#------------------------------------------------------------------------------
#$Date: 2020-04-16 06:19:22 +0300 (Thu, 16 Apr 2020) $
#$Revision: 250831 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240319.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_7240319
loop_
_publ_author_name
'Scowen, Ian J.'
'Alomar, Taghrid Saad'
'Munshi, Tasnim'
'Seaton, Colin Cormack'
_publ_section_title
;
 Invitation to Submit: The Cambridge Structural Database Structural
 Similarity in Chiral-Achiral Multi-Component Crystals
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00301H
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_sum            'C16 H18 N4 O7'
_chemical_formula_weight         378.34
_chemical_name_common
;
L-malic acid nicotinamide
;
_chemical_name_systematic
; 
 (R)-2-hydroxysuccinic acid nicotinamide 
;
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2020-02-28 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                96.829(3)
_cell_angle_beta                 95.279(3)
_cell_angle_gamma                105.603(3)
_cell_formula_units_Z            1
_cell_length_a                   4.7631(2)
_cell_length_b                   8.8253(4)
_cell_length_c                   10.6620(5)
_cell_measurement_reflns_used    2766
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.33
_cell_measurement_theta_min      2.42
_cell_volume                     424.99(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.930
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0135
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7290
_diffrn_reflns_theta_full        32.00
_diffrn_reflns_theta_max         32.00
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7630
_exptl_absorpt_correction_T_min  0.7120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS - Bruker AXS, Madison WI'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             198
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.8(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4822
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0488P)²+0.0293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0919
_reflns_number_gt                3952
_reflns_number_total             4822
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ce00301h2.cif
_cod_data_source_block           tai_23_3b_2_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      P1
_cod_database_code               7240319
loop_
_symmetry_equiv_pos_as_xyz
'x, y, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.1666(4) 0.4681(2) 0.72139(16) 0.0216(4) Uani 1 1 d . . .
C2A C -0.0768(4) 0.3865(2) 0.79272(18) 0.0230(4) Uani 1 1 d . . .
C3A C 0.0485(4) 0.3156(2) 0.90122(18) 0.0233(4) Uani 1 1 d . . .
C4A C -0.2008(4) 0.2188(2) 0.96529(17) 0.0197(3) Uani 1 1 d . . .
O3A O 0.2443(3) 0.43750(19) 0.99183(15) 0.0419(4) Uani 1 1 d . . .
O11A O 0.2789(3) 0.62058(15) 0.75973(13) 0.0276(3) Uani 1 1 d . . .
O12A O 0.2547(3) 0.39399(15) 0.63790(13) 0.0348(3) Uani 1 1 d . . .
O41A O -0.3719(3) 0.09341(15) 0.89882(12) 0.0280(3) Uani 1 1 d . . .
O42A O -0.2151(3) 0.26782(15) 1.07717(12) 0.0288(3) Uani 1 1 d . . .
H21A H -0.181(5) 0.465(3) 0.830(2) 0.027(6) Uiso 1 1 d . . .
H22A H -0.215(5) 0.300(3) 0.732(2) 0.041(7) Uiso 1 1 d . . .
H31A H 0.161(5) 0.245(2) 0.8654(19) 0.021(5) Uiso 1 1 d . . .
H3AO H 0.158(6) 0.431(3) 1.059(3) 0.059(8) Uiso 1 1 d . . .
C1B C 0.9067(4) 0.8875(2) 0.67159(19) 0.0260(4) Uani 1 1 d . . .
C2B C 1.1382(5) 0.9435(2) 0.6049(2) 0.0282(4) Uani 1 1 d . . .
C3B C 1.1739(4) 0.8483(2) 0.49756(18) 0.0234(4) Uani 1 1 d . . .
C4B C 0.9729(4) 0.7000(2) 0.46021(16) 0.0191(3) Uani 1 1 d . . .
C5B C 0.7496(4) 0.6506(2) 0.53478(17) 0.0209(4) Uani 1 1 d . . .
C6B C 0.9986(4) 0.5944(2) 0.34285(17) 0.0205(3) Uani 1 1 d . . .
O1B O 1.2391(3) 0.60440(17) 0.30486(13) 0.0301(3) Uani 1 1 d . . .
N1B N 0.7179(3) 0.74203(18) 0.63827(14) 0.0224(3) Uani 1 1 d . . .
