# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_compound_1a_centro
_database_code_depnum_ccdc_archive 'CCDC 2058507'
loop_
_audit_author_name
_audit_author_address
'Jari Konu'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 Cl N O4'
_chemical_formula_sum            'C16 H14 Cl N O4'
_chemical_formula_weight         319.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.9071(2)
_cell_length_b                   28.2960(6)
_cell_length_c                   7.1173(2)
_cell_angle_alpha                90
_cell_angle_beta                 115.383(4)
_cell_angle_gamma                90
_cell_volume                     1438.69(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3875
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.4630
_cell_measurement_theta_min      6.1870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.524
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 3 4 0.0558
0 -3 -4 0.0708
-5 3 0 0.1016
5 -3 0 0.1016
0 -1 0 0.0396
0 1 0 0.0576

_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.097
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0006 2.9946 4.0023 -0.1964 0.9052 -0.2963
0.0006 -2.9946 -4.0023 0.1964 -0.9052 0.2963
-4.9997 2.9769 -0.0011 0.0365 -0.0969 1.0852
4.9997 -2.9769 0.0011 -0.0365 0.0969 -1.0852
0.0001 -0.9999 -0.0001 0.0535 -0.0015 -0.0101
-0.0001 0.9999 0.0001 -0.0535 0.0015 0.0101

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5734
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.830
_diffrn_reflns_theta_min         6.195
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -121.00 -16.00   1.00    1.00    --  -41.78 -19.00 -90.00  105
  2  ω     63.00  93.00   1.00    1.00    --   41.78-125.00 -90.00   30
  3  ω      1.00  58.00   1.00    1.00    --   41.78 -99.00 150.00   57
  4  ω     91.00 159.00   1.00    1.50    --  112.00  61.00 -90.00   68
  5  ω    106.00 146.00   1.00    1.50    --  112.00 111.00-150.00   40
  6  ω    149.00 178.00   1.00    1.50    --  112.00 111.00-150.00   29
  7  ω     64.00 108.00   1.00    1.50    --  112.00 -94.00 -30.00   44
  8  ω     48.00 132.00   1.00    1.50    --  112.00 -77.00 150.00   84
  9  ω     29.00  55.00   1.00    1.50    --  112.00 -94.00 -30.00   26
 10  ω     39.00 139.00   1.00    1.50    --  112.00 -30.00  90.00  100
 11  ω     43.00 111.00   1.00    1.50    --  112.00-111.00 150.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0391650000
_diffrn_orient_matrix_UB_12      -0.0535032000
_diffrn_orient_matrix_UB_13      -0.0090583000
_diffrn_orient_matrix_UB_21      0.0202250000
_diffrn_orient_matrix_UB_22      0.0014968000
_diffrn_orient_matrix_UB_23      0.2250421000
_diffrn_orient_matrix_UB_31      -0.2110412000
_diffrn_orient_matrix_UB_32      0.0100594000
_diffrn_orient_matrix_UB_33      -0.0815833000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2655
_reflns_number_total             2946
_reflns_odcompleteness_completeness 99.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2946
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0495P)²+0.3548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0940
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.27685(5) 0.57403(2) 0.04819(5) 0.02523(12) Uani 1 1 d . . . . .
O1 O -0.10577(17) 0.31313(4) 0.50954(19) 0.0341(3) Uani 1 1 d . . . . .
O2 O -0.02727(17) 0.32656(4) 0.83571(19) 0.0317(3) Uani 1 1 d . . . . .
O3 O 0.68708(15) 0.70478(4) 0.47326(15) 0.0246(2) Uani 1 1 d . . . . .
O4 O 0.49765(15) 0.65953(4) 0.11322(16) 0.0237(2) Uani 1 1 d . . . . .
N1 N -0.03339(17) 0.33770(4) 0.6660(2) 0.0240(3) Uani 1 1 d . . . . .
C1 C 0.05111(19) 0.38281(5) 0.6512(2) 0.0210(3) Uani 1 1 d . . . . .
C2 C 0.1362(2) 0.40990(5) 0.8292(2) 0.0236(3) Uani 1 1 d . . . . .
H2 H 0.137942 0.400001 0.954594 0.028 Uiso 1 1 calc R . . . .
C3 C 0.2187(2) 0.45209(5) 0.8157(2) 0.0239(3) Uani 1 1 d . . . . .
H3 H 0.277014 0.470585 0.934240 0.029 Uiso 1 1 calc R . . . .
C4 C 0.21668(19) 0.46766(5) 0.6276(2) 0.0205(3) Uani 1 1 d . . . . .
C5 C 0.1266(2) 0.43942(5) 0.4506(2) 0.0216(3) Uani 1 1 d . . . . .
H5 H 0.121969 0.449366 0.323889 0.026 Uiso 1 1 calc R . . . .
C6 C 0.0445(2) 0.39688(5) 0.4616(2) 0.0223(3) Uani 1 1 d . . . . .
H6 H -0.014043 0.378119 0.343971 0.027 Uiso 1 1 calc R . . . .
C7 C 0.3088(2) 0.51248(5) 0.6273(2) 0.0224(3) Uani 1 1 d . . . . .
H7 H 0.380087 0.525965 0.756532 0.027 Uiso 1 1 calc R . . . .
C8 C 0.30153(19) 0.53610(5) 0.4619(2) 0.0211(3) Uani 1 1 d . . . . .
H8 H 0.231986 0.522765 0.331882 0.025 Uiso 1 1 calc R . . . .
C9 C 0.39393(19) 0.58126(5) 0.4680(2) 0.0194(3) Uani 1 1 d . . . . .
C10 C 0.48576(19) 0.60712(5) 0.6524(2) 0.0209(3) Uani 1 1 d . . . . .
H10 H 0.482075 0.596012 0.773585 0.025 Uiso 1 1 calc R . . . .
C11 C 0.58170(19) 0.64858(5) 0.6605(2) 0.0214(3) Uani 1 1 d . . . . .
H11 H 0.641457 0.664680 0.785843 0.026 Uiso 1 1 calc R . . . .
C12 C 0.58888(19) 0.66626(5) 0.4810(2) 0.0203(3) Uani 1 1 d . . . . .
C13 C 0.48993(19) 0.64292(5) 0.2904(2) 0.0197(3) Uani 1 1 d . . . . .
C14 C 0.39574(18) 0.60142(5) 0.2882(2) 0.0189(3) Uani 1 1 d . . . . .
C15 C 0.8112(2) 0.72565(6) 0.6683(2) 0.0283(3) Uani 1 1 d . . . . .
H15A H 0.890652 0.748275 0.644953 0.043 Uiso 1 1 calc GR . . . .
H15B H 0.886711 0.701407 0.760464 0.043 Uiso 1 1 calc GR . . . .
H15C H 0.739044 0.741177 0.729477 0.043 Uiso 1 1 calc GR . . . .
C16 C 0.3759(2) 0.69907(6) 0.0208(2) 0.0308(3) Uani 1 1 d . . . . .
H16A H 0.390392 0.709427 -0.099894 0.046 Uiso 1 1 calc GR . . . .
H16B H 0.407645 0.724446 0.119628 0.046 Uiso 1 1 calc GR . . . .
H16C H 0.248404 0.689742 -0.018921 0.046 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C14 1.7395(14) . ?
O1 N1 1.2268(18) . ?
O2 N1 1.2288(18) . ?
O3 C12 1.3528(17) . ?
O3 C15 1.4389(18) . ?
O4 C13 1.3717(16) . ?
O4 C16 1.4381(19) . ?
N1 C1 1.4656(18) . ?
C1 C2 1.384(2) . ?
C1 C6 1.386(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.403(2) . ?
C4 C5 1.401(2) . ?
C4 C7 1.463(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.333(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.4633(19) . ?
C9 C10 1.403(2) . ?
C9 C14 1.4067(19) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.396(2) . ?
C12 C13 1.406(2) . ?
C13 C14 1.387(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O3 C15 117.22(11) . . ?
C13 O4 C16 113.71(11) . . ?
O1 N1 O2 123.60(13) . . ?
O1 N1 C1 118.54(13) . . ?
O2 N1 C1 117.86(13) . . ?
C2 C1 N1 118.31(13) . . ?
C2 C1 C6 122.20(13) . . ?
C6 C1 N1 119.49(13) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.24(13) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.63(14) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C7 118.13(13) . . ?
C5 C4 C3 118.21(13) . . ?
C5 C4 C7 123.66(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.93(13) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.79(13) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C4 C7 H7 116.5 . . ?
C8 C7 C4 127.08(14) . . ?
C8 C7 H7 116.5 . . ?
C7 C8 H8 117.3 . . ?
C7 C8 C9 125.43(13) . . ?
C9 C8 H8 117.3 . . ?
C10 C9 C8 122.33(13) . . ?
C10 C9 C14 115.87(13) . . ?
C14 C9 C8 121.79(13) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 C9 122.38(13) . . ?
C11 C10 H10 118.8 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.13(13) . . ?
C12 C11 H11 119.9 . . ?
O3 C12 C11 125.12(13) . . ?
O3 C12 C13 115.52(12) . . ?
C11 C12 C13 119.36(13) . . ?
O4 C13 C12 120.01(13) . . ?
O4 C13 C14 121.00(12) . . ?
C14 C13 C12 118.86(13) . . ?
C9 C14 Cl1 120.05(11) . . ?
C13 C14 Cl1 116.73(10) . . ?
C13 C14 C9 123.22(13) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C15 H15A O2 0.96 2.44 3.3338(19) 154.4 2_656 yes
C15 H15C O3 0.96 2.48 3.3731(19) 155.5 4_576 yes

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 N1 C1 C2 -178.58(13) . . . . ?
O1 N1 C1 C6 1.08(19) . . . . ?
O2 N1 C1 C2 1.27(19) . . . . ?
O2 N1 C1 C6 -179.07(13) . . . . ?
O3 C12 C13 O4 0.14(19) . . . . ?
O3 C12 C13 C14 175.91(12) . . . . ?
O4 C13 C14 Cl1 -3.99(18) . . . . ?
O4 C13 C14 C9 175.71(12) . . . . ?
N1 C1 C2 C3 178.91(12) . . . . ?
N1 C1 C6 C5 -179.37(12) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C2 C3 C4 C7 -179.43(13) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C3 C4 C7 C8 -170.64(14) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C4 C7 C8 C9 179.17(13) . . . . ?
C5 C4 C7 C8 9.4(2) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
C7 C4 C5 C6 178.95(13) . . . . ?
C7 C8 C9 C10 -6.9(2) . . . . ?
C7 C8 C9 C14 173.15(14) . . . . ?
C8 C9 C10 C11 176.50(13) . . . . ?
C8 C9 C14 Cl1 3.04(18) . . . . ?
C8 C9 C14 C13 -176.65(13) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C10 C9 C14 Cl1 -176.91(10) . . . . ?
C10 C9 C14 C13 3.4(2) . . . . ?
C10 C11 C12 O3 -175.97(13) . . . . ?
C10 C11 C12 C13 3.3(2) . . . . ?
C11 C12 C13 O4 -179.15(12) . . . . ?
C11 C12 C13 C14 -3.4(2) . . . . ?
C12 C13 C14 Cl1 -179.71(10) . . . . ?
C12 C13 C14 C9 0.0(2) . . . . ?
C14 C9 C10 C11 -3.6(2) . . . . ?
C15 O3 C12 C11 7.9(2) . . . . ?
C15 O3 C12 C13 -171.31(12) . . . . ?
C16 O4 C13 C12 -79.91(16) . . . . ?
C16 O4 C13 C14 104.42(15) . . . . ?


_ins_header                      
;
TITL ek1832_a in P2(1)/c 
REM P2(1)/c (#14 in standard setting)
CELL 1.54184   7.907077  28.296039   7.117279  90.0000 115.3833  90.0000
ZERR    6.00   0.000232   0.000624   0.000202   0.0000   0.0036   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2 
SFAC C H N O
UNIT 66.00 60.00 6.00 6.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.156
_oxdiff_exptl_absorpt_empirical_full_min 0.863
####################################################################### 
# 
# 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_compound_1b
_database_code_depnum_ccdc_archive 'CCDC 2058509'
loop_
_audit_author_name
_audit_author_address
'Jari Konu'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 Br N2 O5'
_chemical_formula_sum            'C14 H9 Br N2 O5'
_chemical_formula_weight         365.14
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H19 N2 O5 Br1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   3.82360(10)
_cell_length_b                   26.8722(5)
_cell_length_c                   13.2409(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.319(2)
_cell_angle_gamma                90
_cell_volume                     1358.20(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3851
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      75.9940
_cell_measurement_theta_min      4.6650
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.174
_exptl_absorpt_coefficient_mu    4.397
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.356
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 2 5 0.0354
-2 2 0 0.2734
0 -2 -5 0.0354
2 -2 0 0.3304
0 10 -1 0.0194
0 -10 1 0.0010

_exptl_crystal_size_max          0.612
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.02
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0005 1.9962 4.9997 -0.0161 0.5759 0.1446
-2.4997 1.5025 -0.0038 -0.0067 0.2064 -0.9910
0.0005 -1.9962 -4.9997 0.0161 -0.5759 -0.1446
2.4997 -1.5025 0.0038 0.0067 -0.2064 0.9910
-0.0015 10.0037 -1.0014 0.5820 0.0262 -0.0560
0.0015 -10.0037 1.0014 -0.5820 -0.0262 0.0560

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5023
_diffrn_reflns_point_group_measured_fraction_full 0.728
_diffrn_reflns_point_group_measured_fraction_max 0.707
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.739
_diffrn_reflns_theta_min         3.289
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  27.00   1.00    1.50    --  -41.65  37.00-150.00   88
  2  ω   -121.00  -1.00   1.00    1.50    --  -41.65 -19.00  30.00  120
  3  ω     25.00  67.00   1.00    1.50    --   41.65-125.00 -60.00   42
  4  ω      1.00  83.00   1.00    1.50    --   41.65 -99.00   0.00   82
  5  ω     68.00  98.00   1.00    1.50    --   41.65-125.00 -60.00   30
  6  ω     77.00 116.00   1.00    7.00    --  112.00-111.00 -30.00   39
  7  ω     68.00 151.00   1.00    7.00    --  112.00 178.00-180.00   83
  8  ω     57.00 151.00   1.00    7.00    --  112.00 178.00-150.00   94
  9  ω     37.00 116.00   1.00    7.00    --  112.00-111.00-180.00   79
 10  ω    150.00 178.00   1.00    7.00    --  112.00  45.00 -30.00   28
 11  ω     41.00 140.00   1.00    7.00    --  112.00 -30.00 150.00   99
 12  ω    133.00 177.00   1.00    7.00    --  112.00  15.00-150.00   44
 13  ω     86.00 132.00   1.00    7.00    --  112.00  45.00 -30.00   46
 14  ω     61.00 115.00   1.00    7.00    --  112.00  15.00-150.00   54
 15  ω     36.00 140.00   1.00    7.00    --  112.00 -77.00-180.00  104
 16  ω     42.00 129.00   1.00    7.00    --  112.00 -61.00 -60.00   87
 17  ω     39.00 140.00   1.00    7.00    --  112.00 -30.00 -60.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0361770000
_diffrn_orient_matrix_UB_12      0.0556393000
_diffrn_orient_matrix_UB_13      -0.0254254000
_diffrn_orient_matrix_UB_21      -0.0745792000
_diffrn_orient_matrix_UB_22      0.0135918000
_diffrn_orient_matrix_UB_23      0.1097502000
_diffrn_orient_matrix_UB_31      0.3948638000
_diffrn_orient_matrix_UB_32      -0.0025351000
_diffrn_orient_matrix_UB_33      0.0299700000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.427
_reflns_Friedel_fraction_full    0.455
_reflns_Friedel_fraction_max     0.426
_reflns_number_gt                1997
_reflns_number_total             2021
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2021
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²+0.8315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0826
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5A), C6(H6), C7(H7), C8(H8), C10(H10), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.69425(9) 0.62154(2) 0.08945(5) 0.03985(16) Uani 1 1 d . . . . .
O1 O -0.0316(10) 0.46383(12) 0.8523(3) 0.0372(8) Uani 1 1 d . . . . .
O2 O -0.1933(10) 0.53490(13) 0.9109(2) 0.0372(7) Uani 1 1 d . . . . .
O3 O 1.1973(10) 0.79594(12) 0.2112(3) 0.0415(8) Uani 1 1 d . . . . .
O4 O 1.0536(14) 0.81217(13) 0.3627(3) 0.0506(10) Uani 1 1 d . . . . .
O5 O 0.7600(10) 0.74591(11) 0.4693(3) 0.0370(7) Uani 1 1 d . . . . .
H5 H 0.834477 0.773949 0.458867 0.056 Uiso 1 1 calc GR . . . .
N1 N -0.0563(9) 0.50962(13) 0.8472(3) 0.0262(7) Uani 1 1 d . . . . .
N2 N 1.0539(12) 0.78476(16) 0.2882(4) 0.0347(10) Uani 1 1 d . . . . .
C1 C 0.0801(10) 0.53429(14) 0.7591(3) 0.0202(7) Uani 1 1 d . . . . .
C2 C 0.0550(10) 0.58577(13) 0.7516(3) 0.0212(7) Uani 1 1 d . . . . .
H2 H -0.039349 0.604419 0.802541 0.025 Uiso 1 1 calc R . . . .
C3 C 0.1735(10) 0.60857(13) 0.6664(3) 0.0209(7) Uani 1 1 d . . . . .
H3 H 0.156835 0.642966 0.659987 0.025 Uiso 1 1 calc R . . . .
C4 C 0.3183(10) 0.58077(12) 0.5898(3) 0.0188(6) Uani 1 1 d . . . . .
C5 C 0.3385(11) 0.52875(13) 0.6002(3) 0.0212(7) Uani 1 1 d . . . . .
H5A H 0.434856 0.509888 0.549912 0.025 Uiso 1 1 calc R . . . .
C6 C 0.2165(10) 0.50520(12) 0.6846(3) 0.0221(7) Uani 1 1 d . . . . .
H6 H 0.226112 0.470751 0.690878 0.027 Uiso 1 1 calc R . . . .
C7 C 0.4514(10) 0.60313(14) 0.4991(3) 0.0205(7) Uani 1 1 d . . . . .
H7 H 0.528177 0.581407 0.450432 0.025 Uiso 1 1 calc R . . . .
C8 C 0.4737(11) 0.65194(14) 0.4792(3) 0.0225(7) Uani 1 1 d . . . . .
H8 H 0.402117 0.674545 0.527035 0.027 Uiso 1 1 calc R . . . .
C9 C 0.6061(10) 0.67104(14) 0.3852(3) 0.0232(7) Uani 1 1 d . . . . .
C10 C 0.5903(11) 0.64293(14) 0.2965(3) 0.0247(7) Uani 1 1 d . . . . .
H10 H 0.490979 0.611335 0.296438 0.030 Uiso 1 1 calc R . . . .
C11 C 0.7213(12) 0.66147(15) 0.2078(3) 0.0269(8) Uani 1 1 d . . . . .
C12 C 0.8695(11) 0.70810(16) 0.2041(3) 0.0298(9) Uani 1 1 d . . . . .
H12 H 0.958204 0.720201 0.145003 0.036 Uiso 1 1 calc R . . . .
C13 C 0.8815(11) 0.73646(15) 0.2923(3) 0.0277(8) Uani 1 1 d . . . . .
C14 C 0.7507(12) 0.71952(16) 0.3829(4) 0.0254(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C11 1.897(4) . ?
O1 N1 1.236(5) . ?
O2 N1 1.224(5) . ?
O3 N2 1.223(6) . ?
O4 N2 1.231(7) . ?
O5 H5 0.8200 . ?
O5 C14 1.345(6) . ?
N1 C1 1.463(4) . ?
N2 C13 1.458(6) . ?
C1 C2 1.390(5) . ?
C1 C6 1.385(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.400(5) . ?
C4 C5 1.406(4) . ?
C4 C7 1.460(5) . ?
C5 H5A 0.9300 . ?
C5 C6 1.388(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.342(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.463(5) . ?
C9 C10 1.395(6) . ?
C9 C14 1.416(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.395(5) . ?
C11 C12 1.377(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.392(7) . ?
C13 C14 1.402(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O5 H5 109.5 . . ?
O1 N1 C1 117.8(4) . . ?
O2 N1 O1 123.3(3) . . ?
O2 N1 C1 119.0(3) . . ?
O3 N2 O4 122.8(4) . . ?
O3 N2 C13 118.3(5) . . ?
O4 N2 C13 118.8(4) . . ?
C2 C1 N1 118.8(3) . . ?
C6 C1 N1 118.6(3) . . ?
C6 C1 C2 122.5(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.1(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 C7 123.2(3) . . ?
C5 C4 C7 118.0(3) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5A 119.6 . . ?
C1 C6 C5 118.3(3) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C4 C7 H7 116.8 . . ?
C8 C7 C4 126.4(3) . . ?
C8 C7 H7 116.8 . . ?
C7 C8 H8 118.7 . . ?
C7 C8 C9 122.6(4) . . ?
C9 C8 H8 118.7 . . ?
C10 C9 C8 121.8(4) . . ?
C10 C9 C14 118.5(4) . . ?
C14 C9 C8 119.7(4) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(4) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 Br1 119.2(3) . . ?
C12 C11 Br1 119.3(3) . . ?
C12 C11 C10 121.5(4) . . ?
C11 C12 H12 121.2 . . ?
C11 C12 C13 117.6(4) . . ?
C13 C12 H12 121.2 . . ?
C12 C13 N2 116.7(4) . . ?
C12 C13 C14 122.9(4) . . ?
C14 C13 N2 120.3(4) . . ?
O5 C14 C9 117.2(4) . . ?
O5 C14 C13 124.3(4) . . ?
C13 C14 C9 118.4(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5 O4 0.82 1.87 2.571(5) 142.4 . yes
C3 H3 O3 0.93 2.53 3.221(5) 131.8 4_365 yes
C7 H7 O1 0.93 2.50 3.372(5) 156.1 2_664 yes

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
Br1 C11 C12 C13 179.4(3) . . . . ?
O1 N1 C1 C2 179.9(4) . . . . ?
O1 N1 C1 C6 2.5(6) . . . . ?
O2 N1 C1 C2 1.1(6) . . . . ?
O2 N1 C1 C6 -176.4(4) . . . . ?
O3 N2 C13 C12 -5.0(6) . . . . ?
O3 N2 C13 C14 172.3(4) . . . . ?
O4 N2 C13 C12 176.1(5) . . . . ?
O4 N2 C13 C14 -6.6(7) . . . . ?
N1 C1 C2 C3 -177.8(3) . . . . ?
N1 C1 C6 C5 178.6(4) . . . . ?
N2 C13 C14 O5 2.5(7) . . . . ?
N2 C13 C14 C9 -175.9(4) . . . . ?
C1 C2 C3 C4 -0.5(6) . . . . ?
C2 C1 C6 C5 1.3(6) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C2 C3 C4 C7 -179.2(4) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C3 C4 C7 C8 4.2(7) . . . . ?
C4 C5 C6 C1 -1.1(6) . . . . ?
C4 C7 C8 C9 -179.0(4) . . . . ?
C5 C4 C7 C8 -175.6(4) . . . . ?
C6 C1 C2 C3 -0.5(6) . . . . ?
C7 C4 C5 C6 -180.0(4) . . . . ?
C7 C8 C9 C10 25.3(6) . . . . ?
C7 C8 C9 C14 -155.5(4) . . . . ?
C8 C9 C10 C11 -179.3(4) . . . . ?
C8 C9 C14 O5 0.3(6) . . . . ?
C8 C9 C14 C13 178.8(4) . . . . ?
C9 C10 C11 Br1 179.8(3) . . . . ?
C9 C10 C11 C12 -0.2(7) . . . . ?
C10 C9 C14 O5 179.5(4) . . . . ?
C10 C9 C14 C13 -2.0(6) . . . . ?
C10 C11 C12 C13 -0.6(7) . . . . ?
C11 C12 C13 N2 177.2(4) . . . . ?
C11 C12 C13 C14 0.0(7) . . . . ?
C12 C13 C14 O5 179.7(4) . . . . ?
C12 C13 C14 C9 1.3(6) . . . . ?
C14 C9 C10 C11 1.5(6) . . . . ?


_ins_header                      
;
TITL ek1917_a_Cc in Cc 
REM Cc (#9 in standard setting)
CELL 1.54184   3.823607  26.872166  13.240861  90.0000  93.3186  90.0000
ZERR    4.00   0.000066   0.000512   0.000247   0.0000   0.0017   0.0000
LATT -7
SYMM  x,-y, z+1/2 
SFAC C H N O Br
UNIT 56.00 76.00 8.00 20.00 4.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.333
_oxdiff_exptl_absorpt_empirical_full_min 0.483
####################################################################### 
# 
# 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_compound_1e
_database_code_depnum_ccdc_archive 'CCDC 2058512'
loop_
_audit_author_name
_audit_author_address
'Jari Konu'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-03-12 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_audit_creation_date             2021-03-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.9378(4)
_cell_length_b                   7.3721(7)
_cell_length_c                   15.3569(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.417(7)
_cell_angle_gamma                90
_cell_volume                     668.02(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1219
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      74.6780
_cell_measurement_theta_min      2.8290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             284
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -6 0.0165
-3 -1 -2 0.0385
0 1 6 0.0175
3 1 2 0.0565
0 -1 0 0.0235
0 1 0 0.0175

_exptl_crystal_size_max          0.126
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.034
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0061 -0.9972 -5.8840 0.1178 -0.1216 -0.6062
-2.9998 -1.0027 -2.3350 0.5547 -0.6510 -0.1521
0.0061 0.9972 5.8840 -0.1178 0.1216 0.6062
2.9998 1.0027 2.3350 -0.5547 0.6510 0.1521
-0.0006 -0.9999 0.0344 0.1770 0.0973 -0.0534
0.0006 0.9999 -0.0344 -0.1770 -0.0973 0.0534

