# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_2Acr-a3_3mal
_database_code_depnum_ccdc_archive 'CCDC 2253806'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2,4,5-trifluoro-6-nitrobenzene-1,3-diamine 18-crown-6 2:1 cocrystal
;
_chemical_name_common            ?
_chemical_melting_point          424.7
_chemical_formula_moiety         '2(C6 H4 F3 N3 O2), C12 H24 O6'
_chemical_formula_sum            'C24 H32 F6 N6 O10'
_chemical_formula_weight         678.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   11.6265(4)
_cell_length_b                   11.6941(6)
_cell_length_c                   12.1146(6)
_cell_angle_alpha                73.313(2)
_cell_angle_beta                 77.9280(10)
_cell_angle_gamma                80.0470(10)
_cell_volume                     1531.64(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9898
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.14

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8997
_exptl_absorpt_correction_T_max  0.9422
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41112
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.197
_diffrn_reflns_theta_max         27.174
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6787
_reflns_number_gt                4918
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0741P)²+0.6005P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6787
_refine_ls_number_parameters     431
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1448
_refine_ls_wR_factor_gt          0.1215
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
F1 F 0.26882(10) 0.65635(13) 0.01787(11) 0.0588(3) Uani 1 1 d . . . . .
O1 O -0.22216(13) 0.64599(18) -0.03070(15) 0.0699(5) Uani 1 1 d . . . . .
N1 N 0.14132(16) 0.64496(17) -0.13456(14) 0.0500(4) Uani 1 1 d D . . . .
H1B H 0.2185(15) 0.654(2) -0.152(2) 0.064(7) Uiso 1 1 d D . . . .
H1A H 0.0955(19) 0.646(2) -0.1840(19) 0.058(7) Uiso 1 1 d D . . . .
C1 C -0.03983(14) 0.64626(14) 0.01254(14) 0.0317(3) Uani 1 1 d . . . . .
O2 O -0.07228(14) 0.63737(14) -0.16551(12) 0.0567(4) Uani 1 1 d . . . . .
N2 N 0.17409(15) 0.67037(17) 0.24200(15) 0.0482(4) Uani 1 1 d D . . . .
H2A H 0.2480(15) 0.685(2) 0.214(2) 0.057(6) Uiso 1 1 d D . . . .
H2B H 0.1386(19) 0.686(2) 0.3091(16) 0.055(6) Uiso 1 1 d D . . . .
F2 F -0.06448(10) 0.66077(11) 0.31317(9) 0.0524(3) Uani 1 1 d . . . . .
C2 C 0.08416(15) 0.64851(14) -0.02594(14) 0.0332(3) Uani 1 1 d . . . . .
F3 F -0.20211(9) 0.64656(13) 0.17283(11) 0.0571(3) Uani 1 1 d . . . . .
C3 C 0.15041(15) 0.65579(16) 0.05436(15) 0.0365(4) Uani 1 1 d . . . . .
N3 N -0.11500(14) 0.64294(13) -0.06436(13) 0.0396(3) Uani 1 1 d . . . . .
C4 C 0.10618(15) 0.66274(15) 0.16757(15) 0.0345(4) Uani 1 1 d . . . . .
C5 C -0.01657(15) 0.65783(15) 0.20224(14) 0.0345(4) Uani 1 1 d . . . . .
C6 C -0.08680(14) 0.65016(14) 0.12914(15) 0.0332(3) Uani 1 1 d . . . . .
O5 O 0.11218(13) 0.97143(12) 0.11082(13) 0.0549(4) Uani 1 1 d . . . . .
O6 O 0.35773(14) 0.90279(15) 0.06062(13) 0.0590(4) Uani 1 1 d . . . . .
O7 O 0.44235(12) 0.67284(14) 0.19613(13) 0.0543(4) Uani 1 1 d . . . . .
O8 O 0.33463(13) 0.59011(12) 0.43419(12) 0.0493(3) Uani 1 1 d . . . . .
O9 O 0.09564(12) 0.69590(12) 0.49393(11) 0.0472(3) Uani 1 1 d . . . . .
O10 O 0.01483(12) 0.91997(13) 0.35178(13) 0.0525(4) Uani 1 1 d . . . . .
C13 C 0.1886(2) 1.04036(19) 0.01860(19) 0.0581(6) Uani 1 1 d . . . . .
H13A H 0.219128 1.096847 0.046806 0.070 Uiso 1 1 calc R U . . .
H13B H 0.145113 1.085701 -0.043570 0.070 Uiso 1 1 calc R U . . .
C14 C 0.2881(2) 0.9590(2) -0.02684(18) 0.0601(6) Uani 1 1 d . . . . .
H14A H 0.257353 0.898694 -0.049533 0.072 Uiso 1 1 calc R U . . .
H14B H 0.336221 1.004723 -0.095288 0.072 Uiso 1 1 calc R U . . .
C15 C 0.45986(19) 0.8311(2) 0.0208(2) 0.0592(6) Uani 1 1 d . . . . .
H15A H 0.514897 0.882081 -0.034882 0.071 Uiso 1 1 calc R U . . .
H15B H 0.438077 0.778316 -0.018260 0.071 Uiso 1 1 calc R U . . .
C16 C 0.51697(18) 0.7586(2) 0.1210(2) 0.0605(6) Uani 1 1 d . . . . .
H16A H 0.592303 0.717337 0.092775 0.073 Uiso 1 1 calc R U . . .
H16B H 0.532038 0.811043 0.164280 0.073 Uiso 1 1 calc R U . . .
C17 C 0.50088(19) 0.5879(2) 0.2834(2) 0.0573(5) Uani 1 1 d . . . . .
H17A H 0.538450 0.629695 0.322137 0.069 Uiso 1 1 calc R U . . .
H17B H 0.561836 0.535585 0.247405 0.069 Uiso 1 1 calc R U . . .
C18 C 0.4130(2) 0.51490(19) 0.3707(2) 0.0586(6) Uani 1 1 d . . . . .
H18A H 0.368702 0.480643 0.331088 0.070 Uiso 1 1 calc R U . . .
H18B H 0.453613 0.449538 0.423785 0.070 Uiso 1 1 calc R U . . .
C19 C 0.2448(2) 0.52854(18) 0.51650(18) 0.0530(5) Uani 1 1 d . . . . .
H19A H 0.280203 0.463642 0.574115 0.064 Uiso 1 1 calc R U . . .
H19B H 0.200309 0.494271 0.477062 0.064 Uiso 1 1 calc R U . . .
C20 C 0.1642(2) 0.61552(19) 0.57516(17) 0.0520(5) Uani 1 1 d . . . . .
H20A H 0.112296 0.572561 0.642174 0.062 Uiso 1 1 calc R U . . .
H20B H 0.210287 0.660269 0.602431 0.062 Uiso 1 1 calc R U . . .
C21 C 0.0252(2) 0.7892(2) 0.54057(18) 0.0568(5) Uani 1 1 d . . . . .
H21A H 0.075954 0.840766 0.552434 0.068 Uiso 1 1 calc R U . . .
H21B H -0.021475 0.754599 0.615480 0.068 Uiso 1 1 calc R U . . .
C22 C -0.05424(19) 0.8605(2) 0.4575(2) 0.0573(5) Uani 1 1 d . . . . .
H22A H -0.101040 0.807860 0.441541 0.069 Uiso 1 1 calc R U . . .
H22B H -0.108005 0.919298 0.491657 0.069 Uiso 1 1 calc R U . . .
C23 C -0.05412(18) 0.97096(19) 0.2618(2) 0.0544(5) Uani 1 1 d . . . . .
H23A H -0.123728 1.020426 0.289796 0.065 Uiso 1 1 calc R U . . .
H23B H -0.080240 0.907475 0.239699 0.065 Uiso 1 1 calc R U . . .
C24 C 0.01748(18) 1.04516(18) 0.1590(2) 0.0518(5) Uani 1 1 d . . . . .
H24A H -0.031929 1.086745 0.100703 0.062 Uiso 1 1 calc R U . . .
H24B H 0.048259 1.105032 0.182334 0.062 Uiso 1 1 calc R U . . .
O3 O 0.69672(15) 1.16064(17) 0.3460(2) 0.0819(6) Uani 1 1 d . . . . .
O4 O 0.59016(15) 1.30193(14) 0.24214(17) 0.0681(5) Uani 1 1 d . . . . .
F4 F 0.22796(10) 1.11159(11) 0.26480(12) 0.0556(3) Uani 1 1 d . . . . .
N4 N 0.37433(16) 1.27401(15) 0.23007(17) 0.0540(4) Uani 1 1 d . . . . .
H4B H 0.304743 1.293423 0.211542 0.065 Uiso 1 1 calc R U . . .
H4A H 0.419982 1.328539 0.217688 0.065 Uiso 1 1 calc R U . . .
N5 N 0.28363(15) 0.87078(15) 0.36028(16) 0.0499(4) Uani 1 1 d . . . . .
H5A H 0.215387 0.895409 0.339400 0.060 Uiso 1 1 calc R U . . .
H5B H 0.302785 0.795536 0.390613 0.060 Uiso 1 1 calc R U . . .
F5 F 0.50095(11) 0.79505(10) 0.42958(12) 0.0596(3) Uani 1 1 d . . . . .
F6 F 0.65509(10) 0.94577(11) 0.39965(13) 0.0622(3) Uani 1 1 d . . . . .
N6 N 0.60786(14) 1.19584(15) 0.30024(15) 0.0458(4) Uani 1 1 d . . . . .
C7 C 0.52400(15) 1.11575(16) 0.31453(15) 0.0361(4) Uani 1 1 d . . . . .
C8 C 0.41188(15) 1.15798(16) 0.27857(15) 0.0362(4) Uani 1 1 d . . . . .
C9 C 0.33600(15) 1.07162(16) 0.29759(15) 0.0373(4) Uani 1 1 d . . . . .
C10 C 0.36033(15) 0.94985(16) 0.34551(15) 0.0369(4) Uani 1 1 d . . . . .
C11 C 0.47243(16) 0.91313(16) 0.37996(16) 0.0391(4) Uani 1 1 d . . . . .
C12 C 0.55085(15) 0.99170(17) 0.36546(16) 0.0388(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.356(2) . ?
O1 N3 1.225(2) . ?
N1 C2 1.353(2) . ?
N1 H1B 0.896(16) . ?
N1 H1A 0.878(16) . ?
C1 C6 1.415(2) . ?
C1 N3 1.416(2) . ?
C1 C2 1.422(2) . ?
O2 N3 1.238(2) . ?
N2 C4 1.346(2) . ?
N2 H2A 0.883(16) . ?
N2 H2B 0.887(16) . ?
F2 C5 1.3507(19) . ?
C2 C3 1.389(2) . ?
F3 C6 1.3376(19) . ?
C3 C4 1.381(2) . ?
C4 C5 1.407(2) . ?
C5 C6 1.354(2) . ?
O5 C13 1.415(3) . ?
O5 C24 1.410(3) . ?
O6 C14 1.409(3) . ?
O6 C15 1.412(3) . ?
O7 C17 1.426(3) . ?
O7 C16 1.426(3) . ?
O8 C18 1.419(3) . ?
O8 C19 1.420(3) . ?
O9 C20 1.423(2) . ?
O9 C21 1.425(2) . ?
O10 C23 1.419(3) . ?
O10 C22 1.422(3) . ?
C13 C14 1.483(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.478(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.490(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.492(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.484(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.481(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
O3 N6 1.227(2) . ?
O4 N6 1.244(2) . ?
F4 C9 1.3613(19) . ?
N4 C8 1.350(2) . ?
N4 H4B 0.8600 . ?
N4 H4A 0.8600 . ?
N5 C10 1.344(2) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
F5 C11 1.351(2) . ?
F6 C12 1.337(2) . ?
N6 C7 1.418(2) . ?
C7 C12 1.412(3) . ?
C7 C8 1.423(2) . ?
C8 C9 1.393(2) . ?
C9 C10 1.378(3) . ?
C10 C11 1.410(2) . ?
C11 C12 1.355(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
C2 N1 H1B 117.7(16) . . ?
C2 N1 H1A 115.2(16) . . ?
H1B N1 H1A 126(2) . . ?
C6 C1 N3 120.71(15) . . ?
C6 C1 C2 118.25(15) . . ?
N3 C1 C2 121.03(15) . . ?
C4 N2 H2A 118.5(16) . . ?
C4 N2 H2B 118.5(15) . . ?
H2A N2 H2B 119(2) . . ?
N1 C2 C3 118.19(16) . . ?
N1 C2 C1 124.77(16) . . ?
C3 C2 C1 117.04(15) . . ?
F1 C3 C4 117.37(15) . . ?
F1 C3 C2 116.89(15) . . ?
C4 C3 C2 125.74(15) . . ?
O1 N3 O2 120.17(16) . . ?
O1 N3 C1 119.90(16) . . ?
O2 N3 C1 119.93(15) . . ?
N2 C4 C3 123.52(16) . . ?
N2 C4 C5 121.39(16) . . ?
C3 C4 C5 115.07(15) . . ?
F2 C5 C6 119.64(15) . . ?
F2 C5 C4 117.80(15) . . ?
C6 C5 C4 122.56(15) . . ?
F3 C6 C5 116.63(15) . . ?
F3 C6 C1 122.06(15) . . ?
C5 C6 C1 121.31(15) . . ?
C13 O5 C24 111.52(16) . . ?
C14 O6 C15 112.68(17) . . ?
C17 O7 C16 112.35(16) . . ?
C18 O8 C19 112.62(16) . . ?
C20 O9 C21 111.92(15) . . ?
C23 O10 C22 111.78(16) . . ?
O5 C13 C14 109.38(17) . . ?
O5 C13 H13A 109.8 . . ?
C14 C13 H13A 109.8 . . ?
O5 C13 H13B 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
O6 C14 C13 109.34(18) . . ?
O6 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
O6 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
O6 C15 C16 109.69(18) . . ?
O6 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
O6 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
O7 C16 C15 110.13(17) . . ?
O7 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
O7 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
O7 C17 C18 109.50(17) . . ?
O7 C17 H17A 109.8 . . ?
C18 C17 H17A 109.8 . . ?
O7 C17 H17B 109.8 . . ?
C18 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
O8 C18 C17 108.90(17) . . ?
O8 C18 H18A 109.9 . . ?
C17 C18 H18A 109.9 . . ?
O8 C18 H18B 109.9 . . ?
C17 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
O8 C19 C20 108.78(16) . . ?
O8 C19 H19A 109.9 . . ?
C20 C19 H19A 109.9 . . ?
O8 C19 H19B 109.9 . . ?
C20 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
O9 C20 C19 108.97(16) . . ?
O9 C20 H20A 109.9 . . ?
C19 C20 H20A 109.9 . . ?
O9 C20 H20B 109.9 . . ?
C19 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
O9 C21 C22 109.02(17) . . ?
O9 C21 H21A 109.9 . . ?
C22 C21 H21A 109.9 . . ?
O9 C21 H21B 109.9 . . ?
C22 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
O10 C22 C21 109.45(17) . . ?
O10 C22 H22A 109.8 . . ?
C21 C22 H22A 109.8 . . ?
O10 C22 H22B 109.8 . . ?
C21 C22 H22B 109.8 . . ?
H22A C22 H22B 108.2 . . ?
O10 C23 C24 109.68(16) . . ?
O10 C23 H23A 109.7 . . ?
C24 C23 H23A 109.7 . . ?
O10 C23 H23B 109.7 . . ?
C24 C23 H23B 109.7 . . ?
H23A C23 H23B 108.2 . . ?
O5 C24 C23 109.90(16) . . ?
O5 C24 H24A 109.7 . . ?
C23 C24 H24A 109.7 . . ?
O5 C24 H24B 109.7 . . ?
C23 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
C8 N4 H4B 120.0 . . ?
C8 N4 H4A 120.0 . . ?
H4B N4 H4A 120.0 . . ?
C10 N5 H5A 120.0 . . ?
C10 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
O3 N6 O4 120.41(16) . . ?
O3 N6 C7 119.96(17) . . ?
O4 N6 C7 119.63(16) . . ?
C12 C7 C8 118.76(15) . . ?
C12 C7 N6 120.07(16) . . ?
C8 C7 N6 121.17(16) . . ?
N4 C8 C9 118.73(16) . . ?
N4 C8 C7 124.91(16) . . ?
C9 C8 C7 116.35(16) . . ?
F4 C9 C10 117.12(15) . . ?
F4 C9 C8 116.68(16) . . ?
C10 C9 C8 126.20(16) . . ?
N5 C10 C9 123.33(16) . . ?
N5 C10 C11 121.66(17) . . ?
C9 C10 C11 115.00(15) . . ?
F5 C11 C12 119.66(16) . . ?
F5 C11 C10 117.96(16) . . ?
C12 C11 C10 122.38(16) . . ?
F6 C12 C11 116.83(16) . . ?
F6 C12 C7 121.87(16) . . ?
C11 C12 C7 121.30(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 N1 179.79(16) . . . . ?
N3 C1 C2 N1 -1.6(3) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
N3 C1 C2 C3 177.90(15) . . . . ?
N1 C2 C3 F1 -1.3(2) . . . . ?
C1 C2 C3 F1 179.17(15) . . . . ?
N1 C2 C3 C4 178.56(17) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C6 C1 N3 O1 1.5(2) . . . . ?
C2 C1 N3 O1 -177.03(17) . . . . ?
C6 C1 N3 O2 -178.70(15) . . . . ?
C2 C1 N3 O2 2.7(2) . . . . ?
F1 C3 C4 N2 0.3(3) . . . . ?
C2 C3 C4 N2 -179.59(17) . . . . ?
F1 C3 C4 C5 -178.00(15) . . . . ?
C2 C3 C4 C5 2.2(3) . . . . ?
N2 C4 C5 F2 -0.1(3) . . . . ?
C3 C4 C5 F2 178.16(15) . . . . ?
N2 C4 C5 C6 179.99(17) . . . . ?
C3 C4 C5 C6 -1.7(2) . . . . ?
F2 C5 C6 F3 0.4(2) . . . . ?
C4 C5 C6 F3 -179.77(15) . . . . ?
F2 C5 C6 C1 -179.68(15) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
N3 C1 C6 F3 2.4(2) . . . . ?
C2 C1 C6 F3 -178.97(15) . . . . ?
N3 C1 C6 C5 -177.53(15) . . . . ?
C2 C1 C6 C5 1.1(2) . . . . ?
C24 O5 C13 C14 178.52(17) . . . . ?
C15 O6 C14 C13 -175.25(18) . . . . ?
O5 C13 C14 O6 -65.4(2) . . . . ?
C14 O6 C15 C16 -170.11(19) . . . . ?
C17 O7 C16 C15 170.38(18) . . . . ?
O6 C15 C16 O7 66.6(2) . . . . ?
C16 O7 C17 C18 170.23(18) . . . . ?
C19 O8 C18 C17 177.70(17) . . . . ?
O7 C17 C18 O8 -67.7(2) . . . . ?
C18 O8 C19 C20 -177.66(17) . . . . ?
C21 O9 C20 C19 -174.03(17) . . . . ?
O8 C19 C20 O9 71.1(2) . . . . ?
C20 O9 C21 C22 -173.23(17) . . . . ?
C23 O10 C22 C21 168.97(18) . . . . ?
O9 C21 C22 O10 -65.0(2) . . . . ?
C22 O10 C23 C24 172.53(18) . . . . ?
C13 O5 C24 C23 -174.88(17) . . . . ?
O10 C23 C24 O5 65.3(2) . . . . ?
O3 N6 C7 C12 -9.9(3) . . . . ?
O4 N6 C7 C12 170.83(18) . . . . ?
O3 N6 C7 C8 169.98(19) . . . . ?
O4 N6 C7 C8 -9.3(3) . . . . ?
C12 C7 C8 N4 179.21(17) . . . . ?
N6 C7 C8 N4 -0.6(3) . . . . ?
C12 C7 C8 C9 0.3(2) . . . . ?
N6 C7 C8 C9 -179.51(16) . . . . ?
N4 C8 C9 F4 0.2(3) . . . . ?
C7 C8 C9 F4 179.17(15) . . . . ?
N4 C8 C9 C10 179.71(18) . . . . ?
C7 C8 C9 C10 -1.4(3) . . . . ?
F4 C9 C10 N5 0.3(3) . . . . ?
C8 C9 C10 N5 -179.15(18) . . . . ?
F4 C9 C10 C11 -178.93(15) . . . . ?
C8 C9 C10 C11 1.6(3) . . . . ?
N5 C10 C11 F5 -0.4(3) . . . . ?
C9 C10 C11 F5 178.82(16) . . . . ?
N5 C10 C11 C12 179.87(17) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
F5 C11 C12 F6 1.5(3) . . . . ?
C10 C11 C12 F6 -178.82(16) . . . . ?
F5 C11 C12 C7 -179.68(16) . . . . ?
C10 C11 C12 C7 0.0(3) . . . . ?
C8 C7 C12 F6 179.04(16) . . . . ?
N6 C7 C12 F6 -1.1(3) . . . . ?
C8 C7 C12 C11 0.3(3) . . . . ?
N6 C7 C12 C11 -179.88(17) . . . . ?

