# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_16jlr002
_database_code_depnum_ccdc_archive 'CCDC 1976759'
loop_
_audit_author_name
_audit_author_address
'Juerg Hauser'
;University of Bern
Switzerland
;
_audit_update_record             
;
2020-01-10 deposited with the CCDC.	2020-05-07 downloaded from the CCDC.
;

_audit_creation_date             2016-09-06T14:31:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C13 H16 N4 O'
_chemical_formula_moiety         'C13 H16 N4 O'
_chemical_formula_weight         244.3

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1640(3)
_cell_length_b                   8.5511(4)
_cell_length_c                   19.8770(7)
_cell_angle_alpha                93.396(3)
_cell_angle_beta                 99.154(3)
_cell_angle_gamma                117.195(4)
_cell_volume                     1204.68(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4470
_cell_measurement_theta_min      2.085
_cell_measurement_theta_max      27.441

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             520

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.76978
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_ambient_temperature      173(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0965
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.013067
_diffrn_orient_matrix_ub_12      -0.0014783
_diffrn_orient_matrix_ub_13      0.0360541
_diffrn_orient_matrix_ub_21      0.0711968
_diffrn_orient_matrix_ub_22      -0.0250241
_diffrn_orient_matrix_ub_23      -0.0015312
_diffrn_orient_matrix_ub_31      0.0688495
_diffrn_orient_matrix_ub_32      0.0909367
_diffrn_orient_matrix_ub_33      0.0058633
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_number            16639
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.099
_diffrn_reflns_theta_max         28.259
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.912
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.912
_reflns_Friedel_coverage         0
_reflns_number_total             5444
_reflns_number_gt                3996
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0482P)²+0.4126P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5444
_refine_ls_number_parameters     354
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.6757(2) 0.4829(2) 0.92751(8) 0.0228(3) Uani 1 1 d . . . . .
C2 C 0.5723(2) 0.4948(2) 0.80783(8) 0.0315(4) Uani 1 1 d . . . . .
C3 C 0.4106(2) 0.3305(2) 0.81040(8) 0.0287(4) Uani 1 1 d . . . . .
H3 H 0.3117 0.2736 0.7708 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3977(2) 0.2554(2) 0.86884(8) 0.0243(3) Uani 1 1 d . . . . .
C5 C 0.2386(2) 0.0774(2) 0.87219(9) 0.0314(4) Uani 1 1 d . . . . .
H5A H 0.1453 0.0354 0.8287 0.047 Uiso 1 1 calc R U . . .
H5B H 0.1795 0.0877 0.9103 0.047 Uiso 1 1 calc R U . . .
H5C H 0.287 -0.0074 0.8798 0.047 Uiso 1 1 calc R U . . .
C6 C 0.8304(2) 0.5347(2) 1.05266(8) 0.0228(3) Uani 1 1 d . . . . .
C7 C 0.6930(2) 0.3715(2) 1.07534(8) 0.0289(4) Uani 1 1 d . . . . .
H7A H 0.5667 0.3605 1.0631 0.043 Uiso 1 1 calc R U . . .
H7B H 0.7283 0.3795 1.1254 0.043 Uiso 1 1 calc R U . . .
H7C H 0.6934 0.2671 1.0524 0.043 Uiso 1 1 calc R U . . .
C8 C 0.9917(2) 0.6745(2) 1.09059(8) 0.0235(3) Uani 1 1 d . . . . .
C9 C 1.0739(2) 0.7108(2) 1.16636(8) 0.0288(4) Uani 1 1 d . U . . .
H9A1 H 1.0832 0.6057 1.1806 0.035 Uiso 0.855(9) 1 calc R U P A 1
H9A2 H 0.9892 0.7309 1.1921 0.035 Uiso 0.855(9) 1 calc R U P A 1
H9B1 H 1.1417 0.6419 1.1779 0.035 Uiso 0.145(9) 1 calc R U P A 2
H9B2 H 0.9741 0.6794 1.1933 0.035 Uiso 0.145(9) 1 calc R U P A 2
C10A C 1.2680(3) 0.8724(4) 1.18436(11) 0.0285(6) Uani 0.855(9) 1 d . U P A 1
H10A H 1.3625 0.8369 1.1747 0.034 Uiso 0.855(9) 1 calc R U P A 1
H10B H 1.2991 0.9167 1.2343 0.034 Uiso 0.855(9) 1 calc R U P A 1
C11A C 1.2801(4) 1.0229(3) 1.14371(12) 0.0292(7) Uani 0.855(9) 1 d . U P A 1
H11A H 1.4063 1.1273 1.1595 0.035 Uiso 0.855(9) 1 calc R U P A 1
H11B H 1.1856 1.0585 1.1534 0.035 Uiso 0.855(9) 1 calc R U P A 1
C10B C 1.222(3) 0.928(2) 1.1824(8) 0.036(4) Uani 0.145(9) 1 d . U P A 2
H10C H 1.1472 0.9927 1.1812 0.043 Uiso 0.145(9) 1 calc R U P A 2
H10D H 1.2985 0.9568 1.2297 0.043 Uiso 0.145(9) 1 calc R U P A 2
C11B C 1.350(3) 0.994(2) 1.1339(8) 0.040(4) Uani 0.145(9) 1 d . U P A 2
H11C H 1.4384 1.1219 1.149 0.048 Uiso 0.145(9) 1 calc R U P A 2
H11D H 1.4245 0.9294 1.1343 0.048 Uiso 0.145(9) 1 calc R U P A 2
C12 C 1.2455(2) 0.9682(2) 1.06541(9) 0.0307(4) Uani 1 1 d . U . . .
H12A H 1.2324 1.0601 1.0405 0.037 Uiso 0.855(9) 1 calc R U P A 1
H12B H 1.3533 0.9563 1.0539 0.037 Uiso 0.855(9) 1 calc R U P A 1
H12C H 1.3281 0.9781 1.0326 0.037 Uiso 0.145(9) 1 calc R U P A 2
H12D H 1.2122 1.0655 1.0614 0.037 Uiso 0.145(9) 1 calc R U P A 2
C13 C 1.0689(2) 0.7943(2) 1.04435(8) 0.0241(3) Uani 1 1 d . . . . .
C14 C -0.2320(2) -0.0139(2) 0.52784(8) 0.0226(3) Uani 1 1 d . . . . .
C15 C -0.1091(2) 0.0137(2) 0.64922(8) 0.0278(4) Uani 1 1 d . . . . .
C16 C -0.2772(2) -0.1504(2) 0.64624(8) 0.0283(4) Uani 1 1 d . . . . .
H16 H -0.3 -0.2023 0.687 0.034 Uiso 1 1 calc R U . . .
C17 C -0.4042(2) -0.2324(2) 0.58586(8) 0.0254(3) Uani 1 1 d . . . . .
C18 C -0.5767(2) -0.4070(2) 0.58057(9) 0.0304(4) Uani 1 1 d . . . . .
H18A H -0.583 -0.4435 0.6263 0.046 Uiso 1 1 calc R U . . .
H18B H -0.5714 -0.4968 0.5493 0.046 Uiso 1 1 calc R U . . .
