#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/81/4508142.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_4508142
loop_
_publ_author_name
'Lemmerer, Andreas'
'Adsmond, Daniel A.'
'Esterhuysen, Catharine'
'Bernstein, Joel'
_publ_section_title
;
 Polymorphic Co-crystals from Polymorphic Co-crystal Formers: Competition
 between Carboxylic Acid...Pyridine and Phenol...Pyridine Hydrogen Bonds
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3935
_journal_paper_doi               10.1021/cg4006357
_journal_volume                  13
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C7 H12 O4, C6 H6 N2 O'
_chemical_formula_sum            'C13 H18 N2 O5'
_chemical_formula_weight         282.29
_chemical_name_systematic
;
 (nicotinamide).(pimelic acid) Form II
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2009-03-11T11:15:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.838(3)
_cell_length_b                   31.514(8)
_cell_length_c                   5.252(2)
_cell_measurement_reflns_used    781
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.18
_cell_measurement_theta_min      2.33
_cell_volume                     1462.8(8)
_computing_cell_refinement       'Bruker SAINT+, Bruker (1999)'
_computing_data_collection       'Bruker SMART, Bruker (1998)'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0998
_diffrn_reflns_av_unetI/netI     0.1082
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7309
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.39
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.9514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.06
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1525
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1857
_refine_ls_R_factor_gt           0.0909
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1530P)²+1.2057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2345
_refine_ls_wR_factor_ref         0.3072
_reflns_number_gt                725
_reflns_number_total             1525
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg4006357_si_002.cif
_cod_data_source_block           6(II)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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        1462.7(8)
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               4508142
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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
C1 C 0.6090(16) 0.3726(4) 0.151(3) 0.101(4) Uani 1 1 d DU
C2 C 0.6233(18) 0.4045(4) -0.061(3) 0.127(4) Uani 1 1 d DU
H2A H 0.6862 0.3928 -0.1956 0.153 Uiso 1 1 calc R
H2B H 0.5241 0.4103 -0.1322 0.153 Uiso 1 1 calc R
C3 C 0.6880(19) 0.4426(4) 0.029(3) 0.141(5) Uani 1 1 d DU
H3A H 0.7846 0.4362 0.1073 0.169 Uiso 1 1 calc R
H3B H 0.6227 0.4544 0.1593 0.169 Uiso 1 1 calc R
C4 C 0.7124(15) 0.4763(3) -0.180(3) 0.113(4) Uani 1 1 d DU
H4A H 0.7753 0.4646 -0.3141 0.135 Uiso 1 1 calc R
H4B H 0.6157 0.484 -0.2541 0.135 Uiso 1 1 calc R
C5 C 0.7861(15) 0.5148(3) -0.074(3) 0.102(4) Uani 1 1 d DU
H5A H 0.8806 0.5064 0.0052 0.122 Uiso 1 1 calc R
H5B H 0.7216 0.5262 0.0593 0.122 Uiso 1 1 calc R
C6 C 0.8190(13) 0.5499(3) -0.261(2) 0.080(3) Uani 1 1 d DU
H6A H 0.8836 0.5389 -0.3953 0.096 Uiso 1 1 calc R
H6B H 0.7248 0.559 -0.3391 0.096 Uiso 1 1 calc R
C7 C 0.8942(12) 0.5875(3) -0.142(2) 0.075(3) Uani 1 1 d DU
O1 O 0.4996(11) 0.3822(2) 0.316(2) 0.109(3) Uani 1 1 d U
H1 H 0.4729 0.3607 0.3908 0.163 Uiso 1 1 calc R
O2 O 0.6742(9) 0.3396(3) 0.1466(18) 0.098(3) Uani 1 1 d U
O3 O 0.8939(9) 0.6206(2) -0.2904(16) 0.086(2) Uani 1 1 d U
H3 H 0.944 0.6396 -0.2249 0.129 Uiso 1 1 calc R
O4 O 0.9516(14) 0.5883(3) 0.0647(19) 0.135(4) Uani 1 1 d U
C8 C 0.3938(10) 0.2418(3) 0.674(2) 0.057(2) Uani 1 1 d .
C9 C 0.4485(11) 0.2759(3) 0.538(2) 0.066(3) Uani 1 1 d .
H9 H 0.5123 0.2706 0.4009 0.079 Uiso 1 1 calc R
C10 C 0.3226(11) 0.3236(4) 0.795(2) 0.073(3) Uani 1 1 d .
H10 H 0.2984 0.3513 0.8386 0.088 Uiso 1 1 calc R
C11 C 0.2636(11) 0.2914(3) 0.937(2) 0.074(3) Uani 1 1 d .
H11 H 0.1989 0.2975 1.0717 0.089 Uiso 1 1 calc R
C12 C 0.3004(11) 0.2497(3) 0.880(2) 0.069(3) Uani 1 1 d .
H12 H 0.2631 0.2275 0.9786 0.083 Uiso 1 1 calc R
C13 C 0.4407(11) 0.1983(3) 0.592(2) 0.065(3) Uani 1 1 d .
N1 N 0.4042(10) 0.1658(3) 0.7444(18) 0.081(3) Uani 1 1 d .