_refine_diff_density_max         0.853
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.043


####################################################################### 
# 
# 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_Ccr-a16_1mal
_database_code_depnum_ccdc_archive 'CCDC 2253810'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
4-fluoro-6-nitrobenzene-1,3-diamine 18-crown-6 1:1 cocrystal
;
_chemical_name_common            ?
_chemical_melting_point          413.8
_chemical_formula_moiety         'C6 H6 F N3 O2, C12 H24 O6'
_chemical_formula_sum            'C18 H30 F N3 O8'
_chemical_formula_weight         435.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   14.0576(5)
_cell_length_b                   11.0469(3)
_cell_length_c                   15.0431(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.343(2)
_cell_angle_gamma                90
_cell_volume                     2175.87(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8829
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      26.61

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.640
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8926
_exptl_absorpt_correction_T_max  0.9422
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20815
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.412
_diffrn_reflns_theta_max         27.971
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.952
_reflns_number_total             4900
_reflns_number_gt                4074
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_max     0.875
_reflns_Friedel_fraction_full    0.905

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+0.5147P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1618 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4900
_refine_ls_number_parameters     287
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0800
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.012
_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
F1 F 0.54816(14) 0.28119(16) 0.45044(13) 0.0700(5) Uani 1 1 d . . . . .
O1 O 0.4228(2) 0.48349(17) 0.6697(2) 0.0864(8) Uani 1 1 d . . . . .
N1 N 0.3768(2) 0.1150(2) 0.70254(18) 0.0544(6) Uani 1 1 d D . . . .
H1A H 0.368(3) 0.169(2) 0.743(2) 0.071(10) Uiso 1 1 d D . . . .
H1B H 0.383(2) 0.0352(13) 0.710(2) 0.063(9) Uiso 1 1 d D . . . .
C1 C 0.43194(16) 0.28650(19) 0.62894(16) 0.0335(5) Uani 1 1 d . . . . .
C2 C 0.41688(17) 0.16092(19) 0.64045(16) 0.0344(5) Uani 1 1 d . . . . .
O2 O 0.36069(19) 0.3479(2) 0.73649(16) 0.0706(6) Uani 1 1 d . . . . .
N2 N 0.5155(2) 0.0395(2) 0.46158(19) 0.0550(6) Uani 1 1 d D . . . .
H2B H 0.534(2) 0.076(3) 0.4175(19) 0.066(10) Uiso 1 1 d D . . . .
H2A H 0.491(3) -0.0366(17) 0.461(3) 0.083(11) Uiso 1 1 d D . . . .
C3 C 0.44381(17) 0.08162(19) 0.58097(17) 0.0366(5) Uani 1 1 d . . . . .
H3 H 0.432049 -0.000616 0.585367 0.044 Uiso 1 1 calc R U . . .
N3 N 0.40398(17) 0.37659(18) 0.68114(16) 0.0493(5) Uani 1 1 d . . . . .
C4 C 0.48671(16) 0.1179(2) 0.51626(17) 0.0365(5) Uani 1 1 d . . . . .
C5 C 0.50310(18) 0.2436(2) 0.51170(18) 0.0406(5) Uani 1 1 d . . . . .
C6 C 0.47611(17) 0.3245(2) 0.56398(16) 0.0378(5) Uani 1 1 d . . . . .
H6 H 0.486693 0.406560 0.557238 0.045 Uiso 1 1 calc R U . . .
O3 O 0.28355(14) 0.13459(16) 0.87444(13) 0.0509(4) Uani 1 1 d . . . . .
O4 O 0.27818(12) -0.09976(16) 0.78598(13) 0.0480(4) Uani 1 1 d . . . . .
O5 O 0.42834(14) -0.16865(14) 0.71034(14) 0.0475(4) Uani 1 1 d . . . . .
O6 O 0.62250(15) -0.06574(16) 0.81213(14) 0.0521(4) Uani 1 1 d . . . . .
O7 O 0.62788(13) 0.17181(16) 0.90043(13) 0.0505(4) Uani 1 1 d . . . . .
C7 C 0.2176(2) 0.0378(2) 0.8743(2) 0.0512(7) Uani 1 1 d . . . . .
H7A H 0.155528 0.069517 0.879619 0.061 Uiso 1 1 calc R U . . .
H7B H 0.250511 -0.014287 0.928736 0.061 Uiso 1 1 calc R U . . .
O8 O 0.47805(15) 0.23523(15) 0.98003(15) 0.0511(4) Uani 1 1 d . . . . .
C8 C 0.1917(2) -0.0335(3) 0.7846(2) 0.0535(7) Uani 1 1 d . . . . .
H8A H 0.135982 -0.088553 0.778656 0.064 Uiso 1 1 calc R U . . .
H8B H 0.169872 0.020655 0.730069 0.064 Uiso 1 1 calc R U . . .
C9 C 0.2575(2) -0.1726(2) 0.7037(2) 0.0486(6) Uani 1 1 d . . . . .
H9A H 0.240150 -0.121778 0.647447 0.058 Uiso 1 1 calc R U . . .
H9B H 0.200038 -0.225496 0.696308 0.058 Uiso 1 1 calc R U . . .
C10 C 0.3498(2) -0.2463(2) 0.7141(2) 0.0506(6) Uani 1 1 d . . . . .
H10A H 0.372313 -0.289200 0.774433 0.061 Uiso 1 1 calc R U . . .
H10B H 0.333530 -0.305454 0.663045 0.061 Uiso 1 1 calc R U . . .
C11 C 0.5221(2) -0.2312(2) 0.72829(19) 0.0476(6) Uani 1 1 d . . . . .
H11A H 0.513813 -0.289865 0.678018 0.057 Uiso 1 1 calc R U . . .
H11B H 0.540934 -0.274518 0.788357 0.057 Uiso 1 1 calc R U . . .
C12 C 0.6037(2) -0.1442(3) 0.73234(19) 0.0493(6) Uani 1 1 d . . . . .
H12A H 0.665643 -0.187668 0.738270 0.059 Uiso 1 1 calc R U . . .
H12B H 0.582956 -0.097038 0.673969 0.059 Uiso 1 1 calc R U . . .
C13 C 0.6852(2) 0.0337(3) 0.8092(2) 0.0549(7) Uani 1 1 d . . . . .
H13A H 0.648883 0.085192 0.755211 0.066 Uiso 1 1 calc R U . . .
H13B H 0.746572 0.004425 0.801068 0.066 Uiso 1 1 calc R U . . .
C14 C 0.7134(2) 0.1050(3) 0.8993(2) 0.0567(7) Uani 1 1 d . . . . .
H14A H 0.736478 0.050760 0.953702 0.068 Uiso 1 1 calc R U . . .
H14B H 0.768867 0.159953 0.904005 0.068 Uiso 1 1 calc R U . . .
C15 C 0.6492(2) 0.2381(3) 0.9859(2) 0.0579(7) Uani 1 1 d . . . . .
H15A H 0.707552 0.290604 0.995919 0.069 Uiso 1 1 calc R U . . .
H15B H 0.665764 0.182961 1.039575 0.069 Uiso 1 1 calc R U . . .
C16 C 0.5583(2) 0.3120(3) 0.9794(2) 0.0606(8) Uani 1 1 d . . . . .
H16A H 0.576015 0.367528 1.032949 0.073 Uiso 1 1 calc R U . . .
H16B H 0.536377 0.359319 0.921051 0.073 Uiso 1 1 calc R U . . .
C17 C 0.3846(2) 0.2987(2) 0.9598(2) 0.0513(6) Uani 1 1 d . . . . .
H17A H 0.367181 0.341227 0.899479 0.062 Uiso 1 1 calc R U . . .
H17B H 0.391774 0.357954 1.009390 0.062 Uiso 1 1 calc R U . . .
C18 C 0.3024(2) 0.2113(2) 0.95465(19) 0.0499(6) Uani 1 1 d . . . . .
H18A H 0.322916 0.163108 1.012506 0.060 Uiso 1 1 calc R U . . .
H18B H 0.240547 0.254721 0.949109 0.060 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
F1 C5 1.359(3) . ?
O1 N3 1.236(3) . ?
N1 C2 1.353(3) . ?
N1 H1A 0.893(14) . ?
N1 H1B 0.888(13) . ?
C1 C6 1.399(3) . ?
C1 N3 1.409(3) . ?
C1 C2 1.423(3) . ?
C2 C3 1.399(3) . ?
O2 N3 1.238(3) . ?
N2 C4 1.354(3) . ?
N2 H2B 0.894(13) . ?
N2 H2A 0.906(14) . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.413(3) . ?
C5 C6 1.334(3) . ?
C6 H6 0.9300 . ?
O3 C7 1.415(3) . ?
O3 C18 1.418(3) . ?
O4 C8 1.413(3) . ?
O4 C9 1.415(3) . ?
O5 C10 1.415(3) . ?
O5 C11 1.424(3) . ?
O6 C13 1.419(3) . ?
O6 C12 1.425(3) . ?
O7 C15 1.414(4) . ?
O7 C14 1.416(3) . ?
C7 C8 1.489(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
O8 C16 1.415(3) . ?
O8 C17 1.421(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.491(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.481(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.492(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.490(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.487(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

