# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2075033'
loop_
_audit_author_name
_audit_author_address
'Boris Zakharov'
;Boreskov Institute of Catalysis SB RAS
Russia
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2,4-diamino-3,5,6-trifluorobenzonitrile--18-crown-6 ether (4:3)
;
_chemical_name_common            
;
2,4-diamino-3,5,6-trifluorobenzonitrile--18-crown-6 ether (4:3)
;
_chemical_melting_point          393
_chemical_formula_moiety         '3(C12 H24 O6), 4(C7 H4 F3 N3)'
_chemical_formula_sum            'C64 H88 F12 N12 O18'
_chemical_formula_weight         1541.46

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'
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                   11.7416(7)
_cell_length_b                   12.0658(10)
_cell_length_c                   15.0919(10)
_cell_angle_alpha                113.393(7)
_cell_angle_beta                 98.517(5)
_cell_angle_gamma                103.527(6)
_cell_volume                     1837.0(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3011
_cell_measurement_theta_min      4.4570
_cell_measurement_theta_max      26.6530

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_T_max  1.144
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.3457
_diffrn_reflns_number            10728
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.853
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             6512
_reflns_number_gt                3576
_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       
'CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)'
_computing_cell_refinement       
'CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)'
_computing_data_reduction        
'CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0433P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         6512
_refine_ls_number_parameters     584
_refine_ls_number_restraints     198
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   0.846
_refine_ls_restrained_S_all      0.836
_refine_ls_shift/su_max          0.001
_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 0.22034(8) 0.75294(10) 0.41374(7) 0.0588(3) Uani 1 1 d . . . . .
O1 O 0.47215(11) -0.06389(11) 0.23877(10) 0.0591(4) Uani 1 1 d . . . . .
N1 N -0.28087(15) 0.74403(16) 0.31118(13) 0.0666(5) Uani 1 1 d . . . . .
C1 C -0.18566(17) 0.77428(17) 0.36227(14) 0.0462(5) Uani 1 1 d . . . . .
F2 F 0.08472(10) 0.96911(11) 0.69086(8) 0.0752(4) Uani 1 1 d . . . . .
O2 O 0.48515(12) 0.12630(13) 0.42841(11) 0.0695(4) Uani 1 1 d . . . . .
N2 N 0.00556(16) 0.69713(18) 0.28450(12) 0.0591(5) Uani 1 1 d . . . . .
H2A H 0.0557(18) 0.6649(19) 0.2628(15) 0.071 Uiso 1 1 d . U . . .
H2B H -0.0519(18) 0.6930(19) 0.2442(16) 0.071 Uiso 1 1 d . U . . .
C2 C -0.06839(14) 0.80698(15) 0.42463(13) 0.0387(4) Uani 1 1 d . . . . .
F3 F -0.13099(9) 0.91593(11) 0.56644(8) 0.0689(3) Uani 1 1 d . . . . .
O3 O 0.60549(14) 0.38289(14) 0.47523(11) 0.0778(4) Uani 1 1 d . . . . .
N3 N 0.26610(15) 0.88776(17) 0.61682(13) 0.0579(5) Uani 1 1 d . . . . .
H3A H 0.3152(17) 0.8480(18) 0.5937(15) 0.070 Uiso 1 1 d . U . . .
H3B H 0.2734(17) 0.9189(18) 0.6825(16) 0.070 Uiso 1 1 d . U . . .
C3 C 0.02305(15) 0.76470(15) 0.38434(13) 0.0387(4) Uani 1 1 d . . . . .
N4 N 0.14679(16) 0.51295(17) 0.19336(14) 0.0727(5) Uani 1 1 d . . . . .
C4 C 0.13084(15) 0.79283(16) 0.45181(13) 0.0403(4) Uani 1 1 d . . . . .
F5 F 0.28856(10) 0.08174(10) 0.19539(10) 0.0801(4) Uani 1 1 d . . . . .
O5 O 0.80527(12) 0.24483(14) 0.21661(12) 0.0712(4) Uani 1 1 d . . . . .
N5 N 0.45602(16) 0.55353(16) 0.20762(14) 0.0602(5) Uani 1 1 d . . . . .
H5A H 0.5303(18) 0.5986(19) 0.2311(15) 0.072 Uiso 1 1 d . U . . .
H5B H 0.4056(18) 0.593(2) 0.2028(15) 0.072 Uiso 1 1 d . U . . .
C5 C 0.15729(15) 0.85930(16) 0.55466(14) 0.0421(4) Uani 1 1 d . . . . .
N6 N 0.53233(16) 0.18764(17) 0.22171(14) 0.0616(5) Uani 1 1 d . . . . .
H6A H 0.6095(19) 0.2258(19) 0.2389(16) 0.074 Uiso 1 1 d . U . . .
H6B H 0.5072(18) 0.125(2) 0.2306(16) 0.074 Uiso 1 1 d . U . . .
O6 O 0.66654(12) -0.01456(13) 0.14872(9) 0.0602(4) Uani 1 1 d . . . . .
F6 F 0.13295(9) 0.20931(11) 0.18051(10) 0.0809(4) Uani 1 1 d . . . . .
C6 C 0.06410(16) 0.90034(16) 0.59078(13) 0.0467(5) Uani 1 1 d . . . . .
C7 C -0.04400(16) 0.87520(16) 0.52816(14) 0.0448(5) Uani 1 1 d . . . . .
C8 C 0.20771(17) 0.45181(19) 0.19264(14) 0.0508(5) Uani 1 1 d . . . . .
C9 C 0.28970(15) 0.38262(16) 0.19563(12) 0.0410(4) Uani 1 1 d . . . . .
C26 C 0.7095(2) 0.0363(2) 0.08610(16) 0.0768(7) Uani 1 1 d . . . . .
H26A H 0.650520 0.069199 0.061791 0.092 Uiso 1 1 calc R U . . .
H26B H 0.720617 -0.030112 0.028683 0.092 Uiso 1 1 calc R U . . .
C25 C 0.8267(2) 0.1402(2) 0.14308(18) 0.0784(7) Uani 1 1 d . . . . .
H25A H 0.882281 0.110501 0.175087 0.094 Uiso 1 1 calc R U . . .
H25B H 0.863308 0.166300 0.097974 0.094 Uiso 1 1 calc R U . . .
C24 C 0.9147(2) 0.3370(2) 0.2863(2) 0.0874(8) Uani 1 1 d . . . . .
H24A H 0.971002 0.360742 0.250915 0.105 Uiso 1 1 calc R U . . .
H24B H 0.952109 0.301739 0.325756 0.105 Uiso 1 1 calc R U . . .
C23 C 0.8885(2) 0.4506(2) 0.3528(2) 0.0886(8) Uani 1 1 d . . . . .
H23A H 0.964280 0.518083 0.394988 0.106 Uiso 1 1 calc R U . . .
H23B H 0.844468 0.481137 0.312780 0.106 Uiso 1 1 calc R U . . .
C22 C 0.7786(2) 0.5215(2) 0.46861(19) 0.0921(8) Uani 1 1 d . . . . .
H22A H 0.725715 0.538547 0.423312 0.111 Uiso 1 1 calc R U . . .
H22B H 0.847740 0.598182 0.508865 0.111 Uiso 1 1 calc R U . . .
C21 C 0.7122(3) 0.4871(2) 0.53403(19) 0.0902(8) Uani 1 1 d . . . . .
H21A H 0.763372 0.464804 0.576382 0.108 Uiso 1 1 calc R U . . .
H21B H 0.691209 0.559460 0.576943 0.108 Uiso 1 1 calc R U . . .
C20 C 0.5402(2) 0.3470(2) 0.53524(18) 0.0827(7) Uani 1 1 d . . . . .
H20A H 0.508570 0.414046 0.571648 0.099 Uiso 1 1 calc R U . . .
H20B H 0.593756 0.335200 0.583739 0.099 Uiso 1 1 calc R U . . .
F4 F 0.60987(9) 0.42382(10) 0.22973(9) 0.0673(3) Uani 1 1 d . . . . .
O4 O 0.81902(14) 0.42068(14) 0.41301(12) 0.0816(5) Uani 1 1 d . . . . .
C10 C 0.41309(15) 0.43801(16) 0.20717(12) 0.0402(4) Uani 1 1 d . . . . .
C11 C 0.48944(14) 0.37005(17) 0.21707(13) 0.0430(4) Uani 1 1 d . . . . .
C12 C 0.45415(15) 0.25153(16) 0.21513(12) 0.0422(4) Uani 1 1 d . . . . .
C13 C 0.32967(16) 0.19952(17) 0.20109(14) 0.0484(5) Uani 1 1 d . . . . .
C14 C 0.25145(15) 0.26299(18) 0.19220(14) 0.0482(5) Uani 1 1 d . . . . .
C15 C 0.5548(2) -0.1160(2) 0.10048(16) 0.0720(7) Uani 1 1 d . . . . .
H15A H 0.565238 -0.187085 0.046244 0.086 Uiso 1 1 calc R U . . .
H15B H 0.493883 -0.088248 0.072326 0.086 Uiso 1 1 calc R U . . .
C16 C 0.51456(19) -0.15673(18) 0.17391(17) 0.0692(6) Uani 1 1 d . . . . .
H16A H 0.449945 -0.238217 0.139282 0.083 Uiso 1 1 calc R U . . .
H16B H 0.581797 -0.166838 0.212394 0.083 Uiso 1 1 calc R U . . .
C17 C 0.4426(2) -0.0906(2) 0.31711(18) 0.0746(7) Uani 1 1 d . . . . .
H17A H 0.514799 -0.089574 0.358544 0.090 Uiso 1 1 calc R U . . .
H17B H 0.382860 -0.174811 0.289322 0.090 Uiso 1 1 calc R U . . .
C18 C 0.39285(19) 0.0067(2) 0.37886(18) 0.0770(7) Uani 1 1 d . . . . .
H18A H 0.325336 0.011291 0.336354 0.092 Uiso 1 1 calc R U . . .
H18B H 0.363135 -0.016748 0.427704 0.092 Uiso 1 1 calc R U . . .
C19 C 0.4391(2) 0.2281(2) 0.47293(18) 0.0809(7) Uani 1 1 d . . . . .
H19A H 0.388783 0.209145 0.513887 0.097 Uiso 1 1 calc R U . . .
H19B H 0.389118 0.237681 0.420985 0.097 Uiso 1 1 calc R U . . .
C27A C 0.1693(8) 0.7252(10) 0.0680(9) 0.071(2) Uani 0.515(12) 1 d D U P A 1
H27A H 0.180184 0.725101 0.132976 0.085 Uiso 0.515(12) 1 calc R U P A 1
H27B H 0.232994 0.796956 0.073239 0.085 Uiso 0.515(12) 1 calc R U P A 1
O7A O 0.0542(6) 0.7335(9) 0.0365(5) 0.087(3) Uani 0.515(12) 1 d D U P A 1
C28A C 0.0269(11) 0.8320(11) 0.1107(11) 0.073(3) Uani 0.515(12) 1 d D U P A 1
H28A H 0.064221 0.913169 0.111341 0.087 Uiso 0.515(12) 1 calc R U P A 1
H28B H 0.057699 0.838312 0.176372 0.087 Uiso 0.515(12) 1 calc R U P A 1
C29A C -0.1087(12) 0.7999(10) 0.0856(13) 0.060(3) Uani 0.515(12) 1 d D U P A 1
H29A H -0.132227 0.869556 0.129488 0.073 Uiso 0.515(12) 1 calc R U P A 1
H29B H -0.141839 0.781455 0.016616 0.073 Uiso 0.515(12) 1 calc R U P A 1
O8A O -0.1493(7) 0.6903(10) 0.1009(8) 0.046(2) Uani 0.515(12) 1 d D U P A 1
C30A C -0.2764(9) 0.6309(13) 0.0622(12) 0.070(3) Uani 0.515(12) 1 d D U P A 1
H30A H -0.300553 0.623068 -0.004895 0.085 Uiso 0.515(12) 1 calc R U P A 1
H30B H -0.316392 0.684824 0.103561 0.085 Uiso 0.515(12) 1 calc R U P A 1
C31A C -0.3187(11) 0.5018(13) 0.0582(9) 0.072(3) Uani 0.515(12) 1 d D U P A 1
H31A H -0.282982 0.507330 0.122622 0.086 Uiso 0.515(12) 1 calc R U P A 1
H31B H -0.406318 0.475538 0.046827 0.086 Uiso 0.515(12) 1 calc R U P A 1
O9A O -0.2888(7) 0.4088(8) -0.0166(7) 0.085(2) Uani 0.515(12) 1 d D U P A 1
C32A C -0.1736(9) 0.3976(12) 0.0099(9) 0.084(4) Uani 0.515(12) 1 d D U P A 1
H32A H -0.159364 0.398225 0.075051 0.100 Uiso 0.515(12) 1 calc R U P A 1
H32B H -0.110865 0.469025 0.013550 0.100 Uiso 0.515(12) 1 calc R U P A 1
C27B C 0.1098(12) 0.7123(10) 0.0650(10) 0.075(3) Uani 0.485(12) 1 d D U P A 2
H27C H 0.041638 0.641072 0.055014 0.091 Uiso 0.485(12) 1 calc R U P A 2
H27D H 0.160122 0.749516 0.133324 0.091 Uiso 0.485(12) 1 calc R U P A 2
O7B O 0.0680(7) 0.8032(9) 0.0481(6) 0.0806(19) Uani 0.485(12) 1 d D U P A 2
C28B C 0.0076(13) 0.8639(13) 0.1172(13) 0.072(3) Uani 0.485(12) 1 d D U P A 2
H28C H 0.015136 0.947393 0.120598 0.087 Uiso 0.485(12) 1 calc R U P A 2
H28D H 0.047616 0.876533 0.183101 0.087 Uiso 0.485(12) 1 calc R U P A 2
C29B C -0.1257(13) 0.7908(14) 0.0917(15) 0.068(4) Uani 0.485(12) 1 d D U P A 2
H29C H -0.163638 0.847161 0.133317 0.081 Uiso 0.485(12) 1 calc R U P A 2
H29D H -0.162743 0.768986 0.022555 0.081 Uiso 0.485(12) 1 calc R U P A 2
O8B O -0.1532(9) 0.6794(12) 0.1031(9) 0.067(4) Uani 0.485(12) 1 d D U P A 2
C30B C -0.2784(11) 0.6090(12) 0.0663(9) 0.056(3) Uani 0.485(12) 1 d D U P A 2
H30C H -0.311306 0.600215 0.000120 0.068 Uiso 0.485(12) 1 calc R U P A 2
H30D H -0.323579 0.649712 0.110958 0.068 Uiso 0.485(12) 1 calc R U P A 2
C31B C -0.2835(11) 0.4821(12) 0.0626(9) 0.067(3) Uani 0.485(12) 1 d D U P A 2
H31C H -0.237959 0.494000 0.126589 0.080 Uiso 0.485(12) 1 calc R U P A 2
H31D H -0.367231 0.432054 0.049573 0.080 Uiso 0.485(12) 1 calc R U P A 2
O9B O -0.2334(10) 0.4168(7) -0.0143(6) 0.072(3) Uani 0.485(12) 1 d D U P A 2
C32B C -0.1814(9) 0.3318(12) 0.0064(10) 0.080(3) Uani 0.485(12) 1 d D U P A 2
H32C H -0.245262 0.259383 0.000149 0.096 Uiso 0.485(12) 1 calc R U P A 2
H32D H -0.129323 0.374858 0.074508 0.096 Uiso 0.485(12) 1 calc R U P A 2