H18C H -0.6887 -0.395 0.5626 0.046 Uiso 1 1 calc R U . . .
C19 C -0.3015(2) 0.0160(2) 0.40239(8) 0.0238(3) Uani 1 1 d . . . . .
C20 C -0.4771(2) -0.1547(2) 0.37671(9) 0.0325(4) Uani 1 1 d . . . . .
H20A H -0.4517 -0.2543 0.3848 0.049 Uiso 1 1 calc R U . . .
H20B H -0.5209 -0.162 0.3272 0.049 Uiso 1 1 calc R U . . .
H20C H -0.5743 -0.1604 0.4012 0.049 Uiso 1 1 calc R U . . .
C21 C -0.2075(2) 0.1505(2) 0.36725(8) 0.0241(3) Uani 1 1 d . . . . .
C22 C -0.0484(2) 0.2811(2) 0.41555(8) 0.0243(3) Uani 1 1 d . . . . .
C23 C 0.0928(2) 0.4534(2) 0.39833(8) 0.0292(4) Uani 1 1 d . . . . .
H23A H 0.2124 0.4503 0.398 0.035 Uiso 1 1 calc R U . . .
H23B H 0.1186 0.5526 0.4338 0.035 Uiso 1 1 calc R U . . .
C24 C 0.0163(3) 0.4835(2) 0.32746(9) 0.0416(5) Uani 1 1 d . . . . .
H24A H -0.0768 0.5252 0.332 0.05 Uiso 1 1 calc R U . . .
H24B H 0.1211 0.5779 0.311 0.05 Uiso 1 1 calc R U . . .
C25 C -0.0758(3) 0.3170(2) 0.27469(9) 0.0431(5) Uani 1 1 d . . . . .
H25A H 0.0156 0.2724 0.2714 0.052 Uiso 1 1 calc R U . . .
H25B H -0.1111 0.3464 0.229 0.052 Uiso 1 1 calc R U . . .
C26 C -0.2513(2) 0.1713(2) 0.29333(8) 0.0309(4) Uani 1 1 d . . . . .
H26A H -0.3546 0.203 0.2858 0.037 Uiso 1 1 calc R U . . .
H26B H -0.2932 0.0575 0.2634 0.037 Uiso 1 1 calc R U . . .
N1 N 0.7029(2) 0.56375(18) 0.87076(7) 0.0281(3) Uani 1 1 d . . . . .
N2 N 0.53135(18) 0.33271(17) 0.92983(7) 0.0244(3) Uani 1 1 d . . . . .
N3 N 0.81685(18) 0.57469(16) 0.98619(6) 0.0237(3) Uani 1 1 d . . . . .
N4 N 0.96496(18) 0.73677(16) 0.98103(7) 0.0267(3) Uani 1 1 d . . . . .
N5 N -0.0978(2) 0.07478(18) 0.58569(7) 0.0262(3) Uani 1 1 d . . . . .
N6 N -0.38353(19) -0.16346(17) 0.52460(6) 0.0258(3) Uani 1 1 d . . . . .
N7 N -0.19726(18) 0.06851(16) 0.46953(6) 0.0245(3) Uani 1 1 d . . . . .
N8 N -0.03997(18) 0.23335(17) 0.47753(7) 0.0262(3) Uani 1 1 d . . . . .
O1 O 0.6052(2) 0.57490(17) 0.75852(6) 0.0488(4) Uani 1 1 d . . . . .
O2 O 0.01783(17) 0.09905(16) 0.69967(6) 0.0377(3) Uani 1 1 d . . . . .
H1 H 0.807(3) 0.665(3) 0.8742(10) 0.045 Uiso 1 1 d . U . . .
H5 H 0.002(3) 0.177(3) 0.5823(10) 0.045 Uiso 1 1 d . U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N2 1.2967(19) . ?
C1 N1 1.353(2) . ?
C1 N3 1.393(2) . ?
C2 O1 1.223(2) . ?
C2 N1 1.401(2) . ?
C2 C3 1.433(2) . ?
C3 C4 1.356(2) . ?
C3 H3 0.95 . ?
C4 N2 1.386(2) . ?
C4 C5 1.497(2) . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 C8 1.368(2) . ?
C6 N3 1.3846(19) . ?
C6 C7 1.487(2) . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 C13 1.413(2) . ?
C8 C9 1.499(2) . ?
C9 C10A 1.519(3) . ?
C9 C10B 1.663(16) . ?
C9 H9A1 0.99 . ?
C9 H9A2 0.99 . ?
C9 H9B1 0.99 . ?
C9 H9B2 0.99 . ?
C10A C11A 1.533(4) . ?
C10A H10A 0.99 . ?
C10A H10B 0.99 . ?
C11A C12 1.541(3) . ?
C11A H11A 0.99 . ?
C11A H11B 0.99 . ?
C10B C11B 1.48(3) . ?
C10B H10C 0.99 . ?
C10B H10D 0.99 . ?
C11B C12 1.433(15) . ?
C11B H11C 0.99 . ?
C11B H11D 0.99 . ?
C12 C13 1.497(2) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C12 H12C 0.99 . ?
C12 H12D 0.99 . ?
C13 N4 1.323(2) . ?
C14 N6 1.2994(19) . ?
C14 N5 1.354(2) . ?
C14 N7 1.3927(19) . ?
C15 O2 1.2262(19) . ?
C15 N5 1.395(2) . ?
C15 C16 1.435(2) . ?
C16 C17 1.359(2) . ?
C16 H16 0.95 . ?
C17 N6 1.3851(19) . ?
C17 C18 1.495(2) . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 C21 1.363(2) . ?
C19 N7 1.3874(19) . ?
C19 C20 1.488(2) . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C21 C22 1.416(2) . ?
C21 C26 1.497(2) . ?
C22 N8 1.322(2) . ?
C22 C23 1.500(2) . ?
C23 C24 1.533(2) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 C25 1.512(3) . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C25 C26 1.528(2) . ?
C25 H25A 0.99 . ?
C25 H25B 0.99 . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?
N1 H1 0.88(2) . ?
N3 N4 1.3850(17) . ?
N5 H5 0.89(2) . ?
N7 N8 1.3839(17) . ?

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
N2 C1 N1 124.74(14) . . ?
N2 C1 N3 120.47(14) . . ?
N1 C1 N3 114.79(14) . . ?
O1 C2 N1 119.58(16) . . ?
O1 C2 C3 127.72(16) . . ?
N1 C2 C3 112.69(14) . . ?
C4 C3 C2 120.62(15) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 N2 123.59(15) . . ?
C3 C4 C5 122.34(15) . . ?
N2 C4 C5 114.05(14) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 C6 N3 105.60(13) . . ?
C8 C6 C7 129.09(14) . . ?
N3 C6 C7 125.31(14) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 C13 106.14(14) . . ?
C6 C8 C9 130.07(14) . . ?
C13 C8 C9 123.67(14) . . ?
C8 C9 C10A 111.49(15) . . ?
C8 C9 C10B 104.7(5) . . ?
C8 C9 H9A1 109.3 . . ?
