##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     SHELXL97
_journal_date_recd_electronic     2013-05-04
_journal_date_accepted     2013-05-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      7
_journal_page_first     o1053
_journal_page_last     o1054
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813014530
_journal_coeditor_code     LD2104
_publ_contact_author_name     'K. Sethusankar'
_publ_contact_author_address
;
Department of Physics
RKM Vivekananda College (Autonomous)
Chennai 600 004
India
;
_publ_contact_author_email     ksethusankar@yahoo.co.in
_publ_contact_author_fax     '044 091 2499 3057'
_publ_contact_author_phone     '044 091 24484170'
_publ_section_title
;\
<i>rac</i>-4-(4-Chlorophenyl)-2-methylamino-3-nitro-5,6,7,8-tetrahydro-\
4<i>H</i>-chromen-5-one
;
loop_
    _publ_author_name
    _publ_author_address
    'P. Narayanan'
;
Department of Physics
RKM Vivekananda College (Autonomous)
Chennai 600 004
India
;
    'Jayabal Kamalraja'
;
Organic Chemistry Division
Central Leather Research Institute
Adyar
Chennai 600 020
India
;
    'Paramasivam T. Perumal'
;
Organic Chemistry Division
Central Leather Research Institute
Adyar
Chennai 600 020
India
;
    'K. Sethusankar'
;
Department of Physics
RKM Vivekananda College (Autonomous)
Chennai 600 004
India
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;\
<i>rac</i>-4-(4-Chlorophenyl)-2-methylamino-3-nitro-5,6,7,8-\
tetrahydro-4<i>H</i>-chromen-5-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H15 Cl N2 O4'
_chemical_formula_sum     'C16 H15 Cl N2 O4'
_chemical_formula_iupac     'C16 H15 Cl N2 O4'
_chemical_formula_weight     334.75
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     8.0285(4)
_cell_length_b     10.8460(5)
_cell_length_c     18.2337(9)
_cell_angle_alpha     90.00
_cell_angle_beta     94.067(2)
_cell_angle_gamma     90.00
_cell_volume     1583.74(13)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2208
_cell_measurement_theta_min     2.19
_cell_measurement_theta_max     25.00
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.404
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     696
_exptl_absorpt_coefficient_mu     0.263
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.912
_exptl_absorpt_correction_T_max     0.924
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEXII CCD'
_diffrn_measurement_method     '\w and \f scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11848
_diffrn_reflns_av_R_equivalents     0.0290
_diffrn_reflns_av_sigmaI/netI     0.0235
_diffrn_reflns_theta_min     2.19
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>-factors based on ALL data will be
even larger.
;
_reflns_number_total     2786
_reflns_number_gt     2208
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0586
_refine_ls_R_factor_gt     0.0424
_refine_ls_wR_factor_gt     0.1054
_refine_ls_wR_factor_ref     0.1189
_refine_ls_goodness_of_fit_ref     1.085
_refine_ls_restrained_S_all     1.085
_refine_ls_number_reflns     2786
_refine_ls_number_parameters     218
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.9511P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.324
_refine_diff_density_min     -0.279
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'APEX2 (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.8013(3) 0.7871(2) 0.15451(11) 0.0393(5) Uani d . 1 1 . .
    H H1 0.8934 0.7510 0.1798 0.047 Uiso calc R 1 1 . .
    C C2 0.7070(3) 0.8723(2) 0.19018(12) 0.0440(5) Uani d . 1 1 . .
    H H2 0.7358 0.8944 0.2387 0.053 Uiso calc R 1 1 . .
    C C3 0.5699(3) 0.9234(2) 0.15224(13) 0.0443(5) Uani d . 1 1 . .
    C C4 0.5244(3) 0.8923(2) 0.08060(13) 0.0426(5) Uani d . 1 1 . .
    H H4 0.4302 0.9271 0.0561 0.051 Uiso calc R 1 1 . .
    C C5 0.6215(2) 0.80814(19) 0.04556(11) 0.0359(5) Uani d . 1 1 . .
    H H5 0.5927 0.7870 -0.0031 0.043 Uiso calc R 1 1 . .