_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 C4 1.3646(18) . ?
O1 C17 1.412(3) . ?
O1 C16 1.413(2) . ?
N1 C1 1.144(2) . ?
C1 C2 1.416(2) . ?
F2 C6 1.353(2) . ?
O2 C18 1.410(2) . ?
O2 C19 1.419(2) . ?
N2 C3 1.353(2) . ?
C2 C7 1.392(2) . ?
C2 C3 1.409(2) . ?
F3 C7 1.3427(18) . ?
O3 C20 1.399(3) . ?
O3 C21 1.410(3) . ?
N3 C5 1.347(2) . ?
C3 C4 1.377(2) . ?
N4 C8 1.140(2) . ?
C4 C5 1.379(2) . ?
F5 C13 1.353(2) . ?
O5 C24 1.413(2) . ?
O5 C25 1.417(2) . ?
N5 C10 1.364(2) . ?
C5 C6 1.398(2) . ?
N6 C12 1.346(2) . ?
O6 C26 1.408(3) . ?
O6 C15 1.417(2) . ?
F6 C14 1.3423(18) . ?
C6 C7 1.354(2) . ?
C8 C9 1.421(3) . ?
C9 C14 1.385(2) . ?
C9 C10 1.399(2) . ?
C26 C25 1.480(3) . ?
C24 C23 1.476(3) . ?
C23 O4 1.401(3) . ?
C22 O4 1.410(3) . ?
C22 C21 1.468(3) . ?
C20 C19 1.467(3) . ?
F4 C11 1.3598(18) . ?
C10 C11 1.378(2) . ?
C11 C12 1.380(2) . ?
C12 C13 1.396(2) . ?
C13 C14 1.350(2) . ?
C15 C16 1.474(3) . ?
C17 C18 1.484(3) . ?
C27A O7A 1.405(8) . ?
C27A C32A 1.500(15) 2_565 ?
O7A C28A 1.414(9) . ?
C28A C29A 1.498(10) . ?
C29A O8A 1.418(9) . ?
O8A C30A 1.410(10) . ?
C30A C31A 1.494(10) . ?
C31A O9A 1.397(9) . ?
O9A C32A 1.405(9) . ?
C27B O7B 1.396(9) . ?
C27B C32B 1.475(15) 2_565 ?
O7B C28B 1.409(10) . ?
C28B C29B 1.511(11) . ?
C29B O8B 1.393(11) . ?
O8B C30B 1.411(10) . ?
C30B C31B 1.496(10) . ?
C31B O9B 1.417(10) . ?
O9B C32B 1.418(9) . ?

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
C17 O1 C16 112.34(17) . . ?
N1 C1 C2 177.90(19) . . ?
C18 O2 C19 112.39(16) . . ?
C7 C2 C3 118.72(16) . . ?
C7 C2 C1 120.06(16) . . ?
C3 C2 C1 121.09(16) . . ?
C20 O3 C21 111.30(18) . . ?
N2 C3 C4 121.26(16) . . ?
N2 C3 C2 122.01(16) . . ?
C4 C3 C2 116.72(16) . . ?
F1 C4 C3 117.30(15) . . ?
F1 C4 C5 116.83(15) . . ?
C3 C4 C5 125.87(16) . . ?
C24 O5 C25 111.84(17) . . ?
N3 C5 C4 123.19(17) . . ?
N3 C5 C6 121.59(17) . . ?
C4 C5 C6 115.18(16) . . ?
C26 O6 C15 113.76(17) . . ?
F2 C6 C7 119.85(16) . . ?
F2 C6 C5 118.48(16) . . ?
C7 C6 C5 121.65(16) . . ?
F3 C7 C6 119.47(16) . . ?
F3 C7 C2 118.67(16) . . ?
C6 C7 C2 121.85(17) . . ?
N4 C8 C9 176.5(2) . . ?
C14 C9 C10 118.65(15) . . ?
C14 C9 C8 121.46(16) . . ?
C10 C9 C8 119.83(17) . . ?
O6 C26 C25 109.47(18) . . ?
O5 C25 C26 108.93(17) . . ?
O5 C24 C23 109.47(18) . . ?
O4 C23 C24 110.2(2) . . ?
O4 C22 C21 109.7(2) . . ?
O3 C21 C22 109.7(2) . . ?
O3 C20 C19 110.19(19) . . ?
C23 O4 C22 112.3(2) . . ?
N5 C10 C11 121.36(16) . . ?
N5 C10 C9 121.59(16) . . ?
C11 C10 C9 117.05(16) . . ?
F4 C11 C10 117.54(16) . . ?
F4 C11 C12 116.92(15) . . ?
C10 C11 C12 125.54(16) . . ?
N6 C12 C11 122.91(17) . . ?
N6 C12 C13 122.07(18) . . ?
C11 C12 C13 114.95(15) . . ?
C14 C13 F5 120.37(16) . . ?
C14 C13 C12 121.71(17) . . ?
F5 C13 C12 117.91(15) . . ?
F6 C14 C13 119.17(17) . . ?
F6 C14 C9 118.75(15) . . ?
C13 C14 C9 122.08(16) . . ?
O6 C15 C16 109.29(16) . . ?
O1 C16 C15 109.22(17) . . ?
O1 C17 C18 109.35(18) . . ?
O2 C18 C17 109.26(16) . . ?
O2 C19 C20 109.95(17) . . ?
O7A C27A C32A 106.3(9) . 2_565 ?
C27A O7A C28A 113.3(8) . . ?
O7A C28A C29A 107.5(10) . . ?
O8A C29A C28A 104.0(12) . . ?
C30A O8A C29A 112.1(10) . . ?
O8A C30A C31A 113.2(13) . . ?
O9A C31A C30A 113.6(11) . . ?
C31A O9A C32A 116.1(8) . . ?
O9A C32A C27A 108.6(9) . 2_565 ?
O7B C27B C32B 107.8(9) . 2_565 ?
C27B O7B C28B 114.7(9) . . ?
O7B C28B C29B 113.9(13) . . ?
O8B C29B C28B 116.6(13) . . ?
C29B O8B C30B 113.0(11) . . ?
O8B C30B C31B 103.9(12) . . ?
O9B C31B C30B 109.5(10) . . ?
C31B O9B C32B 112.2(8) . . ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.135
_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_Bcr-c25_50ff
_database_code_depnum_ccdc_archive 'CCDC 2076049'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2021-04-09 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2,4-diamino-3,5-difluorobenzonitrile and 18-crown-6, 1:1 co-crystal
;
_chemical_name_common            ?
_chemical_melting_point          381
_chemical_formula_moiety         'C12 H24 O6, C7 H5 F2 N3'
_chemical_formula_sum            'C19 H29 F2 N3 O6'
_chemical_formula_weight         433.45

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      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                   7.664(6)
_cell_length_b                   10.486(8)
_cell_length_c                   15.090(9)
_cell_angle_alpha                74.090(19)
_cell_angle_beta                 87.76(3)
_cell_angle_gamma                69.95(2)
_cell_volume                     1093.5(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1201
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      21.25