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
C2 N1 H1A 115(2) . . ?
C2 N1 H1B 114(2) . . ?
H1A N1 H1B 128(3) . . ?
C6 C1 N3 117.5(2) . . ?
C6 C1 C2 120.05(19) . . ?
N3 C1 C2 122.4(2) . . ?
N1 C2 C3 119.0(2) . . ?
N1 C2 C1 124.6(2) . . ?
C3 C2 C1 116.5(2) . . ?
C4 N2 H2B 113(2) . . ?
C4 N2 H2A 114(2) . . ?
H2B N2 H2A 129(3) . . ?
C4 C3 C2 124.0(2) . . ?
C4 C3 H3 118.0 . . ?
C2 C3 H3 118.0 . . ?
O1 N3 O2 121.4(2) . . ?
O1 N3 C1 118.7(2) . . ?
O2 N3 C1 119.9(2) . . ?
N2 C4 C3 123.2(2) . . ?
N2 C4 C5 120.6(2) . . ?
C3 C4 C5 116.2(2) . . ?
C6 C5 F1 119.9(2) . . ?
C6 C5 C4 122.9(2) . . ?
F1 C5 C4 117.2(2) . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C7 O3 C18 111.9(2) . . ?
C8 O4 C9 112.3(2) . . ?
C10 O5 C11 112.31(17) . . ?
C13 O6 C12 111.81(19) . . ?
C15 O7 C14 112.4(2) . . ?
O3 C7 C8 110.2(2) . . ?
O3 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
O3 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C16 O8 C17 112.3(2) . . ?
O4 C8 C7 109.6(2) . . ?
O4 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
O4 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
O4 C9 C10 109.0(2) . . ?
O4 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 . . ?
O4 C9 H9B 109.9 . . ?
C10 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
O5 C10 C9 109.09(19) . . ?
O5 C10 H10A 109.9 . . ?
C9 C10 H10A 109.9 . . ?
O5 C10 H10B 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
O5 C11 C12 109.99(19) . . ?
O5 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
O5 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
O6 C12 C11 109.46(19) . . ?
O6 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
O6 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
O6 C13 C14 110.1(2) . . ?
O6 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
O6 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.2 . . ?
O7 C14 C13 109.9(2) . . ?
O7 C14 H14A 109.7 . . ?
C13 C14 H14A 109.7 . . ?
O7 C14 H14B 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
O7 C15 C16 109.3(2) . . ?
O7 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
O7 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
O8 C16 C15 109.8(2) . . ?
O8 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
O8 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
O8 C17 C18 109.3(2) . . ?
O8 C17 H17A 109.8 . . ?
C18 C17 H17A 109.8 . . ?
O8 C17 H17B 109.8 . . ?
C18 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
O3 C18 C17 109.5(2) . . ?
O3 C18 H18A 109.8 . . ?
C17 C18 H18A 109.8 . . ?
O3 C18 H18B 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?

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
C6 C1 C2 N1 178.6(2) . . . . ?
N3 C1 C2 N1 -1.3(4) . . . . ?
C6 C1 C2 C3 -2.9(3) . . . . ?
N3 C1 C2 C3 177.2(2) . . . . ?
N1 C2 C3 C4 -178.9(2) . . . . ?
C1 C2 C3 C4 2.6(3) . . . . ?
C6 C1 N3 O1 -2.5(3) . . . . ?
C2 C1 N3 O1 177.5(3) . . . . ?
C6 C1 N3 O2 176.9(2) . . . . ?
C2 C1 N3 O2 -3.2(4) . . . . ?
C2 C3 C4 N2 177.7(2) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
N2 C4 C5 C6 180.0(3) . . . . ?
C3 C4 C5 C6 -2.2(3) . . . . ?
N2 C4 C5 F1 0.2(3) . . . . ?
C3 C4 C5 F1 178.1(2) . . . . ?
F1 C5 C6 C1 -178.4(2) . . . . ?
C4 C5 C6 C1 1.8(4) . . . . ?
N3 C1 C6 C5 -179.2(2) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
C18 O3 C7 C8 174.6(2) . . . . ?
C9 O4 C8 C7 178.1(2) . . . . ?
O3 C7 C8 O4 71.2(3) . . . . ?
C8 O4 C9 C10 -175.8(2) . . . . ?
C11 O5 C10 C9 174.7(2) . . . . ?
O4 C9 C10 O5 -68.2(3) . . . . ?
C10 O5 C11 C12 -174.8(2) . . . . ?
C13 O6 C12 C11 -168.6(2) . . . . ?
O5 C11 C12 O6 65.0(3) . . . . ?
C12 O6 C13 C14 -173.1(2) . . . . ?
C15 O7 C14 C13 178.0(2) . . . . ?
O6 C13 C14 O7 -73.3(3) . . . . ?
C14 O7 C15 C16 176.4(2) . . . . ?
C17 O8 C16 C15 -171.2(2) . . . . ?
O7 C15 C16 O8 68.7(3) . . . . ?
C16 O8 C17 C18 175.9(2) . . . . ?
C7 O3 C18 C17 170.8(2) . . . . ?
O8 C17 C18 O3 -66.8(3) . . . . ?

_refine_diff_density_max         0.133
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.029


####################################################################### 
# 
# 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_2Bcr-mal149_1
_database_code_depnum_ccdc_archive 'CCDC 2253807'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2,4-difluoro-6-nitrobenzene-1,3-diamine 18-crown-6 2:1 cocrystal
;
_chemical_name_common            ?
_chemical_melting_point          399.2
_chemical_formula_moiety         '2(C6 H5 F2 N3 O2), C12 H24 O6'
_chemical_formula_sum            'C24 H34 F4 N6 O10'
_chemical_formula_weight         642.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   11.4494(6)
_cell_length_b                   11.7343(6)
_cell_length_c                   12.2027(6)
_cell_angle_alpha                73.603(2)
_cell_angle_beta                 77.788(2)
_cell_angle_gamma                79.850(2)
_cell_volume                     1525.26(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      26.88

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8954
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36075
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.191
_diffrn_reflns_theta_max         27.043
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6654
_reflns_number_gt                4559
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0680P)²+0.4045P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6654
_refine_ls_number_parameters     429
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1347
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_restrained_S_all      0.970
_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
F1 F 0.77293(9) 0.15626(12) 0.51675(10) 0.0665(3) Uani 1 1 d . . . . .
N1 N 0.64664(17) 0.14583(16) 0.36108(14) 0.0571(4) Uani 1 1 d D . . . .
H1B H 0.7243(15) 0.155(2) 0.3438(19) 0.070(7) Uiso 1 1 d D . . . .
H1A H 0.6021(18) 0.145(2) 0.3090(18) 0.070(7) Uiso 1 1 d D . . . .
O1 O 0.27700(12) 0.14039(16) 0.46917(14) 0.0716(4) Uani 1 1 d . . . . .
C1 C 0.46262(14) 0.14547(13) 0.50716(13) 0.0376(3) Uani 1 1 d . . . . .
C2 C 0.58763(15) 0.14847(13) 0.46909(13) 0.0388(3) Uani 1 1 d . . . . .
N2 N 0.67224(16) 0.16832(16) 0.73895(14) 0.0559(4) Uani 1 1 d D . . . .
H2B H 0.6333(19) 0.185(2) 0.8045(16) 0.075(7) Uiso 1 1 d D . . . .
H2A H 0.7473(15) 0.183(2) 0.712(2) 0.073(7) Uiso 1 1 d D . . . .
F2 F 0.43018(11) 0.15910(11) 0.80563(9) 0.0630(3) Uani 1 1 d . . . . .
O2 O 0.42691(13) 0.14088(13) 0.32954(11) 0.0609(4) Uani 1 1 d . . . . .
C3 C 0.65231(14) 0.15500(15) 0.55112(14) 0.0420(4) Uani 1 1 d . . . . .
N3 N 0.38558(14) 0.14182(12) 0.43185(13) 0.0467(3) Uani 1 1 d . . . . .
C4 C 0.60515(15) 0.16116(14) 0.66327(14) 0.0409(4) Uani 1 1 d . . . . .
C5 C 0.47962(15) 0.15606(14) 0.69472(13) 0.0414(4) Uani 1 1 d . . . . .
C6 C 0.41002(15) 0.14822(14) 0.62166(14) 0.0411(4) Uani 1 1 d . . . . .
H6 H 0.326097 0.144577 0.647191 0.049 Uiso 1 1 calc R U . . .
F3 F 0.27355(10) 0.39164(10) 0.23546(11) 0.0638(3) Uani 1 1 d . . . . .
O3 O -0.20156(12) 0.34609(14) 0.15242(16) 0.0760(4) Uani 1 1 d . . . . .
F4 F -0.00533(11) 0.70323(9) 0.07158(11) 0.0688(3) Uani 1 1 d . . . . .
N4 N 0.12812(17) 0.22646(15) 0.26744(16) 0.0592(4) Uani 1 1 d D . . . .
H4B H 0.1939(17) 0.211(2) 0.2982(19) 0.074(7) Uiso 1 1 d D . . . .
H4A H 0.0725(19) 0.1741(19) 0.287(2) 0.081(7) Uiso 1 1 d D . . . .
O4 O -0.08965(13) 0.19893(13) 0.24646(14) 0.0669(4) Uani 1 1 d . . . . .
N5 N 0.21426(16) 0.63042(16) 0.14196(16) 0.0567(4) Uani 1 1 d D . . . .
H5A H 0.2814(17) 0.608(2) 0.170(2) 0.077(7) Uiso 1 1 d D . . . .
H5B H 0.187(2) 0.7046(15) 0.1152(19) 0.070(7) Uiso 1 1 d D . . . .
N6 N -0.10866(13) 0.30640(14) 0.19456(14) 0.0506(4) Uani 1 1 d . . . . .
C7 C -0.02335(14) 0.38453(15) 0.18331(14) 0.0400(4) Uani 1 1 d . . . . .
C8 C 0.08933(15) 0.34241(15) 0.21981(14) 0.0405(4) Uani 1 1 d . . . . .
C9 C 0.16418(14) 0.42984(15) 0.20243(14) 0.0425(4) Uani 1 1 d . . . . .
C10 C 0.13754(15) 0.55075(15) 0.15566(14) 0.0425(4) Uani 1 1 d . . . . .
C11 C 0.02334(16) 0.58499(15) 0.12125(15) 0.0452(4) Uani 1 1 d . . . . .
C12 C -0.05446(15) 0.50699(16) 0.13311(15) 0.0455(4) Uani 1 1 d . . . . .
H12 H -0.129841 0.534351 0.107783 0.055 Uiso 1 1 calc R U . . .
O5 O 0.86401(14) 0.39939(14) 0.56252(12) 0.0674(4) Uani 1 1 d . . . . .
O6 O 0.61414(14) 0.46992(12) 0.60982(13) 0.0645(4) Uani 1 1 d . . . . .
O7 O 0.51007(12) 0.41969(13) 0.84787(12) 0.0636(4) Uani 1 1 d . . . . .
O8 O 0.59040(13) 0.19749(12) 0.98988(10) 0.0585(3) Uani 1 1 d . . . . .
O9 O 0.83414(13) 0.09032(11) 0.93320(12) 0.0604(4) Uani 1 1 d . . . . .
O10 O 0.94747(12) 0.17037(13) 0.69757(13) 0.0632(4) Uani 1 1 d . . . . .
C13 C 0.7942(2) 0.4563(2) 0.47525(18) 0.0731(6) Uani 1 1 d . . . . .
H13A H 0.762339 0.395468 0.451447 0.088 Uiso 1 1 calc R U . . .
H13B H 0.844830 0.502289 0.406517 0.088 Uiso 1 1 calc R U . . .
C14 C 0.6933(2) 0.53770(19) 0.52006(18) 0.0709(6) Uani 1 1 d . . . . .
H14A H 0.724887 0.594125 0.550070 0.085 Uiso 1 1 calc R U . . .
H14B H 0.649545 0.584827 0.456689 0.085 Uiso 1 1 calc R U . . .
C15 C 0.51644(19) 0.54322(18) 0.6560(2) 0.0651(6) Uani 1 1 d . . . . .
H15A H 0.466570 0.585193 0.595909 0.078 Uiso 1 1 calc R U . . .
H15B H 0.546476 0.604202 0.681148 0.078 Uiso 1 1 calc R U . . .
C16 C 0.44297(19) 0.4686(2) 0.7559(2) 0.0683(6) Uani 1 1 d . . . . .
H16A H 0.368665 0.517916 0.782598 0.082 Uiso 1 1 calc R U . . .
H16B H 0.419351 0.403039 0.732275 0.082 Uiso 1 1 calc R U . . .
C17 C 0.4385(2) 0.3611(2) 0.9509(2) 0.0724(6) Uani 1 1 d . . . . .
H17A H 0.391821 0.306826 0.933522 0.087 Uiso 1 1 calc R U . . .
H17B H 0.381023 0.420843 0.984639 0.087 Uiso 1 1 calc R U . . .
C18 C 0.5177(2) 0.2914(2) 1.03486(19) 0.0728(6) Uani 1 1 d . . . . .
H18A H 0.569515 0.344255 1.047173 0.087 Uiso 1 1 calc R U . . .
H18B H 0.468199 0.257263 1.110324 0.087 Uiso 1 1 calc R U . . .
C19 C 0.6596(2) 0.11861(19) 1.07096(16) 0.0657(6) Uani 1 1 d . . . . .
H19A H 0.605543 0.075964 1.139001 0.079 Uiso 1 1 calc R U . . .
H19B H 0.707111 0.164775 1.098090 0.079 Uiso 1 1 calc R U . . .
C20 C 0.7416(2) 0.03100(18) 1.01427(18) 0.0672(6) Uani 1 1 d . . . . .
H20A H 0.777311 -0.034633 1.073359 0.081 Uiso 1 1 calc R U . . .
H20B H 0.696023 -0.004070 0.974112 0.081 Uiso 1 1 calc R U . . .
C21 C 0.9136(2) 0.01461(19) 0.8706(2) 0.0712(6) Uani 1 1 d . . . . .
H21A H 0.867885 -0.019230 0.829462 0.085 Uiso 1 1 calc R U . . .
H21B H 0.954508 -0.052435 0.924540 0.085 Uiso 1 1 calc R U . . .
C22 C 1.0042(2) 0.0860(2) 0.7856(2) 0.0709(6) Uani 1 1 d . . . . .
H22A H 1.042023 0.128598 0.825695 0.085 Uiso 1 1 calc R U . . .
H22B H 1.068194 0.032090 0.750245 0.085 Uiso 1 1 calc R U . . .
C23 C 1.02377(18) 0.2548(2) 0.6248(2) 0.0721(6) Uani 1 1 d . . . . .
H23A H 1.102480 0.212444 0.597329 0.086 Uiso 1 1 calc R U . . .
H23B H 1.037994 0.308358 0.669205 0.086 Uiso 1 1 calc R U . . .
C24 C 0.96724(19) 0.3267(2) 0.52397(19) 0.0709(6) Uani 1 1 d . . . . .
H24A H 1.025187 0.377389 0.467803 0.085 Uiso 1 1 calc R U . . .
H24B H 0.944668 0.272842 0.484531 0.085 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
F1 C3 1.3572(19) . ?
N1 C2 1.354(2) . ?
N1 H1B 0.888(16) . ?
N1 H1A 0.897(16) . ?
O1 N3 1.232(2) . ?
C1 C6 1.407(2) . ?
C1 N3 1.415(2) . ?
C1 C2 1.412(2) . ?
C2 C3 1.390(2) . ?
N2 C4 1.348(2) . ?
N2 H2B 0.883(16) . ?
N2 H2A 0.883(16) . ?
F2 C5 1.3599(19) . ?
O2 N3 1.2404(19) . ?
C3 C4 1.378(2) . ?
C4 C5 1.414(2) . ?
C5 C6 1.346(2) . ?
C6 H6 0.9500 . ?
F3 C9 1.3583(19) . ?
O3 N6 1.239(2) . ?
F4 C11 1.360(2) . ?
N4 C8 1.355(2) . ?
N4 H4B 0.879(16) . ?
N4 H4A 0.912(16) . ?
O4 N6 1.245(2) . ?
N5 C10 1.346(2) . ?
N5 H5A 0.874(16) . ?
N5 H5B 0.865(16) . ?
N6 C7 1.415(2) . ?
C7 C12 1.408(2) . ?
C7 C8 1.415(2) . ?
C8 C9 1.394(2) . ?
C9 C10 1.377(2) . ?
C10 C11 1.414(2) . ?
C11 C12 1.346(2) . ?
C12 H12 0.9500 . ?
O5 C13 1.411(3) . ?
O5 C24 1.408(3) . ?
O6 C15 1.406(3) . ?
O6 C14 1.413(3) . ?
O7 C16 1.423(3) . ?
O7 C17 1.414(3) . ?
O8 C19 1.421(2) . ?
O8 C18 1.426(3) . ?
O9 C20 1.419(3) . ?
O9 C21 1.416(3) . ?
O10 C23 1.419(3) . ?
O10 C22 1.422(3) . ?
C13 C14 1.478(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.478(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.482(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.485(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.489(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.485(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

