#------------------------------------------------------------------------------
#$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/20/2012089.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_2012089
loop_
_publ_author_name
'O'Leary, Jane'
'Wallis, John D.'
'Wood, Michael L.'
_publ_section_title
;
 1,6-Interactions between dimethylamino and aldehyde groups in two
 biphenyl derivatives
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              851
_journal_page_last               853
_journal_paper_doi               10.1107/S0108270101006369
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C15 H15 N O'
_chemical_formula_sum            'C15 H15 N O'
_chemical_formula_weight         225.28
_chemical_melting_point          .348E-305
_chemical_name_systematic
;
 2-(N,N-Dimethylamino)-biphenyl-2'-carboxaldehyde
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 101.890(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.169(2)
_cell_length_b                   11.042(3)
_cell_length_c                   13.745(4)
_cell_measurement_reflns_used    2931
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     1213.2(6)
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_collection
'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics    'ORTEPIII (Johnson & Burnett, 1996)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  Kappa-CCD
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0425
_diffrn_reflns_av_sigmaI/netI    .0363
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12528
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.0
_exptl_absorpt_coefficient_mu    .077
_exptl_absorpt_correction_T_max  .983
_exptl_absorpt_correction_T_min  .906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SORTAV (Blessing, 1995)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .40
_exptl_crystal_size_min          .25
_refine_diff_density_max         .23
_refine_diff_density_min         -.38
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_all          .067
_refine_ls_R_factor_gt           .051
_refine_ls_shift/su_max          .008
_refine_ls_shift/su_mean         .002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0776P)^2^+0.0677P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .126
_reflns_number_gt                2211
_reflns_number_total             2783
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gg1051.cif
_cod_data_source_block           VI
_cod_original_cell_volume        1213.1(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2012089
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 .42227(14) .12485(9) .06615(7) .0439(3) Uani d . 1 . . O
C7 .56425(14) .05279(10) .32747(9) .0213(3) Uani d . 1 . . C
C8 .54862(14) .04338(10) .22396(8) .0210(3) Uani d . 1 . . C
C9 .63454(14) -.04752(11) .18415(9) .0244(3) Uani d . 1 . . C
C10 .73601(15) -.12794(11) .24583(10) .0278(3) Uani d . 1 . . C
C11 .75298(16) -.11882(11) .34807(10) .0292(3) Uani d . 1 . . C
C12 .66787(15) -.02939(11) .38835(9) .0262(3) Uani d . 1 . . C
C15 .44751(15) .13117(11) .15572(9) .0246(3) Uani d . 1 . . C
N1 .20131(12) .07866(9) .28372(7) .0241(3) Uani d . 1 . . N
C1 .47517(15) .14762(10) .37424(9) .0218(3) Uani d . 1 . . C
C2 .29921(15) .15933(10) .35281(8) .0217(3) Uani d . 1 . . C
C3 .22753(17) .25411(11) .39690(9) .0281(3) Uani d . 1 . . C
