# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2116891'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2021-10-20 deposited with the CCDC.	2021-12-01 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H20 N, 2(H2 O2), Cl'
_chemical_formula_sum            'C8 H24 Cl N O4'
_chemical_formula_weight         233.73

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'

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

_cell_length_a                   11.8741(5)
_cell_length_b                   8.4164(3)
_cell_length_c                   12.6736(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1266.56(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.351
_cell_measurement_theta_max      30.515

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9167
_exptl_absorpt_correction_T_max  0.9711
_exptl_absorpt_process_details   'SADABS (Bruker, 2018)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART Photon II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14169
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         28.98
_reflns_number_total             3342
_reflns_number_gt                3271
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0757P)²+0.1688P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(5)
_refine_ls_number_reflns         3342
_refine_ls_number_parameters     223
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.041
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.69355(3) 0.85963(4) 0.61686(3) 0.02469(11) Uani 1 1 d . . .
N1 N 0.48951(9) 0.49623(15) 0.38746(9) 0.0150(2) Uani 1 1 d . . .
C1 C 0.48752(12) 0.38606(18) 0.48228(12) 0.0209(3) Uani 1 1 d . . .
C2 C 0.49285(14) 0.21054(19) 0.45496(17) 0.0304(4) Uani 1 1 d . . .
C3 C 0.59848(12) 0.47933(17) 0.32578(12) 0.0193(3) Uani 1 1 d . . .
C4 C 0.70435(12) 0.5167(2) 0.38728(16) 0.0275(3) Uani 1 1 d . . .
C5 C 0.47601(12) 0.66287(18) 0.43183(12) 0.0210(3) Uani 1 1 d . . .
C6 C 0.48496(16) 0.7952(2) 0.35156(18) 0.0319(4) Uani 1 1 d . . .
C7 C 0.39475(12) 0.45739(18) 0.31104(11) 0.0211(3) Uani 1 1 d . . .
C8 C 0.27876(14) 0.4504(2) 0.35965(14) 0.0277(3) Uani 1 1 d . . .
O1 O 0.79965(14) 0.27626(19) 0.67455(14) 0.0443(4) Uani 1 1 d . . .
O2 O 0.70176(12) 0.23388(17) 0.61310(18) 0.0420(3) Uani 1 1 d . . .
O3 O 0.94368(11) 0.60803(17) 0.68935(10) 0.0304(3) Uani 1 1 d . . .
O4 O 0.86392(9) 0.58209(13) 0.60310(9) 0.0253(2) Uani 1 1 d . . .
H1 H 0.815(2) 0.368(4) 0.648(3) 0.049(9) Uiso 1 1 d . . .
H2 H 0.705(2) 0.128(4) 0.618(4) 0.050(8) Uiso 1 1 d . . .
H3 H 1.007(2) 0.621(3) 0.663(2) 0.029(6) Uiso 1 1 d . . .
H4 H 0.8193(19) 0.666(3) 0.612(3) 0.031(5) Uiso 1 1 d . . .
H32 H 0.6006(17) 0.368(2) 0.2980(16) 0.010(4) Uiso 1 1 d . . .
H12 H 0.419(2) 0.417(3) 0.524(2) 0.026(5) Uiso 1 1 d . . .
H72 H 0.396(2) 0.535(3) 0.256(2) 0.029(6) Uiso 1 1 d . . .
H63 H 0.559(2) 0.799(3) 0.323(2) 0.031(6) Uiso 1 1 d . . .
H52 H 0.406(2) 0.668(3) 0.4668(18) 0.021(5) Uiso 1 1 d . . .
H23 H 0.565(2) 0.184(3) 0.421(2) 0.032(6) Uiso 1 1 d . . .
H31 H 0.5905(19) 0.546(3) 0.2641(19) 0.021(5) Uiso 1 1 d . . .
H51 H 0.5332(18) 0.677(3) 0.4850(18) 0.021(5) Uiso 1 1 d . . .
H11 H 0.5495(19) 0.424(3) 0.525(2) 0.025(5) Uiso 1 1 d . . .
H83 H 0.270(3) 0.364(3) 0.410(3) 0.040(7) Uiso 1 1 d . . .
H71 H 0.413(2) 0.354(3) 0.282(2) 0.030(6) Uiso 1 1 d . . .
H62 H 0.432(3) 0.790(5) 0.293(3) 0.063(10) Uiso 1 1 d . . .
H22 H 0.418(3) 0.176(4) 0.415(3) 0.052(8) Uiso 1 1 d . . .
H43 H 0.760(2) 0.503(3) 0.334(2) 0.041(7) Uiso 1 1 d . . .
H42 H 0.722(2) 0.446(3) 0.444(2) 0.039(7) Uiso 1 1 d . . .
H41 H 0.709(3) 0.628(4) 0.411(3) 0.049(9) Uiso 1 1 d . . .
H82 H 0.258(2) 0.554(3) 0.388(3) 0.042(7) Uiso 1 1 d . . .
H61 H 0.475(3) 0.894(4) 0.389(3) 0.053(9) Uiso 1 1 d . . .
H81 H 0.227(3) 0.438(3) 0.303(3) 0.053(8) Uiso 1 1 d . . .
H21 H 0.491(3) 0.162(4) 0.515(4) 0.068(11) 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
N1 C1 1.5180(18) . ?
N1 C3 1.5184(17) . ?
N1 C5 1.5196(18) . ?
N1 C7 1.5202(18) . ?
C1 C2 1.519(2) . ?
C1 H12 1.00(2) . ?
C1 H11 0.97(2) . ?
C2 H23 0.99(3) . ?
C2 H22 1.07(3) . ?
C2 H21 0.86(4) . ?
C3 C4 1.512(2) . ?
C3 H32 0.999(18) . ?
C3 H31 0.97(2) . ?
C4 H43 0.95(3) . ?
C4 H42 0.95(3) . ?
C4 H41 0.98(3) . ?
C5 C6 1.512(2) . ?
C5 H52 0.95(2) . ?
C5 H51 0.96(2) . ?
C6 H63 0.95(3) . ?
C6 H62 0.97(4) . ?
C6 H61 0.97(3) . ?
C7 C8 1.510(2) . ?
C7 H72 0.95(3) . ?
C7 H71 0.97(2) . ?
C8 H83 0.98(3) . ?
C8 H82 0.98(3) . ?
C8 H81 0.96(4) . ?
O1 O2 1.4439(19) . ?
O1 H1 0.86(3) . ?
O2 H2 0.89(3) . ?
O3 O4 1.4627(17) . ?
O3 H3 0.82(3) . ?
O4 H4 0.89(2) . ?