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
C2 N1 H1B 118.1(15) . . ?
C2 N1 H1A 117.1(15) . . ?
H1B N1 H1A 124(2) . . ?
C6 C1 N3 117.64(15) . . ?
C6 C1 C2 120.70(14) . . ?
N3 C1 C2 121.65(14) . . ?
N1 C2 C3 119.14(15) . . ?
N1 C2 C1 125.14(15) . . ?
C3 C2 C1 115.72(14) . . ?
C4 N2 H2B 117.2(15) . . ?
C4 N2 H2A 118.2(15) . . ?
H2B N2 H2A 121(2) . . ?
F1 C3 C4 117.28(14) . . ?
F1 C3 C2 116.65(14) . . ?
C4 C3 C2 126.06(15) . . ?
O1 N3 O2 120.59(15) . . ?
O1 N3 C1 119.05(15) . . ?
O2 N3 C1 120.37(15) . . ?
N2 C4 C3 123.50(16) . . ?
N2 C4 C5 121.95(16) . . ?
C3 C4 C5 114.52(14) . . ?
C6 C5 F2 120.19(15) . . ?
C6 C5 C4 123.55(15) . . ?
F2 C5 C4 116.27(14) . . ?
C5 C6 C1 119.42(15) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C8 N4 H4B 118.2(16) . . ?
C8 N4 H4A 116.2(16) . . ?
H4B N4 H4A 122(2) . . ?
C10 N5 H5A 120.8(16) . . ?
C10 N5 H5B 115.6(16) . . ?
H5A N5 H5B 123(2) . . ?
O3 N6 O4 120.83(15) . . ?
O3 N6 C7 119.38(16) . . ?
O4 N6 C7 119.80(15) . . ?
N6 C7 C12 117.28(15) . . ?
N6 C7 C8 121.92(15) . . ?
C12 C7 C8 120.79(15) . . ?
N4 C8 C9 119.45(16) . . ?
N4 C8 C7 125.19(16) . . ?
C9 C8 C7 115.35(15) . . ?
F3 C9 C10 117.18(15) . . ?
F3 C9 C8 116.58(15) . . ?
C10 C9 C8 126.24(15) . . ?
N5 C10 C9 123.03(16) . . ?
N5 C10 C11 122.31(16) . . ?
C9 C10 C11 114.65(15) . . ?
C12 C11 F4 119.92(16) . . ?
C12 C11 C10 123.43(16) . . ?
F4 C11 C10 116.63(15) . . ?
C11 C12 C7 119.51(15) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C13 O5 C24 112.92(16) . . ?
C15 O6 C14 111.83(16) . . ?
C16 O7 C17 112.02(17) . . ?
C19 O8 C18 112.17(15) . . ?
C20 O9 C21 112.94(16) . . ?
C23 O10 C22 112.73(17) . . ?
O5 C13 C14 109.38(17) . . ?
O5 C13 H13A 109.8 . . ?
C14 C13 H13A 109.8 . . ?
O5 C13 H13B 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
O6 C14 C13 109.45(17) . . ?
O6 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
O6 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
O6 C15 C16 109.34(16) . . ?
O6 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
O6 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
O7 C16 C15 109.87(17) . . ?
O7 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
O7 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
O7 C17 C18 109.23(18) . . ?
O7 C17 H17A 109.8 . . ?
C18 C17 H17A 109.8 . . ?
O7 C17 H17B 109.8 . . ?
C18 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
O8 C18 C17 108.79(17) . . ?
O8 C18 H18A 109.9 . . ?
C17 C18 H18A 109.9 . . ?
O8 C18 H18B 109.9 . . ?
C17 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
O8 C19 C20 109.05(15) . . ?
O8 C19 H19A 109.9 . . ?
C20 C19 H19A 109.9 . . ?
O8 C19 H19B 109.9 . . ?
C20 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
O9 C20 C19 109.02(16) . . ?
O9 C20 H20A 109.9 . . ?
C19 C20 H20A 109.9 . . ?
O9 C20 H20B 109.9 . . ?
C19 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
O9 C21 C22 108.70(17) . . ?
O9 C21 H21A 109.9 . . ?
C22 C21 H21A 109.9 . . ?
O9 C21 H21B 109.9 . . ?
C22 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
O10 C22 C21 109.79(17) . . ?
O10 C22 H22A 109.7 . . ?
C21 C22 H22A 109.7 . . ?
O10 C22 H22B 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
O10 C23 C24 109.94(17) . . ?
O10 C23 H23A 109.7 . . ?
C24 C23 H23A 109.7 . . ?
O10 C23 H23B 109.7 . . ?
C24 C23 H23B 109.7 . . ?
H23A C23 H23B 108.2 . . ?
O5 C24 C23 109.33(17) . . ?
O5 C24 H24A 109.8 . . ?
C23 C24 H24A 109.8 . . ?
O5 C24 H24B 109.8 . . ?
C23 C24 H24B 109.8 . . ?
H24A C24 H24B 108.3 . . ?

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
C6 C1 C2 N1 179.78(16) . . . . ?
N3 C1 C2 N1 -1.4(3) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
N3 C1 C2 C3 178.42(14) . . . . ?
N1 C2 C3 F1 -1.1(2) . . . . ?
C1 C2 C3 F1 179.09(14) . . . . ?
N1 C2 C3 C4 178.40(16) . . . . ?
C1 C2 C3 C4 -1.4(2) . . . . ?
C6 C1 N3 O1 -0.5(2) . . . . ?
C2 C1 N3 O1 -179.35(15) . . . . ?
C6 C1 N3 O2 179.04(14) . . . . ?
C2 C1 N3 O2 0.2(2) . . . . ?
F1 C3 C4 N2 0.0(3) . . . . ?
C2 C3 C4 N2 -179.45(17) . . . . ?
F1 C3 C4 C5 -178.30(14) . . . . ?
C2 C3 C4 C5 2.2(2) . . . . ?
N2 C4 C5 C6 -179.63(17) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
N2 C4 C5 F2 0.2(2) . . . . ?
C3 C4 C5 F2 178.53(14) . . . . ?
F2 C5 C6 C1 179.85(14) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
N3 C1 C6 C5 -177.63(14) . . . . ?
C2 C1 C6 C5 1.2(2) . . . . ?
O3 N6 C7 C12 5.6(2) . . . . ?
O4 N6 C7 C12 -174.41(15) . . . . ?
O3 N6 C7 C8 -173.91(16) . . . . ?
O4 N6 C7 C8 6.1(2) . . . . ?
N6 C7 C8 N4 0.5(3) . . . . ?
C12 C7 C8 N4 -179.04(16) . . . . ?
N6 C7 C8 C9 179.58(14) . . . . ?
C12 C7 C8 C9 0.1(2) . . . . ?
N4 C8 C9 F3 -0.1(2) . . . . ?
C7 C8 C9 F3 -179.25(13) . . . . ?
N4 C8 C9 C10 -179.75(16) . . . . ?
C7 C8 C9 C10 1.1(2) . . . . ?
F3 C9 C10 N5 0.0(2) . . . . ?
C8 C9 C10 N5 179.63(17) . . . . ?
F3 C9 C10 C11 179.06(14) . . . . ?
C8 C9 C10 C11 -1.3(2) . . . . ?
N5 C10 C11 C12 179.41(17) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
N5 C10 C11 F4 0.9(2) . . . . ?
C9 C10 C11 F4 -178.21(14) . . . . ?
F4 C11 C12 C7 179.20(15) . . . . ?
C10 C11 C12 C7 0.7(3) . . . . ?
N6 C7 C12 C11 179.55(15) . . . . ?
C8 C7 C12 C11 -0.9(2) . . . . ?
C24 O5 C13 C14 -175.62(18) . . . . ?
C15 O6 C14 C13 179.80(17) . . . . ?
O5 C13 C14 O6 -65.9(2) . . . . ?
C14 O6 C15 C16 -174.99(17) . . . . ?
C17 O7 C16 C15 171.95(18) . . . . ?
O6 C15 C16 O7 66.4(2) . . . . ?
C16 O7 C17 C18 168.41(18) . . . . ?
C19 O8 C18 C17 -173.62(17) . . . . ?
O7 C17 C18 O8 -65.8(2) . . . . ?
C18 O8 C19 C20 -174.37(17) . . . . ?
C21 O9 C20 C19 -177.06(16) . . . . ?
O8 C19 C20 O9 71.7(2) . . . . ?
C20 O9 C21 C22 178.10(17) . . . . ?
C23 O10 C22 C21 169.98(17) . . . . ?
O9 C21 C22 O10 -68.6(2) . . . . ?
C22 O10 C23 C24 170.56(17) . . . . ?
C13 O5 C24 C23 -170.46(18) . . . . ?
O10 C23 C24 O5 67.5(2) . . . . ?

_refine_diff_density_max         0.601
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.037


####################################################################### 
# 
# 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_Bcr-mal151_1
_database_code_depnum_ccdc_archive 'CCDC 2253809'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2,4-difluoro-6-nitrobenzene-1,3-diamine 18-crown-6 1:1 cocrystal
;
_chemical_name_common            ?
_chemical_melting_point          392.6
_chemical_formula_moiety         'C6 H5 F2 N3 O2, C12 H24 O6'
_chemical_formula_sum            'C18 H29 F2 N3 O8'
_chemical_formula_weight         453.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.9046(8)
_cell_length_b                   9.2505(8)
_cell_length_c                   15.7606(16)
_cell_angle_alpha                79.769(3)
_cell_angle_beta                 84.623(3)
_cell_angle_gamma                78.313(4)
_cell_volume                     1108.61(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      27.04