    C C6 0.7614(2) 0.75474(18) 0.08203(11) 0.0321(4) Uani d . 1 1 . .
    C C7 0.8702(2) 0.66430(18) 0.04219(11) 0.0333(5) Uani d . 1 1 . .
    H H7 0.9648 0.6402 0.0761 0.040 Uiso calc R 1 1 . .
    C C8 0.9376(2) 0.72565(18) -0.02368(11) 0.0340(5) Uani d . 1 1 . .
    C C9 1.0653(3) 0.8231(2) -0.01071(13) 0.0408(5) Uani d . 1 1 A .
    C C10 1.1262(3) 0.8872(2) -0.07623(15) 0.0568(7) Uani d D 1 1 . .
    H H10A 1.1514 0.9722 -0.0631 0.068 Uiso calc PR 0.787(5) 1 A 1
    H H10B 1.2293 0.8485 -0.0888 0.068 Uiso calc PR 0.787(5) 1 A 1
    H H10C 1.0732 0.9676 -0.0794 0.068 Uiso calc PR 0.213(5) 1 B 2
    H H10D 1.2450 0.9012 -0.0664 0.068 Uiso calc PR 0.213(5) 1 B 2
    C C11 1.0072(4) 0.8859(3) -0.14166(18) 0.0539(9) Uani d PD 0.787(5) 1 A 1
    H H11A 1.0619 0.9181 -0.1834 0.065 Uiso calc PR 0.787(5) 1 A 1
    H H11B 0.9140 0.9397 -0.1331 0.065 Uiso calc PR 0.787(5) 1 A 1
    C C11' 1.1015(14) 0.8288(11) -0.1501(5) 0.0539(9) Uani d PD 0.213(5) 1 A 2
    H H11C 1.1949 0.7744 -0.1572 0.065 Uiso calc PR 0.213(5) 1 B 2
    H H11D 1.1009 0.8925 -0.1874 0.065 Uiso calc PR 0.213(5) 1 B 2
    C C12 0.9406(3) 0.7556(2) -0.16027(13) 0.0488(6) Uani d D 1 1 . .
    H H12A 0.8457 0.7608 -0.1962 0.059 Uiso calc PR 0.787(5) 1 A 1
    H H12B 1.0268 0.7070 -0.1813 0.059 Uiso calc PR 0.787(5) 1 A 1
    H H12C 0.9528 0.6925 -0.1972 0.059 Uiso d PR 0.213(5) 1 B 2
    H H12D 0.8519 0.8105 -0.1787 0.059 Uiso d PR 0.213(5) 1 B 2
    C C13 0.8893(3) 0.69552(19) -0.09213(11) 0.0360(5) Uani d . 1 1 A .
    C C14 0.7355(2) 0.52214(18) -0.05564(11) 0.0344(5) Uani d . 1 1 A .
    C C15 0.7772(2) 0.54932(18) 0.01722(11) 0.0329(5) Uani d . 1 1 . .
    C C16 0.6240(4) 0.3970(3) -0.15987(14) 0.0699(9) Uani d . 1 1 . .
    H H16A 0.5475 0.4562 -0.1823 0.105 Uiso calc R 1 1 . .
    H H16B 0.5771 0.3158 -0.1655 0.105 Uiso calc R 1 1 . .
    H H16C 0.7275 0.4004 -0.1831 0.105 Uiso calc R 1 1 . .
    N N1 0.7340(2) 0.46946(16) 0.07175(10) 0.0408(4) Uani d . 1 1 . .
    N N2 0.6539(2) 0.42483(17) -0.08263(10) 0.0442(5) Uani d D 1 1 . .
    O O1 0.77966(19) 0.59923(14) -0.10937(8) 0.0436(4) Uani d . 1 1 . .
    O O2 1.1201(2) 0.84650(17) 0.05139(10) 0.0574(5) Uani d . 1 1 . .
    O O3 0.6480(2) 0.37405(14) 0.05646(9) 0.0529(4) Uani d . 1 1 . .
    O O4 0.7809(3) 0.49375(16) 0.13643(9) 0.0593(5) Uani d . 1 1 . .
    Cl Cl1 0.45353(11) 1.03329(9) 0.19602(5) 0.0864(3) Uani d . 1 1 . .