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3947
_diffrn_reflns_point_group_measured_fraction_full 0.813
_diffrn_reflns_point_group_measured_fraction_max 0.780
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.761
_diffrn_reflns_theta_min         2.896
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -95.00 -51.00   1.00   10.00    --  -41.65 125.00-180.00   44
  2  ω    -67.00  24.00   1.00   10.00    --  -41.65  57.00 120.00   91
  3  ω    -66.00  33.00   1.00   10.00    --  -41.65  37.00 -90.00   99
  4  ω   -113.00 -20.00   1.00   10.00    --  -41.65 -57.00 -30.00   93
  5  ω    106.00 163.00   1.00   80.00    --  112.00 111.00 -30.00   57
  6  ω     45.00 116.00   1.00   80.00    --  112.00-111.00  60.00   71
  7  ω     39.00 129.00   1.00   80.00    --  112.00 -77.00-120.00   90
  8  ω     45.00 109.00   1.00   80.00    --  112.00 -94.00-180.00   64
  9  ω    101.00 168.00   1.00   80.00    --  112.00  77.00  60.00   67
 10  ω     49.00 125.00   1.00   80.00    --  112.00 -45.00   0.00   76
 11  ω     82.00 108.00   1.00   80.00    --  112.00  77.00 120.00   26
 12  ω    132.00 176.00   1.00   80.00    --  112.00  77.00 120.00   44
 13  ω     86.00 173.00   1.00   80.00    --  112.00  45.00  30.00   87
 14  ω    102.00 172.00   1.00   80.00    --  112.00  61.00 -60.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1336932000
_diffrn_orient_matrix_UB_12      -0.1766289000
_diffrn_orient_matrix_UB_13      0.0100555000
_diffrn_orient_matrix_UB_21      0.2205563000
_diffrn_orient_matrix_UB_22      -0.0961701000
_diffrn_orient_matrix_UB_23      0.0367385000
_diffrn_orient_matrix_UB_31      -0.0409957000
_diffrn_orient_matrix_UB_32      0.0566809000
_diffrn_orient_matrix_UB_33      0.0934656000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.483
_reflns_Friedel_fraction_full    0.595
_reflns_Friedel_fraction_max     0.553
_reflns_number_gt                1671
_reflns_number_total             2194
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 410 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2194
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0855
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1281P)²+0.3516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2365
_refine_ls_wR_factor_ref         0.2602
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C8B-C7B
 1.3 with sigma of 0.02
 C9-C8B
 1.4 with sigma of 0.02
 C7B-C4
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C8B) = Uanis(C7B)
Uanis(C13B) = Uanis(C14B) = Uanis(C10B) = Uanis(C11B)
Uanis(C13A) = Uanis(C14A) = Uanis(C10A) = Uanis(C11A)
Uanis(O2B) = Uanis(O1B)
Uanis(C3B) = Uanis(C2B) = Uanis(C6B) = Uanis(C5B)
Uanis(C16B) = Uanis(C15B)
Uanis(C5A) = Uanis(C6A) = Uanis(C2A) = Uanis(C3A)
4. Others
 Fixed Sof: O1A(0.6) O2A(0.6) C2A(0.6) H2A(0.6) C3A(0.6) H3A(0.6) C5A(0.6)
 H5A(0.6) C6A(0.6) H6A(0.6) C7A(0.75) H7A(0.75) C8A(0.75) H8A(0.75) C10A(0.6)
 H10A(0.6) C11A(0.6) H11A(0.6) C13A(0.6) H13A(0.6) C14A(0.6) H14A(0.6)
 C15A(0.6) H15A(0.6) H15B(0.6) H15C(0.6) C16A(0.6) H16A(0.6) H16B(0.6)
 H16C(0.6) O1B(0.4) O2B(0.4) C3B(0.4) H3B(0.4) C2B(0.4) H2B(0.4) C6B(0.4)
 H6B(0.4) C5B(0.4) H5B(0.4) C7B(0.25) H7B(0.25) C8B(0.25) H8B(0.25) C11B(0.4)
 H11B(0.4) C10B(0.4) H10B(0.4) C14B(0.4) H14B(0.4) C13B(0.4) H13B(0.4)
 C15B(0.4) H15D(0.4) H15E(0.4) H15F(0.4) C16B(0.4) H16D(0.4) H16E(0.4) H16F(0.4)
5.a Me refined with riding coordinates:
 C15A(H15A,H15B,H15C), C16A(H16A,H16B,H16C), C15B(H15D,H15E,H15F), C16B(H16D,
 H16E,H16F)
5.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C10A(H10A),
 C11A(H11A), C13A(H13A), C14A(H14A), C3B(H3B), C2B(H2B), C6B(H6B), C5B(H5B),
 C7B(H7B), C8B(H8B), C11B(H11B), C10B(H10B), C14B(H14B), C13B(H13B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.1144(6) 1.6311(9) 1.1436(2) 0.0401(9) Uani 1 1 d . . . . .
N2 N 0.4092(5) 1.6271(8) 1.86395(19) 0.0360(8) Uani 1 1 d . . . . .
O1A O 0.9980(15) 1.7130(15) 1.0847(5) 0.066(2) Uani 0.6 1 d . . P A 1
O2A O 1.2888(15) 1.5550(16) 1.1317(7) 0.075(3) Uani 0.6 1 d . . P A 1
C2A C 1.1709(13) 1.5470(11) 1.2969(7) 0.0365(11) Uani 0.6 1 d . . P B 1
H2A H 1.307268 1.494259 1.285979 0.044 Uiso 0.6 1 calc R . P B 1
C3A C 1.1074(14) 1.5425(11) 1.3780(7) 0.0365(11) Uani 0.6 1 d . . P B 1
H3A H 1.199513 1.484518 1.422480 0.044 Uiso 0.6 1 calc R . P B 1
C5A C 0.7612(13) 1.7104(10) 1.3264(7) 0.0365(11) Uani 0.6 1 d . . P B 1
H5A H 0.623012 1.762189 1.335613 0.044 Uiso 0.6 1 calc R . P B 1
C6A C 0.8342(14) 1.7147(10) 1.2436(7) 0.0365(11) Uani 0.6 1 d . . P B 1
H6A H 0.749402 1.774125 1.197601 0.044 Uiso 0.6 1 calc R . P B 1
C7A C 0.8455(8) 1.6140(14) 1.4883(3) 0.0347(14) Uani 0.75 1 d . . P B 1
H7A H 0.965914 1.587822 1.530506 0.042 Uiso 0.75 1 calc R . P B 1
C8A C 0.6484(9) 1.6360(14) 1.5168(3) 0.0331(13) Uani 0.75 1 d . . P B 1
H8A H 0.526467 1.657312 1.474573 0.040 Uiso 0.75 1 calc R . P B 1
C10A C 0.7301(13) 1.5535(11) 1.6729(6) 0.0328(10) Uani 0.6 1 d . . P B 1
H10A H 0.864598 1.499270 1.660887 0.039 Uiso 0.6 1 calc R . P B 1
C11A C 0.6758(14) 1.5495(11) 1.7607(6) 0.0328(10) Uani 0.6 1 d . . P B 1
H11A H 0.773930 1.495199 1.804486 0.039 Uiso 0.6 1 calc R . P B 1
C13A C 0.3360(14) 1.7095(11) 1.7093(6) 0.0328(10) Uani 0.6 1 d . . P B 1
H13A H 0.201271 1.766019 1.719229 0.039 Uiso 0.6 1 calc R . P B 1
C14A C 0.4013(13) 1.7057(11) 1.6239(6) 0.0328(10) Uani 0.6 1 d . . P B 1
H14A H 0.305435 1.756202 1.578276 0.039 Uiso 0.6 1 calc R . P B 1
C15A C 0.2261(17) 1.7418(17) 1.8843(8) 0.049(2) Uani 0.6 1 d . . P C 1
H15A H 0.202295 1.725683 1.944659 0.073 Uiso 0.6 1 calc R . P C 1
H15B H 0.263500 1.866251 1.874405 0.073 Uiso 0.6 1 calc R . P C 1
H15C H 0.090392 1.710073 1.847541 0.073 Uiso 0.6 1 calc R . P C 1
C16A C 0.566(3) 1.564(3) 1.9368(9) 0.076(5) Uani 0.6 1 d . . P C 1
H16A H 0.496194 1.571934 1.990006 0.115 Uiso 0.6 1 calc R . P C 1
H16B H 0.606713 1.440102 1.926867 0.115 Uiso 0.6 1 calc R . P C 1
H16C H 0.700257 1.637877 1.941632 0.115 Uiso 0.6 1 calc R . P C 1
O1B O 0.997(2) 1.5314(18) 1.0857(6) 0.0522(19) Uani 0.4 1 d . . P A 2
O2B O 1.288(2) 1.6973(19) 1.1329(6) 0.0522(19) Uani 0.4 1 d . . P A 2
C3B C 1.091(2) 1.712(2) 1.3807(7) 0.0382(16) Uani 0.4 1 d . . P B 2
H3B H 1.173554 1.774455 1.426332 0.046 Uiso 0.4 1 calc R . P B 2
C2B C 1.172(2) 1.713(2) 1.2972(7) 0.0382(16) Uani 0.4 1 d . . P B 2
H2B H 1.308254 1.768448 1.288023 0.046 Uiso 0.4 1 calc R . P B 2
C1 C 1.0374(6) 1.6281(8) 1.2306(2) 0.0291(8) Uani 1 1 d . . . . .
C6B C 0.837(3) 1.5409(19) 1.2426(7) 0.0382(16) Uani 0.4 1 d . . P B 2
H6B H 0.748567 1.481635 1.197409 0.046 Uiso 0.4 1 calc R . P B 2
C5B C 0.774(2) 1.5493(19) 1.3306(7) 0.0382(16) Uani 0.4 1 d . . P B 2
H5B H 0.637166 1.497440 1.341109 0.046 Uiso 0.4 1 calc R . P B 2
C4 C 0.8995(7) 1.6258(10) 1.3976(3) 0.0399(10) Uani 1 1 d D . . . .
C7B C 0.724(4) 1.658(7) 1.4563(13) 0.087(8) Uani 0.25 1 d D . P B 2
H7B H 0.586562 1.710244 1.434111 0.105 Uiso 0.25 1 calc R . P B 2
C8B C 0.757(4) 1.615(7) 1.5376(14) 0.087(8) Uani 0.25 1 d D . P B 2
H8B H 0.899263 1.567652 1.556356 0.105 Uiso 0.25 1 calc R . P B 2
C11B C 0.681(2) 1.703(2) 1.7625(7) 0.0375(16) Uani 0.4 1 d . . P B 2
H11B H 0.775823 1.752747 1.808707 0.045 Uiso 0.4 1 calc R . P B 2
C10B C 0.750(2) 1.7081(19) 1.6803(7) 0.0375(16) Uani 0.4 1 d . . P B 2
H10B H 0.889063 1.758716 1.671276 0.045 Uiso 0.4 1 calc R . P B 2
C9 C 0.5990(7) 1.6309(9) 1.6062(2) 0.0374(10) Uani 1 1 d D . . . .
C14B C 0.386(2) 1.547(2) 1.6285(7) 0.0375(16) Uani 0.4 1 d . . P B 2
H14B H 0.287038 1.493431 1.584621 0.045 Uiso 0.4 1 calc R . P B 2
C13B C 0.334(2) 1.548(2) 1.7111(8) 0.0375(16) Uani 0.4 1 d . . P B 2
H13B H 0.199660 1.492504 1.723091 0.045 Uiso 0.4 1 calc R . P B 2
C12 C 0.4735(6) 1.6279(8) 1.7804(2) 0.0289(8) Uani 1 1 d . . . . .
C15B C 0.232(3) 1.507(2) 1.8855(8) 0.046(3) Uani 0.4 1 d . . P C 2
H15D H 0.208318 1.523779 1.945804 0.069 Uiso 0.4 1 calc R . P C 2
H15E H 0.094306 1.534539 1.848816 0.069 Uiso 0.4 1 calc R . P C 2
H15F H 0.274854 1.383936 1.876150 0.069 Uiso 0.4 1 calc R . P C 2
C16B C 0.584(3) 1.665(3) 1.9357(10) 0.046(3) Uani 0.4 1 d . . P C 2
H16D H 0.518954 1.660285 1.990205 0.069 Uiso 0.4 1 calc R . P C 2
H16E H 0.701653 1.575393 1.936196 0.069 Uiso 0.4 1 calc R . P C 2
H16F H 0.646067 1.783001 1.928133 0.069 Uiso 0.4 1 calc R . P C 2


_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
N1 O1A 1.233(10) . ?
N1 O2A 1.209(10) . ?
N1 O1B 1.294(14) . ?
N1 O2B 1.168(14) . ?
N1 C1 1.460(4) . ?
N2 C15A 1.439(12) . ?
N2 C16A 1.451(14) . ?
N2 C12 1.379(4) . ?
N2 C15B 1.440(15) . ?
N2 C16B 1.453(17) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.342(13) . ?
C2A C1 1.357(10) . ?
C3A H3A 0.9300 . ?
C3A C4 1.440(9) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.388(13) . ?
C5A C4 1.435(11) . ?
C6A H6A 0.9300 . ?
C6A C1 1.399(9) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.304(7) . ?
C7A C4 1.467(6) . ?
C8A H8A 0.9300 . ?
C8A C9 1.436(6) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.421(12) . ?
C10A C9 1.342(10) . ?
C11A H11A 0.9300 . ?
C11A C12 1.397(9) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.408(12) . ?
C13A C12 1.422(10) . ?
C14A H14A 0.9300 . ?
C14A C9 1.351(10) . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C16A H16A 0.9600 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
C3B H3B 0.9300 . ?
C3B C2B 1.420(14) . ?
C3B C4 1.352(16) . ?
C2B H2B 0.9300 . ?
C2B C1 1.378(14) . ?
C1 C6B 1.385(16) . ?
C6B H6B 0.9300 . ?
C6B C5B 1.441(13) . ?
C5B H5B 0.9300 . ?
C5B C4 1.326(14) . ?
C4 C7B 1.474(16) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.28(2) . ?
C8B H8B 0.9300 . ?
C8B C9 1.492(17) . ?
C11B H11B 0.9300 . ?
C11B C10B 1.370(15) . ?
C11B C12 1.406(14) . ?
C10B H10B 0.9300 . ?
C10B C9 1.482(12) . ?
C9 C14B 1.483(14) . ?
C14B H14B 0.9300 . ?
C14B C13B 1.338(16) . ?
C13B H13B 0.9300 . ?
C13B C12 1.405(14) . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
C16B H16D 0.9600 . ?
C16B H16E 0.9600 . ?
C16B H16F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1A N1 C1 118.1(6) . . ?
O2A N1 O1A 122.4(7) . . ?
O2A N1 C1 119.4(6) . . ?
O1B N1 C1 114.9(6) . . ?
O2B N1 O1B 123.7(8) . . ?
O2B N1 C1 120.4(6) . . ?
C15A N2 C16A 117.2(7) . . ?
C12 N2 C15A 119.6(6) . . ?
C12 N2 C16A 119.8(6) . . ?
C12 N2 C15B 120.1(7) . . ?
C12 N2 C16B 117.2(7) . . ?
C15B N2 C16B 114.9(9) . . ?
C3A C2A H2A 119.8 . . ?
C3A C2A C1 120.4(7) . . ?
C1 C2A H2A 119.8 . . ?
C2A C3A H3A 119.4 . . ?
C2A C3A C4 121.3(8) . . ?
C4 C3A H3A 119.4 . . ?
C6A C5A H5A 120.1 . . ?
C6A C5A C4 119.8(6) . . ?
C4 C5A H5A 120.1 . . ?
C5A C6A H6A 120.6 . . ?
C5A C6A C1 118.9(8) . . ?
C1 C6A H6A 120.6 . . ?
C8A C7A H7A 116.2 . . ?
C8A C7A C4 127.7(5) . . ?
C4 C7A H7A 116.2 . . ?
C7A C8A H8A 116.4 . . ?
C7A C8A C9 127.2(5) . . ?
C9 C8A H8A 116.4 . . ?
C11A C10A H10A 118.0 . . ?
C9 C10A H10A 118.0 . . ?
C9 C10A C11A 124.0(7) . . ?
C10A C11A H11A 120.4 . . ?
C12 C11A C10A 119.3(7) . . ?
C12 C11A H11A 120.4 . . ?
C14A C13A H13A 119.6 . . ?
C14A C13A C12 120.8(7) . . ?
C12 C13A H13A 119.6 . . ?
C13A C14A H14A 119.0 . . ?
C9 C14A C13A 122.1(8) . . ?
C9 C14A H14A 119.0 . . ?
N2 C15A H15A 109.5 . . ?
N2 C15A H15B 109.5 . . ?
N2 C15A H15C 109.5 . . ?
H15A C15A H15B 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
N2 C16A H16A 109.5 . . ?
N2 C16A H16B 109.5 . . ?
N2 C16A H16C 109.5 . . ?
H16A C16A H16B 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C2B C3B H3B 118.2 . . ?
C4 C3B H3B 118.2 . . ?
C4 C3B C2B 123.5(12) . . ?
C3B C2B H2B 121.9 . . ?
C1 C2B C3B 116.2(12) . . ?
C1 C2B H2B 121.9 . . ?
C2A C1 N1 118.5(5) . . ?
C2A C1 C6A 122.3(6) . . ?
C6A C1 N1 119.2(5) . . ?
C2B C1 N1 117.3(6) . . ?
C2B C1 C6B 123.3(7) . . ?
C6B C1 N1 119.4(5) . . ?
C1 C6B H6B 122.6 . . ?
C1 C6B C5B 114.8(10) . . ?
C5B C6B H6B 122.6 . . ?
C6B C5B H5B 117.8 . . ?
C4 C5B C6B 124.4(12) . . ?
C4 C5B H5B 117.8 . . ?
C3A C4 C7A 117.2(6) . . ?
C5A C4 C3A 117.2(6) . . ?
C5A C4 C7A 125.6(6) . . ?
C3B C4 C7B 135.1(19) . . ?
C5B C4 C3B 117.6(8) . . ?
C5B C4 C7B 99.7(13) . . ?
C4 C7B H7B 119.5 . . ?
C8B C7B C4 121(2) . . ?
C8B C7B H7B 119.5 . . ?
C7B C8B H8B 115.5 . . ?
C7B C8B C9 129(2) . . ?
C9 C8B H8B 115.5 . . ?
C10B C11B H11B 118.3 . . ?
C10B C11B C12 123.3(11) . . ?
C12 C11B H11B 118.3 . . ?
C11B C10B H10B 120.7 . . ?
C11B C10B C9 118.6(10) . . ?
C9 C10B H10B 120.7 . . ?
C10A C9 C8A 125.3(6) . . ?
C10A C9 C14A 117.6(6) . . ?
C14A C9 C8A 117.2(6) . . ?
C10B C9 C8B 101.4(13) . . ?
C10B C9 C14B 116.3(7) . . ?
C14B C9 C8B 138.7(18) . . ?
C9 C14B H14B 119.6 . . ?
C13B C14B C9 120.7(11) . . ?
C13B C14B H14B 119.6 . . ?
C14B C13B H13B 118.7 . . ?
C14B C13B C12 122.7(12) . . ?
C12 C13B H13B 118.7 . . ?
N2 C12 C11A 122.3(5) . . ?
N2 C12 C13A 121.4(5) . . ?
N2 C12 C11B 121.6(6) . . ?
N2 C12 C13B 120.1(6) . . ?
C11A C12 C13A 116.3(6) . . ?
C13B C12 C11B 118.3(8) . . ?
N2 C15B H15D 109.5 . . ?
N2 C15B H15E 109.5 . . ?
N2 C15B H15F 109.5 . . ?
H15D C15B H15E 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
N2 C16B H16D 109.5 . . ?
N2 C16B H16E 109.5 . . ?
N2 C16B H16F 109.5 . . ?
H16D C16B H16E 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 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
N1 C1 C6B C5B -178.9(9) . . . . ?
O1A N1 C1 C2A -176.3(9) . . . . ?
O1A N1 C1 C6A 1.1(10) . . . . ?
O2A N1 C1 C2A 3.2(11) . . . . ?
O2A N1 C1 C6A -179.3(10) . . . . ?
C2A C3A C4 C5A 1.2(11) . . . . ?
C2A C3A C4 C7A -179.8(8) . . . . ?
C3A C2A C1 N1 179.5(7) . . . . ?
C3A C2A C1 C6A 2.1(12) . . . . ?
C5A C6A C1 N1 179.6(6) . . . . ?
C5A C6A C1 C2A -3.0(11) . . . . ?
C6A C5A C4 C3A -2.2(11) . . . . ?
C6A C5A C4 C7A 179.0(8) . . . . ?
C7A C8A C9 C10A -20.0(13) . . . . ?
C7A C8A C9 C14A 161.9(8) . . . . ?
C8A C7A C4 C3A -161.0(8) . . . . ?
C8A C7A C4 C5A 17.8(14) . . . . ?
C10A C11A C12 N2 179.3(6) . . . . ?
C10A C11A C12 C13A -0.7(10) . . . . ?
C11A C10A C9 C8A -179.5(8) . . . . ?
C11A C10A C9 C14A -1.5(11) . . . . ?
C13A C14A C9 C8A -179.6(8) . . . . ?
C13A C14A C9 C10A 2.2(11) . . . . ?
C14A C13A C12 N2 -178.5(7) . . . . ?
C14A C13A C12 C11A 1.5(11) . . . . ?
C15A N2 C12 C11A 166.8(8) . . . . ?
C15A N2 C12 C13A -13.2(10) . . . . ?
C16A N2 C12 C11A 8.0(14) . . . . ?
C16A N2 C12 C13A -172.0(12) . . . . ?
O1B N1 C1 C2B 172.1(10) . . . . ?
O1B N1 C1 C6B -7.7(11) . . . . ?
O2B N1 C1 C2B 3.0(13) . . . . ?
O2B N1 C1 C6B -176.8(11) . . . . ?
C3B C2B C1 N1 178.6(9) . . . . ?
C3B C2B C1 C6B -1.7(16) . . . . ?
C3B C4 C7B C8B -80(4) . . . . ?
C2B C3B C4 C5B -4.9(17) . . . . ?
C2B C3B C4 C7B -148(2) . . . . ?
C2B C1 C6B C5B 1.4(15) . . . . ?
C1 C2A C3A C4 -1.2(12) . . . . ?
C1 C6B C5B C4 -2.9(17) . . . . ?
C6B C5B C4 C3B 4.6(17) . . . . ?
C6B C5B C4 C7B 159(2) . . . . ?
C5B C4 C7B C8B 133(3) . . . . ?
C4 C5A C6A C1 3.1(11) . . . . ?
C4 C7A C8A C9 -177.5(11) . . . . ?
C4 C3B C2B C1 3.5(18) . . . . ?
C4 C7B C8B C9 -178(4) . . . . ?
C7B C8B C9 C10B -135(4) . . . . ?
C7B C8B C9 C14B 69(6) . . . . ?
C8B C9 C14B C13B 155(3) . . . . ?
C11B C10B C9 C8B -165(2) . . . . ?
C11B C10B C9 C14B -2.4(17) . . . . ?
C10B C11B C12 N2 -179.5(11) . . . . ?
C10B C11B C12 C13B 2.3(18) . . . . ?
C10B C9 C14B C13B 1.8(17) . . . . ?
C9 C10A C11A C12 0.8(12) . . . . ?
C9 C14B C13B C12 1(2) . . . . ?
C14B C13B C12 N2 178.9(12) . . . . ?
C14B C13B C12 C11B -2.9(19) . . . . ?
C12 C13A C14A C9 -2.3(12) . . . . ?
C12 C11B C10B C9 0(2) . . . . ?
C15B N2 C12 C11B -162.6(12) . . . . ?
C15B N2 C12 C13B 15.6(13) . . . . ?
C16B N2 C12 C11B -15.0(15) . . . . ?
C16B N2 C12 C13B 163.2(14) . . . . ?


_ins_header                      
;
TITL ek1918_a_P21 in P2(1) 
REM P2(1) (#4 in standard setting)
CELL 1.54184   5.937789   7.372117  15.356879  90.0000  96.4174  90.0000
ZERR    3.00   0.000429   0.000681   0.001194   0.0000   0.0066   0.0000
LATT -1
SYMM -x, y+1/2,-z 
SFAC C H N O
UNIT 33.00 30.00 3.00 3.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.308
_oxdiff_exptl_absorpt_empirical_full_min 0.758
####################################################################### 
# 
# 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_compound_3a_ortho
_database_code_depnum_ccdc_archive 'CCDC 2058515'
loop_
_audit_author_name
_audit_author_address
'Jari Konu'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_audit_creation_date             2019-06-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 Br N O2 S'
_chemical_formula_sum            'C12 H8 Br N O2 S'
_chemical_formula_weight         310.16
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.5793(15)
_cell_length_b                   11.453(2)
_cell_length_c                   27.652(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2400.4(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8985
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.020
_cell_measurement_theta_min      2.947
_shelx_estimated_absorpt_T_max   0.870
_shelx_estimated_absorpt_T_min   0.534
_exptl_absorpt_coefficient_mu    3.586
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.561
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (SHELXTL-NT v5.1, Bruker)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0944
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8985
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         2.947
_diffrn_ambient_temperature      170
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1734
_reflns_number_total             2112
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         1.121
_refine_diff_density_min         -0.874
_refine_diff_density_rms         0.143
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.266
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0945
_refine_ls_restrained_S_all      1.266
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0138P)²+35.4419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1668
_refine_ls_wR_factor_ref         0.1737
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.42056(13) 0.14037(9) 0.64594(4) 0.0324(3) Uani 1 1 d . . . . .
S1 S 0.2048(3) 0.4270(2) 0.55867(9) 0.0295(6) Uani 1 1 d . . . . .
O1 O 0.3192(13) 0.6953(9) 0.2397(3) 0.071(3) Uani 1 1 d . . . . .
O2 O 0.4676(12) 0.5391(8) 0.2237(3) 0.057(2) Uani 1 1 d . . . . .
N1 N 0.3881(12) 0.6035(8) 0.2517(3) 0.037(2) Uani 1 1 d . . . . .
C1 C 0.3744(12) 0.5668(9) 0.3027(3) 0.027(2) Uani 1 1 d . . . . .
C2 C 0.4545(13) 0.4644(10) 0.3176(3) 0.033(3) Uani 1 1 d . . . . .
H2 H 0.520302 0.418878 0.295215 0.040 Uiso 1 1 calc R . . . .
C3 C 0.4382(13) 0.4287(9) 0.3653(4) 0.033(2) Uani 1 1 d . . . . .
H3 H 0.493379 0.358582 0.375659 0.039 Uiso 1 1 calc R . . . .
C4 C 0.3386(12) 0.4970(9) 0.3989(4) 0.028(2) Uani 1 1 d . . . . .
C5 C 0.2627(13) 0.6009(8) 0.3823(3) 0.027(2) Uani 1 1 d . . . . .
H5 H 0.199465 0.648582 0.404429 0.032 Uiso 1 1 calc R . . . .
C6 C 0.2770(13) 0.6363(10) 0.3345(4) 0.032(2) Uani 1 1 d . . . . .
H6 H 0.221966 0.706097 0.323640 0.038 Uiso 1 1 calc R . . . .
C7 C 0.3141(11) 0.4627(9) 0.4497(3) 0.027(2) Uani 1 1 d . . . . .
H7 H 0.241498 0.512911 0.468430 0.032 Uiso 1 1 calc R . . . .
C8 C 0.3802(11) 0.3701(9) 0.4731(3) 0.026(2) Uani 1 1 d . . . . .
H8 H 0.455815 0.319569 0.455395 0.031 Uiso 1 1 calc R . . . .
C9 C 0.3453(12) 0.3405(8) 0.5236(3) 0.024(2) Uani 1 1 d . . . . .
C10 C 0.4080(12) 0.2493(9) 0.5502(3) 0.027(2) Uani 1 1 d . . . . .
H10 H 0.482822 0.190378 0.537348 0.032 Uiso 1 1 calc R . . . .
C11 C 0.3502(12) 0.2513(8) 0.5988(3) 0.025(2) Uani 1 1 d . . . . .
C12 C 0.2386(14) 0.3404(9) 0.6084(3) 0.031(2) Uani 1 1 d . . . . .
H12 H 0.185332 0.353538 0.638990 0.037 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C11 1.897(10) . ?
S1 C9 1.749(10) . ?
S1 C12 1.714(10) . ?
O1 N1 1.220(12) . ?
O2 N1 1.227(12) . ?
N1 C1 1.476(12) . ?
C1 C2 1.383(14) . ?
C1 C6 1.397(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(13) . ?
C3 H3 0.9500 . ?
C3 C4 1.431(14) . ?
C4 C5 1.399(14) . ?
C4 C7 1.469(13) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(13) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.339(14) . ?
C8 H8 0.9500 . ?
C8 C9 1.462(13) . ?
C9 C10 1.363(13) . ?
C10 H10 0.9500 . ?
C10 C11 1.414(13) . ?
C11 C12 1.352(14) . ?
C12 H12 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
C12 S1 C9 91.5(5) . . ?
O1 N1 O2 123.9(10) . . ?
O1 N1 C1 118.3(9) . . ?
O2 N1 C1 117.8(9) . . ?
C2 C1 N1 119.6(9) . . ?
C2 C1 C6 122.0(9) . . ?
C6 C1 N1 118.4(9) . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.5(9) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.3(10) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C7 122.8(9) . . ?
C5 C4 C3 117.9(9) . . ?
C5 C4 C7 119.3(9) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 122.0(9) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 H6 120.9 . . ?
C5 C6 C1 118.3(10) . . ?
C5 C6 H6 120.9 . . ?
C4 C7 H7 115.6 . . ?
C8 C7 C4 128.7(9) . . ?
C8 C7 H7 115.6 . . ?
C7 C8 H8 117.4 . . ?
C7 C8 C9 125.3(9) . . ?
C9 C8 H8 117.4 . . ?
C8 C9 S1 120.6(7) . . ?
C10 C9 S1 110.3(7) . . ?
C10 C9 C8 129.1(9) . . ?
C9 C10 H10 123.5 . . ?
C9 C10 C11 113.1(9) . . ?
C11 C10 H10 123.5 . . ?
C10 C11 Br1 123.7(7) . . ?
C12 C11 Br1 123.1(7) . . ?
C12 C11 C10 113.1(9) . . ?
S1 C12 H12 124.0 . . ?
C11 C12 S1 111.9(8) . . ?
C11 C12 H12 124.0 . . ?

