#------------------------------------------------------------------------------
#$Date: 2025-11-29 20:06:04 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303682 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/09/7250988.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7250988
loop_
_publ_author_name
'Marasinghe, Aloka A.'
'Averkiev, Boris B.'
'Aakeröy, Christer B.'
_publ_section_title
;
 Examining intermolecular interactions in crystal structures of
 amide-substituted 2-aminopyrimidine derivatives
;
_journal_issue                   43
_journal_name_full               CrystEngComm
_journal_page_first              7000
_journal_page_last               7011
_journal_paper_doi               10.1039/D5CE00839E
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C9 H12 Cl N3 O'
_chemical_formula_sum            'C9 H12 Cl N3 O'
_chemical_formula_weight         213.67
_chemical_melting_point          375.0(10)
_chemical_name_systematic        N-(5-chloropyrimidin-2-yl)pentanamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-22
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2025-08-25 deposited with the CCDC.	2025-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.8219(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.51521(9)
_cell_length_b                   26.9519(2)
_cell_length_c                   9.59636(7)
_cell_measurement_reflns_used    14939
_cell_measurement_temperature    240.00(10)
_cell_measurement_theta_max      78.7290
_cell_measurement_theta_min      4.9510
_cell_volume                     2170.09(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.133a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.133a 64-bit (release 07-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.133a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      240.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00 -67.00   0.50    0.50    --  -49.79-143.00 121.00   66
  2  ω    -85.00 -17.00   0.50    0.50    --  -49.79 127.00   6.00  136
  3  ω   -110.00 -82.00   0.50    0.50    --  -49.79-127.00 -68.00   56
  4  ω     57.00  82.00   0.50    0.50    --   49.79-127.00 -68.00   50
  5  ω     75.00 102.00   0.50    0.50    --   49.79-143.00 121.00   54
  6  ω    -78.00 -53.00   0.50    4.00    --  -90.00 127.00   6.00   50
  7  ω    -85.00 -60.00   0.50    4.00    --  -90.00 143.00 176.00   50
  8  ω     69.00 125.00   0.50    4.00    --  111.50-143.00 121.00  112
  9  ω    103.00 128.00   0.50    4.00    --  111.50 143.00 176.00   50
 10  ω     85.00 113.00   0.50    4.00    --  111.50-127.00 -68.00   56
 11  ω     51.00  77.00   0.50    4.00    --  111.50-127.00 -68.00   52
 12  ω    -26.00  18.00   0.50    0.50    --  -49.79  19.00 -90.00   88
 13  ω    -17.00  20.00   0.50    0.50    --  -49.79  19.00 -60.00   74
 14  ω    -26.00  24.00   0.50    0.50    --  -49.79  19.00-150.00  100
 15  ω   -140.00-115.00   0.50    4.00    --  -90.00-127.00 -68.00   50
 16  ω    -47.00 -18.00   0.50    4.00    --  -90.00  45.00-120.00   58
 17  ω     41.00  68.00   0.50    4.00    --  111.50 -61.00  60.00   54
 18  ω     71.00  97.00   0.50    4.00    --  111.50-125.00   0.00   52
 19  ω     42.00  68.00   0.50    4.00    --  111.50 -77.00  90.00   52
 20  ω     83.00 111.00   0.50    4.00    --  111.50-125.00 -30.00   56
 21  ω     44.00  70.00   0.50    4.00    --  111.50-125.00 -30.00   52
 22  ω     71.00 106.00   0.50    4.00    --  111.50-125.00 120.00   70
 23  ω     75.00 101.00   0.50    4.00    --  111.50 -94.00  90.00   52
 24  ω    120.00 162.00   0.50    4.00    --  111.50 125.00  30.00   84
 25  ω    103.00 155.00   0.50    4.00    --  111.50  45.00 120.00  104