N2B N 0.7487(4) 0.4922(2) 0.28407(16) 0.0262(4) Uani 1 1 d . . .
H1B H 0.874(5) 0.945(3) 0.744(2) 0.028(6) Uiso 1 1 d . . .
H2B H 1.276(5) 1.045(3) 0.630(2) 0.030(6) Uiso 1 1 d . . .
H3B H 1.342(5) 0.885(3) 0.448(2) 0.023(5) Uiso 1 1 d . . .
H5B H 0.614(5) 0.540(3) 0.516(2) 0.035(6) Uiso 1 1 d . . .
H21B H 0.573(5) 0.497(3) 0.301(2) 0.022(5) Uiso 1 1 d . . .
H22B H 0.763(5) 0.432(3) 0.216(2) 0.029(6) Uiso 1 1 d . . .
C1C C -0.9611(4) -0.1846(2) 0.99043(18) 0.0233(4) Uani 1 1 d . . .
C2C C -1.1894(4) -0.2457(2) 1.05709(18) 0.0252(4) Uani 1 1 d . . .
C3C C -1.2274(4) -0.1534(2) 1.16557(17) 0.0216(4) Uani 1 1 d . . .
C4C C -1.0306(3) -0.0041(2) 1.20742(16) 0.0176(3) Uani 1 1 d . . .
C5C C -0.8061(4) 0.0509(2) 1.13587(16) 0.0178(3) Uani 1 1 d . . .
C6C C -1.0697(4) 0.0983(2) 1.32357(16) 0.0195(3) Uani 1 1 d . . .
O1C O -1.3194(3) 0.08488(17) 1.35349(13) 0.0268(3) Uani 1 1 d . . .
N1C N -0.7768(3) -0.03842(17) 1.02970(14) 0.0198(3) Uani 1 1 d . . .
N2C N -0.8278(4) 0.20127(19) 1.38788(16) 0.0240(3) Uani 1 1 d . . .
H1C H -0.917(4) -0.244(3) 0.915(2) 0.023(5) Uiso 1 1 d . . .
H2C H -1.317(5) -0.349(3) 1.026(2) 0.037(7) Uiso 1 1 d . . .
H3C H 0.615(5) 0.803(3) 0.213(2) 0.026(6) Uiso 1 1 d . . .
H5C H -0.670(4) 0.148(2) 1.1575(18) 0.011(4) Uiso 1 1 d . . .
H21C H -0.668(5) 0.189(3) 1.373(2) 0.025(6) Uiso 1 1 d . . .
H22C H -0.841(6) 0.257(4) 1.461(3) 0.048(8) Uiso 1 1 d . . .
H11O H 0.4395 0.6676 0.7178 0.041(10) Uiso 0.70 1 d P A 1
H1BN H 0.5695 0.7129 0.6780 0.03(2) Uiso 0.30 1 d P B 2
H1CN H -0.6500 -0.0046 0.9895 0.018(7) Uiso 0.70 1 d P C 1
H41O H -0.5186 0.0292 0.9576 0.008(14) Uiso 0.30 1 d P D 2
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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12A C1A O11A 123.50(17) . . ?
O12A C1A C2A 121.43(16) . . ?
O11A C1A C2A 115.02(15) . . ?
C1A C2A C3A 110.18(14) . . ?
C1A C2A H21A 110.7(13) . . ?
C3A C2A H21A 108.9(12) . . ?
C1A C2A H22A 107.2(14) . . ?
C3A C2A H22A 109.2(14) . . ?
H21A C2A H22A 110.7(18) . . ?
O3A C3A C2A 110.44(14) . . ?
O3A C3A C4A 110.23(15) . . ?
C2A C3A C4A 110.28(13) . . ?
O3A C3A H31A 107.9(12) . . ?
C2A C3A H31A 108.5(11) . . ?
C4A C3A H31A 109.4(12) . . ?
O42A C4A O41A 125.75(16) . . ?
O42A C4A C3A 117.37(15) . . ?
O41A C4A C3A 116.88(15) . . ?
C3A O3A H3AO 103.0(19) . . ?
C1A O11A H11O 113.52(14) . . ?
C4A O41A H41O 109.54(13) . . ?
N1B C1B C2B 122.17(19) . . ?