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
Br1 C11 C12 S1 178.7(5) . . . . ?
S1 C9 C10 C11 -2.5(10) . . . . ?
O1 N1 C1 C2 -178.6(10) . . . . ?
O1 N1 C1 C6 2.6(14) . . . . ?
O2 N1 C1 C2 1.8(14) . . . . ?
O2 N1 C1 C6 -176.9(9) . . . . ?
N1 C1 C2 C3 -178.5(9) . . . . ?
N1 C1 C6 C5 179.3(9) . . . . ?
C1 C2 C3 C4 0.2(15) . . . . ?
C2 C1 C6 C5 0.5(15) . . . . ?
C2 C3 C4 C5 -1.3(14) . . . . ?
C2 C3 C4 C7 178.9(9) . . . . ?
C3 C4 C5 C6 2.1(14) . . . . ?
C3 C4 C7 C8 2.5(16) . . . . ?
C4 C5 C6 C1 -1.7(15) . . . . ?
C4 C7 C8 C9 -178.3(9) . . . . ?
C5 C4 C7 C8 -177.3(10) . . . . ?
C6 C1 C2 C3 0.2(15) . . . . ?
C7 C4 C5 C6 -178.1(9) . . . . ?
C7 C8 C9 S1 1.1(13) . . . . ?
C7 C8 C9 C10 -179.3(10) . . . . ?
C8 C9 C10 C11 177.8(9) . . . . ?
C9 S1 C12 C11 0.0(8) . . . . ?
C9 C10 C11 Br1 -177.5(7) . . . . ?
C9 C10 C11 C12 2.7(12) . . . . ?
C10 C11 C12 S1 -1.5(11) . . . . ?
C12 S1 C9 C8 -178.9(8) . . . . ?
C12 S1 C9 C10 1.4(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound_1a_noncentro
_database_code_depnum_ccdc_archive 'CCDC 2058508'
loop_
_audit_author_name
_audit_author_address
'Jari Konu'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 Cl N O4'
_chemical_formula_sum            'C16 H14 Cl N O4'
_chemical_formula_weight         319.73
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H14 Cl N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.2178(2)
_cell_length_b                   16.5839(6)
_cell_length_c                   10.2700(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.821(4)
_cell_angle_gamma                90
_cell_volume                     716.76(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1711
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.4350
_cell_measurement_theta_min      4.2640
_shelx_estimated_absorpt_T_max   0.845
_shelx_estimated_absorpt_T_min   0.439
_exptl_absorpt_coefficient_mu    2.533
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.863
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -5 -3 0.0203
1 5 2 0.1199
-1 -5 -2 0.0979
0 5 -3 0.0411
0 -5 3 0.0291
-1 5 -3 0.0725
-1 7 5 0.0616
1 -6 -5 0.0651
0 7 5 0.0448

_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.069
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 -5.0000 -3.0000 -0.6031 -0.1588 0.1750
1.0000 5.0000 2.0000 0.4125 0.1522 -0.5112
-1.0000 -5.0000 -2.0000 -0.4125 -0.1522 0.5112
0.0000 5.0000 -3.0000 -0.1681 0.6190 -0.0862
-0.0000 -5.0000 3.0000 0.1681 -0.6190 0.0862
-1.0000 5.0000 -3.0000 -0.1061 0.7023 0.2647
-1.0000 7.0000 5.0000 1.0092 0.2442 0.0940
1.0000 -6.0000 -5.0000 -0.9657 -0.1665 -0.1202
0.0000 7.0000 5.0000 0.9472 0.1610 -0.2569

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2847
_diffrn_reflns_point_group_measured_fraction_full 0.719
_diffrn_reflns_point_group_measured_fraction_max 0.683
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.873
_diffrn_reflns_theta_min         4.315
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00 -25.00   1.00    1.00    --  -41.65 -37.00 150.00   82
  2  ω    -60.00  24.00   1.00    1.00    --  -41.65  37.00 -30.00   84
  3  ω     45.00  83.00   1.00    1.00    --   41.65-125.00 120.00   38
  4  ω    101.00 174.00   1.00    2.00    --  112.00 111.00  90.00   73
  5  ω     42.00  91.00   1.00    2.00    --  112.00 -94.00  30.00   49
  6  ω     37.00 128.00   1.00    2.00    --  112.00 -30.00-180.00   91
  7  ω     77.00 104.00   1.00    2.00    --  112.00 -94.00  60.00   27
  8  ω     32.00  71.00   1.00    2.00    --  112.00 -94.00  60.00   39
  9  ω     63.00 141.00   1.00    2.00    --  112.00 -61.00  30.00   78
 10  ω     40.00 133.00   1.00    2.00    --  112.00 -61.00 150.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0620266000
_diffrn_orient_matrix_UB_12      0.0435017000
_diffrn_orient_matrix_UB_13      0.1285330000
_diffrn_orient_matrix_UB_21      -0.0832803000
_diffrn_orient_matrix_UB_22      0.0777831000
_diffrn_orient_matrix_UB_23      -0.0767051000
_diffrn_orient_matrix_UB_31      -0.3509222000
_diffrn_orient_matrix_UB_32      -0.0261243000
_diffrn_orient_matrix_UB_33      -0.0148044000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.354
_reflns_Friedel_fraction_full    0.420
_reflns_Friedel_fraction_max     0.370
_reflns_number_gt                1977
_reflns_number_total             2072
_reflns_odcompleteness_completeness 99.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2072
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0685P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1061
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.53283(18) 0.54006(5) 0.60294(7) 0.0259(2) Uani 1 1 d . . . . .
O1 O 1.3492(9) 0.79105(19) -0.0727(3) 0.0427(8) Uani 1 1 d . . . . .
O2 O 1.4437(8) 0.69700(19) -0.2108(3) 0.0348(6) Uani 1 1 d . . . . .
O3 O -0.0681(6) 0.27975(16) 0.6097(2) 0.0264(6) Uani 1 1 d . . . . .
O4 O 0.1727(6) 0.41458(16) 0.7229(2) 0.0238(5) Uani 1 1 d . . . . .
N1 N 1.3254(8) 0.7208(2) -0.1124(3) 0.0270(6) Uani 1 1 d . . . . .
C1 C 1.1451(8) 0.6637(2) -0.0361(3) 0.0221(6) Uani 1 1 d . . . . .
C2 C 1.0911(8) 0.5862(2) -0.0842(3) 0.0241(7) Uani 1 1 d . . . . .
H2 H 1.163939 0.570372 -0.163735 0.029 Uiso 1 1 calc R . . . .
C3 C 0.9259(7) 0.5339(2) -0.0099(3) 0.0249(6) Uani 1 1 d . . . . .
H3 H 0.885839 0.481901 -0.040749 0.030 Uiso 1 1 calc R . . . .
C4 C 0.8163(7) 0.55617(19) 0.1105(3) 0.0208(7) Uani 1 1 d . . . . .
C5 C 0.8729(8) 0.6354(2) 0.1542(3) 0.0242(7) Uani 1 1 d . . . . .
H5 H 0.797941 0.651837 0.233112 0.029 Uiso 1 1 calc R . . . .
C6 C 1.0393(8) 0.6896(2) 0.0814(3) 0.0247(7) Uani 1 1 d . . . . .
H6 H 1.078411 0.741883 0.110858 0.030 Uiso 1 1 calc R . . . .
C7 C 0.6473(8) 0.4968(2) 0.1859(3) 0.0231(7) Uani 1 1 d . . . . .
H7 H 0.586372 0.448947 0.144118 0.028 Uiso 1 1 calc R . . . .
C8 C 0.5737(8) 0.5058(2) 0.3093(3) 0.0231(6) Uani 1 1 d . . . . .
H8 H 0.636618 0.553488 0.350939 0.028 Uiso 1 1 calc R . . . .
C9 C 0.4026(8) 0.4471(2) 0.3852(3) 0.0212(6) Uani 1 1 d . . . . .
C10 C 0.2661(8) 0.3781(2) 0.3278(3) 0.0225(6) Uani 1 1 d . . . . .
H10 H 0.282836 0.369732 0.239032 0.027 Uiso 1 1 calc R . . . .
C11 C 0.1058(8) 0.3213(2) 0.3984(3) 0.0233(7) Uani 1 1 d . . . . .
H11 H 0.016746 0.276117 0.356773 0.028 Uiso 1 1 calc R . . . .
C12 C 0.0793(8) 0.3324(2) 0.5311(3) 0.0222(6) Uani 1 1 d . . . . .
C13 C 0.2107(8) 0.4015(2) 0.5936(3) 0.0214(6) Uani 1 1 d . . . . .
C14 C 0.3721(8) 0.4574(2) 0.5197(3) 0.0215(7) Uani 1 1 d . . . . .
C15 C -0.2071(8) 0.2098(2) 0.5482(4) 0.0267(7) Uani 1 1 d . . . . .
H15A H -0.361752 0.225945 0.480389 0.040 Uiso 1 1 calc GR . . . .
H15B H -0.308403 0.178041 0.611614 0.040 Uiso 1 1 calc GR . . . .
H15C H -0.044404 0.178368 0.511148 0.040 Uiso 1 1 calc GR . . . .
C16 C 0.3991(9) 0.3717(3) 0.8072(3) 0.0265(7) Uani 1 1 d . . . . .
H16A H 0.384647 0.315036 0.788407 0.040 Uiso 1 1 calc GR . . . .
H16B H 0.354870 0.380883 0.896432 0.040 Uiso 1 1 calc GR . . . .
H16C H 0.609485 0.390400 0.793043 0.040 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C14 1.730(3) . ?
O1 N1 1.236(5) . ?
O2 N1 1.223(4) . ?
O3 C12 1.367(4) . ?
O3 C15 1.428(4) . ?
O4 C13 1.365(4) . ?
O4 C16 1.434(4) . ?
N1 C1 1.473(4) . ?
C1 C2 1.389(5) . ?
C1 C6 1.383(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.398(5) . ?
C4 C5 1.404(5) . ?
C4 C7 1.466(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.333(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.466(5) . ?
C9 C10 1.394(5) . ?
C9 C14 1.406(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.391(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(5) . ?
C12 C13 1.409(5) . ?
C13 C14 1.403(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O3 C15 116.6(3) . . ?
C13 O4 C16 113.0(3) . . ?
O1 N1 C1 117.7(3) . . ?
O2 N1 O1 123.3(3) . . ?
O2 N1 C1 119.0(3) . . ?
C2 C1 N1 119.0(3) . . ?
C6 C1 N1 118.2(3) . . ?
C6 C1 C2 122.8(3) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.6(3) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.2(3) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 118.1(3) . . ?
C3 C4 C7 119.3(3) . . ?
C5 C4 C7 122.5(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.2(3) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C4 C7 H7 117.3 . . ?
C8 C7 C4 125.4(3) . . ?
C8 C7 H7 117.3 . . ?
C7 C8 H8 117.1 . . ?
C7 C8 C9 125.9(3) . . ?
C9 C8 H8 117.1 . . ?
C10 C9 C8 121.6(3) . . ?
C10 C9 C14 116.9(3) . . ?
C14 C9 C8 121.5(3) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 C9 122.5(3) . . ?
C11 C10 H10 118.8 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
O3 C12 C11 124.4(3) . . ?
O3 C12 C13 115.5(3) . . ?
C11 C12 C13 120.0(3) . . ?
O4 C13 C12 120.3(3) . . ?
O4 C13 C14 121.0(3) . . ?
C14 C13 C12 118.7(3) . . ?
C9 C14 Cl1 121.5(3) . . ?
C13 C14 Cl1 116.4(2) . . ?
C13 C14 C9 122.1(3) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 N1 C1 C2 174.5(3) . . . . ?
O1 N1 C1 C6 -6.0(5) . . . . ?
O2 N1 C1 C2 -5.5(5) . . . . ?
O2 N1 C1 C6 173.9(3) . . . . ?
O3 C12 C13 O4 -3.3(4) . . . . ?
O3 C12 C13 C14 178.6(3) . . . . ?
O4 C13 C14 Cl1 2.9(4) . . . . ?
O4 C13 C14 C9 -177.2(3) . . . . ?
N1 C1 C2 C3 179.1(3) . . . . ?
N1 C1 C6 C5 -179.1(3) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C2 C1 C6 C5 0.2(5) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
C2 C3 C4 C7 -178.8(3) . . . . ?
C3 C4 C5 C6 -1.4(5) . . . . ?
C3 C4 C7 C8 169.1(3) . . . . ?
C4 C5 C6 C1 0.6(5) . . . . ?
C4 C7 C8 C9 179.5(3) . . . . ?
C5 C4 C7 C8 -11.0(5) . . . . ?
C6 C1 C2 C3 -0.3(5) . . . . ?
C7 C4 C5 C6 178.8(3) . . . . ?
C7 C8 C9 C10 -7.5(5) . . . . ?
C7 C8 C9 C14 171.6(3) . . . . ?
C8 C9 C10 C11 179.3(3) . . . . ?
C8 C9 C14 Cl1 0.4(4) . . . . ?
C8 C9 C14 C13 -179.6(3) . . . . ?
C9 C10 C11 C12 -0.3(5) . . . . ?
C10 C9 C14 Cl1 179.6(2) . . . . ?
C10 C9 C14 C13 -0.4(5) . . . . ?
C10 C11 C12 O3 -178.8(3) . . . . ?
C10 C11 C12 C13 0.9(5) . . . . ?
C11 C12 C13 O4 177.0(3) . . . . ?
C11 C12 C13 C14 -1.1(4) . . . . ?
C12 C13 C14 Cl1 -179.0(2) . . . . ?
C12 C13 C14 C9 0.9(5) . . . . ?
C14 C9 C10 C11 0.1(5) . . . . ?
C15 O3 C12 C11 -1.1(5) . . . . ?
C15 O3 C12 C13 179.2(3) . . . . ?
C16 O4 C13 C12 82.8(4) . . . . ?
C16 O4 C13 C14 -99.1(4) . . . . ?


_ins_header                      
;
TITL ek1833_a2 in P2(1) 
REM P2(1) (#4 in standard setting)
CELL 1.54184   4.217774  16.583920  10.269984  90.0000  93.8207  90.0000
ZERR    2.00   0.000160   0.000558   0.000413   0.0000   0.0037   0.0000
LATT -1
SYMM -x, y+1/2,-z 
SFAC C H N O Cl
UNIT 32.00 28.00 2.00 2.00 2.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.520
_oxdiff_exptl_absorpt_empirical_full_min 0.753
####################################################################### 
# 
# 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_compound_1d
_database_code_depnum_ccdc_archive 'CCDC 2058510'
loop_
_audit_author_name
_audit_author_address
'Jari Konu'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 N O4'
_chemical_formula_sum            'C16 H15 N O4'
_chemical_formula_weight         285.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H15 O4 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.2417(15)
_cell_length_b                   7.6505(7)
_cell_length_c                   14.5189(14)
_cell_angle_alpha                90
_cell_angle_beta                 111.612(12)
_cell_angle_gamma                90
_cell_volume                     1367.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1234
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      28.2010
_cell_measurement_theta_min      2.8520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.994
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 2 -1 0.0833
-5 -2 1 0.0643
1 0 -5 0.1042
-1 0 5 0.1362
5 -5 -2 0.0521
-5 5 2 0.0521

_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.104
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
5.0000 2.0000 -1.0000 -0.0261 0.2174 0.2470
-5.0000 -2.0000 1.0000 0.0261 -0.2174 -0.2470
0.9997 -0.0001 -5.0000 -0.0626 0.1788 -0.1593
-0.9997 0.0001 5.0000 0.0626 -0.1788 0.1593
4.9990 -5.0002 -2.0000 0.5006 0.1387 -0.1288
-4.9990 5.0002 2.0000 -0.5006 -0.1387 0.1288

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0945
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5843
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.212
_diffrn_reflns_theta_min         2.858
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3953
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  80.00   1.00   40.00    --   10.43  19.00  60.00   97
  2  ω    -58.00   9.00   1.00   40.00    --   10.43 -19.00  60.00   67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0296156000
_diffrn_orient_matrix_UB_12      -0.0778778000
_diffrn_orient_matrix_UB_13      0.0184370000
_diffrn_orient_matrix_UB_21      0.0314044000
_diffrn_orient_matrix_UB_22      0.0154500000
_diffrn_orient_matrix_UB_23      -0.0294875000
_diffrn_orient_matrix_UB_31      0.0380791000
_diffrn_orient_matrix_UB_32      0.0480335000
_diffrn_orient_matrix_UB_33      0.0394750000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1633
_reflns_number_total             3149
_reflns_odcompleteness_completeness 99.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1437
_refine_ls_R_factor_gt           0.0802
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1114P)²+0.3225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1908
_refine_ls_wR_factor_ref         0.2551
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C14(H14)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3131(2) 0.3976(4) -0.00840(17) 0.0545(7) Uani 1 1 d . . . . .
O2 O 0.4516(2) 0.2912(4) -0.03354(16) 0.0537(7) Uani 1 1 d . . . . .
O3 O 0.95502(18) 0.3757(3) 0.90110(15) 0.0419(6) Uani 1 1 d . . . . .
O4 O 0.82957(18) 0.6257(3) 0.80864(16) 0.0430(6) Uani 1 1 d . . . . .
N1 N 0.4087(2) 0.3543(4) 0.0213(2) 0.0438(7) Uani 1 1 d . . . . .
C1 C 0.4751(3) 0.3720(4) 0.1264(2) 0.0378(8) Uani 1 1 d . . . . .
C2 C 0.5850(3) 0.3372(4) 0.1598(2) 0.0407(8) Uani 1 1 d . . . . .
H2 H 0.617709 0.307120 0.115309 0.049 Uiso 1 1 calc R . . . .
C3 C 0.6456(3) 0.3475(4) 0.2591(2) 0.0390(8) Uani 1 1 d . . . . .
H3 H 0.719286 0.321067 0.281987 0.047 Uiso 1 1 calc R . . . .
C4 C 0.5977(3) 0.3973(4) 0.3270(2) 0.0377(8) Uani 1 1 d . . . . .
C5 C 0.4871(3) 0.4355(4) 0.2901(2) 0.0391(8) Uani 1 1 d . . . . .
H5 H 0.454121 0.469476 0.333824 0.047 Uiso 1 1 calc R . . . .
C6 C 0.4255(3) 0.4241(4) 0.1904(2) 0.0405(8) Uani 1 1 d . . . . .
H6 H 0.351821 0.451123 0.166648 0.049 Uiso 1 1 calc R . . . .
C7 C 0.6591(3) 0.4095(5) 0.4335(2) 0.0420(8) Uani 1 1 d . . . . .
H7 H 0.627568 0.476332 0.469290 0.050 Uiso 1 1 calc R . . . .
C8 C 0.7543(3) 0.3369(4) 0.4857(2) 0.0419(8) Uani 1 1 d . . . . .
H8 H 0.788216 0.272905 0.450887 0.050 Uiso 1 1 calc R . . . .
C9 C 0.8102(3) 0.3489(4) 0.5929(2) 0.0392(8) Uani 1 1 d . . . . .
C10 C 0.8830(3) 0.2201(5) 0.6439(2) 0.0417(8) Uani 1 1 d . . . . .
H10 H 0.899283 0.130105 0.608630 0.050 Uiso 1 1 calc R . . . .
C11 C 0.9324(3) 0.2226(5) 0.7471(2) 0.0405(8) Uani 1 1 d . . . . .
H11 H 0.979545 0.133247 0.779990 0.049 Uiso 1 1 calc R . . . .
C12 C 0.9111(2) 0.3580(4) 0.8001(2) 0.0370(8) Uani 1 1 d . . . . .
C13 C 0.8415(2) 0.4935(4) 0.7499(2) 0.0374(8) Uani 1 1 d . . . . .
C14 C 0.7909(2) 0.4883(4) 0.6479(2) 0.0379(8) Uani 1 1 d . . . . .
H14 H 0.743560 0.577534 0.615301 0.045 Uiso 1 1 calc R . . . .
C15 C 1.0337(3) 0.2502(5) 0.9560(2) 0.0508(10) Uani 1 1 d . . . . .
H15A H 1.094672 0.253311 0.935267 0.076 Uiso 1 1 calc GR . . . .
H15B H 1.001906 0.135638 0.944437 0.076 Uiso 1 1 calc GR . . . .
H15C H 1.057665 0.277039 1.025390 0.076 Uiso 1 1 calc GR . . . .
C16 C 0.7838(3) 0.7866(4) 0.7618(2) 0.0456(9) Uani 1 1 d . . . . .
H16A H 0.708585 0.769129 0.721582 0.068 Uiso 1 1 calc GR . . . .
H16B H 0.822141 0.825637 0.720984 0.068 Uiso 1 1 calc GR . . . .
H16C H 0.789746 0.873039 0.811493 0.068 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.223(4) . ?
O2 N1 1.234(3) . ?
O3 C12 1.371(4) . ?
O3 C15 1.426(4) . ?
O4 C13 1.369(4) . ?
O4 C16 1.429(4) . ?
N1 C1 1.460(4) . ?
C1 C2 1.380(5) . ?
C1 C6 1.379(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.406(4) . ?
C4 C5 1.393(4) . ?
C4 C7 1.461(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.330(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.459(4) . ?
C9 C10 1.387(5) . ?
C9 C14 1.411(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.397(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(5) . ?
C12 C13 1.400(5) . ?
C13 C14 1.382(4) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O3 C15 117.8(3) . . ?
C13 O4 C16 117.8(2) . . ?
O1 N1 O2 122.7(3) . . ?
O1 N1 C1 119.4(3) . . ?
O2 N1 C1 117.9(3) . . ?
C2 C1 N1 120.1(3) . . ?
C6 C1 N1 118.5(3) . . ?
C6 C1 C2 121.4(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C7 122.7(3) . . ?
C5 C4 C3 118.0(3) . . ?
C5 C4 C7 119.3(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 H6 120.6 . . ?
C4 C7 H7 115.9 . . ?
C8 C7 C4 128.1(3) . . ?
C8 C7 H7 115.9 . . ?
C7 C8 H8 117.2 . . ?
C7 C8 C9 125.7(3) . . ?
C9 C8 H8 117.2 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 C14 118.0(3) . . ?
C14 C9 C8 121.7(3) . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.5(3) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
O3 C12 C11 125.2(3) . . ?
O3 C12 C13 115.0(3) . . ?
C11 C12 C13 119.7(3) . . ?
O4 C13 C12 115.3(3) . . ?
O4 C13 C14 124.5(3) . . ?
C14 C13 C12 120.2(3) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.7(3) . . ?
C13 C14 H14 119.6 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C15 H15C O4 0.96 2.44 3.361(4) 161.4 3_767 yes

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 N1 C1 C2 -174.8(3) . . . . ?
O1 N1 C1 C6 5.1(5) . . . . ?
O2 N1 C1 C2 7.2(5) . . . . ?
O2 N1 C1 C6 -173.0(3) . . . . ?
O3 C12 C13 O4 1.5(4) . . . . ?
O3 C12 C13 C14 -178.8(3) . . . . ?
O4 C13 C14 C9 178.2(3) . . . . ?
N1 C1 C2 C3 -177.4(3) . . . . ?
N1 C1 C6 C5 177.9(3) . . . . ?
C1 C2 C3 C4 -1.7(5) . . . . ?
C2 C1 C6 C5 -2.3(5) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C2 C3 C4 C7 179.8(3) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C3 C4 C7 C8 -19.2(6) . . . . ?
C4 C5 C6 C1 0.6(5) . . . . ?
C4 C7 C8 C9 -177.8(3) . . . . ?
C5 C4 C7 C8 160.5(3) . . . . ?
C6 C1 C2 C3 2.8(5) . . . . ?
C7 C4 C5 C6 -179.3(3) . . . . ?
C7 C8 C9 C10 154.6(4) . . . . ?
C7 C8 C9 C14 -24.2(5) . . . . ?
C8 C9 C10 C11 -175.9(3) . . . . ?
C8 C9 C14 C13 177.4(3) . . . . ?
C9 C10 C11 C12 -1.7(5) . . . . ?
C10 C9 C14 C13 -1.4(5) . . . . ?
C10 C11 C12 O3 -179.5(3) . . . . ?
C10 C11 C12 C13 -1.1(5) . . . . ?
C11 C12 C13 O4 -177.0(3) . . . . ?
C11 C12 C13 C14 2.6(5) . . . . ?
C12 C13 C14 C9 -1.4(5) . . . . ?
C14 C9 C10 C11 2.9(5) . . . . ?
C15 O3 C12 C11 3.7(5) . . . . ?
C15 O3 C12 C13 -174.7(3) . . . . ?
C16 O4 C13 C12 164.1(3) . . . . ?
C16 O4 C13 C14 -15.6(4) . . . . ?


_ins_header                      
;
TITL ek1908_a in P2(1)/c 
REM P2(1)/c (#14 in standard setting)
CELL 0.71073  13.241691   7.650500  14.518933  90.0000 111.6124  90.0000
ZERR    3.00   0.001484   0.000685   0.001416   0.0000   0.0120   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2 
SFAC C H N O
UNIT 54.00 45.00 3.00 12.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.653
_oxdiff_exptl_absorpt_empirical_full_min 0.665
####################################################################### 
# 
# 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_compound_3c
_database_code_depnum_ccdc_archive 'CCDC 2058517'
loop_
_audit_author_name
_audit_author_address
'Jari Konu'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N O2 S2'
_chemical_formula_sum            'C13 H11 N O2 S2'
_chemical_formula_weight         277.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.9031(16)
_cell_length_b                   7.3210(15)
_cell_length_c                   22.042(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.25(3)
_cell_angle_gamma                90
_cell_volume                     1275.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10689
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.471
_cell_measurement_theta_min      2.734
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.822
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  0.780
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'SADABS (SHELXTL-NT v5.1, Bruker)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10689
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_min         2.734
_diffrn_ambient_temperature      170
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2189
_reflns_number_total             2912
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2912
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0281P)²+0.8543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1117
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.75904(8) 0.88658(9) 0.12308(3) 0.04732(19) Uani 1 1 d . . . . .
S2 S 1.04633(9) 0.98176(11) 0.20396(3) 0.0573(2) Uani 1 1 d . . . . .
O1 O -0.0653(3) 0.5024(4) -0.15915(11) 0.0871(7) Uani 1 1 d . . . . .
O2 O -0.2489(3) 0.6341(3) -0.10214(11) 0.0774(7) Uani 1 1 d . . . . .
N1 N -0.1030(3) 0.5912(3) -0.11427(12) 0.0584(6) Uani 1 1 d . . . . .
C1 C 0.0327(3) 0.6472(3) -0.07310(12) 0.0456(6) Uani 1 1 d . . . . .
C2 C -0.0078(3) 0.7387(4) -0.02050(12) 0.0504(6) Uani 1 1 d . . . . .
H2 H -0.122363 0.765973 -0.011296 0.061 Uiso 1 1 calc R . . . .
C3 C 0.1196(3) 0.7897(4) 0.01837(12) 0.0484(6) Uani 1 1 d . . . . .
H3 H 0.092204 0.851939 0.054855 0.058 Uiso 1 1 calc R . . . .
C4 C 0.2895(3) 0.7520(3) 0.00535(11) 0.0432(6) Uani 1 1 d . . . . .
C5 C 0.3245(3) 0.6575(3) -0.04840(12) 0.0481(6) Uani 1 1 d . . . . .
H5 H 0.438517 0.628537 -0.057947 0.058 Uiso 1 1 calc R . . . .
C6 C 0.1977(3) 0.6059(3) -0.08763(12) 0.0488(6) Uani 1 1 d . . . . .
H6 H 0.223284 0.542860 -0.124118 0.059 Uiso 1 1 calc R . . . .
C7 C 0.4282(3) 0.8070(3) 0.04497(12) 0.0475(6) Uani 1 1 d . . . . .
H7 H 0.536652 0.758337 0.035922 0.057 Uiso 1 1 calc R . . . .
C8 C 0.4191(3) 0.9187(4) 0.09265(11) 0.0480(6) Uani 1 1 d . . . . .
H8 H 0.310760 0.967952 0.101476 0.058 Uiso 1 1 calc R . . . .
C9 C 0.5555(3) 0.9725(3) 0.13213(12) 0.0449(6) Uani 1 1 d . . . . .
C10 C 0.5508(3) 1.0863(4) 0.18082(12) 0.0525(7) Uani 1 1 d . . . . .
H10 H 0.450626 1.147042 0.193393 0.063 Uiso 1 1 calc R . . . .
C11 C 0.7072(3) 1.1065(4) 0.21107(12) 0.0527(7) Uani 1 1 d . . . . .
H11 H 0.722965 1.181253 0.245865 0.063 Uiso 1 1 calc R . . . .
C12 C 0.8337(3) 1.0072(3) 0.18503(11) 0.0445(6) Uani 1 1 d . . . . .
C13 C 1.0653(4) 1.1294(5) 0.26795(15) 0.0805(10) Uani 1 1 d . . . . .
H13A H 1.031637 1.253432 0.256332 0.121 Uiso 1 1 calc GR . . . .
H13B H 1.182966 1.130294 0.282159 0.121 Uiso 1 1 calc GR . . . .
H13C H 0.991713 1.085596 0.300528 0.121 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C9 1.739(3) . ?
S1 C12 1.728(3) . ?
S2 C12 1.740(3) . ?
S2 C13 1.783(3) . ?
O1 N1 1.222(3) . ?
O2 N1 1.226(3) . ?
N1 C1 1.461(3) . ?
C1 C2 1.378(4) . ?
C1 C6 1.377(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.371(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.402(3) . ?
C4 C5 1.400(3) . ?
C4 C7 1.456(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.374(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.333(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.438(4) . ?
C9 C10 1.360(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.410(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.365(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C12 S1 C9 92.14(12) . . ?
C12 S2 C13 101.69(14) . . ?
O1 N1 O2 123.1(3) . . ?
O1 N1 C1 118.1(2) . . ?
O2 N1 C1 118.8(3) . . ?
C2 C1 N1 119.1(2) . . ?
C6 C1 N1 119.2(2) . . ?
C6 C1 C2 121.7(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.3(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C7 122.8(2) . . ?
C5 C4 C3 117.6(2) . . ?
C5 C4 C7 119.6(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.5(2) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 H6 120.6 . . ?
C4 C7 H7 116.6 . . ?
C8 C7 C4 126.8(2) . . ?
C8 C7 H7 116.6 . . ?
C7 C8 H8 116.5 . . ?
C7 C8 C9 127.0(2) . . ?
C9 C8 H8 116.5 . . ?
C8 C9 S1 121.53(19) . . ?
C10 C9 S1 110.0(2) . . ?
C10 C9 C8 128.5(2) . . ?
C9 C10 H10 122.9 . . ?
C9 C10 C11 114.2(2) . . ?
C11 C10 H10 122.9 . . ?
C10 C11 H11 123.6 . . ?
C12 C11 C10 112.8(2) . . ?
C12 C11 H11 123.6 . . ?
S1 C12 S2 117.46(14) . . ?
C11 C12 S1 110.9(2) . . ?
C11 C12 S2 131.7(2) . . ?
S2 C13 H13A 109.5 . . ?
S2 C13 H13B 109.5 . . ?
S2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C13 H13B O1 0.98 2.56 3.463(4) 153.3 4_776 yes