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.510
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8418
_exptl_absorpt_correction_T_max  0.9801
_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            6922
_diffrn_reflns_av_unetI/netI     0.0969
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.406
_diffrn_reflns_theta_max         25.244
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             3874
_reflns_number_gt                2094
_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-2018/2 (Sheldrick, 2018)'
_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)+(0.1500P)²+8.1230P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3874
_refine_ls_number_parameters     269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1965
_refine_ls_R_factor_gt           0.1455
_refine_ls_wR_factor_ref         0.4386
_refine_ls_wR_factor_gt          0.4064
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.003
_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 -0.1287(8) 0.2500(5) 0.9784(4) 0.0497(15) Uani 1 1 d . . . . .
F1 F 0.7404(8) 0.2953(5) 0.7602(3) 0.0661(16) Uani 1 1 d . . . . .
N2 N 0.8453(10) 0.0284(7) 0.8795(4) 0.0458(16) Uani 1 1 d . . . . .
H2A H 0.812830 0.099685 0.901944 0.055 Uiso 1 1 calc R U . . .
H2B H 0.880676 -0.056044 0.915918 0.055 Uiso 1 1 calc R U . . .
C1 C 0.8870(10) -0.0640(8) 0.7469(5) 0.0401(17) Uani 1 1 d . . . . .
F2 F 0.8341(10) 0.1177(7) 0.5023(4) 0.096(2) Uani 1 1 d . . . . .
O2 O 0.1687(9) 0.1697(7) 0.8636(4) 0.0644(18) Uani 1 1 d . . . . .
C3 C 0.7851(11) 0.1826(8) 0.7244(5) 0.0444(19) Uani 1 1 d . . . . .
C5 C 0.8329(12) 0.0925(10) 0.5957(5) 0.055(2) Uani 1 1 d . . . . .
C4 C 0.7754(10) 0.2110(8) 0.6286(5) 0.0440(19) Uani 1 1 d . . . . .
N3 N 0.7230(10) 0.3463(8) 0.5703(5) 0.060(2) Uani 1 1 d . . . . .
H3A H 0.725370 0.359291 0.511523 0.073 Uiso 1 1 calc R U . . .
H3B H 0.687964 0.417602 0.592683 0.073 Uiso 1 1 calc R U . . .
C2 C 0.8407(10) 0.0493(8) 0.7861(5) 0.0391(17) Uani 1 1 d . . . . .
C6 C 0.8865(13) -0.0413(9) 0.6505(6) 0.057(2) Uani 1 1 d . . . . .
H6 H 0.922411 -0.117210 0.625144 0.068 Uiso 1 1 calc R U . . .
O1 O 0.2843(9) -0.1304(7) 0.8641(5) 0.073(2) Uani 1 1 d . . . . .
O5 O 0.4476(18) 0.6186(10) 0.6361(7) 0.127(5) Uani 1 1 d . . . . .
C7 C 0.9254(14) -0.2070(9) 0.8047(6) 0.055(2) Uani 1 1 d . . . . .
O6 O 0.2889(14) 0.4018(12) 0.6469(7) 0.117(3) Uani 1 1 d . . . . .
N1 N 0.9473(16) -0.3179(9) 0.8480(6) 0.087(3) Uani 1 1 d . . . . .
C12 C -0.3108(14) 0.3209(11) 1.0062(8) 0.074(3) Uani 1 1 d . . . . .
H12A H -0.390831 0.383808 0.952268 0.088 Uiso 1 1 calc R U . . .
H12B H -0.300626 0.376809 1.046103 0.088 Uiso 1 1 calc R U . . .
C10 C 0.1565(15) 0.2623(11) 0.9185(7) 0.067(3) Uani 1 1 d . . . . .
H10A H 0.221994 0.326421 0.890630 0.081 Uiso 1 1 calc R U . . .
H10B H 0.215277 0.207950 0.979418 0.081 Uiso 1 1 calc R U . . .
C11 C -0.0429(16) 0.3454(10) 0.9270(6) 0.071(3) Uani 1 1 d . . . . .
H11A H -0.050226 0.416259 0.958351 0.085 Uiso 1 1 calc R U . . .
H11B H -0.105744 0.392907 0.866258 0.085 Uiso 1 1 calc R U . . .
C8 C 0.3562(15) -0.0285(14) 0.8100(9) 0.087(4) Uani 1 1 d . . . . .
H8A H 0.284154 0.015808 0.751327 0.104 Uiso 1 1 calc R U . . .
H8B H 0.483190 -0.076804 0.797243 0.104 Uiso 1 1 calc R U . . .
C16 C 0.3364(17) 0.5598(15) 0.7141(7) 0.099(5) Uani 1 1 d . . . . .
H16A H 0.416540 0.472454 0.755841 0.119 Uiso 1 1 calc R U . . .
H16B H 0.281372 0.627459 0.748931 0.119 Uiso 1 1 calc R U . . .
C9 C 0.3556(15) 0.0871(12) 0.8535(8) 0.080(3) Uani 1 1 d . . . . .
H9A H 0.422943 0.044683 0.913449 0.096 Uiso 1 1 calc R U . . .
H9B H 0.417178 0.147057 0.814705 0.096 Uiso 1 1 calc R U . . .
C13 C -0.3907(14) 0.2146(14) 1.0554(8) 0.084(4) Uani 1 1 d . . . . .
H13A H -0.516799 0.261290 1.070164 0.101 Uiso 1 1 calc R U . . .
H13B H -0.395661 0.156353 1.016208 0.101 Uiso 1 1 calc R U . . .
O4 O 0.699(2) 0.6808(16) 0.5176(10) 0.157(6) Uani 1 1 d . . . . .
C18 C 0.168(2) 0.350(2) 0.6214(10) 0.122(6) Uani 1 1 d . . . . .
H18A H 0.060136 0.427175 0.588118 0.146 Uiso 1 1 calc R U . . .
H18B H 0.126429 0.296278 0.675709 0.146 Uiso 1 1 calc R U . . .
C17 C 0.189(2) 0.5342(19) 0.6673(13) 0.136(7) Uani 1 1 d . . . . .
H17A H 0.089657 0.525931 0.707737 0.163 Uiso 1 1 calc R U . . .
H17B H 0.137265 0.609441 0.611244 0.163 Uiso 1 1 calc R U . . .
C14 C 0.619(3) 0.747(3) 0.587(2) 0.176(11) Uani 1 1 d . . . . .
H14A H 0.523580 0.835543 0.556291 0.211 Uiso 1 1 calc R U . . .
H14B H 0.715108 0.769371 0.612383 0.211 Uiso 1 1 calc R U . . .
C15 C 0.535(4) 0.671(3) 0.6659(16) 0.186(13) Uani 1 1 d . . . . .
H15A H 0.631314 0.600242 0.710231 0.223 Uiso 1 1 calc R U . . .
H15B H 0.454869 0.738043 0.696726 0.223 Uiso 1 1 calc R U . . .
C19 C 0.265(3) 0.250(2) 0.5567(18) 0.172(10) Uani 1 1 d . . . . .
H19A H 0.378474 0.178035 0.588171 0.206 Uiso 1 1 calc R U . . .
H19B H 0.182038 0.203329 0.545254 0.206 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 C11 1.421(10) . ?
O3 C12 1.446(11) . ?
F1 C3 1.366(9) . ?
N2 C2 1.365(9) . ?
C1 C2 1.403(11) . ?
C1 C6 1.408(11) . ?
C1 C7 1.448(11) . ?
F2 C5 1.360(9) . ?
O2 C10 1.418(12) . ?
O2 C9 1.424(12) . ?
C3 C2 1.383(10) . ?
C3 C4 1.392(11) . ?
C5 C6 1.348(12) . ?
C5 C4 1.389(12) . ?
C4 N3 1.379(10) . ?
O1 C13 1.385(13) 2_557 ?
O1 C8 1.415(12) . ?
O5 C15 1.17(3) . ?
O5 C16 1.541(17) . ?
C7 N1 1.125(11) . ?
O6 C18 1.338(17) . ?
O6 C17 1.447(17) . ?
C12 C13 1.465(16) . ?
C10 C11 1.498(15) . ?
C8 C9 1.528(17) . ?
C16 C17 1.49(2) . ?
O4 C19 1.24(2) 2_666 ?
O4 C14 1.41(3) . ?
C18 C19 1.60(3) . ?
C14 C15 1.50(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
C11 O3 C12 113.0(8) . . ?
C2 C1 C6 121.2(7) . . ?
C2 C1 C7 120.5(7) . . ?
C6 C1 C7 118.2(7) . . ?
C10 O2 C9 112.9(8) . . ?
F1 C3 C2 117.3(7) . . ?
F1 C3 C4 117.4(7) . . ?
C2 C3 C4 125.3(8) . . ?
C6 C5 F2 120.1(9) . . ?
C6 C5 C4 123.8(8) . . ?
F2 C5 C4 116.1(7) . . ?
N3 C4 C5 122.0(7) . . ?
N3 C4 C3 122.8(8) . . ?
C5 C4 C3 115.1(7) . . ?
N2 C2 C3 122.5(7) . . ?
N2 C2 C1 121.7(7) . . ?
C3 C2 C1 115.7(7) . . ?
C5 C6 C1 118.8(8) . . ?
C13 O1 C8 114.1(9) 2_557 . ?
C15 O5 C16 108.3(19) . . ?
N1 C7 C1 176.7(11) . . ?
C18 O6 C17 109.8(14) . . ?
O3 C12 C13 109.0(8) . . ?
O2 C10 C11 110.4(8) . . ?
O3 C11 C10 108.1(8) . . ?
O1 C8 C9 115.2(9) . . ?
C17 C16 O5 105.6(10) . . ?
O2 C9 C8 109.6(9) . . ?
O1 C13 C12 110.3(10) 2_557 . ?
C19 O4 C14 121(2) 2_666 . ?
O6 C18 C19 110.0(13) . . ?
O6 C17 C16 102.8(11) . . ?
O4 C14 C15 120.0(18) . . ?
O5 C15 C14 107.6(18) . . ?
O4 C19 C18 111(2) 2_666 . ?

_refine_diff_density_max         0.681
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.118

####################################################################### 
# 
# 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-OP804
_database_code_depnum_ccdc_archive 'CCDC 2076050'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2,6-diamino-3,5-difluorobenzonitrile and 18-crown-6, 1:1 co-crystal
;
_chemical_name_common            ?
_chemical_melting_point          398
_chemical_formula_moiety         'C12 H24 O6, C7 H5 F2 N3'
_chemical_formula_sum            'C19 H29 F2 N3 O6'
_chemical_formula_weight         433.45

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           15
_space_group_name_H-M_alt        'C 2/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'
'-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                   13.4328(6)
_cell_length_b                   16.8984(8)
_cell_length_c                   9.2577(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.591(2)
_cell_angle_gamma                90
_cell_volume                     2087.54(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5022
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      26.77

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9171
_exptl_absorpt_correction_T_max  0.9878
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(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            15279
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.813
_diffrn_reflns_theta_max         27.502
_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             2384
_reflns_number_gt                1842
_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-2018/2 (Sheldrick, 2018)'
_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)+(0.0694P)²+0.7114P] 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         2384
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.1138
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_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
N2 N 0.61014(9) 0.28376(7) 0.05634(12) 0.0275(3) Uani 1 1 d . . . . .
H2A H 0.6599(15) 0.3123(11) 0.031(2) 0.045(5) Uiso 1 1 d . . . . .
H2B H 0.6344(12) 0.2375(10) 0.0876(19) 0.037(4) Uiso 1 1 d . . . . .
N1 N 0.500000 0.13051(10) 0.250000 0.0425(5) Uani 1 2 d S T P . .
F1 F 0.59878(6) 0.44659(5) 0.05563(10) 0.0375(2) Uani 1 1 d . . . . .
C1 C 0.500000 0.28331(10) 0.250000 0.0217(4) Uani 1 2 d S T P . .
C2 C 0.55660(9) 0.32324(7) 0.15272(13) 0.0225(3) Uani 1 1 d . . . . .
C4 C 0.500000 0.44688(11) 0.250000 0.0285(4) Uani 1 2 d S T P . .
H4 H 0.500000 0.503100 0.250003 0.034 Uiso 1 2 calc R U P . .
C5 C 0.500000 0.19848(11) 0.250000 0.0261(4) Uani 1 2 d S T P . .
C3 C 0.55087(9) 0.40544(8) 0.15377(14) 0.0262(3) Uani 1 1 d . . . . .
O2 O 0.71998(7) 0.11908(5) 0.07540(10) 0.0260(2) Uani 1 1 d . . . . .
O1 O 0.71288(7) 0.11844(6) -0.23096(10) 0.0310(2) Uani 1 1 d . . . . .
O3 O 0.78721(7) 0.21441(5) 0.31133(11) 0.0318(2) Uani 1 1 d . . . . .
C8 C 0.66441(11) 0.06249(8) -0.01465(15) 0.0309(3) Uani 1 1 d . . . . .
H8A H 0.606183 0.044161 0.032860 0.037 Uiso 1 1 calc R U . . .
H8B H 0.707169 0.016098 -0.029143 0.037 Uiso 1 1 calc R U . . .
C10 C 0.83184(11) 0.13967(8) 0.29026(15) 0.0312(3) Uani 1 1 d . . . . .
H10A H 0.858404 0.116672 0.385282 0.037 Uiso 1 1 calc R U . . .
H10B H 0.888135 0.145980 0.230936 0.037 Uiso 1 1 calc R U . . .
C9 C 0.75421(11) 0.08634(8) 0.21454(15) 0.0301(3) Uani 1 1 d . . . . .
H9A H 0.783026 0.033141 0.202557 0.036 Uiso 1 1 calc R U . . .
H9B H 0.697345 0.080957 0.273041 0.036 Uiso 1 1 calc R U . . .
C11 C 0.85748(13) 0.26918(9) 0.37945(17) 0.0417(4) Uani 1 1 d . . . . .
H11A H 0.918621 0.269420 0.329068 0.050 Uiso 1 1 calc R U . . .
H11B H 0.876687 0.253559 0.481922 0.050 Uiso 1 1 calc R U . . .
C7 C 0.62887(10) 0.09931(8) -0.15886(16) 0.0337(3) Uani 1 1 d . . . . .
H7A H 0.584897 0.061857 -0.218574 0.040 Uiso 1 1 calc R U . . .
H7B H 0.589832 0.147762 -0.144168 0.040 Uiso 1 1 calc R U . . .
C6 C 0.68858(14) 0.14962(9) -0.37352(16) 0.0404(4) Uani 1 1 d . . . . .
H6A H 0.641462 0.112851 -0.429530 0.049 Uiso 1 1 calc R U . . .
H6B H 0.750447 0.151466 -0.422142 0.049 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
N2 C2 1.3805(16) . ?
N2 H2A 0.88(2) . ?
N2 H2B 0.883(17) . ?
N1 C5 1.149(2) . ?
F1 C3 1.3629(14) . ?
C1 C2 1.4148(14) 2_655 ?
C1 C2 1.4148(14) . ?
C1 C5 1.433(2) . ?
C2 C3 1.3911(18) . ?
C4 C3 1.3751(16) . ?
C4 C3 1.3751(16) 2_655 ?
C4 H4 0.9500 . ?
O2 C8 1.4227(16) . ?
O2 C9 1.4286(16) . ?
O1 C7 1.4129(17) . ?
O1 C6 1.4238(18) . ?
O3 C11 1.4173(18) . ?
O3 C10 1.4210(16) . ?
C8 C7 1.500(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C9 1.491(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 C6 1.504(2) 7_655 ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 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 N2 H2A 112.0(12) . . ?
C2 N2 H2B 114.6(11) . . ?
H2A N2 H2B 108.1(15) . . ?
C2 C1 C2 123.03(15) 2_655 . ?
C2 C1 C5 118.49(8) 2_655 . ?
C2 C1 C5 118.49(8) . . ?
N2 C2 C3 121.36(11) . . ?
N2 C2 C1 122.60(12) . . ?
C3 C2 C1 115.95(11) . . ?
C3 C4 C3 118.76(17) . 2_655 ?
C3 C4 H4 120.6 . . ?
C3 C4 H4 120.6 2_655 . ?
N1 C5 C1 180.0 . . ?
F1 C3 C4 118.67(12) . . ?
F1 C3 C2 118.30(11) . . ?
C4 C3 C2 123.03(12) . . ?
C8 O2 C9 111.16(10) . . ?
C7 O1 C6 114.33(12) . . ?
C11 O3 C10 111.81(11) . . ?
O2 C8 C7 109.54(11) . . ?
O2 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
O2 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
O3 C10 C9 108.56(11) . . ?
O3 C10 H10A 110.0 . . ?
C9 C10 H10A 110.0 . . ?
O3 C10 H10B 110.0 . . ?
C9 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
O2 C9 C10 108.98(10) . . ?
O2 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 . . ?
O2 C9 H9B 109.9 . . ?
C10 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
O3 C11 C6 109.24(13) . 7_655 ?
O3 C11 H11A 109.8 . . ?
C6 C11 H11A 109.8 7_655 . ?
O3 C11 H11B 109.8 . . ?
C6 C11 H11B 109.8 7_655 . ?
H11A C11 H11B 108.3 . . ?
O1 C7 C8 108.98(11) . . ?
O1 C7 H7A 109.9 . . ?
C8 C7 H7A 109.9 . . ?
O1 C7 H7B 109.9 . . ?
C8 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
O1 C6 C11 114.91(13) . 7_655 ?
O1 C6 H6A 108.5 . . ?
C11 C6 H6A 108.5 7_655 . ?
O1 C6 H6B 108.5 . . ?
C11 C6 H6B 108.5 7_655 . ?
H6A C6 H6B 107.5 . . ?