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.680
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8621
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29238
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0556
_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       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.315
_diffrn_reflns_theta_max         27.242
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4929
_reflns_number_gt                3734
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0904P)²+0.6417P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4929
_refine_ls_number_parameters     296
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1991
_refine_ls_wR_factor_gt          0.1754
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.028
_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
N1 N 0.3627(3) 0.6285(2) 0.88366(13) 0.0562(5) Uani 1 1 d D . . . .
H1B H 0.438(3) 0.544(2) 0.8918(18) 0.071(8) Uiso 1 1 d D . . . .
H1A H 0.375(4) 0.687(3) 0.9191(18) 0.081(9) Uiso 1 1 d D . . . .
F1 F 0.4296(2) 0.45721(14) 0.76121(9) 0.0642(4) Uani 1 1 d . . . . .
O1 O 0.1166(4) 1.0735(2) 0.80517(16) 0.1008(8) Uani 1 1 d . . . . .
C1 C 0.2208(2) 0.8365(2) 0.77721(13) 0.0424(4) Uani 1 1 d . . . . .
C2 C 0.3120(2) 0.6893(2) 0.80347(12) 0.0393(4) Uani 1 1 d . . . . .
N2 N 0.3321(3) 0.5461(3) 0.59633(14) 0.0643(6) Uani 1 1 d D . . . .
H2A H 0.415(4) 0.470(3) 0.608(2) 0.086(10) Uiso 1 1 d D . . . .
H2B H 0.318(4) 0.584(3) 0.5439(13) 0.073(9) Uiso 1 1 d D . . . .
F2 F 0.1408(2) 0.8305(2) 0.55500(9) 0.0749(5) Uani 1 1 d . . . . .
O2 O 0.2086(3) 0.9046(2) 0.91131(14) 0.0844(7) Uani 1 1 d . . . . .
C3 C 0.3439(3) 0.5995(2) 0.73874(13) 0.0412(4) Uani 1 1 d . . . . .
N3 N 0.1814(3) 0.9434(2) 0.83443(15) 0.0591(5) Uani 1 1 d . . . . .
C4 C 0.2961(3) 0.6414(2) 0.65463(13) 0.0440(5) Uani 1 1 d . . . . .
C5 C 0.1992(3) 0.7870(3) 0.63585(13) 0.0486(5) Uani 1 1 d . . . . .
C6 C 0.1639(3) 0.8829(2) 0.69331(14) 0.0489(5) Uani 1 1 d . . . . .
H6 H 0.102034 0.979290 0.677305 0.059 Uiso 1 1 calc R U . . .
O3 O 0.4170(2) 0.69741(17) 1.06798(10) 0.0562(4) Uani 1 1 d . . . . .
O4 O 0.2315(2) 0.4753(2) 1.14221(13) 0.0728(5) Uani 1 1 d . . . . .
O5 O 0.3635(3) 0.2047(2) 1.07243(14) 0.0778(6) Uani 1 1 d . . . . .
C7 C 0.2607(4) 0.7289(3) 1.11800(17) 0.0720(8) Uani 1 1 d . . . . .
H7A H 0.202014 0.830564 1.098678 0.086 Uiso 1 1 calc R U . . .
H7B H 0.284875 0.720034 1.178117 0.086 Uiso 1 1 calc R U . . .
C8 C 0.1499(4) 0.6243(4) 1.10957(19) 0.0778(9) Uani 1 1 d . . . . .
H8A H 0.039824 0.649596 1.141412 0.093 Uiso 1 1 calc R U . . .
H8B H 0.127826 0.631739 1.049291 0.093 Uiso 1 1 calc R U . . .
C9 C 0.1295(5) 0.3695(5) 1.1397(3) 0.1093(14) Uani 1 1 d . . . . .
H9A H 0.063271 0.399646 1.088621 0.131 Uiso 1 1 calc R U . . .
H9B H 0.048059 0.367814 1.189791 0.131 Uiso 1 1 calc R U . . .
C10 C 0.2270(6) 0.2233(5) 1.1387(3) 0.1153(15) Uani 1 1 d . . . . .
H10A H 0.147603 0.158368 1.133491 0.138 Uiso 1 1 calc R U . . .
H10B H 0.277435 0.188325 1.194211 0.138 Uiso 1 1 calc R U . . .
C11 C 0.3155(4) 0.2309(3) 0.9875(2) 0.0828(9) Uani 1 1 d . . . . .
H11A H 0.258941 0.334404 0.971974 0.099 Uiso 1 1 calc R U . . .
H11B H 0.235112 0.167449 0.981375 0.099 Uiso 1 1 calc R U . . .
C12 C 0.4733(5) 0.1977(3) 0.93002(18) 0.0760(9) Uani 1 1 d . . . . .
H12A H 0.535019 0.096892 0.948929 0.091 Uiso 1 1 calc R U . . .
H12B H 0.440965 0.204061 0.871413 0.091 Uiso 1 1 calc R U . . .
O6 O 0.2986(3) 0.6823(2) 0.36908(14) 0.0764(6) Uani 1 1 d . . . . .
O7 O 0.5125(3) 0.8069(2) 0.45061(13) 0.0757(6) Uani 1 1 d . . . . .
O8 O 0.7714(3) 0.6010(2) 0.55476(13) 0.0765(6) Uani 1 1 d . . . . .
C13 C 0.2967(5) 0.8392(3) 0.35559(18) 0.0838(10) Uani 1 1 d . . . . .
H13A H 0.214510 0.885760 0.397021 0.101 Uiso 1 1 calc R U . . .
H13B H 0.260994 0.883720 0.298012 0.101 Uiso 1 1 calc R U . . .
C14 C 0.4709(5) 0.8651(3) 0.3658(2) 0.0861(10) Uani 1 1 d . . . . .
H14A H 0.554395 0.815877 0.325884 0.103 Uiso 1 1 calc R U . . .
H14B H 0.472417 0.971381 0.353871 0.103 Uiso 1 1 calc R U . . .
C15 C 0.6746(4) 0.8338(4) 0.4705(3) 0.0944(12) Uani 1 1 d . . . . .
H15A H 0.667441 0.940251 0.468541 0.113 Uiso 1 1 calc R U . . .
H15B H 0.763745 0.800531 0.427816 0.113 Uiso 1 1 calc R U . . .
C16 C 0.7212(4) 0.7537(4) 0.5570(3) 0.0878(10) Uani 1 1 d . . . . .
H16A H 0.815405 0.791071 0.575557 0.105 Uiso 1 1 calc R U . . .
H16B H 0.622786 0.770808 0.597978 0.105 Uiso 1 1 calc R U . . .
C17 C 0.8368(4) 0.5176(5) 0.6339(2) 0.0862(10) Uani 1 1 d . . . . .
H17A H 0.755972 0.542617 0.681713 0.103 Uiso 1 1 calc R U . . .
H17B H 0.946089 0.543639 0.642636 0.103 Uiso 1 1 calc R U . . .
C18 C 0.8623(4) 0.3555(4) 0.6319(2) 0.0846(10) Uani 1 1 d . . . . .
H18A H 0.933170 0.331592 0.580721 0.102 Uiso 1 1 calc R U . . .
H18B H 0.920775 0.299275 0.682307 0.102 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
N1 C2 1.351(3) . ?
N1 H1B 0.883(17) . ?
N1 H1A 0.870(18) . ?
F1 C3 1.354(2) . ?
O1 N3 1.233(3) . ?
C1 C6 1.402(3) . ?
C1 C2 1.416(3) . ?
C1 N3 1.424(3) . ?
C2 C3 1.401(3) . ?
N2 C4 1.356(3) . ?
N2 H2A 0.865(18) . ?
N2 H2B 0.846(17) . ?
F2 C5 1.361(2) . ?
O2 N3 1.227(3) . ?
C3 C4 1.379(3) . ?
C4 C5 1.404(3) . ?
C5 C6 1.350(3) . ?
C6 H6 0.9300 . ?
O3 C7 1.409(3) . ?
O3 C12 1.432(3) 2_667 ?
O4 C9 1.397(4) . ?
O4 C8 1.425(4) . ?
O5 C11 1.391(4) . ?
O5 C10 1.436(4) . ?
C7 C8 1.460(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.417(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.484(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O6 C18 1.387(4) 2_666 ?
O6 C13 1.427(4) . ?
O7 C14 1.393(4) . ?
O7 C15 1.426(4) . ?
O8 C16 1.394(4) . ?
O8 C17 1.427(4) . ?
C13 C14 1.473(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.471(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.478(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

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
C2 N1 H1B 120.1(19) . . ?
C2 N1 H1A 119(2) . . ?
H1B N1 H1A 111(3) . . ?
C6 C1 C2 121.06(18) . . ?
C6 C1 N3 117.07(19) . . ?
C2 C1 N3 121.87(19) . . ?
N1 C2 C3 118.74(18) . . ?
N1 C2 C1 126.57(18) . . ?
C3 C2 C1 114.63(18) . . ?
C4 N2 H2A 116(2) . . ?
C4 N2 H2B 117(2) . . ?
H2A N2 H2B 118(3) . . ?
F1 C3 C4 116.84(17) . . ?
F1 C3 C2 116.67(17) . . ?
C4 C3 C2 126.48(18) . . ?
O2 N3 O1 121.5(2) . . ?
O2 N3 C1 120.00(19) . . ?
O1 N3 C1 118.5(2) . . ?
N2 C4 C3 122.3(2) . . ?
N2 C4 C5 122.9(2) . . ?
C3 C4 C5 114.67(18) . . ?
C6 C5 F2 119.9(2) . . ?
C6 C5 C4 123.28(19) . . ?
F2 C5 C4 116.8(2) . . ?
C5 C6 C1 119.75(19) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C7 O3 C12 112.0(2) . 2_667 ?
C9 O4 C8 113.2(3) . . ?
C11 O5 C10 117.2(3) . . ?
O3 C7 C8 109.7(2) . . ?
O3 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
O3 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
O4 C8 C7 110.0(2) . . ?
O4 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
O4 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
O4 C9 C10 113.3(3) . . ?
O4 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
O4 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 O5 117.3(3) . . ?
C9 C10 H10A 108.0 . . ?
O5 C10 H10A 108.0 . . ?
C9 C10 H10B 108.0 . . ?
O5 C10 H10B 108.0 . . ?
H10A C10 H10B 107.2 . . ?
O5 C11 C12 108.7(3) . . ?
O5 C11 H11A 110.0 . . ?
C12 C11 H11A 110.0 . . ?
O5 C11 H11B 110.0 . . ?
C12 C11 H11B 110.0 . . ?
H11A C11 H11B 108.3 . . ?
O3 C12 C11 109.8(2) 2_667 . ?
O3 C12 H12A 109.7 2_667 . ?
C11 C12 H12A 109.7 . . ?
O3 C12 H12B 109.7 2_667 . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C18 O6 C13 114.6(2) 2_666 . ?
C14 O7 C15 113.2(3) . . ?
C16 O8 C17 113.0(3) . . ?
O6 C13 C14 109.5(2) . . ?
O6 C13 H13A 109.8 . . ?
C14 C13 H13A 109.8 . . ?
O6 C13 H13B 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
O7 C14 C13 107.7(2) . . ?
O7 C14 H14A 110.2 . . ?
C13 C14 H14A 110.2 . . ?
O7 C14 H14B 110.2 . . ?
C13 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
O7 C15 C16 110.5(2) . . ?
O7 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
O7 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
O8 C16 C15 109.8(3) . . ?
O8 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
O8 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
O8 C17 C18 110.1(2) . . ?
O8 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
O8 C17 H17B 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.2 . . ?
O6 C18 C17 108.5(2) 2_666 . ?
O6 C18 H18A 110.0 2_666 . ?
C17 C18 H18A 110.0 . . ?
O6 C18 H18B 110.0 2_666 . ?
C17 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?

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
C6 C1 C2 N1 -175.1(2) . . . . ?
N3 C1 C2 N1 4.4(3) . . . . ?
C6 C1 C2 C3 2.1(3) . . . . ?
N3 C1 C2 C3 -178.47(18) . . . . ?
N1 C2 C3 F1 -2.0(3) . . . . ?
C1 C2 C3 F1 -179.41(17) . . . . ?
N1 C2 C3 C4 177.6(2) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C6 C1 N3 O2 171.0(2) . . . . ?
C2 C1 N3 O2 -8.5(3) . . . . ?
C6 C1 N3 O1 -7.4(3) . . . . ?
C2 C1 N3 O1 173.1(2) . . . . ?
F1 C3 C4 N2 -0.1(3) . . . . ?
C2 C3 C4 N2 -179.7(2) . . . . ?
F1 C3 C4 C5 176.57(18) . . . . ?
C2 C3 C4 C5 -3.1(3) . . . . ?
N2 C4 C5 C6 -179.5(2) . . . . ?
C3 C4 C5 C6 3.9(3) . . . . ?
N2 C4 C5 F2 0.1(3) . . . . ?
C3 C4 C5 F2 -176.47(18) . . . . ?
F2 C5 C6 C1 178.50(18) . . . . ?
C4 C5 C6 C1 -1.9(3) . . . . ?
C2 C1 C6 C5 -1.3(3) . . . . ?
N3 C1 C6 C5 179.2(2) . . . . ?
C12 O3 C7 C8 176.7(2) 2_667 . . . ?
C9 O4 C8 C7 177.4(2) . . . . ?
O3 C7 C8 O4 62.5(3) . . . . ?
C8 O4 C9 C10 156.5(4) . . . . ?
O4 C9 C10 O5 -54.4(6) . . . . ?
C11 O5 C10 C9 -65.6(5) . . . . ?
C10 O5 C11 C12 -176.9(2) . . . . ?
O5 C11 C12 O3 -66.0(3) . . . 2_667 ?
C18 O6 C13 C14 174.9(2) 2_666 . . . ?
C15 O7 C14 C13 -176.1(2) . . . . ?
O6 C13 C14 O7 -62.7(3) . . . . ?
C14 O7 C15 C16 -172.8(3) . . . . ?
C17 O8 C16 C15 173.5(2) . . . . ?
O7 C15 C16 O8 73.1(3) . . . . ?
C16 O8 C17 C18 171.4(3) . . . . ?
O8 C17 C18 O6 -67.1(3) . . . 2_666 ?

_refine_diff_density_max         0.462
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.047


####################################################################### 
# 
# 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_A-mal148_2
_database_code_depnum_ccdc_archive 'CCDC 2253812'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        2,4,5-trifluoro-6-nitrobenzene-1,3-diamine
_chemical_name_common            ?
_chemical_melting_point          418.2
_chemical_formula_moiety         'C6 H4 F3 N3 O2'
_chemical_formula_sum            'C6 H4 F3 N3 O2'
_chemical_formula_weight         207.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   7.1452(4)
_cell_length_b                   13.5660(8)
_cell_length_c                   7.7555(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     751.75(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5746
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.89

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.830
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.186
_shelx_estimated_absorpt_T_min   0.906
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8989
_exptl_absorpt_correction_T_max  0.9420
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13714
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.003
_diffrn_reflns_theta_max         28.049
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1823
_reflns_number_gt                1521
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0614P)²+0.1087P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 636 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1823
_refine_ls_number_parameters     143
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
F1 F 0.6876(3) 0.48029(11) 0.4322(2) 0.0574(5) Uani 1 1 d . . . . .
O1 O 0.5049(5) 0.2255(2) 0.8593(3) 0.0793(9) Uani 1 1 d . . . . .
N1 N 0.5658(4) 0.3935(3) 0.7147(4) 0.0559(7) Uani 1 1 d . . . . .
H1A H 0.583(6) 0.456(4) 0.702(6) 0.081(14) Uiso 1 1 d . . . . .
H1B H 0.525(6) 0.367(3) 0.796(7) 0.067(12) Uiso 1 1 d . . . . .
C1 C 0.6213(3) 0.23067(16) 0.5855(3) 0.0338(5) Uani 1 1 d . . . . .
C2 C 0.6240(3) 0.33521(17) 0.5841(3) 0.0353(5) Uani 1 1 d . . . . .
F2 F 0.8073(2) 0.17759(13) 0.1586(2) 0.0534(5) Uani 1 1 d . . . . .
O2 O 0.5329(4) 0.08880(19) 0.7238(4) 0.0720(8) Uani 1 1 d . . . . .
N2 N 0.8069(4) 0.3807(2) 0.1449(3) 0.0519(7) Uani 1 1 d . . . . .
H2A H 0.824(5) 0.443(3) 0.154(6) 0.074(12) Uiso 1 1 d . . . . .
H2B H 0.849(6) 0.343(3) 0.055(7) 0.080(13) Uiso 1 1 d . . . . .
C3 C 0.6870(4) 0.38049(17) 0.4336(4) 0.0361(5) Uani 1 1 d . . . . .
F3 F 0.6910(3) 0.08122(11) 0.4317(3) 0.0586(5) Uani 1 1 d . . . . .
N3 N 0.5523(3) 0.17795(19) 0.7310(3) 0.0439(6) Uani 1 1 d . . . . .
C4 C 0.7481(4) 0.33256(19) 0.2880(3) 0.0340(5) Uani 1 1 d . . . . .
C5 C 0.7444(4) 0.22914(17) 0.2952(3) 0.0337(5) Uani 1 1 d . . . . .
C6 C 0.6834(3) 0.17970(17) 0.4374(4) 0.0344(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.354(3) . ?
O1 N3 1.233(4) . ?
N1 C2 1.350(4) . ?
N1 H1A 0.86(5) . ?
N1 H1B 0.78(5) . ?
C1 C2 1.418(3) . ?
C1 C6 1.413(4) . ?
C1 N3 1.424(3) . ?
C2 C3 1.394(4) . ?
F2 C5 1.347(3) . ?
O2 N3 1.219(4) . ?
N2 C4 1.354(4) . ?
N2 H2A 0.86(4) . ?
N2 H2B 0.92(5) . ?
C3 C4 1.374(4) . ?
F3 C6 1.338(3) . ?
C4 C5 1.404(4) . ?
C5 C6 1.362(4) . ?