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
C1 N1 C3 111.33(11) . . ?
C1 N1 C5 105.62(11) . . ?
C3 N1 C5 111.52(11) . . ?
C1 N1 C7 111.19(11) . . ?
C3 N1 C7 106.41(11) . . ?
C5 N1 C7 110.86(11) . . ?
N1 C1 C2 114.40(14) . . ?
N1 C1 H12 105.7(14) . . ?
C2 C1 H12 113.8(14) . . ?
N1 C1 H11 102.9(15) . . ?
C2 C1 H11 114.8(14) . . ?
H12 C1 H11 104(2) . . ?
C1 C2 H23 110.7(15) . . ?
C1 C2 H22 109.9(17) . . ?
H23 C2 H22 118(2) . . ?
C1 C2 H21 105(3) . . ?
H23 C2 H21 108(3) . . ?
H22 C2 H21 105(3) . . ?
C4 C3 N1 115.06(12) . . ?
C4 C3 H32 110.8(12) . . ?
N1 C3 H32 106.9(12) . . ?
C4 C3 H31 112.2(13) . . ?
N1 C3 H31 106.1(14) . . ?
H32 C3 H31 105.2(17) . . ?
C3 C4 H43 100.4(17) . . ?
C3 C4 H42 115.9(17) . . ?
H43 C4 H42 108(2) . . ?
C3 C4 H41 114(2) . . ?
H43 C4 H41 107(3) . . ?
H42 C4 H41 110(3) . . ?
C6 C5 N1 115.05(13) . . ?
C6 C5 H52 110.0(14) . . ?
N1 C5 H52 108.1(14) . . ?
C6 C5 H51 109.4(14) . . ?
N1 C5 H51 107.2(14) . . ?
H52 C5 H51 106.8(18) . . ?
C5 C6 H63 110.3(16) . . ?
C5 C6 H62 116(2) . . ?
H63 C6 H62 108(3) . . ?
C5 C6 H61 107(2) . . ?
H63 C6 H61 106(2) . . ?
H62 C6 H61 109(3) . . ?
C8 C7 N1 115.06(12) . . ?
C8 C7 H72 110.0(15) . . ?
N1 C7 H72 107.7(15) . . ?
C8 C7 H71 109.1(16) . . ?
N1 C7 H71 105.5(16) . . ?
H72 C7 H71 109(2) . . ?
C7 C8 H83 113.2(18) . . ?
C7 C8 H82 110.5(17) . . ?
H83 C8 H82 113(3) . . ?
C7 C8 H81 107(2) . . ?
H83 C8 H81 110(3) . . ?
H82 C8 H81 102(2) . . ?
O2 O1 H1 101(2) . . ?
O1 O2 H2 100(2) . . ?
O4 O3 H3 107.9(19) . . ?
O3 O4 H4 100.3(19) . . ?

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
H1 O1 O2 H2 155(3) . . . . ?
H3 O3 O4 H4 -117(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O4 0.86(3) 1.97(3) 2.833(2) 173(3) .
O2 H2 Cl1 0.89(3) 2.26(3) 3.1517(15) 172(3) 1_545
O3 H3 Cl1 0.82(3) 2.30(3) 3.1179(13) 170(3) 3_565
O4 H4 Cl1 0.89(2) 2.21(2) 3.0951(12) 173(3) .

