ?
C4 C5 H5A 119.1 . . ?
C5 C6 C1 117.62(11) . . ?
C5 C6 C7 123.07(11) . . ?
C1 C6 C7 119.30(11) . . ?
C6 C7 C8 114.09(10) . . ?
C6 C7 C11 111.52(10) . . ?
C8 C7 C11 107.06(10) . . ?
C6 C7 H7A 108.0 . . ?
C8 C7 H7A 108.0 . . ?
C11 C7 H7A 108.0 . . ?
C9 C8 C7 110.60(10) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C12 C9 N 121.18(11) . . ?
C12 C9 C8 122.32(11) . . ?
N C9 C8 116.50(11) . . ?
O2 C10 N 119.76(12) . . ?
O2 C10 C11 122.59(11) . . ?
N C10 C11 117.63(11) . . ?
C10 C11 C7 112.82(10) . . ?
C10 C11 H11A 109.0 . . ?
C7 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C7 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C9 C12 C13 123.70(12) . . ?
C9 C12 H12A 118.2 . . ?
C13 C12 H12A 118.2 . . ?
O3 C13 O4 122.74(12) . . ?
O3 C13 C12 126.32(12) . . ?
O4 C13 C12 110.93(11) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
O1 C1 C2 C3 178.47(12) . . . . ?
C6 C1 C2 C3 -0.63(19) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C1 -0.50(19) . . . . ?
C4 C5 C6 C7 -179.86(12) . . . . ?
O1 C1 C6 C5 -178.21(11) . . . . ?
C2 C1 C6 C5 0.93(18) . . . . ?
O1 C1 C6 C7 1.18(17) . . . . ?
C2 C1 C6 C7 -179.68(11) . . . . ?
C5 C6 C7 C8 8.83(17) . . . . ?
C1 C6 C7 C8 -170.52(11) . . . . ?
C5 C6 C7 C11 -112.62(13) . . . . ?
C1 C6 C7 C11 68.03(14) . . . . ?
C6 C7 C8 C9 176.72(10) . . . . ?
C11 C7 C8 C9 -59.41(13) . . . . ?
C10 N C9 C12 178.79(12) . . . . ?
C10 N C9 C8 -1.35(18) . . . . ?
C7 C8 C9 C12 -145.31(12) . . . . ?
C7 C8 C9 N 34.83(15) . . . . ?
C9 N C10 O2 176.53(12) . . . . ?
C9 N C10 C11 -4.96(18) . . . . ?
O2 C10 C11 C7 155.49(12) . . . . ?
N C10 C11 C7 -22.97(16) . . . . ?
C6 C7 C11 C10 179.31(10) . . . . ?
C8 C7 C11 C10 53.87(13) . . . . ?
N C9 C12 C13 -2.14(19) . . . . ?
C8 C9 C12 C13 178.01(11) . . . . ?
C14 O4 C13 O3 -2.79(18) . . . . ?
C14 O4 C13 C12 176.41(11) . . . . ?
C9 C12 C13 O3 1.0(2) . . . . ?
C9 C12 C13 O4 -178.14(12) . . . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.043

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/n
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_CS547B
_database_code_depnum_ccdc_archive 'CCDC 2077711'
loop_
_audit_author_name
_audit_author_address
'Shiva shivakeshava'
;Tunghai university
Taiwan
;
_audit_update_record             
;
2021-04-15 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C14 H15 N O4'
_chemical_formula_sum            'C14 H15 N O4'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         261.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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                   9.1578(6)
_cell_length_b                   8.0660(5)
_cell_length_c                   17.2518(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.892(3)
_cell_angle_gamma                90
_cell_volume                     1267.60(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      2.790
_cell_measurement_theta_max      27.893
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6560
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23984
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.374
_diffrn_reflns_theta_max         27.925
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2997
_reflns_number_gt                2743
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.0818P)²+0.3603P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2997
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1273
_refine_ls_wR_factor_gt          0.1230
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_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 0.32957(9) 0.85451(9) 0.10716(4) 0.0186(2) Uani 1 1 d . . . . .
O2 O 0.54777(9) 0.38435(10) 0.08478(5) 0.0211(2) Uani 1 1 d . . . . .
O3 O 0.00947(11) 0.93148(14) 0.08766(7) 0.0424(3) Uani 1 1 d . . . . .
O4 O -0.11372(10) 0.72569(12) 0.02368(6) 0.0333(3) Uani 1 1 d . . . . .
