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#$Date: 2020-03-28 04:41:31 +0200 (Sat, 28 Mar 2020) $
#$Revision: 249813 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/02/7240226.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_7240226
loop_
_publ_author_name
'Kilinkissa, Ornella E. Y.'
'Govender, Krishna Kuben'
'Bathori, Nikoletta B.'
_publ_section_title
;
 Melting point--solubility--structure correlations in chiral and racemic
 model cocrystals
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00014K
_journal_year                    2020
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2019-04-24 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                82.39(3)
_cell_angle_beta                 81.52(3)
_cell_angle_gamma                69.63(3)
_cell_formula_units_Z            2
_cell_length_a                   6.5593(13)
_cell_length_b                   9.2837(19)
_cell_length_c                   16.826(3)
_cell_measurement_reflns_used    4116
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.331
_cell_measurement_theta_min      2.349
_cell_volume                     946.4(4)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker Duo Apex II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4116
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.331
_diffrn_reflns_theta_min         2.349
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       chunk
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1195
_refine_ls_R_factor_gt           0.0777
_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)+(0.0349P)²+2.5587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1634
_refine_ls_wR_factor_ref         0.1803
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2860
_reflns_number_total             4116
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00014k2.cif
_cod_data_source_block           ETBIPYracPSA
_cod_database_code               7240226
_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   0.978
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.6058(5) -0.0413(3) 0.36089(14) 0.0424(7) Uani 1 1 d . . . . .
H1 H 0.688443 -0.005425 0.379475 0.051 Uiso 1 1 calc R U . . .
O2 O 0.8345(4) -0.0420(3) 0.24817(15) 0.0378(6) Uani 1 1 d . . . . .
O3 O 0.4489(4) 0.1613(2) 0.05888(13) 0.0289(5) Uani 1 1 d . . . . .
H3 H 0.393362 0.257615 0.051214 0.035 Uiso 1 1 calc R U . . .
O4 O 0.3460(5) 0.2056(3) 0.18932(15) 0.0422(7) Uani 1 1 d . . . . .
C7 C 0.5560(5) -0.2803(4) 0.25832(17) 0.0238(6) Uani 1 1 d . . . . .
C8 C 0.3793(6) -0.3354(4) 0.26984(19) 0.0298(7) Uani 1 1 d . . . . .
H8 H 0.233666 -0.264958 0.271764 0.036 Uiso 1 1 calc R U . . .
C9 C 0.4176(7) -0.4940(4) 0.2785(2) 0.0371(9) Uani 1 1 d . . . . .
H9 H 0.297268 -0.530809 0.286342 0.045 Uiso 1 1 calc R U . . .
C10 C 0.6272(7) -0.5976(4) 0.2758(2) 0.0371(9) Uani 1 1 d . . . . .
H10 H 0.651614 -0.705323 0.281452 0.044 Uiso 1 1 calc R U . . .
C11 C 0.8037(6) -0.5436(4) 0.2646(2) 0.0347(8) Uani 1 1 d . . . . .
H11 H 0.948958 -0.614565 0.262782 0.042 Uiso 1 1 calc R U . . .
C12 C 0.7672(5) -0.3869(4) 0.25624(19) 0.0285(7) Uani 1 1 d . . . . .
H12 H 0.888442 -0.351133 0.248919 0.034 Uiso 1 1 calc R U . . .
C13 C 0.5101(5) -0.1066(4) 0.24403(18) 0.0257(7) Uani 1 1 d . . . . .
H13 H 0.359003 -0.053739 0.269619 0.031 Uiso 1 1 calc R U . . .
C14 C 0.6693(5) -0.0592(4) 0.28323(19) 0.0275(7) Uani 1 1 d . . . . .
C15 C 0.5175(5) -0.0558(4) 0.15354(19) 0.0267(7) Uani 1 1 d . . . . .
H15A H 0.670760 -0.094331 0.128502 0.032 Uiso 1 1 calc R U . . .
H15B H 0.431127 -0.102610 0.128354 0.032 Uiso 1 1 calc R U . . .
C16 C 0.4275(5) 0.1190(4) 0.1367(2) 0.0270(7) Uani 1 1 d . . . . .
N1A N 0.2763(4) 0.4577(3) 0.02319(16) 0.0238(6) Uani 1 1 d . . . . .
C1A C 0.2468(5) 0.5226(4) -0.05257(19) 0.0261(7) Uani 1 1 d . . . . .
