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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/65/4506511.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_4506511
loop_
_publ_author_name
'Zhang, Si-Wei'
'Guzei, Ilia A.'
'de Villiers, Melgardt M.'
'Yu, Lian'
'Krzyzaniak, Joseph F.'
_publ_section_title
;
 Formation Enthalpies and Polymorphs of Nicotinamide--R-Mandelic Acid
 Co-Crystals
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4090
_journal_paper_doi               10.1021/cg3005757
_journal_volume                  12
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C14 H14 N2 O4'
_chemical_formula_sum            'C14 H14 N2 O4'
_chemical_formula_weight         274.27
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 95.678(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.2406(3)
_cell_length_b                   10.0477(6)
_cell_length_c                   12.6006(7)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.60
_cell_measurement_theta_min      3.52
_cell_volume                     660.24(7)
_computing_cell_refinement       'SAINT Ver. 7.24A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 Ver. 2.1-4 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT Ver. 7.24A'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.50° ω and 0.5 ° φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7524
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         67.60
_diffrn_reflns_theta_min         3.52
_exptl_absorpt_coefficient_mu    0.857
_exptl_absorpt_correction_T_max  0.8750
_exptl_absorpt_correction_T_min  0.7953
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
SADABS  (Bruker-AXS, 2007)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.055
_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     183
_refine_ls_number_reflns         1235
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0430
_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)+(0.0800P)²+0.2704P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1174
_reflns_number_gt                1143
_reflns_number_total             1235
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg3005757_si_002.cif
_cod_data_source_block           yu04
_cod_original_sg_symbol_Hall     'P 2yb       '
_cod_original_sg_symbol_H-M      'P 1 21 1    '
_cod_database_code               4506511
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
O1 O 0.2081(5) 0.4587(3) 0.5454(2) 0.0295(6) Uani 1 1 d .
N1 N 0.2106(6) 0.2357(3) 0.5223(2) 0.0251(7) Uani 1 1 d .
H1A H 0.1124 0.2221 0.5741 0.030 Uiso 1 1 calc R
H1B H 0.2646 0.1678 0.4866 0.030 Uiso 1 1 calc R
N2 N 0.5641(6) 0.5243(3) 0.2736(2) 0.0268(7) Uani 1 1 d .
C1 C 0.2773(7) 0.3588(4) 0.4983(3) 0.0232(8) Uani 1 1 d .
C2 C 0.4465(7) 0.3754(3) 0.4097(3) 0.0237(8) Uani 1 1 d .
C3 C 0.4226(7) 0.4946(4) 0.3528(3) 0.0253(8) Uani 1 1 d .
H3 H 0.2995 0.5577 0.3713 0.030 Uiso 1 1 calc R
C4 C 0.7377(7) 0.4343(4) 0.2488(3) 0.0269(8) Uani 1 1 d .
H4 H 0.8393 0.4539 0.1923 0.032 Uiso 1 1 calc R
C5 C 0.7757(7) 0.3137(4) 0.3018(3) 0.0265(8) Uani 1 1 d .
H5 H 0.9030 0.2533 0.2828 0.032 Uiso 1 1 calc R
C6 C 0.6253(7) 0.2826(4) 0.3829(3) 0.0248(8) Uani 1 1 d .
H6 H 0.6443 0.1998 0.4193 0.030 Uiso 1 1 calc R
O2 O 0.8192(5) 0.2755(3) 0.6779(2) 0.0293(6) Uani 1 1 d .
O3 O 0.4861(5) 0.2833(3) 0.7762(2) 0.0271(6) Uani 1 1 d .
H3A H 0.4804 0.2011 0.7641 0.041 Uiso 1 1 calc R
O4 O 0.8132(5) 0.5426(3) 0.6517(2) 0.0277(6) Uani 1 1 d .
H4A H 0.9188 0.4860 0.6338 0.041 Uiso 1 1 calc R
C7 C 0.6671(7) 0.3375(4) 0.7255(3) 0.0227(8) Uani 1 1 d .
C8 C 0.6728(7) 0.4884(4) 0.7317(3) 0.0262(8) Uani 1 1 d .
H8 H 0.4923 0.5212 0.7187 0.031 Uiso 1 1 calc R
C9 C 0.7803(7) 0.5349(4) 0.8424(3) 0.0241(8) Uani 1 1 d .
C10 C 1.0115(8) 0.4864(4) 0.8902(3) 0.0322(9) Uani 1 1 d .
H10 H 1.1029 0.4216 0.8542 0.039 Uiso 1 1 calc R
C11 C 1.1110(8) 0.5314(4) 0.9900(3) 0.0372(10) Uani 1 1 d .
H11 H 1.2670 0.4957 1.0229 0.045 Uiso 1 1 calc R
C12 C 0.9806(9) 0.6297(4) 1.0417(3) 0.0379(10) Uani 1 1 d .
H12 H 1.0497 0.6634 1.1089 0.046 Uiso 1 1 calc R
C13 C 0.7517(9) 0.6770(4) 0.9942(3) 0.0376(10) Uani 1 1 d .
