
data_RK_a

_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C19 H16 Cl N5 O7'
_chemical_formula_sum
 'C19 H16 Cl N5 O7'
_chemical_formula_weight          461.82

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                    14.972(5)
_cell_length_b                    8.905(5)
_cell_length_c                    15.738(3)
_cell_angle_alpha                 90
_cell_angle_beta                  95.65(2)
_cell_angle_gamma                 90
_cell_volume                      2088.1(14)
_cell_formula_units_Z             4
_cell_measurement_temperature     298(2)

_cell_measurement_reflns_used     25

_cell_measurement_theta_min       11.19

_cell_measurement_theta_max       14.39


_exptl_crystal_description        prismatic

_exptl_crystal_colour             orange

_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.469
_exptl_crystal_F_000              952
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200

_exptl_crystal_size_mid           0.100

_exptl_crystal_size_min           0.100

_exptl_absorpt_coefficient_mu     0.236
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    none

_exptl_absorpt_correction_T_min   ?

_exptl_absorpt_correction_T_max   ?

_exptl_absorpt_process_details    ?

_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       298(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Rigaku AFC7R'

_diffrn_measurement_method        ω-2θ

_diffrn_detector_area_resol_mean  ?

_diffrn_reflns_number             4995
_diffrn_reflns_av_unetI/netI      0.0504
_diffrn_reflns_av_R_equivalents   0.0203
_diffrn_reflns_limit_h_min        0
_diffrn_reflns_limit_h_max        19
_diffrn_reflns_limit_k_min        0
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          2.601
_diffrn_reflns_theta_max          27.496
_diffrn_reflns_theta_full         25.240
_diffrn_measured_fraction_theta_max   1.000
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    1.000
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   1.000
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              4814
_reflns_number_gt                 2788
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .

_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection        'MSC/AFC Diffractometer Control (Rigaku, 1998)'
_computing_cell_refinement        'MSC/AFC Diffractometer Control'
_computing_data_reduction         'MSC/AFC Diffractometer Control'
_computing_structure_solution     'SIR2004 (Burla, et al., 2005)'

_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details
;
    ENTER TEXT OF LETTER
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0616P)²+0.2039P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr

_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4814
_refine_ls_number_parameters      291
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1026
_refine_ls_R_factor_gt            0.0439
_refine_ls_wR_factor_ref          0.1387
_refine_ls_wR_factor_gt           0.1170
_refine_ls_goodness_of_fit_ref    1.026
_refine_ls_restrained_S_all       1.026
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000

loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.60033(11) 0.8298(2) 0.87814(10) 0.0520(4) Uani 1 1 d . . . . .
C1 C 0.52018(15) 0.8869(3) 0.83796(15) 0.0449(5) Uani 1 1 d . . . . .
H1 H 0.478753 0.913599 0.880015 0.054 Uiso 1 1 calc R U . . .
C2 C 0.47945(13) 0.7657(2) 0.77691(14) 0.0378(5) Uani 1 1 d . . . . .
H2 H 0.457592 0.810606 0.721901 0.045 Uiso 1 1 calc R U . . .
C3 C 0.56227(13) 0.6716(3) 0.76756(14) 0.0399(5) Uani 1 1 d . . . . .
C4 C 0.62654(15) 0.7117(3) 0.82839(15) 0.0461(5) Uani 1 1 d . . . . .
N1 N 0.54268(15) 1.0256(2) 0.78512(14) 0.0546(5) Uani 1 1 d . . . . .
O2 O 0.61975(14) 1.0516(2) 0.77458(14) 0.0724(6) Uani 1 1 d . . . . .
O3 O 0.47909(16) 1.0998(2) 0.75828(17) 0.0877(7) Uani 1 1 d . . . . .
C5 C 0.40432(13) 0.6785(2) 0.81326(13) 0.0379(5) Uani 1 1 d . . . . .
C6 C 0.31584(14) 0.7179(3) 0.79117(15) 0.0457(5) Uani 1 1 d . . . . .
H3 H 0.302752 0.798614 0.754548 0.055 Uiso 1 1 calc R U . . .
C7 C 0.24619(15) 0.6394(3) 0.82260(15) 0.0498(6) Uani 1 1 d . . . . .
H4 H 0.186843 0.665831 0.806446 0.060 Uiso 1 1 calc R U . . .
C8 C 0.26591(16) 0.5228(3) 0.87760(15) 0.0463(5) Uani 1 1 d . . . . .
C9 C 0.35292(18) 0.4810(3) 0.90149(17) 0.0577(7) Uani 1 1 d . . . . .
H5 H 0.365398 0.401250 0.938931 0.069 Uiso 1 1 calc R U . . .
C10 C 0.42224(16) 0.5596(3) 0.86896(17) 0.0536(6) Uani 1 1 d . . . . .
H6 H 0.481426 0.531879 0.884841 0.064 Uiso 1 1 calc R U . . .
Cl1 Cl 0.17834(4) 0.42618(8) 0.91904(4) 0.0620(2) Uani 1 1 d . . . . .
C12 C 0.63723(18) 0.4507(3) 0.69444(18) 0.0611(7) Uani 1 1 d . . . . .
H7 H 0.626263 0.355255 0.719757 0.092 Uiso 1 1 calc R U . . .
H8 H 0.690897 0.494058 0.722674 0.092 Uiso 1 1 calc R U . . .
H9 H 0.644371 0.437185 0.634970 0.092 Uiso 1 1 calc R U . . .
C11 C 0.55923(14) 0.5536(3) 0.70369(14) 0.0423(5) Uani 1 1 d . . . . .
N2 N 0.48280(13) 0.5435(2) 0.65813(12) 0.0451(4) Uani 1 1 d . . . . .
N3 N 0.47377(14) 0.4308(2) 0.59780(12) 0.0489(5) Uani 1 1 d . . . . .
H16 H 0.519530 0.378417 0.586897 0.059 Uiso 1 1 calc R U . . .
C13 C 0.39260(16) 0.4038(2) 0.55627(14) 0.0428(5) Uani 1 1 d . . . . .
C14 C 0.37735(17) 0.2878(2) 0.49462(14) 0.0446(5) Uani 1 1 d . . . . .
C15 C 0.29270(17) 0.2536(3) 0.45852(14) 0.0469(5) Uani 1 1 d . . . . .
H10 H 0.284231 0.175676 0.419224 0.056 Uiso 1 1 calc R U . . .
C16 C 0.22069(16) 0.3345(3) 0.48049(14) 0.0467(5) Uani 1 1 d . . . . .
C17 C 0.23273(17) 0.4569(3) 0.53608(15) 0.0506(6) Uani 1 1 d . . . . .
H11 H 0.183928 0.515028 0.548078 0.061 Uiso 1 1 calc R U . . .
C18 C 0.31682(16) 0.4900(3) 0.57250(15) 0.0493(6) Uani 1 1 d . . . . .
H12 H 0.324578 0.571895 0.609164 0.059 Uiso 1 1 calc R U . . .
N4 N 0.45087(17) 0.1975(2) 0.46816(14) 0.0569(6) Uani 1 1 d . . . . .
O4 O 0.52665(14) 0.2135(2) 0.50519(14) 0.0731(6) Uani 1 1 d . . . . .
O5 O 0.43474(15) 0.1094(2) 0.40880(13) 0.0742(6) Uani 1 1 d . . . . .
N5 N 0.13072(15) 0.2883(2) 0.44857(13) 0.0538(5) Uani 1 1 d . . . . .
O6 O 0.12198(15) 0.1791(2) 0.40093(14) 0.0780(6) Uani 1 1 d . . . . .
O7 O 0.06671(13) 0.3596(2) 0.47116(12) 0.0669(5) Uani 1 1 d . . . . .
C19 C 0.71797(16) 0.6570(3) 0.8585(2) 0.0647(8) Uani 1 1 d . . . . .
H13 H 0.714854 0.553574 0.875119 0.097 Uiso 1 1 calc R U . . .
H14 H 0.741941 0.715866 0.906500 0.097 Uiso 1 1 calc R U . . .
H15 H 0.756187 0.666255 0.813217 0.097 Uiso 1 1 calc R U . . .