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
S1 C9 C10 C11 0.1(3) . . . . ?
O1 N1 C1 C2 -176.4(3) . . . . ?
O1 N1 C1 C6 3.1(4) . . . . ?
O2 N1 C1 C2 3.1(4) . . . . ?
O2 N1 C1 C6 -177.4(2) . . . . ?
N1 C1 C2 C3 179.4(2) . . . . ?
N1 C1 C6 C5 -179.4(2) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C2 C3 C4 C7 178.8(2) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C3 C4 C7 C8 -10.1(4) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C4 C7 C8 C9 179.6(2) . . . . ?
C5 C4 C7 C8 169.8(3) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
C7 C4 C5 C6 -178.8(2) . . . . ?
C7 C8 C9 S1 -2.3(4) . . . . ?
C7 C8 C9 C10 179.7(3) . . . . ?
C8 C9 C10 C11 178.3(3) . . . . ?
C9 S1 C12 S2 179.62(15) . . . . ?
C9 S1 C12 C11 0.4(2) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C11 C12 S1 -0.4(3) . . . . ?
C10 C11 C12 S2 -179.5(2) . . . . ?
C12 S1 C9 C8 -178.6(2) . . . . ?
C12 S1 C9 C10 -0.3(2) . . . . ?
C13 S2 C12 S1 179.26(18) . . . . ?
C13 S2 C12 C11 -1.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound_2a
_database_code_depnum_ccdc_archive 'CCDC 2058513'
loop_
_audit_author_name
_audit_author_address
'Jari Konu'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-03-12 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT089_compound_2a         
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       2.65 Note
RESPONSE: Highly disordered structure in non-centrosymmetric space group with high number of parameters.
;
_audit_creation_date             2021-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 F N O2'
_chemical_formula_sum            'C16 H12 F N O2'
_chemical_formula_weight         269.27
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H12 F1 N1 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   7.1272(2)
_cell_length_b                   12.8757(4)
_cell_length_c                   7.3763(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.703(4)
_cell_angle_gamma                90
_cell_volume                     654.74(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2735
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.1180
_cell_measurement_theta_min      3.4030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_correction_T_min  0.746
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             280
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -1 4 0.1020
3 1 -4 0.1020
-1 -1 5 0.1490
1 1 -5 0.1860
0 1 0 0.0647
0 -1 0 0.0687
5 1 -1 0.2132
-5 -1 1 0.1472
1 -7 2 0.1090
4 -1 -3 0.1286
-3 5 2 0.0970
3 -6 -2 0.0979

_exptl_crystal_size_max          0.532
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.133
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.0000 -1.0000 4.0000 -0.1509 -0.6946 0.6577
3.0000 1.0000 -4.0000 0.1509 0.6946 -0.6577
-1.0000 -1.0000 5.0000 -0.0527 -0.3304 1.0361
1.0000 1.0000 -5.0000 0.0527 0.3304 -1.0361
-0.0000 1.0000 0.0000 -0.1132 0.0382 -0.0074
0.0000 -1.0000 -0.0000 0.1132 -0.0382 0.0074
5.0000 1.0000 -1.0000 0.2065 1.0189 0.1636
-5.0000 -1.0000 1.0000 -0.2065 -1.0189 -0.1636
1.0000 -7.0000 2.0000 0.8095 -0.1155 0.5732
4.0000 -1.0000 -3.0000 0.4157 0.7903 -0.3430
-3.0000 5.0000 2.0000 -0.7875 -0.4252 0.1704
3.0000 -6.0000 -2.0000 0.9007 0.3870 -0.1630

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4854
_diffrn_reflns_point_group_measured_fraction_full 0.702
_diffrn_reflns_point_group_measured_fraction_max 0.632
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         85.299
_diffrn_reflns_theta_min         3.433
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -18.00   1.00    2.00    --  -41.65 -57.00 150.00   95
  2  ω    -74.00  34.00   1.00    2.00    --  -41.65  77.00-120.00  108
  3  ω   -105.00 -21.00   1.00    2.00    --  -41.65 -57.00   0.00   84
  4  ω     -7.00  70.00   1.00    2.00    --   41.65 -57.00   0.00   77
  5  ω     36.00 116.00   1.00    8.00    --  112.00-111.00   0.00   80
  6  ω     31.00 154.00   1.00    8.00    --  112.00 -15.00 120.00  123
  7  ω     37.00 137.00   1.00    8.00    --  112.00 -30.00  30.00  100
  8  ω     33.00  73.00   1.00    8.00    --  112.00 -94.00-120.00   40
  9  ω     65.00 122.00   1.00    8.00    --  112.00-126.00 123.00   57
 10  ω    106.00 131.00   1.00    8.00    --  112.00 111.00 -90.00   25
 11  ω    152.00 178.00   1.00    8.00    --  112.00 111.00 -90.00   26
 12  ω     72.00 123.00   1.00    8.00    --  112.00 178.00  30.00   51
 13  ω    108.00 178.00   1.00    8.00    --  112.00  30.00 120.00   70
 14  ω     36.00 102.00   1.00    8.00    --  112.00 -94.00 -90.00   66
 15  ω     30.00 108.00   1.00    8.00    --  112.00 -94.00 120.00   78
 16  ω     46.00 136.00   1.00    8.00    --  112.00 -45.00 -60.00   90
 17  ω     40.00 104.00   1.00    8.00    --  112.00-111.00-150.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0596964000
_diffrn_orient_matrix_UB_12      -0.1131870000
_diffrn_orient_matrix_UB_13      -0.0212480000
_diffrn_orient_matrix_UB_21      0.1921401000
_diffrn_orient_matrix_UB_22      0.0382345000
_diffrn_orient_matrix_UB_23      -0.0199978000
_diffrn_orient_matrix_UB_31      0.0784816000
_diffrn_orient_matrix_UB_32      -0.0074046000
_diffrn_orient_matrix_UB_33      0.2214361000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.373
_reflns_Friedel_fraction_full    0.406
_reflns_Friedel_fraction_max     0.346
_reflns_number_gt                1777
_reflns_number_total             1881
_reflns_odcompleteness_completeness 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.094
_refine_diff_density_min         -0.105
_refine_diff_density_rms         0.022
_refine_ls_abs_structure_details 
;
 Flack x determined using 462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         1881
_refine_ls_number_restraints     484
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0648P)²+0.0266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0962
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1C-N1C \\sim O2C-N1C
 with sigma of 0.001
 O1C-C1C \\sim C1C-O2C
 with sigma of 0.001
 C5C-C1C \\sim C5B-C1B
 with sigma of 0.04
 N1C-O1C \\sim N1B-O1B
 with sigma of 0.02
 N1C-O2C \\sim N1B-O2B
 with sigma of 0.02
 N1C-C1C \\sim N1B-C1B
 with sigma of 0.02
 F1C-C14C \\sim F1B-C14B
 with sigma of 0.02
 C15C-C13C \\sim C15B-C13B
 with sigma of 0.04
 O2C-C1C \\sim O2B-C1B
 with sigma of 0.04
 C11C-C16C \\sim C11B-C16B
 with sigma of 0.02
 C11C-C12C \\sim C11B-C12B
 with sigma of 0.02
 C11C-C10C \\sim C11B-C10B
 with sigma of 0.02
 C6C-C2C \\sim C6B-C2B
 with sigma of 0.04
 C16C-C15C \\sim C16B-C15B
 with sigma of 0.02
 C15C-C14C \\sim C15B-C14B
 with sigma of 0.02
 C14C-C13C \\sim C14B-C13B
 with sigma of 0.02
 C16C-C10C \\sim C16B-C10B
 with sigma of 0.04
 C14C-C12C \\sim C14B-C12B
 with sigma of 0.04
 C13C-C12C \\sim C13B-C12B
 with sigma of 0.02
 C8C-C4C \\sim C8B-C4B
 with sigma of 0.04
 C9C-C8C \\sim C9B-C8B
 with sigma of 0.02
 C9C-C10C \\sim C9B-C10B
 with sigma of 0.02
 C7C-C3C \\sim C7B-C3B
 with sigma of 0.04
 C4C-C2C \\sim C4B-C2B
 with sigma of 0.04
 C8C-C7C \\sim C8B-C7B
 with sigma of 0.02
 C7C-C4C \\sim C7B-C4B
 with sigma of 0.02
 C4C-C5C \\sim C4B-C5B
 with sigma of 0.02
 C4C-C3C \\sim C4B-C3B
 with sigma of 0.02
 C5C-C6C \\sim C5B-C6B
 with sigma of 0.02
 C6C-C1C \\sim C6B-C1B
 with sigma of 0.02
 C12C-C10C \\sim C12B-C10B
 with sigma of 0.04
 C1C-C2C \\sim C1B-C2B
 with sigma of 0.02
 C9C-C7C \\sim C9B-C7B
 with sigma of 0.04
 C2C-C3C \\sim C2B-C3B
 with sigma of 0.02
 C8C-C10C \\sim C8B-C10B
 with sigma of 0.04
 N1C-C6C \\sim N1B-C6B
 with sigma of 0.04
 N1C-C2C \\sim N1B-C2B
 with sigma of 0.04
 C7C-C5C \\sim C7B-C5B
 with sigma of 0.04
 F1C-C15C \\sim F1B-C15B
 with sigma of 0.04
 F1C-C13C \\sim F1B-C13B
 with sigma of 0.04
 O1C-O2C \\sim O1B-O2B
 with sigma of 0.04
 C4C-C6C \\sim C4B-C6B
 with sigma of 0.04
 O1C-C1C \\sim O1B-C1B
 with sigma of 0.04
 C11C-C15C \\sim C11B-C15B
 with sigma of 0.04
 C11C-C13C \\sim C11B-C13B
 with sigma of 0.04
 C11C-C9C \\sim C11B-C9B
 with sigma of 0.04
 C5C-C3C \\sim C5B-C3B
 with sigma of 0.04
 C1C-C3C \\sim C1B-C3B
 with sigma of 0.04
 C16C-C14C \\sim C16B-C14B
 with sigma of 0.04
 C16C-C12C \\sim C16B-C12B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: F1A(0.4) O1A(0.4) O2A(0.4) N1A(0.4) C1A(0.4) C2A(0.4) H2A(0.4)
 C3A(0.4) H3A(0.4) C4A(0.4) C5A(0.4) H5A(0.4) C6A(0.4) H6A(0.4) C7A(0.4)
 H7A(0.4) C8A(0.4) H8A(0.4) C9A(0.4) H9A(0.4) C10A(0.4) H10A(0.4) C11A(0.4)
 C12A(0.4) H12A(0.4) C13A(0.4) H13A(0.4) C14A(0.4) C15A(0.4) H15A(0.4)
 C16A(0.4) H16A(0.4) F1B(0.4) O1B(0.4) O2B(0.4) N1B(0.4) C1B(0.4) C2B(0.4)
 H2B(0.4) C3B(0.4) H3B(0.4) C4B(0.4) C5B(0.4) H5B(0.4) C6B(0.4) H6B(0.4)
 C7B(0.4) H7B(0.4) C8B(0.4) H8B(0.4) C9B(0.4) H9B(0.4) C10B(0.4) H10B(0.4)
 C11B(0.4) C12B(0.4) H12B(0.4) C13B(0.4) H13B(0.4) C14B(0.4) C15B(0.4)
 H15B(0.4) C16B(0.4) H16B(0.4) F1C(0.2) O1C(0.2) O2C(0.2) N1C(0.2) C4C(0.2)
 C5C(0.2) H5C(0.2) C6C(0.2) H6C(0.2) C1C(0.2) C2C(0.2) H2C(0.2) C3C(0.2)
 H3C(0.2) C7C(0.2) H7C(0.2) C8C(0.2) H8C(0.2) C9C(0.2) H9C(0.2) C10C(0.2)
 H10C(0.2) C11C(0.2) C16C(0.2) H16C(0.2) C15C(0.2) H15C(0.2) C14C(0.2)
 C13C(0.2) H13C(0.2) C12C(0.2) H12C(0.2)
5.a Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A),
 C10A(H10A), C12A(H12A), C13A(H13A), C15A(H15A), C16A(H16A), C2B(H2B), C3B(H3B),
  C5B(H5B), C6B(H6B), C7B(H7B), C8B(H8B), C9B(H9B), C10B(H10B), C12B(H12B),
 C13B(H13B), C15B(H15B), C16B(H16B), C5C(H5C), C6C(H6C), C2C(H2C), C3C(H3C),
 C7C(H7C), C8C(H8C), C9C(H9C), C10C(H10C), C16C(H16C), C15C(H15C), C13C(H13C),
 C12C(H12C)
5.b Fitted hexagon refined as free rotating group:
 C4C(C5C,C6C,C1C,C2C,C3C), C11C(C16C,C15C,C14C,C13C,C12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1A F 1.4901(11) 0.9102(5) 1.1098(10) 0.0478(15) Uani 0.4 1 d . U P A 1
O1A O -0.3490(10) 0.5195(6) -0.2031(14) 0.0590(16) Uani 0.4 1 d . U P A 1
O2A O -0.4550(11) 0.6339(5) -0.0318(14) 0.0556(15) Uani 0.4 1 d . U P A 1
N1A N -0.3212(15) 0.5886(8) -0.071(2) 0.0403(17) Uani 0.4 1 d . U P A 1
C1A C -0.1281(12) 0.6102(7) 0.0438(16) 0.0344(17) Uani 0.4 1 d . U P A 1
C2A C -0.0975(12) 0.6973(6) 0.1654(13) 0.0353(16) Uani 0.4 1 d . U P A 1
H2A H -0.199986 0.739819 0.175050 0.042 Uiso 0.4 1 calc R . P A 1
C3A C 0.0821(12) 0.7160(7) 0.2649(16) 0.0356(17) Uani 0.4 1 d . U P A 1
H3A H 0.108112 0.774008 0.342385 0.043 Uiso 0.4 1 calc R . P A 1
C4A C 0.2303(12) 0.6493(7) 0.2535(14) 0.0362(16) Uani 0.4 1 d . U P A 1
C5A C 0.1928(11) 0.5609(7) 0.1349(15) 0.0392(18) Uani 0.4 1 d . U P A 1
H5A H 0.293564 0.515752 0.130948 0.047 Uiso 0.4 1 calc R . P A 1
C6A C 0.0146(13) 0.5417(8) 0.0290(16) 0.0340(17) Uani 0.4 1 d . U P A 1
H6A H -0.011540 0.484680 -0.050956 0.041 Uiso 0.4 1 calc R . P A 1
C7A C 0.4304(12) 0.6705(8) 0.3688(16) 0.049(2) Uani 0.4 1 d . U P A 1
H7A H 0.522226 0.620592 0.360556 0.059 Uiso 0.4 1 calc R . P A 1
C8A C 0.495(2) 0.7472(12) 0.478(2) 0.045(3) Uani 0.4 1 d . U P A 1
H8A H 0.406300 0.797460 0.491478 0.054 Uiso 0.4 1 calc R . P A 1
C9A C 0.6931(15) 0.7621(9) 0.5803(17) 0.046(2) Uani 0.4 1 d . U P A 1
H9A H 0.779501 0.710019 0.568093 0.055 Uiso 0.4 1 calc R . P A 1
C10A C 0.7671(12) 0.8403(6) 0.6894(15) 0.0438(18) Uani 0.4 1 d . U P A 1
H10A H 0.680638 0.893567 0.695018 0.053 Uiso 0.4 1 calc R . P A 1
C11A C 0.9566(13) 0.8555(9) 0.7986(15) 0.0401(19) Uani 0.4 1 d . U P A 1
C12A C 0.9995(16) 0.9408(7) 0.9170(16) 0.0446(18) Uani 0.4 1 d . U P A 1
H12A H 0.900155 0.986023 0.925051 0.054 Uiso 0.4 1 calc R . P A 1
C13A C 1.1817(15) 0.9600(6) 1.0209(13) 0.0397(15) Uani 0.4 1 d . U P A 1
H13A H 1.210359 1.017537 1.099246 0.048 Uiso 0.4 1 calc R . P A 1
C14A C 1.3156(14) 0.8933(7) 1.0054(15) 0.0394(17) Uani 0.4 1 d . U P A 1
C15A C 1.2798(12) 0.8040(7) 0.8845(15) 0.0325(17) Uani 0.4 1 d . U P A 1
H15A H 1.380103 0.759383 0.876662 0.039 Uiso 0.4 1 calc R . P A 1
C16A C 1.0975(14) 0.7867(8) 0.7831(16) 0.0361(18) Uani 0.4 1 d . U P A 1
H16A H 1.068024 0.729309 0.704409 0.043 Uiso 0.4 1 calc R . P A 1
F1B F -0.3839(13) 0.5866(9) -0.0825(16) 0.072(3) Uani 0.4 1 d D U P B 2
O1B O 1.5652(7) 0.8735(5) 1.0789(10) 0.0532(13) Uani 0.4 1 d D U P B 2
O2B O 1.4508(10) 0.9838(5) 1.2396(11) 0.0630(17) Uani 0.4 1 d D U P B 2
N1B N 1.4314(12) 0.9248(9) 1.1161(17) 0.0364(17) Uani 0.4 1 d D U P B 2
C1B C 1.2447(10) 0.8980(7) 1.0004(14) 0.0316(16) Uani 0.4 1 d D U P B 2
C2B C 1.1046(11) 0.9633(6) 1.0150(14) 0.0329(18) Uani 0.4 1 d D U P B 2
H2B H 1.129275 1.020293 1.095050 0.039 Uiso 0.4 1 calc R . P B 2
C3B C 0.9227(10) 0.9425(5) 0.9063(11) 0.0291(13) Uani 0.4 1 d D U P B 2
H3B H 0.821337 0.986506 0.913598 0.035 Uiso 0.4 1 calc R . P B 2
C4B C 0.8829(10) 0.8560(5) 0.7825(11) 0.0267(13) Uani 0.4 1 d D U P B 2
C5B C 1.0295(12) 0.7909(6) 0.7770(14) 0.0298(15) Uani 0.4 1 d D U P B 2
H5B H 1.006001 0.732835 0.699618 0.036 Uiso 0.4 1 calc R . P B 2
C6B C 1.2113(11) 0.8098(6) 0.8841(14) 0.0339(15) Uani 0.4 1 d D U P B 2
H6B H 1.312615 0.764978 0.880539 0.041 Uiso 0.4 1 calc R . P B 2
C7B C 0.6925(10) 0.8401(4) 0.6744(9) 0.0265(12) Uani 0.4 1 d D U P B 2
H7B H 0.603738 0.892892 0.675485 0.032 Uiso 0.4 1 calc R . P B 2
C8B C 0.6238(14) 0.7534(6) 0.5661(12) 0.0257(16) Uani 0.4 1 d D U P B 2
H8B H 0.709233 0.699298 0.562719 0.031 Uiso 0.4 1 calc R . P B 2
C9B C 0.4293(12) 0.7442(7) 0.4609(12) 0.0303(19) Uani 0.4 1 d D U P B 2
H9B H 0.343133 0.797604 0.466674 0.036 Uiso 0.4 1 calc R . P B 2
C10B C 0.3629(11) 0.6602(6) 0.3512(11) 0.0341(15) Uani 0.4 1 d D U P B 2
H10B H 0.451460 0.608325 0.343557 0.041 Uiso 0.4 1 calc R . P B 2
C11B C 0.1604(12) 0.6461(7) 0.2440(13) 0.0333(17) Uani 0.4 1 d D U P B 2
C12B C 0.0113(14) 0.7115(6) 0.2496(14) 0.0339(17) Uani 0.4 1 d D U P B 2
H12B H 0.029891 0.768916 0.328509 0.041 Uiso 0.4 1 calc R . P B 2
C13B C -0.1639(14) 0.6892(9) 0.1357(17) 0.046(2) Uani 0.4 1 d D U P B 2
H13B H -0.266900 0.733609 0.135665 0.055 Uiso 0.4 1 calc R . P B 2
C14B C -0.1972(14) 0.6054(8) 0.0216(15) 0.043(2) Uani 0.4 1 d D U P B 2
C15B C -0.0555(14) 0.5384(8) 0.0096(14) 0.045(2) Uani 0.4 1 d D U P B 2
H15B H -0.078427 0.482159 -0.072034 0.054 Uiso 0.4 1 calc R . P B 2
C16B C 0.1222(13) 0.5580(7) 0.1237(14) 0.0377(17) Uani 0.4 1 d D U P B 2
H16B H 0.223052 0.512222 0.123252 0.045 Uiso 0.4 1 calc R . P B 2
F1C F 1.426(2) 0.9652(13) 1.137(3) 0.092(5) Uani 0.2 1 d D U P C 3
O1C O -0.2925(17) 0.4901(11) -0.149(2) 0.080(5) Uani 0.2 1 d D U P C 3
O2C O -0.4845(14) 0.5992(13) -0.071(3) 0.076(4) Uani 0.2 1 d D U P C 3
N1C N -0.332(2) 0.5613(14) -0.064(3) 0.052(4) Uani 0.2 1 d D U P C 3
C4C C 0.1516(11) 0.7014(8) 0.2929(13) 0.034(2) Uani 0.2 1 d D U P C 3
C5C C 0.1703(12) 0.6101(8) 0.1983(16) 0.032(2) Uani 0.2 1 d DG U P C 3
H5C H 0.291430 0.579308 0.214522 0.039 Uiso 0.2 1 calc R . P C 3
C6C C 0.0079(16) 0.5650(8) 0.0792(19) 0.038(3) Uani 0.2 1 d DG U P C 3
H6C H 0.020396 0.503975 0.015892 0.046 Uiso 0.2 1 calc R . P C 3
C1C C -0.1732(13) 0.6111(11) 0.055(2) 0.038(4) Uani 0.2 1 d DG U P C 3
C2C C -0.1919(11) 0.7023(10) 0.150(2) 0.038(3) Uani 0.2 1 d DG U P C 3
H2C H -0.313006 0.733121 0.133352 0.046 Uiso 0.2 1 calc R . P C 3
C3C C -0.0295(14) 0.7474(6) 0.2686(14) 0.034(2) Uani 0.2 1 d DG U P C 3
H3C H -0.041974 0.808456 0.331983 0.041 Uiso 0.2 1 calc R . P C 3
C7C C 0.3032(18) 0.7525(9) 0.4126(18) 0.039(2) Uani 0.2 1 d D U P C 3
H7C H 0.269451 0.810668 0.472119 0.047 Uiso 0.2 1 calc R . P C 3
C8C C 0.495(3) 0.730(3) 0.455(5) 0.043(5) Uani 0.2 1 d D U P C 3
H8C H 0.537190 0.673226 0.397356 0.052 Uiso 0.2 1 calc R . P C 3
C9C C 0.631(2) 0.7895(13) 0.585(3) 0.035(3) Uani 0.2 1 d D U P C 3
H9C H 0.595078 0.850517 0.635265 0.042 Uiso 0.2 1 calc R . P C 3
C10C C 0.8168(17) 0.7539(9) 0.6344(17) 0.041(2) Uani 0.2 1 d D U P C 3
H10C H 0.843933 0.690890 0.585033 0.049 Uiso 0.2 1 calc R . P C 3
C11C C 0.9762(14) 0.8099(11) 0.7609(18) 0.043(3) Uani 0.2 1 d D U P C 3
C16C C 1.1648(18) 0.7726(10) 0.793(2) 0.055(4) Uani 0.2 1 d DG U P C 3
H16C H 1.190024 0.713374 0.730564 0.066 Uiso 0.2 1 calc R . P C 3
C15C C 1.3157(13) 0.8240(14) 0.917(3) 0.062(4) Uani 0.2 1 d DG U P C 3
H15C H 1.441855 0.799040 0.937814 0.074 Uiso 0.2 1 calc R . P C 3
C14C C 1.278(2) 0.9125(14) 1.009(3) 0.066(6) Uani 0.2 1 d DG U P C 3
C13C C 1.089(3) 0.9498(11) 0.978(3) 0.064(6) Uani 0.2 1 d DG U P C 3
H13C H 1.064103 1.009009 1.039597 0.077 Uiso 0.2 1 calc R . P C 3
C12C C 0.9385(17) 0.8984(11) 0.853(2) 0.048(3) Uani 0.2 1 d DG U P C 3
H12C H 0.812268 0.923344 0.832348 0.058 Uiso 0.2 1 calc R . P C 3


_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
F1A C14A 1.304(11) . ?
O1A N1A 1.296(13) . ?
O2A N1A 1.215(12) . ?
N1A C1A 1.448(11) . ?
C1A C2A 1.418(10) . ?
C1A C6A 1.371(9) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.326(10) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.381(10) . ?
C4A C5A 1.420(11) . ?
C4A C7A 1.488(10) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.334(11) . ?
C6A H6A 0.9300 . ?
C7A H7A 0.9300 . ?
C7A C8A 1.283(15) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.433(12) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.313(13) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.399(11) . ?
C11A C12A 1.388(15) . ?
C11A C16A 1.366(11) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.353(12) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.310(11) . ?
C14A C15A 1.439(10) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.343(10) . ?
C16A H16A 0.9300 . ?
F1B C14B 1.378(8) . ?
O1B N1B 1.246(8) . ?
O2B N1B 1.167(13) . ?
N1B C1B 1.428(9) . ?
C1B C2B 1.331(9) . ?
C1B C6B 1.407(10) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.367(8) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.424(8) . ?
C4B C5B 1.348(9) . ?
C4B C7B 1.403(8) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.357(9) . ?
C6B H6B 0.9300 . ?
C7B H7B 0.9300 . ?
C7B C8B 1.388(8) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.411(8) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.362(9) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.470(9) . ?
C11B C12B 1.364(11) . ?
C11B C16B 1.423(10) . ?
C12B H12B 0.9300 . ?
C12B C13B 1.347(9) . ?
C13B H13B 0.9300 . ?
C13B C14B 1.353(12) . ?
C14B C15B 1.347(13) . ?
C15B H15B 0.9300 . ?
C15B C16B 1.355(9) . ?
C16B H16B 0.9300 . ?
F1C C14C 1.402(16) . ?
O1C N1C 1.182(11) . ?
O2C N1C 1.182(11) . ?
N1C C1C 1.399(18) . ?
C4C C5C 1.3900 . ?
C4C C3C 1.3900 . ?
C4C C7C 1.377(14) . ?
C5C H5C 0.9300 . ?
C5C C6C 1.3900 . ?
C6C H6C 0.9300 . ?
C6C C1C 1.3900 . ?
C1C C2C 1.3900 . ?
C2C H2C 0.9300 . ?
C2C C3C 1.3900 . ?
C3C H3C 0.9300 . ?
C7C H7C 0.9300 . ?
C7C C8C 1.35(2) . ?
C8C H8C 0.9300 . ?
C8C C9C 1.41(2) . ?
C9C H9C 0.9300 . ?
C9C C10C 1.363(15) . ?
C10C H10C 0.9300 . ?
C10C C11C 1.463(15) . ?
C11C C16C 1.3900 . ?
C11C C12C 1.3900 . ?
C16C H16C 0.9300 . ?
C16C C15C 1.3900 . ?
C15C H15C 0.9300 . ?
C15C C14C 1.3900 . ?
C14C C13C 1.3900 . ?
C13C H13C 0.9300 . ?
C13C C12C 1.3900 . ?
C12C H12C 0.9300 . ?