 26  ω    152.00 178.00   0.50    4.00    --  111.50  30.00   0.00   52
 27  ω    105.00 178.00   0.50    4.00    --  111.50  30.00  30.00  146
 28  ω     82.00 111.00   0.50    4.00    --  111.50-125.00  30.00   58
 29  ω     44.00  69.00   0.50    4.00    --  111.50 -61.00 -30.00   50
 30  ω    112.00 174.00   0.50    4.00    --  111.50  61.00 -60.00  124
 31  ω     42.00  67.00   0.50    4.00    --  111.50 -61.00 -60.00   50
 32  ω     47.00  72.00   0.50    4.00    --  111.50 -77.00 120.00   50
 33  ω     62.00  88.00   0.50    4.00    --  111.50 -94.00-150.00   52
 34  ω     60.00  96.00   0.50    4.00    --  111.50 -77.00 -60.00   72
 35  ω     41.00  66.00   0.50    4.00    --  111.50 -61.00 150.00   50
 36  ω     47.00  72.00   0.50    4.00    --  111.50-125.00 -60.00   50
 37  ω     79.00 111.00   0.50    4.00    --  111.50-125.00 -60.00   64
 38  ω     54.00 103.00   0.50    4.00    --  111.50 -77.00   0.00   98
 39  ω     77.00 103.00   0.50    4.00    --  111.50 -77.00  60.00   52
 40  ω     43.00  79.00   0.50    4.00    --  111.50-125.00 -90.00   72
 41  ω     85.00 134.00   0.50    4.00    --  111.50 -82.00-105.83   98
 42  ω     48.00  77.00   0.50    4.00    --  111.50-125.00  30.00   58
 43  ω    152.00 178.00   0.50    4.00    --  111.50  15.00 -30.00   52
 44  ω    107.00 133.00   0.50    4.00    --  111.50  15.00 -30.00   52
 45  ω     55.00  85.00   0.50    4.00    --  111.50 -94.00 -30.00   60
 46  ω    140.00 176.00   0.50    4.00    --  111.50  30.00  90.00   72
 47  ω    103.00 143.00   0.50    4.00    --  111.50  45.00 -60.00   80
 48  ω     69.00 105.00   0.50    4.00    --  111.50 -94.00-120.00   72
 49  ω     75.00 101.00   0.50    4.00    --  111.50 -94.00 -90.00   52
 50  ω     44.00  75.00   0.50    4.00    --  111.50 -94.00 -60.00   62
 51  ω     80.00 105.00   0.50    4.00    --  111.50 -94.00 -60.00   50
 52  ω     43.00  76.00   0.50    4.00    --  111.50-125.00  90.00   66
 53  ω    106.00 131.00   0.50    4.00    --  111.50  30.00 -60.00   50
 54  ω    123.00 148.00   0.50    4.00    --  111.50  15.00  60.00   50
 55  ω    124.00 153.00   0.50    4.00    --  111.50  77.00   0.00   58
 56  ω    112.00 147.00   0.50    4.00    --  111.50  30.00   0.00   70
;
_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      0.0922250000
_diffrn_orient_matrix_UB_12      0.0488860000
_diffrn_orient_matrix_UB_13      -0.0065572000
_diffrn_orient_matrix_UB_21      0.1562658000
_diffrn_orient_matrix_UB_22      -0.0294320000
_diffrn_orient_matrix_UB_23      0.0073506000
_diffrn_orient_matrix_UB_31      -0.0280239000
_diffrn_orient_matrix_UB_32      -0.0032955000
_diffrn_orient_matrix_UB_33      -0.1626390000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27544
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.955
_diffrn_reflns_theta_min         3.280
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.905
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.133a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_recrystallization_method 'crystallized from ethylacetate'
_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4696
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0466
_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)+(0.0636P)²+0.5694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1325
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4264
_reflns_number_total             4696
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00839e2.cif
_cod_data_source_block           exp_936
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '374-376' was changed to
'375.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7250982--7251002.cif.