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.98
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.037
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2116894'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2021-10-20 deposited with the CCDC.	2021-12-01 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H14 N, H2 O2, Cl'
_chemical_formula_sum            'C9 H16 Cl N O2'
_chemical_formula_weight         205.68

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   7.2420(3)
_cell_length_b                   10.0690(4)
_cell_length_c                   14.7992(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.379(2)
_cell_angle_gamma                90.00
_cell_volume                     1061.50(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7255
_cell_measurement_theta_min      2.459
_cell_measurement_theta_max      30.472

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8657
_exptl_absorpt_correction_T_max  0.9677
_exptl_absorpt_process_details   'SADABS (Bruker, 2018)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART Photon II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10629
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0156
_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       18
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         26.99
_reflns_number_total             2287
_reflns_number_gt                2080
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0361P)²+0.3165P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2287
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0735
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.29524(4) 0.46638(3) 0.70278(2) 0.03354(11) Uani 1 1 d . . .
N1 N 0.79776(12) 0.65769(9) 0.60759(6) 0.0206(2) Uani 1 1 d . . .
C1 C 0.7924(2) 0.52472(12) 0.56043(9) 0.0310(3) Uani 1 1 d . . .
C2 C 0.61069(16) 0.72639(13) 0.58206(9) 0.0286(3) Uani 1 1 d . . .
C3 C 0.82940(18) 0.63175(13) 0.70915(8) 0.0280(3) Uani 1 1 d . . .
C4 C 0.94748(14) 0.74320(10) 0.57965(7) 0.0181(2) Uani 1 1 d . . .
C5 C 0.94234(15) 0.76391(11) 0.48621(7) 0.0221(2) Uani 1 1 d . . .
C6 C 1.08065(16) 0.84084(11) 0.45854(8) 0.0252(2) Uani 1 1 d . . .
C7 C 1.21965(15) 0.89872(11) 0.52265(8) 0.0260(2) Uani 1 1 d . . .
C8 C 1.22180(16) 0.87819(12) 0.61514(8) 0.0271(2) Uani 1 1 d . . .
C9 C 1.08627(15) 0.79962(11) 0.64451(7) 0.0234(2) Uani 1 1 d . . .
H5 H 0.844(2) 0.7248(13) 0.4422(9) 0.027(3) Uiso 1 1 d . . .
H6 H 1.081(2) 0.8532(15) 0.3951(10) 0.035(4) Uiso 1 1 d . . .
H7 H 1.314(2) 0.9518(15) 0.5042(10) 0.033(4) Uiso 1 1 d . . .
H8 H 1.317(2) 0.9147(14) 0.6594(10) 0.032(3) Uiso 1 1 d . . .
H9 H 1.0913(19) 0.7856(14) 0.7085(10) 0.029(3) Uiso 1 1 d . . .
H11 H 0.697(2) 0.4743(15) 0.5826(11) 0.041(4) Uiso 1 1 d . . .
H12 H 0.915(2) 0.4832(15) 0.5808(11) 0.037(4) Uiso 1 1 d . . .
H13 H 0.761(2) 0.5384(14) 0.4947(11) 0.033(4) Uiso 1 1 d . . .
H21 H 0.518(2) 0.6710(15) 0.6016(10) 0.033(4) Uiso 1 1 d . . .
H22 H 0.622(2) 0.8116(16) 0.6151(10) 0.038(4) Uiso 1 1 d . . .
H23 H 0.584(2) 0.7367(14) 0.5177(11) 0.033(4) Uiso 1 1 d . . .
H31 H 0.947(2) 0.5885(14) 0.7276(9) 0.027(3) Uiso 1 1 d . . .
H32 H 0.729(2) 0.5767(16) 0.7204(10) 0.035(4) Uiso 1 1 d . . .
H33 H 0.8264(19) 0.7154(15) 0.7409(10) 0.029(3) Uiso 1 1 d . . .
O1 O 0.59232(13) 0.27666(9) 0.65483(7) 0.0358(2) Uani 1 1 d . . .
O2 O 0.50491(13) 0.14594(9) 0.64196(6) 0.0341(2) Uani 1 1 d . . .
H1 H 0.504(3) 0.3209(18) 0.6744(12) 0.051(5) Uiso 1 1 d . . .
H2 H 0.570(3) 0.104(2) 0.6883(14) 0.062(5) 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
N1 C4 1.4999(13) . ?
N1 C3 1.5019(13) . ?
N1 C1 1.5071(14) . ?
N1 C2 1.5074(14) . ?
C1 H11 0.963(17) . ?
C1 H12 0.978(16) . ?
C1 H13 0.969(15) . ?
C2 H21 0.957(16) . ?
C2 H22 0.984(16) . ?
C2 H23 0.943(15) . ?
C3 H31 0.950(14) . ?
C3 H32 0.950(16) . ?
C3 H33 0.967(15) . ?
C4 C9 1.3809(15) . ?
C4 C5 1.3923(14) . ?
C5 C6 1.3852(16) . ?
C5 H5 0.958(14) . ?
C6 C7 1.3816(16) . ?
C6 H6 0.947(15) . ?
C7 C8 1.3817(17) . ?
C7 H7 0.948(15) . ?
C8 C9 1.3900(16) . ?
C8 H8 0.937(15) . ?
C9 H9 0.952(14) . ?
O1 O2 1.4580(12) . ?
O1 H1 0.873(19) . ?
O2 H2 0.87(2) . ?