C10A C9 H9A1 109.3 . . ?
C8 C9 H9A2 109.3 . . ?
C10A C9 H9A2 109.3 . . ?
H9A1 C9 H9A2 108 . . ?
C8 C9 H9B1 110.8 . . ?
C10B C9 H9B1 110.8 . . ?
C8 C9 H9B2 110.8 . . ?
C10B C9 H9B2 110.8 . . ?
H9B1 C9 H9B2 108.9 . . ?
C9 C10A C11A 112.4(2) . . ?
C9 C10A H10A 109.1 . . ?
C11A C10A H10A 109.1 . . ?
C9 C10A H10B 109.1 . . ?
C11A C10A H10B 109.1 . . ?
H10A C10A H10B 107.8 . . ?
C10A C11A C12 112.4(2) . . ?
C10A C11A H11A 109.1 . . ?
C12 C11A H11A 109.1 . . ?
C10A C11A H11B 109.1 . . ?
C12 C11A H11B 109.1 . . ?
H11A C11A H11B 107.9 . . ?
C11B C10B C9 114.7(17) . . ?
C11B C10B H10C 108.6 . . ?
C9 C10B H10C 108.6 . . ?
C11B C10B H10D 108.6 . . ?
C9 C10B H10D 108.6 . . ?
H10C C10B H10D 107.6 . . ?
C12 C11B C10B 110.7(18) . . ?
C12 C11B H11C 109.5 . . ?
C10B C11B H11C 109.5 . . ?
C12 C11B H11D 109.5 . . ?
C10B C11B H11D 109.5 . . ?
H11C C11B H11D 108.1 . . ?
C11B C12 C13 115.0(6) . . ?
C13 C12 C11A 108.44(15) . . ?
C13 C12 H12A 110 . . ?
C11A C12 H12A 110 . . ?
C13 C12 H12B 110 . . ?
C11A C12 H12B 110 . . ?
H12A C12 H12B 108.4 . . ?
C11B C12 H12C 108.5 . . ?
C13 C12 H12C 108.5 . . ?
C11B C12 H12D 108.5 . . ?
C13 C12 H12D 108.5 . . ?
H12C C12 H12D 107.5 . . ?
N4 C13 C8 112.27(14) . . ?
N4 C13 C12 124.19(14) . . ?
C8 C13 C12 123.52(14) . . ?
N6 C14 N5 124.74(14) . . ?
N6 C14 N7 120.69(14) . . ?
N5 C14 N7 114.57(14) . . ?
O2 C15 N5 119.80(15) . . ?
O2 C15 C16 127.40(15) . . ?
N5 C15 C16 112.80(14) . . ?
C17 C16 C15 120.82(15) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 N6 123.15(15) . . ?
C16 C17 C18 122.03(15) . . ?
N6 C17 C18 114.81(14) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C19 N7 105.59(13) . . ?
C21 C19 C20 129.12(14) . . ?
N7 C19 C20 125.29(14) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 C22 106.36(14) . . ?
C19 C21 C26 130.65(14) . . ?
C22 C21 C26 122.99(14) . . ?
N8 C22 C21 111.96(14) . . ?
N8 C22 C23 124.15(14) . . ?
C21 C22 C23 123.89(14) . . ?
C22 C23 C24 109.81(13) . . ?
C22 C23 H23A 109.7 . . ?
C24 C23 H23A 109.7 . . ?
C22 C23 H23B 109.7 . . ?
C24 C23 H23B 109.7 . . ?
H23A C23 H23B 108.2 . . ?
C25 C24 C23 112.53(15) . . ?
C25 C24 H24A 109.1 . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24B 109.1 . . ?
C23 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
C24 C25 C26 111.90(16) . . ?
C24 C25 H25A 109.2 . . ?
C26 C25 H25A 109.2 . . ?
C24 C25 H25B 109.2 . . ?
C26 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C21 C26 C25 109.59(14) . . ?
C21 C26 H26A 109.8 . . ?
C25 C26 H26A 109.8 . . ?
C21 C26 H26B 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.2 . . ?
C1 N1 C2 122.84(14) . . ?
C1 N1 H1 118.0(13) . . ?
C2 N1 H1 119.2(13) . . ?
C1 N2 C4 115.46(13) . . ?
C6 N3 N4 112.06(12) . . ?
C6 N3 C1 130.00(13) . . ?
N4 N3 C1 117.84(12) . . ?
C13 N4 N3 103.92(12) . . ?
C14 N5 C15 122.79(14) . . ?
C14 N5 H5 117.6(13) . . ?
C15 N5 H5 119.6(13) . . ?
C14 N6 C17 115.68(13) . . ?
N8 N7 C19 111.90(12) . . ?
N8 N7 C14 117.74(12) . . ?
C19 N7 C14 130.29(13) . . ?
C22 N8 N7 104.19(12) . . ?

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 C2 C3 C4 177.92(18) . . . . ?
N1 C2 C3 C4 -1.6(2) . . . . ?
C2 C3 C4 N2 2.9(3) . . . . ?
C2 C3 C4 C5 -175.26(15) . . . . ?
N3 C6 C8 C13 0.09(17) . . . . ?
C7 C6 C8 C13 -179.62(16) . . . . ?
N3 C6 C8 C9 176.22(15) . . . . ?
C7 C6 C8 C9 -3.5(3) . . . . ?
C6 C8 C9 C10A 173.3(2) . . . . ?
C13 C8 C9 C10A -11.2(3) . . . . ?
C6 C8 C9 C10B -160.3(9) . . . . ?
C13 C8 C9 C10B 15.3(9) . . . . ?
C8 C9 C10A C11A 39.8(3) . . . . ?
C9 C10A C11A C12 -62.4(4) . . . . ?
C8 C9 C10B C11B -48(2) . . . . ?
C9 C10B C11B C12 63(3) . . . . ?
C10B C11B C12 C13 -41(2) . . . . ?
C10A C11A C12 C13 49.9(3) . . . . ?
C6 C8 C13 N4 0.18(19) . . . . ?
C9 C8 C13 N4 -176.27(14) . . . . ?
C6 C8 C13 C12 178.75(15) . . . . ?
C9 C8 C13 C12 2.3(2) . . . . ?
C11B C12 C13 N4 -171.9(13) . . . . ?
C11A C12 C13 N4 157.1(2) . . . . ?
C11B C12 C13 C8 9.7(13) . . . . ?
C11A C12 C13 C8 -21.3(3) . . . . ?
O2 C15 C16 C17 -178.44(17) . . . . ?
N5 C15 C16 C17 1.3(2) . . . . ?
C15 C16 C17 N6 -1.5(2) . . . . ?
C15 C16 C17 C18 177.49(15) . . . . ?
N7 C19 C21 C22 -0.32(17) . . . . ?
C20 C19 C21 C22 -179.47(16) . . . . ?
N7 C19 C21 C26 -179.57(16) . . . . ?
C20 C19 C21 C26 1.3(3) . . . . ?
C19 C21 C22 N8 0.39(19) . . . . ?
C26 C21 C22 N8 179.71(15) . . . . ?