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

loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 C4 1.390(3) . ?
O1 C1 1.396(3) . ?
C1 C2 1.531(3) . ?
C1 N1 1.544(3) . ?
C2 C3 1.516(3) . ?
C2 C5 1.524(3) . ?
C3 C4 1.337(3) . ?
C3 C11 1.452(3) . ?
C4 C19 1.486(3) . ?
N1 O3 1.201(3) . ?
N1 O2 1.204(3) . ?
C5 C6 1.382(3) . ?
C5 C10 1.384(3) . ?
C6 C7 1.386(3) . ?
C7 C8 1.366(4) . ?
C8 C9 1.371(4) . ?
C8 Cl1 1.747(2) . ?
C9 C10 1.391(3) . ?
C12 C11 1.502(3) . ?
C11 N2 1.292(3) . ?
N2 N3 1.379(3) . ?
N3 C13 1.344(3) . ?
C13 C18 1.414(3) . ?
C13 C14 1.420(3) . ?
C14 C15 1.371(3) . ?
C14 N4 1.457(3) . ?
C15 C16 1.369(3) . ?
C16 C17 1.398(3) . ?
C16 N5 1.450(3) . ?
C17 C18 1.363(3) . ?
N4 O5 1.225(3) . ?
N4 O4 1.232(3) . ?
N5 O6 1.228(3) . ?
N5 O7 1.231(3) . ?

loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C4 O1 C1 107.34(17) . . ?
O1 C1 C2 107.41(19) . . ?
O1 C1 N1 108.18(18) . . ?
C2 C1 N1 108.67(18) . . ?
C3 C2 C5 113.29(18) . . ?
C3 C2 C1 99.87(17) . . ?
C5 C2 C1 112.76(17) . . ?
C4 C3 C11 131.3(2) . . ?
C4 C3 C2 108.7(2) . . ?
C11 C3 C2 119.82(19) . . ?
C3 C4 O1 112.4(2) . . ?
C3 C4 C19 135.7(2) . . ?
O1 C4 C19 111.8(2) . . ?
O3 N1 O2 125.6(3) . . ?
O3 N1 C1 115.0(2) . . ?
O2 N1 C1 119.4(2) . . ?
C6 C5 C10 118.4(2) . . ?
C6 C5 C2 120.0(2) . . ?
C10 C5 C2 121.58(19) . . ?
C5 C6 C7 121.2(2) . . ?
C8 C7 C6 119.1(2) . . ?
C7 C8 C9 121.4(2) . . ?
C7 C8 Cl1 119.19(19) . . ?
C9 C8 Cl1 119.5(2) . . ?
C8 C9 C10 119.1(2) . . ?
C5 C10 C9 120.9(2) . . ?
N2 C11 C3 113.59(19) . . ?
N2 C11 C12 123.9(2) . . ?
C3 C11 C12 122.5(2) . . ?
C11 N2 N3 117.01(19) . . ?
C13 N3 N2 119.20(19) . . ?
N3 C13 C18 121.2(2) . . ?
N3 C13 C14 122.6(2) . . ?
C18 C13 C14 116.1(2) . . ?
C15 C14 C13 121.6(2) . . ?
C15 C14 N4 116.9(2) . . ?
C13 C14 N4 121.4(2) . . ?
C16 C15 C14 119.8(2) . . ?
C15 C16 C17 120.8(2) . . ?
C15 C16 N5 119.4(2) . . ?
C17 C16 N5 119.7(2) . . ?
C18 C17 C16 119.3(2) . . ?
C17 C18 C13 122.1(2) . . ?
O5 N4 O4 122.6(2) . . ?
O5 N4 C14 118.3(2) . . ?
O4 N4 C14 119.2(2) . . ?
O6 N5 O7 123.1(2) . . ?
O6 N5 C16 118.4(2) . . ?
O7 N5 C16 118.5(2) . . ?

