#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/28/7212866.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_7212866
loop_
_publ_author_name
'Braga, Dario'
'Dichiarante, Elena'
'Palladino, Giuseppe'
'Grepioni, Fabrizia'
'Chierotti, Michele R.'
'Gobetto, Roberto'
'Pellegrino, Luca'
_publ_section_title
;
 Remarkable reversal of melting point alternation by co-crystallization
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              3534
_journal_paper_doi               10.1039/c0ce00253d
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C20 H26 N2 O4'
_chemical_formula_weight         358.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 114.656(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            6
_cell_length_a                   11.6701(5)
_cell_length_b                   20.9348(7)
_cell_length_c                   12.9988(5)
_cell_measurement_temperature    293(2)
_cell_volume                     2886.2(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.850
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13402
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0037(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         6159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0793
_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)+(0.0758P)²+2.2369P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1883
_refine_ls_wR_factor_ref         0.2062
_reflns_number_gt                3900
_reflns_number_total             6159
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00253d.txt
_cod_data_source_block           1.C8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2886.21(19)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7212866
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'
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
H1O H 0.807(3) 0.2587(18) 0.187(3) 0.088(12) Uiso 1 1 d .
H4O H 0.693(3) 0.5697(18) 0.305(3) 0.092(12) Uiso 1 1 d .
H3O H 0.294(3) 0.0882(18) -0.309(3) 0.085(12) Uiso 1 1 d .
O1 O 0.85514(19) 0.29636(9) 0.20238(16) 0.0520(5) Uani 1 1 d .
N1 N 0.7240(2) 0.18903(10) 0.14447(18) 0.0423(5) Uani 1 1 d .
O2 O 0.7874(2) 0.30772(10) 0.33657(18) 0.0728(7) Uani 1 1 d .
C1 C 0.9243(2) 0.38746(11) 0.3172(2) 0.0379(6) Uani 1 1 d .
H1A H 0.8903 0.4161 0.2527 0.045 Uiso 1 1 calc R
H1B H 1.0105 0.3776 0.3303 0.045 Uiso 1 1 calc R
C2 C 0.8486(2) 0.32657(12) 0.2883(2) 0.0383(6) Uani 1 1 d .
C3 C 0.9249(2) 0.42160(11) 0.42021(19) 0.0377(6) Uani 1 1 d .
H3A H 0.9593 0.3931 0.4848 0.045 Uiso 1 1 calc R
H3B H 0.8386 0.4313 0.4072 0.045 Uiso 1 1 calc R
C4 C 0.7206(3) 0.15640(12) 0.0556(2) 0.0469(7) Uani 1 1 d .
H4 H 0.7659 0.1717 0.0165 0.056 Uiso 1 1 calc R
C5 C 1.0005(2) 0.48305(11) 0.4486(2) 0.0400(6) Uani 1 1 d .
H5A H 1.0871 0.4735 0.4624 0.048 Uiso 1 1 calc R
H5B H 0.9666 0.5115 0.3840 0.048 Uiso 1 1 calc R
C6 C 0.6527(3) 0.10083(14) 0.0192(3) 0.0604(9) Uani 1 1 d .
H6 H 0.6526 0.0793 -0.0434 0.072 Uiso 1 1 calc R
C7 C 0.6578(3) 0.16608(13) 0.1985(2) 0.0486(7) Uani 1 1 d .
H7 H 0.6592 0.1884 0.2608 0.058 Uiso 1 1 calc R
C8 C 0.5879(3) 0.11118(14) 0.1669(2) 0.0574(8) Uani 1 1 d .
H8 H 0.5429 0.0972 0.2072 0.069 Uiso 1 1 calc R
C9 C 0.5843(3) 0.07703(15) 0.0762(3) 0.0661(10) Uani 1 1 d .
C10 C 0.5078(6) 0.0161(2) 0.0420(4) 0.149(3) Uani 1 1 d .
H10A H 0.5438 -0.0126 0.1063 0.179 Uiso 1 1 calc R
H10B H 0.4241 0.0269 0.0353 0.179 Uiso 1 1 calc R
N2 N 0.77274(19) 0.63707(9) 0.35560(17) 0.0405(5) Uani 1 1 d .