C19 C21 C22 C23 -179.33(15) . . . . ?
C26 C21 C22 C23 0.0(3) . . . . ?
N8 C22 C23 C24 -167.08(16) . . . . ?
C21 C22 C23 C24 12.6(2) . . . . ?
C22 C23 C24 C25 -43.5(2) . . . . ?
C23 C24 C25 C26 64.5(2) . . . . ?
C19 C21 C26 C25 -163.48(17) . . . . ?
C22 C21 C26 C25 17.4(2) . . . . ?
C24 C25 C26 C21 -48.1(2) . . . . ?
N2 C1 N1 C2 2.1(3) . . . . ?
N3 C1 N1 C2 -177.38(14) . . . . ?
O1 C2 N1 C1 179.72(16) . . . . ?
C3 C2 N1 C1 -0.7(2) . . . . ?
N1 C1 N2 C4 -0.9(2) . . . . ?
N3 C1 N2 C4 178.54(13) . . . . ?
C3 C4 N2 C1 -1.6(2) . . . . ?
C5 C4 N2 C1 176.68(14) . . . . ?
C8 C6 N3 N4 -0.31(17) . . . . ?
C7 C6 N3 N4 179.40(14) . . . . ?
C8 C6 N3 C1 -176.48(15) . . . . ?
C7 C6 N3 C1 3.2(3) . . . . ?
N2 C1 N3 C6 -2.3(3) . . . . ?
N1 C1 N3 C6 177.22(14) . . . . ?
N2 C1 N3 N4 -178.26(13) . . . . ?
N1 C1 N3 N4 1.2(2) . . . . ?
C8 C13 N4 N3 -0.35(17) . . . . ?
C12 C13 N4 N3 -178.92(14) . . . . ?
C6 N3 N4 C13 0.41(17) . . . . ?
C1 N3 N4 C13 177.09(13) . . . . ?
N6 C14 N5 C15 -0.3(3) . . . . ?
N7 C14 N5 C15 179.35(14) . . . . ?
O2 C15 N5 C14 179.30(15) . . . . ?
C16 C15 N5 C14 -0.5(2) . . . . ?
N5 C14 N6 C17 0.2(2) . . . . ?
N7 C14 N6 C17 -179.42(13) . . . . ?
C16 C17 N6 C14 0.7(2) . . . . ?
C18 C17 N6 C14 -178.35(14) . . . . ?
C21 C19 N7 N8 0.17(17) . . . . ?
C20 C19 N7 N8 179.36(15) . . . . ?
C21 C19 N7 C14 176.97(15) . . . . ?
C20 C19 N7 C14 -3.8(3) . . . . ?
N6 C14 N7 N8 175.66(14) . . . . ?
N5 C14 N7 N8 -4.0(2) . . . . ?
N6 C14 N7 C19 -1.0(3) . . . . ?
N5 C14 N7 C19 179.37(15) . . . . ?
C21 C22 N8 N7 -0.28(18) . . . . ?
C23 C22 N8 N7 179.44(15) . . . . ?
C19 N7 N8 C22 0.07(17) . . . . ?
C14 N7 N8 C22 -177.18(13) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_name_systematic        
6-methyl-2-(3-methyl-4,5,6,7-tetrahydro-2H-indazol-2-yl)pyrimidin-4(3H)-one
####################################################################### 
# 
# 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_16jlr003
_database_code_depnum_ccdc_archive 'CCDC 1976832'
loop_
_audit_author_name
_audit_author_address
'Piero Macchi'
;University of Bern
Switzerland
;
_audit_update_record             
;
2020-01-10 deposited with the CCDC.	2020-05-07 downloaded from the CCDC.
;

_audit_creation_date             2016-12-12T15:01:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C14 H18 N4 O'
_chemical_formula_weight         258.32

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_Int_Tables_number      60
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   18.8002(2)
_cell_length_b                   9.62410(10)
_cell_length_c                   14.3730(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2600.58(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6648
_cell_measurement_theta_min      2.152
_cell_measurement_theta_max      28.047

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_size_max          0.3237
_exptl_crystal_size_mid          0.2243
_exptl_crystal_size_min          0.1952
_exptl_crystal_density_diffrn    1.32
_exptl_crystal_F_000             1104
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0976
-1 0 0 0.0976
0 0 1 0.1121
0 0 -1 0.1121
0 1 0 0.1658
0 -1 0 0.1578


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
        (compiled Dec  9 2014,15:38:47)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.984

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_ambient_temperature      173(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0965
_diffrn_orient_matrix_ub_11      0.0006431
_diffrn_orient_matrix_ub_12      -0.067915
_diffrn_orient_matrix_ub_13      -0.0191959
_diffrn_orient_matrix_ub_21      0.0377157
_diffrn_orient_matrix_ub_22      0.001185
_diffrn_orient_matrix_ub_23      0.0002959
_diffrn_orient_matrix_ub_31      0.0000361
_diffrn_orient_matrix_ub_32      -0.0286619
_diffrn_orient_matrix_ub_33      0.0454544
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_number            14668
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.167
_diffrn_reflns_theta_max         28.142
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.921
_reflns_Friedel_coverage         0
_reflns_number_total             2933
_reflns_number_gt                2475
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
        (compiled Dec  9 2014,15:38:47)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
        (compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
        (compiled Dec  9 2014,15:38:47)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+0.7943P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0037(4)
_refine_ls_number_reflns         2933
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.044
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0938
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.32895(5) 0.40608(13) 0.55695(8) 0.0261(3) Uani 1 1 d . . . . .
C2 C 0.33173(6) 0.25811(13) 0.56533(8) 0.0257(3) Uani 1 1 d . . . . .
H2 H 0.2903 0.2045 0.5535 0.031 Uiso 1 1 calc R U . . .
C3 C 0.39320(6) 0.19342(13) 0.59005(8) 0.0265(3) Uani 1 1 d . . . . .
C4 C 0.39838(7) 0.03954(14) 0.60058(11) 0.0389(3) Uani 1 1 d . . . . .
H4A H 0.3522 -0.0027 0.5867 0.058 Uiso 1 1 calc R U . . .
H4B H 0.4122 0.0169 0.6646 0.058 Uiso 1 1 calc R U . . .
H4C H 0.4342 0.0034 0.5574 0.058 Uiso 1 1 calc R U . . .
C5 C 0.45257(5) 0.39743(12) 0.60208(7) 0.0219(2) Uani 1 1 d . . . . .
C6 C 0.57846(5) 0.44168(12) 0.65706(8) 0.0239(3) Uani 1 1 d . . . . .
C7 C 0.61271(5) 0.56417(13) 0.67384(8) 0.0246(3) Uani 1 1 d . . . . .
C8 C 0.56502(6) 0.67151(12) 0.64874(8) 0.0244(3) Uani 1 1 d . . . . .
C9 C 0.58026(6) 0.82284(13) 0.65962(9) 0.0310(3) Uani 1 1 d . . . . .
H9A H 0.5511 0.8611 0.711 0.037 Uiso 1 1 calc R U . . .
H9B H 0.5672 0.8724 0.6017 0.037 Uiso 1 1 calc R U . . .