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
C2 N1 H1A 116(3) . . ?
C2 N1 H1B 117(3) . . ?
H1A N1 H1B 127(5) . . ?
C2 C1 C6 118.6(2) . . ?
C2 C1 N3 120.9(2) . . ?
C6 C1 N3 120.5(2) . . ?
N1 C2 C3 118.0(2) . . ?
N1 C2 C1 125.1(3) . . ?
C3 C2 C1 116.8(2) . . ?
C4 N2 H2A 117(3) . . ?
C4 N2 H2B 117(3) . . ?
H2A N2 H2B 124(4) . . ?
C4 C3 F1 117.8(2) . . ?
C4 C3 C2 125.6(2) . . ?
F1 C3 C2 116.6(2) . . ?
O2 N3 O1 121.6(2) . . ?
O2 N3 C1 120.1(3) . . ?
O1 N3 C1 118.1(2) . . ?
N2 C4 C3 122.9(2) . . ?
N2 C4 C5 121.4(3) . . ?
C3 C4 C5 115.7(2) . . ?
F2 C5 C6 119.2(2) . . ?
F2 C5 C4 118.7(2) . . ?
C6 C5 C4 122.0(2) . . ?
F3 C6 C5 116.9(2) . . ?
F3 C6 C1 121.9(2) . . ?
C5 C6 C1 121.2(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
C6 C1 C2 N1 178.7(3) . . . . ?
N3 C1 C2 N1 0.6(4) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
N3 C1 C2 C3 -177.5(2) . . . . ?
N1 C2 C3 C4 -178.9(2) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
N1 C2 C3 F1 1.2(4) . . . . ?
C1 C2 C3 F1 179.4(2) . . . . ?
C2 C1 N3 O2 172.5(2) . . . . ?
C6 C1 N3 O2 -5.6(4) . . . . ?
C2 C1 N3 O1 -4.0(4) . . . . ?
C6 C1 N3 O1 177.9(3) . . . . ?
F1 C3 C4 N2 -0.4(4) . . . . ?
C2 C3 C4 N2 179.6(2) . . . . ?
F1 C3 C4 C5 -179.8(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
N2 C4 C5 F2 2.4(4) . . . . ?
C3 C4 C5 F2 -178.2(2) . . . . ?
N2 C4 C5 C6 -179.1(3) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
F2 C5 C6 F3 0.3(4) . . . . ?
C4 C5 C6 F3 -178.2(2) . . . . ?
F2 C5 C6 C1 178.2(2) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C2 C1 C6 F3 177.6(2) . . . . ?
N3 C1 C6 F3 -4.2(4) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
N3 C1 C6 C5 178.0(2) . . . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.039


####################################################################### 
# 
# 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_C-a_14_3mal
_database_code_depnum_ccdc_archive 'CCDC 2253814'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        4-fluoro-6-nitrobenzene-1,3-diamine
_chemical_name_common            ?
_chemical_melting_point          494.4
_chemical_formula_moiety         'C6 H6 F N3 O2'
_chemical_formula_sum            'C6 H6 F N3 O2'
_chemical_formula_weight         171.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   4.5277(2)
_cell_length_b                   11.3347(6)
_cell_length_c                   13.8350(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.8990(17)
_cell_angle_gamma                90
_cell_volume                     708.37(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5119
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.19

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8691
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7480
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.325
_diffrn_reflns_theta_max         27.190
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1571
_reflns_number_gt                1337
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0624P)²+0.2272P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1571
_refine_ls_number_parameters     125
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.046
_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
F1 F 0.0156(2) 0.53652(9) 0.63995(7) 0.0538(3) Uani 1 1 d . . . . .
N1 N 0.8266(3) 0.18061(11) 0.71456(9) 0.0378(3) Uani 1 1 d D . . . .
H1B H 0.900(4) 0.1795(17) 0.7756(11) 0.053(5) Uiso 1 1 d D . . . .
H1A H 0.927(4) 0.1467(15) 0.6687(12) 0.046(5) Uiso 1 1 d D . . . .
O1 O 0.5293(3) 0.27204(13) 0.43252(8) 0.0633(4) Uani 1 1 d . . . . .
C1 C 0.5268(3) 0.29901(12) 0.59630(9) 0.0312(3) Uani 1 1 d . . . . .
O2 O 0.7946(3) 0.15391(12) 0.52457(8) 0.0606(4) Uani 1 1 d . . . . .
C2 C 0.6307(3) 0.26882(11) 0.69234(9) 0.0283(3) Uani 1 1 d . . . . .
N2 N 0.1960(3) 0.48371(11) 0.82588(9) 0.0388(3) Uani 1 1 d D . . . .
H2A H 0.223(4) 0.4533(17) 0.8851(12) 0.056(5) Uiso 1 1 d D . . . .
H2B H 0.039(4) 0.5287(17) 0.8121(15) 0.057(6) Uiso 1 1 d D . . . .
C3 C 0.5137(3) 0.33240(12) 0.76794(9) 0.0306(3) Uani 1 1 d . . . . .
H3 H 0.578299 0.313908 0.831377 0.037 Uiso 1 1 calc R U . . .
N3 N 0.6220(3) 0.23923(12) 0.51427(8) 0.0407(3) Uani 1 1 d . . . . .
C4 C 0.3068(3) 0.42126(11) 0.75243(9) 0.0297(3) Uani 1 1 d . . . . .
C5 C 0.2177(3) 0.44865(12) 0.65499(10) 0.0344(3) Uani 1 1 d . . . . .
C6 C 0.3206(3) 0.39067(13) 0.57927(9) 0.0362(3) Uani 1 1 d . . . . .
H6 H 0.255776 0.411064 0.516245 0.043 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
F1 C5 1.3588(15) . ?
N1 C2 1.3577(17) . ?
N1 H1B 0.887(15) . ?
N1 H1A 0.892(14) . ?
O1 N3 1.2366(17) . ?
C1 C6 1.4060(19) . ?
C1 N3 1.4140(17) . ?
C1 C2 1.4210(17) . ?
O2 N3 1.2454(17) . ?
C2 C3 1.4034(18) . ?
N2 C4 1.3618(18) . ?
N2 H2A 0.890(15) . ?
N2 H2B 0.884(15) . ?
C3 C4 1.3822(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.4151(18) . ?
C5 C6 1.346(2) . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1B 115.1(12) . . ?
C2 N1 H1A 120.8(12) . . ?
H1B N1 H1A 119.6(16) . . ?
C6 C1 N3 117.05(11) . . ?
C6 C1 C2 120.58(12) . . ?
N3 C1 C2 122.38(12) . . ?
N1 C2 C3 118.90(12) . . ?
N1 C2 C1 123.97(12) . . ?
C3 C2 C1 117.09(12) . . ?
C4 N2 H2A 116.8(13) . . ?
C4 N2 H2B 118.0(14) . . ?
H2A N2 H2B 118.8(19) . . ?
C4 C3 C2 123.01(11) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
O1 N3 O2 120.63(13) . . ?
O1 N3 C1 119.14(13) . . ?
O2 N3 C1 120.23(12) . . ?
N2 C4 C3 122.89(12) . . ?
N2 C4 C5 120.08(12) . . ?
C3 C4 C5 117.01(12) . . ?
C6 C5 F1 120.24(12) . . ?
C6 C5 C4 122.88(12) . . ?
F1 C5 C4 116.88(12) . . ?
C5 C6 C1 119.42(12) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?

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
C6 C1 C2 N1 179.13(12) . . . . ?
N3 C1 C2 N1 -0.5(2) . . . . ?
C6 C1 C2 C3 1.38(18) . . . . ?
N3 C1 C2 C3 -178.25(11) . . . . ?
N1 C2 C3 C4 -178.05(12) . . . . ?
C1 C2 C3 C4 -0.18(19) . . . . ?
C6 C1 N3 O1 2.4(2) . . . . ?
C2 C1 N3 O1 -177.97(13) . . . . ?
C6 C1 N3 O2 -176.90(13) . . . . ?
C2 C1 N3 O2 2.7(2) . . . . ?
C2 C3 C4 N2 -179.25(12) . . . . ?
C2 C3 C4 C5 -1.19(19) . . . . ?
N2 C4 C5 C6 179.58(13) . . . . ?
C3 C4 C5 C6 1.5(2) . . . . ?
N2 C4 C5 F1 -1.49(19) . . . . ?
C3 C4 C5 F1 -179.61(11) . . . . ?
F1 C5 C6 C1 -179.21(12) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
N3 C1 C6 C5 178.50(12) . . . . ?
C2 C1 C6 C5 -1.1(2) . . . . ?

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.046



####################################################################### 
# 
# 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_Acr-a_5_1mal
_database_code_depnum_ccdc_archive 'CCDC 2253808'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2,4,5-trifluoro-6-nitrobenzene-1,3-diamine 18-crown-6 1:1 cocrystal
;
_chemical_name_common            ?
_chemical_melting_point          415.3
_chemical_formula_moiety         'C6 H4 F3 N3 O2, C12 H24 O6'
_chemical_formula_sum            'C18 H28 F3 N3 O8'
_chemical_formula_weight         471.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.0036(7)
_cell_length_b                   9.2934(7)
_cell_length_c                   15.7077(12)
_cell_angle_alpha                80.801(4)
_cell_angle_beta                 81.339(4)
_cell_angle_gamma                78.770(4)
_cell_volume                     1122.60(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9959
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.39

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8869
_exptl_absorpt_correction_T_max  0.9562
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30056
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.323
_diffrn_reflns_theta_max         27.645
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5213
_reflns_number_gt                3990
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1858P)²+1.9077P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5213
_refine_ls_number_parameters     302
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0944
_refine_ls_wR_factor_ref         0.3318
_refine_ls_wR_factor_gt          0.3077
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.012
_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
F1 F 0.5614(4) 0.5484(3) 0.23719(17) 0.0608(8) Uani 1 1 d . . . . .
O1 O 0.8163(10) -0.0633(5) 0.1775(4) 0.117(2) Uani 1 1 d . . . . .
C1 C 0.7685(5) 0.1735(4) 0.2107(3) 0.0415(8) Uani 1 1 d . . . . .
N3 N 0.7985(6) 0.0686(4) 0.1495(3) 0.0615(10) Uani 1 1 d . . . . .
F2 F 0.8548(4) 0.1837(4) 0.42999(18) 0.0706(9) Uani 1 1 d . . . . .
N1 N 0.6302(6) 0.3792(5) 0.1106(3) 0.0567(10) Uani 1 1 d D . . . .
H1B H 0.557(6) 0.466(4) 0.109(4) 0.068 Uiso 1 1 d D U . . .
H1A H 0.627(8) 0.317(5) 0.073(3) 0.068 Uiso 1 1 d D U . . .
C2 C 0.6800(5) 0.3201(4) 0.1895(2) 0.0396(8) Uani 1 1 d . . . . .
O2 O 0.8080(8) 0.1141(5) 0.0720(3) 0.0928(16) Uani 1 1 d . . . . .
F3 F 0.9243(4) -0.0001(3) 0.3117(2) 0.0757(10) Uani 1 1 d . . . . .
N2 N 0.6596(6) 0.4615(5) 0.3991(3) 0.0598(10) Uani 1 1 d D . . . .
H2A H 0.686(8) 0.428(7) 0.4532(17) 0.072 Uiso 1 1 d D U . . .
H2B H 0.569(5) 0.535(5) 0.393(4) 0.072 Uiso 1 1 d D U . . .
C3 C 0.6458(5) 0.4084(4) 0.2559(2) 0.0394(8) Uani 1 1 d . . . . .
C4 C 0.6943(5) 0.3689(5) 0.3386(2) 0.0409(8) Uani 1 1 d . . . . .
C5 C 0.7915(5) 0.2255(5) 0.3538(3) 0.0448(9) Uani 1 1 d . . . . .
C6 C 0.8254(5) 0.1321(4) 0.2929(3) 0.0462(9) Uani 1 1 d . . . . .
O3 O 0.6946(4) 0.3182(4) 0.6227(3) 0.0616(9) Uani 1 1 d . . . . .
O4 O 0.7718(5) 0.5991(4) 0.5504(2) 0.0614(9) Uani 1 1 d . . . . .
O5 O 0.5180(4) 0.8060(4) 0.4571(2) 0.0591(8) Uani 1 1 d . . . . .
C7 C 0.8568(6) 0.3555(7) 0.6216(3) 0.0616(12) Uani 1 1 d . . . . .
H7A H 0.928894 0.332761 0.568325 0.074 Uiso 1 1 calc R U . . .
H7B H 0.911989 0.298745 0.670319 0.074 Uiso 1 1 calc R U . . .
C8 C 0.8341(7) 0.5164(7) 0.6273(3) 0.0641(13) Uani 1 1 d . . . . .
H8A H 0.753196 0.540374 0.677668 0.077 Uiso 1 1 calc R U . . .
H8B H 0.942923 0.541916 0.633842 0.077 Uiso 1 1 calc R U . . .
C9 C 0.7261(7) 0.7508(7) 0.5566(4) 0.0679(14) Uani 1 1 d . . . . .
H9A H 0.821339 0.786600 0.572752 0.081 Uiso 1 1 calc R U . . .
H9B H 0.629102 0.767664 0.601165 0.081 Uiso 1 1 calc R U . . .
C10 C 0.6799(7) 0.8323(6) 0.4712(4) 0.0682(14) Uani 1 1 d . . . . .
H10A H 0.675132 0.937520 0.470644 0.082 Uiso 1 1 calc R U . . .
H10B H 0.766835 0.799444 0.424953 0.082 Uiso 1 1 calc R U . . .
C11 C 0.4777(7) 0.8626(5) 0.3728(3) 0.0629(13) Uani 1 1 d . . . . .
H11A H 0.561304 0.813968 0.330300 0.076 Uiso 1 1 calc R U . . .
H11B H 0.480433 0.967909 0.361518 0.076 Uiso 1 1 calc R U . . .
C12 C 0.3038(7) 0.8361(5) 0.3656(3) 0.0620(13) Uani 1 1 d . . . . .
H12A H 0.220963 0.881708 0.409524 0.074 Uiso 1 1 calc R U . . .
H12B H 0.270743 0.879790 0.308926 0.074 Uiso 1 1 calc R U . . .
O6 O 0.4072(4) 0.7008(3) 0.07033(19) 0.0516(7) Uani 1 1 d . . . . .
O7 O 0.6309(6) 0.7961(5) -0.0746(3) 0.0735(11) Uani 1 1 d . . . . .
O8 O 0.7759(5) 0.5228(4) -0.1441(3) 0.0668(9) Uani 1 1 d . . . . .
C13 C 0.5153(9) 0.8051(5) 0.0715(3) 0.0668(14) Uani 1 1 d . . . . .
H13A H 0.544397 0.799558 0.129863 0.080 Uiso 1 1 calc R U . . .
H13B H 0.455225 0.904509 0.054689 0.080 Uiso 1 1 calc R U . . .
C14 C 0.6745(9) 0.7732(7) 0.0104(5) 0.0766(16) Uani 1 1 d . . . . .
H14A H 0.753196 0.837875 0.015299 0.092 Uiso 1 1 calc R U . . .
H14B H 0.730561 0.671513 0.024576 0.092 Uiso 1 1 calc R U . . .
C15 C 0.7693(11) 0.7794(9) -0.1428(5) 0.098(2) Uani 1 1 d . . . . .
H15A H 0.843115 0.849652 -0.140433 0.118 Uiso 1 1 calc R U . . .
H15B H 0.722761 0.805326 -0.197842 0.118 Uiso 1 1 calc R U . . .
C16 C 0.8747(9) 0.6315(9) -0.1412(6) 0.093(2) Uani 1 1 d . . . . .
H16A H 0.963658 0.631148 -0.190545 0.112 Uiso 1 1 calc R U . . .
H16B H 0.930262 0.607586 -0.088679 0.112 Uiso 1 1 calc R U . . .
C17 C 0.8579(7) 0.3773(8) -0.1181(4) 0.0722(15) Uani 1 1 d . . . . .
H17A H 0.880842 0.367770 -0.058351 0.087 Uiso 1 1 calc R U . . .
H17B H 0.966663 0.355935 -0.154343 0.087 Uiso 1 1 calc R U . . .
C18 C 0.7477(7) 0.2713(6) -0.1258(3) 0.0635(13) Uani 1 1 d . . . . .
H18A H 0.723840 0.281289 -0.185416 0.076 Uiso 1 1 calc R U . . .
H18B H 0.806227 0.170917 -0.110072 0.076 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
F1 C3 1.353(4) . ?
O1 N3 1.223(6) . ?
C1 C6 1.404(6) . ?
C1 C2 1.421(5) . ?
C1 N3 1.439(6) . ?
N3 O2 1.220(7) . ?
F2 C5 1.341(5) . ?
N1 C2 1.357(5) . ?
N1 H1B 0.899(10) . ?
N1 H1A 0.898(10) . ?
C2 C3 1.392(5) . ?
F3 C6 1.341(5) . ?
N2 C4 1.346(6) . ?
N2 H2A 0.897(10) . ?
N2 H2B 0.896(10) . ?
C3 C4 1.383(5) . ?
C4 C5 1.411(6) . ?
C5 C6 1.355(7) . ?
O3 C7 1.404(6) . ?
O3 C12 1.414(6) 2_666 ?
O4 C9 1.401(7) . ?
O4 C8 1.426(6) . ?
O5 C11 1.405(6) . ?
O5 C10 1.420(6) . ?
C7 C8 1.486(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.492(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.484(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O6 C18 1.409(6) 2_665 ?
O6 C13 1.424(6) . ?
O7 C14 1.405(8) . ?
O7 C15 1.423(8) . ?
O8 C17 1.408(8) . ?
O8 C16 1.409(7) . ?
C13 C14 1.486(9) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.465(12) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.474(9) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

