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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/26/1502677.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_1502677
loop_
_publ_author_name
'Corvis, Yohann'
'Négrier, Philippe'
'Lazerges, Mathieu'
'Massip, Stéphane'
'Léger, Jean-Michel'
'Espeau, Philippe'
_publ_section_title
;
 Lidocaine/L-menthol binary system: cocrystallization versus solid-state
 immiscibility.
;
_journal_issue                   16
_journal_name_full               'The journal of physical chemistry. B'
_journal_page_first              5420
_journal_page_last               5426
_journal_paper_doi               10.1021/jp101303j
_journal_volume                  114
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H42 N2 O2'
_chemical_formula_weight         390.60
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4016(5)
_cell_length_b                   13.4207(9)
_cell_length_c                   22.130(2)
_cell_measurement_reflns_used    2942
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      72.02
_cell_measurement_theta_min      6.53
_cell_volume                     2495.3(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Rigaku RAXIS Rapid'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'micro-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29398
_diffrn_reflns_theta_full        72.02
_diffrn_reflns_theta_max         72.02
_diffrn_reflns_theta_min         6.53
_exptl_absorpt_coefficient_mu    0.503
_exptl_absorpt_correction_T_max  0.9704
_exptl_absorpt_correction_T_min  0.9421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.040
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0650P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1225
_reflns_number_gt                2942
_reflns_number_total             4537
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp101303j_si_001.cif
_cod_data_source_block           lidoment
_cod_original_cell_volume        2495.3(4)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1502677
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
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
C1 C 0.1012(2) -0.07692(15) 0.38847(10) 0.0540(6) Uani 1 1 d .
H1 H 0.1325 -0.1465 0.3797 0.065 Uiso 1 1 calc R
C2 C -0.0481(2) -0.07904(16) 0.42647(12) 0.0662(6) Uani 1 1 d .
H2A H -0.1318 -0.1145 0.4044 0.079 Uiso 1 1 calc R
H2B H -0.0847 -0.0106 0.4331 0.079 Uiso 1 1 calc R
C3 C -0.0228(3) -0.12918(16) 0.48712(12) 0.0717(7) Uani 1 1 d .
H3 H 0.0063 -0.1995 0.4795 0.086 Uiso 1 1 calc R
C4 C 0.1166(3) -0.0795(2) 0.51955(12) 0.0832(8) Uani 1 1 d .
H4A H 0.0865 -0.0113 0.5305 0.100 Uiso 1 1 calc R
H4B H 0.1390 -0.1159 0.5570 0.100 Uiso 1 1 calc R
C5 C 0.2655(3) -0.07646(19) 0.48138(12) 0.0738(7) Uani 1 1 d .
H5A H 0.3031 -0.1447 0.4747 0.089 Uiso 1 1 calc R
H5B H 0.3488 -0.0405 0.5034 0.089 Uiso 1 1 calc R
C6 C 0.2392(2) -0.02611(15) 0.42033(10) 0.0565(6) Uani 1 1 d .
H6 H 0.2052 0.0431 0.4288 0.068 Uiso 1 1 calc R
O7 O 0.07270(18) -0.02715(10) 0.33198(7) 0.0686(4) Uani 1 1 d .
H7 H -0.0049 -0.0530 0.3149 0.103 Uiso 1 1 calc R
C8 C -0.1747(4) -0.12841(19) 0.52495(15) 0.0957(10) Uani 1 1 d .
H8A H -0.1587 -0.1678 0.5612 0.144 Uiso 1 1 calc R
H8B H -0.2615 -0.1565 0.5016 0.144 Uiso 1 1 calc R
H8C H -0.2006 -0.0604 0.5361 0.144 Uiso 1 1 calc R
C9 C 0.3888(3) -0.01951(16) 0.38121(12) 0.0701(7) Uani 1 1 d .
H9 H 0.3581 0.0150 0.3434 0.084 Uiso 1 1 calc R
C10 C 0.5188(3) 0.04297(17) 0.41066(13) 0.0877(9) Uani 1 1 d .
H10A H 0.6044 0.0537 0.3820 0.132 Uiso 1 1 calc R
H10B H 0.5597 0.0083 0.4458 0.132 Uiso 1 1 calc R
H10C H 0.4750 0.1067 0.4229 0.132 Uiso 1 1 calc R
C11 C 0.4576(3) -0.1210(2) 0.36291(16) 0.1052(10) Uani 1 1 d .