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
C2 C1 C2 N2 -178.80(13) 2_655 . . . ?
C5 C1 C2 N2 1.20(13) . . . . ?
C2 C1 C2 C3 -2.26(8) 2_655 . . . ?
C5 C1 C2 C3 177.74(8) . . . . ?
C3 C4 C3 F1 178.08(13) 2_655 . . . ?
C3 C4 C3 C2 -2.55(9) 2_655 . . . ?
N2 C2 C3 F1 0.72(19) . . . . ?
C1 C2 C3 F1 -175.86(9) . . . . ?
N2 C2 C3 C4 -178.65(10) . . . . ?
C1 C2 C3 C4 4.77(17) . . . . ?
C9 O2 C8 C7 179.37(11) . . . . ?
C11 O3 C10 C9 -178.37(11) . . . . ?
C8 O2 C9 C10 166.09(11) . . . . ?
O3 C10 C9 O2 61.98(14) . . . . ?
C10 O3 C11 C6 169.51(13) . . . 7_655 ?
C6 O1 C7 C8 176.42(11) . . . . ?
O2 C8 C7 O1 64.79(14) . . . . ?
C7 O1 C6 C11 69.08(17) . . . 7_655 ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.184
_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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2075034'
loop_
_audit_author_name
_audit_author_address
'Boris Zakharov'
;Boreskov Institute of Catalysis SB RAS
Russia
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_ATOM007_I                   
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: Low-resolution structure model. Crystal does not diffract beyond 1.3 A
;
_vrf_PLAT082_I                   
;
PROBLEM: High R1 Value ..................................       0.41 Report
RESPONSE: Low-resolution structure model. Crystal does not diffract beyond 1.3 A
;
_vrf_PLAT084_I                   
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.77 Report
RESPONSE: Low-resolution structure model. Crystal does not diffract beyond 1.3 A
;
_vrf_PLAT934_I                   
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..         14 Check
RESPONSE: Low-resolution structure model. Crystal does not diffract beyond 1.3 A
;
_vrf_DIFMN02_I                   
;
PROBLEM: The minimum difference density is < -0.1*ZMAX*1.00
RESPONSE: Isotropic refiniment. Low-resolution structure model. Crystal does not diffract beyond 1.3 A
;
_vrf_PLAT026_I                   
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        36% Check
RESPONSE: Weak diffraction. Crystal does not diffract beyond 1.3 A
;
_vrf_PLAT029_I                   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.941 Why?
RESPONSE: CuKa radiation. Some reflections are not accessible due to diffractometer geometry restrictions.
;
_vrf_PLAT043_I                   
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..      32.25 Check
RESPONSE: H-atoms are not determined
;
_vrf_PLAT097_I                   
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.77 eA-3
RESPONSE: Isotropic refiniment. Low-resolution structure model. Crystal does not diffract beyond 1.3 A
;
_vrf_PLAT098_I                   
;
PROBLEM: Large Reported Min.  (Negative) Residual Density      -0.92 eA-3
RESPONSE: Isotropic refiniment. Low-resolution structure model. Crystal does not diffract beyond 1.3 A
;
_vrf_PLAT149_I                   
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.06 Degree
RESPONSE: Weak diffraction. Crystal does not diffract beyond 1.3 A
;
_vrf_PLAT201_I                   
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          9 Report
RESPONSE: Weak diffraction. Crystal does not diffract beyond 1.3 A
;
_vrf_PLAT340_I                   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.026 Ang.
RESPONSE: Isotropic refiniment. Low-resolution structure model. Crystal does not diffract beyond 1.3 A
;
_vrf_PLAT911_I                   
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        158 Report
RESPONSE: CuKa radiation. Some reflections are not accessible due to diffractometer geometry restrictions.
;
_vrf_PLAT930_I                   
;
PROBLEM: FCF-based   Twin Law ( 1-1-1)[ 2-1-1] Est.d BASF       0.54 Check
RESPONSE: Taking into account the proposed twinning does not improve the model.
;
# Added during the CSD deposition process: Friday 02 April 2021 11:21 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2,4-diamino-3,5,6-trifluorobenzonitrile--18-crown-6 ether (2:1)
;
_chemical_name_common            
;
2,4-diamino-3,5,6-trifluorobenzonitrile--18-crown-6 ether (2:1)
;
_chemical_melting_point          400
_chemical_formula_moiety         '1(C12 H24 O6), 2(C7 H4 F3 N3)'
_chemical_formula_sum            'C26 H32 F6 N6 O6'
_chemical_formula_weight         638.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.295(5)
_cell_length_b                   14.527(5)
_cell_length_c                   11.722(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.33(6)
_cell_angle_gamma                90
_cell_volume                     1493.6(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    469
_cell_measurement_theta_min      5.0280
_cell_measurement_theta_max      42.9810

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.63430
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7158
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.026
_diffrn_reflns_theta_max         67.789
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.941
_reflns_number_total             2541
_reflns_number_gt                923
_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       
'CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)'
_computing_cell_refinement       
'CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)'
_computing_data_reduction        
'CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2541
_refine_ls_number_parameters     77
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.4752
_refine_ls_R_factor_gt           0.4081
_refine_ls_wR_factor_ref         0.7727
_refine_ls_wR_factor_gt          0.7372
_refine_ls_goodness_of_fit_ref   2.392
_refine_ls_restrained_S_all      2.388
_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
C1 C 0.1083(12) 0.6002(7) 0.5066(9) 0.119(6) Uiso 1 1 d G . . . .
C2 C 0.0677(10) 0.6284(6) 0.6051(12) 0.111(6) Uiso 1 1 d G . . . .
C3 C 0.1439(13) 0.5930(7) 0.7194(10) 0.113(6) Uiso 1 1 d G . . . .
C4 C 0.2606(12) 0.5294(7) 0.7351(9) 0.138(8) Uiso 1 1 d G . . . .
C5 C 0.3012(10) 0.5012(6) 0.6366(13) 0.103(6) Uiso 1 1 d G . . . .
C6 C 0.2250(13) 0.5366(7) 0.5223(10) 0.123(7) Uiso 1 1 d G . . . .
C7 C 0.028(2) 0.6386(13) 0.397(2) 0.135(7) Uiso 1 1 d . . . . .
F1 F 0.1052(15) 0.6199(8) 0.8119(12) 0.155(5) Uiso 1 1 d . . . . .
F2 F 0.4103(18) 0.4414(11) 0.6496(17) 0.196(7) Uiso 1 1 d . . . . .
F3 F 0.2617(16) 0.5105(8) 0.4254(15) 0.154(5) Uiso 1 1 d . . . . .
N1 N -0.043(3) 0.6712(14) 0.294(3) 0.196(10) Uiso 1 1 d . . . . .
N2 N -0.044(2) 0.6892(11) 0.5949(19) 0.150(7) Uiso 1 1 d . . . . .
N3 N 0.3389(12) 0.4934(6) 0.8471(10) 0.062(3) Uiso 1 1 d . . . . .
O1 O 0.741(3) 0.4817(16) 0.915(2) 0.191(9) Uiso 1 1 d . . . . .
O2 O 0.568(3) 0.3302(15) 0.917(2) 0.177(8) Uiso 1 1 d . . . . .
O3 O 0.407(3) 0.3243(16) 1.078(2) 0.193(9) Uiso 1 1 d . . . . .
C8 C 0.742(4) 0.405(3) 0.860(3) 0.182(12) Uiso 1 1 d . . . . .
C9 C 0.701(4) 0.323(2) 0.919(3) 0.173(11) Uiso 1 1 d . . . . .
C10 C 0.553(4) 0.273(2) 0.987(3) 0.174(11) Uiso 1 1 d . . . . .
C11 C 0.434(3) 0.265(2) 1.011(3) 0.150(9) Uiso 1 1 d . . . . .
C12 C 0.291(3) 0.3504(19) 1.064(2) 0.138(8) Uiso 1 1 d . . . . .
C13 C 0.243(3) 0.419(2) 1.140(3) 0.158(9) Uiso 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
C1 C7 1.37(3) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 N2 1.34(2) . ?
C2 C3 1.3900 . ?
C3 F1 1.310(14) . ?
C3 C4 1.3900 . ?
C4 N3 1.376(14) . ?
C4 C5 1.3900 . ?
C5 F2 1.31(2) . ?
C5 C6 1.3900 . ?
C6 F3 1.344(17) . ?
C7 N1 1.26(3) . ?
O1 C8 1.29(4) . ?
O1 C13 1.61(4) 3_667 ?
O2 C10 1.21(3) . ?
O2 C9 1.23(3) . ?
O3 C12 1.10(3) . ?
O3 C11 1.25(3) . ?
C8 C9 1.50(4) . ?
C9 C10 1.94(5) . ?
C10 C11 1.24(4) . ?
C12 C13 1.50(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
C7 C1 C2 116.2(14) . . ?
C7 C1 C6 123.8(14) . . ?
C2 C1 C6 120.0 . . ?
N2 C2 C3 117.6(13) . . ?
N2 C2 C1 122.4(13) . . ?
C3 C2 C1 120.0 . . ?
F1 C3 C2 119.7(12) . . ?
F1 C3 C4 120.3(12) . . ?
C2 C3 C4 120.0 . . ?
N3 C4 C5 118.5(10) . . ?
N3 C4 C3 121.5(10) . . ?
C5 C4 C3 120.0 . . ?
F2 C5 C4 120.9(13) . . ?
F2 C5 C6 119.1(13) . . ?
C4 C5 C6 120.0 . . ?
F3 C6 C5 121.3(12) . . ?
F3 C6 C1 118.7(12) . . ?
C5 C6 C1 120.0 . . ?
N1 C7 C1 177(3) . . ?
C8 O1 C13 124(3) . 3_667 ?
C10 O2 C9 105(3) . . ?
C12 O3 C11 122(3) . . ?
O1 C8 C9 114(3) . . ?
O2 C9 C8 109(3) . . ?
O2 C9 C10 36.8(17) . . ?
C8 C9 C10 144(3) . . ?
O2 C10 C11 122(3) . . ?
O2 C10 C9 37.8(18) . . ?
C11 C10 C9 160(3) . . ?
C10 C11 O3 118(3) . . ?
O3 C12 C13 127(3) . . ?
C12 C13 O1 106(2) . 3_667 ?