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
O1A N1A C1A 120.9(7) . . ?
O2A N1A O1A 121.9(9) . . ?
O2A N1A C1A 117.1(9) . . ?
C2A C1A N1A 119.5(7) . . ?
C6A C1A N1A 116.3(8) . . ?
C6A C1A C2A 124.1(8) . . ?
C1A C2A H2A 121.1 . . ?
C3A C2A C1A 117.8(7) . . ?
C3A C2A H2A 121.1 . . ?
C2A C3A H3A 120.0 . . ?
C2A C3A C4A 120.0(7) . . ?
C4A C3A H3A 120.0 . . ?
C3A C4A C5A 120.6(7) . . ?
C3A C4A C7A 119.2(8) . . ?
C5A C4A C7A 120.2(7) . . ?
C4A C5A H5A 119.6 . . ?
C6A C5A C4A 120.8(7) . . ?
C6A C5A H5A 119.6 . . ?
C1A C6A H6A 121.7 . . ?
C5A C6A C1A 116.7(8) . . ?
C5A C6A H6A 121.7 . . ?
C4A C7A H7A 115.1 . . ?
C8A C7A C4A 129.8(10) . . ?
C8A C7A H7A 115.1 . . ?
C7A C8A H8A 117.1 . . ?
C7A C8A C9A 125.7(13) . . ?
C9A C8A H8A 117.1 . . ?
C8A C9A H9A 116.0 . . ?
C10A C9A C8A 127.9(11) . . ?
C10A C9A H9A 116.0 . . ?
C9A C10A H10A 115.1 . . ?
C9A C10A C11A 129.7(9) . . ?
C11A C10A H10A 115.1 . . ?
C12A C11A C10A 119.9(10) . . ?
C16A C11A C10A 118.9(10) . . ?
C16A C11A C12A 121.1(9) . . ?
C11A C12A H12A 119.1 . . ?
C13A C12A C11A 121.8(9) . . ?
C13A C12A H12A 119.1 . . ?
C12A C13A H13A 121.7 . . ?
C14A C13A C12A 116.6(7) . . ?
C14A C13A H13A 121.7 . . ?
F1A C14A C13A 116.5(8) . . ?
F1A C14A C15A 119.5(7) . . ?
C13A C14A C15A 124.0(8) . . ?
C14A C15A H15A 120.9 . . ?
C16A C15A C14A 118.2(7) . . ?
C16A C15A H15A 120.9 . . ?
C11A C16A H16A 120.9 . . ?
C15A C16A C11A 118.3(8) . . ?
C15A C16A H16A 120.9 . . ?
O1B N1B C1B 112.9(8) . . ?
O2B N1B O1B 124.8(9) . . ?
O2B N1B C1B 122.1(8) . . ?
C2B C1B N1B 113.8(7) . . ?
C2B C1B C6B 123.0(7) . . ?
C6B C1B N1B 123.2(7) . . ?
C1B C2B H2B 121.7 . . ?
C1B C2B C3B 116.7(7) . . ?
C3B C2B H2B 121.7 . . ?
C2B C3B H3B 118.8 . . ?
C2B C3B C4B 122.3(6) . . ?
C4B C3B H3B 118.8 . . ?
C5B C4B C3B 118.4(6) . . ?
C5B C4B C7B 122.6(6) . . ?
C7B C4B C3B 119.0(6) . . ?
C4B C5B H5B 119.9 . . ?
C4B C5B C6B 120.3(7) . . ?
C6B C5B H5B 119.9 . . ?
C1B C6B H6B 120.4 . . ?
C5B C6B C1B 119.2(7) . . ?
C5B C6B H6B 120.4 . . ?
C4B C7B H7B 116.8 . . ?
C8B C7B C4B 126.4(6) . . ?
C8B C7B H7B 116.8 . . ?
C7B C8B H8B 118.7 . . ?
C7B C8B C9B 122.6(9) . . ?
C9B C8B H8B 118.7 . . ?
C8B C9B H9B 118.7 . . ?
C10B C9B C8B 122.6(8) . . ?
C10B C9B H9B 118.7 . . ?
C9B C10B H10B 117.9 . . ?
C9B C10B C11B 124.3(8) . . ?
C11B C10B H10B 117.9 . . ?
C12B C11B C10B 125.0(7) . . ?
C12B C11B C16B 118.9(7) . . ?
C16B C11B C10B 116.1(8) . . ?
C11B C12B H12B 121.4 . . ?
C13B C12B C11B 117.1(8) . . ?
C13B C12B H12B 121.4 . . ?
C12B C13B H13B 118.5 . . ?
C12B C13B C14B 123.1(9) . . ?
C14B C13B H13B 118.5 . . ?
C13B C14B F1B 118.6(10) . . ?
C15B C14B F1B 119.0(9) . . ?
C15B C14B C13B 122.4(8) . . ?
C14B C15B H15B 122.0 . . ?
C14B C15B C16B 116.0(7) . . ?
C16B C15B H15B 122.0 . . ?
C11B C16B H16B 118.8 . . ?
C15B C16B C11B 122.4(8) . . ?
C15B C16B H16B 118.8 . . ?
O1C N1C C1C 115.2(9) . . ?
O2C N1C O1C 129.4(19) . . ?
O2C N1C C1C 115.2(9) . . ?
C5C C4C C3C 120.0 . . ?
C7C C4C C5C 124.5(8) . . ?
C7C C4C C3C 115.5(8) . . ?
C4C C5C H5C 120.0 . . ?
C4C C5C C6C 120.0 . . ?
C6C C5C H5C 120.0 . . ?
C5C C6C H6C 120.0 . . ?
C1C C6C C5C 120.0 . . ?
C1C C6C H6C 120.0 . . ?
C6C C1C N1C 117.4(6) . . ?
C6C C1C C2C 120.0 . . ?
C2C C1C N1C 122.6(6) . . ?
C1C C2C H2C 120.0 . . ?
C3C C2C C1C 120.0 . . ?
C3C C2C H2C 120.0 . . ?
C4C C3C H3C 120.0 . . ?
C2C C3C C4C 120.0 . . ?
C2C C3C H3C 120.0 . . ?
C4C C7C H7C 115.7 . . ?
C8C C7C C4C 128.7(14) . . ?
C8C C7C H7C 115.7 . . ?
C7C C8C H8C 119.4 . . ?
C7C C8C C9C 121.1(19) . . ?
C9C C8C H8C 119.4 . . ?
C8C C9C H9C 121.6 . . ?
C10C C9C C8C 116.9(15) . . ?
C10C C9C H9C 121.6 . . ?
C9C C10C H10C 118.3 . . ?
C9C C10C C11C 123.4(13) . . ?
C11C C10C H10C 118.3 . . ?
C16C C11C C10C 119.9(11) . . ?
C16C C11C C12C 120.0 . . ?
C12C C11C C10C 120.1(11) . . ?
C11C C16C H16C 120.0 . . ?
C15C C16C C11C 120.0 . . ?
C15C C16C H16C 120.0 . . ?
C16C C15C H15C 120.0 . . ?
C14C C15C C16C 120.0 . . ?
C14C C15C H15C 120.0 . . ?
C15C C14C F1C 121.4(14) . . ?
C15C C14C C13C 120.0 . . ?
C13C C14C F1C 118.6(14) . . ?
C14C C13C H13C 120.0 . . ?
C12C C13C C14C 120.0 . . ?
C12C C13C H13C 120.0 . . ?
C11C C12C H12C 120.0 . . ?
C13C C12C C11C 120.0 . . ?
C13C C12C H12C 120.0 . . ?

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
F1A C14A C15A C16A 177.9(10) . . . . ?
O1A N1A C1A C2A 169.6(11) . . . . ?
O1A N1A C1A C6A -11.6(15) . . . . ?
O2A N1A C1A C2A -14.1(15) . . . . ?
O2A N1A C1A C6A 164.6(10) . . . . ?
N1A C1A C2A C3A -178.3(9) . . . . ?
N1A C1A C6A C5A -179.8(9) . . . . ?
C1A C2A C3A C4A -2.5(13) . . . . ?
C2A C1A C6A C5A -1.1(13) . . . . ?
C2A C3A C4A C5A 0.4(13) . . . . ?
C2A C3A C4A C7A -178.9(8) . . . . ?
C3A C4A C5A C6A 1.5(13) . . . . ?
C3A C4A C7A C8A -3.7(18) . . . . ?
C4A C5A C6A C1A -1.1(13) . . . . ?
C4A C7A C8A C9A -178.4(12) . . . . ?
C5A C4A C7A C8A 177.0(15) . . . . ?
C6A C1A C2A C3A 3.0(14) . . . . ?
C7A C4A C5A C6A -179.1(8) . . . . ?
C7A C8A C9A C10A 178.1(14) . . . . ?
C8A C9A C10A C11A 176.6(13) . . . . ?
C9A C10A C11A C12A -174.4(10) . . . . ?
C9A C10A C11A C16A 7.0(15) . . . . ?
C10A C11A C12A C13A -178.1(8) . . . . ?
C10A C11A C16A C15A 178.0(9) . . . . ?
C11A C12A C13A C14A -0.6(13) . . . . ?
C12A C11A C16A C15A -0.5(14) . . . . ?
C12A C13A C14A F1A -178.1(8) . . . . ?
C12A C13A C14A C15A 0.9(13) . . . . ?
C13A C14A C15A C16A -1.1(14) . . . . ?
C14A C15A C16A C11A 0.8(14) . . . . ?
C16A C11A C12A C13A 0.4(14) . . . . ?
F1B C14B C15B C16B -176.3(9) . . . . ?
O1B N1B C1B C2B -169.0(10) . . . . ?
O1B N1B C1B C6B 12.0(16) . . . . ?
O2B N1B C1B C2B 15.8(16) . . . . ?
O2B N1B C1B C6B -163.3(12) . . . . ?
N1B C1B C2B C3B 179.4(9) . . . . ?
N1B C1B C6B C5B -179.2(9) . . . . ?
C1B C2B C3B C4B -0.3(13) . . . . ?
C2B C1B C6B C5B 1.8(15) . . . . ?
C2B C3B C4B C5B 2.0(12) . . . . ?
C2B C3B C4B C7B -179.6(7) . . . . ?
C3B C4B C5B C6B -1.7(11) . . . . ?
C3B C4B C7B C8B -171.1(7) . . . . ?
C4B C5B C6B C1B 0.0(13) . . . . ?
C4B C7B C8B C9B -179.8(7) . . . . ?
C5B C4B C7B C8B 7.3(11) . . . . ?
C6B C1B C2B C3B -1.6(14) . . . . ?
C7B C4B C5B C6B 179.9(8) . . . . ?
C7B C8B C9B C10B 178.5(8) . . . . ?
C8B C9B C10B C11B 178.0(7) . . . . ?
C9B C10B C11B C12B -4.3(13) . . . . ?
C9B C10B C11B C16B 174.3(9) . . . . ?
C10B C11B C12B C13B 177.1(9) . . . . ?
C10B C11B C16B C15B -176.5(8) . . . . ?
C11B C12B C13B C14B 1.2(16) . . . . ?
C12B C11B C16B C15B 2.2(14) . . . . ?
C12B C13B C14B F1B 176.8(11) . . . . ?
C12B C13B C14B C15B -1.6(17) . . . . ?
C13B C14B C15B C16B 2.1(14) . . . . ?
C14B C15B C16B C11B -2.4(14) . . . . ?
C16B C11B C12B C13B -1.5(13) . . . . ?
F1C C14C C13C C12C -179.1(19) . . . . ?
O1C N1C C1C C6C -8(3) . . . . ?
O1C N1C C1C C2C 173.1(16) . . . . ?
O2C N1C C1C C6C 175.2(18) . . . . ?
O2C N1C C1C C2C -4(3) . . . . ?
N1C C1C C2C C3C 179(2) . . . . ?
C4C C5C C6C C1C 0.0 . . . . ?
C4C C7C C8C C9C -178(2) . . . . ?
C5C C4C C3C C2C 0.0 . . . . ?
C5C C4C C7C C8C 3(3) . . . . ?
C5C C6C C1C N1C -179.1(19) . . . . ?
C5C C6C C1C C2C 0.0 . . . . ?
C6C C1C C2C C3C 0.0 . . . . ?
C1C C2C C3C C4C 0.0 . . . . ?
C3C C4C C5C C6C 0.0 . . . . ?
C3C C4C C7C C8C -176(3) . . . . ?
C7C C4C C5C C6C -179.5(12) . . . . ?
C7C C4C C3C C2C 179.5(11) . . . . ?
C7C C8C C9C C10C 173(3) . . . . ?
C8C C9C C10C C11C 177(2) . . . . ?
C9C C10C C11C C16C -174.9(14) . . . . ?
C9C C10C C11C C12C 7(2) . . . . ?
C10C C11C C16C C15C -178.2(14) . . . . ?
C10C C11C C12C C13C 178.2(14) . . . . ?
C11C C16C C15C C14C 0.0 . . . . ?
C16C C11C C12C C13C 0.0 . . . . ?
C16C C15C C14C F1C 179.0(19) . . . . ?
C16C C15C C14C C13C 0.0 . . . . ?
C15C C14C C13C C12C 0.0 . . . . ?
C14C C13C C12C C11C 0.0 . . . . ?
C12C C11C C16C C15C 0.0 . . . . ?


_ins_header                      
;
TITL ek1926_a_Pc_small in Pc 
REM Pc (#7 in standard setting)
CELL 1.54184   7.376128  12.878279   7.126359  90.0000 104.7024  90.0000
ZERR    2.00   0.000357   0.000410   0.000224   0.0000   0.0040   0.0000
LATT -1
SYMM  x,-y, z+1/2 
SFAC C H N O F
UNIT 32.00 24.00 2.00 4.00 2.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.521
_oxdiff_exptl_absorpt_empirical_full_min 0.660
####################################################################### 
# 
# 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_compound_3a_mono
_database_code_depnum_ccdc_archive 'CCDC 2058514'
loop_
_audit_author_name
_audit_author_address
'Jari Konu'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 Br N O2 S'
_chemical_formula_sum            'C12 H8 Br N O2 S'
_chemical_formula_weight         310.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.1458(5)
_cell_length_b                   15.8649(6)
_cell_length_c                   14.8141(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.260(5)
_cell_angle_gamma                90
_cell_volume                     2330.13(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4167
_cell_measurement_temperature    122(2)
_cell_measurement_theta_max      28.3570
_cell_measurement_theta_min      2.3970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.694
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.994
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 3 -5 0.0644
-3 -5 2 0.1220
3 5 -2 0.0730
-5 3 5 0.0843
5 -3 -5 0.0843
0 -5 -2 0.1507
2 -3 5 0.0994
-1 1 5 0.0959
1 -1 -5 0.1219

_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.164
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0019 2.9856 -5.0051 0.0984 0.3055 -0.1027
-3.0097 -4.9863 1.9918 0.2262 -0.0518 0.2068
3.0097 4.9863 -1.9918 -0.2262 0.0518 -0.2068
-4.9962 2.9992 4.9923 0.3596 -0.1061 -0.1667
4.9962 -2.9992 -4.9923 -0.3596 0.1061 0.1667
-0.0099 -4.9914 -2.0032 0.0002 0.0699 0.2334
2.0019 -2.9856 5.0051 -0.0984 -0.3055 0.1027
-0.9978 1.0092 4.9997 0.0947 -0.2123 -0.0761
0.9978 -1.0092 -4.9997 -0.0947 0.2123 0.0761

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.493
_diffrn_reflns_theta_min         1.904
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      122(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  24.00   1.00   20.00    --  -16.91 -99.00 120.00   36
  2  ω      6.00  84.00   1.00   20.00    --   18.01  57.00-180.00   78
  3  ω    -51.00  32.00   1.00   20.00    --   18.01 -57.00-150.00   83
  4  ω     -4.00  44.00   1.00   20.00    --   18.01 -37.00-150.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0674295000
_diffrn_orient_matrix_UB_12      -0.0022967000
_diffrn_orient_matrix_UB_13      0.0059378000
_diffrn_orient_matrix_UB_21      -0.0237513000
_diffrn_orient_matrix_UB_22      0.0054315000
_diffrn_orient_matrix_UB_23      -0.0482923000
_diffrn_orient_matrix_UB_31      0.0006205000
_diffrn_orient_matrix_UB_32      -0.0443025000
_diffrn_orient_matrix_UB_33      -0.0061489000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3951
_reflns_number_total             5067
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5067
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0303P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0823
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C12(H12), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.00823(3) 1.04613(2) 0.62439(2) 0.02303(10) Uani 1 1 d . . . . .
S1 S 1.19623(8) 0.80665(4) 0.72203(5) 0.02220(18) Uani 1 1 d . . . . .
O1 O 1.0117(2) 0.23837(12) 0.60491(15) 0.0342(6) Uani 1 1 d . . . . .
O2 O 0.8104(2) 0.27180(12) 0.53317(14) 0.0280(5) Uani 1 1 d . . . . .
N1 N 0.9235(3) 0.29074(14) 0.57588(17) 0.0217(6) Uani 1 1 d . . . . .
C1 C 0.9560(3) 0.37992(16) 0.59364(19) 0.0184(7) Uani 1 1 d . . . . .
C2 C 0.8568(3) 0.44021(17) 0.56630(19) 0.0200(7) Uani 1 1 d . . . . .
H2 H 0.770078 0.424695 0.536448 0.024 Uiso 1 1 calc R . . . .
C3 C 0.8895(3) 0.52371(17) 0.58435(19) 0.0194(7) Uani 1 1 d . . . . .
H3 H 0.824205 0.564971 0.566001 0.023 Uiso 1 1 calc R . . . .
C4 C 1.0201(3) 0.54745(18) 0.63006(18) 0.0191(7) Uani 1 1 d . . . . .
C5 C 1.1166(3) 0.48429(17) 0.65607(19) 0.0213(7) Uani 1 1 d . . . . .
H5 H 1.203671 0.499042 0.686027 0.026 Uiso 1 1 calc R . . . .
C6 C 1.0855(3) 0.40056(17) 0.63819(18) 0.0189(7) Uani 1 1 d . . . . .
H6 H 1.150322 0.358901 0.655795 0.023 Uiso 1 1 calc R . . . .
C7 C 1.0617(3) 0.63461(17) 0.6514(2) 0.0231(7) Uani 1 1 d . . . . .
H7 H 1.147194 0.641994 0.688464 0.028 Uiso 1 1 calc R . . . .
C8 C 0.9924(3) 0.70486(18) 0.6245(2) 0.0224(7) Uani 1 1 d . . . . .
H8 H 0.906311 0.699266 0.587866 0.027 Uiso 1 1 calc R . . . .
C9 C 1.0419(3) 0.78909(17) 0.6483(2) 0.0195(7) Uani 1 1 d . . . . .
C10 C 0.9818(3) 0.86354(18) 0.6181(2) 0.0224(7) Uani 1 1 d . . . . .
H10 H 0.897903 0.867604 0.578097 0.027 Uiso 1 1 calc R . . . .
C11 C 1.0606(3) 0.93370(16) 0.65395(19) 0.0179(6) Uani 1 1 d . . . . .
C12 C 1.1789(3) 0.91374(16) 0.71118(19) 0.0204(7) Uani 1 1 d . . . . .
H12 H 1.242041 0.952753 0.740579 0.024 Uiso 1 1 calc R . . . .
Br2 Br 0.50373(3) 0.47797(2) 0.37037(2) 0.02465(10) Uani 1 1 d . . . . .
S2 S 0.30277(8) 0.23748(5) 0.29757(5) 0.02352(19) Uani 1 1 d . . . . .
O3 O 0.7012(2) -0.29713(12) 0.45812(15) 0.0311(6) Uani 1 1 d . . . . .
O4 O 0.4955(3) -0.33054(13) 0.39447(16) 0.0389(6) Uani 1 1 d . . . . .
N2 N 0.5855(3) -0.27879(15) 0.42124(17) 0.0240(6) Uani 1 1 d . . . . .
C13 C 0.5507(3) -0.18928(16) 0.40824(19) 0.0183(7) Uani 1 1 d . . . . .
C14 C 0.4167(3) -0.16673(17) 0.38559(19) 0.0205(7) Uani 1 1 d . . . . .
H14 H 0.349423 -0.207511 0.378713 0.025 Uiso 1 1 calc R . . . .
C15 C 0.3840(3) -0.08252(16) 0.37329(19) 0.0203(7) Uani 1 1 d . . . . .
H15 H 0.293775 -0.066644 0.358392 0.024 Uiso 1 1 calc R . . . .
C16 C 0.4841(3) -0.02048(17) 0.38280(18) 0.0172(6) Uani 1 1 d . . . . .
C17 C 0.6201(3) -0.04626(17) 0.40668(19) 0.0209(7) Uani 1 1 d . . . . .
H17 H 0.688188 -0.006030 0.414064 0.025 Uiso 1 1 calc R . . . .
C18 C 0.6532(3) -0.13013(17) 0.41919(19) 0.0195(7) Uani 1 1 d . . . . .
H18 H 0.743057 -0.146850 0.434754 0.023 Uiso 1 1 calc R . . . .
C19 C 0.4413(3) 0.06683(17) 0.36600(19) 0.0209(7) Uani 1 1 d . . . . .
H19 H 0.349438 0.075417 0.343968 0.025 Uiso 1 1 calc R . . . .
C20 C 0.5184(3) 0.13629(17) 0.37846(19) 0.0204(7) Uani 1 1 d . . . . .
H20 H 0.610376 0.129866 0.401951 0.024 Uiso 1 1 calc R . . . .
C21 C 0.4668(3) 0.22050(17) 0.35752(19) 0.0183(7) Uani 1 1 d . . . . .
C22 C 0.5316(3) 0.29546(17) 0.37902(19) 0.0192(7) Uani 1 1 d . . . . .
H22 H 0.621045 0.300064 0.410216 0.023 Uiso 1 1 calc R . . . .
C23 C 0.4478(3) 0.36525(16) 0.34869(19) 0.0185(7) Uani 1 1 d . . . . .
C24 C 0.3221(3) 0.34466(17) 0.3033(2) 0.0224(7) Uani 1 1 d . . . . .
H24 H 0.255319 0.383331 0.278500 0.027 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C11 1.886(3) . ?
S1 C9 1.731(3) . ?
S1 C12 1.712(3) . ?
O1 N1 1.230(3) . ?
O2 N1 1.224(3) . ?
N1 C1 1.464(3) . ?
C1 C2 1.385(4) . ?
C1 C6 1.379(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.405(4) . ?
C4 C5 1.397(4) . ?
C4 C7 1.461(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.333(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.444(4) . ?
C9 C10 1.361(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.407(4) . ?
C11 C12 1.351(4) . ?
C12 H12 0.9300 . ?
Br2 C23 1.883(3) . ?
S2 C21 1.733(3) . ?
S2 C24 1.712(3) . ?
O3 N2 1.220(3) . ?
O4 N2 1.229(3) . ?
N2 C13 1.466(3) . ?
C13 C14 1.377(4) . ?
C13 C18 1.385(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.400(4) . ?
C16 C17 1.410(4) . ?
C16 C19 1.457(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.341(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.444(4) . ?
C21 C22 1.363(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.410(4) . ?
C23 C24 1.349(4) . ?
C24 H24 0.9300 . ?

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
C12 S1 C9 92.25(14) . . ?
O1 N1 C1 118.1(3) . . ?
O2 N1 O1 123.2(2) . . ?
O2 N1 C1 118.7(3) . . ?
C2 C1 N1 119.5(3) . . ?
C6 C1 N1 118.1(3) . . ?
C6 C1 C2 122.4(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C7 123.9(3) . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 C7 117.7(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 H6 120.7 . . ?
C5 C6 C1 118.5(3) . . ?
C5 C6 H6 120.7 . . ?
C4 C7 H7 116.0 . . ?
C8 C7 C4 128.1(3) . . ?
C8 C7 H7 116.0 . . ?
C7 C8 H8 117.7 . . ?
C7 C8 C9 124.5(3) . . ?
C9 C8 H8 117.7 . . ?
C8 C9 S1 121.6(2) . . ?
C10 C9 S1 110.5(2) . . ?
C10 C9 C8 127.9(3) . . ?
C9 C10 H10 123.7 . . ?
C9 C10 C11 112.5(3) . . ?
C11 C10 H10 123.7 . . ?
C10 C11 Br1 123.4(2) . . ?
C12 C11 Br1 122.4(2) . . ?
C12 C11 C10 114.2(3) . . ?
S1 C12 H12 124.7 . . ?
C11 C12 S1 110.6(2) . . ?
C11 C12 H12 124.7 . . ?
C24 S2 C21 92.38(14) . . ?
O3 N2 O4 124.3(3) . . ?
O3 N2 C13 118.2(3) . . ?
O4 N2 C13 117.6(3) . . ?
C14 C13 N2 118.8(3) . . ?
C14 C13 C18 122.1(3) . . ?
C18 C13 N2 119.1(3) . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.7(3) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.3(3) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 118.1(3) . . ?
C15 C16 C19 117.9(3) . . ?
C17 C16 C19 124.0(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 H18 120.5 . . ?
C17 C18 C13 118.9(3) . . ?
C17 C18 H18 120.5 . . ?
C16 C19 H19 116.1 . . ?
C20 C19 C16 127.9(3) . . ?
C20 C19 H19 116.1 . . ?
C19 C20 H20 118.1 . . ?
C19 C20 C21 123.8(3) . . ?
C21 C20 H20 118.1 . . ?
C20 C21 S2 121.2(2) . . ?
C22 C21 S2 110.3(2) . . ?
C22 C21 C20 128.5(3) . . ?
C21 C22 H22 123.8 . . ?
C21 C22 C23 112.5(3) . . ?
C23 C22 H22 123.8 . . ?
C22 C23 Br2 123.5(2) . . ?
C24 C23 Br2 122.3(2) . . ?
C24 C23 C22 114.2(3) . . ?
S2 C24 H24 124.7 . . ?
C23 C24 S2 110.6(2) . . ?
C23 C24 H24 124.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H6 S2 0.93 2.79 3.608(3) 148.0 4_666 yes
C8 H8 O3 0.93 2.52 3.423(4) 165.1 1_565 yes
C14 H14 O2 0.93 2.50 3.273(4) 140.1 3_656 yes
C22 H22 O2 0.93 2.39 3.258(4) 154.8 . yes

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
Br1 C11 C12 S1 -179.16(15) . . . . ?
S1 C9 C10 C11 0.3(3) . . . . ?
O1 N1 C1 C2 -176.5(3) . . . . ?
O1 N1 C1 C6 2.9(4) . . . . ?
O2 N1 C1 C2 3.4(4) . . . . ?
O2 N1 C1 C6 -177.2(2) . . . . ?
N1 C1 C2 C3 179.6(2) . . . . ?
N1 C1 C6 C5 -179.3(2) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C2 C3 C4 C7 -180.0(3) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C3 C4 C7 C8 -7.6(5) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C4 C7 C8 C9 -179.5(3) . . . . ?
C5 C4 C7 C8 171.8(3) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C7 C4 C5 C6 -179.9(3) . . . . ?
C7 C8 C9 S1 -4.1(4) . . . . ?
C7 C8 C9 C10 174.6(3) . . . . ?
C8 C9 C10 C11 -178.5(3) . . . . ?
C9 S1 C12 C11 0.0(2) . . . . ?
C9 C10 C11 Br1 179.0(2) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 S1 0.2(3) . . . . ?
C12 S1 C9 C8 178.7(2) . . . . ?
C12 S1 C9 C10 -0.2(2) . . . . ?
Br2 C23 C24 S2 -178.62(15) . . . . ?
S2 C21 C22 C23 1.2(3) . . . . ?
O3 N2 C13 C14 -166.2(3) . . . . ?
O3 N2 C13 C18 13.8(4) . . . . ?
O4 N2 C13 C14 13.5(4) . . . . ?
O4 N2 C13 C18 -166.6(3) . . . . ?
N2 C13 C14 C15 -179.9(2) . . . . ?
N2 C13 C18 C17 179.8(2) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C14 C13 C18 C17 -0.3(4) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
C14 C15 C16 C19 178.2(3) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
C15 C16 C19 C20 174.0(3) . . . . ?
C16 C17 C18 C13 -0.2(4) . . . . ?
C16 C19 C20 C21 178.4(3) . . . . ?
C17 C16 C19 C20 -7.0(5) . . . . ?
C18 C13 C14 C15 0.1(4) . . . . ?
C19 C16 C17 C18 -178.3(3) . . . . ?
C19 C20 C21 S2 -9.9(4) . . . . ?
C19 C20 C21 C22 170.1(3) . . . . ?
C20 C21 C22 C23 -178.8(3) . . . . ?
C21 S2 C24 C23 0.0(2) . . . . ?
C21 C22 C23 Br2 178.0(2) . . . . ?
C21 C22 C23 C24 -1.2(4) . . . . ?
C22 C23 C24 S2 0.6(3) . . . . ?
C24 S2 C21 C20 179.3(2) . . . . ?
C24 S2 C21 C22 -0.7(2) . . . . ?