H11A H 0.5549 -0.1110 0.3401 0.158 Uiso 1 1 calc R
H11B H 0.3809 -0.1564 0.3382 0.158 Uiso 1 1 calc R
H11C H 0.4806 -0.1596 0.3989 0.158 Uiso 1 1 calc R
C20 C 0.0416(3) 0.24893(14) 0.38801(11) 0.0599(6) Uani 1 1 d .
C21 C 0.0901(4) 0.29535(16) 0.44111(13) 0.0789(7) Uani 1 1 d .
H21 H 0.0169 0.3039 0.4728 0.095 Uiso 1 1 calc R
C22 C 0.2444(4) 0.32898(17) 0.44785(14) 0.0870(9) Uani 1 1 d .
H22 H 0.2755 0.3610 0.4837 0.104 Uiso 1 1 calc R
C23 C 0.3524(3) 0.31547(17) 0.40199(15) 0.0790(8) Uani 1 1 d .
H23 H 0.4569 0.3390 0.4069 0.095 Uiso 1 1 calc R
C24 C 0.3105(2) 0.26759(15) 0.34839(11) 0.0605(6) Uani 1 1 d .
C25 C 0.1551(2) 0.23489(13) 0.34298(10) 0.0513(5) Uani 1 1 d .
C26 C -0.1268(3) 0.21493(18) 0.38020(13) 0.0818(8) Uani 1 1 d .
H26A H -0.1716 0.2455 0.3443 0.123 Uiso 1 1 calc R
H26B H -0.1887 0.2343 0.4153 0.123 Uiso 1 1 calc R
H26C H -0.1290 0.1430 0.3760 0.123 Uiso 1 1 calc R
C27 C 0.4290(3) 0.25376(17) 0.29894(14) 0.0887(8) Uani 1 1 d .
H27A H 0.4332 0.1840 0.2877 0.133 Uiso 1 1 calc R
H27B H 0.5331 0.2751 0.3128 0.133 Uiso 1 1 calc R
H27C H 0.3978 0.2932 0.2642 0.133 Uiso 1 1 calc R
N28 N 0.10683(18) 0.18584(11) 0.28874(8) 0.0525(5) Uani 1 1 d .
H28 H 0.0957 0.1214 0.2895 0.063 Uiso 1 1 calc R
C29 C 0.0780(3) 0.23293(14) 0.23719(11) 0.0617(6) Uani 1 1 d .
O30 O 0.0949(2) 0.32390(10) 0.23126(8) 0.0856(6) Uani 1 1 d .
C31 C 0.0273(4) 0.16955(15) 0.18464(12) 0.0881(9) Uani 1 1 d .
H31A H -0.0719 0.1970 0.1683 0.106 Uiso 1 1 calc R
H31B H 0.1083 0.1751 0.1530 0.106 Uiso 1 1 calc R
N32 N 0.0027(2) 0.06571(12) 0.19730(9) 0.0656(5) Uani 1 1 d .
C33 C 0.1186(4) -0.0023(2) 0.16463(15) 0.0989(10) Uani 1 1 d .
H33A H 0.0863 -0.0717 0.1707 0.119 Uiso 1 1 calc R
H33B H 0.1144 0.0117 0.1212 0.119 Uiso 1 1 calc R
C34 C 0.2832(4) 0.0109(3) 0.18625(18) 0.1436(14) Uani 1 1 d .
H34A H 0.3147 0.0799 0.1813 0.215 Uiso 1 1 calc R
H34B H 0.3540 -0.0316 0.1631 0.215 Uiso 1 1 calc R
H34C H 0.2893 -0.0071 0.2286 0.215 Uiso 1 1 calc R
C35 C -0.1578(4) 0.0298(2) 0.18564(17) 0.1089(12) Uani 1 1 d .
H35A H -0.1577 -0.0432 0.1865 0.131 Uiso 1 1 calc R
H35B H -0.1905 0.0508 0.1451 0.131 Uiso 1 1 calc R
C36 C -0.2747(4) 0.0672(3) 0.2301(2) 0.1500(16) Uani 1 1 d .
