#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/28/2232898.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2232898
loop_
_publ_author_name
'How, Fiona N.-F.'
'Amalina, M. S.'
'Khaledi, Hamid'
'Mohd Ali, Hapipah'
_publ_section_title
;
 4-Hydroxy-3-methoxybenzaldehyde--nicotinamide (1/1)
;
_journal_coeditor_code           PV2471
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3168
_journal_paper_doi               10.1107/S1600536811045648
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C6 H6 N2 O, C8 H8 O3'
_chemical_formula_moiety         'C6 H6 N2 O, C8 H8 O3'
_chemical_formula_sum            'C14 H14 N2 O4'
_chemical_formula_weight         274.27
_chemical_name_systematic
;
4-Hydroxy-3-methoxybenzaldehyde--nicotinamide (1/1)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_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
_cell_angle_alpha                98.1080(10)
_cell_angle_beta                 92.810(2)
_cell_angle_gamma                94.784(2)
_cell_formula_units_Z            2
_cell_length_a                   4.89790(10)
_cell_length_b                   8.5440(2)
_cell_length_c                   15.4713(4)
_cell_measurement_reflns_used    1226
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.66
_cell_measurement_theta_min      2.59
_cell_volume                     637.52(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3432
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_correction_T_min  0.9770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.278
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2243
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0447
_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)+(0.0439P)²+0.4685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1116
_reflns_number_gt                1862
_reflns_number_total             2243
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            pv2471.cif
_cod_data_source_block           I
_cod_database_code               2232898
_cod_database_fobs_code          2232898
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.3651(3) 0.83011(19) 0.61085(10) 0.0359(4) Uani d . 1 1
O O2 0.8107(3) 0.63328(16) 0.23075(9) 0.0195(3) Uani d D 1 1
H H2 0.949(4) 0.698(2) 0.2250(15) 0.029 Uiso d D 1 1
O O3 0.4028(3) 0.44026(16) 0.25734(9) 0.0218(3) Uani d . 1 1
C C1 0.3070(5) 0.7306(3) 0.54863(14) 0.0286(5) Uani d U 1 1
H H1 0.1529 0.6570 0.5522 0.034 Uiso calc R 1 1
C C2 0.4516(4) 0.7113(2) 0.46701(13) 0.0210(4) Uani d U 1 1
C C3 0.6726(4) 0.8148(2) 0.45164(13) 0.0221(5) Uani d . 1 1
H H3 0.7380 0.9016 0.4951 0.026 Uiso calc R 1 1
C C4 0.7972(4) 0.7912(2) 0.37307(13) 0.0204(4) Uani d . 1 1
H H4 0.9482 0.8620 0.3629 0.024 Uiso calc R 1 1
C C5 0.7035(4) 0.6648(2) 0.30888(12) 0.0166(4) Uani d . 1 1
C C6 0.4793(4) 0.5600(2) 0.32443(12) 0.0176(4) Uani d . 1 1
C C7 0.3561(4) 0.5847(2) 0.40255(13) 0.0208(5) Uani d . 1 1
H H7 0.2040 0.5146 0.4128 0.025 Uiso calc R 1 1
C C8 0.1709(4) 0.3323(2) 0.26827(14) 0.0217(5) Uani d . 1 1
H H8A 0.2110 0.2765 0.3179 0.033 Uiso calc R 1 1
H H8B 0.1328 0.2551 0.2150 0.033 Uiso calc R 1 1
H H8C 0.0103 0.3917 0.2793 0.033 Uiso calc R 1 1
O O4 0.8254(3) 0.71964(19) -0.04761(9) 0.0299(4) Uani d . 1 1
N N1 0.3766(4) 0.6341(2) -0.07875(11) 0.0205(4) Uani d D 1 1
H H1A 0.207(3) 0.645(3) -0.0672(14) 0.025 Uiso d D 1 1
H H1B 0.415(4) 0.586(2) -0.1293(11) 0.025 Uiso d D 1 1
N N2 0.2385(3) 0.80224(19) 0.18395(10) 0.0170(4) Uani d . 1 1
C C9 0.5840(4) 0.7129(2) -0.02755(13) 0.0197(4) Uani d . 1 1
C C10 0.5123(4) 0.7959(2) 0.05932(12) 0.0169(4) Uani d . 1 1
C C11 0.6653(4) 0.9350(2) 0.09779(13) 0.0201(4) Uani d . 1 1