H1A H 0.293167 0.458306 -0.095856 0.031 Uiso 1 1 calc R U . . .
C2A C 0.1513(5) 0.6798(4) -0.06928(18) 0.0239(6) Uani 1 1 d . . . . .
H2A H 0.130509 0.721463 -0.123345 0.029 Uiso 1 1 calc R U . . .
C3A C 0.0854(5) 0.7774(3) -0.00761(18) 0.0216(6) Uani 1 1 d . . . . .
C4A C 0.1201(5) 0.7090(4) 0.07039(18) 0.0257(7) Uani 1 1 d . . . . .
H4A H 0.079006 0.770845 0.114636 0.031 Uiso 1 1 calc R U . . .
C5A C 0.2148(5) 0.5505(4) 0.08296(19) 0.0271(7) Uani 1 1 d . . . . .
H5A H 0.237009 0.505763 0.136487 0.032 Uiso 1 1 calc R U . . .
C6A C -0.0265(5) 0.9493(3) -0.02630(18) 0.0236(6) Uani 1 1 d . . . . .
H6A H -0.186768 0.971508 -0.019546 0.028 Uiso 1 1 calc R U . . .
H6B H 0.016559 0.977559 -0.083513 0.028 Uiso 1 1 calc R U . . .
N1B N 0.8104(5) 0.1028(3) 0.42635(16) 0.0335(7) Uani 1 1 d . . . . .
C1B C 1.0008(6) 0.1193(4) 0.3949(2) 0.0386(9) Uani 1 1 d . . . . .
H1B H 1.081213 0.061020 0.351281 0.046 Uiso 1 1 calc R U . . .
C2B C 1.0865(7) 0.2166(4) 0.4227(3) 0.0436(9) Uani 1 1 d . . . . .
H2B H 1.224495 0.222499 0.399143 0.052 Uiso 1 1 calc R U . . .
C3B C 0.9714(7) 0.3063(4) 0.4852(2) 0.0396(9) Uani 1 1 d . . . . .
C4B C 0.7736(7) 0.2879(4) 0.5179(2) 0.0443(10) Uani 1 1 d . . . . .
H4B H 0.688919 0.345700 0.561137 0.053 Uiso 1 1 calc R U . . .
C5B C 0.7003(7) 0.1862(4) 0.4877(2) 0.0374(8) Uani 1 1 d . . . . .
H5B H 0.565580 0.174767 0.511515 0.045 Uiso 1 1 calc R U . . .
C6B C 1.0553(8) 0.4182(4) 0.5162(3) 0.0540(12) Uani 1 1 d . . . . .
H6C H 1.030156 0.410904 0.575900 0.065 Uiso 1 1 calc R U . . .
H6D H 1.214966 0.389452 0.500519 0.065 Uiso 1 1 calc R U . . .
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'
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
C12 C7 C8 118.5(3) . . ?
C12 C7 C13 122.7(3) . . ?
C8 C7 C13 118.8(3) . . ?
C9 C8 C7 119.9(3) . . ?
C10 C9 C8 120.9(3) . . ?
C9 C10 C11 119.6(3) . . ?
C12 C11 C10 119.9(3) . . ?
C11 C12 C7 121.3(3) . . ?
C14 C13 C7 111.1(3) . . ?
C14 C13 C15 111.2(3) . . ?
C7 C13 C15 110.4(2) . . ?
O2 C14 O1 124.1(3) . . ?
O2 C14 C13 124.1(3) . . ?
O1 C14 C13 111.8(3) . . ?
C16 C15 C13 112.2(3) . . ?
O4 C16 O3 125.4(3) . . ?
O4 C16 C15 123.1(3) . . ?
O3 C16 C15 111.5(3) . . ?
C5A N1A C1A 118.0(3) . . ?
N1A C1A C2A 122.0(3) . . ?
C1A C2A C3A 120.5(3) . . ?
C2A C3A C4A 116.9(3) . . ?
C2A C3A C6A 120.0(3) . . ?
C4A C3A C6A 123.0(3) . . ?
C5A C4A C3A 119.6(3) . . ?
N1A C5A C4A 122.9(3) . . ?
C3A C6A C6A 114.4(3) . 2_575 ?
C1B N1B C5B 117.2(3) . . ?
N1B C1B C2B 123.2(3) . . ?
C1B C2B C3B 120.0(4) . . ?
C2B C3B C4B 116.5(3) . . ?