    H H2A 0.621(3) 0.377(2) -0.0458(10) 0.058(8) Uiso d D 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.0421(12) 0.0421(12) 0.0334(11) -0.0032(10) 0.0014(9) 0.0005(9)
    C2 0.0523(13) 0.0468(13) 0.0341(12) -0.0107(11) 0.0099(10) -0.0078(10)
    C3 0.0439(12) 0.0403(12) 0.0510(14) -0.0058(10) 0.0186(10) -0.0095(11)
    C4 0.0342(11) 0.0407(12) 0.0533(14) -0.0023(9) 0.0048(10) 0.0005(10)
    C5 0.0362(11) 0.0359(11) 0.0354(11) -0.0074(9) 0.0023(8) -0.0038(9)
    C6 0.0334(10) 0.0292(10) 0.0342(11) -0.0072(8) 0.0056(8) -0.0008(8)
    C7 0.0329(10) 0.0325(11) 0.0342(11) -0.0016(8) -0.0002(8) 0.0004(9)
    C8 0.0325(10) 0.0301(11) 0.0401(12) -0.0018(8) 0.0065(8) -0.0025(9)
    C9 0.0336(11) 0.0371(12) 0.0520(14) -0.0031(9) 0.0066(10) -0.0091(10)
    C10 0.0599(15) 0.0415(14) 0.0707(17) -0.0169(12) 0.0173(13) -0.0015(12)
    C11 0.062(2) 0.0432(19) 0.0571(19) -0.0125(14) 0.0095(16) 0.0095(15)
    C11' 0.062(2) 0.0432(19) 0.0571(19) -0.0125(14) 0.0095(16) 0.0095(15)
    C12 0.0615(15) 0.0446(13) 0.0417(13) -0.0119(11) 0.0136(11) 0.0021(10)
    C13 0.0379(11) 0.0303(11) 0.0405(12) -0.0044(9) 0.0084(9) -0.0011(9)
    C14 0.0345(10) 0.0297(10) 0.0399(12) -0.0027(8) 0.0081(8) -0.0001(9)
    C15 0.0360(10) 0.0271(10) 0.0358(11) -0.0005(8) 0.0044(8) 0.0014(8)
    C16 0.087(2) 0.076(2) 0.0483(16) -0.0372(16) 0.0119(14) -0.0187(14)
    N1 0.0514(11) 0.0311(10) 0.0404(11) 0.0013(8) 0.0063(8) 0.0047(8)
    N2 0.0542(11) 0.0378(11) 0.0416(11) -0.0144(9) 0.0102(9) -0.0070(9)
    O1 0.0555(9) 0.0415(9) 0.0341(8) -0.0178(7) 0.0051(7) -0.0012(7)
    O2 0.0482(10) 0.0634(11) 0.0606(12) -0.0179(8) 0.0035(8) -0.0148(9)
    O3 0.0695(11) 0.0331(9) 0.0572(11) -0.0129(8) 0.0109(8) 0.0050(7)
    O4 0.0923(14) 0.0494(10) 0.0353(10) -0.0065(9) -0.0008(9) 0.0095(8)
    Cl1 0.0797(5) 0.0901(6) 0.0916(6) 0.0240(4) 0.0224(4) -0.0350(5)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C6 . 1.383(3) ?
    C1 C2 . 1.386(3) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.375(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.373(3) ?
    C3 Cl1 . 1.742(2) ?
    C4 C5 . 1.386(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.390(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.531(3) ?
    C7 C8 . 1.507(3) ?
    C7 C15 . 1.507(3) ?
    C7 H7 . 0.9800 ?
    C8 C13 . 1.321(3) ?
    C8 C9 . 1.480(3) ?
    C9 O2 . 1.212(3) ?
    C9 C10 . 1.494(3) ?
    C10 C11 . 1.475(4) ?
    C10 C11' . 1.489(8) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C10 H10C . 0.9700 ?
    C10 H10D . 0.9700 ?
    C11 C12 . 1.540(4) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C11' C12 . 1.516(8) ?
    C11' H11C . 0.9700 ?
    C11' H11D . 0.9700 ?