_ins_header                      
;
TITL ek1902_a2 in P2(1)/c 
REM P2(1)/c (#14 in standard setting)
CELL 0.71073  10.145817  15.864922  14.814098  90.0000 102.2605  90.0000
ZERR   10.00   0.000523   0.000593   0.000703   0.0000   0.0047   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2 
SFAC C H N O
UNIT 110.00 100.00 10.00 10.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.541
_oxdiff_exptl_absorpt_empirical_full_min 0.719
####################################################################### 
# 
# 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_compound_4_Pcell
_database_code_depnum_ccdc_archive 'CCDC 2058519'
loop_
_audit_author_name
_audit_author_address
'Jari Konu'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H28 Cl2 N2 O8'
_chemical_formula_sum            'C32 H28 Cl2 N2 O8'
_chemical_formula_weight         639.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H14 O4 N1 Cl1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.5166(2)
_cell_length_b                   12.8669(2)
_cell_length_c                   19.7897(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.4671(16)
_cell_angle_gamma                90
_cell_volume                     2932.40(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5649
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.3170
_cell_measurement_theta_min      4.1010
_shelx_estimated_absorpt_T_max   0.886
_shelx_estimated_absorpt_T_min   0.576
_exptl_absorpt_coefficient_mu    2.476
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12694
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.512
_diffrn_reflns_theta_min         4.098
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  27.00   1.00    3.00    --  -41.65  37.00-150.00   86
  2  ω    -96.00  -4.00   1.00    3.00    --  -41.65 125.00 -90.00   92
  3  ω      4.00  77.00   1.00    3.00    --   41.65 -99.00 120.00   73
  4  ω     88.00 177.00   1.00   10.00    --  112.00  45.00 -30.00   89
  5  ω     29.00 102.00   1.00   10.00    --  112.00 -94.00  90.00   73
  6  ω     55.00 138.00   1.00   10.00    --  112.00 -45.00-120.00   83
  7  ω    101.00 174.00   1.00   10.00    --  112.00  15.00-120.00   73
  8  ω     63.00  90.00   1.00   10.00    --  112.00  15.00-120.00   27
  9  ω     40.00 138.00   1.00   10.00    --  112.00 -45.00 150.00   98
 10  ω     65.00 103.00   1.00   10.00    --  112.00 -94.00 -30.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0739749000
_diffrn_orient_matrix_UB_12      -0.0549485000
_diffrn_orient_matrix_UB_13      0.0537253000
_diffrn_orient_matrix_UB_21      -0.0551511000
_diffrn_orient_matrix_UB_22      -0.0687214000
_diffrn_orient_matrix_UB_23      -0.0553669000
_diffrn_orient_matrix_UB_31      0.0968187000
_diffrn_orient_matrix_UB_32      -0.0812427000
_diffrn_orient_matrix_UB_33      0.0104033000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5148
_reflns_number_total             6015
_reflns_odcompleteness_completeness 98.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6015
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²+0.7892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0958
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C23(H23), C24(H24)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C18(H18), C19(H19),
 C21(H21), C22(H22), C26(H26), C27(H27)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.59954(3) 0.80138(3) 0.19208(2) 0.02542(10) Uani 1 1 d . . . . .
Cl2 Cl 0.93306(4) 1.20473(3) -0.02003(2) 0.03048(10) Uani 1 1 d . . . . .
O1 O 0.35016(11) 1.29662(10) -0.05575(6) 0.0333(3) Uani 1 1 d . . . . .
O2 O 0.46720(14) 1.42761(12) -0.05711(8) 0.0504(4) Uani 1 1 d . . . . .
O3 O 0.54306(10) 0.80664(9) 0.33494(6) 0.0253(2) Uani 1 1 d . . . . .
O4 O 0.59060(10) 0.95979(9) 0.42319(5) 0.0269(2) Uani 1 1 d . . . . .
O5 O 1.20819(14) 1.00937(12) 0.37937(8) 0.0482(4) Uani 1 1 d . . . . .
O6 O 1.15425(12) 0.85139(13) 0.39740(7) 0.0429(3) Uani 1 1 d . . . . .
O7 O 0.82788(11) 1.16414(11) -0.15200(6) 0.0327(3) Uani 1 1 d . . . . .
O8 O 0.70120(12) 1.00022(11) -0.18908(6) 0.0365(3) Uani 1 1 d . . . . .
N1 N 0.44274(13) 1.33858(11) -0.04111(7) 0.0290(3) Uani 1 1 d . . . . .
N2 N 1.14886(13) 0.93330(13) 0.36570(7) 0.0332(3) Uani 1 1 d . . . . .
C1 C 0.52783(14) 1.27867(12) -0.00183(8) 0.0242(3) Uani 1 1 d . . . . .
C2 C 0.51414(15) 1.17249(13) 0.00100(8) 0.0268(3) Uani 1 1 d . . . . .
H2 H 0.454056 1.140065 -0.022561 0.032 Uiso 1 1 calc R . . . .
C3 C 0.59141(15) 1.11503(12) 0.03952(8) 0.0271(3) Uani 1 1 d . . . . .
H3 H 0.583103 1.043204 0.041483 0.032 Uiso 1 1 calc R . . . .
C4 C 0.68142(13) 1.16227(12) 0.07545(7) 0.0207(3) Uani 1 1 d . . . . .
C5 C 0.69277(15) 1.26983(13) 0.07073(9) 0.0292(3) Uani 1 1 d . . . . .
H5 H 0.752703 1.302746 0.094127 0.035 Uiso 1 1 calc R . . . .
C6 C 0.61677(16) 1.32889(13) 0.03197(9) 0.0330(4) Uani 1 1 d . . . . .
H6 H 0.625516 1.400572 0.028825 0.040 Uiso 1 1 calc R . . . .
C7 C 0.76753(13) 1.10043(12) 0.11685(7) 0.0204(3) Uani 1 1 d . . . . .
H7 H 0.801294 1.145071 0.151993 0.025 Uiso 1 1 calc R . . . .
C8 C 0.72733(13) 0.99721(11) 0.14885(7) 0.0197(3) Uani 1 1 d . . . . .
H8 H 0.668854 0.965307 0.119173 0.024 Uiso 1 1 calc R . . . .
C9 C 0.68422(13) 0.99396(12) 0.22032(7) 0.0193(3) Uani 1 1 d . . . . .
C10 C 0.62683(13) 0.90628(11) 0.24525(7) 0.0195(3) Uani 1 1 d . . . . .
C11 C 0.59295(13) 0.89676(12) 0.31234(7) 0.0207(3) Uani 1 1 d . . . . .
C12 C 0.61952(13) 0.97798(12) 0.35768(7) 0.0221(3) Uani 1 1 d . . . . .
C13 C 0.67431(14) 1.06640(13) 0.33408(8) 0.0252(3) Uani 1 1 d . . . . .
H13 H 0.690278 1.121089 0.363449 0.030 Uiso 1 1 calc R . . . .
C14 C 0.70565(14) 1.07359(12) 0.26622(8) 0.0233(3) Uani 1 1 d . . . . .
H14 H 0.742105 1.133712 0.251229 0.028 Uiso 1 1 calc R . . . .
C15 C 0.63472(16) 1.03173(16) 0.47246(8) 0.0333(4) Uani 1 1 d . . . . .
H15A H 0.597031 1.097728 0.466742 0.050 Uiso 1 1 calc GR . . . .
H15B H 0.716879 1.039961 0.466621 0.050 Uiso 1 1 calc GR . . . .
H15C H 0.619782 1.005638 0.516999 0.050 Uiso 1 1 calc GR . . . .
C16 C 0.42158(16) 0.81622(15) 0.34904(10) 0.0340(4) Uani 1 1 d . . . . .
H16A H 0.379818 0.830037 0.307836 0.051 Uiso 1 1 calc GR . . . .
H16B H 0.409759 0.872357 0.380190 0.051 Uiso 1 1 calc GR . . . .
H16C H 0.393855 0.752668 0.368549 0.051 Uiso 1 1 calc GR . . . .
C17 C 1.06873(15) 0.93926(14) 0.30751(8) 0.0274(3) Uani 1 1 d . . . . .
C18 C 1.00463(15) 0.85275(14) 0.28972(8) 0.0288(3) Uani 1 1 d . . . . .
H18 H 1.007701 0.792616 0.315741 0.035 Uiso 1 1 calc R . . . .
C19 C 0.93543(14) 0.85764(13) 0.23204(8) 0.0258(3) Uani 1 1 d . . . . .
H19 H 0.892054 0.799869 0.219182 0.031 Uiso 1 1 calc R . . . .
C20 C 0.92996(14) 0.94799(12) 0.19303(7) 0.0222(3) Uani 1 1 d . . . . .
C21 C 0.99271(14) 1.03465(13) 0.21418(8) 0.0263(3) Uani 1 1 d . . . . .
H21 H 0.987472 1.096054 0.189553 0.032 Uiso 1 1 calc R . . . .
C22 C 1.06293(15) 1.03095(14) 0.27140(8) 0.0285(3) Uani 1 1 d . . . . .
H22 H 1.105173 1.088933 0.285133 0.034 Uiso 1 1 calc R . . . .
C23 C 0.85009(13) 0.94848(12) 0.13241(7) 0.0214(3) Uani 1 1 d . . . . .
H23 H 0.843925 0.880058 0.110929 0.026 Uiso 1 1 calc R . . . .
C24 C 0.86869(13) 1.03718(12) 0.08048(7) 0.0215(3) Uani 1 1 d . . . . .
H24 H 0.944646 1.070714 0.085691 0.026 Uiso 1 1 calc R . . . .
C25 C 0.83868(13) 1.01493(12) 0.00763(7) 0.0221(3) Uani 1 1 d . . . . .
C26 C 0.78154(14) 0.92618(13) -0.01429(8) 0.0252(3) Uani 1 1 d . . . . .
H26 H 0.772828 0.871159 0.015716 0.030 Uiso 1 1 calc R . . . .
C27 C 0.73648(15) 0.91619(14) -0.07981(8) 0.0277(3) Uani 1 1 d . . . . .
H27 H 0.699109 0.855258 -0.092859 0.033 Uiso 1 1 calc R . . . .
C28 C 0.74778(15) 0.99747(15) -0.12517(8) 0.0287(3) Uani 1 1 d . . . . .
C29 C 0.81069(14) 1.08615(14) -0.10619(8) 0.0273(3) Uani 1 1 d . . . . .
C30 C 0.85615(14) 1.09291(13) -0.04100(8) 0.0239(3) Uani 1 1 d . . . . .
C31 C 0.73843(19) 1.24178(18) -0.15003(11) 0.0461(5) Uani 1 1 d . . . . .
H31A H 0.756569 1.296542 -0.181157 0.069 Uiso 1 1 calc GR . . . .
H31B H 0.733536 1.269727 -0.105164 0.069 Uiso 1 1 calc GR . . . .
H31C H 0.665389 1.210998 -0.162448 0.069 Uiso 1 1 calc GR . . . .
C32 C 0.62662(18) 0.91606(18) -0.20713(9) 0.0418(5) Uani 1 1 d . . . . .
H32A H 0.595909 0.927255 -0.251785 0.063 Uiso 1 1 calc GR . . . .
H32B H 0.563912 0.911986 -0.175582 0.063 Uiso 1 1 calc GR . . . .
H32C H 0.669840 0.852266 -0.206189 0.063 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C10 1.7386(15) . ?
Cl2 C30 1.7380(17) . ?
O1 N1 1.228(2) . ?
O2 N1 1.222(2) . ?
O3 C11 1.3707(19) . ?
O3 C16 1.434(2) . ?
O4 C12 1.3613(18) . ?
O4 C15 1.434(2) . ?
O5 N2 1.223(2) . ?
O6 N2 1.228(2) . ?
O7 C29 1.368(2) . ?
O7 C31 1.436(2) . ?
O8 C28 1.3702(19) . ?
O8 C32 1.426(3) . ?
N1 C1 1.465(2) . ?
N2 C17 1.472(2) . ?
C1 C2 1.377(2) . ?
C1 C6 1.379(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(2) . ?
C4 C5 1.393(2) . ?
C4 C7 1.508(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.544(2) . ?
C7 C24 1.597(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.5035(19) . ?
C8 C23 1.583(2) . ?
C9 C10 1.399(2) . ?
C9 C14 1.390(2) . ?
C10 C11 1.392(2) . ?
C11 C12 1.409(2) . ?
C12 C13 1.384(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.396(2) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.380(3) . ?
C17 C22 1.381(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.397(2) . ?
C20 C21 1.391(2) . ?
C20 C23 1.506(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.387(2) . ?
C22 H22 0.9300 . ?
C23 H23 0.9800 . ?
C23 C24 1.552(2) . ?
C24 H24 0.9800 . ?
C24 C25 1.507(2) . ?
C25 C26 1.386(2) . ?
C25 C30 1.406(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.399(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.385(2) . ?
C28 C29 1.401(3) . ?
C29 C30 1.391(2) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O3 C16 113.76(13) . . ?
C12 O4 C15 116.64(13) . . ?
C29 O7 C31 112.63(13) . . ?
C28 O8 C32 116.24(15) . . ?
O1 N1 C1 118.02(14) . . ?
O2 N1 O1 123.55(15) . . ?
O2 N1 C1 118.43(15) . . ?
O5 N2 O6 123.24(15) . . ?
O5 N2 C17 118.49(15) . . ?
O6 N2 C17 118.25(16) . . ?
C2 C1 N1 117.87(15) . . ?
C2 C1 C6 122.01(15) . . ?
C6 C1 N1 120.11(15) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.69(15) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.46(15) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 117.99(14) . . ?
C3 C4 C7 122.06(14) . . ?
C5 C4 C7 119.92(14) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.50(16) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 118.34(16) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C4 C7 H7 109.4 . . ?
C4 C7 C8 118.59(13) . . ?
C4 C7 C24 120.18(12) . . ?
C8 C7 H7 109.4 . . ?
C8 C7 C24 88.21(11) . . ?
C24 C7 H7 109.4 . . ?
C7 C8 H8 108.8 . . ?
C7 C8 C23 89.15(11) . . ?
C9 C8 C7 120.81(12) . . ?
C9 C8 H8 108.8 . . ?
C9 C8 C23 118.99(12) . . ?
C23 C8 H8 108.8 . . ?
C10 C9 C8 120.98(13) . . ?
C14 C9 C8 122.42(14) . . ?
C14 C9 C10 116.46(13) . . ?
C9 C10 Cl1 119.74(11) . . ?
C11 C10 Cl1 117.27(12) . . ?
C11 C10 C9 122.96(13) . . ?
O3 C11 C10 120.46(13) . . ?
O3 C11 C12 120.60(13) . . ?
C10 C11 C12 118.74(14) . . ?
O4 C12 C11 115.17(14) . . ?
O4 C12 C13 125.34(14) . . ?
C13 C12 C11 119.47(14) . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.07(14) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C13 122.26(15) . . ?
C9 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 N2 119.23(15) . . ?
C18 C17 C22 122.26(15) . . ?
C22 C17 N2 118.48(16) . . ?
C17 C18 H18 120.8 . . ?
C17 C18 C19 118.40(15) . . ?
C19 C18 H18 120.8 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.02(16) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C23 117.94(14) . . ?
C21 C20 C19 118.67(14) . . ?
C21 C20 C23 123.28(14) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 121.07(15) . . ?
C22 C21 H21 119.5 . . ?
C17 C22 C21 118.51(16) . . ?
C17 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
C8 C23 H23 112.5 . . ?
C20 C23 C8 112.26(12) . . ?
C20 C23 H23 112.5 . . ?
C20 C23 C24 116.36(13) . . ?
C24 C23 C8 88.46(11) . . ?
C24 C23 H23 112.5 . . ?
C7 C24 H24 112.5 . . ?
C23 C24 C7 88.34(11) . . ?
C23 C24 H24 112.5 . . ?
C25 C24 C7 111.43(12) . . ?
C25 C24 C23 117.51(13) . . ?
C25 C24 H24 112.5 . . ?
C26 C25 C24 124.10(14) . . ?
C26 C25 C30 116.36(14) . . ?
C30 C25 C24 119.09(14) . . ?
C25 C26 H26 118.7 . . ?
C25 C26 C27 122.52(15) . . ?
C27 C26 H26 118.7 . . ?
C26 C27 H27 120.2 . . ?
C28 C27 C26 119.70(16) . . ?
C28 C27 H27 120.2 . . ?
O8 C28 C27 125.43(17) . . ?
O8 C28 C29 115.09(15) . . ?
C27 C28 C29 119.48(15) . . ?
O7 C29 C28 119.81(15) . . ?
O7 C29 C30 120.89(16) . . ?
C30 C29 C28 119.30(15) . . ?
C25 C30 Cl2 120.19(12) . . ?
C29 C30 Cl2 117.42(13) . . ?
C29 C30 C25 122.37(15) . . ?
O7 C31 H31A 109.5 . . ?
O7 C31 H31B 109.5 . . ?
O7 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O8 C32 H32A 109.5 . . ?
O8 C32 H32B 109.5 . . ?
O8 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H6 O2 0.93 2.52 3.318(2) 144.0 3_685 yes

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
Cl1 C10 C11 O3 1.68(19) . . . . ?
Cl1 C10 C11 C12 176.53(11) . . . . ?
O1 N1 C1 C2 17.1(2) . . . . ?
O1 N1 C1 C6 -161.63(16) . . . . ?
O2 N1 C1 C2 -163.43(17) . . . . ?
O2 N1 C1 C6 17.9(2) . . . . ?
O3 C11 C12 O4 -0.9(2) . . . . ?
O3 C11 C12 C13 177.30(14) . . . . ?
O4 C12 C13 C14 176.26(15) . . . . ?
O5 N2 C17 C18 177.38(17) . . . . ?
O5 N2 C17 C22 -0.8(2) . . . . ?
O6 N2 C17 C18 -1.3(2) . . . . ?
O6 N2 C17 C22 -179.55(16) . . . . ?
O7 C29 C30 Cl2 1.0(2) . . . . ?
O7 C29 C30 C25 179.03(14) . . . . ?
O8 C28 C29 O7 -4.1(2) . . . . ?
O8 C28 C29 C30 176.67(14) . . . . ?
N1 C1 C2 C3 -178.00(15) . . . . ?
N1 C1 C6 C5 177.48(16) . . . . ?
N2 C17 C18 C19 -175.73(15) . . . . ?
N2 C17 C22 C21 176.19(15) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C2 C3 C4 C7 -179.04(15) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C3 C4 C7 C8 -30.0(2) . . . . ?
C3 C4 C7 C24 76.05(19) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C7 C8 C9 -94.56(16) . . . . ?
C4 C7 C8 C23 141.69(13) . . . . ?
C4 C7 C24 C23 -140.69(14) . . . . ?
C4 C7 C24 C25 -21.68(19) . . . . ?
C5 C4 C7 C8 151.97(15) . . . . ?
C5 C4 C7 C24 -102.01(17) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C7 C4 C5 C6 178.58(16) . . . . ?
C7 C8 C9 C10 167.34(13) . . . . ?
C7 C8 C9 C14 -17.1(2) . . . . ?
C7 C8 C23 C20 99.50(13) . . . . ?
C7 C8 C23 C24 -18.46(11) . . . . ?
C7 C24 C25 C26 -90.73(18) . . . . ?
C7 C24 C25 C30 81.25(17) . . . . ?
C8 C7 C24 C23 -18.30(11) . . . . ?
C8 C7 C24 C25 100.72(13) . . . . ?
C8 C9 C10 Cl1 -2.61(19) . . . . ?
C8 C9 C10 C11 175.19(14) . . . . ?
C8 C9 C14 C13 -174.31(15) . . . . ?
C8 C23 C24 C7 17.83(10) . . . . ?
C8 C23 C24 C25 -95.56(14) . . . . ?
C9 C8 C23 C20 -25.77(18) . . . . ?
C9 C8 C23 C24 -143.73(13) . . . . ?
C9 C10 C11 O3 -176.17(14) . . . . ?
C9 C10 C11 C12 -1.3(2) . . . . ?
C10 C9 C14 C13 1.4(2) . . . . ?
C10 C11 C12 O4 -175.72(13) . . . . ?
C10 C11 C12 C13 2.5(2) . . . . ?
C11 C12 C13 C14 -1.7(2) . . . . ?
C12 C13 C14 C9 -0.3(3) . . . . ?
C14 C9 C10 Cl1 -178.38(11) . . . . ?
C14 C9 C10 C11 -0.6(2) . . . . ?
C15 O4 C12 C11 169.11(14) . . . . ?
C15 O4 C12 C13 -8.9(2) . . . . ?
C16 O3 C11 C10 -108.88(16) . . . . ?
C16 O3 C11 C12 76.37(18) . . . . ?
C17 C18 C19 C20 -0.4(2) . . . . ?
C18 C17 C22 C21 -2.0(3) . . . . ?
C18 C19 C20 C21 -1.9(2) . . . . ?
C18 C19 C20 C23 -178.11(15) . . . . ?
C19 C20 C21 C22 2.4(2) . . . . ?
C19 C20 C23 C8 95.26(16) . . . . ?
C19 C20 C23 C24 -164.92(14) . . . . ?
C20 C21 C22 C17 -0.5(3) . . . . ?
C20 C23 C24 C7 -96.35(14) . . . . ?
C20 C23 C24 C25 150.26(13) . . . . ?
C21 C20 C23 C8 -80.73(18) . . . . ?
C21 C20 C23 C24 19.1(2) . . . . ?
C22 C17 C18 C19 2.4(3) . . . . ?
C23 C8 C9 C10 -84.56(18) . . . . ?
C23 C8 C9 C14 90.96(18) . . . . ?
C23 C20 C21 C22 178.36(15) . . . . ?
C23 C24 C25 C26 9.0(2) . . . . ?
C23 C24 C25 C30 -179.00(14) . . . . ?
C24 C7 C8 C9 141.67(13) . . . . ?
C24 C7 C8 C23 17.92(10) . . . . ?
C24 C25 C26 C27 168.13(15) . . . . ?
C24 C25 C30 Cl2 10.5(2) . . . . ?
C24 C25 C30 C29 -167.41(14) . . . . ?
C25 C26 C27 C28 -0.4(3) . . . . ?
C26 C25 C30 Cl2 -176.86(12) . . . . ?
C26 C25 C30 C29 5.2(2) . . . . ?
C26 C27 C28 O8 -175.53(15) . . . . ?
C26 C27 C28 C29 4.0(2) . . . . ?
C27 C28 C29 O7 176.25(15) . . . . ?
C27 C28 C29 C30 -2.9(2) . . . . ?
C28 C29 C30 Cl2 -179.81(12) . . . . ?
C28 C29 C30 C25 -1.8(2) . . . . ?
C30 C25 C26 C27 -4.1(2) . . . . ?
C31 O7 C29 C28 90.9(2) . . . . ?
C31 O7 C29 C30 -89.9(2) . . . . ?
C32 O8 C28 C27 6.0(2) . . . . ?
C32 O8 C28 C29 -173.57(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.406
_oxdiff_exptl_absorpt_empirical_full_min 0.798
####################################################################### 
# 
# 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_compound_4_Ccell
_database_code_depnum_ccdc_archive 'CCDC 2058518'
loop_
_audit_author_name
_audit_author_address
'Jari Konu'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_audit_creation_date             2021-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H28 Cl2 N2 O8'
_chemical_formula_sum            'C32 H28 Cl2 N2 O8'
_chemical_formula_weight         639.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H14 N1 O4 Cl1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.6720(3)
_cell_length_b                   10.3954(2)
_cell_length_c                   18.9716(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.264(2)
_cell_angle_gamma                90
_cell_volume                     2888.88(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3254
_cell_measurement_temperature    121(1)
_cell_measurement_theta_max      75.4050
_cell_measurement_theta_min      4.6490
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.770
_exptl_absorpt_coefficient_mu    2.514
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 0 5 0.0246
4 -1 -5 0.0140
-4 1 5 0.0100
-2 -5 0 0.0480
2 5 0 0.0480
-3 0 -5 0.0406

_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.024
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.0000 0.0001 5.0003 0.1126 -0.5164 0.0086
4.0002 -1.0000 -5.0001 0.5553 0.1785 -0.0710
-4.0002 1.0000 5.0001 -0.5553 -0.1785 0.0710
-1.9999 -5.0000 0.0001 -0.0837 0.1069 -0.7579
1.9999 5.0000 -0.0001 0.0837 -0.1069 0.7579
-3.0000 -0.0001 -5.0003 -0.1126 0.5164 -0.0086

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4692
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.760
_diffrn_reflns_theta_min         4.669
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      121(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -17.00   1.00   15.00    --  -41.65 -37.00  90.00   98
  2  ω   -114.00 -15.00   1.00   15.00    --  -41.65 -57.00-150.00   99
  3  ω    100.00 178.00   1.00   75.00    --  112.00  30.00 150.00   78
  4  ω     42.00 115.00   1.00   75.00    --  112.00-111.00-120.00   73
  5  ω     36.00 140.00   1.00   75.00    --  112.00 -30.00 -30.00  104
  6  ω     42.00 141.00   1.00   75.00    --  112.00 -61.00  60.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0925206000
_diffrn_orient_matrix_UB_12      -0.0202670000
_diffrn_orient_matrix_UB_13      -0.0329874000
_diffrn_orient_matrix_UB_21      -0.0485496000
_diffrn_orient_matrix_UB_22      -0.0019641000
_diffrn_orient_matrix_UB_23      -0.0741477000
_diffrn_orient_matrix_UB_31      0.0120484000
_diffrn_orient_matrix_UB_32      0.1467631000
_diffrn_orient_matrix_UB_33      -0.0055121000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2707
_reflns_number_total             2910
_reflns_odcompleteness_completeness 99.10
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2910
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+2.3576P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0981
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-N1 \\sim O1A-N1A
 with sigma of 0.02
 N1-C1 \\sim N1A-C1
 with sigma of 0.02
 N1-O2 \\sim N1A-O2A
 with sigma of 0.02
 C1-O2 \\sim C1-O2A
 with sigma of 0.04
 O1-O2 \\sim O1A-O2A
 with sigma of 0.04
 O1-C1 \\sim O1A-C1
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(O2A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 O1, N1, C1, O2, O1A, N1A, O2A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: O1(0.566) O2(0.566) N1(0.566) O1A(0.434) O2A(0.434) N1A(0.434)
6.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14)
6.c Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C16(H16a,H16b,H16c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.30831(2) 0.39056(3) 0.46516(2) 0.02651(12) Uani 1 1 d . . . . .
O4 O 0.44582(8) 0.26560(10) 0.55853(6) 0.0294(3) Uani 1 1 d . . . . .
O5 O 0.55540(8) 0.37911(11) 0.65931(6) 0.0300(3) Uani 1 1 d . . . . .
C1 C 0.35336(11) 1.03812(16) 0.30609(8) 0.0292(3) Uani 1 1 d D U . . .
C2 C 0.30694(10) 0.92218(15) 0.29913(8) 0.0246(3) Uani 1 1 d . . . . .
H2 H 0.287442 0.890824 0.254904 0.030 Uiso 1 1 calc R . . . .
C3 C 0.29053(10) 0.85464(14) 0.35982(7) 0.0239(3) Uani 1 1 d . . . . .
H3 H 0.257739 0.778124 0.356286 0.029 Uiso 1 1 calc R . . . .
C4 C 0.32204(10) 0.89862(13) 0.42635(7) 0.0208(3) Uani 1 1 d . . . . .
C5 C 0.36910(11) 1.01520(15) 0.43085(8) 0.0292(3) Uani 1 1 d . . . . .
H5 H 0.390969 1.045328 0.474769 0.035 Uiso 1 1 calc R . . . .
C6 C 0.38381(13) 1.08683(17) 0.37100(9) 0.0368(4) Uani 1 1 d . . . . .
H6 H 0.413473 1.165836 0.374409 0.044 Uiso 1 1 calc R . . . .
C7 C 0.30116(9) 0.82741(13) 0.49252(7) 0.0204(3) Uani 1 1 d . . . . .
H7 H 0.339540 0.858593 0.532916 0.024 Uiso 1 1 calc R . . . .
C8 C 0.30296(10) 0.67792(13) 0.48887(7) 0.0207(3) Uani 1 1 d . . . . .
H8 H 0.308034 0.651204 0.439714 0.025 Uiso 1 1 calc R . . . .
C9 C 0.37132(10) 0.60407(13) 0.53530(7) 0.0207(3) Uani 1 1 d . . . . .
C10 C 0.37842(10) 0.46964(14) 0.52812(7) 0.0216(3) Uani 1 1 d . . . . .
C11 C 0.43931(10) 0.39581(14) 0.56971(8) 0.0235(3) Uani 1 1 d . . . . .
C12 C 0.49636(10) 0.45713(14) 0.62106(7) 0.0236(3) Uani 1 1 d . . . . .
C13 C 0.48951(10) 0.58902(15) 0.63011(8) 0.0246(3) Uani 1 1 d . . . . .
H13 H 0.526140 0.630100 0.664837 0.030 Uiso 1 1 calc R . . . .
C14 C 0.42797(10) 0.66007(14) 0.58736(8) 0.0231(3) Uani 1 1 d . . . . .
H14 H 0.424810 0.748546 0.594046 0.028 Uiso 1 1 calc R . . . .
C15 C 0.41549(14) 0.18865(16) 0.61509(9) 0.0369(4) Uani 1 1 d . . . . .
H15A H 0.417892 0.099417 0.602282 0.055 Uiso 1 1 calc GR . . . .
H15B H 0.353877 0.211511 0.624213 0.055 Uiso 1 1 calc GR . . . .
H15C H 0.454349 0.203327 0.656745 0.055 Uiso 1 1 calc GR . . . .
C16 C 0.61820(11) 0.43987(16) 0.70863(8) 0.0305(3) Uani 1 1 d . . . . .
H16A H 0.657343 0.496174 0.683989 0.046 Uiso 1 1 calc GR . . . .
H16B H 0.654408 0.375631 0.733461 0.046 Uiso 1 1 calc GR . . . .
H16C H 0.585202 0.488798 0.741716 0.046 Uiso 1 1 calc GR . . . .
O1 O 0.3543(12) 1.0709(14) 0.1858(5) 0.038(3) Uani 0.566 1 d D U P A 1
O2 O 0.3695(2) 1.2393(2) 0.25226(12) 0.0388(5) Uani 0.566 1 d D U P A 1
N1 N 0.3585(4) 1.1232(4) 0.2443(2) 0.0272(10) Uani 0.566 1 d D U P A 1
O1A O 0.3416(15) 1.0620(16) 0.1836(6) 0.0295(14) Uani 0.434 1 d D U P A 2
O2A O 0.4324(4) 1.1900(4) 0.24455(18) 0.0678(13) Uani 0.434 1 d D U P A 2
N1A N 0.3800(5) 1.0981(5) 0.2392(3) 0.0322(15) Uani 0.434 1 d D U P A 2


_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 C10 1.7381(14) . ?
O4 C11 1.3743(18) . ?
O4 C15 1.429(2) . ?
O5 C12 1.3651(18) . ?
O5 C16 1.4231(19) . ?
C1 C2 1.387(2) . ?
C1 C6 1.382(2) . ?
C1 N1 1.473(5) . ?
C1 N1A 1.486(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.396(2) . ?
C4 C5 1.395(2) . ?
C4 C7 1.5039(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.5884(19) 7_566 ?
C7 C8 1.5558(18) . ?
C8 H8 0.9800 . ?
C8 C9 1.5068(19) . ?
C9 C10 1.4085(19) . ?
C9 C14 1.383(2) . ?
C10 C11 1.389(2) . ?
C11 C12 1.401(2) . ?
C12 C13 1.386(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.391(2) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O1 N1 1.235(8) . ?
O2 N1 1.225(5) . ?
O1A N1A 1.226(10) . ?
O2A N1A 1.226(7) . ?