C2B C3B C6B 122.1(4) . . ?
C4B C3B C6B 121.5(4) . . ?
C5B C4B C3B 120.1(4) . . ?
N1B C5B C4B 122.9(4) . . ?
C6B C6B C3B 112.0(4) 2_766 . ?
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 C14 1.326(4) . ?
O2 C14 1.206(4) . ?
O3 C16 1.318(4) . ?
O4 C16 1.211(4) . ?
C7 C12 1.393(5) . ?
C7 C8 1.401(4) . ?
C7 C13 1.526(4) . ?
C8 C9 1.396(5) . ?
C9 C10 1.375(6) . ?
C10 C11 1.393(5) . ?
C11 C12 1.381(5) . ?
C13 C14 1.523(5) . ?
C13 C15 1.532(4) . ?
C15 C16 1.524(4) . ?
N1A C5A 1.336(4) . ?
N1A C1A 1.347(4) . ?
C1A C2A 1.382(4) . ?
C2A C3A 1.389(4) . ?
C3A C4A 1.394(4) . ?
C3A C6A 1.518(4) . ?
C4A C5A 1.384(4) . ?
C6A C6A 1.527(6) 2_575 ?
N1B C1B 1.335(5) . ?
N1B C5B 1.338(4) . ?
C1B C2B 1.376(5) . ?
C2B C3B 1.388(5) . ?
C3B C4B 1.390(6) . ?
C3B C6B 1.512(5) . ?
C4B C5B 1.377(5) . ?
C6B C6B 1.504(8) 2_766 ?
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 N1B 0.84 1.80 2.622(4) 167.5 .
O3 H3 N1A 0.84 1.77 2.609(3) 173.4 .
C5A H5A O4 0.95 2.69 3.349(4) 127.4 .
C1B H1B O2 0.95 2.98 3.527(4) 117.9 .
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
C12 C7 C8 C9 -0.3(5) . . . . ?
C13 C7 C8 C9 176.4(3) . . . . ?
C7 C8 C9 C10 -0.1(5) . . . . ?
C8 C9 C10 C11 0.3(5) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C10 C11 C12 C7 -0.3(5) . . . . ?
C8 C7 C12 C11 0.5(5) . . . . ?
C13 C7 C12 C11 -176.1(3) . . . . ?
C12 C7 C13 C14 -39.1(4) . . . . ?
C8 C7 C13 C14 144.3(3) . . . . ?
C12 C7 C13 C15 84.8(4) . . . . ?
C8 C7 C13 C15 -91.8(3) . . . . ?
C7 C13 C14 O2 96.1(4) . . . . ?
C15 C13 C14 O2 -27.4(4) . . . . ?
C7 C13 C14 O1 -83.1(3) . . . . ?
C15 C13 C14 O1 153.5(3) . . . . ?
C14 C13 C15 C16 -67.9(3) . . . . ?
C7 C13 C15 C16 168.2(3) . . . . ?
C13 C15 C16 O4 -4.8(5) . . . . ?
C13 C15 C16 O3 175.7(3) . . . . ?
C5A N1A C1A C2A -1.6(5) . . . . ?
N1A C1A C2A C3A 1.2(5) . . . . ?
C1A C2A C3A C4A -0.1(4) . . . . ?
C1A C2A C3A C6A -177.9(3) . . . . ?
C2A C3A C4A C5A -0.5(5) . . . . ?
C6A C3A C4A C5A 177.1(3) . . . . ?
C1A N1A C5A C4A 0.9(5) . . . . ?
C3A C4A C5A N1A 0.1(5) . . . . ?
C2A C3A C6A C6A -145.9(3) . . . 2_575 ?
C4A C3A C6A C6A 36.6(5) . . . 2_575 ?
C5B N1B C1B C2B 0.1(5) . . . . ?
N1B C1B C2B C3B -1.5(6) . . . . ?
C1B C2B C3B C4B 1.7(6) . . . . ?
C1B C2B C3B C6B -178.2(4) . . . . ?
C2B C3B C4B C5B -0.6(6) . . . . ?
C6B C3B C4B C5B 179.3(4) . . . . ?
C1B N1B C5B C4B 1.1(5) . . . . ?
C3B C4B C5B N1B -0.8(6) . . . . ?
C2B C3B C6B C6B 101.0(6) . . . 2_766 ?
C4B C3B C6B C6B -79.0(7) . . . 2_766 ?