C10 C 0.65944(6) 0.84645(14) 0.68068(9) 0.0325(3) Uani 1 1 d . . . . .
H10A H 0.6871 0.839 0.6223 0.039 Uiso 1 1 calc R U . . .
H10B H 0.6661 0.9414 0.7057 0.039 Uiso 1 1 calc R U . . .
C11 C 0.68753(6) 0.74099(14) 0.75077(9) 0.0345(3) Uani 1 1 d . . . . .
H11A H 0.6582 0.7447 0.8079 0.041 Uiso 1 1 calc R U . . .
H11B H 0.737 0.7654 0.7678 0.041 Uiso 1 1 calc R U . . .
C12 C 0.68585(6) 0.59378(14) 0.71109(9) 0.0307(3) Uani 1 1 d . . . . .
H12A H 0.7214 0.5849 0.6606 0.037 Uiso 1 1 calc R U . . .
H12B H 0.6979 0.5259 0.7604 0.037 Uiso 1 1 calc R U . . .
C13 C 0.60540(6) 0.29629(13) 0.66679(9) 0.0302(3) Uani 1 1 d . . . . .
H13A H 0.5672 0.2373 0.6929 0.036 Uiso 1 1 calc R U . . .
H13B H 0.6456 0.2955 0.7112 0.036 Uiso 1 1 calc R U . . .
C14 C 0.62994(7) 0.23485(14) 0.57458(10) 0.0387(3) Uani 1 1 d . . . . .
H14A H 0.5894 0.2288 0.5318 0.058 Uiso 1 1 calc R U . . .
H14B H 0.6494 0.1417 0.5852 0.058 Uiso 1 1 calc R U . . .
H14C H 0.6667 0.2945 0.5474 0.058 Uiso 1 1 calc R U . . .
N1 N 0.39396(5) 0.47024(11) 0.57753(7) 0.0244(2) Uani 1 1 d . . . . .
N2 N 0.45580(5) 0.26377(10) 0.60862(7) 0.0261(2) Uani 1 1 d . . . . .
N3 N 0.51192(4) 0.47945(10) 0.62245(6) 0.0232(2) Uani 1 1 d . . . . .
N4 N 0.50383(5) 0.62169(10) 0.61767(7) 0.0247(2) Uani 1 1 d . . . . .
O1 O 0.27745(4) 0.47820(10) 0.53604(7) 0.0373(2) Uani 1 1 d . . . . .
H1 H 0.3975(7) 0.5616(16) 0.5754(10) 0.038(4) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 O1 1.2287(14) . ?
C1 N1 1.4009(14) . ?
C1 C2 1.4302(17) . ?
C2 C3 1.3599(16) . ?
C2 H2 0.95 . ?
C3 N2 1.3837(14) . ?
C3 C4 1.4919(17) . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 N2 1.2913(15) . ?
C5 N1 1.3526(14) . ?
C5 N3 1.3978(13) . ?
C6 C7 1.3648(16) . ?
C6 N3 1.3944(13) . ?
C6 C13 1.4946(17) . ?
C7 C8 1.4146(16) . ?
C7 C12 1.5029(14) . ?
C8 N4 1.3240(14) . ?
C8 C9 1.4925(17) . ?
C9 C10 1.5360(15) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.5245(19) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.5276(18) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 C14 1.5228(19) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
N1 H1 0.882(15) . ?
N3 N4 1.3790(14) . ?

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
O1 C1 N1 119.36(11) . . ?
O1 C1 C2 127.73(10) . . ?
N1 C1 C2 112.91(10) . . ?
C3 C2 C1 120.59(10) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 N2 123.31(11) . . ?
C2 C3 C4 122.44(11) . . ?
N2 C3 C4 114.24(10) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 N1 124.98(10) . . ?
N2 C5 N3 120.65(10) . . ?
N1 C5 N3 114.36(10) . . ?
C7 C6 N3 105.13(10) . . ?
C7 C6 C13 129.22(10) . . ?
N3 C6 C13 125.55(10) . . ?
C6 C7 C8 106.66(9) . . ?
C6 C7 C12 131.18(11) . . ?
C8 C7 C12 122.16(11) . . ?
N4 C8 C7 111.85(10) . . ?
N4 C8 C9 123.75(11) . . ?
C7 C8 C9 124.35(10) . . ?
C8 C9 C10 110.55(10) . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 111.56(10) . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108 . . ?
C10 C11 C12 111.32(11) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108 . . ?
C7 C12 C11 109.13(10) . . ?
C7 C12 H12A 109.9 . . ?
C11 C12 H12A 109.9 . . ?
C7 C12 H12B 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C6 C13 C14 112.63(10) . . ?
C6 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
C6 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 N1 C1 122.51(10) . . ?
C5 N1 H1 117.7(9) . . ?
C1 N1 H1 119.8(9) . . ?
C5 N2 C3 115.69(10) . . ?
N4 N3 C6 112.06(9) . . ?
N4 N3 C5 117.52(9) . . ?
C6 N3 C5 130.06(10) . . ?
C8 N4 N3 104.29(9) . . ?


# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_name_systematic        
2-(3-ethyl-4,5,6,7-tetrahydro-2H-indazol-2-yl)-6-methylpyrimidin-4(3H)-one
####################################################################### 
# 
# 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_19JLR010_MP303A1
_database_code_depnum_ccdc_archive 'CCDC 1976862'
loop_
_audit_author_name
_audit_author_address
'Michal Andrzejewski'
;University of Bern
Switzerland
;
_audit_update_record             
;
2020-01-10 deposited with the CCDC.	2020-05-07 downloaded from the CCDC.