N1B C1B H1B 114.5(14) . . ?
C2B C1B H1B 123.2(14) . . ?
C1B C2B C3B 119.28(19) . . ?
C1B C2B H2B 122.2(14) . . ?
C3B C2B H2B 118.6(14) . . ?
C4B C3B C2B 118.71(18) . . ?
C4B C3B H3B 120.1(13) . . ?
C2B C3B H3B 121.2(13) . . ?
C3B C4B C5B 118.42(16) . . ?
C3B C4B C6B 120.57(16) . . ?
C5B C4B C6B 121.01(16) . . ?
N1B C5B C4B 122.56(17) . . ?
N1B C5B H5B 116.6(14) . . ?
C4B C5B H5B 120.7(14) . . ?
O1B C6B N2B 123.11(18) . . ?
O1B C6B C4B 120.91(16) . . ?
N2B C6B C4B 115.98(16) . . ?
C5B N1B C1B 118.80(16) . . ?
C5B N1B H1BN 120.69(17) . . ?
C1B N1B H1BN 120.17(17) . . ?
C6B N2B H21B 123.2(14) . . ?
C6B N2B H22B 115.9(16) . . ?
H21B N2B H22B 120(2) . . ?
N1C C1C C2C 120.73(17) . . ?
N1C C1C H1C 115.7(13) . . ?
C2C C1C H1C 123.5(13) . . ?
C1C C2C C3C 118.92(17) . . ?
C1C C2C H2C 118.2(15) . . ?
C3C C2C H2C 122.8(15) . . ?
C4C C3C C2C 119.88(17) . . ?
C3C C4C C5C 118.38(16) . . ?
C3C C4C C6C 120.71(15) . . ?
C5C C4C C6C 120.84(15) . . ?
N1C C5C C4C 120.90(16) . . ?
N1C C5C H5C 116.2(12) . . ?
C4C C5C H5C 122.9(12) . . ?
O1C C6C N2C 123.78(18) . . ?
O1C C6C C4C 119.57(17) . . ?
N2C C6C C4C 116.64(16) . . ?
C5C N1C C1C 121.14(16) . . ?
C5C N1C H1CN 119.51(17) . . ?
C1C N1C H1CN 119.35(17) . . ?
C6C N2C H21C 117.8(15) . . ?
C6C N2C H22C 118.8(19) . . ?
H21C N2C H22C 120(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A O12A 1.214(2) . ?
C1A O11A 1.306(2) . ?
C1A C2A 1.511(3) . ?
C2A C3A 1.527(2) . ?
C2A H21A 1.02(2) . ?
C2A H22A 0.98(3) . ?
C3A O3A 1.417(2) . ?
C3A C4A 1.532(2) . ?
C3A H31A 0.99(2) . ?
C4A O42A 1.234(2) . ?
C4A O41A 1.270(2) . ?
O3A H3AO 0.86(3) . ?
O11A H11O 0.9453(13) . ?
O41A H41O 1.0742(12) . ?
C1B N1B 1.340(2) . ?
C1B C2B 1.379(3) . ?
C1B H1B 0.92(2) . ?
C2B C3B 1.388(3) . ?
C2B H2B 0.95(2) . ?
C3B C4B 1.386(2) . ?
C3B H3B 1.00(2) . ?
C4B C5B 1.394(2) . ?
C4B C6B 1.503(2) . ?
C5B N1B 1.333(2) . ?
C5B H5B 1.00(3) . ?
C6B O1B 1.235(2) . ?
C6B N2B 1.332(3) . ?
N1B H1BN 0.8534(15) . ?
N2B H21B 0.89(2) . ?
N2B H22B 0.86(3) . ?
C1C N1C 1.344(2) . ?
C1C C2C 1.377(3) . ?
C1C H1C 0.98(2) . ?
C2C C3C 1.389(3) . ?
C2C H2C 0.95(3) . ?
C3C C4C 1.390(2) . ?
C4C C5C 1.385(2) . ?
C4C C6C 1.500(2) . ?
C5C N1C 1.341(2) . ?
C5C H5C 0.92(2) . ?
C6C O1C 1.239(2) . ?
C6C N2C 1.329(2) . ?
N1C H1CN 0.7866(14) . ?
N2C H21C 0.83(2) . ?
N2C H22C 0.88(3) . ?