C4 .32549(19) .33511(11) .46071(10) .0330(3) Uani d . 1 . . C
C5 .49737(18) .32245(12) .48333(10) .0326(3) Uani d . 1 . . C
C6 .57074(16) .22835(11) .44111(9) .0271(3) Uani d . 1 . . C
C13 .20425(17) -.04795(11) .31544(11) .0288(3) Uani d . 1 . . C
C14 .03054(16) .11710(13) .24248(11) .0324(3) Uani d . 1 . . C
H9 .6203(18) -.0522(13) .1141(12) .035(4) Uiso d . 1 . . H
H10 .7969(18) -.1918(14) .2204(11) .036(4) Uiso d . 1 . . H
H11 .8247(18) -.1752(13) .3923(11) .032(4) Uiso d . 1 . . H
H12 .6787(18) -.0250(13) .4609(12) .037(4) Uiso d . 1 . . H
H15 .4016(17) .2026(13) .1863(10) .029(3) Uiso d . 1 . . H
H3 .1049(19) .2629(12) .3822(10) .031(4) Uiso d . 1 . . H
H4 .2765(19) .4009(16) .4897(11) .045(4) Uiso d . 1 . . H
H5 .5685(18) .3803(13) .5287(11) .035(4) Uiso d . 1 . . H
H6 .6931(19) .2189(12) .4568(10) .028(3) Uiso d . 1 . . H
H13X .318(2) -.0761(14) .3438(11) .036(4) Uiso d . 1 . . H
H13Y .1528(17) -.0961(13) .2544(11) .033(4) Uiso d . 1 . . H
H13Z .1321(19) -.0627(13) .3654(11) .035(4) Uiso d . 1 . . H
H14X -.0182(18) .0609(14) .1853(11) .039(4) Uiso d . 1 . . H
H14Y -.0441(18) .1154(12) .2947(11) .033(4) Uiso d . 1 . . H
H14Z .0307(17) .1988(13) .2156(10) .032(4) Uiso d . 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 .0557(7) .0523(6) .0205(5) .0163(5) .0005(5) -.0001(4)
C7 .0190(5) .0223(6) .0233(6) -.0038(4) .0057(5) -.0005(4)
C8 .0189(5) .0219(5) .0222(6) -.0043(4) .0041(5) -.0013(4)
C9 .0239(6) .0267(6) .0234(7) -.0055(5) .0067(5) -.0042(5)
C10 .0243(6) .0247(6) .0365(8) .0014(5) .0111(5) -.0028(5)
C11 .0246(6) .0289(7) .0346(7) .0038(5) .0073(5) .0074(5)
C12 .0253(6) .0309(6) .0226(6) .0008(5) .0053(5) .0028(5)
C15 .0260(6) .0253(6) .0227(7) -.0022(5) .0050(5) -.0006(5)
N1 .0227(5) .0242(5) .0249(5) -.0013(4) .0037(4) .0005(4)
C1 .0269(6) .0215(5) .0179(6) -.0011(5) .0064(5) .0022(4)
C2 .0266(6) .0206(5) .0185(6) .0005(5) .0063(5) .0032(4)
C3 .0318(7) .0264(6) .0274(7) .0045(5) .0095(5) .0026(5)
C4 .0482(8) .0238(6) .0302(7) .0042(6) .0151(6) -.0034(5)
C5 .0439(8) .0290(6) .0250(7) -.0071(6) .0078(6) -.0064(5)
C6 .0304(7) .0298(6) .0215(6) -.0050(5) .0063(5) -.0009(5)
C13 .0288(7) .0236(6) .0338(7) -.0036(5) .0061(6) -.0004(5)
C14 .0253(7) .0369(8) .0329(8) .0009(6) .0011(6) .0046(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
C12 C7 C8 118.43(10)
C12 C7 C1 119.12(10)
C8 C7 C1 122.45(10)
C9 C8 C7 120.04(11)
C9 C8 C15 118.83(10)
C7 C8 C15 121.09(10)
C10 C9 C8 120.49(11)
C9 C10 C11 119.85(11)
C12 C11 C10 120.16(12)
C11 C12 C7 121.03(11)
O1 C15 C8 124.40(11)
C2 N1 C14 116.05(10)
C2 N1 C13 115.28(10)
C14 N1 C13 110.49(10)
C6 C1 C2 119.03(10)
C6 C1 C7 118.32(10)
C2 C1 C7 122.64(10)
C3 C2 C1 118.53(11)
C3 C2 N1 122.05(11)
C1 C2 N1 119.34(10)
C4 C3 C2 121.27(12)
C5 C4 C3 120.32(12)
C4 C5 C6 119.28(12)
C5 C6 C1 121.51(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C15 . 1.2077(15) ?
C7 C12 . 1.3959(17) ?
C7 C8 . 1.4058(16) ?
C7 C1 . 1.4939(16) ?
C8 C9 . 1.3992(17) ?
C8 C15 . 1.4773(17) ?
C9 C10 . 1.3802(18) ?
C10 C11 . 1.3870(19) ?
C11 C12 . 1.3869(18) ?
N1 C2 . 1.4220(15) ?
N1 C14 . 1.4566(16) ?
N1 C13 . 1.4632(16) ?
C1 C6 . 1.3975(16) ?
C1 C2 . 1.4124(17) ?
C2 C3 . 1.3970(17) ?
C3 C4 . 1.3858(19) ?
C4 C5 . 1.381(2) ?
C5 C6 . 1.3853(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21135209
2 PubChem 91154386