;
_audit_creation_date             2020-01-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
6-ethyl-4-hydroxy-2-(3-methyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)pyrimidin-1-ium
_chemical_formula_moiety         'Cl, C10 H13 N4 O2, H2 O'
_chemical_formula_sum            'C10 H15 Cl N4 O3'
_chemical_formula_weight         274.71
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C40 H40 N8 O8 Cl8 '
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                   8.66205(5)
_cell_length_b                   14.39226(6)
_cell_length_c                   9.94738(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.8062(4)
_cell_angle_gamma                90
_cell_volume                     1239.982(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    36763
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      77.0270
_cell_measurement_theta_min      4.4440
_shelx_estimated_absorpt_T_max   0.872
_shelx_estimated_absorpt_T_min   0.602
_exptl_absorpt_coefficient_mu    2.824
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.2
_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  0.0300
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            53002
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.972
_diffrn_reflns_theta_min         4.445
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  54.00   0.50    0.20    --  -18.75  45.00 -30.00  170
  2  ω      8.00  35.00   0.50    0.20    --   38.00  93.00  57.22   54
  3  ω      4.00  35.00   0.50    0.20    --   34.00  93.00 117.01   62
  4  ω     27.00 122.00   0.50    0.20    --   50.00  78.00 140.63  190
  5  ω     81.00 167.00   0.50    0.40    --   94.00  49.00  97.72  172
  6  ω    104.00 171.00   0.50    0.40    --  107.11 109.00 124.00  134
  7  ω     91.00 171.00   0.50    0.40    --  107.11  61.00 120.00  160
  8  ω     91.00 171.00   0.50    0.40    --  107.11  61.00 -30.00  160
  9  ω     91.00 171.00   0.50    0.40    --  107.11  61.00  30.00  160
 10  ω     95.00 171.00   0.50    0.40    --  107.11  45.00   0.00  152
 11  ω     91.00 171.00   0.50    0.40    --  107.11  61.00 150.00  160
 12  ω     95.00 171.00   0.50    0.40    --  107.11 125.00  30.00  152
 13  ω     91.00 171.00   0.50    0.40    --  107.11  61.00 -60.00  160
 14  ω     90.00 171.00   0.50    0.40    --  107.11  63.00-140.79  162
 15  ω     91.00 171.00   0.50    0.40    --  107.11  61.00 -90.00  160
 16  ω     85.00 171.00   0.50    0.40    --  107.11  77.00  90.00  172
 17  ω     85.00 171.00   0.50    0.40    --  107.11  77.00 -60.00  172
 18  ω     85.00 171.00   0.50    0.40    --  107.11  77.00-180.00  172
 19  ω     85.00 171.00   0.50    0.40    --  107.11  77.00   0.00  172
 20  ω     85.00 171.00   0.50    0.40    --  107.11  77.00  30.00  172
 21  ω     85.00 171.00   0.50    0.40    --  107.11  77.00 120.00  172
 22  ω     64.00 154.00   0.50    0.40    --   82.00  66.00 113.84  180
 23  ω     71.00 159.00   0.50    0.40    --   86.00  57.00  85.17  176
 24  ω     68.00 159.00   0.50    0.40    --   86.00  67.00-106.51  182
 25  ω     66.00 159.00   0.50    0.40    --   86.00  72.00-166.24  186
 26  ω     71.00 159.00   0.50    0.40    --   86.00  57.00-125.37  176
 27  ω     64.00 159.00   0.50    0.40    --   86.00  76.00   2.34  190
 28  ω     74.00 162.00   0.50    0.40    --   90.00  61.00 -58.80  176
 29  ω     57.00 146.00   0.50    0.20    --   74.00  64.00-176.65  178
 30  ω     59.00 151.00   0.50    0.40    --   78.00  69.00 -52.42  184
 31  ω     62.00 154.00   0.50    0.40    --   82.00  72.00 -88.07  184
 32  ω     60.00 154.00   0.50    0.40    --   82.00  76.00 -70.45  188
 33  ω     61.00 154.00   0.50    0.40    --   82.00  73.00  52.23  186
 34  ω     48.00 143.00   0.50    0.20    --   70.00  75.00 100.33  190
 35  ω     51.00 143.00   0.50    0.20    --   70.00  68.00  74.46  184
 36  ω     48.00 143.00   0.50    0.20    --   70.00  75.00 175.91  190
 37  ω     36.00 131.00   0.50    0.20    --   58.00  77.00  74.11  190
 38  ω     53.00 146.00   0.50    0.20    --   74.00  74.00 -61.20  186
 39  ω     40.00 135.00   0.50    0.20    --   62.00  77.00 147.26  190
 40  ω     40.00 135.00   0.50    0.20    --   62.00  75.00  27.42  190
 41  ω     40.00 135.00   0.50    0.20    --   62.00  75.00 -62.85  190
 42  ω     44.00 139.00   0.50    0.20    --   66.00  76.00  46.67  190
 43  ω     44.00 139.00   0.50    0.20    --   66.00  76.00 123.93  190
 44  ω     44.00 139.00   0.50    0.20    --   66.00  75.00 172.98  190
 45  ω     44.00 139.00   0.50    0.20    --   66.00  75.00   1.82  190
 46  ω     47.00 143.00   0.50    0.20    --   70.00  78.00-105.75  192
 47  ω     39.00 135.00   0.50    0.20    --   62.00  79.00-140.31  192
 48  ω     43.00 139.00   0.50    0.20    --   66.00  78.00-108.91  192
 49  ω     34.00 131.00   0.50    0.20    --   58.00  80.00 -32.51  194
 50  ω     42.00 139.00   0.50    0.20    --   66.00  80.00 -25.55  194
 51  ω     35.00  68.00   0.50    0.40    --  107.11 -61.00   0.00   66
 52  ω     35.00 108.00   0.50    0.40    --  107.11-109.00  28.00  146
 53  ω     35.00  96.00   0.50    0.20    --   47.70-125.00 -60.00  122
 54  ω     35.00 112.00   0.50    0.40    --  107.11-125.00 -30.00  154
 55  ω     35.00 112.00   0.50    0.40    --  107.11-125.00-120.00  154
 56  ω     35.00 112.00   0.50    0.40    --  107.11-125.00 -90.00  154
 57  ω     35.00 106.00   0.50    0.40    --  107.11 -94.00 -30.00  142
 58  ω     23.00  87.00   0.50    0.20    --   47.70-109.00  28.00  128
 59  ω     35.00 106.00   0.50    0.40    --  107.11 -94.00 120.00  142
 60  ω     35.00 106.00   0.50    0.40    --  107.11 -94.00  90.00  142
 61  ω     35.00 102.00   0.50    0.40    --  107.11 -77.00 120.00  134
 62  ω     35.00  68.00   0.50    0.40    --  107.11 -61.00  30.00   66
 63  ω     35.00  68.00   0.50    0.40    --  107.11 -61.00  60.00   66
 64  ω     35.00  68.00   0.50    0.40    --  107.11 -61.00 150.00   66
 65  ω     -1.00  82.00   0.50    0.20    --   47.70 -99.00   0.00  166
 66  ω     17.00  43.00   0.50    0.20    --   42.00  83.00  15.12   52
 67  ω     10.00  43.00   0.50    0.20    --   38.00  90.00 -66.64   66
 68  ω     28.00 122.00   0.50    0.20    --   50.00  77.00-139.68  188
 69  ω     31.00 126.00   0.50    0.20    --   54.00  79.00-130.72  190
 70  ω     30.00 126.00   0.50    0.20    --   54.00  80.00 111.97  192
 71  ω     27.00 122.00   0.50    0.20    --   50.00  79.00 179.41  190
 72  ω     -5.00  29.00   0.50    0.20    --   26.00  96.00 -33.82   68
 73  ω    -57.00   0.00   0.50    0.20    --  -18.75 109.00 124.00  114
 74  ω    -90.00  -3.00   0.50    0.20    --  -18.75 -57.00-150.00  174
 75  ω    -90.00  -2.00   0.50    0.20    --  -18.75 -61.00  30.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0330798000
_diffrn_orient_matrix_UB_12      -0.0242020000
_diffrn_orient_matrix_UB_13      -0.1476781000
_diffrn_orient_matrix_UB_21      -0.0472268000
_diffrn_orient_matrix_UB_22      -0.1015539000
_diffrn_orient_matrix_UB_23      0.0261567000
_diffrn_orient_matrix_UB_31      -0.1682360000
_diffrn_orient_matrix_UB_32      0.0237219000
_diffrn_orient_matrix_UB_33      -0.0386779000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                4976
_reflns_number_total             5090
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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         0.153
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 2249 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         5090
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0242
_refine_ls_restrained_S_all      1.071
_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)+(0.0305P)²+0.2736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0604
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O14-H14
 0.82 with sigma of 0.001
 H33B-H33A
 1.44 with sigma of 0.02
 H34B-H34A
 1.44 with sigma of 0.02
 O33-H33B
 0.95 with sigma of 0.02
 H34B-O34
 0.95 with sigma of 0.02
 H33B-H14 \\sim H14-H33A
 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C31(H31A,H31B)
3.b Aromatic/amide H refined with riding coordinates:
 N27(H27), N11(H11), N4(H4), N19(H19), C25(H25), C9(H9), C2(H2), C17(H17)
3.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C16(H16A,H16B,H16C), C13(H13A,H13B,H13C), C29(H29A,H29B,
 H29C)
3.d Idealised tetrahedral OH refined as rotating group:
 O30(H30)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl2 Cl 0.52257(6) 0.27452(3) 0.94181(5) 0.03063(12) Uani 1 1 d . . . . .