;
_cod_database_code               7250988
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12C-C11B = C12B-C11B = C13C-C12C = C12B-C13B
 1.51 with sigma of 0.02
3. Others
 Sof(H11C)=Sof(H11D)=Sof(C12C)=Sof(H12C)=Sof(H12D)=Sof(C13C)=Sof(H13D)=
 Sof(H13E)=Sof(H13F)=1-FVAR(1)
 Sof(H11A)=Sof(H11B)=Sof(C12B)=Sof(H12A)=Sof(H12B)=Sof(C13B)=Sof(H13A)=
 Sof(H13B)=Sof(H13C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C10A(H10C,H10D), C11A(H11E,H11F), C12A(H12E,H12F), C10B(H10A,H10B), C11B(H11A,
 H11B), C11B(H11C,H11D), C12B(H12A,H12B), C12C(H12C,H12D)
4.b Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C5A(H5A), C3B(H3B), C5B(H5B)
4.c Idealised Me refined as rotating group:
 C13A(H13G,H13H,H13I), C13B(H13A,H13B,H13C), C13C(H13D,H13E,H13F)
;
_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 1.249
_oxdiff_exptl_absorpt_empirical_full_min 0.796
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Cl1A Cl -0.13653(7) 0.36297(2) 0.83833(6) 0.08051(18) Uani 1 1 d . . . . .
C1A C 0.1282(2) 0.48519(7) 0.69064(18) 0.0543(4) Uani 1 1 d . . . . .
N2A N 0.0920(2) 0.44667(6) 0.60235(16) 0.0639(4) Uani 1 1 d . . . . .
C3A C 0.0098(2) 0.41030(7) 0.6488(2) 0.0659(5) Uani 1 1 d . . . . .
H3A H -0.018549 0.382555 0.590607 0.079 Uiso 1 1 calc R U . . .
C4A C -0.0353(2) 0.41194(7) 0.7794(2) 0.0600(4) Uani 1 1 d . . . . .
C5A C 0.0034(2) 0.45354(7) 0.8601(2) 0.0604(4) Uani 1 1 d . . . . .
H5A H -0.029009 0.455764 0.948797 0.072 Uiso 1 1 calc R U . . .
N6A N 0.08570(18) 0.49100(6) 0.81674(15) 0.0568(3) Uani 1 1 d . . . . .
N7A N 0.21855(18) 0.52070(6) 0.63649(16) 0.0579(3) Uani 1 1 d . . . . .
H7A H 0.243(3) 0.5127(8) 0.559(2) 0.067(6) Uiso 1 1 d . . . . .
C8A C 0.2748(2) 0.56650(7) 0.68149(19) 0.0586(4) Uani 1 1 d . . . . .
O9A O 0.35381(19) 0.58888(6) 0.60634(15) 0.0746(4) Uani 1 1 d . . . . .
C10A C 0.2441(3) 0.58806(8) 0.8187(2) 0.0659(5) Uani 1 1 d . . . . .
H10C H 0.298131 0.567772 0.897269 0.079 Uiso 1 1 calc R U . . .
H10D H 0.129479 0.587047 0.820758 0.079 Uiso 1 1 calc R U . . .
C11A C 0.3026(3) 0.64143(9) 0.8387(3) 0.0821(6) Uani 1 1 d . . . . .
H11E H 0.311933 0.650449 0.938738 0.099 Uiso 1 1 calc R U . . .
H11F H 0.408918 0.643858 0.812997 0.099 Uiso 1 1 calc R U . . .
C12A C 0.1931(4) 0.67749(11) 0.7510(5) 0.1231(12) Uani 1 1 d . . . . .
H12E H 0.087441 0.675496 0.778133 0.148 Uiso 1 1 calc R U . . .
H12F H 0.182002 0.667982 0.651192 0.148 Uiso 1 1 calc R U . . .
C13A C 0.2522(7) 0.73063(14) 0.7679(7) 0.203(3) Uani 1 1 d . . . . .
H13G H 0.354570 0.733186 0.736941 0.305 Uiso 1 1 calc R U . . .
H13H H 0.263644 0.740269 0.866459 0.305 Uiso 1 1 calc R U . . .
H13I H 0.176155 0.752395 0.710968 0.305 Uiso 1 1 calc R U . . .
Cl1B Cl 0.21927(7) 0.37535(2) 0.12047(6) 0.07607(17) Uani 1 1 d . . . . .
C1B C 0.3962(2) 0.52058(7) 0.27934(17) 0.0548(4) Uani 1 1 d . . . . .