    C12 C13 . 1.487(3) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C12 H12C . 0.9700 ?
    C12 H12D . 0.9700 ?
    C13 O1 . 1.387(2) ?
    C14 N2 . 1.319(3) ?
    C14 O1 . 1.354(2) ?
    C14 C15 . 1.379(3) ?
    C15 N1 . 1.381(3) ?
    C16 N2 . 1.444(3) ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
    N1 O4 . 1.241(2) ?
    N1 O3 . 1.264(2) ?
    N2 H2A . 0.901(10) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C6 C1 C2 . . 121.4(2) ?
    C6 C1 H1 . . 119.3 ?
    C2 C1 H1 . . 119.3 ?
    C3 C2 C1 . . 118.5(2) ?
    C3 C2 H2 . . 120.7 ?
    C1 C2 H2 . . 120.7 ?
    C4 C3 C2 . . 122.0(2) ?
    C4 C3 Cl1 . . 119.25(19) ?
    C2 C3 Cl1 . . 118.77(18) ?
    C3 C4 C5 . . 118.7(2) ?
    C3 C4 H4 . . 120.7 ?
    C5 C4 H4 . . 120.7 ?
    C4 C5 C6 . . 121.05(19) ?
    C4 C5 H5 . . 119.5 ?
    C6 C5 H5 . . 119.5 ?
    C1 C6 C5 . . 118.42(19) ?
    C1 C6 C7 . . 120.98(18) ?
    C5 C6 C7 . . 120.58(17) ?
    C8 C7 C15 . . 108.83(16) ?
    C8 C7 C6 . . 110.16(16) ?
    C15 C7 C6 . . 112.73(16) ?
    C8 C7 H7 . . 108.3 ?
    C15 C7 H7 . . 108.3 ?
    C6 C7 H7 . . 108.3 ?
    C13 C8 C9 . . 118.77(19) ?
    C13 C8 C7 . . 123.07(18) ?
    C9 C8 C7 . . 118.15(18) ?
    O2 C9 C8 . . 120.0(2) ?
    O2 C9 C10 . . 122.1(2) ?
    C8 C9 C10 . . 117.8(2) ?
    C11 C10 C9 . . 114.4(2) ?
    C11' C10 C9 . . 119.7(4) ?
    C11 C10 H10A . . 108.7 ?
    C11' C10 H10A . . 129.7 ?
    C9 C10 H10A . . 108.7 ?
    C11 C10 H10B . . 108.7 ?
    C11' C10 H10B . . 70.3 ?
    C9 C10 H10B . . 108.7 ?
    H10A C10 H10B . . 107.6 ?
    C11 C10 H10C . . 72.8 ?
    C11' C10 H10C . . 107.4 ?
    C9 C10 H10C . . 107.4 ?
    H10B C10 H10C . . 138.8 ?
    C11 C10 H10D . . 136.3 ?
    C11' C10 H10D . . 107.4 ?
    C9 C10 H10D . . 107.4 ?
    H10A C10 H10D . . 67.7 ?
    H10C C10 H10D . . 106.9 ?
    C10 C11 C12 . . 112.5(2) ?
    C10 C11 H11A . . 109.1 ?
    C12 C11 H11A . . 109.1 ?
    C10 C11 H11B . . 109.1 ?
    C12 C11 H11B . . 109.1 ?
    H11A C11 H11B . . 107.8 ?
    C10 C11' C12 . . 113.0(6) ?
    C10 C11' H11C . . 109.0 ?
    C12 C11' H11C . . 109.0 ?
    C10 C11' H11D . . 109.0 ?
    C12 C11' H11D . . 109.0 ?
    H11C C11' H11D . . 107.8 ?
    C13 C12 C11' . . 114.3(4) ?
    C13 C12 C11 . . 109.3(2) ?
    C13 C12 H12A . . 109.8 ?
    C11' C12 H12A . . 132.3 ?
    C11 C12 H12A . . 109.8 ?
    C13 C12 H12B . . 109.8 ?
    C11' C12 H12B . . 72.9 ?
    C11 C12 H12B . . 109.8 ?
    H12A C12 H12B . . 108.3 ?