N N 0.37261(10) 0.58074(11) 0.06820(5) 0.0171(2) Uani 1 1 d . . . . .
H0A H 0.3985(17) 0.5943(19) 0.0223(10) 0.026(4) Uiso 1 1 d . . . . .
C1 C 0.42890(11) 0.86792(13) 0.17262(6) 0.0166(2) Uani 1 1 d . . . . .
C2 C 0.51821(12) 1.00795(14) 0.17690(7) 0.0218(2) Uani 1 1 d . . . . .
H2A H 0.509583 1.087441 0.136049 0.026 Uiso 1 1 calc R U . . .
C3 C 0.62013(13) 1.03038(15) 0.24149(8) 0.0270(3) Uani 1 1 d . . . . .
H3A H 0.681562 1.125560 0.244642 0.032 Uiso 1 1 calc R U . . .
C4 C 0.63290(13) 0.91463(16) 0.30155(8) 0.0272(3) Uani 1 1 d . . . . .
H4A H 0.702686 0.930457 0.345596 0.033 Uiso 1 1 calc R U . . .
C5 C 0.54286(13) 0.77574(15) 0.29662(7) 0.0226(3) Uani 1 1 d . . . . .
H5A H 0.551923 0.696621 0.337621 0.027 Uiso 1 1 calc R U . . .
C6 C 0.43913(11) 0.75011(13) 0.23246(6) 0.0168(2) Uani 1 1 d . . . . .
C7 C 0.34251(12) 0.59732(13) 0.22680(6) 0.0180(2) Uani 1 1 d . . . . .
H7A H 0.310593 0.570687 0.279110 0.022 Uiso 1 1 calc R U . . .
C8 C 0.42446(13) 0.44926(13) 0.19648(6) 0.0200(2) Uani 1 1 d . . . . .
H8A H 0.518969 0.434917 0.229166 0.024 Uiso 1 1 calc R U . . .
H8B H 0.365612 0.347538 0.201381 0.024 Uiso 1 1 calc R U . . .
C9 C 0.45400(11) 0.47015(13) 0.11254(6) 0.0161(2) Uani 1 1 d . . . . .
C10 C 0.26351(11) 0.69355(13) 0.09431(6) 0.0163(2) Uani 1 1 d . . . . .
C11 C 0.20863(12) 0.62944(14) 0.16875(6) 0.0186(2) Uani 1 1 d . . . . .
H11A H 0.143702 0.712458 0.189931 0.022 Uiso 1 1 calc R U . . .
H11B H 0.152252 0.525702 0.158282 0.022 Uiso 1 1 calc R U . . .
C12 C 0.14246(12) 0.71537(15) 0.02723(7) 0.0221(3) Uani 1 1 d . . . . .
H12A H 0.182574 0.777775 -0.015227 0.027 Uiso 1 1 calc R U . . .
H12B H 0.112111 0.604723 0.006607 0.027 Uiso 1 1 calc R U . . .
C13 C 0.00862(13) 0.80560(15) 0.05046(7) 0.0239(3) Uani 1 1 d . . . . .
C14 C -0.24955(15) 0.8037(2) 0.04061(12) 0.0479(4) Uani 1 1 d . . . . .
H14A H -0.332964 0.736482 0.018789 0.072 Uiso 1 1 calc R U . . .
H14B H -0.251107 0.812775 0.097171 0.072 Uiso 1 1 calc R U . . .
H14C H -0.256353 0.914620 0.017325 0.072 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 C1 1.3797(13) . ?
O1 C10 1.4398(12) . ?
O2 C9 1.2370(13) . ?
O3 C13 1.2007(16) . ?
O4 C13 1.3333(15) . ?
O4 C14 1.4503(16) . ?
N C9 1.3488(14) . ?
N C10 1.4565(13) . ?
N H0A 0.857(17) . ?
C1 C2 1.3920(15) . ?
C1 C6 1.3992(15) . ?
C2 C3 1.3901(17) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3906(19) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3884(17) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3979(15) . ?
C5 H5A 0.9500 . ?
C6 C7 1.5144(15) . ?
C7 C11 1.5236(15) . ?
C7 C8 1.5310(15) . ?
C7 H7A 1.0000 . ?
C8 C9 1.5097(14) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C11 1.5172(14) . ?
C10 C12 1.5283(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5144(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C1 O1 C10 115.34(8) . . ?
C13 O4 C14 115.34(10) . . ?
C9 N C10 126.47(9) . . ?