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
C6 C1 C2 118.8(4) . . ?
C6 C1 N3 120.4(4) . . ?
C2 C1 N3 120.8(4) . . ?
O2 N3 O1 122.5(5) . . ?
O2 N3 C1 119.1(4) . . ?
O1 N3 C1 118.4(5) . . ?
C2 N1 H1B 115(4) . . ?
C2 N1 H1A 118(4) . . ?
H1B N1 H1A 120(6) . . ?
N1 C2 C3 118.7(3) . . ?
N1 C2 C1 125.3(4) . . ?
C3 C2 C1 115.9(3) . . ?
C4 N2 H2A 120(4) . . ?
C4 N2 H2B 116(4) . . ?
H2A N2 H2B 117(6) . . ?
F1 C3 C4 116.6(3) . . ?
F1 C3 C2 116.9(3) . . ?
C4 C3 C2 126.5(4) . . ?
N2 C4 C3 123.2(4) . . ?
N2 C4 C5 121.8(4) . . ?
C3 C4 C5 114.9(4) . . ?
F2 C5 C6 120.0(4) . . ?
F2 C5 C4 118.3(4) . . ?
C6 C5 C4 121.7(4) . . ?
F3 C6 C5 117.7(4) . . ?
F3 C6 C1 120.3(4) . . ?
C5 C6 C1 122.0(4) . . ?
C7 O3 C12 113.6(4) . 2_666 ?
C9 O4 C8 112.2(4) . . ?
C11 O5 C10 112.6(4) . . ?
O3 C7 C8 108.6(4) . . ?
O3 C7 H7A 110.0 . . ?
C8 C7 H7A 110.0 . . ?
O3 C7 H7B 110.0 . . ?
C8 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
O4 C8 C7 109.5(4) . . ?
O4 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
O4 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
O4 C9 C10 109.4(5) . . ?
O4 C9 H9A 109.8 . . ?
C10 C9 H9A 109.8 . . ?
O4 C9 H9B 109.8 . . ?
C10 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
O5 C10 C9 109.8(4) . . ?
O5 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
O5 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O5 C11 C12 108.6(4) . . ?
O5 C11 H11A 110.0 . . ?
C12 C11 H11A 110.0 . . ?
O5 C11 H11B 110.0 . . ?
C12 C11 H11B 110.0 . . ?
H11A C11 H11B 108.3 . . ?
O3 C12 C11 109.0(4) 2_666 . ?
O3 C12 H12A 109.9 2_666 . ?
C11 C12 H12A 109.9 . . ?
O3 C12 H12B 109.9 2_666 . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C18 O6 C13 111.9(4) 2_665 . ?
C14 O7 C15 116.7(6) . . ?
C17 O8 C16 113.7(5) . . ?
O6 C13 C14 109.8(4) . . ?
O6 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
O6 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
O7 C14 C13 108.8(5) . . ?
O7 C14 H14A 109.9 . . ?
C13 C14 H14A 109.9 . . ?
O7 C14 H14B 109.9 . . ?
C13 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
O7 C15 C16 115.7(6) . . ?
O7 C15 H15A 108.4 . . ?
C16 C15 H15A 108.4 . . ?
O7 C15 H15B 108.4 . . ?
C16 C15 H15B 108.4 . . ?
H15A C15 H15B 107.4 . . ?
O8 C16 C15 111.7(6) . . ?
O8 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
O8 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
O8 C17 C18 109.9(5) . . ?
O8 C17 H17A 109.7 . . ?
C18 C17 H17A 109.7 . . ?
O8 C17 H17B 109.7 . . ?
C18 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
O6 C18 C17 109.4(4) 2_665 . ?
O6 C18 H18A 109.8 2_665 . ?
C17 C18 H18A 109.8 . . ?
O6 C18 H18B 109.8 2_665 . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?

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
C6 C1 N3 O2 -153.3(5) . . . . ?
C2 C1 N3 O2 27.0(7) . . . . ?
C6 C1 N3 O1 25.5(7) . . . . ?
C2 C1 N3 O1 -154.1(6) . . . . ?
C6 C1 C2 N1 174.3(4) . . . . ?
N3 C1 C2 N1 -6.1(6) . . . . ?
C6 C1 C2 C3 -4.6(5) . . . . ?
N3 C1 C2 C3 175.0(4) . . . . ?
N1 C2 C3 F1 1.1(6) . . . . ?
C1 C2 C3 F1 -179.9(3) . . . . ?
N1 C2 C3 C4 -176.7(4) . . . . ?
C1 C2 C3 C4 2.3(6) . . . . ?
F1 C3 C4 N2 0.8(6) . . . . ?
C2 C3 C4 N2 178.6(4) . . . . ?
F1 C3 C4 C5 -176.1(3) . . . . ?
C2 C3 C4 C5 1.7(6) . . . . ?
N2 C4 C5 F2 -2.2(6) . . . . ?
C3 C4 C5 F2 174.8(3) . . . . ?
N2 C4 C5 C6 179.6(4) . . . . ?
C3 C4 C5 C6 -3.4(6) . . . . ?
F2 C5 C6 F3 -0.7(6) . . . . ?
C4 C5 C6 F3 177.5(4) . . . . ?
F2 C5 C6 C1 -177.1(4) . . . . ?
C4 C5 C6 C1 1.1(6) . . . . ?
C2 C1 C6 F3 -173.2(4) . . . . ?
N3 C1 C6 F3 7.2(6) . . . . ?
C2 C1 C6 C5 3.1(6) . . . . ?
N3 C1 C6 C5 -176.5(4) . . . . ?
C12 O3 C7 C8 -168.6(4) 2_666 . . . ?
C9 O4 C8 C7 172.0(4) . . . . ?
O3 C7 C8 O4 -66.4(5) . . . . ?
C8 O4 C9 C10 174.1(4) . . . . ?
C11 O5 C10 C9 -171.7(4) . . . . ?
O4 C9 C10 O5 73.0(5) . . . . ?
C10 O5 C11 C12 -177.4(4) . . . . ?
O5 C11 C12 O3 -63.0(5) . . . 2_666 ?
C18 O6 C13 C14 -178.6(5) 2_665 . . . ?
C15 O7 C14 C13 176.3(5) . . . . ?
O6 C13 C14 O7 65.1(5) . . . . ?
C14 O7 C15 C16 62.4(8) . . . . ?
C17 O8 C16 C15 -162.8(6) . . . . ?
O7 C15 C16 O8 57.9(10) . . . . ?
C16 O8 C17 C18 -178.2(5) . . . . ?
O8 C17 C18 O6 -61.7(6) . . . 2_665 ?

_refine_diff_density_max         0.428
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.081


####################################################################### 
# 
# 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_B-mal131_3
_database_code_depnum_ccdc_archive 'CCDC 2253813'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        2,4-difluoro-6-nitrobenzene-1,3-diamine
_chemical_name_common            ?
_chemical_melting_point          455.8
_chemical_formula_moiety         'C6 H5 F2 N3 O2'
_chemical_formula_sum            'C6 H5 F2 N3 O2'
_chemical_formula_weight         189.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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, -y, z+1/2'

_cell_length_a                   7.6215(4)
_cell_length_b                   3.6750(2)
_cell_length_c                   13.2829(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.936(2)
_cell_angle_gamma                90
_cell_volume                     359.47(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3485
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      27.14

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_F_000             192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.166
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8298
_exptl_absorpt_correction_T_max  0.8878
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4750
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.766
_diffrn_reflns_theta_max         27.137
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1592
_reflns_number_gt                1487
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.988
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.997

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0574P)²+0.0158P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 716 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1592
_refine_ls_number_parameters     134
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0792
_refine_ls_wR_factor_gt          0.0765
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
N1 N 0.7383(3) 0.0016(6) 0.42369(17) 0.0423(4) Uani 1 1 d . . . . .
H1B H 0.720(4) -0.087(9) 0.357(3) 0.051(8) Uiso 1 1 d . . . . .
H1A H 0.839(5) -0.033(9) 0.474(3) 0.056(9) Uiso 1 1 d . . . . .
F1 F 0.4222(2) 0.0272(4) 0.27885(10) 0.0486(4) Uani 1 1 d . . . . .
O1 O 0.7393(2) 0.3893(6) 0.72017(12) 0.0530(5) Uani 1 1 d . . . . .
C1 C 0.5894(2) 0.2691(6) 0.55060(14) 0.0303(4) Uani 1 1 d . . . . .
C2 C 0.5921(3) 0.1370(5) 0.45065(15) 0.0286(4) Uani 1 1 d . . . . .
N2 N 0.1103(3) 0.2958(8) 0.3148(2) 0.0599(6) Uani 1 1 d . . . . .
H2B H 0.017(6) 0.397(12) 0.329(3) 0.069(11) Uiso 1 1 d . . . . .
H2A H 0.101(6) 0.205(10) 0.251(3) 0.070(11) Uiso 1 1 d . . . . .
F2 F 0.12177(19) 0.5661(5) 0.50760(15) 0.0589(5) Uani 1 1 d . . . . .
O2 O 0.8876(2) 0.1169(6) 0.62308(15) 0.0568(5) Uani 1 1 d . . . . .
C3 C 0.4266(3) 0.1550(6) 0.37553(14) 0.0338(5) Uani 1 1 d . . . . .
N3 N 0.7464(2) 0.2573(5) 0.63479(13) 0.0372(4) Uani 1 1 d . . . . .
C4 C 0.2671(3) 0.2916(6) 0.39067(16) 0.0357(5) Uani 1 1 d . . . . .
C5 C 0.2768(3) 0.4253(5) 0.49156(17) 0.0369(5) Uani 1 1 d . . . . .
C6 C 0.4304(3) 0.4143(6) 0.56983(16) 0.0339(4) Uani 1 1 d . . . . .
H6 H 0.430993 0.501720 0.635617 0.041 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
N1 C2 1.350(3) . ?
N1 H1B 0.92(3) . ?
N1 H1A 0.89(4) . ?
F1 C3 1.360(2) . ?
O1 N3 1.247(3) . ?
C1 C6 1.406(3) . ?
C1 N3 1.412(2) . ?
C1 C2 1.419(3) . ?
C2 C3 1.394(3) . ?
N2 C4 1.351(3) . ?
N2 H2B 0.86(5) . ?
N2 H2A 0.90(4) . ?
F2 C5 1.356(2) . ?
O2 N3 1.239(3) . ?
C3 C4 1.377(3) . ?
C4 C5 1.411(3) . ?
C5 C6 1.351(3) . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1B 117(2) . . ?
C2 N1 H1A 117(2) . . ?
H1B N1 H1A 125(3) . . ?
C6 C1 N3 117.49(17) . . ?
C6 C1 C2 121.39(17) . . ?
N3 C1 C2 121.12(18) . . ?
N1 C2 C3 118.96(18) . . ?
N1 C2 C1 125.90(19) . . ?
C3 C2 C1 115.13(17) . . ?
C4 N2 H2B 118(3) . . ?
C4 N2 H2A 123(3) . . ?
H2B N2 H2A 120(4) . . ?
F1 C3 C4 117.12(17) . . ?
F1 C3 C2 117.21(18) . . ?
C4 C3 C2 125.67(18) . . ?
O1 N3 O2 121.24(17) . . ?
O1 N3 C1 118.80(18) . . ?
O2 N3 C1 119.95(18) . . ?
N2 C4 C3 122.7(2) . . ?
N2 C4 C5 121.6(2) . . ?
C3 C4 C5 115.68(17) . . ?
C6 C5 F2 120.5(2) . . ?
C6 C5 C4 122.91(19) . . ?
F2 C5 C4 116.58(18) . . ?
C5 C6 C1 119.19(19) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?

