#------------------------------------------------------------------------------
#$Date: 2020-03-06 03:58:33 +0100 (vie 06 de mar de 2020) $
#$Revision: 249106 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/00/7240054.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7240054
loop_
_publ_author_name
'Odounga Odounga, Jean-Eudes'
'Báthori, Nikoletta B.'
_publ_section_title
;
 Systematic comparison of racemic and enantiopure multicomponent crystals
 of phenylsuccinic acid---the role of chirality
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00072H
_journal_year                    2020
_chemical_formula_sum            'C9 H24 N2 O3'
_chemical_formula_weight         208.30
_chemical_melting_point          378.81
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_Hall           '-R 3 2"c'
_space_group_name_H-M_alt        'R -3 c :H'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2020-01-09 deposited with the CCDC.	2020-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   6.3212(9)
_cell_length_b                   6.3212(9)
_cell_length_c                   53.448(11)
_cell_measurement_reflns_used    1594
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.96
_cell_measurement_theta_min      2.28
_cell_volume                     1849.5(5)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       70
_diffrn_reflns_limit_l_min       -70
_diffrn_reflns_number            4739
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.417
_diffrn_reflns_theta_min         2.286
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_description       chunk
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: tert-butylamine'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0051(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     26
_refine_ls_number_reflns         528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0553P)²+0.6075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0946
_reflns_Friedel_coverage         0.000
_reflns_number_gt                484
_reflns_number_total             528
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00072h2.cif
_cod_data_source_block           tba-coo
_cod_original_cell_volume        1849.5(6)
_cod_database_code               7240054
_shelx_shelxl_version_number     2016/4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.994
_shelx_res_file
;
TITL rmin3c in R-3c
 C:\Students\EUDES_~1\JEO110~1\rmin3c.res created by SHELXL-2016/4 at 15:49:59 on 11-Feb-2019
CELL 0.71073 6.3212 6.3212 53.4480 90.000 90.000 120.000
ZERR 6.0000 0.0009 0.0009 0.0107 0.000 0.000 0.000
LATT 3
SYMM -Y, X-Y, Z
SYMM -X+Y, -X, Z
SYMM X-Y, -Y, 0.5-Z
SYMM -X, -X+Y, 0.5-Z
SYMM Y, X, 0.5-Z
SFAC C H O N
UNIT 54 144 18 12
HTAB N3 O5
ACTA
FMAP 2 1 53
PLAN 20 0 0
HTAB 2.0
MERG 2
SIZE 0.07 0.38 0.4
TEMP -100
L.S. 20
WGHT    0.055300    0.607500
EXTI    0.005063
FVAR       0.13410
C1    1    0.333333    0.666667    0.040767    10.33333    0.01729    0.01729 =
         0.02460    0.00000    0.00000    0.00865
AFIX   3
H1    2    0.394800    0.566000    0.074707    11.00000    0.03105
AFIX   0
C2    1    0.587874    0.730580    0.032061    11.00000    0.02329    0.03144 =
         0.03443    0.00496    0.00848    0.01396
AFIX 137
H2B   2    0.707730    0.892043    0.038487    11.00000   -1.50000
H2C   2    0.593121    0.732575    0.013734    11.00000   -1.50000
H2A   2    0.626595    0.608255    0.038360    11.00000   -1.50000
AFIX   0
N3    4    0.333333    0.666667    0.068882    10.33333    0.01451    0.01451 =
         0.02433    0.00000    0.00000    0.00725
C4    1    0.666667    0.333333    0.083333    10.16665    0.01280    0.01280 =
         0.02210    0.00000    0.00000    0.00640
O5    3    0.463683    0.333333    0.083333    10.50000    0.01406    0.01919 =
         0.04595    0.00819    0.00409    0.00960
HKLF 4




REM  rmin3c in R-3c
REM R1 =  0.0331 for     484 Fo > 4sig(Fo)  and  0.0359 for all     528 data
REM     26 parameters refined using      0 restraints