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
C7 C1 C2 N2 0.3(4) . . . . ?
C6 C1 C2 N2 -179.9(3) . . . . ?
C7 C1 C2 C3 -179.8(3) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
N2 C2 C3 F1 -0.2(4) . . . . ?
C1 C2 C3 F1 180.0(3) . . . . ?
N2 C2 C3 C4 179.9(3) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
F1 C3 C4 N3 -0.3(4) . . . . ?
C2 C3 C4 N3 179.7(3) . . . . ?
F1 C3 C4 C5 -180.0(3) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
N3 C4 C5 F2 0.5(4) . . . . ?
C3 C4 C5 F2 -179.9(3) . . . . ?
N3 C4 C5 C6 -179.7(3) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
F2 C5 C6 F3 -0.1(4) . . . . ?
C4 C5 C6 F3 -180.0(3) . . . . ?
F2 C5 C6 C1 179.9(3) . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C7 C1 C6 F3 -0.2(4) . . . . ?
C2 C1 C6 F3 180.0(3) . . . . ?
C7 C1 C6 C5 179.8(3) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C13 O1 C8 C9 -171(2) 3_667 . . . ?
C10 O2 C9 C8 -166(3) . . . . ?
O1 C8 C9 O2 65(4) . . . . ?
O1 C8 C9 C10 50(6) . . . . ?
C9 O2 C10 C11 176(3) . . . . ?
O2 C10 C11 O3 -75(5) . . . . ?
C9 C10 C11 O3 -68(10) . . . . ?
C12 O3 C11 C10 142(4) . . . . ?
C11 O3 C12 C13 178(2) . . . . ?
O3 C12 C13 O1 89(4) . . . 3_667 ?

_refine_diff_density_max         1.773
_refine_diff_density_min         -0.916
_refine_diff_density_rms         0.416

####################################################################### 
# 
# 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-mal125a
_database_code_depnum_ccdc_archive 'CCDC 2076053'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2,4-diamino-3,5,6-trifluorobenzonitrile hydrate
;
_chemical_name_common            ?
_chemical_melting_point          394
_chemical_formula_moiety         'C7 H4 F3 N3, 0.5(H2  O)'
_chemical_formula_sum            'C7 H4 F3 N3 O0.50'
_chemical_formula_weight         195.13

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'
F F 0.0171 0.0103 '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      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+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   13.9801(16)
_cell_length_b                   15.5918(17)
_cell_length_c                   3.6651(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     798.90(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6548
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      27.12

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.156
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9103
_exptl_absorpt_correction_T_max  0.9703
_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            17134
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         2.613
_diffrn_reflns_theta_max         28.299
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1976
_reflns_number_gt                1609
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     1.000
_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    'SHELXT-2018/2 (Sheldrick, 2018)'
_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)+(0.0914P)²+0.3400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 614 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1976
_refine_ls_number_parameters     138
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1564
_refine_ls_wR_factor_gt          0.1384
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.004
_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 0.03185(16) 0.25303(14) 1.0048(8) 0.0593(7) Uani 1 1 d . . . . .
N1 N 0.3865(2) 0.1197(2) 0.4100(12) 0.0610(10) Uani 1 1 d . . . . .
C1 C 0.2714(2) 0.2363(2) 0.6355(10) 0.0384(7) Uani 1 1 d . . . . .
F2 F 0.25815(17) 0.46702(14) 0.7383(9) 0.0649(8) Uani 1 1 d . . . . .
C2 C 0.1809(2) 0.2132(2) 0.7640(10) 0.0411(7) Uani 1 1 d . . . . .
N2 N 0.1539(3) 0.12955(19) 0.7732(12) 0.0581(10) Uani 1 1 d D . . . .
H2A H 0.110(3) 0.121(3) 0.927(12) 0.070 Uiso 1 1 d D U . . .
H2B H 0.193(3) 0.094(3) 0.684(14) 0.070 Uiso 1 1 d D U . . .
F3 F 0.38291(17) 0.34653(18) 0.5032(10) 0.0723(8) Uani 1 1 d . . . . .
C3 C 0.1193(2) 0.2756(2) 0.8788(10) 0.0406(7) Uani 1 1 d . . . . .
N3 N 0.0800(2) 0.42317(19) 0.9966(11) 0.0505(8) Uani 1 1 d D . . . .
H3A H 0.0248(18) 0.409(3) 1.088(13) 0.061 Uiso 1 1 d D U . . .
H3B H 0.097(3) 0.4754(13) 0.955(15) 0.061 Uiso 1 1 d D U . . .
C4 C 0.1418(2) 0.3627(2) 0.8750(9) 0.0365(6) Uani 1 1 d . . . . .
C5 C 0.2330(2) 0.3835(2) 0.7447(10) 0.0411(7) Uani 1 1 d . . . . .
C6 C 0.2968(2) 0.3232(2) 0.6302(10) 0.0402(7) Uani 1 1 d . . . . .
C7 C 0.3367(2) 0.1721(2) 0.5102(12) 0.0451(7) Uani 1 1 d . . . . .
O1A O 0.007(2) 0.0221(14) 1.171(12) 0.118(7) Uiso 0.25 1 d . . P . .
O1B O -0.014(2) 0.003(2) 0.905(14) 0.137(9) Uiso 0.25 1 d . . P . .


_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(4) . ?
N1 C7 1.135(5) . ?
C1 C2 1.398(5) . ?
C1 C6 1.402(5) . ?
C1 C7 1.429(5) . ?
F2 C5 1.349(4) . ?
C2 N2 1.358(4) . ?
C2 C3 1.365(5) . ?
N2 H2A 0.848(14) . ?
N2 H2B 0.845(14) . ?
F3 C6 1.341(4) . ?
C3 C4 1.393(4) . ?
N3 C4 1.355(4) . ?
N3 H3A 0.868(14) . ?
N3 H3B 0.862(14) . ?
C4 C5 1.399(5) . ?
C5 C6 1.362(5) . ?
O1A O1B 0.95(3) 2 ?
O1A O1B 1.06(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 C1 C6 118.9(3) . . ?
C2 C1 C7 120.5(3) . . ?
C6 C1 C7 120.7(3) . . ?
N2 C2 C3 120.1(3) . . ?
N2 C2 C1 120.4(3) . . ?
C3 C2 C1 119.4(3) . . ?
C2 N2 H2A 112(4) . . ?
C2 N2 H2B 116(4) . . ?
H2A N2 H2B 129(5) . . ?
F1 C3 C2 119.3(3) . . ?
F1 C3 C4 117.4(3) . . ?
C2 C3 C4 123.3(3) . . ?
C4 N3 H3A 121(3) . . ?
C4 N3 H3B 115(3) . . ?
H3A N3 H3B 123(4) . . ?
N3 C4 C3 122.1(3) . . ?
N3 C4 C5 122.1(3) . . ?
C3 C4 C5 115.8(3) . . ?
F2 C5 C6 119.3(3) . . ?
F2 C5 C4 117.9(3) . . ?
C6 C5 C4 122.8(3) . . ?
F3 C6 C5 120.5(3) . . ?
F3 C6 C1 119.6(3) . . ?
C5 C6 C1 119.8(3) . . ?
N1 C7 C1 178.1(4) . . ?
O1B O1A O1B 138(2) 2 . ?
O1A O1B O1A 157(3) 2_554 . ?

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 N2 -179.9(4) . . . . ?
C7 C1 C2 N2 0.4(6) . . . . ?
C6 C1 C2 C3 0.4(5) . . . . ?
C7 C1 C2 C3 -179.3(4) . . . . ?
N2 C2 C3 F1 0.7(6) . . . . ?
C1 C2 C3 F1 -179.6(4) . . . . ?
N2 C2 C3 C4 -179.6(4) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
F1 C3 C4 N3 0.9(5) . . . . ?
C2 C3 C4 N3 -178.8(4) . . . . ?
F1 C3 C4 C5 179.7(3) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
N3 C4 C5 F2 -0.9(6) . . . . ?
C3 C4 C5 F2 -179.6(3) . . . . ?
N3 C4 C5 C6 178.3(4) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
F2 C5 C6 F3 -1.7(6) . . . . ?
C4 C5 C6 F3 179.1(4) . . . . ?
F2 C5 C6 C1 -180.0(4) . . . . ?
C4 C5 C6 C1 0.9(6) . . . . ?
C2 C1 C6 F3 -179.1(4) . . . . ?
C7 C1 C6 F3 0.6(6) . . . . ?
C2 C1 C6 C5 -0.8(6) . . . . ?
C7 C1 C6 C5 178.8(4) . . . . ?
O1B O1A O1B O1A -81(11) 2 . . 2_554 ?

_refine_diff_density_max         0.252
_refine_diff_density_min         -0.205
_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_Ecr-c_5mal
_database_code_depnum_ccdc_archive 'CCDC 2076052'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2,6-diamino-4-chloro-3-fluorobenzonitrile and 18-crown-6, 1:1 co-crystal
;
_chemical_name_common            ?
_chemical_melting_point          414
_chemical_formula_moiety         'C12 H24 O6, C7 H5 Cl F N3'
_chemical_formula_sum            'C19 H29 Cl F N3 O6'
_chemical_formula_weight         449.90

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/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'
'-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                   27.0089(13)
_cell_length_b                   10.1240(5)
_cell_length_c                   17.2092(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.123(2)
_cell_angle_gamma                90
_cell_volume                     4669.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    6073
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      22.21