H13 H 0.6610 0.7423 1.0300 0.045 Uiso 1 1 calc R
C14 C 0.6501(8) 0.6314(4) 0.8954(3) 0.0322(9) Uani 1 1 d .
H14 H 0.4918 0.6659 0.8637 0.039 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
C1 N1 H1A 120.0
C1 N1 H1B 120.0
H1A N1 H1B 120.0
C3 N2 C4 117.6(3)
O1 C1 N1 123.3(3)
O1 C1 C2 119.2(3)
N1 C1 C2 117.4(3)
C6 C2 C3 118.7(3)
C6 C2 C1 124.7(3)
C3 C2 C1 116.6(3)
N2 C3 C2 123.2(3)
N2 C3 H3 118.4
C2 C3 H3 118.4
N2 C4 C5 123.0(3)
N2 C4 H4 118.5
C5 C4 H4 118.5
C6 C5 C4 119.1(3)
C6 C5 H5 120.4
C4 C5 H5 120.4
C5 C6 C2 118.3(3)
C5 C6 H6 120.8
C2 C6 H6 120.8
C7 O3 H3A 109.5
C8 O4 H4A 109.5
O2 C7 O3 124.6(4)
O2 C7 C8 121.8(3)
O3 C7 C8 113.6(3)
O4 C8 C7 110.9(3)
O4 C8 C9 111.3(3)
C7 C8 C9 110.9(3)
O4 C8 H8 107.9
C7 C8 H8 107.9
C9 C8 H8 107.9
C10 C9 C14 119.0(4)
C10 C9 C8 121.2(3)
C14 C9 C8 119.8(3)
C9 C10 C11 120.8(4)
C9 C10 H10 119.6
C11 C10 H10 119.6
C10 C11 C12 119.7(4)
C10 C11 H11 120.2
C12 C11 H11 120.2
C13 C12 C11 119.2(4)
C13 C12 H12 120.4
C11 C12 H12 120.4
C12 C13 C14 121.4(4)
C12 C13 H13 119.3
C14 C13 H13 119.3
C13 C14 C9 119.9(4)
C13 C14 H14 120.1
C9 C14 H14 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.239(4) yes
N1 C1 1.327(5) ?
N1 H1A 0.8800 ?
N1 H1B 0.8800 ?
N2 C3 1.335(5) ?
N2 C4 1.341(5) ?
C1 C2 1.503(5) ?
C2 C6 1.387(5) ?
C2 C3 1.395(5) ?
C3 H3 0.9500 ?
C4 C5 1.389(6) ?
C4 H4 0.9500 ?
C5 C6 1.387(5) ?
C5 H5 0.9500 ?
C6 H6 0.9500 ?
O2 C7 1.216(4) yes
O3 C7 1.313(4) yes
O3 H3A 0.8400 ?
O4 C8 1.415(4) yes
O4 H4A 0.8400 ?
C7 C8 1.519(5) ?
C8 C9 1.525(5) ?
C8 H8 1.0000 ?
C9 C10 1.387(5) ?
C9 C14 1.394(5) ?
C10 C11 1.388(6) ?
C10 H10 0.9500 ?
C11 C12 1.398(6) ?
C11 H11 0.9500 ?
C12 C13 1.371(7) ?
C12 H12 0.9500 ?
C13 C14 1.383(6) ?
C13 H13 0.9500 ?
C14 H14 0.9500 ?
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
N1 H1A O2 0.88 2.18 3.000(4) 154.7 1_455
N1 H1B O4 0.88 2.15 2.921(4) 145.3 2_646
O3 H3A N2 0.84 1.85 2.684(4) 173.5 2_646
O4 H4A O1 0.84 1.99 2.708(4) 143.4 1_655
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
O1 C1 C2 C6 149.8(4)
N1 C1 C2 C6 -29.8(5)
O1 C1 C2 C3 -28.8(5)
N1 C1 C2 C3 151.6(3)
C4 N2 C3 C2 -0.3(5)
C6 C2 C3 N2 -0.2(5)
C1 C2 C3 N2 178.5(3)
C3 N2 C4 C5 -0.3(5)
N2 C4 C5 C6 1.3(5)
C4 C5 C6 C2 -1.6(5)
C3 C2 C6 C5 1.1(5)
C1 C2 C6 C5 -177.5(3)
O2 C7 C8 O4 18.1(5)
O3 C7 C8 O4 -162.2(3)
O2 C7 C8 C9 -106.1(4)
O3 C7 C8 C9 73.6(4)
O4 C8 C9 C10 -72.7(4)
C7 C8 C9 C10 51.2(5)
O4 C8 C9 C14 104.8(4)
C7 C8 C9 C14 -131.2(4)
C14 C9 C10 C11 0.9(6)
C8 C9 C10 C11 178.5(4)
C9 C10 C11 C12 -1.9(6)
C10 C11 C12 C13 2.1(6)
C11 C12 C13 C14 -1.4(6)
C12 C13 C14 C9 0.4(6)
C10 C9 C14 C13 -0.2(6)
C8 C9 C14 C13 -177.8(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146134