END

WGHT      0.0525      0.6759

REM Instructions for potential hydrogen bonds
HTAB N3 O5

REM Highest difference peak  0.287,  deepest hole -0.135,  1-sigma level  0.036
Q1    1   0.2320  0.5370  0.0403  11.00000  0.05    0.29
Q2    1   0.3333  0.6667  0.0532  10.33333  0.05    0.28
Q3    1   0.4610  0.7003  0.0327  11.00000  0.05    0.27
Q4    1   0.5544  0.3333  0.0833  10.50000  0.05    0.18
Q5    1   0.3949  0.2451  0.0817  11.00000  0.05    0.15
Q6    1   0.6794  0.6761  0.0491  11.00000  0.05    0.08
Q7    1   0.7462  0.8557  0.0432  11.00000  0.05    0.08
Q8    1   0.6790  0.8921  0.0271  11.00000  0.05    0.07
Q9    1   0.7858  0.7585  0.0595  11.00000  0.05    0.07
Q10   1   1.0000  1.0000  0.0000  10.16667  0.05    0.07
Q11   1   0.5882  0.5932  0.0217  11.00000  0.05    0.07
Q12   1   0.3712  0.3628  0.0991  11.00000  0.05    0.07
Q13   1   0.5600  0.6389  0.0099  11.00000  0.05    0.07
Q14   1   0.5623  0.6505  0.0033  11.00000  0.05    0.06
Q15   1   0.9303  0.8815  0.0078  11.00000  0.05    0.06
Q16   1   0.5692  0.8028 -0.0017  11.00000  0.05    0.05
Q17   1   0.3333  0.6667  0.0033  10.33333  0.05    0.05
Q18   1   0.7733  0.8842  0.0533  11.00000  0.05    0.05
Q19   1   0.7517  0.8366  0.0034  11.00000  0.05    0.05
Q20   1   0.8499  0.7496  0.0569  11.00000  0.05    0.05
;
_shelx_res_checksum              7579
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'y, x, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'y+2/3, x+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'y+1/3, x+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-y, -x, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-y+2/3, -x+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-y+1/3, -x+2/3, z+1/6'
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 0.333333 0.666667 0.04077(2) 0.0197(3) Uani 1 3 d S T P . .
H1 H 0.394800 0.566000 0.074707 0.031(3) Uiso 1 1 d R . . . .
C2 C 0.58787(17) 0.73058(18) 0.03206(2) 0.0296(3) Uani 1 1 d . . . . .
H2B H 0.707730 0.892043 0.038487 0.044 Uiso 1 1 calc R U . . .
H2C H 0.593121 0.732575 0.013734 0.044 Uiso 1 1 calc R U . . .
H2A H 0.626595 0.608255 0.038360 0.044 Uiso 1 1 calc R U . . .
N3 N 0.333333 0.666667 0.06888(2) 0.0178(3) Uani 1 3 d S T P . .
C4 C 0.666667 0.333333 0.083333 0.0159(4) Uani 1 6 d S T P . .
O5 O 0.46368(13) 0.333333 0.083333 0.0258(3) Uani 1 2 d S T P . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0173(5) 0.0173(5) 0.0246(7) 0.000 0.000 0.0086(2)
C2 0.0233(5) 0.0314(5) 0.0344(5) 0.0050(3) 0.0085(3) 0.0140(4)
N3 0.0145(4) 0.0145(4) 0.0243(6) 0.000 0.000 0.00725(19)
C4 0.0128(6) 0.0128(6) 0.0221(8) 0.000 0.000 0.0064(3)
O5 0.0141(4) 0.0192(4) 0.0460(5) 0.0082(3) 0.00409(17) 0.0096(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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'
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
N3 C1 C2 107.80(6) . 2_665 ?
N3 C1 C2 107.80(6) . 3_565 ?
C2 C1 C2 111.09(5) 2_665 3_565 ?
N3 C1 C2 107.79(6) . . ?
C2 C1 C2 111.09(5) 2_665 . ?
C2 C1 C2 111.09(5) 3_565 . ?
O5 C4 O5 120.0 2_655 3_665 ?
O5 C4 O5 120.000(1) 2_655 . ?
O5 C4 O5 120.0 3_665 . ?
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 N3 1.5027(16) . ?
C1 C2 1.5227(10) 2_665 ?
C1 C2 1.5227(10) 3_565 ?
C1 C2 1.5227(10) . ?
C4 O5 1.2831(8) 2_655 ?
C4 O5 1.2831(8) 3_665 ?
C4 O5 1.2831(8) . ?
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
N3 H1 O5 0.95 1.79 2.7297(7) 170.0 .
