#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/22/4502269.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_4502269
loop_
_publ_author_name
'Angelici, Gaetano'
'Castellucci, Nicola'
'Contaldi, Simone'
'Falini, Giuseppe'
'Hofmann, Hans-Jörg'
'Monari, Magda'
'Tomasini, Claudia'
_publ_section_title
;
 A Network of Small Molecules Connected by Cross-Linked NH Bonds
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              244
_journal_paper_doi               10.1021/cg900874f
_journal_volume                  10
_journal_year                    2010
_chemical_formula_sum            'C25 H29 N3 O6'
_chemical_formula_weight         467.51
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 92.6000(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.3361(12)
_cell_length_b                   11.5818(14)
_cell_length_c                   10.4904(13)
_cell_measurement_temperature    296(2)
_cell_volume                     1254.5(3)
_computing_cell_refinement       SMART
_computing_data_collection       SMART
_computing_data_reduction        SAINT+
_computing_molecular_graphics    'SCHAKAL99 (Keller 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Giacovazzo, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART Apex II CCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13752
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.059(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5688
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0362
_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)+(0.0667P)²+0.0806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                5392
_reflns_number_total             5688
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg900874f_si_002.cif
_cod_data_source_block           comp1c
_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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4502269
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O6 O 0.05878(8) -0.07013(9) 0.21712(9) 0.0513(2) Uani 1 1 d .
O5 O 0.27496(9) -0.05629(12) 0.18896(11) 0.0642(3) Uani 1 1 d .
O4 O 0.29148(11) 0.39739(11) 0.17096(10) 0.0632(3) Uani 1 1 d .
C13 C 0.30383(16) 0.2530(2) 0.40607(19) 0.0741(5) Uani 1 1 d .
H13 H 0.2490 0.2152 0.3470 0.089 Uiso 1 1 calc R
C8 C 0.32265(15) 0.37108(16) 0.39589(15) 0.0616(4) Uani 1 1 d .
C9 C 0.40467(17) 0.42513(19) 0.48474(16) 0.0681(4) Uani 1 1 d .
H9 H 0.4177 0.5044 0.4800 0.082 Uiso 1 1 calc R
C10 C 0.46729(19) 0.3619(2) 0.58049(17) 0.0804(6) Uani 1 1 d .
H10 H 0.5234 0.3985 0.6393 0.097 Uiso 1 1 calc R
C7 C 0.2539(2) 0.4406(2) 0.29340(17) 0.0853(6) Uani 1 1 d .
H7A H 0.1610 0.4337 0.3002 0.102 Uiso 1 1 calc R
H7B H 0.2773 0.5214 0.3022 0.102 Uiso 1 1 calc R
C12 C 0.3659(2) 0.1913(2) 0.5032(2) 0.0808(5) Uani 1 1 d .
H12 H 0.3523 0.1123 0.5102 0.097 Uiso 1 1 calc R
C11 C 0.4472(2) 0.2464(2) 0.58897(17) 0.0809(5) Uani 1 1 d .
H11 H 0.4893 0.2045 0.6541 0.097 Uiso 1 1 calc R
O3 O 0.14954(11) 0.51959(11) 0.07648(12) 0.0694(3) Uani 1 1 d .
C6 C 0.22977(13) 0.44501(13) 0.07059(14) 0.0534(3) Uani 1 1 d .
C4 C 0.27674(15) 0.39955(13) -0.05397(15) 0.0551(3) Uani 1 1 d D
N2 N 0.29938(10) 0.27472(10) -0.05400(11) 0.0486(2) Uani 1 1 d .
N1 N 0.48973(13) 0.35012(15) -0.08979(14) 0.0660(4) Uani 1 1 d D
C2 C 0.42906(12) 0.24780(14) -0.07918(12) 0.0517(3) Uani 1 1 d .
C5 C 0.4103(2) 0.44894(17) -0.0830(3) 0.0883(7) Uani 1 1 d .
H5A H 0.4068 0.4906 -0.1633 0.106 Uiso 1 1 calc R
H5B H 0.4418 0.5004 -0.0155 0.106 Uiso 1 1 calc R
O2 O 0.47247(10) 0.15208(12) -0.09033(14) 0.0728(3) Uani 1 1 d .
C14 C 0.21670(11) 0.07206(12) -0.03434(11) 0.0450(3) Uani 1 1 d D
C3 C 0.19992(12) 0.20245(12) -0.02228(12) 0.0474(3) Uani 1 1 d .
C16 C 0.21479(13) -0.08587(13) -0.20457(12) 0.0509(3) Uani 1 1 d .
C15 C 0.19023(14) 0.03930(12) -0.17540(12) 0.0512(3) Uani 1 1 d .
H15A H 0.1007 0.0572 -0.1993 0.061 Uiso 1 1 calc R
H15B H 0.2445 0.0865 -0.2276 0.061 Uiso 1 1 calc R
C21 C 0.11822(18) -0.16729(17) -0.19769(19) 0.0699(4) Uani 1 1 d .
H21 H 0.0379 -0.1452 -0.1695 0.084 Uiso 1 1 calc R
C17 C 0.33444(17) -0.12136(17) -0.24375(18) 0.0693(4) Uani 1 1 d .
H17 H 0.4017 -0.0683 -0.2475 0.083 Uiso 1 1 calc R
C18 C 0.3548(2) -0.2348(2) -0.2773(2) 0.0905(6) Uani 1 1 d .
H18 H 0.4358 -0.2579 -0.3029 0.109 Uiso 1 1 calc R
C20 C 0.1379(2) -0.28145(18) -0.2318(3) 0.0882(6) Uani 1 1 d .