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 N1 C3 112.84(8) . . ?
C4 N1 C1 110.00(8) . . ?
C3 N1 C1 107.19(9) . . ?
C4 N1 C2 109.22(8) . . ?
C3 N1 C2 107.39(9) . . ?
C1 N1 C2 110.15(9) . . ?
N1 C1 H11 105.7(9) . . ?
N1 C1 H12 106.9(9) . . ?
H11 C1 H12 109.8(13) . . ?
N1 C1 H13 108.7(9) . . ?
H11 C1 H13 111.3(13) . . ?
H12 C1 H13 114.0(12) . . ?
N1 C2 H21 107.7(9) . . ?
N1 C2 H22 106.7(9) . . ?
H21 C2 H22 110.9(13) . . ?
N1 C2 H23 108.3(9) . . ?
H21 C2 H23 110.1(12) . . ?
H22 C2 H23 113.0(13) . . ?
N1 C3 H31 109.5(8) . . ?
N1 C3 H32 107.1(9) . . ?
H31 C3 H32 110.6(13) . . ?
N1 C3 H33 108.8(8) . . ?
H31 C3 H33 110.9(12) . . ?
H32 C3 H33 109.8(12) . . ?
C9 C4 C5 120.98(10) . . ?
C9 C4 N1 121.09(9) . . ?
C5 C4 N1 117.94(9) . . ?
C6 C5 C4 119.08(10) . . ?
C6 C5 H5 121.1(8) . . ?
C4 C5 H5 119.9(8) . . ?
C7 C6 C5 120.60(10) . . ?
C7 C6 H6 119.7(9) . . ?
C5 C6 H6 119.7(9) . . ?
C8 C7 C6 119.60(10) . . ?
C8 C7 H7 119.3(9) . . ?
C6 C7 H7 121.0(9) . . ?
C7 C8 C9 120.82(10) . . ?
C7 C8 H8 120.5(9) . . ?
C9 C8 H8 118.6(9) . . ?
C4 C9 C8 118.90(10) . . ?
C4 C9 H9 121.6(9) . . ?
C8 C9 H9 119.5(9) . . ?
O2 O1 H1 100.2(12) . . ?
O1 O2 H2 99.7(13) . . ?

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
H1 O1 O2 H2 -107.0(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 Cl1 0.873(19) 2.197(19) 3.0548(11) 167.3(16) .
O2 H2 Cl1 0.87(2) 2.22(2) 3.0733(10) 169.3(18) 2_646

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2116892'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2021-10-20 deposited with the CCDC.	2021-12-01 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H13 Cl N, H2 O2, Cl'
_chemical_formula_sum            'C5 H15 Cl2 N O2'
_chemical_formula_weight         192.08

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   7.5628(2)
_cell_length_b                   9.9033(3)
_cell_length_c                   25.3929(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1901.84(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9752
_cell_measurement_theta_min      2.609
_cell_measurement_theta_max      30.507