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             1904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.209
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8001
_exptl_absorpt_correction_T_max  0.9118
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(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            26879
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_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         2.150
_diffrn_reflns_theta_max         25.113
_diffrn_reflns_theta_full        25.113
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4146
_reflns_number_gt                2649
_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-2018/2 (Sheldrick, 2018)'
_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)+(0.1748P)²+6.8591P] 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         4146
_refine_ls_number_parameters     294
_refine_ls_number_restraints     196
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0815
_refine_ls_wR_factor_ref         0.2998
_refine_ls_wR_factor_gt          0.2553
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.956
_refine_ls_shift/su_max          0.001
_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
Cl1 Cl 0.58059(9) 0.00826(12) 0.61008(8) 0.1560(9) Uani 1 1 d . . . A 1
F1 F 0.58189(14) 0.1784(3) 0.74335(15) 0.1030(13) Uani 0.813(5) 1 d . . P A 1
C1 C 0.63563(11) 0.4232(3) 0.62716(16) 0.0539(7) Uani 1 1 d . . . A 1
N1 N 0.6599(2) 0.6679(5) 0.6345(2) 0.1278(18) Uani 1 1 d . . . A 1
N2 N 0.61641(15) 0.4352(3) 0.76063(17) 0.0808(10) Uani 1 1 d D . . A 1
H2A H 0.6059(16) 0.393(4) 0.7983(18) 0.097 Uiso 1 1 d D U . B 1
H2B H 0.6294(15) 0.513(2) 0.768(3) 0.097 Uiso 1 1 d D U . C 1
C2 C 0.61832(12) 0.3662(3) 0.69344(16) 0.0550(8) Uani 1 1 d . . . A 1
N3 N 0.65470(15) 0.4081(4) 0.49363(19) 0.0882(10) Uani 1 1 d D . . A 1
H3A H 0.6538(18) 0.371(4) 0.4487(14) 0.106 Uiso 1 1 d D U . D 1
H3B H 0.6662(18) 0.487(2) 0.492(3) 0.106 Uiso 1 1 d D U . E 1
C3 C 0.60140(15) 0.2370(4) 0.68502(19) 0.0702(9) Uani 1 1 d . . . A 1
C4 C 0.60261(16) 0.1689(3) 0.6167(2) 0.0757(10) Uani 1 1 d . . . A 1
C5 C 0.62018(15) 0.2245(4) 0.5533(2) 0.0715(10) Uani 1 1 d . . . A 1
H5 H 0.621130 0.175185 0.507892 0.086 Uiso 1 1 calc R U . A 1
C6 C 0.63650(11) 0.3533(3) 0.55632(17) 0.0580(8) Uani 1 1 d . . . A 1
C7 C 0.65015(16) 0.5586(4) 0.63153(19) 0.0787(11) Uani 1 1 d . . . A 1
F1A F 0.6182(6) 0.1411(18) 0.5023(10) 0.120 Uiso 0.187(5) 1 d . U P A 2
O1 O 0.6101(2) 0.2664(5) 0.9086(2) 0.1175(16) Uani 0.870(6) 1 d . . P F 1
O2 O 0.70774(16) 0.3560(4) 0.9160(2) 0.1049(13) Uani 0.870(6) 1 d . . P F 1
O3 O 0.71994(15) 0.6187(5) 0.8497(2) 0.1062(13) Uani 0.870(6) 1 d . . P F 1
O4 O 0.6482(3) 0.8177(4) 0.8553(3) 0.1353(19) Uani 0.870(6) 1 d . . P F 1
O5 O 0.5527(2) 0.7127(7) 0.8406(3) 0.150(2) Uani 0.870(6) 1 d . . P F 1
O6 O 0.53607(17) 0.4680(8) 0.9128(3) 0.141(2) Uani 0.870(6) 1 d . . P F 1
C8 C 0.6509(3) 0.1912(6) 0.9418(3) 0.124(2) Uani 0.870(6) 1 d . . P F 1
H8A H 0.643434 0.097836 0.935361 0.148 Uiso 0.870(6) 1 calc R U P F 1
H8B H 0.657827 0.210010 0.997316 0.148 Uiso 0.870(6) 1 calc R U P F 1
C9 C 0.6950(3) 0.2258(6) 0.9016(4) 0.122(2) Uani 0.870(6) 1 d . . P F 1
H9A H 0.722850 0.169298 0.920638 0.146 Uiso 0.870(6) 1 calc R U P F 1
H9B H 0.687138 0.211726 0.845705 0.146 Uiso 0.870(6) 1 calc R U P F 1
C10 C 0.7462(3) 0.4007(9) 0.8704(5) 0.136(3) Uani 0.870(6) 1 d . . P F 1
H10A H 0.776323 0.349754 0.885060 0.164 Uiso 0.870(6) 1 calc R U P F 1
H10B H 0.735386 0.384934 0.815337 0.164 Uiso 0.870(6) 1 calc R U P F 1
C11 C 0.7571(2) 0.5390(11) 0.8822(5) 0.145(3) Uani 0.870(6) 1 d . . P F 1
H11A H 0.763205 0.556643 0.937988 0.174 Uiso 0.870(6) 1 calc R U P F 1
H11B H 0.787444 0.559886 0.859854 0.174 Uiso 0.870(6) 1 calc R U P F 1
C12 C 0.7300(3) 0.7555(9) 0.8607(5) 0.143(3) Uani 0.870(6) 1 d . . P F 1
H12A H 0.761036 0.777350 0.840932 0.172 Uiso 0.870(6) 1 calc R U P F 1
H12B H 0.733605 0.775886 0.916222 0.172 Uiso 0.870(6) 1 calc R U P F 1
C13 C 0.6892(5) 0.8352(8) 0.8197(4) 0.156(3) Uani 0.870(6) 1 d . . P F 1
H13A H 0.698518 0.927835 0.821125 0.187 Uiso 0.870(6) 1 calc R U P F 1
H13B H 0.682702 0.807990 0.765344 0.187 Uiso 0.870(6) 1 calc R U P F 1
C14 C 0.6079(5) 0.8629(8) 0.8032(4) 0.170(4) Uani 0.870(6) 1 d . . P F 1
H14A H 0.604755 0.811256 0.755386 0.204 Uiso 0.870(6) 1 calc R U P F 1
H14B H 0.612710 0.954780 0.790038 0.204 Uiso 0.870(6) 1 calc R U P F 1
C15 C 0.5642(5) 0.8485(9) 0.8417(6) 0.174(4) Uani 0.870(6) 1 d . . P F 1
H15A H 0.536744 0.898598 0.814478 0.208 Uiso 0.870(6) 1 calc R U P F 1
H15B H 0.570504 0.880264 0.895222 0.208 Uiso 0.870(6) 1 calc R U P F 1
C16 C 0.5145(3) 0.6886(13) 0.8832(6) 0.180(4) Uani 0.870(6) 1 d . . P F 1
H16A H 0.486266 0.744728 0.865359 0.216 Uiso 0.870(6) 1 calc R U P F 1
H16B H 0.524911 0.707333 0.938115 0.216 Uiso 0.870(6) 1 calc R U P F 1
C17 C 0.5001(3) 0.5460(13) 0.8728(5) 0.168(3) Uani 0.870(6) 1 d . . P F 1
H17A H 0.468392 0.530855 0.892373 0.201 Uiso 0.870(6) 1 calc R U P F 1
H17B H 0.496326 0.523398 0.817639 0.201 Uiso 0.870(6) 1 calc R U P F 1
C18 C 0.5256(3) 0.3277(12) 0.9036(5) 0.163(3) Uani 0.870(6) 1 d . . P F 1
H18A H 0.494793 0.306865 0.924557 0.195 Uiso 0.870(6) 1 calc R U P F 1
H18B H 0.521469 0.304810 0.848446 0.195 Uiso 0.870(6) 1 calc R U P F 1
C19 C 0.5676(3) 0.2495(9) 0.9458(4) 0.142(3) Uani 0.870(6) 1 d . . P F 1
H19A H 0.574106 0.279033 0.999756 0.171 Uiso 0.870(6) 1 calc R U P F 1
H19B H 0.558587 0.156721 0.945903 0.171 Uiso 0.870(6) 1 calc R U P F 1
O27Q O 0.6381(7) 0.2356(13) 0.8994(12) 0.120 Uiso 0.130(6) 1 d G U P F 2
O23Q O 0.7203(5) 0.4118(19) 0.9015(12) 0.120 Uiso 0.130(6) 1 d G U P F 2
O12Q O 0.7077(6) 0.6763(19) 0.8371(12) 0.120 Uiso 0.130(6) 1 d G U P F 2
O8Q O 0.6176(7) 0.8213(13) 0.8509(13) 0.120 Uiso 0.130(6) 1 d G U P F 2
O7Q O 0.5353(5) 0.6451(18) 0.8487(12) 0.120 Uiso 0.130(6) 1 d G U P F 2
O13Q O 0.5480(6) 0.3807(17) 0.9131(12) 0.120 Uiso 0.130(6) 1 d G U P F 2
C1Q C 0.6869(8) 0.2055(16) 0.9355(13) 0.126 Uiso 0.130(6) 1 d G U P F 2
H1Q1 H 0.692123 0.110684 0.935149 0.151 Uiso 0.130(6) 1 calc R U P F 2
H1Q2 H 0.690827 0.235137 0.989480 0.151 Uiso 0.130(6) 1 calc R U P F 2
C2Q C 0.7242(7) 0.2724(19) 0.8921(14) 0.121 Uiso 0.130(6) 1 d G U P F 2
H2Q1 H 0.757584 0.243207 0.912114 0.145 Uiso 0.130(6) 1 calc R U P F 2
H2Q2 H 0.718134 0.249766 0.836934 0.145 Uiso 0.130(6) 1 calc R U P F 2
C3Q C 0.7561(5) 0.481(2) 0.8634(14) 0.122 Uiso 0.130(6) 1 d G U P F 2
H3Q1 H 0.750469 0.463857 0.807589 0.146 Uiso 0.130(6) 1 calc R U P F 2
H3Q2 H 0.789358 0.450621 0.882984 0.146 Uiso 0.130(6) 1 calc R U P F 2
C4Q C 0.7525(5) 0.626(2) 0.8775(15) 0.128 Uiso 0.130(6) 1 d G U P F 2
H4Q1 H 0.753251 0.642066 0.933178 0.153 Uiso 0.130(6) 1 calc R U P F 2
H4Q2 H 0.780791 0.670283 0.859688 0.153 Uiso 0.130(6) 1 calc R U P F 2
C5Q C 0.7046(7) 0.8162(18) 0.8427(15) 0.122 Uiso 0.130(6) 1 d G U P F 2
H5Q1 H 0.730830 0.856733 0.817195 0.147 Uiso 0.130(6) 1 calc R U P F 2
H5Q2 H 0.709073 0.842502 0.897360 0.147 Uiso 0.130(6) 1 calc R U P F 2
C6Q C 0.6549(8) 0.8618(16) 0.8046(14) 0.128 Uiso 0.130(6) 1 d G U P F 2
H6Q1 H 0.654715 0.957291 0.799840 0.153 Uiso 0.130(6) 1 calc R U P F 2
H6Q2 H 0.648146 0.824248 0.752547 0.153 Uiso 0.130(6) 1 calc R U P F 2
C7Q C 0.5688(8) 0.8515(16) 0.8147(14) 0.126 Uiso 0.130(6) 1 d G U P F 2
H7Q1 H 0.564862 0.821793 0.760732 0.151 Uiso 0.130(6) 1 calc R U P F 2
H7Q2 H 0.563567 0.946247 0.815063 0.151 Uiso 0.130(6) 1 calc R U P F 2
C8Q C 0.5315(7) 0.7845(18) 0.8582(14) 0.121 Uiso 0.130(6) 1 d G U P F 2
H8Q1 H 0.537556 0.807164 0.913278 0.145 Uiso 0.130(6) 1 calc R U P F 2
H8Q2 H 0.498106 0.813723 0.838098 0.145 Uiso 0.130(6) 1 calc R U P F 2
C9Q C 0.4996(5) 0.576(2) 0.8868(14) 0.122 Uiso 0.130(6) 1 d G U P F 2
H9Q1 H 0.466331 0.606309 0.867229 0.146 Uiso 0.130(6) 1 calc R U P F 2
H9Q2 H 0.505221 0.593073 0.942623 0.146 Uiso 0.130(6) 1 calc R U P F 2
C10Q C 0.5032(5) 0.431(2) 0.8727(14) 0.128 Uiso 0.130(6) 1 d G U P F 2
H10C H 0.474899 0.386647 0.890524 0.153 Uiso 0.130(6) 1 calc R U P F 2
H10D H 0.502439 0.414865 0.817034 0.153 Uiso 0.130(6) 1 calc R U P F 2
C11Q C 0.5511(7) 0.2407(17) 0.9075(14) 0.122 Uiso 0.130(6) 1 d G U P F 2
H11C H 0.546617 0.214428 0.852852 0.147 Uiso 0.130(6) 1 calc R U P F 2
H11D H 0.524859 0.200197 0.933017 0.147 Uiso 0.130(6) 1 calc R U P F 2
C12Q C 0.6008(8) 0.1951(15) 0.9456(13) 0.128 Uiso 0.130(6) 1 d G U P F 2
H12C H 0.607544 0.232682 0.997665 0.153 Uiso 0.130(6) 1 calc R U P F 2
H12D H 0.600975 0.099638 0.950372 0.153 Uiso 0.130(6) 1 calc R U P F 2