H1S H 0.4303 0.1404 0.7039 0.121 Uiso 1 1 calc R
H1A H 0.3546 0.1704 0.8827 0.121 Uiso 1 1 calc R
N2 N 0.4138(9) 0.3169(2) 0.5949(17) 0.066(2) Uani 1 1 d .
O5 O 0.5120(8) 0.1930(2) 0.3914(15) 0.078(2) Uani 1 1 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.02
0 1 0 0.02
-1 0 0 0.18
1 0 0 0.18
0 0 -1 0.2
0 0 1 0.2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 C1 O1 124.4(11)
O2 C1 C2 121.8(13)
O1 C1 C2 112.9(11)
C3 C2 C1 110.7(14)
C3 C2 H2A 109.5
C1 C2 H2A 109.5
C3 C2 H2B 109.5
C1 C2 H2B 109.5
H2A C2 H2B 108.1
C2 C3 C4 113.9(14)
C2 C3 H3A 108.8
C4 C3 H3A 108.8
C2 C3 H3B 108.8
C4 C3 H3B 108.8
H3A C3 H3B 107.7
C5 C4 C3 110.9(12)
C5 C4 H4A 109.5
C3 C4 H4A 109.5
C5 C4 H4B 109.5
C3 C4 H4B 109.5
H4A C4 H4B 108
C4 C5 C6 115.9(12)
C4 C5 H5A 108.3
C6 C5 H5A 108.3
C4 C5 H5B 108.3
C6 C5 H5B 108.3
H5A C5 H5B 107.4
C7 C6 C5 113.1(10)
C7 C6 H6A 108.9
C5 C6 H6A 108.9
C7 C6 H6B 108.9
C5 C6 H6B 108.9
H6A C6 H6B 107.8
O4 C7 O3 121.6(10)
O4 C7 C6 125.8(10)
O3 C7 C6 112.7(9)
C1 O1 H1 109.5
C7 O3 H3 109.5
C9 C8 C12 118.3(9)
C9 C8 C13 118.0(8)
C12 C8 C13 123.7(9)
N2 C9 C8 123.3(9)
N2 C9 H9 118.4
C8 C9 H9 118.4
N2 C10 C11 123.0(10)
N2 C10 H10 118.5
C11 C10 H10 118.5
C10 C11 C12 119.9(10)
C10 C11 H11 120.1
C12 C11 H11 120.1
C8 C12 C11 118.5(10)
C8 C12 H12 120.7
C11 C12 H12 120.7
O5 C13 N1 121.7(9)
O5 C13 C8 120.7(9)
N1 C13 C8 117.6(9)
C13 N1 H1A 120
C13 N1 H1S 120
H1A N1 H1S 120
C10 N2 C9 117.0(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.187(13)
C1 O1 1.331(14)
C1 C2 1.508(14)
C2 C3 1.412(14)
C2 H2A 0.97
C2 H2B 0.97
C3 C4 1.543(14)
C3 H3A 0.97
C3 H3B 0.97
C4 C5 1.485(13)
C4 H4A 0.97
C4 H4B 0.97
C5 C6 1.509(12)
C5 H5A 0.97
C5 H5B 0.97
C6 C7 1.494(12)
C6 H6A 0.97
C6 H6B 0.97
C7 O4 1.200(13)
C7 O3 1.303(12)
O1 H1 0.82
O3 H3 0.82
C8 C9 1.377(13)
C8 C12 1.385(13)
C8 C13 1.494(13)
C9 N2 1.363(12)
C9 H9 0.93
C10 N2 1.341(13)
C10 C11 1.361(15)
C10 H10 0.93
C11 C12 1.388(14)
C11 H11 0.93
C12 H12 0.93
C13 O5 1.240(12)
C13 N1 1.339(13)
N1 H1A 0.86
N1 H1S 0.86
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 N2 0.82 1.82 2.637(11) 173 .
O3 H3 O5 0.82 1.83 2.607(10) 158 4_654
N1 H1S O4 0.86 2.08 2.912(12) 163 4_645
N1 H1A O2 0.86 2.14 2.936(11) 155 3_456
C11 H11 O5 0.93 2.37 3.299(13) 173 3_456
C12 H12 O2 0.93 2.42 3.335(13) 167 3_456
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
O2 C1 C2 C3 -117.6(17)
O1 C1 C2 C3 72.8(18)
C1 C2 C3 C4 177.7(14)
C2 C3 C4 C5 -177.8(13)
C3 C4 C5 C6 178.8(13)
C4 C5 C6 C7 -179.5(11)
C5 C6 C7 O4 14.2(19)
C5 C6 C7 O3 -166.6(11)
C12 C8 C9 N2 -0.8(14)
C13 C8 C9 N2 -179.9(10)
N2 C10 C11 C12 1.5(18)
C9 C8 C12 C11 1.4(14)
C13 C8 C12 C11 -179.5(11)
C10 C11 C12 C8 -1.8(16)
C9 C8 C13 O5 -8.2(15)
C12 C8 C13 O5 172.8(10)
C9 C8 C13 N1 171.1(10)
C12 C8 C13 N1 -7.9(15)
C11 C10 N2 C9 -0.8(16)
C8 C9 N2 C10 0.5(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146595