    C13 C12 H12C . . 108.6 ?
    C11' C12 H12C . . 109.1 ?
    C11 C12 H12C . . 138.6 ?
    H12A C12 H12C . . 71.7 ?
    C13 C12 H12D . . 108.6 ?
    C11' C12 H12D . . 108.6 ?
    C11 C12 H12D . . 75.4 ?
    H12B C12 H12D . . 136.4 ?
    H12C C12 H12D . . 107.5 ?
    C8 C13 O1 . . 122.63(18) ?
    C8 C13 C12 . . 126.9(2) ?
    O1 C13 C12 . . 110.45(18) ?
    N2 C14 O1 . . 111.88(18) ?
    N2 C14 C15 . . 127.66(19) ?
    O1 C14 C15 . . 120.45(18) ?
    C14 C15 N1 . . 120.21(18) ?
    C14 C15 C7 . . 123.32(18) ?
    N1 C15 C7 . . 116.47(17) ?
    N2 C16 H16A . . 109.5 ?
    N2 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    N2 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    O4 N1 O3 . . 120.52(18) ?
    O4 N1 C15 . . 118.43(18) ?
    O3 N1 C15 . . 121.05(18) ?
    C14 N2 C16 . . 125.1(2) ?
    C14 N2 H2A . . 110.2(17) ?
    C16 N2 H2A . . 124.7(17) ?
    C14 O1 C13 . . 119.69(16) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C3 . . . . 0.9(3) ?
    C1 C2 C3 C4 . . . . 0.1(3) ?
    C1 C2 C3 Cl1 . . . . -178.49(17) ?
    C2 C3 C4 C5 . . . . -0.9(3) ?
    Cl1 C3 C4 C5 . . . . 177.67(16) ?
    C3 C4 C5 C6 . . . . 0.7(3) ?
    C2 C1 C6 C5 . . . . -1.1(3) ?
    C2 C1 C6 C7 . . . . 177.64(19) ?
    C4 C5 C6 C1 . . . . 0.3(3) ?
    C4 C5 C6 C7 . . . . -178.48(18) ?
    C1 C6 C7 C8 . . . . -119.8(2) ?
    C5 C6 C7 C8 . . . . 58.9(2) ?
    C1 C6 C7 C15 . . . . 118.4(2) ?
    C5 C6 C7 C15 . . . . -62.8(2) ?
    C15 C7 C8 C13 . . . . 13.3(3) ?
    C6 C7 C8 C13 . . . . -110.8(2) ?
    C15 C7 C8 C9 . . . . -166.00(17) ?
    C6 C7 C8 C9 . . . . 69.9(2) ?
    C13 C8 C9 O2 . . . . -174.9(2) ?
    C7 C8 C9 O2 . . . . 4.4(3) ?
    C13 C8 C9 C10 . . . . 3.3(3) ?
    C7 C8 C9 C10 . . . . -177.4(2) ?
    O2 C9 C10 C11 . . . . -156.9(3) ?
    C8 C9 C10 C11 . . . . 24.9(3) ?
    O2 C9 C10 C11' . . . . 159.0(6) ?
    C8 C9 C10 C11' . . . . -19.1(7) ?
    C11' C10 C11 C12 . . . . 57.4(6) ?
    C9 C10 C11 C12 . . . . -50.4(4) ?
    C11 C10 C11' C12 . . . . -59.2(7) ?
    C9 C10 C11' C12 . . . . 33.9(11) ?
    C10 C11' C12 C13 . . . . -33.1(11) ?
    C10 C11' C12 C11 . . . . 57.6(6) ?
    C10 C11 C12 C13 . . . . 46.9(3) ?
    C10 C11 C12 C11' . . . . -58.2(6) ?
    C9 C8 C13 O1 . . . . 175.11(18) ?
    C7 C8 C13 O1 . . . . -4.1(3) ?
    C9 C8 C13 C12 . . . . -4.8(3) ?
    C7 C8 C13 C12 . . . . 176.0(2) ?
    C11' C12 C13 C8 . . . . 20.5(7) ?
    C11 C12 C13 C8 . . . . -20.3(3) ?
    C11' C12 C13 O1 . . . . -159.3(6) ?