O3 O 0.3385(2) 0.12340(11) -0.30269(19) 0.0688(7) Uani 1 1 d .
O4 O 0.6466(2) 0.53064(10) 0.28262(18) 0.0583(6) Uani 1 1 d .
O5 O 0.7261(2) 0.52411(10) 0.15538(17) 0.0604(6) Uani 1 1 d .
C13 C 0.4216(2) 0.21490(12) -0.1939(2) 0.0423(6) Uani 1 1 d .
H13A H 0.3917 0.2429 -0.2594 0.051 Uiso 1 1 calc R
H13B H 0.5058 0.2009 -0.1807 0.051 Uiso 1 1 calc R
C14 C 0.5875(2) 0.40910(12) 0.0600(2) 0.0409(6) Uani 1 1 d .
H14A H 0.6744 0.3982 0.0775 0.049 Uiso 1 1 calc R
H14B H 0.5573 0.4371 -0.0054 0.049 Uiso 1 1 calc R
O6 O 0.2708(2) 0.14450(11) -0.17257(19) 0.0752(7) Uani 1 1 d .
C15 C 0.5099(3) 0.31158(12) -0.0682(2) 0.0440(6) Uani 1 1 d .
H15A H 0.4794 0.3388 -0.1347 0.053 Uiso 1 1 calc R
H15B H 0.5958 0.2993 -0.0523 0.053 Uiso 1 1 calc R
C16 C 0.6591(2) 0.50343(11) 0.1966(2) 0.0397(6) Uani 1 1 d .
C17 C 0.9081(3) 0.71681(13) 0.3387(2) 0.0492(7) Uani 1 1 d .
H17 H 0.9530 0.7324 0.2994 0.059 Uiso 1 1 calc R
N3 N 1.2008(2) 1.01906(10) 0.65175(19) 0.0492(6) Uani 1 1 d .
C18 C 0.4283(3) 0.25233(12) -0.0922(2) 0.0429(6) Uani 1 1 d .
H18A H 0.4612 0.2248 -0.0262 0.052 Uiso 1 1 calc R
H18B H 0.3437 0.2649 -0.1041 0.052 Uiso 1 1 calc R
C19 C 0.9117(3) 0.74872(12) 0.4322(2) 0.0470(7) Uani 1 1 d .
C20 C 0.5812(3) 0.44358(12) 0.1592(2) 0.0462(7) Uani 1 1 d .
H20A H 0.4939 0.4545 0.1400 0.055 Uiso 1 1 calc R
H20B H 0.6080 0.4143 0.2228 0.055 Uiso 1 1 calc R
C21 C 0.8388(3) 0.66220(13) 0.3033(2) 0.0455(6) Uani 1 1 d .
H21 H 0.8376 0.6416 0.2395 0.055 Uiso 1 1 calc R
C22 C 1.0605(3) 0.90675(13) 0.5896(2) 0.0493(7) Uani 1 1 d .
C23 C 0.5087(3) 0.34869(12) 0.0318(2) 0.0468(7) Uani 1 1 d .
H23A H 0.4222 0.3600 0.0157 0.056 Uiso 1 1 calc R
H23B H 0.5393 0.3211 0.0978 0.056 Uiso 1 1 calc R
C24 C 0.3366(3) 0.15758(12) -0.2200(2) 0.0421(6) Uani 1 1 d .
C25 C 0.9825(3) 0.84606(15) 0.5583(3) 0.0665(9) Uani 1 1 d .
H25A H 1.0092 0.8192 0.6250 0.080 Uiso 1 1 calc R
H25B H 0.8950 0.8574 0.5375 0.080 Uiso 1 1 calc R
C26 C 0.7759(2) 0.66721(12) 0.4466(2) 0.0449(6) Uani 1 1 d .
H26 H 0.7304 0.6503 0.4844 0.054 Uiso 1 1 calc R
C27 C 0.9893(3) 0.80920(15) 0.4677(3) 0.0679(10) Uani 1 1 d .
H27A H 1.0768 0.7978 0.4894 0.082 Uiso 1 1 calc R
H27B H 0.9643 0.8367 0.4018 0.082 Uiso 1 1 calc R
C28 C 0.8438(3) 0.72259(13) 0.4873(2) 0.0485(7) Uani 1 1 d .