_exptl_crystal_description       unshapen
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7855
_exptl_absorpt_correction_T_max  0.8576
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            35364
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0120
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         29.99
_reflns_number_total             5462
_reflns_number_gt                5422
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0264P)²+0.2509P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_number_reflns         5462
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0189
_refine_ls_R_factor_gt           0.0187
_refine_ls_wR_factor_ref         0.0493
_refine_ls_wR_factor_gt          0.0492
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl3 Cl 1.02165(3) 0.61187(2) 0.420324(11) 0.03016(6) Uani 1 1 d . . .
Cl4 Cl 0.77267(4) 0.05520(2) 0.323496(10) 0.02971(6) Uani 1 1 d . . .
N1 N 0.75764(10) 0.39822(8) 0.23442(3) 0.02050(14) Uani 1 1 d . . .
Cl1 Cl 0.32596(3) 0.37011(3) 0.329516(10) 0.03389(7) Uani 1 1 d . . .
C11 C 0.79899(15) 0.30235(12) 0.19047(4) 0.0321(2) Uani 1 1 d . . .
C12 C 0.90803(13) 0.39555(11) 0.27289(4) 0.02670(18) Uani 1 1 d . . .
C13 C 0.73934(14) 0.53835(10) 0.21240(4) 0.02636(18) Uani 1 1 d . . .
C14 C 0.58609(12) 0.35159(10) 0.25938(4) 0.02150(16) Uani 1 1 d . . .
C15 C 0.51717(16) 0.44570(12) 0.30115(5) 0.0345(2) Uani 1 1 d . . .
H111 H 0.694(2) 0.3043(17) 0.1664(7) 0.047(4) Uiso 1 1 d . . .
H112 H 0.905(2) 0.3314(15) 0.1730(6) 0.039(4) Uiso 1 1 d . . .
H113 H 0.807(2) 0.2199(16) 0.2060(5) 0.031(3) Uiso 1 1 d . . .
H121 H 1.013(2) 0.4185(16) 0.2549(6) 0.037(4) Uiso 1 1 d . . .
H122 H 0.920(2) 0.3066(15) 0.2866(6) 0.034(4) Uiso 1 1 d . . .
H123 H 0.885(2) 0.4588(15) 0.3011(6) 0.036(4) Uiso 1 1 d . . .
H131 H 0.640(2) 0.5391(16) 0.1908(6) 0.042(4) Uiso 1 1 d . . .
H132 H 0.845(2) 0.5582(15) 0.1922(5) 0.033(4) Uiso 1 1 d . . .
H133 H 0.7321(19) 0.6018(14) 0.2400(5) 0.025(3) Uiso 1 1 d . . .
H141 H 0.500(2) 0.3461(15) 0.2314(5) 0.032(3) Uiso 1 1 d . . .
H142 H 0.6054(19) 0.2656(15) 0.2731(5) 0.028(3) Uiso 1 1 d . . .
H151 H 0.600(3) 0.461(2) 0.3297(8) 0.066(6) Uiso 1 1 d . . .
H152 H 0.480(3) 0.531(2) 0.2865(7) 0.061(5) Uiso 1 1 d . . .
N2 N 0.46914(10) 0.49819(7) 0.49230(3) 0.01763(13) Uani 1 1 d . . .
Cl2 Cl 0.92424(3) 0.48695(3) 0.576647(10) 0.03202(7) Uani 1 1 d . . .
C21 C 0.37740(16) 0.37483(11) 0.47154(5) 0.0316(2) Uani 1 1 d . . .
C22 C 0.51006(14) 0.59072(11) 0.44724(4) 0.02680(19) Uani 1 1 d . . .
C23 C 0.34837(13) 0.56740(11) 0.53039(4) 0.02694(19) Uani 1 1 d . . .
C24 C 0.63611(12) 0.45087(9) 0.51911(3) 0.02070(16) Uani 1 1 d . . .
C25 C 0.75055(13) 0.56408(10) 0.53949(4) 0.02635(18) Uani 1 1 d . . .
H211 H 0.453(2) 0.3338(17) 0.4460(6) 0.043(4) Uiso 1 1 d . . .
H212 H 0.352(2) 0.3160(17) 0.5025(7) 0.047(4) Uiso 1 1 d . . .
H213 H 0.266(2) 0.4056(16) 0.4552(6) 0.038(4) Uiso 1 1 d . . .
H221 H 0.605(3) 0.5462(19) 0.4249(7) 0.053(5) Uiso 1 1 d . . .
H222 H 0.554(2) 0.6746(15) 0.4599(6) 0.036(4) Uiso 1 1 d . . .
H223 H 0.400(2) 0.6044(16) 0.4283(6) 0.036(4) Uiso 1 1 d . . .
H231 H 0.331(2) 0.5073(16) 0.5585(6) 0.040(4) Uiso 1 1 d . . .
H232 H 0.4036(19) 0.6531(14) 0.5436(5) 0.028(3) Uiso 1 1 d . . .
H233 H 0.2387(19) 0.5838(14) 0.5125(5) 0.028(3) Uiso 1 1 d . . .
H241 H 0.698(2) 0.3947(15) 0.4934(5) 0.032(3) Uiso 1 1 d . . .
H242 H 0.6008(19) 0.3944(14) 0.5466(5) 0.026(3) Uiso 1 1 d . . .
H251 H 0.691(2) 0.6219(16) 0.5634(5) 0.037(4) Uiso 1 1 d . . .
H252 H 0.8044(19) 0.6166(16) 0.5106(5) 0.034(4) Uiso 1 1 d . . .
O1 O 0.77106(13) 0.69560(8) 0.33239(3) 0.03625(18) Uani 1 1 d . . .
O2 O 0.63956(11) 0.77784(9) 0.35961(3) 0.03423(17) Uani 1 1 d . . .
H1 H 0.836(3) 0.6797(18) 0.3577(7) 0.045(4) Uiso 1 1 d . . .
H2 H 0.682(2) 0.8576(18) 0.3533(6) 0.042(4) Uiso 1 1 d . . .