H36A H -0.2530 0.0379 0.2694 0.225 Uiso 1 1 calc R
H36B H -0.3813 0.0490 0.2173 0.225 Uiso 1 1 calc R
H36C H -0.2666 0.1391 0.2329 0.225 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O7 C1 C2 110.79(17)
O7 C1 C6 108.79(16)
C2 C1 C6 112.57(19)
C1 C2 C3 112.65(18)
C2 C3 C8 111.4(2)
C2 C3 C4 109.2(2)
C8 C3 C4 112.4(2)
C5 C4 C3 112.6(2)
C4 C5 C6 112.7(2)
C1 C6 C5 108.83(18)
C1 C6 C9 113.01(19)
C5 C6 C9 114.04(19)
C10 C9 C6 112.3(2)
C10 C9 C11 109.4(2)
C6 C9 C11 114.09(19)
C21 C20 C25 117.7(2)
C21 C20 C26 120.7(2)
C25 C20 C26 121.6(2)
C22 C21 C20 120.8(3)
C23 C22 C21 119.8(3)
C22 C23 C24 121.5(2)
C25 C24 C23 117.3(2)
C25 C24 C27 121.8(2)
C23 C24 C27 120.9(2)
C24 C25 C20 122.8(2)
C24 C25 N28 119.2(2)
C20 C25 N28 118.03(18)
C29 N28 C25 123.73(16)
O30 C29 N28 122.8(2)
O30 C29 C31 120.6(2)
N28 C29 C31 116.60(17)
N32 C31 C29 116.0(2)
C31 N32 C35 114.8(2)
C31 N32 C33 113.5(2)
C35 N32 C33 108.1(2)
C34 C33 N32 112.0(3)
N32 C35 C36 112.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O7 1.437(2)
C1 C2 1.510(3)
C1 C6 1.519(3)
C2 C3 1.516(3)
C3 C8 1.526(4)
C3 C4 1.527(4)
C4 C5 1.511(4)
C5 C6 1.527(3)
C6 C9 1.529(3)
C9 C10 1.523(3)
C9 C11 1.534(3)
C20 C21 1.391(3)
C20 C25 1.392(3)
C20 C26 1.496(3)
C21 C22 1.381(4)
C22 C23 1.373(4)
C23 C24 1.394(3)
C24 C25 1.383(3)
C24 C27 1.491(3)
C25 N28 1.428(3)
N28 C29 1.326(2)
C29 O30 1.236(2)
C29 C31 1.503(3)
C31 N32 1.437(3)
N32 C35 1.455(3)
N32 C33 1.518(3)
C33 C34 1.474(5)
C35 C36 1.478(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
O7 C1 C2 C3 -178.89(16)
C6 C1 C2 C3 -56.8(2)
C1 C2 C3 C8 178.91(19)
C1 C2 C3 C4 54.2(3)
C2 C3 C4 C5 -53.6(3)
C8 C3 C4 C5 -177.8(2)
C3 C4 C5 C6 55.5(3)
O7 C1 C6 C5 177.93(17)
C2 C1 C6 C5 54.7(2)
O7 C1 C6 C9 -54.3(2)
C2 C1 C6 C9 -177.50(18)
C4 C5 C6 C1 -54.3(3)
C4 C5 C6 C9 178.55(19)
C1 C6 C9 C10 172.75(17)
C5 C6 C9 C10 -62.3(3)
C1 C6 C9 C11 -62.1(3)
C5 C6 C9 C11 62.9(3)
C25 C20 C21 C22 2.0(3)
C26 C20 C21 C22 -178.4(2)
C20 C21 C22 C23 -0.8(3)
C21 C22 C23 C24 -0.5(4)
C22 C23 C24 C25 0.6(3)
C22 C23 C24 C27 179.8(2)
C23 C24 C25 C20 0.7(3)
C27 C24 C25 C20 -178.56(19)
C23 C24 C25 N28 179.73(17)
C27 C24 C25 N28 0.5(3)
C21 C20 C25 C24 -2.0(3)
C26 C20 C25 C24 178.5(2)
C21 C20 C25 N28 179.00(17)
C26 C20 C25 N28 -0.6(3)
C24 C25 N28 C29 -76.1(2)
C20 C25 N28 C29 103.0(2)
C25 N28 C29 O30 2.1(3)
C25 N28 C29 C31 -179.6(2)
O30 C29 C31 N32 -176.6(2)
N28 C29 C31 N32 5.0(3)
C29 C31 N32 C35 119.6(3)
C29 C31 N32 C33 -115.3(3)
C31 N32 C33 C34 66.6(3)
C35 N32 C33 C34 -164.8(3)
C31 N32 C35 C36 -71.5(4)
C33 N32 C35 C36 160.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139037581