    C11 C12 C13 O1 . . . . 159.8(2) ?
    N2 C14 C15 N1 . . . . 0.5(3) ?
    O1 C14 C15 N1 . . . . -179.05(18) ?
    N2 C14 C15 C7 . . . . -179.6(2) ?
    O1 C14 C15 C7 . . . . 0.9(3) ?
    C8 C7 C15 C14 . . . . -11.7(3) ?
    C6 C7 C15 C14 . . . . 110.8(2) ?
    C8 C7 C15 N1 . . . . 168.27(17) ?
    C6 C7 C15 N1 . . . . -69.2(2) ?
    C14 C15 N1 O4 . . . . 176.39(19) ?
    C7 C15 N1 O4 . . . . -3.6(3) ?
    C14 C15 N1 O3 . . . . -3.9(3) ?
    C7 C15 N1 O3 . . . . 176.11(18) ?
    O1 C14 N2 C16 . . . . 4.2(3) ?
    C15 C14 N2 C16 . . . . -175.4(2) ?
    N2 C14 O1 C13 . . . . -169.49(18) ?
    C15 C14 O1 C13 . . . . 10.1(3) ?
    C8 C13 O1 C14 . . . . -8.7(3) ?
    C12 C13 O1 C14 . . . . 171.21(19) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N2 H2A O3 . 0.90(2) 1.862(18) 2.599(2) 137.3(19)
    C2 H2 O4 2_655 0.93 2.53 3.420(3) 160.0
    C10 H10A Cg1 3_775 0.97 2.75 3.515(2) 136.0
    C16 H16B Cg1 3_665 0.96 2.76 3.577(3) 144.0
_iucr_refine_instructions_details
;
TITL JKR138 in P2(1)/n
CELL  0.71073   8.0285  10.8460  18.2337   90.000   94.067   90.000
ZERR     4.00   0.0004   0.0005   0.0009    0.000    0.002    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O    CL
UNIT  64   60   8    16   4
MERG   2
SUMP 1.0 0.001 1. 2. 1. 3.
SADI 0.01 C10 C11 C10 C11'
SADI 0.01 C12 C11 C12 C11'
EADP C11 C11'
DFIX 0.90 0.01 N2 H2A
FMAP   2
PLAN   20
OMIT -2 50
SIZE     0.30   0.30   0.35
ACTA
BOND   $H
CONF
L.S.  15
WGHT      0.0482      0.9511
FVAR       0.15980   0.78682   0.21305
C1    1    0.801312    0.787131    0.154509    11.00000    0.04208    0.04214 =
         0.03337    0.00045    0.00139   -0.00319
AFIX  43
H1    2    0.893397    0.750999    0.179830    11.00000   -1.20000
AFIX   0
C2    1    0.706970    0.872292    0.190181    11.00000    0.05226    0.04678 =
         0.03408   -0.00782    0.00990   -0.01069
AFIX  43
H2    2    0.735757    0.894378    0.238714    11.00000   -1.20000
AFIX   0
C3    1    0.569881    0.923402    0.152236    11.00000    0.04388    0.04027 =
         0.05105   -0.00946    0.01857   -0.00577
C4    1    0.524368    0.892335    0.080604    11.00000    0.03418    0.04070 =
         0.05330    0.00048    0.00479   -0.00228
AFIX  43
H4    2    0.430245    0.927078    0.056090    11.00000   -1.20000
AFIX   0
C5    1    0.621549    0.808137    0.045560    11.00000    0.03623    0.03593 =
         0.03539   -0.00384    0.00234   -0.00742
AFIX  43
H5    2    0.592724    0.787036   -0.003128    11.00000   -1.20000
AFIX   0
C6    1    0.761384    0.754745    0.082029    11.00000    0.03341    0.02916 =
         0.03425   -0.00079    0.00560   -0.00717
C7    1    0.870214    0.664303    0.042191    11.00000    0.03287    0.03251 =
         0.03421    0.00041   -0.00023   -0.00162
AFIX  13
H7    2    0.964791    0.640177    0.076085    11.00000   -1.20000
AFIX   0
C8    1    0.937608    0.725646   -0.023681    11.00000    0.03249    0.03007 =
         0.04007   -0.00247    0.00651   -0.00177
C9    1    1.065305    0.823099   -0.010707    11.00000    0.03365    0.03710 =
         0.05204   -0.00909    0.00658   -0.00310
C10   1    1.126185    0.887206   -0.076228    11.00000    0.05995    0.04155 =