H28 H 0.8440 0.7423 0.5515 0.058 Uiso 1 1 calc R
C29 C 1.0662(3) 0.94273(14) 0.6800(3) 0.0577(8) Uani 1 1 d .
H29 H 1.0225 0.9299 0.7221 0.069 Uiso 1 1 calc R
C30 C 1.1365(3) 0.99761(14) 0.7080(2) 0.0557(8) Uani 1 1 d .
H30 H 1.1393 1.0211 0.7697 0.067 Uiso 1 1 calc R
C31 C 1.1957(3) 0.98510(13) 0.5641(2) 0.0528(7) Uani 1 1 d .
H31 H 1.2397 0.9996 0.5233 0.063 Uiso 1 1 calc R
C32 C 1.1276(3) 0.92908(13) 0.5307(2) 0.0534(8) Uani 1 1 d .
H32 H 1.1268 0.9064 0.4689 0.064 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 0.0033 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
C2 O1 H1O 110(2) .
C4 N1 C7 117.4(2) .
C2 C1 C3 113.92(19) .
C2 C1 H1A 108.8 .
C3 C1 H1A 108.8 .
C2 C1 H1B 108.8 .
C3 C1 H1B 108.8 .
H1A C1 H1B 107.7 .
O2 C2 O1 123.1(2) .
O2 C2 C1 124.4(2) .
O1 C2 C1 112.6(2) .
C1 C3 C5 113.76(19) .
C1 C3 H3A 108.8 .
C5 C3 H3A 108.8 .
C1 C3 H3B 108.8 .
C5 C3 H3B 108.8 .
H3A C3 H3B 107.7 .
N1 C4 C6 122.6(2) .
N1 C4 H4 118.7 .
C6 C4 H4 118.7 .
C5 C5 C3 113.1(2) 3_766
C5 C5 H5A 108.9 3_766
C3 C5 H5A 108.9 .
C5 C5 H5B 108.9 3_766
C3 C5 H5B 108.9 .
H5A C5 H5B 107.8 .
C4 C6 C9 119.8(2) .
C4 C6 H6 120.1 .
C9 C6 H6 120.1 .
N1 C7 C8 123.3(2) .
N1 C7 H7 118.4 .
C8 C7 H7 118.4 .
C9 C8 C7 119.8(2) .
C9 C8 H8 120.1 .
C7 C8 H8 120.1 .
C8 C9 C6 117.2(2) .
C8 C9 C10 119.7(3) .
C6 C9 C10 123.1(3) .
C10 C10 C9 124.9(5) 3_655
C10 C10 H10A 106.1 3_655
C9 C10 H10A 106.1 .
C10 C10 H10B 106.1 3_655
C9 C10 H10B 106.1 .
H10A C10 H10B 106.3 .
C26 N2 C21 117.5(2) .
C24 O3 H3O 109(2) .
C16 O4 H4O 112(2) .
C24 C13 C18 113.6(2) .
C24 C13 H13A 108.8 .
C18 C13 H13A 108.8 .
C24 C13 H13B 108.8 .
C18 C13 H13B 108.8 .
H13A C13 H13B 107.7 .
C20 C14 C23 111.4(2) .
C20 C14 H14A 109.3 .
C23 C14 H14A 109.3 .
C20 C14 H14B 109.3 .
C23 C14 H14B 109.3 .
H14A C14 H14B 108.0 .
C18 C15 C23 111.4(2) .
C18 C15 H15A 109.3 .
C23 C15 H15A 109.3 .
C18 C15 H15B 109.3 .
C23 C15 H15B 109.3 .
H15A C15 H15B 108.0 .
O5 C16 O4 123.2(2) .
O5 C16 C20 125.1(2) .
O4 C16 C20 111.7(2) .
C21 C17 C19 120.1(2) .
C21 C17 H17 120.0 .
C19 C17 H17 120.0 .
C31 N3 C30 117.4(2) .
C13 C18 C15 113.8(2) .
C13 C18 H18A 108.8 .
C15 C18 H18A 108.8 .
C13 C18 H18B 108.8 .
C15 C18 H18B 108.8 .
H18A C18 H18B 107.7 .
C17 C19 C28 117.0(2) .