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
C6 C1 C2 N1 178.2(2) . . . . ?
N3 C1 C2 N1 -2.2(3) . . . . ?
C6 C1 C2 C3 -1.4(2) . . . . ?
N3 C1 C2 C3 178.17(17) . . . . ?
N1 C2 C3 F1 1.1(3) . . . . ?
C1 C2 C3 F1 -179.21(16) . . . . ?
N1 C2 C3 C4 -178.8(2) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C6 C1 N3 O1 -3.1(3) . . . . ?
C2 C1 N3 O1 177.30(18) . . . . ?
C6 C1 N3 O2 176.7(2) . . . . ?
C2 C1 N3 O2 -2.9(3) . . . . ?
F1 C3 C4 N2 1.2(3) . . . . ?
C2 C3 C4 N2 -178.9(2) . . . . ?
F1 C3 C4 C5 -179.39(17) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
N2 C4 C5 C6 177.9(2) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
N2 C4 C5 F2 -1.6(3) . . . . ?
C3 C4 C5 F2 179.04(18) . . . . ?
F2 C5 C6 C1 -179.55(16) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
N3 C1 C6 C5 -179.07(17) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.030


####################################################################### 
# 
# 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_Dcr_mal169_1
_database_code_depnum_ccdc_archive 'CCDC 2253811'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2,4-diaminenitrobenzene 18-crown-6 1:1 cocrystal
;
_chemical_name_common            ?
_chemical_melting_point          400.6
_chemical_formula_moiety         'C6 H7 N3 O2, C12 H24 O6'
_chemical_formula_sum            'C18 H31 N3 O8'
_chemical_formula_weight         417.46

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   13.7751(10)
_cell_length_b                   11.1808(6)
_cell_length_c                   14.7876(11)
_cell_angle_alpha                90
_cell_angle_beta                 109.477(3)
_cell_angle_gamma                90
_cell_volume                     2147.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3313
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.45

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.640
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8435
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5827
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.404
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.685
_diffrn_reflns_point_group_measured_fraction_full 0.732
_reflns_number_total             3403
_reflns_number_gt                3035
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.413
_reflns_Friedel_fraction_max     0.400
_reflns_Friedel_fraction_full    0.479

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0637P)²+0.3242P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 889 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3403
_refine_ls_number_parameters     278
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1150
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.985
_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
O3 O 0.47632(17) 0.74162(17) 0.49245(17) 0.0507(5) Uani 1 1 d . . . . .
O4 O 0.32277(14) 0.67588(17) 0.57468(15) 0.0478(5) Uani 1 1 d . . . . .
O5 O 0.32638(16) 0.43687(18) 0.66020(16) 0.0508(5) Uani 1 1 d . . . . .
O6 O 0.52267(16) 0.33557(16) 0.75731(17) 0.0481(5) Uani 1 1 d . . . . .
O7 O 0.67639(14) 0.40949(19) 0.68138(15) 0.0500(5) Uani 1 1 d . . . . .
C7 C 0.3945(3) 0.8163(3) 0.4951(3) 0.0590(8) Uani 1 1 d . . . . .
H7A H 0.377502 0.872191 0.441888 0.071 Uiso 1 1 calc R U . . .
H7B H 0.415282 0.861920 0.554282 0.071 Uiso 1 1 calc R U . . .
O8 O 0.67440(17) 0.64297(18) 0.59471(15) 0.0509(5) Uani 1 1 d . . . . .
C8 C 0.3023(3) 0.7419(3) 0.4888(2) 0.0547(8) Uani 1 1 d . . . . .
H8A H 0.242854 0.792980 0.479537 0.066 Uiso 1 1 calc R U . . .
H8B H 0.287351 0.687760 0.434596 0.066 Uiso 1 1 calc R U . . .
C9 C 0.2367(2) 0.6068(3) 0.5762(3) 0.0538(8) Uani 1 1 d . . . . .
H9A H 0.215754 0.553699 0.521171 0.065 Uiso 1 1 calc R U . . .
H9B H 0.179388 0.659376 0.572164 0.065 Uiso 1 1 calc R U . . .
C10 C 0.2635(2) 0.5354(3) 0.6658(2) 0.0532(7) Uani 1 1 d . . . . .
H10A H 0.299915 0.585278 0.720205 0.064 Uiso 1 1 calc R U . . .
H10B H 0.201047 0.506536 0.675086 0.064 Uiso 1 1 calc R U . . .
C11 C 0.3462(2) 0.3585(3) 0.7407(2) 0.0493(7) Uani 1 1 d . . . . .
H11A H 0.284011 0.315008 0.736824 0.059 Uiso 1 1 calc R U . . .
H11B H 0.367210 0.404675 0.799596 0.059 Uiso 1 1 calc R U . . .
C12 C 0.4284(2) 0.2736(3) 0.7413(2) 0.0482(7) Uani 1 1 d . . . . .
H12A H 0.436684 0.214649 0.791476 0.058 Uiso 1 1 calc R U . . .
H12B H 0.409522 0.231900 0.680340 0.058 Uiso 1 1 calc R U . . .
C13 C 0.6027(2) 0.2601(2) 0.7515(2) 0.0501(7) Uani 1 1 d . . . . .
H13A H 0.581599 0.219474 0.690002 0.060 Uiso 1 1 calc R U . . .
H13B H 0.617964 0.200105 0.801658 0.060 Uiso 1 1 calc R U . . .
C14 C 0.6965(2) 0.3341(3) 0.7626(2) 0.0495(7) Uani 1 1 d . . . . .
H14A H 0.713058 0.381897 0.820451 0.059 Uiso 1 1 calc R U . . .
H14B H 0.754731 0.282532 0.767579 0.059 Uiso 1 1 calc R U . . .
C15 C 0.7642(2) 0.4752(3) 0.6819(3) 0.0530(7) Uani 1 1 d . . . . .
H15A H 0.820685 0.420964 0.686723 0.064 Uiso 1 1 calc R U . . .
H15B H 0.785266 0.528359 0.736907 0.064 Uiso 1 1 calc R U . . .
C16 C 0.7390(2) 0.5461(3) 0.5916(2) 0.0509(7) Uani 1 1 d . . . . .
H16A H 0.801922 0.576025 0.584027 0.061 Uiso 1 1 calc R U . . .
H16B H 0.704638 0.495441 0.537128 0.061 Uiso 1 1 calc R U . . .
C17 C 0.6534(2) 0.7176(3) 0.5126(2) 0.0505(7) Uani 1 1 d . . . . .
H17A H 0.631792 0.669190 0.454845 0.061 Uiso 1 1 calc R U . . .
H17B H 0.715276 0.760674 0.514561 0.061 Uiso 1 1 calc R U . . .
C18 C 0.5704(3) 0.8043(3) 0.5109(2) 0.0519(7) Uani 1 1 d . . . . .
H18A H 0.587868 0.845106 0.572189 0.062 Uiso 1 1 calc R U . . .
H18B H 0.563377 0.863803 0.461425 0.062 Uiso 1 1 calc R U . . .
N1 N 0.5738(2) 0.3723(2) 0.2661(2) 0.0545(7) Uani 1 1 d D . . . .
H1B H 0.576(3) 0.450(2) 0.261(3) 0.065(11) Uiso 1 1 d D . . . .
H1A H 0.584(3) 0.322(3) 0.226(3) 0.067(11) Uiso 1 1 d D . . . .
O1 O 0.5234(2) 0.0130(2) 0.3160(2) 0.0758(8) Uani 1 1 d . . . . .
C1 C 0.51560(18) 0.2117(2) 0.34918(18) 0.0336(5) Uani 1 1 d . . . . .
N2 N 0.4411(2) 0.4727(2) 0.5147(2) 0.0540(6) Uani 1 1 d D . . . .
H2A H 0.458(3) 0.549(2) 0.509(3) 0.075(12) Uiso 1 1 d D . . . .
H2B H 0.417(3) 0.442(3) 0.558(2) 0.062(11) Uiso 1 1 d D . . . .
O2 O 0.5813(2) 0.1395(2) 0.2362(2) 0.0742(8) Uani 1 1 d . . . . .
C2 C 0.53359(18) 0.3341(2) 0.33259(19) 0.0346(5) Uani 1 1 d . . . . .
N3 N 0.54079(19) 0.1175(2) 0.29760(18) 0.0472(6) Uani 1 1 d . . . . .
C3 C 0.50936(19) 0.4184(2) 0.39152(19) 0.0368(5) Uani 1 1 d . . . . .
H3 H 0.522916 0.498524 0.383924 0.044 Uiso 1 1 calc R U . . .
C4 C 0.46619(18) 0.3885(2) 0.46070(19) 0.0375(5) Uani 1 1 d . . . . .
C5 C 0.4471(2) 0.2662(3) 0.4735(2) 0.0425(6) Uani 1 1 d . . . . .
H5 H 0.417459 0.243898 0.519048 0.051 Uiso 1 1 calc R U . . .
C6 C 0.47193(19) 0.1821(2) 0.41936(19) 0.0382(6) Uani 1 1 d . . . . .
H6 H 0.459693 0.102079 0.428957 0.046 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
O3 C7 1.414(4) . ?
O3 C18 1.417(4) . ?
O4 C8 1.414(4) . ?
O4 C9 1.422(4) . ?
O5 C10 1.421(4) . ?
O5 C11 1.429(4) . ?
O6 C13 1.414(3) . ?
O6 C12 1.421(3) . ?
O7 C15 1.413(4) . ?
O7 C14 1.417(4) . ?
C7 C8 1.495(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
O8 C16 1.412(4) . ?
O8 C17 1.422(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.484(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.476(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.496(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.491(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.494(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
N1 C2 1.348(4) . ?
N1 H1B 0.88(2) . ?
N1 H1A 0.86(2) . ?
O1 N3 1.241(3) . ?
C1 C6 1.402(4) . ?
C1 N3 1.410(3) . ?
C1 C2 1.427(3) . ?
N2 C4 1.353(4) . ?
N2 H2A 0.89(2) . ?
N2 H2B 0.88(2) . ?
O2 N3 1.239(3) . ?
C2 C3 1.397(4) . ?
C3 C4 1.385(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.417(4) . ?
C5 C6 1.351(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O3 C18 112.8(2) . . ?
C8 O4 C9 112.3(2) . . ?
C10 O5 C11 112.2(2) . . ?
C13 O6 C12 112.8(2) . . ?
C15 O7 C14 112.3(2) . . ?
O3 C7 C8 109.7(2) . . ?
O3 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
O3 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C16 O8 C17 111.9(2) . . ?
O4 C8 C7 108.9(3) . . ?
O4 C8 H8A 109.9 . . ?
C7 C8 H8A 109.9 . . ?
O4 C8 H8B 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
O4 C9 C10 110.2(2) . . ?
O4 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
O4 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
O5 C10 C9 109.8(2) . . ?
O5 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
O5 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O5 C11 C12 109.4(2) . . ?
O5 C11 H11A 109.8 . . ?
C12 C11 H11A 109.8 . . ?
O5 C11 H11B 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
O6 C12 C11 110.1(2) . . ?
O6 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
O6 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.2 . . ?
O6 C13 C14 109.0(2) . . ?
O6 C13 H13A 109.9 . . ?
C14 C13 H13A 109.9 . . ?
O6 C13 H13B 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
O7 C14 C13 108.6(2) . . ?
O7 C14 H14A 110.0 . . ?
C13 C14 H14A 110.0 . . ?
O7 C14 H14B 110.0 . . ?
C13 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
O7 C15 C16 109.1(2) . . ?
O7 C15 H15A 109.9 . . ?
C16 C15 H15A 109.9 . . ?
O7 C15 H15B 109.9 . . ?
C16 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
O8 C16 C15 109.9(2) . . ?
O8 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
O8 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
O8 C17 C18 109.3(2) . . ?
O8 C17 H17A 109.8 . . ?
C18 C17 H17A 109.8 . . ?
O8 C17 H17B 109.8 . . ?
C18 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
O3 C18 C17 109.2(2) . . ?
O3 C18 H18A 109.8 . . ?
C17 C18 H18A 109.8 . . ?
O3 C18 H18B 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.3 . . ?
C2 N1 H1B 114(3) . . ?
C2 N1 H1A 120(3) . . ?
H1B N1 H1A 125(4) . . ?
C6 C1 N3 117.9(2) . . ?
C6 C1 C2 119.7(2) . . ?
N3 C1 C2 122.4(2) . . ?
C4 N2 H2A 119(3) . . ?
C4 N2 H2B 113(3) . . ?
H2A N2 H2B 128(4) . . ?
N1 C2 C3 118.9(2) . . ?
N1 C2 C1 124.5(2) . . ?
C3 C2 C1 116.6(2) . . ?
O2 N3 O1 121.0(3) . . ?
O2 N3 C1 120.1(2) . . ?
O1 N3 C1 118.9(3) . . ?
C4 C3 C2 123.3(2) . . ?
C4 C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
N2 C4 C3 121.7(2) . . ?
N2 C4 C5 119.8(3) . . ?
C3 C4 C5 118.5(2) . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 122.1(2) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 O3 C7 C8 -172.1(3) . . . . ?
C9 O4 C8 C7 177.2(2) . . . . ?
O3 C7 C8 O4 69.3(3) . . . . ?
C8 O4 C9 C10 177.6(2) . . . . ?
C11 O5 C10 C9 -174.3(2) . . . . ?
O4 C9 C10 O5 -75.2(3) . . . . ?
C10 O5 C11 C12 -168.2(2) . . . . ?
C13 O6 C12 C11 -175.5(2) . . . . ?
O5 C11 C12 O6 65.7(3) . . . . ?
C12 O6 C13 C14 176.2(2) . . . . ?
C15 O7 C14 C13 -174.8(2) . . . . ?
O6 C13 C14 O7 -67.5(3) . . . . ?
C14 O7 C15 C16 176.4(2) . . . . ?
C17 O8 C16 C15 176.3(2) . . . . ?
O7 C15 C16 O8 73.0(3) . . . . ?
C16 O8 C17 C18 169.7(2) . . . . ?
C7 O3 C18 C17 176.6(2) . . . . ?
O8 C17 C18 O3 -68.8(3) . . . . ?
C6 C1 C2 N1 -179.1(3) . . . . ?
N3 C1 C2 N1 1.3(4) . . . . ?
C6 C1 C2 C3 2.4(3) . . . . ?
N3 C1 C2 C3 -177.2(2) . . . . ?
C6 C1 N3 O2 -178.6(3) . . . . ?
C2 C1 N3 O2 1.0(4) . . . . ?
C6 C1 N3 O1 0.1(4) . . . . ?
C2 C1 N3 O1 179.7(3) . . . . ?
N1 C2 C3 C4 178.8(3) . . . . ?
C1 C2 C3 C4 -2.5(4) . . . . ?
C2 C3 C4 N2 -178.1(3) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
N2 C4 C5 C6 179.8(3) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
N3 C1 C6 C5 178.8(3) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.040