O3 O 0.95619(15) 0.30652(10) 0.41229(5) 0.0557(3) Uani 1 1 d . . .
O4 O 0.76761(13) 0.28883(10) 0.40335(4) 0.0418(2) Uani 1 1 d . . .
H3 H 0.962(2) 0.388(2) 0.4116(7) 0.051(5) Uiso 1 1 d . . .
H4 H 0.769(2) 0.2278(18) 0.3825(6) 0.042(4) 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
N1 C11 1.4984(12) . ?
N1 C12 1.4994(12) . ?
N1 C13 1.5025(12) . ?
N1 C14 1.5160(12) . ?
Cl1 C15 1.7805(11) . ?
C11 H111 0.999(18) . ?
C11 H112 0.961(16) . ?
C11 H113 0.910(15) . ?
C12 H121 0.942(17) . ?
C12 H122 0.952(15) . ?
C12 H123 0.967(15) . ?
C13 H131 0.933(17) . ?
C13 H132 0.972(16) . ?
C13 H133 0.942(13) . ?
C14 C15 1.5050(14) . ?
C14 H141 0.965(15) . ?
C14 H142 0.932(14) . ?
C15 H151 0.97(2) . ?
C15 H152 0.97(2) . ?
N2 C23 1.4966(12) . ?
N2 C22 1.4982(11) . ?
N2 C21 1.5006(12) . ?
N2 C24 1.5092(11) . ?
Cl2 C25 1.7886(10) . ?
C21 H211 0.955(17) . ?
C21 H212 0.998(17) . ?
C21 H213 0.990(17) . ?
C22 H221 1.013(19) . ?
C22 H222 0.951(15) . ?
C22 H223 0.971(16) . ?
C23 H231 0.938(15) . ?
C23 H232 1.004(14) . ?
C23 H233 0.960(14) . ?
C24 C25 1.5080(13) . ?
C24 H241 0.977(14) . ?
C24 H242 0.934(14) . ?
C25 H251 0.946(16) . ?
C25 H252 0.987(15) . ?
O1 O2 1.4595(12) . ?
O1 H1 0.826(18) . ?
O2 H2 0.868(18) . ?
O3 O4 1.4547(14) . ?
O3 H3 0.810(19) . ?
O4 H4 0.803(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C12 108.41(8) . . ?
C11 N1 C13 109.10(8) . . ?
C12 N1 C13 109.18(8) . . ?
C11 N1 C14 107.28(8) . . ?
C12 N1 C14 111.80(7) . . ?
C13 N1 C14 110.98(7) . . ?
N1 C11 H111 106.1(10) . . ?
N1 C11 H112 109.2(9) . . ?
H111 C11 H112 111.9(13) . . ?
N1 C11 H113 105.1(9) . . ?
H111 C11 H113 109.8(13) . . ?
H112 C11 H113 114.2(13) . . ?
N1 C12 H121 108.5(9) . . ?
N1 C12 H122 109.1(9) . . ?
H121 C12 H122 108.7(13) . . ?
N1 C12 H123 109.6(9) . . ?
H121 C12 H123 110.6(13) . . ?
H122 C12 H123 110.2(12) . . ?
N1 C13 H131 107.5(10) . . ?
N1 C13 H132 107.9(9) . . ?
H131 C13 H132 110.8(12) . . ?
N1 C13 H133 110.2(8) . . ?
H131 C13 H133 112.6(13) . . ?
H132 C13 H133 107.8(12) . . ?
C15 C14 N1 113.73(8) . . ?
C15 C14 H141 108.8(9) . . ?
N1 C14 H141 106.6(9) . . ?
C15 C14 H142 110.9(8) . . ?
N1 C14 H142 107.5(9) . . ?
H141 C14 H142 109.3(12) . . ?
C14 C15 Cl1 107.82(7) . . ?
C14 C15 H151 113.3(12) . . ?
Cl1 C15 H151 106.8(12) . . ?
C14 C15 H152 111.8(11) . . ?
Cl1 C15 H152 106.5(12) . . ?
H151 C15 H152 110.2(16) . . ?
C23 N2 C22 109.85(8) . . ?
C23 N2 C21 108.53(8) . . ?
C22 N2 C21 108.98(8) . . ?
C23 N2 C24 111.17(7) . . ?
C22 N2 C24 111.20(7) . . ?
C21 N2 C24 107.01(7) . . ?
N2 C21 H211 107.9(11) . . ?
N2 C21 H212 106.8(10) . . ?
H211 C21 H212 113.8(13) . . ?
N2 C21 H213 107.0(9) . . ?
H211 C21 H213 110.9(13) . . ?
H212 C21 H213 110.1(13) . . ?
N2 C22 H221 107.9(10) . . ?
N2 C22 H222 110.5(9) . . ?
H221 C22 H222 108.7(15) . . ?
N2 C22 H223 106.7(9) . . ?
H221 C22 H223 112.8(13) . . ?
H222 C22 H223 110.2(13) . . ?
N2 C23 H231 106.6(10) . . ?
N2 C23 H232 110.5(8) . . ?
H231 C23 H232 109.8(12) . . ?
N2 C23 H233 107.3(8) . . ?
H231 C23 H233 110.3(13) . . ?
H232 C23 H233 112.1(11) . . ?
C25 C24 N2 113.84(7) . . ?
C25 C24 H241 112.2(9) . . ?
N2 C24 H241 105.9(8) . . ?
C25 C24 H242 110.7(8) . . ?
N2 C24 H242 106.5(9) . . ?
H241 C24 H242 107.2(12) . . ?
C24 C25 Cl2 106.56(7) . . ?
C24 C25 H251 113.4(10) . . ?
Cl2 C25 H251 105.6(9) . . ?
C24 C25 H252 111.9(8) . . ?
Cl2 C25 H252 108.3(9) . . ?
H251 C25 H252 110.6(13) . . ?
O2 O1 H1 98.4(12) . . ?
O1 O2 H2 99.6(11) . . ?
O4 O3 H3 99.9(13) . . ?
O3 O4 H4 100.4(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
H1 O1 O2 H2 94.0(16) . . . . ?
H3 O3 O4 H4 136.6(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 Cl3 0.826(18) 2.223(19) 3.0438(9) 172.4(17) .
O2 H2 Cl4 0.868(18) 2.207(18) 3.0659(9) 170.1(14) 1_565
O3 H3 Cl3 0.810(19) 2.27(2) 3.0710(10) 169.2(17) .
O4 H4 Cl4 0.803(17) 2.273(18) 3.0768(9) 180(2) .