N2B N 0.31296(18) 0.49382(6) 0.36053(15) 0.0587(3) Uani 1 1 d . . . . .
C3B C 0.2594(2) 0.45011(7) 0.30969(19) 0.0606(4) Uani 1 1 d . . . . .
H3B H 0.201056 0.430220 0.363107 0.073 Uiso 1 1 calc R U . . .
C4B C 0.2868(2) 0.43313(7) 0.18127(19) 0.0581(4) Uani 1 1 d . . . . .
C5B C 0.3703(2) 0.46337(7) 0.10383(18) 0.0597(4) Uani 1 1 d . . . . .
H5B H 0.388852 0.452616 0.014876 0.072 Uiso 1 1 calc R U . . .
N6B N 0.42531(19) 0.50750(6) 0.15236(15) 0.0598(4) Uani 1 1 d . . . . .
N7B N 0.4508(2) 0.56512(6) 0.33939(17) 0.0610(4) Uani 1 1 d . . . . .
H7B H 0.426(3) 0.5709(8) 0.420(2) 0.069(6) Uiso 1 1 d . . . . .
C8B C 0.5386(2) 0.60155(7) 0.2877(2) 0.0639(4) Uani 1 1 d . . . . .
O9B O 0.5894(2) 0.59851(6) 0.17846(17) 0.0860(5) Uani 1 1 d . . . . .
C10B C 0.5684(3) 0.64586(9) 0.3840(3) 0.0853(6) Uani 1 1 d . . . . .
H10A H 0.465142 0.660132 0.394400 0.102 Uiso 1 1 calc R U . . .
H10B H 0.619828 0.634376 0.477607 0.102 Uiso 1 1 calc R U . . .
C11B C 0.6643(5) 0.68431(13) 0.3394(6) 0.158(2) Uani 1 1 d D . . . .
H11A H 0.602714 0.702490 0.259905 0.189 Uiso 0.618(15) 1 calc R U P A 1
H11B H 0.757590 0.669747 0.307560 0.189 Uiso 0.618(15) 1 calc R U P A 1
H11C H 0.631635 0.686845 0.236636 0.189 Uiso 0.382(15) 1 calc R U P A 2
H11D H 0.773565 0.671432 0.355117 0.189 Uiso 0.382(15) 1 calc R U P A 2
C12B C 0.7204(13) 0.7212(4) 0.4669(12) 0.145(3) Uani 0.618(15) 1 d D . P A 1
H12A H 0.632932 0.744296 0.472730 0.174 Uiso 0.618(15) 1 calc R U P A 1
H12B H 0.738155 0.701799 0.554590 0.174 Uiso 0.618(15) 1 calc R U P A 1
C13B C 0.8581(11) 0.7491(4) 0.4616(16) 0.202(6) Uani 0.618(15) 1 d D . P A 1
H13A H 0.838417 0.771717 0.381940 0.303 Uiso 0.618(15) 1 calc R U P A 1
H13B H 0.945023 0.726958 0.450570 0.303 Uiso 0.618(15) 1 calc R U P A 1
H13C H 0.886163 0.767842 0.548493 0.303 Uiso 0.618(15) 1 calc R U P A 1
C12C C 0.6762(17) 0.7362(4) 0.3930(15) 0.113(4) Uani 0.382(15) 1 d D . P A 2
H12C H 0.718587 0.758753 0.328349 0.135 Uiso 0.382(15) 1 calc R U P A 2
H12D H 0.573472 0.748698 0.411166 0.135 Uiso 0.382(15) 1 calc R U P A 2
C13C C 0.787(4) 0.7284(6) 0.5218(19) 0.283(17) Uani 0.382(15) 1 d D . P A 2
H13D H 0.871523 0.753057 0.529282 0.425 Uiso 0.382(15) 1 calc R U P A 2
H13E H 0.833399 0.695504 0.520829 0.425 Uiso 0.382(15) 1 calc R U P A 2
H13F H 0.732549 0.731417 0.601987 0.425 Uiso 0.382(15) 1 calc R U P A 2
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0571
0 1 0 0.0399
0 0 -1 0.0893
0 0 1 0.0626
-1 0 0 0.0498
1 0 0 0.0519
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
N2A C1A N7A 112.36(15) . . ?