C9 N H0A 114.8(10) . . ?
C10 N H0A 118.0(10) . . ?
O1 C1 C2 116.20(10) . . ?
O1 C1 C6 122.64(9) . . ?
C2 C1 C6 121.16(10) . . ?
C3 C2 C1 119.38(11) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C4 C3 C2 120.53(11) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 119.48(11) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
C4 C5 C6 121.25(11) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C1 C6 C5 118.19(10) . . ?
C1 C6 C7 120.71(9) . . ?
C5 C6 C7 121.09(10) . . ?
C6 C7 C11 109.24(9) . . ?
C6 C7 C8 110.68(9) . . ?
C11 C7 C8 107.32(9) . . ?
C6 C7 H7A 109.9 . . ?
C11 C7 H7A 109.9 . . ?
C8 C7 H7A 109.9 . . ?
C9 C8 C7 112.52(9) . . ?
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 . . ?
O2 C9 N 121.04(9) . . ?
O2 C9 C8 120.58(9) . . ?
N C9 C8 118.35(9) . . ?
O1 C10 N 108.68(8) . . ?
O1 C10 C11 110.33(8) . . ?
N C10 C11 110.25(9) . . ?
O1 C10 C12 105.87(8) . . ?
N C10 C12 107.76(8) . . ?
C11 C10 C12 113.74(9) . . ?
C7 C11 C10 107.47(8) . . ?
C7 C11 H11A 110.2 . . ?
C10 C11 H11A 110.2 . . ?
C7 C11 H11B 110.2 . . ?
C10 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C13 C12 C10 113.51(9) . . ?
C13 C12 H12A 108.9 . . ?
C10 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C10 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
O3 C13 O4 123.58(11) . . ?
O3 C13 C12 125.93(11) . . ?
O4 C13 C12 110.49(10) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C10 O1 C1 C2 165.79(9) . . . . ?
C10 O1 C1 C6 -15.23(14) . . . . ?
O1 C1 C2 C3 179.50(9) . . . . ?
C6 C1 C2 C3 0.51(16) . . . . ?
C1 C2 C3 C4 -0.18(17) . . . . ?
C2 C3 C4 C5 0.02(18) . . . . ?
C3 C4 C5 C6 -0.18(18) . . . . ?
O1 C1 C6 C5 -179.58(9) . . . . ?
C2 C1 C6 C5 -0.66(15) . . . . ?
O1 C1 C6 C7 1.72(15) . . . . ?
C2 C1 C6 C7 -179.36(10) . . . . ?
C4 C5 C6 C1 0.49(16) . . . . ?
C4 C5 C6 C7 179.18(10) . . . . ?
C1 C6 C7 C11 -21.14(13) . . . . ?
C5 C6 C7 C11 160.20(10) . . . . ?
C1 C6 C7 C8 96.81(11) . . . . ?
C5 C6 C7 C8 -81.85(12) . . . . ?
C6 C7 C8 C9 -67.89(12) . . . . ?
C11 C7 C8 C9 51.23(11) . . . . ?
C10 N C9 O2 -177.29(10) . . . . ?
C10 N C9 C8 4.73(16) . . . . ?
C7 C8 C9 O2 162.39(10) . . . . ?
C7 C8 C9 N -19.62(14) . . . . ?
C1 O1 C10 N -72.99(11) . . . . ?
C1 O1 C10 C11 48.01(11) . . . . ?
C1 O1 C10 C12 171.49(8) . . . . ?
C9 N C10 O1 99.03(12) . . . . ?
C9 N C10 C11 -22.01(14) . . . . ?
C9 N C10 C12 -146.68(10) . . . . ?
C6 C7 C11 C10 51.24(11) . . . . ?
C8 C7 C11 C10 -68.80(10) . . . . ?
O1 C10 C11 C7 -67.01(10) . . . . ?
N C10 C11 C7 53.04(11) . . . . ?
C12 C10 C11 C7 174.20(9) . . . . ?
O1 C10 C12 C13 -73.91(11) . . . . ?
N C10 C12 C13 169.94(9) . . . . ?
C11 C10 C12 C13 47.40(13) . . . . ?
C14 O4 C13 O3 1.6(2) . . . . ?
C14 O4 C13 C12 -178.32(12) . . . . ?
C10 C12 C13 O3 47.08(18) . . . . ?
C10 C12 C13 O4 -132.96(11) . . . . ?

_refine_diff_density_max         0.405
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.047

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/n
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