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        29.99
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.232
_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_a_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2116893'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2021-10-20 deposited with the CCDC.	2021-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H20 N, 2(H2 O2), Br'
_chemical_formula_sum            'C8 H24 Br N O4'
_chemical_formula_weight         278.19

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   12.0887(6)
_cell_length_b                   8.5504(5)
_cell_length_c                   12.7308(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1315.90(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9997
_cell_measurement_theta_min      2.324
_cell_measurement_theta_max      30.295

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   0.4453
_exptl_transmission_factor_max   0.6478
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.118
_shelx_estimated_absorpt_T_min   0.455
_shelx_estimated_absorpt_T_max   0.860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22397
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_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         2.870
_diffrn_reflns_theta_max         28.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3496
_reflns_number_gt                3324
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.996

_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0151P)²+0.3172P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.184(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3496
_refine_ls_number_parameters     224
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0198
_refine_ls_wR_factor_ref         0.0429
_refine_ls_wR_factor_gt          0.0422
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
Br1 Br 0.69433(2) 0.86218(2) 0.61673(3) 0.02317(6) Uani 1 1 d . . . . .
N1 N 0.49096(18) 0.4948(2) 0.38732(14) 0.0146(4) Uani 1 1 d . . . . .
C1 C 0.4894(2) 0.3831(3) 0.4806(2) 0.0213(5) Uani 1 1 d . . . . .
C2 C 0.4968(3) 0.2118(3) 0.4517(3) 0.0315(6) Uani 1 1 d . . . . .
C3 C 0.59972(19) 0.4818(3) 0.32706(19) 0.0191(4) Uani 1 1 d . . . . .
C4 C 0.7024(2) 0.5184(4) 0.3902(3) 0.0262(7) Uani 1 1 d . . . . .
C5 C 0.4761(2) 0.6578(3) 0.4332(2) 0.0199(5) Uani 1 1 d . . . . .
C6 C 0.4837(3) 0.7894(3) 0.3554(3) 0.0323(6) Uani 1 1 d . . . . .
C7 C 0.3998(2) 0.4563(3) 0.30981(19) 0.0207(5) Uani 1 1 d . . . . .
C8 C 0.2854(3) 0.4462(5) 0.3567(3) 0.0289(7) Uani 1 1 d . . . . .
O1 O 0.8006(2) 0.2786(3) 0.6752(2) 0.0530(7) Uani 1 1 d . . . . .
O2 O 0.70291(16) 0.2465(2) 0.6155(4) 0.0456(5) Uani 1 1 d . . . . .
O3 O 0.94004(17) 0.6002(3) 0.69249(17) 0.0341(4) Uani 1 1 d . . . . .
O4 O 0.86780(14) 0.5748(2) 0.60228(18) 0.0273(4) Uani 1 1 d . . . . .
H1 H 0.815(3) 0.355(5) 0.648(4) 0.063(16) Uiso 1 1 d . . . . .
H2 H 0.707(3) 0.151(4) 0.631(6) 0.065(14) Uiso 1 1 d . . . . .
H3 H 1.002(3) 0.612(4) 0.662(3) 0.034(9) Uiso 1 1 d . . . . .
H4 H 0.828(2) 0.650(3) 0.605(4) 0.031(9) Uiso 1 1 d . . . . .
H32 H 0.606(2) 0.379(3) 0.302(2) 0.012(7) Uiso 1 1 d . . . . .
H12 H 0.427(3) 0.406(3) 0.520(2) 0.025(7) Uiso 1 1 d . . . . .
H72 H 0.403(2) 0.537(3) 0.257(2) 0.022(7) Uiso 1 1 d . . . . .
H63 H 0.550(3) 0.798(5) 0.320(3) 0.033(10) Uiso 1 1 d . . . . .
H52 H 0.406(3) 0.660(3) 0.468(2) 0.017(7) Uiso 1 1 d . . . . .
H23 H 0.566(3) 0.185(5) 0.417(3) 0.034(10) Uiso 1 1 d . . . . .