Cl1 Cl 0.08563(6) 0.51723(3) 0.98615(5) 0.03086(12) Uani 1 1 d . . . . .
O14 O 0.4048(2) 0.42974(10) 0.61449(16) 0.0292(3) Uani 1 1 d D . . . .
O12 O 0.3530(2) 0.86685(10) 0.64327(18) 0.0319(4) Uani 1 1 d . . . . .
O28 O 0.8760(2) 0.62239(10) 0.65575(16) 0.0314(4) Uani 1 1 d . . . . .
O30 O 0.88571(19) 0.18567(10) 0.59906(16) 0.0293(3) Uani 1 1 d . . . . .
H30 H 0.8321 0.1750 0.6646 0.044 Uiso 1 1 calc GR . . . .
O34 O 0.7311(2) 0.13271(11) 0.79454(16) 0.0326(4) Uani 1 1 d D . . . .
O33 O 0.2468(2) 0.37427(11) 0.80400(16) 0.0322(4) Uani 1 1 d D . . . .
N23 N 0.8353(2) 0.33124(12) 0.67509(17) 0.0233(4) Uani 1 1 d . . . . .
N7 N 0.3334(2) 0.57520(12) 0.67774(17) 0.0233(4) Uani 1 1 d . . . . .
N27 N 0.9538(2) 0.45797(12) 0.56600(17) 0.0233(4) Uani 1 1 d . . . . .
H27 H 0.9660 0.5172 0.5623 0.028 Uiso 1 1 calc R . . . .
N11 N 0.4469(2) 0.70248(12) 0.56637(17) 0.0240(4) Uani 1 1 d . . . . .
H11 H 0.4541 0.7619 0.5597 0.029 Uiso 1 1 calc R . . . .
N5 N 0.2729(2) 0.72639(12) 0.73458(18) 0.0238(4) Uani 1 1 d . . . . .
N4 N 0.1733(2) 0.69811(13) 0.83284(18) 0.0254(4) Uani 1 1 d . . . . .
H4 H 0.1529 0.6416 0.8543 0.031 Uiso 1 1 calc R . . . .
N20 N 0.7876(2) 0.48221(12) 0.74051(17) 0.0238(4) Uani 1 1 d . . . . .
N19 N 0.6931(2) 0.45365(12) 0.84283(18) 0.0260(4) Uani 1 1 d . . . . .
H19 H 0.6738 0.3971 0.8649 0.031 Uiso 1 1 calc R . . . .
C8 C 0.4179(2) 0.51884(15) 0.59896(19) 0.0237(4) Uani 1 1 d . . . . .
C24 C 0.9089(2) 0.27489(15) 0.58915(19) 0.0233(4) Uani 1 1 d . . . . .
C10 C 0.5315(2) 0.64615(14) 0.48369(19) 0.0223(4) Uani 1 1 d . . . . .
C25 C 1.0083(2) 0.30838(14) 0.4882(2) 0.0238(4) Uani 1 1 d . . . . .
H25 H 1.0581 0.2675 0.4309 0.029 Uiso 1 1 calc R . . . .
C9 C 0.5179(3) 0.55282(14) 0.4992(2) 0.0247(4) Uani 1 1 d . . . . .
H9 H 0.5732 0.5121 0.4454 0.030 Uiso 1 1 calc R . . . .
C26 C 1.0291(2) 0.40131(14) 0.4773(2) 0.0227(4) Uani 1 1 d . . . . .
C22 C 0.8605(2) 0.42055(14) 0.6590(2) 0.0221(4) Uani 1 1 d . . . . .
C1 C 0.2737(3) 0.82542(15) 0.7284(2) 0.0256(4) Uani 1 1 d . . . . .
C21 C 0.7946(3) 0.58098(14) 0.7385(2) 0.0254(4) Uani 1 1 d . . . . .
C6 C 0.3526(2) 0.66455(14) 0.6579(2) 0.0222(4) Uani 1 1 d . . . . .
C32 C 1.2365(3) 0.38696(16) 0.3001(2) 0.0318(5) Uani 1 1 d . . . . .
H32A H 1.2895 0.4223 0.2331 0.048 Uiso 1 1 calc GR . . . .
H32B H 1.1809 0.3370 0.2575 0.048 Uiso 1 1 calc GR . . . .
H32C H 1.3102 0.3620 0.3634 0.048 Uiso 1 1 calc GR . . . .
C15 C 0.6295(3) 0.69478(16) 0.3835(2) 0.0274(5) Uani 1 1 d . . . . .
H15A H 0.6883 0.7429 0.4296 0.033 Uiso 1 1 calc R . . . .
H15B H 0.5625 0.7251 0.3181 0.033 Uiso 1 1 calc R . . . .
C16 C 0.7409(3) 0.63255(17) 0.3094(2) 0.0341(5) Uani 1 1 d . . . . .
H16A H 0.7952 0.6684 0.2439 0.051 Uiso 1 1 calc GR . . . .
H16B H 0.6845 0.5837 0.2651 0.051 Uiso 1 1 calc GR . . . .
H16C H 0.8136 0.6061 0.3723 0.051 Uiso 1 1 calc GR . . . .
C31 C 1.1237(3) 0.44963(14) 0.3732(2) 0.0251(4) Uani 1 1 d . . . . .
H31A H 1.1814 0.4994 0.4164 0.030 Uiso 1 1 calc R . . . .
H31B H 1.0544 0.4777 0.3074 0.030 Uiso 1 1 calc R . . . .
C2 C 0.1708(3) 0.85292(14) 0.8287(2) 0.0259(4) Uani 1 1 d . . . . .
H2 H 0.1456 0.9139 0.8504 0.031 Uiso 1 1 calc R . . . .
C17 C 0.6949(3) 0.60870(15) 0.8426(2) 0.0267(4) Uani 1 1 d . . . . .
H17 H 0.6727 0.6696 0.8669 0.032 Uiso 1 1 calc R . . . .
C3 C 0.1136(2) 0.77456(16) 0.88922(19) 0.0247(4) Uani 1 1 d . . . . .