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 O4 C15 114.08(12) . . ?
C12 O5 C16 116.96(12) . . ?
C2 C1 N1 119.6(2) . . ?
C2 C1 N1A 115.8(3) . . ?
C6 C1 C2 122.36(14) . . ?
C6 C1 N1 117.4(2) . . ?
C6 C1 N1A 121.3(3) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 118.06(14) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.50(14) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C7 121.38(13) . . ?
C5 C4 C3 118.50(13) . . ?
C5 C4 C7 120.01(13) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.10(14) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 118.42(15) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C4 C7 H7 110.8 . . ?
C4 C7 C8 116.55(11) . 7_566 ?
C4 C7 C8 116.73(12) . . ?
C8 C7 H7 110.8 . . ?
C8 C7 H7 110.8 7_566 . ?
C8 C7 C8 89.66(11) . 7_566 ?
C7 C8 C7 90.34(11) . 7_566 ?
C7 C8 H8 109.1 7_566 . ?
C7 C8 H8 109.1 . . ?
C9 C8 C7 117.97(11) . 7_566 ?
C9 C8 C7 119.69(12) . . ?
C9 C8 H8 109.1 . . ?
C10 C9 C8 119.96(12) . . ?
C14 C9 C8 123.79(13) . . ?
C14 C9 C10 116.23(13) . . ?
C9 C10 Cl1 119.44(11) . . ?
C11 C10 Cl1 117.74(11) . . ?
C11 C10 C9 122.82(13) . . ?
O4 C11 C10 120.31(13) . . ?
O4 C11 C12 120.76(13) . . ?
C10 C11 C12 118.88(13) . . ?
O5 C12 C11 115.80(13) . . ?
O5 C12 C13 124.76(14) . . ?
C13 C12 C11 119.44(13) . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.14(14) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 122.47(14) . . ?
C9 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 N1 C1 116.6(7) . . ?
O2 N1 C1 120.4(4) . . ?
O2 N1 O1 122.9(8) . . ?
O1A N1A C1 118.4(10) . . ?
O1A N1A O2A 124.4(9) . . ?
O2A N1A C1 116.8(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C13 H13 O2 0.93 2.53 3.453(3) 173.1 5_676 yes
C13 H13 O2A 0.93 2.59 3.455(4) 155.0 5_676 yes

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
Cl1 C10 C11 O4 2.85(19) . . . . ?
Cl1 C10 C11 C12 -179.75(11) . . . . ?
O4 C11 C12 O5 -1.7(2) . . . . ?
O4 C11 C12 C13 178.65(13) . . . . ?
O5 C12 C13 C14 178.87(14) . . . . ?
C1 C2 C3 C4 -2.1(2) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
C2 C1 N1 O1 -27.7(11) . . . . ?
C2 C1 N1 O2 154.7(4) . . . . ?
C2 C1 N1A O1A 17.8(13) . . . . ?
C2 C1 N1A O2A -169.6(5) . . . . ?
C2 C3 C4 C5 1.6(2) . . . . ?
C2 C3 C4 C7 177.75(14) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C3 C4 C7 C8 -65.53(18) . . . 7_566 ?
C3 C4 C7 C8 38.60(19) . . . . ?
C4 C5 C6 C1 -2.1(3) . . . . ?
C4 C7 C8 C7 -119.82(14) . . . 7_566 ?
C4 C7 C8 C9 117.27(14) . . . . ?
C5 C4 C7 C8 -145.31(14) . . . . ?
C5 C4 C7 C8 110.57(16) . . . 7_566 ?
C6 C1 C2 C3 0.5(3) . . . . ?
C6 C1 N1 O1 161.7(10) . . . . ?
C6 C1 N1 O2 -15.9(6) . . . . ?
C6 C1 N1A O1A -170.4(12) . . . . ?
C6 C1 N1A O2A 2.2(8) . . . . ?
C7 C4 C5 C6 -175.64(16) . . . . ?
C7 C8 C9 C10 -174.74(13) . . . . ?
C7 C8 C9 C10 77.17(17) 7_566 . . . ?
C7 C8 C9 C14 7.0(2) . . . . ?
C7 C8 C9 C14 -101.14(16) 7_566 . . . ?
C8 C7 C8 C7 0.003(0) 7_566 . . 7_566 ?
C8 C7 C8 C9 -122.90(14) 7_566 . . . ?
C8 C9 C10 Cl1 0.36(18) . . . . ?
C8 C9 C10 C11 -179.33(13) . . . . ?
C8 C9 C14 C13 179.03(13) . . . . ?
C9 C10 C11 O4 -177.44(13) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C10 C9 C14 C13 0.7(2) . . . . ?
C10 C11 C12 O5 -179.08(13) . . . . ?
C10 C11 C12 C13 1.3(2) . . . . ?
C11 C12 C13 C14 -1.5(2) . . . . ?
C12 C13 C14 C9 0.5(2) . . . . ?
C14 C9 C10 Cl1 178.79(10) . . . . ?
C14 C9 C10 C11 -0.9(2) . . . . ?
C15 O4 C11 C10 -113.32(16) . . . . ?
C15 O4 C11 C12 69.34(18) . . . . ?
C16 O5 C12 C11 176.02(13) . . . . ?
C16 O5 C12 C13 -4.4(2) . . . . ?
N1 C1 C2 C3 -169.6(3) . . . . ?
N1 C1 C6 C5 171.9(3) . . . . ?
N1A C1 C2 C3 172.2(3) . . . . ?
N1A C1 C6 C5 -169.6(3) . . . . ?


_ins_header                      
;
TITL ek1923_a in C2/c 
REM C2/c (#15 in standard setting)
CELL 1.54184  14.671952  10.395449  18.971650  90.0000  93.2637  90.0000
ZERR    7.00   0.000261   0.000174   0.000334   0.0000   0.0016   0.0000
LATT  7
SYMM -x, y,-z+1/2 
SFAC C H N O Cl
UNIT 112.00 98.00 7.00 28.00 7.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.414
_oxdiff_exptl_absorpt_empirical_full_min 0.848
####################################################################### 
# 
# 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_compound_3b
_database_code_depnum_ccdc_archive 'CCDC 2058516'
loop_
_audit_author_name
_audit_author_address
'Jari Konu'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N O2 S'
_chemical_formula_sum            'C13 H11 N O2 S'
_chemical_formula_weight         245.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.2659(2)
_cell_length_b                   7.50740(10)
_cell_length_c                   27.4441(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.743(2)
_cell_angle_gamma                90
_cell_volume                     2318.50(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4974
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.5610
_cell_measurement_theta_min      4.1500
_shelx_estimated_absorpt_T_max   0.870
_shelx_estimated_absorpt_T_min   0.646
_exptl_absorpt_coefficient_mu    2.390
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 -5 0.0302
1 -1 5 0.0302
5 2 -3 0.0807
-5 -2 3 0.0807

_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0015 1.0014 -4.9976 -0.3561 0.0576 -0.1164
1.0015 -1.0014 4.9976 0.3561 -0.0576 0.1164
5.0008 2.0015 -3.0031 -0.1874 -0.7838 -0.0713
-5.0008 -2.0015 3.0031 0.1874 0.7838 0.0713

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            9641
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.833
_diffrn_reflns_theta_min         3.224
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00  -3.00   1.00   10.00    --  -41.78 -19.00   0.00  116
  2  ω    -66.00  25.00   1.00   10.00    --  -41.78  37.00-180.00   91
  3  ω      5.00  31.00   1.00   10.00    --   41.78 -99.00 -90.00   26
  4  ω     38.00 136.00   1.00   40.00    --  112.00 -30.00 150.00   98
  5  ω     39.00 116.00   1.00   40.00    --  112.00-111.00  90.00   77
  6  ω    108.00 162.00   1.00   40.00    --  112.00 111.00-150.00   54
  7  ω     87.00 175.00   1.00   40.00    --  112.00  45.00 -30.00   88
  8  ω     32.00 109.00   1.00   40.00    --  112.00 -94.00 120.00   77
  9  ω     41.00 124.00   1.00   40.00    --  112.00 -77.00 150.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0228830000
_diffrn_orient_matrix_UB_12      -0.0726041000
_diffrn_orient_matrix_UB_13      0.0521205000
_diffrn_orient_matrix_UB_21      -0.1275872000
_diffrn_orient_matrix_UB_22      -0.0740366000
_diffrn_orient_matrix_UB_23      -0.0007968000
_diffrn_orient_matrix_UB_31      0.0439977000
_diffrn_orient_matrix_UB_32      -0.1770865000
_diffrn_orient_matrix_UB_33      -0.0210162000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4115
_reflns_number_total             4756
_reflns_odcompleteness_completeness 98.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4756
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0495P)²+0.5040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0929
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.38690(3) 0.26676(5) 0.87363(2) 0.02461(10) Uani 1 1 d . . . . .
O1 O 0.19211(13) 0.23327(19) 0.53427(5) 0.0440(3) Uani 1 1 d . . . . .
O2 O 0.27967(11) 0.48928(17) 0.53154(4) 0.0354(3) Uani 1 1 d . . . . .
N1 N 0.24618(11) 0.35852(19) 0.55384(5) 0.0285(3) Uani 1 1 d . . . . .
C1 C 0.27439(13) 0.3481(2) 0.60629(5) 0.0231(3) Uani 1 1 d . . . . .
C2 C 0.37394(13) 0.4375(2) 0.62504(5) 0.0249(3) Uani 1 1 d . . . . .
H2 H 0.420307 0.504853 0.604798 0.030 Uiso 1 1 calc R . . . .
C3 C 0.40293(13) 0.4249(2) 0.67421(6) 0.0250(3) Uani 1 1 d . . . . .
H3 H 0.470474 0.482507 0.687051 0.030 Uiso 1 1 calc R . . . .
C4 C 0.33233(13) 0.32637(19) 0.70535(5) 0.0230(3) Uani 1 1 d . . . . .
C5 C 0.23024(13) 0.2421(2) 0.68479(6) 0.0261(3) Uani 1 1 d . . . . .
H5 H 0.181058 0.179286 0.704947 0.031 Uiso 1 1 calc R . . . .
C6 C 0.20131(13) 0.2505(2) 0.63529(6) 0.0263(3) Uani 1 1 d . . . . .
H6 H 0.134608 0.192192 0.621912 0.032 Uiso 1 1 calc R . . . .
C7 C 0.36071(13) 0.3078(2) 0.75759(5) 0.0248(3) Uani 1 1 d . . . . .
H7 H 0.307480 0.243716 0.775635 0.030 Uiso 1 1 calc R . . . .
C8 C 0.45681(13) 0.37507(19) 0.78186(5) 0.0238(3) Uani 1 1 d . . . . .
H8 H 0.512213 0.433089 0.763447 0.029 Uiso 1 1 calc R . . . .
C9 C 0.48226(13) 0.3658(2) 0.83386(5) 0.0232(3) Uani 1 1 d . . . . .
C10 C 0.57748(13) 0.4396(2) 0.85943(5) 0.0247(3) Uani 1 1 d . . . . .
H10 H 0.638800 0.498374 0.844594 0.030 Uiso 1 1 calc R . . . .
C11 C 0.57368(13) 0.4178(2) 0.91063(6) 0.0263(3) Uani 1 1 d . . . . .
H11 H 0.632182 0.460387 0.932689 0.032 Uiso 1 1 calc R . . . .
C12 C 0.47531(13) 0.3277(2) 0.92425(5) 0.0252(3) Uani 1 1 d . . . . .
C13 C 0.44099(15) 0.2758(3) 0.97428(6) 0.0335(4) Uani 1 1 d . . . . .
H13A H 0.361059 0.313960 0.979076 0.050 Uiso 1 1 calc GR . . . .
H13B H 0.493958 0.331347 0.998144 0.050 Uiso 1 1 calc GR . . . .
H13C H 0.445915 0.148715 0.977733 0.050 Uiso 1 1 calc GR . . . .
S2 S 0.40960(3) 0.09515(5) 0.19055(2) 0.02391(10) Uani 1 1 d . . . . .
O3 O 0.50870(12) 0.29247(19) 0.53430(4) 0.0402(3) Uani 1 1 d . . . . .
O4 O 0.66421(10) 0.13359(17) 0.52133(4) 0.0346(3) Uani 1 1 d . . . . .
N2 N 0.57040(12) 0.20580(18) 0.50739(5) 0.0275(3) Uani 1 1 d . . . . .
C14 C 0.53095(13) 0.1861(2) 0.45605(5) 0.0242(3) Uani 1 1 d . . . . .
C15 C 0.42279(13) 0.2599(2) 0.43982(6) 0.0260(3) Uani 1 1 d . . . . .
H15 H 0.374805 0.318125 0.461399 0.031 Uiso 1 1 calc R . . . .
C16 C 0.38817(13) 0.2449(2) 0.39103(6) 0.0244(3) Uani 1 1 d . . . . .
H16 H 0.315707 0.292496 0.379823 0.029 Uiso 1 1 calc R . . . .
C17 C 0.46085(13) 0.1585(2) 0.35794(5) 0.0231(3) Uani 1 1 d . . . . .
C18 C 0.56803(13) 0.0835(2) 0.37634(6) 0.0272(3) Uani 1 1 d . . . . .
H18 H 0.616314 0.023686 0.355177 0.033 Uiso 1 1 calc R . . . .
C19 C 0.60350(13) 0.0962(2) 0.42507(6) 0.0269(3) Uani 1 1 d . . . . .
H19 H 0.674576 0.045515 0.436797 0.032 Uiso 1 1 calc R . . . .
C20 C 0.43189(13) 0.1457(2) 0.30556(5) 0.0243(3) Uani 1 1 d . . . . .
H20 H 0.487353 0.088453 0.287001 0.029 Uiso 1 1 calc R . . . .
C21 C 0.33425(13) 0.20738(19) 0.28131(5) 0.0230(3) Uani 1 1 d . . . . .
H21 H 0.278616 0.267106 0.299221 0.028 Uiso 1 1 calc R . . . .
C22 C 0.30880(13) 0.18809(19) 0.22937(5) 0.0223(3) Uani 1 1 d . . . . .
C23 C 0.20738(13) 0.2371(2) 0.20343(6) 0.0242(3) Uani 1 1 d . . . . .
H23 H 0.142520 0.288732 0.217699 0.029 Uiso 1 1 calc R . . . .
C24 C 0.21036(13) 0.2018(2) 0.15259(6) 0.0256(3) Uani 1 1 d . . . . .
H24 H 0.147780 0.227398 0.130368 0.031 Uiso 1 1 calc R . . . .
C25 C 0.31444(13) 0.1266(2) 0.13985(5) 0.0242(3) Uani 1 1 d . . . . .
C26 C 0.35244(15) 0.0787(2) 0.08994(6) 0.0305(3) Uani 1 1 d . . . . .
H26A H 0.423813 0.142290 0.083286 0.046 Uiso 1 1 calc GR . . . .
H26B H 0.290779 0.110294 0.066154 0.046 Uiso 1 1 calc GR . . . .
H26C H 0.367095 -0.047071 0.088405 0.046 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C9 1.7352(14) . ?
S1 C12 1.7317(16) . ?
O1 N1 1.2299(19) . ?
O2 N1 1.2259(19) . ?
N1 C1 1.4612(19) . ?
C1 C2 1.385(2) . ?
C1 C6 1.382(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.405(2) . ?
C4 C5 1.407(2) . ?
C4 C7 1.460(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.342(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.444(2) . ?
C9 C10 1.370(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.417(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.365(2) . ?
C12 C13 1.496(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
S2 C22 1.7399(14) . ?
S2 C25 1.7315(15) . ?
O3 N2 1.2252(19) . ?
O4 N2 1.2323(18) . ?
N2 C14 1.4646(19) . ?
C14 C15 1.392(2) . ?
C14 C19 1.383(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.409(2) . ?
C17 C18 1.404(2) . ?
C17 C20 1.462(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.341(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.448(2) . ?
C22 C23 1.367(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.422(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.362(2) . ?
C25 C26 1.498(2) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S1 C9 92.39(7) . . ?
O1 N1 C1 117.97(14) . . ?
O2 N1 O1 123.50(14) . . ?
O2 N1 C1 118.51(13) . . ?
C2 C1 N1 118.30(13) . . ?
C6 C1 N1 119.23(14) . . ?
C6 C1 C2 122.47(14) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.74(13) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.20(14) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 117.91(14) . . ?
C3 C4 C7 122.93(14) . . ?
C5 C4 C7 119.16(13) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.55(14) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 118.09(14) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C4 C7 H7 117.1 . . ?
C8 C7 C4 125.78(13) . . ?
C8 C7 H7 117.1 . . ?
C7 C8 H8 116.9 . . ?
C7 C8 C9 126.14(13) . . ?
C9 C8 H8 116.9 . . ?
C8 C9 S1 122.87(11) . . ?
C10 C9 S1 110.12(11) . . ?
C10 C9 C8 126.90(13) . . ?
C9 C10 H10 123.2 . . ?
C9 C10 C11 113.65(13) . . ?
C11 C10 H10 123.2 . . ?
C10 C11 H11 123.5 . . ?
C12 C11 C10 113.07(14) . . ?
C12 C11 H11 123.5 . . ?
C11 C12 S1 110.77(11) . . ?
C11 C12 C13 128.98(15) . . ?
C13 C12 S1 120.22(12) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C25 S2 C22 92.31(7) . . ?
O3 N2 O4 123.33(14) . . ?
O3 N2 C14 118.60(13) . . ?
O4 N2 C14 118.07(13) . . ?
C15 C14 N2 119.23(14) . . ?
C19 C14 N2 118.66(14) . . ?
C19 C14 C15 122.10(14) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 C14 118.68(14) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.09(14) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C20 123.69(14) . . ?
C18 C17 C16 117.97(14) . . ?
C18 C17 C20 118.34(13) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.63(14) . . ?
C19 C18 H18 119.2 . . ?
C14 C19 H19 120.8 . . ?
C18 C19 C14 118.49(14) . . ?
C18 C19 H19 120.8 . . ?
C17 C20 H20 116.4 . . ?
C21 C20 C17 127.19(14) . . ?
C21 C20 H20 116.4 . . ?
C20 C21 H21 117.5 . . ?
C20 C21 C22 124.97(13) . . ?
C22 C21 H21 117.5 . . ?
C21 C22 S2 122.60(11) . . ?
C23 C22 S2 110.05(11) . . ?
C23 C22 C21 127.35(13) . . ?
C22 C23 H23 123.1 . . ?
C22 C23 C24 113.71(13) . . ?
C24 C23 H23 123.1 . . ?
C23 C24 H24 123.5 . . ?
C25 C24 C23 112.97(14) . . ?
C25 C24 H24 123.5 . . ?
C24 C25 S2 110.95(11) . . ?
C24 C25 C26 128.42(14) . . ?
C26 C25 S2 120.59(12) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C13 H13A O4 0.96 2.58 3.498(2) 159.8 4_566 yes
C13 H13B O1 0.96 2.45 3.205(2) 135.7 4_666 yes
C15 H15 O2 0.93 2.59 3.5057(19) 168.8 . yes

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
S1 C9 C10 C11 -0.37(17) . . . . ?
O1 N1 C1 C2 151.90(15) . . . . ?
O1 N1 C1 C6 -28.3(2) . . . . ?
O2 N1 C1 C2 -26.6(2) . . . . ?
O2 N1 C1 C6 153.26(14) . . . . ?
N1 C1 C2 C3 -178.39(13) . . . . ?
N1 C1 C6 C5 179.73(13) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C2 C1 C6 C5 -0.4(2) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C2 C3 C4 C7 179.25(14) . . . . ?
C3 C4 C5 C6 1.9(2) . . . . ?
C3 C4 C7 C8 -2.2(2) . . . . ?
C4 C5 C6 C1 -1.4(2) . . . . ?
C4 C7 C8 C9 176.34(14) . . . . ?
C5 C4 C7 C8 177.54(15) . . . . ?
C6 C1 C2 C3 1.8(2) . . . . ?
C7 C4 C5 C6 -177.88(14) . . . . ?
C7 C8 C9 S1 -1.4(2) . . . . ?
C7 C8 C9 C10 -177.29(15) . . . . ?
C8 C9 C10 C11 175.94(14) . . . . ?
C9 S1 C12 C11 -0.72(12) . . . . ?
C9 S1 C12 C13 -178.95(14) . . . . ?
C9 C10 C11 C12 -0.2(2) . . . . ?
C10 C11 C12 S1 0.64(17) . . . . ?
C10 C11 C12 C13 178.68(16) . . . . ?
C12 S1 C9 C8 -175.86(13) . . . . ?
C12 S1 C9 C10 0.62(12) . . . . ?
S2 C22 C23 C24 -0.43(16) . . . . ?
O3 N2 C14 C15 -2.5(2) . . . . ?
O3 N2 C14 C19 176.67(14) . . . . ?
O4 N2 C14 C15 177.28(14) . . . . ?
O4 N2 C14 C19 -3.5(2) . . . . ?
N2 C14 C15 C16 178.15(13) . . . . ?
N2 C14 C19 C18 -177.70(14) . . . . ?
C14 C15 C16 C17 -0.7(2) . . . . ?
C15 C14 C19 C18 1.5(2) . . . . ?
C15 C16 C17 C18 1.9(2) . . . . ?
C15 C16 C17 C20 -176.98(14) . . . . ?
C16 C17 C18 C19 -1.4(2) . . . . ?
C16 C17 C20 C21 -1.7(2) . . . . ?
C17 C18 C19 C14 -0.2(2) . . . . ?
C17 C20 C21 C22 -178.74(14) . . . . ?
C18 C17 C20 C21 179.48(15) . . . . ?
C19 C14 C15 C16 -1.0(2) . . . . ?
C20 C17 C18 C19 177.51(14) . . . . ?
C20 C21 C22 S2 -5.1(2) . . . . ?
C20 C21 C22 C23 175.05(15) . . . . ?
C21 C22 C23 C24 179.40(14) . . . . ?
C22 S2 C25 C24 -0.95(12) . . . . ?
C22 S2 C25 C26 177.01(13) . . . . ?
C22 C23 C24 C25 -0.29(19) . . . . ?
C23 C24 C25 S2 0.88(17) . . . . ?
C23 C24 C25 C26 -176.88(15) . . . . ?
C25 S2 C22 C21 -179.06(12) . . . . ?
C25 S2 C22 C23 0.78(12) . . . . ?


_ins_header                      
;
TITL ek1834_m in P2(1)/n 
REM P2(1)/n (#14 in standard setting)
CELL 1.54184  11.265928   7.507423  27.444062  90.0000  92.7428  90.0000
ZERR   10.00   0.000210   0.000130   0.000445   0.0000   0.0016   0.0000
LATT  1
SYMM -x+1/2, y+1/2,-z+1/2 
SFAC C H N O
UNIT 110.00 100.00 10.00 10.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.247
_oxdiff_exptl_absorpt_empirical_full_min 0.772
####################################################################### 
# 
# 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_compound_1c
_database_code_depnum_ccdc_archive 'CCDC 2058511'
loop_
_audit_author_name
_audit_author_address
'Jari Konu'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H13 N1 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.6720(2)
_cell_length_b                   11.8172(2)
_cell_length_c                   14.7910(2)
_cell_angle_alpha                109.5280(10)
_cell_angle_beta                 103.3890(10)
_cell_angle_gamma                90.9490(10)
_cell_volume                     1860.67(5)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    44313
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.5430
_cell_measurement_theta_min      3.2260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             804
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 -5 4 0.1564
-3 -1 5 0.1148
5 5 -4 0.0564
1 -2 -5 0.1515
-1 2 5 0.0805
5 -4 4 0.0724
3 1 -5 0.1148
-5 4 -4 0.0914

_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.164
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.0039 -4.9975 3.9998 -0.2687 -0.5057 -0.7410
-2.9999 -0.9985 4.9996 -0.2416 -0.5397 -0.0438
5.0039 4.9975 -3.9998 0.2687 0.5057 0.7410
0.9969 -2.0005 -4.9994 0.1708 0.4852 -0.4699
-0.9969 2.0005 4.9994 -0.1708 -0.4852 0.4699
5.0006 -3.9991 3.9997 0.8624 -0.3734 0.0485
2.9999 0.9985 -4.9996 0.2416 0.5397 0.0438
-5.0006 3.9991 -3.9997 -0.8624 0.3734 -0.0485