C17 C19 C27 118.1(2) .
C28 C19 C27 124.9(2) .
C16 C20 C14 115.9(2) .
C16 C20 H20A 108.3 .
C14 C20 H20A 108.3 .
C16 C20 H20B 108.3 .
C14 C20 H20B 108.3 .
H20A C20 H20B 107.4 .
N2 C21 C17 123.2(2) .
N2 C21 H21 118.4 .
C17 C21 H21 118.4 .
C29 C22 C32 116.8(2) .
C29 C22 C25 119.9(2) .
C32 C22 C25 123.3(2) .
C14 C23 C15 114.3(2) .
C14 C23 H23A 108.7 .
C15 C23 H23A 108.7 .
C14 C23 H23B 108.7 .
C15 C23 H23B 108.7 .
H23A C23 H23B 107.6 .
O6 C24 O3 122.3(2) .
O6 C24 C13 124.8(2) .
O3 C24 C13 112.9(2) .
C27 C25 C22 115.9(2) .
C27 C25 H25A 108.3 .
C22 C25 H25A 108.3 .
C27 C25 H25B 108.3 .
C22 C25 H25B 108.3 .
H25A C25 H25B 107.4 .
N2 C26 C28 122.6(2) .
N2 C26 H26 118.7 .
C28 C26 H26 118.7 .
C25 C27 C19 118.0(3) .
C25 C27 H27A 107.8 .
C19 C27 H27A 107.8 .
C25 C27 H27B 107.8 .
C19 C27 H27B 107.8 .
H27A C27 H27B 107.1 .
C26 C28 C19 119.7(2) .
C26 C28 H28 120.1 .
C19 C28 H28 120.1 .
C30 C29 C22 119.8(3) .
C30 C29 H29 120.1 .
C22 C29 H29 120.1 .
N3 C30 C29 123.5(2) .
N3 C30 H30 118.2 .
C29 C30 H30 118.2 .
N3 C31 C32 122.7(2) .
N3 C31 H31 118.6 .
C32 C31 H31 118.6 .
C31 C32 C22 119.8(2) .
C31 C32 H32 120.1 .
C22 C32 H32 120.1 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.313(3) .
O1 H1O 0.94(4) .
N1 C4 1.328(3) .
N1 C7 1.332(3) .
O2 C2 1.198(3) .
C1 C2 1.506(3) .
C1 C3 1.516(3) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C3 C5 1.516(3) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C6 1.376(3) .
C4 H4 0.9300 .
C5 C5 1.518(4) 3_766
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C9 1.388(4) .
C6 H6 0.9300 .
C7 C8 1.370(4) .
C7 H7 0.9300 .
C8 C9 1.366(4) .
C8 H8 0.9300 .
C9 C10 1.514(4) .
C10 C10 1.230(7) 3_655
C10 H10A 0.9700 .
C10 H10B 0.9700 .
N2 C26 1.327(3) .
N2 C21 1.331(3) .
O3 C24 1.300(3) .
O3 H3O 0.89(4) .
O4 C16 1.316(3) .
O4 H4O 0.96(4) .
O5 C16 1.198(3) .
C13 C24 1.502(3) .
C13 C18 1.511(3) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C20 1.506(3) .
C14 C23 1.516(3) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
O6 C24 1.200(3) .
C15 C18 1.515(3) .
C15 C23 1.520(3) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C20 1.505(3) .
C17 C21 1.365(4) .
C17 C19 1.373(3) .
C17 H17 0.9300 .
N3 C31 1.323(3) .
N3 C30 1.325(3) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 C28 1.383(4) .
C19 C27 1.512(4) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 H21 0.9300 .
C22 C29 1.374(4) .
C22 C32 1.384(4) .
C22 C25 1.517(4) .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
C25 C27 1.438(4) .
C25 H25A 0.9700 .
C25 H25B 0.9700 .
C26 C28 1.380(3) .
C26 H26 0.9300 .
C27 H27A 0.9700 .
C27 H27B 0.9700 .
C28 H28 0.9300 .
C29 C30 1.370(4) .
C29 H29 0.9300 .
C30 H30 0.9300 .
C31 C32 1.381(4) .
C31 H31 0.9300 .
C32 H32 0.9300 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139197735