_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
Cl1 C4 1.731(4) . ?
F1 C3 1.330(4) . ?
C1 C2 1.409(4) . ?
C1 C7 1.425(5) . ?
C1 C6 1.413(4) . ?
N1 C7 1.136(5) . ?
N2 C2 1.357(4) . ?
N2 H2A 0.857(10) . ?
N2 H2B 0.860(10) . ?
C2 C3 1.388(5) . ?
N3 C6 1.358(4) . ?
N3 H3A 0.858(10) . ?
N3 H3B 0.857(10) . ?
C3 C4 1.367(5) . ?
C4 C5 1.364(5) . ?
C5 C6 1.375(5) . ?
C5 H5 0.9300 . ?
O1 C8 1.401(8) . ?
O1 C19 1.393(8) . ?
O2 C9 1.377(8) . ?
O2 C10 1.448(8) . ?
O3 C12 1.419(9) . ?
O3 C11 1.355(9) . ?
O4 C14 1.398(11) . ?
O4 C13 1.343(10) . ?
O5 C16 1.360(11) . ?
O5 C15 1.410(12) . ?
O6 C17 1.369(11) . ?
O6 C18 1.453(11) . ?
C8 C9 1.491(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.440(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.473(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.431(14) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.501(14) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.495(12) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
O27Q C1Q 1.4183 . ?
O27Q C12Q 1.4196 . ?
O23Q C3Q 1.4193 . ?
O23Q C2Q 1.4259 . ?
O12Q C4Q 1.4155 . ?
O12Q C5Q 1.4232 . ?
O8Q C7Q 1.4183 . ?
O8Q C6Q 1.4196 . ?
O7Q C9Q 1.4194 . ?
O7Q C8Q 1.4259 . ?
O13Q C10Q 1.4155 . ?
O13Q C11Q 1.4232 . ?
C1Q C2Q 1.4905 . ?
C1Q H1Q1 0.9700 . ?
C1Q H1Q2 0.9700 . ?
C2Q H2Q1 0.9700 . ?
C2Q H2Q2 0.9700 . ?
C3Q C4Q 1.4870 . ?
C3Q H3Q1 0.9700 . ?
C3Q H3Q2 0.9700 . ?
C4Q H4Q1 0.9700 . ?
C4Q H4Q2 0.9700 . ?
C5Q C6Q 1.4927 . ?
C5Q H5Q1 0.9700 . ?
C5Q H5Q2 0.9700 . ?
C6Q H6Q1 0.9700 . ?
C6Q H6Q2 0.9700 . ?
C7Q C8Q 1.4905 . ?
C7Q H7Q1 0.9700 . ?
C7Q H7Q2 0.9700 . ?
C8Q H8Q1 0.9700 . ?
C8Q H8Q2 0.9700 . ?
C9Q C10Q 1.4870 . ?
C9Q H9Q1 0.9700 . ?
C9Q H9Q2 0.9700 . ?
C10Q H10C 0.9700 . ?
C10Q H10D 0.9700 . ?
C11Q C12Q 1.4927 . ?
C11Q H11C 0.9700 . ?
C11Q H11D 0.9700 . ?
C12Q H12C 0.9700 . ?
C12Q H12D 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 C1 C7 117.9(3) . . ?
C2 C1 C6 122.4(3) . . ?
C7 C1 C6 119.6(3) . . ?
C2 N2 H2A 116(3) . . ?
C2 N2 H2B 122(3) . . ?
H2A N2 H2B 121(4) . . ?
N2 C2 C3 121.8(3) . . ?
N2 C2 C1 122.0(3) . . ?
C3 C2 C1 116.1(3) . . ?
C6 N3 H3A 124(3) . . ?
C6 N3 H3B 125(3) . . ?
H3A N3 H3B 111(5) . . ?
F1 C3 C4 118.6(3) . . ?
F1 C3 C2 119.9(3) . . ?
C4 C3 C2 121.5(3) . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 Cl1 119.1(3) . . ?
C3 C4 Cl1 119.1(3) . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
N3 C6 C5 120.2(3) . . ?
N3 C6 C1 121.8(3) . . ?
C5 C6 C1 118.0(3) . . ?
N1 C7 C1 177.4(5) . . ?
C8 O1 C19 113.4(5) . . ?
C9 O2 C10 112.5(5) . . ?
C12 O3 C11 114.0(6) . . ?
C14 O4 C13 106.5(7) . . ?
C16 O5 C15 110.3(8) . . ?
C17 O6 C18 113.1(7) . . ?
O1 C8 C9 108.5(4) . . ?
O1 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
O1 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
O2 C9 C8 109.8(5) . . ?
O2 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
O2 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C11 C10 O2 112.1(5) . . ?
C11 C10 H10A 109.2 . . ?
O2 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
O2 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
O3 C11 C10 113.1(6) . . ?
O3 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
O3 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
O3 C12 C13 110.6(6) . . ?
O3 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
O4 C13 C12 108.6(5) . . ?
O4 C13 H13A 110.0 . . ?
C12 C13 H13A 110.0 . . ?
O4 C13 H13B 110.0 . . ?
C12 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
O4 C14 C15 106.9(6) . . ?
O4 C14 H14A 110.3 . . ?
C15 C14 H14A 110.3 . . ?
O4 C14 H14B 110.3 . . ?
C15 C14 H14B 110.3 . . ?
H14A C14 H14B 108.6 . . ?
C14 C15 O5 106.6(7) . . ?
C14 C15 H15A 110.4 . . ?
O5 C15 H15A 110.4 . . ?
C14 C15 H15B 110.4 . . ?
O5 C15 H15B 110.4 . . ?
H15A C15 H15B 108.6 . . ?
O5 C16 C17 108.1(7) . . ?
O5 C16 H16A 110.1 . . ?
C17 C16 H16A 110.1 . . ?
O5 C16 H16B 110.1 . . ?
C17 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?
O6 C17 C16 109.7(7) . . ?
O6 C17 H17A 109.7 . . ?
C16 C17 H17A 109.7 . . ?
O6 C17 H17B 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C19 C18 O6 109.8(6) . . ?
C19 C18 H18A 109.7 . . ?
O6 C18 H18A 109.7 . . ?
C19 C18 H18B 109.7 . . ?
O6 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
O1 C19 C18 109.2(5) . . ?
O1 C19 H19A 109.8 . . ?
C18 C19 H19A 109.8 . . ?
O1 C19 H19B 109.8 . . ?
C18 C19 H19B 109.8 . . ?
H19A C19 H19B 108.3 . . ?
C1Q O27Q C12Q 112.2 . . ?
C3Q O23Q C2Q 112.0 . . ?
C4Q O12Q C5Q 112.3 . . ?
C7Q O8Q C6Q 112.2 . . ?
C9Q O7Q C8Q 112.0 . . ?
C10Q O13Q C11Q 112.3 . . ?
O27Q C1Q C2Q 109.4 . . ?
O27Q C1Q H1Q1 109.8 . . ?
C2Q C1Q H1Q1 109.8 . . ?
O27Q C1Q H1Q2 109.8 . . ?
C2Q C1Q H1Q2 109.8 . . ?
H1Q1 C1Q H1Q2 108.2 . . ?
O23Q C2Q C1Q 109.2 . . ?
O23Q C2Q H2Q1 109.8 . . ?
C1Q C2Q H2Q1 109.8 . . ?
O23Q C2Q H2Q2 109.8 . . ?
C1Q C2Q H2Q2 109.8 . . ?
H2Q1 C2Q H2Q2 108.3 . . ?
O23Q C3Q C4Q 110.4 . . ?
O23Q C3Q H3Q1 109.6 . . ?
C4Q C3Q H3Q1 109.6 . . ?
O23Q C3Q H3Q2 109.6 . . ?
C4Q C3Q H3Q2 109.6 . . ?
H3Q1 C3Q H3Q2 108.1 . . ?
O12Q C4Q C3Q 110.2 . . ?
O12Q C4Q H4Q1 109.6 . . ?
C3Q C4Q H4Q1 109.6 . . ?
O12Q C4Q H4Q2 109.6 . . ?
C3Q C4Q H4Q2 109.6 . . ?
H4Q1 C4Q H4Q2 108.1 . . ?
O12Q C5Q C6Q 109.5 . . ?
O12Q C5Q H5Q1 109.8 . . ?
C6Q C5Q H5Q1 109.8 . . ?
O12Q C5Q H5Q2 109.8 . . ?
C6Q C5Q H5Q2 109.8 . . ?
H5Q1 C5Q H5Q2 108.2 . . ?
O8Q C6Q C5Q 109.1 . . ?
O8Q C6Q H6Q1 109.9 . . ?
C5Q C6Q H6Q1 109.9 . . ?
O8Q C6Q H6Q2 109.9 . . ?
C5Q C6Q H6Q2 109.9 . . ?
H6Q1 C6Q H6Q2 108.3 . . ?
O8Q C7Q C8Q 109.4 . . ?
O8Q C7Q H7Q1 109.8 . . ?
C8Q C7Q H7Q1 109.8 . . ?
O8Q C7Q H7Q2 109.8 . . ?
C8Q C7Q H7Q2 109.8 . . ?
H7Q1 C7Q H7Q2 108.2 . . ?
O7Q C8Q C7Q 109.2 . . ?
O7Q C8Q H8Q1 109.8 . . ?
C7Q C8Q H8Q1 109.8 . . ?
O7Q C8Q H8Q2 109.8 . . ?
C7Q C8Q H8Q2 109.8 . . ?
H8Q1 C8Q H8Q2 108.3 . . ?
O7Q C9Q C10Q 110.4 . . ?
O7Q C9Q H9Q1 109.6 . . ?
C10Q C9Q H9Q1 109.6 . . ?
O7Q C9Q H9Q2 109.6 . . ?
C10Q C9Q H9Q2 109.6 . . ?
H9Q1 C9Q H9Q2 108.1 . . ?
O13Q C10Q C9Q 110.2 . . ?
O13Q C10Q H10C 109.6 . . ?
C9Q C10Q H10C 109.6 . . ?
O13Q C10Q H10D 109.6 . . ?
C9Q C10Q H10D 109.6 . . ?
H10C C10Q H10D 108.1 . . ?
O13Q C11Q C12Q 109.5 . . ?
O13Q C11Q H11C 109.8 . . ?
C12Q C11Q H11C 109.8 . . ?
O13Q C11Q H11D 109.8 . . ?
C12Q C11Q H11D 109.8 . . ?
H11C C11Q H11D 108.2 . . ?
O27Q C12Q C11Q 109.1 . . ?
O27Q C12Q H12C 109.9 . . ?
C11Q C12Q H12C 109.9 . . ?
O27Q C12Q H12D 109.9 . . ?
C11Q C12Q H12D 109.9 . . ?
H12C C12Q H12D 108.3 . . ?

_refine_diff_density_max         0.445
_refine_diff_density_min         -0.271
_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_B-B_Mal
_database_code_depnum_ccdc_archive 'CCDC 2076054'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2,4-diamino-3,5-difluorobenzonitrile
;
_chemical_name_common            ?
_chemical_melting_point          408
_chemical_formula_moiety         'C7 H5 F2 N3'
_chemical_formula_sum            'C7 H5 F2 N3'
_chemical_formula_weight         169.14

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'
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                   7.1619(5)
_cell_length_b                   7.5769(6)
_cell_length_c                   7.6716(5)
_cell_angle_alpha                107.270(4)
_cell_angle_beta                 100.818(3)
_cell_angle_gamma                107.844(3)
_cell_volume                     360.19(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3328
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      29.61

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_F_000             172
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7285
_exptl_absorpt_correction_T_max  0.7460
_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            7318
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.921
_diffrn_reflns_theta_max         29.947
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1963
_reflns_number_gt                1457
_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)+(0.0847P)²+0.0541P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1963
_refine_ls_number_parameters     126
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1506
_refine_ls_wR_factor_gt          0.1338
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.002
_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 0.12801(17) 0.61949(14) 0.22543(13) 0.0543(3) Uani 1 1 d . . . . .
N3 N -0.0280(2) 0.2077(2) 0.09826(18) 0.0464(3) Uani 1 1 d D . . . .
H3A H -0.059(3) 0.269(3) 0.026(3) 0.064(6) Uiso 1 1 d D . . . .
H3B H -0.099(4) 0.087(3) 0.083(4) 0.089(8) Uiso 1 1 d D . . . .
C1 C 0.34074(19) 0.56434(19) 0.66368(17) 0.0326(3) Uani 1 1 d . . . . .
N1 N 0.5594(3) 0.7899(2) 1.0123(2) 0.0658(5) Uani 1 1 d . . . . .
F2 F 0.07855(16) 0.03918(12) 0.34850(13) 0.0529(3) Uani 1 1 d . . . . .
N2 N 0.3685(2) 0.86255(18) 0.5924(2) 0.0483(4) Uani 1 1 d D . . . .
H2A H 0.406(4) 0.937(4) 0.724(3) 0.093(8) Uiso 1 1 d D . . . .
H2B H 0.304(4) 0.917(4) 0.515(4) 0.097(9) Uiso 1 1 d D . . . .
C2 C 0.29583(19) 0.65811(18) 0.53796(18) 0.0317(3) Uani 1 1 d . . . . .
C3 C 0.1760(2) 0.53298(19) 0.35034(18) 0.0328(3) Uani 1 1 d . . . . .
C4 C 0.09580(19) 0.32556(19) 0.28238(17) 0.0316(3) Uani 1 1 d . . . . .
C5 C 0.1499(2) 0.24295(19) 0.41480(19) 0.0343(3) Uani 1 1 d . . . . .
C6 C 0.2674(2) 0.3550(2) 0.60086(19) 0.0359(3) Uani 1 1 d . . . . .
H6 H 0.298265 0.293593 0.684601 0.030(4) Uiso 1 1 calc R . . . .
C7 C 0.4623(2) 0.6866(2) 0.8583(2) 0.0424(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 1.3615(15) . ?
N3 C4 1.3690(17) . ?
N3 H3A 0.862(16) . ?
N3 H3B 0.862(17) . ?
C1 C6 1.4020(18) . ?
C1 C2 1.4031(18) . ?
C1 C7 1.4292(18) . ?
N1 C7 1.140(2) . ?
F2 C5 1.3625(15) . ?
N2 C2 1.3730(16) . ?
N2 H2A 0.936(17) . ?
N2 H2B 0.944(17) . ?
C2 C3 1.3908(18) . ?
C3 C4 1.3855(18) . ?
C4 C5 1.3972(19) . ?
C5 C6 1.3630(18) . ?
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
C4 N3 H3A 116.4(15) . . ?
C4 N3 H3B 114.1(18) . . ?
H3A N3 H3B 125(2) . . ?
C6 C1 C2 120.96(11) . . ?
C6 C1 C7 120.35(12) . . ?
C2 C1 C7 118.68(12) . . ?
C2 N2 H2A 115.8(17) . . ?
C2 N2 H2B 118.5(18) . . ?
H2A N2 H2B 113(2) . . ?
N2 C2 C3 120.53(12) . . ?
N2 C2 C1 122.85(12) . . ?
C3 C2 C1 116.60(11) . . ?
F1 C3 C4 117.32(11) . . ?
F1 C3 C2 117.98(11) . . ?
C4 C3 C2 124.66(12) . . ?
N3 C4 C3 122.84(12) . . ?
N3 C4 C5 121.70(12) . . ?
C3 C4 C5 115.47(12) . . ?
F2 C5 C6 120.25(12) . . ?
F2 C5 C4 116.27(12) . . ?
C6 C5 C4 123.48(12) . . ?
C5 C6 C1 118.78(12) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C1 177.60(17) . . ?