H H11 0.8121 0.9801 0.0687 0.024 Uiso calc R 1 1
C C12 0.5998(4) 1.0066(2) 0.17913(13) 0.0220(5) Uani d . 1 1
H H12 0.6997 1.1023 0.2066 0.026 Uiso calc R 1 1
C C13 0.3864(4) 0.9363(2) 0.21971(13) 0.0192(4) Uani d . 1 1
H H13 0.3429 0.9856 0.2757 0.023 Uiso calc R 1 1
C C14 0.3015(4) 0.7346(2) 0.10499(12) 0.0162(4) Uani d . 1 1
H H14 0.1966 0.6397 0.0788 0.019 Uiso calc R 1 1
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
C5 O2 H2 112.6(16)
C6 O3 C8 117.44(15)
O1 C1 C2 126.2(2)
O1 C1 H1 116.9
C2 C1 H1 116.9
C3 C2 C7 119.56(18)
C3 C2 C1 122.83(19)
C7 C2 C1 117.59(19)
C4 C3 C2 119.93(19)
C4 C3 H3 120.0
C2 C3 H3 120.0
C3 C4 C5 120.68(18)
C3 C4 H4 119.7
C5 C4 H4 119.7
O2 C5 C4 124.72(18)
O2 C5 C6 115.90(17)
C4 C5 C6 119.38(18)
O3 C6 C7 125.62(18)
O3 C6 C5 114.82(17)
C7 C6 C5 119.56(18)
C6 C7 C2 120.88(19)
C6 C7 H7 119.6
C2 C7 H7 119.6
O3 C8 H8A 109.5
O3 C8 H8B 109.5
H8A C8 H8B 109.5
O3 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C9 N1 H1A 121.6(15)
C9 N1 H1B 117.5(15)
H1A N1 H1B 120(2)
C13 N2 C14 117.72(17)
O4 C9 N1 123.82(19)
O4 C9 C10 119.84(18)
N1 C9 C10 116.34(17)
C14 C10 C11 118.15(18)
C14 C10 C9 121.73(18)
C11 C10 C9 120.07(18)
C12 C11 C10 118.88(18)
C12 C11 H11 120.6
C10 C11 H11 120.6
C13 C12 C11 118.77(19)
C13 C12 H12 120.6
C11 C12 H12 120.6
N2 C13 C12 123.12(18)
N2 C13 H13 118.4
C12 C13 H13 118.4
N2 C14 C10 123.34(18)
N2 C14 H14 118.3
C10 C14 H14 118.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.197(3)
O2 C5 1.343(2)
O2 H2 0.854(16)
O3 C6 1.365(2)
O3 C8 1.435(2)
C1 C2 1.474(3)
C1 H1 0.9500
C2 C3 1.391(3)
C2 C7 1.396(3)
C3 C4 1.384(3)
C3 H3 0.9500
C4 C5 1.391(3)
C4 H4 0.9500
C5 C6 1.410(3)
C6 C7 1.375(3)
C7 H7 0.9500
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
O4 C9 1.236(2)
N1 C9 1.330(3)
N1 H1A 0.868(16)
N1 H1B 0.869(16)
N2 C13 1.336(2)
N2 C14 1.338(2)
C9 C10 1.500(3)
C10 C14 1.388(3)
C10 C11 1.392(3)
C11 C12 1.384(3)
C11 H11 0.9500
C12 C13 1.384(3)
C12 H12 0.9500
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_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O4 1_455 0.868(16) 2.048(17) 2.900(2) 167(2)
N1 H1B O2 2_665 0.869(16) 2.416(19) 3.085(2) 134.2(18)
N1 H1B O3 2_665 0.869(16) 2.203(18) 3.019(2) 156(2)
O2 H2 N2 1_655 0.854(16) 1.801(17) 2.634(2) 164(2)
C8 H8A O1 2_666 0.98 2.59 3.381(3) 137.4
C8 H8C O2 1_455 0.98 2.55 3.337(2) 137.7
C13 H13 O1 2_676 0.95 2.49 3.185(3) 129.9
loop_
_iucr_refine_instructions_details
;
TITL sad in P-1
CELL 0.71073   4.8979   8.5440  15.4713  98.108  92.810  94.784
ZERR    2.00   0.0001   0.0002   0.0004   0.001   0.002   0.002
LATT 1
SFAC C  H  N  O
UNIT 28 28  4  8
OMIT 0 0 1
OMIT -2 50.5
HTAB N1 O4_$4
HTAB N1 O2_$5
HTAB N1 O3_$5
HTAB O2 N2_$3
HTAB C8 O1_$2
HTAB C8 O2_$4
HTAB C13 O1_$1
EQIV $1 1-x,2-y,1-z
EQIV $2 1-x,1-y,1-z
EQIV $3 1+x,y,z
EQIV $4 -1+x,y,z
EQIV $5 1-x,1-y,-z
DELU 0.002 C1 C2
L.S. 12
ACTA
BOND $H
DFIX 0.84 O2 H2
DFIX 0.88 N1 H1A N1 H1B
SIZE 0.04 0.14 0.22
TEMP -173
WGHT    0.043900    0.468500
FVAR       0.19111
MOLE 1
O1    4    0.365148    0.830111    0.610855    11.00000    0.04404    0.03635 =
         0.02664    0.00057    0.00380    0.00563
O2    4    0.810731    0.633283    0.230751    11.00000    0.01820    0.02175 =
         0.01741    0.00045    0.00530   -0.00305
H2    2    0.949142    0.697852    0.224967    11.00000   -1.50000
O3    4    0.402831    0.440256    0.257342    11.00000    0.02233    0.02136 =
         0.01977   -0.00161    0.00637   -0.00450
C1    1    0.306967    0.730571    0.548633    11.00000    0.03560    0.03077 =
         0.01890   -0.00123   -0.00280    0.01038
AFIX  43
H1    2    0.152932    0.656968    0.552210    11.00000   -1.20000