         0.07072   -0.00149    0.01729   -0.01691
PART    1
AFIX  23
H10A  2    1.151419    0.972201   -0.063147    21.00000   -1.20000
H10B  2    1.229314    0.848496   -0.088765    21.00000   -1.20000
AFIX  23
PART    2
H10C  2    1.073228    0.967599   -0.079394    31.00000   -1.20000
H10D  2    1.245013    0.901213   -0.066443    31.00000   -1.20000
AFIX   0
PART    1
C11   1    1.007165    0.885897   -0.141659    21.00000    0.06222    0.04325 =
         0.05709    0.00955    0.00948   -0.01249
AFIX  23
H11A  2    1.061877    0.918130   -0.183367    21.00000   -1.20000
H11B  2    0.913965    0.939679   -0.133122    21.00000   -1.20000
AFIX   0
PART    2
C11'  1    1.101508    0.828777   -0.150109    31.00000    0.06222    0.04325 =
         0.05709    0.00955    0.00948   -0.01249
AFIX  23
H11C  2    1.194884    0.774362   -0.157217    31.00000   -1.20000
H11D  2    1.100904    0.892516   -0.187444    31.00000   -1.20000
AFIX   0
PART    0
C12   1    0.940557    0.755628   -0.160275    11.00000    0.06150    0.04461 =
         0.04169    0.00207    0.01357   -0.01186
PART    1
AFIX  23
H12A  2    0.845722    0.760833   -0.196184    21.00000   -1.20000
H12B  2    1.026779    0.707036   -0.181259    21.00000   -1.20000
PART    2
H12C  2    0.952846    0.692502   -0.197186    31.00000   -1.20000
H12D  2    0.851860    0.810549   -0.178705    31.00000   -1.20000
AFIX   0
PART    0
C13   1    0.889284    0.695523   -0.092125    11.00000    0.03793    0.03035 =
         0.04047   -0.00113    0.00844   -0.00436
C14   1    0.735477    0.522143   -0.055636    11.00000    0.03450    0.02968 =
         0.03992   -0.00011    0.00814   -0.00274
C15   1    0.777216    0.549317    0.017217    11.00000    0.03598    0.02714 =
         0.03579    0.00137    0.00438   -0.00047
C16   1    0.623988    0.396967   -0.159872    11.00000    0.08662    0.07571 =
         0.04833   -0.01869    0.01189   -0.03716
AFIX 137
H16A  2    0.547735    0.456309   -0.182362    11.00000   -1.50000
H16B  2    0.576795    0.315905   -0.165516    11.00000   -1.50000
H16C  2    0.727538    0.400163   -0.183097    11.00000   -1.50000
AFIX   0
N1    3    0.733972    0.469459    0.071749    11.00000    0.05136    0.03108 =
         0.04038    0.00472    0.00630    0.00126
N2    3    0.653916    0.424827   -0.082625    11.00000    0.05417    0.03781 =
         0.04157   -0.00697    0.01015   -0.01443
O1    4    0.779660    0.599230   -0.109371    11.00000    0.05548    0.04145 =
         0.03406   -0.00116    0.00511   -0.01777
O2    4    1.120078    0.846496    0.051393    11.00000    0.04817    0.06339 =
         0.06059   -0.01478    0.00353   -0.01794
O3    4    0.647972    0.374051    0.056458    11.00000    0.06950    0.03311 =
         0.05716    0.00504    0.01094   -0.01295
O4    4    0.780925    0.493755    0.136435    11.00000    0.09228    0.04943 =
         0.03529    0.00954   -0.00079   -0.00650
CL1   5    0.453534    1.033288    0.196023    11.00000    0.07974    0.09006 =
         0.09162   -0.03498    0.02240    0.02398
H2A   2    0.620540    0.377399   -0.045839    11.00000    0.05830
HKLF 4
;