C18 C 0.6366(2) 0.53015(15) 0.90183(19) 0.0246(4) Uani 1 1 d . . . . .
C13 C 0.0021(3) 0.76569(18) 1.0011(2) 0.0312(4) Uani 1 1 d . . . . .
H13A H -0.0259 0.7016 1.0119 0.047 Uiso 1 1 calc GR . . . .
H13B H -0.0886 0.8016 0.9807 0.047 Uiso 1 1 calc GR . . . .
H13C H 0.0490 0.7881 1.0829 0.047 Uiso 1 1 calc GR . . . .
C29 C 0.5247(3) 0.52136(18) 1.0128(2) 0.0312(5) Uani 1 1 d . . . . .
H29A H 0.4220 0.5162 0.9760 0.047 Uiso 1 1 calc GR . . . .
H29B H 0.5312 0.5753 1.0694 0.047 Uiso 1 1 calc GR . . . .
H29C H 0.5485 0.4669 1.0649 0.047 Uiso 1 1 calc GR . . . .
H33A H 0.316(4) 0.341(2) 0.864(3) 0.079(12) Uiso 1 1 d D . . . .
H14 H 0.345(3) 0.412(2) 0.673(3) 0.070(12) Uiso 1 1 d D . . . .
H33B H 0.207(3) 0.4153(18) 0.858(3) 0.048(9) Uiso 1 1 d D . . . .
H34A H 0.778(4) 0.100(2) 0.853(3) 0.059(10) Uiso 1 1 d D . . . .
H34B H 0.664(3) 0.171(2) 0.832(3) 0.063(11) Uiso 1 1 d 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
O14 C8 1.297(3) . ?
O14 H14 0.8202(15) . ?
O12 C1 1.250(3) . ?
O28 C21 1.243(3) . ?
O30 H30 0.8200 . ?
O30 C24 1.304(3) . ?
O34 H34A 0.85(3) . ?
O34 H34B 0.89(2) . ?
O33 H33A 0.97(3) . ?
O33 H33B 0.88(2) . ?
N23 C24 1.345(3) . ?
N23 C22 1.314(3) . ?
N7 C8 1.350(3) . ?
N7 C6 1.312(3) . ?
N27 H27 0.8600 . ?
N27 C26 1.373(3) . ?
N27 C22 1.349(3) . ?
N11 H11 0.8600 . ?
N11 C10 1.374(3) . ?
N11 C6 1.348(3) . ?
N5 N4 1.374(2) . ?
N5 C1 1.427(2) . ?
N5 C6 1.366(3) . ?
N4 H4 0.8600 . ?
N4 C3 1.342(3) . ?
N20 N19 1.378(2) . ?
N20 C22 1.363(3) . ?
N20 C21 1.423(3) . ?
N19 H19 0.8600 . ?
N19 C18 1.343(3) . ?
C8 C9 1.414(3) . ?
C24 C25 1.416(3) . ?
C10 C9 1.357(3) . ?
C10 C15 1.492(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.354(3) . ?
C9 H9 0.9300 . ?
C26 C31 1.501(3) . ?
C1 C2 1.404(3) . ?
C21 C17 1.416(3) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C32 C31 1.522(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.515(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C2 H2 0.9300 . ?
C2 C3 1.374(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(3) . ?
C3 C13 1.489(3) . ?
C18 C29 1.485(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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
C8 O14 H14 116(2) . . ?
C24 O30 H30 109.5 . . ?
H34A O34 H34B 111(3) . . ?
H33A O33 H33B 102(2) . . ?
C22 N23 C24 115.56(18) . . ?
C6 N7 C8 115.52(17) . . ?
C26 N27 H27 120.1 . . ?
C22 N27 H27 120.1 . . ?
C22 N27 C26 119.88(17) . . ?
C10 N11 H11 120.0 . . ?
C6 N11 H11 120.0 . . ?
C6 N11 C10 119.95(17) . . ?
N4 N5 C1 109.27(17) . . ?
C6 N5 N4 122.09(17) . . ?
C6 N5 C1 128.64(19) . . ?
N5 N4 H4 126.2 . . ?
C3 N4 N5 107.69(17) . . ?
C3 N4 H4 126.2 . . ?
N19 N20 C21 109.55(17) . . ?
C22 N20 N19 122.03(17) . . ?
C22 N20 C21 128.42(19) . . ?
N20 N19 H19 126.2 . . ?
C18 N19 N20 107.59(17) . . ?
C18 N19 H19 126.2 . . ?
O14 C8 N7 118.43(17) . . ?
O14 C8 C9 118.73(18) . . ?
N7 C8 C9 122.83(19) . . ?
O30 C24 N23 118.11(18) . . ?
O30 C24 C25 118.98(18) . . ?
N23 C24 C25 122.90(19) . . ?
N11 C10 C15 115.86(18) . . ?
C9 C10 N11 117.91(18) . . ?
C9 C10 C15 126.2(2) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 C24 118.44(19) . . ?
C26 C25 H25 120.8 . . ?
C8 C9 H9 120.8 . . ?
C10 C9 C8 118.47(19) . . ?
C10 C9 H9 120.8 . . ?
N27 C26 C31 115.94(17) . . ?
C25 C26 N27 118.02(18) . . ?
C25 C26 C31 126.00(19) . . ?
N23 C22 N27 125.19(19) . . ?
N23 C22 N20 119.02(18) . . ?
N27 C22 N20 115.79(18) . . ?
O12 C1 N5 120.6(2) . . ?
O12 C1 C2 135.0(2) . . ?
C2 C1 N5 104.34(19) . . ?
O28 C21 N20 120.9(2) . . ?
O28 C21 C17 135.0(2) . . ?
C17 C21 N20 104.15(19) . . ?
N7 C6 N11 125.30(19) . . ?
N7 C6 N5 119.27(19) . . ?
N11 C6 N5 115.42(18) . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
C10 C15 H15A 108.6 . . ?
C10 C15 H15B 108.6 . . ?
C10 C15 C16 114.80(18) . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C26 C31 C32 114.57(17) . . ?
C26 C31 H31A 108.6 . . ?
C26 C31 H31B 108.6 . . ?
C32 C31 H31A 108.6 . . ?
C32 C31 H31B 108.6 . . ?
H31A C31 H31B 107.6 . . ?
C1 C2 H2 125.8 . . ?
C3 C2 C1 108.44(18) . . ?
C3 C2 H2 125.8 . . ?
C21 C17 H17 125.9 . . ?
C18 C17 C21 108.27(18) . . ?
C18 C17 H17 125.9 . . ?
N4 C3 C2 110.26(17) . . ?
N4 C3 C13 120.0(2) . . ?
C2 C3 C13 129.8(2) . . ?
N19 C18 C17 110.41(17) . . ?
N19 C18 C29 120.1(2) . . ?
C17 C18 C29 129.5(2) . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C18 C29 H29A 109.5 . . ?
C18 C29 H29B 109.5 . . ?
C18 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

_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 1.640
_oxdiff_exptl_absorpt_empirical_full_min 0.815