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
C4 O1 C1 C2 19.5(2) . . . . ?
C4 O1 C1 N1 -97.6(2) . . . . ?
O1 C1 C2 C3 -20.0(2) . . . . ?
N1 C1 C2 C3 96.8(2) . . . . ?
O1 C1 C2 C5 100.6(2) . . . . ?
N1 C1 C2 C5 -142.61(19) . . . . ?
C5 C2 C3 C4 -106.4(2) . . . . ?
C1 C2 C3 C4 13.7(2) . . . . ?
C5 C2 C3 C11 69.4(2) . . . . ?
C1 C2 C3 C11 -170.40(19) . . . . ?
C11 C3 C4 O1 -178.1(2) . . . . ?
C2 C3 C4 O1 -2.9(2) . . . . ?
C11 C3 C4 C19 -1.3(4) . . . . ?
C2 C3 C4 C19 173.9(3) . . . . ?
C1 O1 C4 C3 -10.8(2) . . . . ?
C1 O1 C4 C19 171.6(2) . . . . ?
O1 C1 N1 O3 -168.6(2) . . . . ?
C2 C1 N1 O3 75.1(3) . . . . ?
O1 C1 N1 O2 10.9(3) . . . . ?
C2 C1 N1 O2 -105.5(2) . . . . ?
C3 C2 C5 C6 -150.4(2) . . . . ?
C1 C2 C5 C6 97.1(2) . . . . ?
C3 C2 C5 C10 29.9(3) . . . . ?
C1 C2 C5 C10 -82.6(3) . . . . ?
C10 C5 C6 C7 -1.1(3) . . . . ?
C2 C5 C6 C7 179.3(2) . . . . ?
C5 C6 C7 C8 1.2(4) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
C6 C7 C8 Cl1 178.66(18) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
Cl1 C8 C9 C10 -179.3(2) . . . . ?
C6 C5 C10 C9 0.4(4) . . . . ?
C2 C5 C10 C9 -179.9(2) . . . . ?
C8 C9 C10 C5 0.0(4) . . . . ?
C4 C3 C11 N2 176.3(2) . . . . ?
C2 C3 C11 N2 1.6(3) . . . . ?
C4 C3 C11 C12 -1.7(4) . . . . ?
C2 C3 C11 C12 -176.5(2) . . . . ?
C3 C11 N2 N3 -178.02(18) . . . . ?
C12 C11 N2 N3 0.0(3) . . . . ?
C11 N2 N3 C13 171.8(2) . . . . ?
N2 N3 C13 C18 0.9(3) . . . . ?
N2 N3 C13 C14 -178.65(19) . . . . ?
N3 C13 C14 C15 174.2(2) . . . . ?
C18 C13 C14 C15 -5.4(3) . . . . ?
N3 C13 C14 N4 -4.5(3) . . . . ?
C18 C13 C14 N4 176.0(2) . . . . ?
C13 C14 C15 C16 1.5(3) . . . . ?
N4 C14 C15 C16 -179.8(2) . . . . ?
C14 C15 C16 C17 3.3(3) . . . . ?
C14 C15 C16 N5 -174.0(2) . . . . ?
C15 C16 C17 C18 -3.9(4) . . . . ?
N5 C16 C17 C18 173.4(2) . . . . ?
C16 C17 C18 C13 -0.4(4) . . . . ?
N3 C13 C18 C17 -174.7(2) . . . . ?
C14 C13 C18 C17 4.8(3) . . . . ?
C15 C14 N4 O5 8.4(3) . . . . ?
C13 C14 N4 O5 -172.9(2) . . . . ?
C15 C14 N4 O4 -172.5(2) . . . . ?
C13 C14 N4 O4 6.2(3) . . . . ?
C15 C16 N5 O6 -1.6(3) . . . . ?
C17 C16 N5 O6 -178.9(2) . . . . ?
C15 C16 N5 O7 177.8(2) . . . . ?
C17 C16 N5 O7 0.4(3) . . . . ?

_refine_diff_density_max    0.234
_refine_diff_density_min   -0.233
_refine_diff_density_rms    0.055



_symmetry_cell_setting            monoclinic
_diffrn_radiation_source          ?
_diffrn_radiation_monochromator   ?
_publ_section_references
;Wakita, K. (2001). Yadokari-XG. Software for Crystal Structure Analyses.
Release of Software (Yadokari-XG 2009) for Crystal Structure Analyses,
Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009).
J. Cryst. Soc.  Jpn. 51, 218-224.
;
_chemical_absolute_configuration  ?