H20 H 0.0715 -0.3352 -0.2264 0.106 Uiso 1 1 calc R
C19 C 0.2557(3) -0.31415(18) -0.2732(2) 0.0899(6) Uani 1 1 d .
H19 H 0.2691 -0.3900 -0.2987 0.108 Uiso 1 1 calc R
C22 C 0.16321(11) -0.03858(11) 0.15423(12) 0.0438(2) Uani 1 1 d .
N3 N 0.12595(10) 0.01576(11) 0.04624(10) 0.0485(2) Uani 1 1 d D
C23 C 0.07229(14) -0.13738(14) 0.33597(14) 0.0550(3) Uani 1 1 d .
C24 C 0.1402(2) -0.0659(2) 0.43812(18) 0.0912(6) Uani 1 1 d .
H24A H 0.2269 -0.0496 0.4143 0.137 Uiso 1 1 calc R
H24B H 0.1429 -0.1076 0.5173 0.137 Uiso 1 1 calc R
H24C H 0.0941 0.0053 0.4481 0.137 Uiso 1 1 calc R
C25 C -0.06770(18) -0.1591(2) 0.3658(2) 0.0806(5) Uani 1 1 d .
H25A H -0.1110 -0.0866 0.3762 0.121 Uiso 1 1 calc R
H25B H -0.0710 -0.2031 0.4431 0.121 Uiso 1 1 calc R
H25C H -0.1098 -0.2013 0.2969 0.121 Uiso 1 1 calc R
C26 C 0.1408(2) -0.2506(2) 0.3128(3) 0.0909(6) Uani 1 1 d .
H26A H 0.1031 -0.2867 0.2375 0.136 Uiso 1 1 calc R
H26B H 0.1317 -0.3007 0.3848 0.136 Uiso 1 1 calc R
H26C H 0.2310 -0.2362 0.3014 0.136 Uiso 1 1 calc R
O1 O 0.09905(10) 0.24525(11) 0.00723(13) 0.0680(3) Uani 1 1 d .
H4 H 0.2114(19) 0.420(2) -0.1243(19) 0.082 Uiso 1 1 d D
H3N H 0.0419(16) 0.027(2) 0.034(2) 0.082 Uiso 1 1 d D
H1N H 0.5688(16) 0.350(2) -0.110(2) 0.082 Uiso 1 1 d D
H14 H 0.3031(17) 0.049(2) -0.006(2) 0.082 Uiso 1 1 d D
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
C22 O6 C23 120.89(10)
C6 O4 C7 114.95(12)
C12 C13 C8 120.39(17)
C9 C8 C13 118.63(17)
C9 C8 C7 119.85(19)
C13 C8 C7 121.51(17)
C10 C9 C8 120.25(19)
C11 C10 C9 120.16(18)
O4 C7 C8 108.28(14)
C11 C12 C13 119.9(2)
C10 C11 C12 120.69(19)
O3 C6 O4 124.52(14)
O3 C6 C4 123.06(14)
O4 C6 C4 112.35(12)
N2 C4 C6 113.72(13)
N2 C4 C5 102.85(14)
C6 C4 C5 111.63(13)
C3 N2 C2 129.46(12)
C3 N2 C4 118.59(11)
C2 N2 C4 111.77(12)
C2 N1 C5 115.77(13)
O2 C2 N1 128.68(13)
O2 C2 N2 125.63(13)
N1 C2 N2 105.69(14)
N1 C5 C4 103.75(14)
N3 C14 C3 108.58(11)
N3 C14 C15 111.04(11)
C3 C14 C15 107.91(10)
O1 C3 N2 118.34(13)
O1 C3 C14 122.02(12)
N2 C3 C14 119.49(11)
C21 C16 C17 118.16(16)
C21 C16 C15 121.29(13)
C17 C16 C15 120.51(14)
C16 C15 C14 114.10(11)
C16 C21 C20 121.60(17)
C18 C17 C16 120.52(18)
C19 C18 C17 120.36(18)
C19 C20 C21 119.3(2)
C20 C19 C18 119.99(19)
O5 C22 N3 124.60(11)
O5 C22 O6 125.67(12)
N3 C22 O6 109.73(10)
C22 N3 C14 122.54(10)
O6 C23 C24 109.62(14)
O6 C23 C26 110.44(14)
C24 C23 C26 112.64(19)
O6 C23 C25 101.99(12)
C24 C23 C25 111.30(17)
C26 C23 C25 110.33(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O6 C22 1.3411(14)
O6 C23 1.4713(16)
O5 C22 1.2128(16)
O4 C6 1.3262(19)
O4 C7 1.448(2)
C13 C12 1.379(3)
C13 C8 1.386(3)
C8 C9 1.381(2)
C8 C7 1.497(3)
C9 C10 1.380(3)
C10 C11 1.357(4)
C12 C11 1.361(3)
O3 C6 1.2009(18)
C6 C4 1.509(2)
C4 N2 1.4646(19)
C4 C5 1.537(2)
N2 C3 1.3781(16)
N2 C2 1.4127(17)
N1 C2 1.348(2)
N1 C5 1.412(3)
C2 O2 1.204(2)
C14 N3 1.4462(15)
C14 C3 1.526(2)
C14 C15 1.5400(18)
C3 O1 1.2075(17)
C16 C21 1.377(2)
C16 C17 1.383(2)
C16 C15 1.506(2)
C21 C20 1.387(3)
C17 C18 1.379(3)
C18 C19 1.378(4)
C20 C19 1.365(3)
C22 N3 1.3372(17)
C23 C24 1.503(3)
C23 C26 1.515(3)
C23 C25 1.515(2)
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
N2 C4 C6 O4 41.48(17)
N3 C14 C3 N2 158.72(11)
C22 N3 C14 C3 -108.51(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101496832