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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-t544
_database_code_depnum_ccdc_archive 'CCDC 2076051'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2,6-diamino-4-chloro-3,5-difluorobenzonitrile and 18-crown-6, 1:1 co-crystal
;
_chemical_name_common            ?
_chemical_melting_point          381
_chemical_formula_moiety         'C12 H24 O6, C7 H4 Cl F2 N3'
_chemical_formula_sum            'C19 H28 Cl F2 N3 O6'
_chemical_formula_weight         467.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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      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                   7.3003(11)
_cell_length_b                   9.7706(14)
_cell_length_c                   16.622(2)
_cell_angle_alpha                89.928(5)
_cell_angle_beta                 89.964(5)
_cell_angle_gamma                75.875(4)
_cell_volume                     1149.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.10

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.221
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8606
_exptl_absorpt_correction_T_max  0.9391
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(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            27857
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.225
_diffrn_reflns_theta_max         27.267
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5134
_reflns_number_gt                4394
_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 inversion 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)+(0.0333P)²+0.4093P] 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         5134
_refine_ls_number_parameters     297
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.73077(18) -0.46977(16) 0.14999(8) 0.0364(3) Uani 1 1 d . . . . .
Cl1 Cl 0.80852(9) -1.05531(5) -0.24547(5) 0.05540(17) Uani 1 1 d . . . . .
F1 F 0.79435(17) -0.87955(14) -0.10438(7) 0.0419(3) Uani 1 1 d . . . . .
N2 N 0.6950(2) -0.5886(2) -0.10005(11) 0.0307(4) Uani 1 1 d D . . . .
H2A H 0.678(3) -0.630(2) -0.0571(11) 0.028(6) Uiso 1 1 d D . . . .
H2B H 0.605(3) -0.510(2) -0.1029(15) 0.049(7) Uiso 1 1 d D . . . .
C1 C 0.6690(2) -0.58388(17) -0.24629(12) 0.0249(3) Uani 1 1 d . . . . .
O2 O 0.6375(2) -0.70226(15) 0.07469(8) 0.0355(3) Uani 1 1 d . . . . .
F2 F 0.73160(19) -0.86779(14) -0.38775(8) 0.0491(4) Uani 1 1 d . . . . .
N3 N 0.6428(3) -0.5799(2) -0.39308(11) 0.0370(4) Uani 1 1 d D . . . .
H3A H 0.614(3) -0.622(2) -0.4352(12) 0.044(7) Uiso 1 1 d D . . . .
H3B H 0.589(3) -0.4881(18) -0.3955(15) 0.043(7) Uiso 1 1 d D . . . .
C2 C 0.7027(2) -0.6579(2) -0.17212(11) 0.0247(4) Uani 1 1 d . . . . .
O3 O 0.39288(19) -0.76889(17) -0.03896(9) 0.0384(3) Uani 1 1 d . . . . .
N1 N 0.6172(3) -0.31447(19) -0.24388(13) 0.0502(5) Uani 1 1 d . . . . .
C3 C 0.7529(2) -0.8036(2) -0.17452(12) 0.0292(4) Uani 1 1 d . . . . .
O4 O 0.40059(19) -0.27509(16) 0.58946(9) 0.0389(4) Uani 1 1 d . . . . .
C4 C 0.7606(2) -0.87406(18) -0.24614(15) 0.0320(4) Uani 1 1 d . . . . .
O5 O 0.1661(2) -0.46352(18) 0.59619(9) 0.0407(4) Uani 1 1 d . . . . .
C5 C 0.7218(3) -0.7982(2) -0.31766(13) 0.0326(5) Uani 1 1 d . . . . .
O6 O 0.3252(2) -0.73671(18) 0.52882(9) 0.0421(4) Uani 1 1 d . . . . .
C6 C 0.6737(2) -0.6512(2) -0.32095(12) 0.0271(4) Uani 1 1 d . . . . .
C7 C 0.6357(3) -0.43361(19) -0.24561(12) 0.0301(4) Uani 1 1 d . . . . .
C8 C 0.8654(3) -0.5748(3) 0.10991(15) 0.0451(6) Uani 1 1 d . . . . .
H8A H 0.875907 -0.547908 0.052325 0.054 Uiso 1 1 d R U . . .
H8B H 0.995207 -0.581708 0.134225 0.054 Uiso 1 1 d R U . . .
C9 C 0.8095(3) -0.7112(3) 0.11756(14) 0.0442(6) Uani 1 1 d . . . . .
H9A H 0.910274 -0.788800 0.095385 0.053 Uiso 1 1 calc R U . . .
H9B H 0.791954 -0.731695 0.175003 0.053 Uiso 1 1 calc R U . . .
C10 C 0.5828(3) -0.8322(2) 0.07811(13) 0.0400(5) Uani 1 1 d . . . . .
H10A H 0.583198 -0.864478 0.134606 0.048 Uiso 1 1 calc R U . . .
H10B H 0.672926 -0.905258 0.047083 0.048 Uiso 1 1 calc R U . . .
C11 C 0.3891(3) -0.8103(2) 0.04343(13) 0.0400(5) Uani 1 1 d . . . . .
H11A H 0.346345 -0.898748 0.047280 0.048 Uiso 1 1 calc R U . . .
H11B H 0.299516 -0.736128 0.073992 0.048 Uiso 1 1 calc R U . . .
C12 C 0.2113(3) -0.7365(3) -0.07457(15) 0.0437(5) Uani 1 1 d . . . . .
H12A H 0.119401 -0.674752 -0.038302 0.052 Uiso 1 1 calc R U . . .
H12B H 0.169441 -0.824311 -0.083502 0.052 Uiso 1 1 calc R U . . .
C13 C 0.2196(3) -0.6619(2) -0.15448(13) 0.0393(5) Uani 1 1 d . . . . .
H13A H 0.312189 -0.725565 -0.189605 0.047 Uiso 1 1 calc R U . . .
H13B H 0.094446 -0.646371 -0.180699 0.047 Uiso 1 1 calc R U . . .
C14 C 0.2150(3) -0.2379(3) 0.62126(15) 0.0469(6) Uani 1 1 d . . . . .
H14A H 0.124001 -0.199107 0.577943 0.056 Uiso 1 1 calc R U . . .
H14B H 0.205984 -0.164258 0.662953 0.056 Uiso 1 1 calc R U . . .
C15 C 0.1671(3) -0.3658(3) 0.65738(14) 0.0441(6) Uani 1 1 d . . . . .
H15A H 0.261762 -0.407871 0.698717 0.053 Uiso 1 1 calc R U . . .
H15B H 0.041437 -0.338809 0.683439 0.053 Uiso 1 1 calc R U . . .
C16 C 0.1451(3) -0.5940(3) 0.62880(14) 0.0444(6) Uani 1 1 d . . . . .
H16A H 0.026735 -0.578366 0.660364 0.053 Uiso 1 1 calc R U . . .
H16B H 0.252342 -0.634847 0.664883 0.053 Uiso 1 1 calc R U . . .
C17 C 0.1398(3) -0.6915(3) 0.56109(14) 0.0446(5) Uani 1 1 d . . . . .
H17A H 0.095677 -0.773847 0.580338 0.053 Uiso 1 1 calc R U . . .
H17B H 0.051493 -0.642683 0.519085 0.053 Uiso 1 1 calc R U . . .
C18 C 0.3238(3) -0.7950(2) 0.45192(13) 0.0387(5) Uani 1 1 d . . . . .
H18A H 0.250596 -0.723186 0.414539 0.046 Uiso 1 1 calc R U . . .
H18B H 0.263468 -0.875297 0.453950 0.046 Uiso 1 1 calc R U . . .
C19 C 0.5216(3) -0.8440(2) 0.42309(14) 0.0414(5) Uani 1 1 d . . . . .
H19A H 0.597901 -0.908051 0.463394 0.050 Uiso 1 1 calc R U . . .
H19B H 0.524339 -0.896757 0.372124 0.050 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.404(2) . ?
O1 C13 1.421(3) 2_645 ?
Cl1 C4 1.7194(18) . ?
F1 C3 1.375(2) . ?
N2 C2 1.371(2) . ?
N2 H2A 0.843(15) . ?
N2 H2B 0.885(16) . ?
C1 C6 1.402(3) . ?
C1 C2 1.420(3) . ?
C1 C7 1.429(2) . ?
O2 C9 1.428(2) . ?
O2 C10 1.422(3) . ?
F2 C5 1.343(2) . ?
N3 C6 1.377(3) . ?
N3 H3A 0.863(16) . ?
N3 H3B 0.887(16) . ?
C2 C3 1.382(3) . ?
O3 C12 1.416(2) . ?
O3 C11 1.430(3) . ?
N1 C7 1.139(2) . ?
C3 C4 1.370(3) . ?
O4 C14 1.417(3) . ?
O4 C19 1.429(3) 2_646 ?
C4 C5 1.392(3) . ?
O5 C15 1.397(3) . ?
O5 C16 1.426(3) . ?
C5 C6 1.394(3) . ?
O6 C18 1.401(3) . ?
O6 C17 1.422(3) . ?
C8 C9 1.491(4) . ?
C8 H8A 1.0003 . ?
C8 H8B 1.0174 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.493(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.522(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.502(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.482(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.485(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 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
C8 O1 C13 113.55(16) . 2_645 ?
C2 N2 H2A 119.9(15) . . ?
C2 N2 H2B 108.5(17) . . ?
H2A N2 H2B 107(2) . . ?
C6 C1 C2 123.25(15) . . ?
C6 C1 C7 117.98(17) . . ?
C2 C1 C7 118.73(17) . . ?
C9 O2 C10 111.13(17) . . ?
C6 N3 H3A 119.7(17) . . ?
C6 N3 H3B 121.9(16) . . ?
H3A N3 H3B 110(2) . . ?
N2 C2 C3 120.25(19) . . ?
N2 C2 C1 121.75(17) . . ?
C3 C2 C1 117.94(17) . . ?
C12 O3 C11 112.48(16) . . ?
F1 C3 C4 119.30(18) . . ?
F1 C3 C2 119.91(18) . . ?
C4 C3 C2 120.79(19) . . ?
C14 O4 C19 112.98(17) . 2_646 ?
C3 C4 C5 119.78(16) . . ?
C3 C4 Cl1 119.07(17) . . ?
C5 C4 Cl1 121.09(16) . . ?
C15 O5 C16 110.74(18) . . ?
F2 C5 C4 119.52(18) . . ?
F2 C5 C6 117.2(2) . . ?
C4 C5 C6 123.25(18) . . ?
C18 O6 C17 111.73(15) . . ?
N3 C6 C5 121.59(19) . . ?
N3 C6 C1 123.43(18) . . ?
C5 C6 C1 114.91(18) . . ?
N1 C7 C1 176.9(2) . . ?
O1 C8 C9 108.54(18) . . ?
O1 C8 H8A 110.3 . . ?
C9 C8 H8A 111.7 . . ?
O1 C8 H8B 109.5 . . ?
C9 C8 H8B 111.2 . . ?
H8A C8 H8B 105.5 . . ?
O2 C9 C8 109.38(18) . . ?
O2 C9 H9A 109.8 . . ?
C8 C9 H9A 109.8 . . ?
O2 C9 H9B 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
O2 C10 C11 108.64(18) . . ?
O2 C10 H10A 110.0 . . ?
C11 C10 H10A 110.0 . . ?
O2 C10 H10B 110.0 . . ?
C11 C10 H10B 110.0 . . ?
H10A C10 H10B 108.3 . . ?
O3 C11 C10 109.13(18) . . ?
O3 C11 H11A 109.9 . . ?
C10 C11 H11A 109.9 . . ?
O3 C11 H11B 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
O3 C12 C13 109.12(17) . . ?
O3 C12 H12A 109.9 . . ?
C13 C12 H12A 109.9 . . ?
O3 C12 H12B 109.9 . . ?
C13 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
O1 C13 C12 115.79(18) 2_645 . ?
O1 C13 H13A 108.3 2_645 . ?
C12 C13 H13A 108.3 . . ?
O1 C13 H13B 108.3 2_645 . ?
C12 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
O4 C14 C15 109.72(18) . . ?
O4 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
O4 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
O5 C15 C14 108.62(19) . . ?
O5 C15 H15A 110.0 . . ?
C14 C15 H15A 110.0 . . ?
O5 C15 H15B 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.3 . . ?
O5 C16 C17 108.16(19) . . ?
O5 C16 H16A 110.1 . . ?
C17 C16 H16A 110.1 . . ?
O5 C16 H16B 110.1 . . ?
C17 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?
O6 C17 C16 108.34(17) . . ?
O6 C17 H17A 110.0 . . ?
C16 C17 H17A 110.0 . . ?
O6 C17 H17B 110.0 . . ?
C16 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
O6 C18 C19 108.84(17) . . ?
O6 C18 H18A 109.9 . . ?
C19 C18 H18A 109.9 . . ?
O6 C18 H18B 109.9 . . ?
C19 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
O4 C19 C18 109.42(18) 2_646 . ?
O4 C19 H19A 109.8 2_646 . ?
C18 C19 H19A 109.8 . . ?
O4 C19 H19B 109.8 2_646 . ?
C18 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.037