N6A C1A N2A 126.62(17) . . ?
N6A C1A N7A 121.01(16) . . ?
C3A N2A C1A 115.93(16) . . ?
N2A C3A C4A 121.98(18) . . ?
C3A C4A Cl1A 120.55(15) . . ?
C5A C4A Cl1A 121.76(15) . . ?
C5A C4A C3A 117.69(18) . . ?
N6A C5A C4A 122.04(17) . . ?
C1A N6A C5A 115.68(16) . . ?
C8A N7A C1A 133.88(16) . . ?
N7A C8A C10A 121.48(16) . . ?
O9A C8A N7A 117.15(16) . . ?
O9A C8A C10A 121.35(18) . . ?
C8A C10A C11A 111.93(17) . . ?
C12A C11A C10A 112.4(2) . . ?
C11A C12A C13A 112.8(4) . . ?
N2B C1B N7B 113.42(15) . . ?
N6B C1B N2B 125.83(17) . . ?
N6B C1B N7B 120.74(16) . . ?
C3B N2B C1B 116.38(15) . . ?
N2B C3B C4B 121.76(17) . . ?
C3B C4B Cl1B 120.43(15) . . ?
C3B C4B C5B 118.00(18) . . ?
C5B C4B Cl1B 121.56(14) . . ?
N6B C5B C4B 121.45(17) . . ?
C1B N6B C5B 116.53(16) . . ?
C8B N7B C1B 129.51(16) . . ?
N7B C8B C10B 112.95(18) . . ?
O9B C8B N7B 124.27(19) . . ?
O9B C8B C10B 122.8(2) . . ?
C11B C10B C8B 115.9(2) . . ?
C10B C11B C12B 109.6(5) . . ?
C10B C11B C12C 125.9(6) . . ?
C13B C12B C11B 116.9(9) . . ?
C13C C12C C11B 98.9(10) . . ?
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
Cl1A C4A 1.7236(19) . ?
C1A N2A 1.342(2) . ?
C1A N6A 1.330(2) . ?
C1A N7A 1.383(2) . ?
N2A C3A 1.326(3) . ?
C3A C4A 1.372(3) . ?
C4A C5A 1.371(3) . ?
C5A N6A 1.336(2) . ?
N7A C8A 1.367(3) . ?
C8A O9A 1.226(2) . ?
C8A C10A 1.503(3) . ?
C10A C11A 1.524(3) . ?
C11A C12A 1.502(4) . ?
C12A C13A 1.518(5) . ?
Cl1B C4B 1.7270(19) . ?
C1B N2B 1.348(2) . ?
C1B N6B 1.332(2) . ?
C1B N7B 1.378(2) . ?
N2B C3B 1.326(2) . ?
C3B C4B 1.371(3) . ?
C4B C5B 1.379(3) . ?
C5B N6B 1.333(2) . ?
N7B C8B 1.377(3) . ?
C8B O9B 1.204(2) . ?
C8B C10B 1.505(3) . ?
C10B C11B 1.430(4) . ?
C11B C12B 1.586(8) . ?
C11B C12C 1.488(9) . ?
C12B C13B 1.401(13) . ?
C12C C13C 1.439(16) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N7A H7A N2B 0.83(2) 2.16(2) 2.985(2) 178(2) . yes
N7B H7B O9A 0.85(2) 2.05(2) 2.894(2) 175(2) . yes
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0001 -0.9994 -0.0001 -0.0489 0.0294 0.0033
0.0001 0.9994 0.0001 0.0489 -0.0294 -0.0033
-0.0001 -0.0007 -0.9996 0.0065 -0.0073 0.1626
0.0001 0.0007 0.9996 -0.0065 0.0073 -0.1626
-0.9995 0.0007 -0.0001 -0.0921 -0.1562 0.0280
0.9995 -0.0007 0.0001 0.0921 0.1562 -0.0280