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            72195
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.984
_diffrn_reflns_theta_min         3.276
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  25.00   1.00    1.00    --   38.00  95.00-153.25   26
  2  ω   -116.00 -17.00   1.00    1.00    --  -41.78 -37.00 -30.00   99
  3  ω    -66.00  33.00   1.00    1.00    --  -41.78  37.00 150.00   99
  4  ω    -34.00  74.00   1.00    1.00    --   41.78 -77.00-180.00  108
  5  ω     14.00 114.00   1.00    1.00    --   41.78  57.00 150.00  100
  6  ω     17.00 116.00   1.00    1.00    --   41.78  37.00  30.00   99
  7  ω     23.00  98.00   1.00    1.00    --   41.78-125.00  60.00   75
  8  ω     11.00  38.00   1.00    1.00    --   46.00  84.00  23.63   27
  9  ω     17.00  45.00   1.00    1.00    --   50.00  80.00 -29.30   28
 10  ω     16.00  45.00   1.00    1.00    --   50.00  82.00  98.61   29
 11  ω     16.00  45.00   1.00    1.00    --   50.00  82.00-134.05   29
 12  ω     17.00  45.00   1.00    1.00    --   50.00  80.00 -96.44   28
 13  ω     30.00 137.00   1.00    1.00    --   62.00  75.00  56.98  107
 14  ω     29.00 138.00   1.00    1.00    --   62.00  77.00 166.54  109
 15  ω     34.00 142.00   1.00    1.00    --   66.00  76.00 -21.20  108
 16  ω     34.00 142.00   1.00    1.00    --   66.00  76.00-122.58  108
 17  ω     34.00 141.00   1.00    1.00    --   66.00  75.00 -89.04  107
 18  ω     33.00 142.00   1.00    1.00    --   66.00  77.00 109.95  109
 19  ω     38.00 145.00   1.00    1.00    --   70.00  74.00 131.66  107
 20  ω     37.00 146.00   1.00    1.00    --   70.00  77.00 -59.68  109
 21  ω     41.00 150.00   1.00    1.00    --   74.00  77.00-125.49  109
 22  ω     42.00 150.00   1.00    1.00    --   74.00  76.00-164.20  108
 23  ω     47.00 151.00   1.00    3.00    --   78.00  69.00  80.42  104
 24  ω     53.00 154.00   1.00    3.00    --   82.00  62.00 119.13  101
 25  ω     52.00 155.00   1.00    3.00    --   82.00  65.00 -23.54  103
 26  ω     50.00 157.00   1.00    3.00    --   82.00  74.00   0.50  107
 27  ω     52.00 155.00   1.00    3.00    --   82.00  68.00-163.33  103
 28  ω     55.00 159.00   1.00    3.00    --   86.00  69.00 158.37  104
 29  ω     53.00 162.00   1.00    3.00    --   86.00  77.00  14.40  109
 30  ω     55.00 160.00   1.00    3.00    --   86.00  72.00-140.26  105
 31  ω     76.00 178.00   1.00    3.00    --  106.00  68.00  67.11  102
 32  ω     83.00 178.00   1.00    3.00    --  112.00  61.00   0.00   95
 33  ω     79.00 178.00   1.00    3.00    --  112.00  77.00  60.00   99
 34  ω     83.00 178.00   1.00    3.00    --  112.00  61.00 -90.00   95
 35  ω     29.00 109.00   1.00    3.00    --  112.00 -94.00  90.00   80
 36  ω     79.00 178.00   1.00    3.00    --  112.00  77.00 150.00   99
 37  ω     36.00 116.00   1.00    3.00    --  112.00-111.00-150.00   80
 38  ω     79.00 178.00   1.00    3.00    --  112.00  77.00   0.00   99
 39  ω     79.00 178.00   1.00    3.00    --  112.00  77.00 -90.00   99
 40  ω     36.00 116.00   1.00    3.00    --  112.00-111.00  60.00   80
 41  ω     79.00 178.00   1.00    3.00    --  112.00  77.00 120.00   99
 42  ω     29.00 109.00   1.00    3.00    --  112.00 -94.00 -90.00   80
 43  ω     79.00 178.00   1.00    3.00    --  112.00  77.00-150.00   99
 44  ω     79.00 178.00   1.00    3.00    --  112.00  77.00  90.00   99
 45  ω     36.00 116.00   1.00    3.00    --  112.00-111.00  30.00   80
 46  ω     40.00 141.00   1.00    3.00    --  112.00 -61.00 120.00  101
 47  ω     79.00 178.00   1.00    3.00    --  112.00  77.00 -60.00   99
 48  ω     79.00 178.00   1.00    3.00    --  112.00  77.00-120.00   99
 49  ω     83.00 178.00   1.00    3.00    --  112.00  61.00-120.00   95
 50  ω     83.00 178.00   1.00    3.00    --  112.00  61.00  90.00   95
 51  ω     79.00 178.00   1.00    3.00    --  112.00  77.00-180.00   99
 52  ω     79.00 178.00   1.00    3.00    --  112.00  77.00  30.00   99
 53  ω     29.00 109.00   1.00    3.00    --  112.00 -94.00 120.00   80
 54  ω     29.00 109.00   1.00    3.00    --  112.00 -94.00 -30.00   80
 55  ω     79.00 178.00   1.00    3.00    --  112.00  77.00 -30.00   99
 56  ω     83.00 178.00   1.00    3.00    --  112.00  61.00 150.00   95
 57  ω   -114.00 -14.00   1.00    1.00    --  -41.78 -57.00-180.00  100
 58  ω      6.00  33.00   1.00    1.00    --   42.00  88.00  71.80   27
 59  ω     16.00 119.00   1.00    1.00    --   46.00  67.00 -14.87  103
 60  ω     11.00  38.00   1.00    1.00    --   46.00  84.00 177.90   27
 61  ω     26.00 133.00   1.00    1.00    --   58.00  75.00  18.53  107
 62  ω     34.00 132.00   1.00    1.00    --   66.00  76.00  82.90   98
 63  ω     38.00 146.00   1.00    1.00    --   70.00  76.00-171.19  108
 64  ω     38.00 145.00   1.00    1.00    --   70.00  75.00   3.28  107
 65  ω     44.00 147.00   1.00    1.00    --   74.00  66.00  57.91  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1186014000
_diffrn_orient_matrix_UB_12      -0.0556060000
_diffrn_orient_matrix_UB_13      0.0117282000
_diffrn_orient_matrix_UB_21      0.0122192000
_diffrn_orient_matrix_UB_22      0.0100232000
_diffrn_orient_matrix_UB_23      -0.0986176000
_diffrn_orient_matrix_UB_31      0.0662386000
_diffrn_orient_matrix_UB_32      0.1270589000
_diffrn_orient_matrix_UB_33      0.0563507000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7134
_reflns_number_total             7769
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         7769
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0573P)²+0.5361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1103
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25),
  C26(H26), C28(H28), C29(H29), C32(H32), C33(H33), C35(H35), C36(H36),
 C37(H37), C38(H38), C40(H40), C41(H41), C43(H43), C44(H44)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C30(H30A,H30B,H30C), C45(H45A,H45B,H45C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.16751(8) 0.73065(8) 0.58984(7) 0.0375(2) Uani 1 1 d . . . . .
O2 O 1.00910(8) 0.81279(9) 0.61786(7) 0.0419(2) Uani 1 1 d . . . . .
O3 O 1.78640(8) 1.55719(8) 1.36073(6) 0.03211(19) Uani 1 1 d . . . . .
N1 N 1.11708(9) 0.80975(9) 0.63907(7) 0.0286(2) Uani 1 1 d . . . . .
C1 C 1.18841(10) 0.90451(10) 0.72737(8) 0.0251(2) Uani 1 1 d . . . . .
C2 C 1.31038(10) 0.90469(10) 0.74939(8) 0.0267(2) Uani 1 1 d . . . . .
H2 H 1.346058 0.846029 0.708559 0.032 Uiso 1 1 calc R . . . .
C3 C 1.37818(10) 0.99344(10) 0.83300(8) 0.0265(2) Uani 1 1 d . . . . .
H3 H 1.460130 0.993927 0.848530 0.032 Uiso 1 1 calc R . . . .
C4 C 1.32549(10) 1.08285(10) 0.89487(8) 0.0247(2) Uani 1 1 d . . . . .
C5 C 1.20178(10) 1.07961(11) 0.86925(8) 0.0290(2) Uani 1 1 d . . . . .
H5 H 1.165385 1.138738 0.908974 0.035 Uiso 1 1 calc R . . . .
C6 C 1.13247(10) 0.99063(11) 0.78632(9) 0.0298(2) Uani 1 1 d . . . . .
H6 H 1.050395 0.988753 0.770605 0.036 Uiso 1 1 calc R . . . .
C7 C 1.39412(10) 1.17884(10) 0.98431(8) 0.0260(2) Uani 1 1 d . . . . .
H7 H 1.351767 1.235830 1.019517 0.031 Uiso 1 1 calc R . . . .
C8 C 1.51191(10) 1.19229(10) 1.02012(8) 0.0260(2) Uani 1 1 d . . . . .
H8 H 1.553555 1.134926 0.984431 0.031 Uiso 1 1 calc R . . . .
C9 C 1.58247(10) 1.28679(10) 1.10885(8) 0.0241(2) Uani 1 1 d . . . . .
C10 C 1.70562(10) 1.28887(10) 1.13386(8) 0.0263(2) Uani 1 1 d . . . . .
H10 H 1.740738 1.229201 1.093372 0.032 Uiso 1 1 calc R . . . .
C11 C 1.77772(10) 1.37646(10) 1.21676(8) 0.0262(2) Uani 1 1 d . . . . .
H11 H 1.859491 1.375203 1.231308 0.031 Uiso 1 1 calc R . . . .
C12 C 1.72597(10) 1.46619(10) 1.27781(8) 0.0256(2) Uani 1 1 d . . . . .
C13 C 1.60299(11) 1.46513(11) 1.25492(8) 0.0297(2) Uani 1 1 d . . . . .
H13 H 1.568012 1.524316 1.295974 0.036 Uiso 1 1 calc R . . . .
C14 C 1.53272(10) 1.37769(10) 1.17242(8) 0.0277(2) Uani 1 1 d . . . . .
H14 H 1.450943 1.378812 1.158543 0.033 Uiso 1 1 calc R . . . .
C15 C 1.91287(11) 1.56102(13) 1.38723(9) 0.0379(3) Uani 1 1 d . . . . .
H15A H 1.943380 1.566347 1.333666 0.057 Uiso 1 1 calc GR . . . .
H15B H 1.935022 1.489023 1.400252 0.057 Uiso 1 1 calc GR . . . .
H15C H 1.944952 1.630250 1.445511 0.057 Uiso 1 1 calc GR . . . .
O4 O 0.12296(8) 0.29687(8) 0.07324(6) 0.0375(2) Uani 1 1 d . . . . .
O5 O 0.01468(8) 0.24875(8) 0.15814(7) 0.0389(2) Uani 1 1 d . . . . .
O6 O 0.84524(7) 1.00735(7) 0.84433(6) 0.03191(19) Uani 1 1 d . . . . .
N2 N 0.09895(8) 0.30765(9) 0.15258(7) 0.0296(2) Uani 1 1 d . . . . .
C16 C 0.17523(9) 0.39271(10) 0.24357(8) 0.0243(2) Uani 1 1 d . . . . .
C17 C 0.25248(10) 0.47770(10) 0.23611(8) 0.0261(2) Uani 1 1 d . . . . .
H17 H 0.252942 0.482450 0.174690 0.031 Uiso 1 1 calc R . . . .
C18 C 0.32858(9) 0.55500(10) 0.32151(8) 0.0257(2) Uani 1 1 d . . . . .
H18 H 0.380045 0.613019 0.317463 0.031 Uiso 1 1 calc R . . . .
C19 C 0.32967(9) 0.54755(10) 0.41482(8) 0.0241(2) Uani 1 1 d . . . . .
C20 C 0.24760(10) 0.46273(10) 0.41882(8) 0.0257(2) Uani 1 1 d . . . . .
H20 H 0.245195 0.458515 0.480033 0.031 Uiso 1 1 calc R . . . .
C21 C 0.16996(10) 0.38502(10) 0.33397(8) 0.0260(2) Uani 1 1 d . . . . .
H21 H 0.115711 0.329129 0.337543 0.031 Uiso 1 1 calc R . . . .
C22 C 0.41237(10) 0.62409(10) 0.50661(8) 0.0256(2) Uani 1 1 d . . . . .
H22 H 0.398820 0.622929 0.565845 0.031 Uiso 1 1 calc R . . . .
C23 C 0.50587(10) 0.69564(10) 0.51263(8) 0.0255(2) Uani 1 1 d . . . . .
H23 H 0.518406 0.695745 0.452815 0.031 Uiso 1 1 calc R . . . .
C24 C 0.59066(9) 0.77375(9) 0.60250(8) 0.0241(2) Uani 1 1 d . . . . .
C25 C 0.68385(10) 0.84119(10) 0.59242(8) 0.0267(2) Uani 1 1 d . . . . .
H25 H 0.689969 0.834198 0.529231 0.032 Uiso 1 1 calc R . . . .
C26 C 0.76666(10) 0.91760(10) 0.67367(8) 0.0267(2) Uani 1 1 d . . . . .
H26 H 0.827361 0.961575 0.664857 0.032 Uiso 1 1 calc R . . . .
C27 C 0.75944(10) 0.92892(10) 0.76888(8) 0.0252(2) Uani 1 1 d . . . . .
C28 C 0.66844(10) 0.86180(10) 0.78136(8) 0.0271(2) Uani 1 1 d . . . . .
H28 H 0.663250 0.868099 0.844630 0.032 Uiso 1 1 calc R . . . .
C29 C 0.58570(9) 0.78552(10) 0.69845(8) 0.0261(2) Uani 1 1 d . . . . .
H29 H 0.525342 0.741087 0.707250 0.031 Uiso 1 1 calc R . . . .
C30 C 0.84282(12) 1.01865(12) 0.94320(9) 0.0375(3) Uani 1 1 d . . . . .
H30A H 0.853819 0.942305 0.951973 0.056 Uiso 1 1 calc GR . . . .
H30B H 0.767856 1.043223 0.954487 0.056 Uiso 1 1 calc GR . . . .
H30C H 0.905179 1.077992 0.989485 0.056 Uiso 1 1 calc GR . . . .
O7 O -0.01041(8) 0.53654(9) 0.14308(7) 0.0388(2) Uani 1 1 d . . . . .
O8 O -0.14757(9) 0.65658(9) 0.16146(7) 0.0443(2) Uani 1 1 d . . . . .
O9 O -0.88468(7) -0.10681(7) -0.57177(6) 0.02994(18) Uani 1 1 d . . . . .
N3 N -0.11138(9) 0.56225(9) 0.11678(7) 0.0290(2) Uani 1 1 d . . . . .
C31 C -0.19277(10) 0.47610(10) 0.02957(8) 0.0253(2) Uani 1 1 d . . . . .
C32 C -0.31032(10) 0.49833(11) 0.00527(9) 0.0285(2) Uani 1 1 d . . . . .
H32 H -0.336455 0.568721 0.042171 0.034 Uiso 1 1 calc R . . . .
C33 C -0.38780(10) 0.41305(11) -0.07533(9) 0.0305(2) Uani 1 1 d . . . . .
H33 H -0.466976 0.426387 -0.091934 0.037 Uiso 1 1 calc R . . . .
C34 C -0.34939(11) 0.30694(11) -0.13248(8) 0.0287(2) Uani 1 1 d . . . . .
C35 C -0.22999(11) 0.28969(11) -0.10596(8) 0.0297(2) Uani 1 1 d . . . . .
H35 H -0.202580 0.220645 -0.143541 0.036 Uiso 1 1 calc R . . . .
C36 C -0.15149(10) 0.37278(11) -0.02517(8) 0.0284(2) Uani 1 1 d . . . . .
H36 H -0.072373 0.359537 -0.007870 0.034 Uiso 1 1 calc R . . . .
C37 C -0.42831(11) 0.21473(11) -0.21877(9) 0.0298(2) Uani 1 1 d . . . . .
H37 H -0.395072 0.147694 -0.252737 0.036 Uiso 1 1 calc R . . . .
C38 C -0.54399(11) 0.21950(11) -0.25233(9) 0.0299(2) Uani 1 1 d . . . . .
H38 H -0.575773 0.287242 -0.217667 0.036 Uiso 1 1 calc R . . . .
C39 C -0.62626(10) 0.13035(10) -0.33731(8) 0.0274(2) Uani 1 1 d . . . . .
C40 C -0.74597(11) 0.15019(10) -0.35618(8) 0.0284(2) Uani 1 1 d . . . . .
H40 H -0.769602 0.219409 -0.315290 0.034 Uiso 1 1 calc R . . . .
C41 C -0.82962(10) 0.06968(10) -0.43384(8) 0.0278(2) Uani 1 1 d . . . . .
H41 H -0.908659 0.084814 -0.444973 0.033 Uiso 1 1 calc R . . . .
C42 C -0.79553(10) -0.03462(10) -0.49576(8) 0.0241(2) Uani 1 1 d . . . . .
C43 C -0.67709(10) -0.05720(10) -0.47859(8) 0.0269(2) Uani 1 1 d . . . . .
H43 H -0.653996 -0.126878 -0.519348 0.032 Uiso 1 1 calc R . . . .
C44 C -0.59383(10) 0.02505(11) -0.40021(9) 0.0287(2) Uani 1 1 d . . . . .
H44 H -0.514791 0.009920 -0.389224 0.034 Uiso 1 1 calc R . . . .
C45 C -0.85585(12) -0.21672(11) -0.63581(9) 0.0350(3) Uani 1 1 d . . . . .
H45A H -0.925452 -0.257984 -0.686611 0.052 Uiso 1 1 calc GR . . . .
H45B H -0.826381 -0.267037 -0.598148 0.052 Uiso 1 1 calc GR . . . .
H45C H -0.796326 -0.199071 -0.665741 0.052 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.2297(13) . ?
O2 N1 1.2305(13) . ?
O3 C12 1.3604(13) . ?
O3 C15 1.4327(16) . ?
N1 C1 1.4631(14) . ?
C1 C2 1.3848(16) . ?
C1 C6 1.3837(16) . ?
C2 H2 0.9300 . ?
C2 C3 1.3811(16) . ?
C3 H3 0.9300 . ?
C3 C4 1.4029(16) . ?
C4 C5 1.4018(16) . ?
C4 C7 1.4678(15) . ?
C5 H5 0.9300 . ?
C5 C6 1.3837(16) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.3399(16) . ?
C8 H8 0.9300 . ?
C8 C9 1.4618(15) . ?
C9 C10 1.3964(16) . ?
C9 C14 1.4048(16) . ?
C10 H10 0.9300 . ?
C10 C11 1.3885(16) . ?
C11 H11 0.9300 . ?
C11 C12 1.3923(16) . ?
C12 C13 1.3952(17) . ?
C13 H13 0.9300 . ?
C13 C14 1.3765(16) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O4 N2 1.2351(13) . ?
O5 N2 1.2295(14) . ?
O6 C27 1.3666(13) . ?
O6 C30 1.4303(15) . ?
N2 C16 1.4578(14) . ?
C16 C17 1.3872(16) . ?
C16 C21 1.3853(15) . ?
C17 H17 0.9300 . ?
C17 C18 1.3787(16) . ?
C18 H18 0.9300 . ?
C18 C19 1.4093(15) . ?
C19 C20 1.3999(15) . ?
C19 C22 1.4617(15) . ?
C20 H20 0.9300 . ?
C20 C21 1.3837(15) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.3371(16) . ?
C23 H23 0.9300 . ?
C23 C24 1.4625(15) . ?
C24 C25 1.4022(15) . ?
C24 C29 1.3939(15) . ?
C25 H25 0.9300 . ?
C25 C26 1.3790(15) . ?
C26 H26 0.9300 . ?
C26 C27 1.3919(15) . ?
C27 C28 1.3972(16) . ?
C28 H28 0.9300 . ?
C28 C29 1.3901(16) . ?
C29 H29 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
O7 N3 1.2293(13) . ?
O8 N3 1.2289(14) . ?
O9 C42 1.3646(13) . ?
O9 C45 1.4272(14) . ?
N3 C31 1.4579(14) . ?
C31 C32 1.3883(16) . ?
C31 C36 1.3847(16) . ?
C32 H32 0.9300 . ?
C32 C33 1.3864(17) . ?
C33 H33 0.9300 . ?
C33 C34 1.4047(17) . ?
C34 C35 1.3955(17) . ?
C34 C37 1.4688(16) . ?
C35 H35 0.9300 . ?
C35 C36 1.3821(16) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C37 C38 1.3355(17) . ?
C38 H38 0.9300 . ?
C38 C39 1.4609(16) . ?
C39 C40 1.3997(16) . ?
C39 C44 1.4007(16) . ?
C40 H40 0.9300 . ?
C40 C41 1.3773(16) . ?
C41 H41 0.9300 . ?
C41 C42 1.3953(15) . ?
C42 C43 1.3935(15) . ?
C43 H43 0.9300 . ?
C43 C44 1.3881(16) . ?
C44 H44 0.9300 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O3 C15 117.54(9) . . ?
O1 N1 O2 123.08(10) . . ?
O1 N1 C1 118.65(10) . . ?
O2 N1 C1 118.27(10) . . ?
C2 C1 N1 118.62(10) . . ?
C6 C1 N1 119.32(10) . . ?
C6 C1 C2 122.06(10) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.91(10) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.10(10) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C7 122.90(10) . . ?
C5 C4 C3 118.00(10) . . ?
C5 C4 C7 119.10(10) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.65(11) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 H6 120.9 . . ?
C5 C6 C1 118.29(11) . . ?
C5 C6 H6 120.9 . . ?
C4 C7 H7 116.9 . . ?
C8 C7 C4 126.29(11) . . ?
C8 C7 H7 116.9 . . ?
C7 C8 H8 116.3 . . ?
C7 C8 C9 127.45(11) . . ?
C9 C8 H8 116.3 . . ?
C10 C9 C8 119.77(10) . . ?
C10 C9 C14 116.96(10) . . ?
C14 C9 C8 123.27(10) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 C9 122.63(10) . . ?
C11 C10 H10 118.7 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.11(10) . . ?
C12 C11 H11 120.4 . . ?
O3 C12 C11 124.94(11) . . ?
O3 C12 C13 115.78(10) . . ?
C11 C12 C13 119.27(10) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 120.91(10) . . ?
C14 C13 H13 119.5 . . ?
C9 C14 H14 119.4 . . ?
C13 C14 C9 121.11(11) . . ?
C13 C14 H14 119.4 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C27 O6 C30 117.12(9) . . ?
O4 N2 C16 118.33(10) . . ?
O5 N2 O4 122.88(10) . . ?
O5 N2 C16 118.78(10) . . ?
C17 C16 N2 118.38(10) . . ?
C21 C16 N2 119.38(10) . . ?
C21 C16 C17 122.23(10) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 C16 118.73(10) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 121.09(10) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C22 122.87(10) . . ?
C20 C19 C18 118.02(10) . . ?
C20 C19 C22 119.12(10) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.65(10) . . ?
C21 C20 H20 119.2 . . ?
C16 C21 H21 120.9 . . ?
C20 C21 C16 118.21(10) . . ?
C20 C21 H21 120.9 . . ?
C19 C22 H22 117.2 . . ?
C23 C22 C19 125.52(10) . . ?
C23 C22 H22 117.2 . . ?
C22 C23 H23 116.3 . . ?
C22 C23 C24 127.44(10) . . ?
C24 C23 H23 116.3 . . ?
C25 C24 C23 118.40(10) . . ?
C29 C24 C23 124.31(10) . . ?
C29 C24 C25 117.29(10) . . ?
C24 C25 H25 119.1 . . ?
C26 C25 C24 121.77(10) . . ?
C26 C25 H25 119.1 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 120.02(10) . . ?
C27 C26 H26 120.0 . . ?
O6 C27 C26 115.51(10) . . ?
O6 C27 C28 124.92(10) . . ?
C26 C27 C28 119.57(10) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 C27 119.49(10) . . ?
C29 C28 H28 120.3 . . ?
C24 C29 H29 119.1 . . ?
C28 C29 C24 121.86(10) . . ?
C28 C29 H29 119.1 . . ?
O6 C30 H30A 109.5 . . ?
O6 C30 H30B 109.5 . . ?
O6 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C42 O9 C45 117.74(9) . . ?
O7 N3 C31 118.61(9) . . ?
O8 N3 O7 123.03(10) . . ?
O8 N3 C31 118.36(10) . . ?
C32 C31 N3 119.05(10) . . ?
C36 C31 N3 119.12(10) . . ?
C36 C31 C32 121.81(11) . . ?
C31 C32 H32 120.8 . . ?
C33 C32 C31 118.39(11) . . ?
C33 C32 H32 120.8 . . ?
C32 C33 H33 119.3 . . ?
C32 C33 C34 121.48(11) . . ?
C34 C33 H33 119.3 . . ?
C33 C34 C37 123.23(11) . . ?
C35 C34 C33 117.93(11) . . ?
C35 C34 C37 118.84(11) . . ?
C34 C35 H35 119.2 . . ?
C36 C35 C34 121.57(11) . . ?
C36 C35 H35 119.2 . . ?
C31 C36 H36 120.6 . . ?
C35 C36 C31 118.81(11) . . ?
C35 C36 H36 120.6 . . ?
C34 C37 H37 117.4 . . ?
C38 C37 C34 125.20(11) . . ?
C38 C37 H37 117.4 . . ?
C37 C38 H38 116.3 . . ?
C37 C38 C39 127.37(11) . . ?
C39 C38 H38 116.3 . . ?
C40 C39 C38 117.89(10) . . ?
C40 C39 C44 117.69(10) . . ?
C44 C39 C38 124.41(11) . . ?
C39 C40 H40 119.2 . . ?
C41 C40 C39 121.60(10) . . ?
C41 C40 H40 119.2 . . ?
C40 C41 H41 120.1 . . ?
C40 C41 C42 119.86(10) . . ?
C42 C41 H41 120.1 . . ?
O9 C42 C41 115.18(10) . . ?
O9 C42 C43 124.91(10) . . ?
C43 C42 C41 119.90(10) . . ?
C42 C43 H43 120.2 . . ?
C44 C43 C42 119.53(10) . . ?
C44 C43 H43 120.2 . . ?
C39 C44 H44 119.3 . . ?
C43 C44 C39 121.43(10) . . ?
C43 C44 H44 119.3 . . ?
O9 C45 H45A 109.5 . . ?
O9 C45 H45B 109.5 . . ?
O9 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C11 H11 O5 0.93 2.57 3.3246(15) 138.6 1_766 yes
C20 H20 O3 0.93 2.53 3.4575(14) 173.6 2_777 yes
C21 H21 O2 0.93 2.54 3.4613(15) 168.8 2_666 yes
C35 H35 O6 0.93 2.55 3.3466(15) 144.3 1_444 yes
C41 H41 O9 0.93 2.49 3.3870(14) 162.0 2_354 yes

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 N1 C1 C2 3.06(15) . . . . ?
O1 N1 C1 C6 -176.74(10) . . . . ?
O2 N1 C1 C2 -177.27(10) . . . . ?
O2 N1 C1 C6 2.92(15) . . . . ?
O3 C12 C13 C14 179.63(10) . . . . ?
N1 C1 C2 C3 -179.59(9) . . . . ?
N1 C1 C6 C5 -179.77(9) . . . . ?
C1 C2 C3 C4 -0.38(16) . . . . ?
C2 C1 C6 C5 0.43(17) . . . . ?
C2 C3 C4 C5 -0.10(16) . . . . ?
C2 C3 C4 C7 -179.93(10) . . . . ?
C3 C4 C5 C6 0.77(16) . . . . ?
C3 C4 C7 C8 -2.18(17) . . . . ?
C4 C5 C6 C1 -0.93(17) . . . . ?
C4 C7 C8 C9 -179.98(10) . . . . ?
C5 C4 C7 C8 177.99(11) . . . . ?
C6 C1 C2 C3 0.21(17) . . . . ?
C7 C4 C5 C6 -179.39(10) . . . . ?
C7 C8 C9 C10 -178.21(11) . . . . ?
C7 C8 C9 C14 2.10(18) . . . . ?
C8 C9 C10 C11 179.64(10) . . . . ?
C8 C9 C14 C13 -179.69(10) . . . . ?
C9 C10 C11 C12 -0.02(16) . . . . ?
C10 C9 C14 C13 0.61(16) . . . . ?
C10 C11 C12 O3 -179.72(10) . . . . ?
C10 C11 C12 C13 0.76(16) . . . . ?
C11 C12 C13 C14 -0.81(17) . . . . ?
C12 C13 C14 C9 0.11(17) . . . . ?
C14 C9 C10 C11 -0.66(16) . . . . ?
C15 O3 C12 C11 0.03(16) . . . . ?
C15 O3 C12 C13 179.57(10) . . . . ?
O4 N2 C16 C17 15.39(14) . . . . ?
O4 N2 C16 C21 -163.50(10) . . . . ?
O5 N2 C16 C17 -165.56(10) . . . . ?
O5 N2 C16 C21 15.56(15) . . . . ?
O6 C27 C28 C29 179.50(10) . . . . ?
N2 C16 C17 C18 -177.18(9) . . . . ?
N2 C16 C21 C20 176.70(9) . . . . ?
C16 C17 C18 C19 0.83(16) . . . . ?
C17 C16 C21 C20 -2.14(16) . . . . ?
C17 C18 C19 C20 -2.72(16) . . . . ?
C17 C18 C19 C22 177.23(10) . . . . ?
C18 C19 C20 C21 2.24(16) . . . . ?
C18 C19 C22 C23 -10.39(17) . . . . ?
C19 C20 C21 C16 0.12(16) . . . . ?
C19 C22 C23 C24 179.87(10) . . . . ?
C20 C19 C22 C23 169.56(11) . . . . ?
C21 C16 C17 C18 1.68(16) . . . . ?
C22 C19 C20 C21 -177.71(10) . . . . ?
C22 C23 C24 C25 179.40(11) . . . . ?
C22 C23 C24 C29 -0.23(18) . . . . ?
C23 C24 C25 C26 179.43(10) . . . . ?
C23 C24 C29 C28 -179.61(10) . . . . ?
C24 C25 C26 C27 0.31(17) . . . . ?
C25 C24 C29 C28 0.75(16) . . . . ?
C25 C26 C27 O6 -179.64(10) . . . . ?
C25 C26 C27 C28 0.47(16) . . . . ?
C26 C27 C28 C29 -0.63(16) . . . . ?
C27 C28 C29 C24 0.00(16) . . . . ?
C29 C24 C25 C26 -0.91(16) . . . . ?
C30 O6 C27 C26 -178.16(10) . . . . ?
C30 O6 C27 C28 1.72(16) . . . . ?
O7 N3 C31 C32 173.31(10) . . . . ?
O7 N3 C31 C36 -4.93(15) . . . . ?
O8 N3 C31 C32 -5.66(15) . . . . ?
O8 N3 C31 C36 176.10(10) . . . . ?
O9 C42 C43 C44 178.14(10) . . . . ?
N3 C31 C32 C33 -177.23(9) . . . . ?
N3 C31 C36 C35 178.01(9) . . . . ?
C31 C32 C33 C34 -0.74(17) . . . . ?
C32 C31 C36 C35 -0.18(16) . . . . ?
C32 C33 C34 C35 -0.24(16) . . . . ?
C32 C33 C34 C37 -179.58(10) . . . . ?
C33 C34 C35 C36 1.06(16) . . . . ?
C33 C34 C37 C38 -0.71(18) . . . . ?
C34 C35 C36 C31 -0.86(16) . . . . ?
C34 C37 C38 C39 -179.79(10) . . . . ?
C35 C34 C37 C38 179.96(11) . . . . ?
C36 C31 C32 C33 0.96(16) . . . . ?
C37 C34 C35 C36 -179.57(10) . . . . ?
C37 C38 C39 C40 176.42(11) . . . . ?
C37 C38 C39 C44 -2.32(19) . . . . ?
C38 C39 C40 C41 -178.98(10) . . . . ?
C38 C39 C44 C43 178.67(10) . . . . ?
C39 C40 C41 C42 0.06(17) . . . . ?
C40 C39 C44 C43 -0.08(16) . . . . ?
C40 C41 C42 O9 -178.49(9) . . . . ?
C40 C41 C42 C43 0.25(16) . . . . ?
C41 C42 C43 C44 -0.47(16) . . . . ?
C42 C43 C44 C39 0.39(17) . . . . ?
C44 C39 C40 C41 -0.15(16) . . . . ?
C45 O9 C42 C41 -178.10(10) . . . . ?
C45 O9 C42 C43 3.22(15) . . . . ?


_ins_header                      
;
TITL jk1903_a in P-1 
REM P-1 (#2 in standard setting)
CELL 1.54184  11.672032  11.817150  14.790987 109.5282 103.3892  90.9488
ZERR    5.00   0.000164   0.000186   0.000208   0.0014   0.0012   0.0012
LATT  1
SFAC C H N O
UNIT 75.00 65.00 5.00 15.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.803