AFIX   0
C2    1    0.451559    0.711345    0.467010    11.00000    0.02260    0.02463 =
         0.01697    0.00447    0.00039    0.00739
C3    1    0.672635    0.814828    0.451645    11.00000    0.02700    0.02141 =
         0.01655   -0.00202   -0.00364    0.00603
AFIX  43
H3    2    0.738020    0.901636    0.495054    11.00000   -1.20000
AFIX   0
C4    1    0.797188    0.791184    0.373069    11.00000    0.01872    0.01931 =
         0.02183    0.00138   -0.00011   -0.00175
AFIX  43
H4    2    0.948239    0.862050    0.362874    11.00000   -1.20000
AFIX   0
C5    1    0.703519    0.664759    0.308881    11.00000    0.01574    0.02087 =
         0.01452    0.00434    0.00263    0.00538
C6    1    0.479258    0.559964    0.324433    11.00000    0.01928    0.01762 =
         0.01568    0.00069    0.00024    0.00334
C7    1    0.356070    0.584664    0.402555    11.00000    0.01932    0.02423 =
         0.01992    0.00545    0.00460    0.00201
AFIX  43
H7    2    0.203963    0.514618    0.412824    11.00000   -1.20000
AFIX   0
C8    1    0.170867    0.332325    0.268266    11.00000    0.01852    0.01980 =
         0.02593    0.00213    0.00345   -0.00306
AFIX 137
H8A   2    0.211025    0.276492    0.317912    11.00000   -1.50000
H8B   2    0.132816    0.255059    0.215011    11.00000   -1.50000
H8C   2    0.010291    0.391689    0.279339    11.00000   -1.50000
AFIX   0
MOLE 2
O4    4    0.825427    0.719635   -0.047608    11.00000    0.01442    0.05164 =
         0.02284   -0.00030    0.00377    0.00639
N1    3    0.376650    0.634110   -0.078751    11.00000    0.01723    0.02789 =
         0.01526   -0.00302    0.00345    0.00456
H1A   2    0.207030    0.644898   -0.067203    11.00000   -1.20000
H1B   2    0.414547    0.585627   -0.129348    11.00000   -1.20000
N2    3    0.238477    0.802236    0.183946    11.00000    0.01709    0.01942 =
         0.01478    0.00269    0.00120    0.00309
C9    1    0.583961    0.712929   -0.027554    11.00000    0.01782    0.02550 =
         0.01682    0.00422    0.00178    0.00546
C10   1    0.512316    0.795902    0.059325    11.00000    0.01440    0.02097 =
         0.01563    0.00301   -0.00080    0.00381
C11   1    0.665263    0.935031    0.097791    11.00000    0.01493    0.02399 =
         0.02207    0.00585    0.00196    0.00033
AFIX  43
H11   2    0.812102    0.980116    0.068708    11.00000   -1.20000
AFIX   0
C12   1    0.599844    1.006608    0.179131    11.00000    0.02266    0.01797 =
         0.02335   -0.00024   -0.00108   -0.00297
AFIX  43
H12   2    0.699652    1.102265    0.206593    11.00000   -1.20000
AFIX   0
C13   1    0.386373    0.936262    0.219713    11.00000    0.02175    0.01917 =
         0.01603    0.00006    0.00022    0.00309
AFIX  43
H13   2    0.342880    0.985591    0.275665    11.00000   -1.20000
AFIX   0
C14   1    0.301506    0.734567    0.104986    11.00000    0.01567    0.01618 =
         0.01611    0.00115   -0.00129    0.00087
AFIX  43
H14   2    0.196595    0.639685    0.078839    11.00000   -1.20000
HKLF 4
REM  sad in P-1
REM R1 =  0.0447 for   1862 Fo > 4sig(Fo)  and  0.0549 for all   2243 data
REM    191 parameters refined using      4 restraints
END
WGHT      0.0430      0.4746
REM Highest difference peak  0.664,  deepest hole -0.278,  1-sigma level  0.052
Q1    1   0.1562  0.7071  0.5862  11.00000  0.05    0.66
Q2    1   0.6349  0.8310  0.0854  11.00000  0.05    0.20
Q3    1   0.4923  0.7809  0.4435  11.00000  0.05    0.19
Q4    1   0.5410  0.7580  0.0215  11.00000  0.05    0.19
;
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657269