H31 H 0.592(2) 0.553(3) 0.268(2) 0.013(6) Uiso 1 1 d . . . . .
H51 H 0.534(3) 0.671(4) 0.488(3) 0.025(7) Uiso 1 1 d . . . . .
H11 H 0.548(2) 0.412(3) 0.526(2) 0.018(7) Uiso 1 1 d . . . . .
H83 H 0.274(3) 0.371(4) 0.412(3) 0.042(10) Uiso 1 1 d . . . . .
H71 H 0.422(3) 0.359(3) 0.278(3) 0.022(7) Uiso 1 1 d . . . . .
H62 H 0.431(3) 0.783(4) 0.297(3) 0.031(9) Uiso 1 1 d . . . . .
H22 H 0.430(4) 0.180(6) 0.410(4) 0.055(13) Uiso 1 1 d . . . . .
H43 H 0.762(4) 0.509(5) 0.344(3) 0.040(10) Uiso 1 1 d . . . . .
H42 H 0.715(3) 0.449(5) 0.446(3) 0.043(10) Uiso 1 1 d . . . . .
H41 H 0.703(3) 0.624(5) 0.416(4) 0.052(13) Uiso 1 1 d . . . . .
H82 H 0.259(3) 0.542(5) 0.386(3) 0.039(10) Uiso 1 1 d . . . . .
H61 H 0.475(3) 0.893(5) 0.389(3) 0.054(11) Uiso 1 1 d . . . . .
H81 H 0.237(3) 0.417(5) 0.303(3) 0.047(10) Uiso 1 1 d . . . . .
H21 H 0.498(3) 0.155(4) 0.514(3) 0.048(11) 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
N1 C7 1.516(3) . ?
N1 C5 1.521(3) . ?
N1 C1 1.524(3) . ?
N1 C3 1.526(3) . ?
C1 C2 1.513(4) . ?
C1 H12 0.92(3) . ?
C1 H11 0.95(3) . ?
C2 H23 0.97(4) . ?
C2 H22 1.00(5) . ?
C2 H21 0.93(4) . ?
C3 C4 1.511(4) . ?
C3 H32 0.94(3) . ?
C3 H31 0.98(3) . ?
C4 H43 0.94(4) . ?
C4 H42 0.93(4) . ?
C4 H41 0.96(4) . ?
C5 C6 1.502(4) . ?
C5 H52 0.95(3) . ?
C5 H51 1.00(3) . ?
C6 H63 0.92(4) . ?
C6 H62 0.98(4) . ?
C6 H61 0.99(4) . ?
C7 C8 1.508(4) . ?
C7 H72 0.96(3) . ?
C7 H71 0.97(3) . ?
C8 H83 0.96(4) . ?
C8 H82 0.95(4) . ?
C8 H81 0.94(4) . ?
O1 O2 1.431(3) . ?
O1 H1 0.76(4) . ?
O2 H2 0.84(4) . ?
O3 O4 1.459(3) . ?
O3 H3 0.85(4) . ?
O4 H4 0.81(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
C7 N1 C5 111.27(19) . . ?
C7 N1 C1 111.23(19) . . ?
C5 N1 C1 105.88(17) . . ?
C7 N1 C3 106.47(16) . . ?
C5 N1 C3 111.18(18) . . ?
C1 N1 C3 110.9(2) . . ?
C2 C1 N1 114.6(2) . . ?
C2 C1 H12 112.6(19) . . ?
N1 C1 H12 107.3(19) . . ?
C2 C1 H11 111.0(17) . . ?
N1 C1 H11 107.4(17) . . ?
H12 C1 H11 103(3) . . ?
C1 C2 H23 113(2) . . ?
C1 C2 H22 110(3) . . ?
H23 C2 H22 113(3) . . ?
C1 C2 H21 108(2) . . ?
H23 C2 H21 104(3) . . ?
H22 C2 H21 109(4) . . ?
C4 C3 N1 115.2(2) . . ?
C4 C3 H32 108.0(18) . . ?
N1 C3 H32 108.0(17) . . ?
C4 C3 H31 111.5(15) . . ?
N1 C3 H31 105.0(16) . . ?
H32 C3 H31 109(2) . . ?
C3 C4 H43 106(2) . . ?
C3 C4 H42 114(2) . . ?
H43 C4 H42 107(3) . . ?
C3 C4 H41 113(3) . . ?
H43 C4 H41 107(3) . . ?
H42 C4 H41 110(4) . . ?
C6 C5 N1 115.2(2) . . ?
C6 C5 H52 110.5(16) . . ?
N1 C5 H52 107.3(16) . . ?
C6 C5 H51 109.5(18) . . ?
N1 C5 H51 107.0(18) . . ?
H52 C5 H51 107(3) . . ?
C5 C6 H63 116(3) . . ?
C5 C6 H62 115(2) . . ?
H63 C6 H62 102(3) . . ?
C5 C6 H61 112(3) . . ?
H63 C6 H61 103(4) . . ?
H62 C6 H61 108(3) . . ?
C8 C7 N1 114.9(2) . . ?
C8 C7 H72 110.7(18) . . ?
N1 C7 H72 105.9(17) . . ?
C8 C7 H71 111.8(18) . . ?
N1 C7 H71 105.0(18) . . ?
H72 C7 H71 108(2) . . ?
C7 C8 H83 117(2) . . ?
C7 C8 H82 114(2) . . ?
H83 C8 H82 104(3) . . ?
C7 C8 H81 108(3) . . ?
H83 C8 H81 105(3) . . ?
H82 C8 H81 108(3) . . ?
O2 O1 H1 96(3) . . ?
O1 O2 H2 91(3) . . ?
O4 O3 H3 101(2) . . ?
O3 O4 H4 102(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
H1 O1 O2 H2 159(5) . . . . ?
H3 O3 O4 H4 -116(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O4 0.76(4) 2.07(4) 2.818(3) 168(5) . yes
O2 H2 Br1 0.84(4) 2.48(4) 3.2881(19) 161(6) 1_545 yes
O3 H3 Br1 0.85(4) 2.40(4) 3.238(2) 166(3) 3_565 yes
O4 H4 Br1 0.81(3) 2.43(3) 3.2353(18) 175(3) . yes

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.042

