#------------------------------------------------------------------------------
#$Date: 2021-05-29 08:15:26 +0300 (Sat, 29 May 2021) $
#$Revision: 265611 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243842.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_2243842
loop_
_publ_author_name
'Miyamoto, Hisakazu'
'Takahashi, Hiroki'
_publ_section_title
;
 Crystal structure and photoreactive behaviour of
 N,N-diisopropyl(p-phenylphenyl)glyoxylamide
;
_journal_coeditor_code           DJ2024
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              653
_journal_page_last               657
_journal_paper_doi               10.1107/S2056989021005387
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C20 H23 N O2'
_chemical_formula_moiety         'C20 H23 N O2'
_chemical_formula_sum            'C20 H23 N O2'
_chemical_formula_weight         309.39
_chemical_name_common
;
N,N-Diisopropyl(p-phenylphenyl)glyoxylamide
;
_chemical_name_systematic
;
2-([1,1'-Biphenyl]-4-yl)-2-oxo-N,N-bis(propan-2-yl)acetamide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1313(2)
_cell_length_b                   7.3710(2)
_cell_length_c                   38.1143(11)
_cell_measurement_reflns_used    2939
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.4
_cell_volume                     1722.53(9)
_computing_cell_refinement
;
CrystalClear-SM Expert (Rigaku, 2009)
;
_computing_data_collection
;
CrystalClear-SM Expert (Rigaku, 2009)
;
_computing_data_reduction
;
CrystalClear-SM Expert (Rigaku, 2009)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Rigaku Saturn 724+ CCD'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            16094
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.965
_diffrn_reflns_theta_min         3.365
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(CrystalClear-SM Expert; Rigaku, 2009)
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       Prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.290
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.146
_refine_ls_abs_structure_details
;
Flack x determined using 1346 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0314P)²+0.3778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0803
_reflns_number_gt                3614
_reflns_number_total             3877
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dj2024sup1.cif
_cod_data_source_block           I
_cod_database_code               2243842
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5093(3) 0.5728(2) 0.66469(4) 0.0240(3) Uani d 1 . .
C C2 0.6161(3) 0.6491(2) 0.69356(4) 0.0264(4) Uani d 1 . .
H H1 0.757076 0.700514 0.690769 0.032 Uiso calc 1 . .
C C3 0.5171(3) 0.6499(2) 0.72609(4) 0.0256(3) Uani d 1 . .
H H2 0.591743 0.702783 0.745390 0.031 Uiso calc 1 . .
C C4 0.3097(3) 0.5750(2) 0.73146(4) 0.0231(3) Uani d 1 . .
O O1 0.8128(2) 0.6133(2) 0.62656(3) 0.0413(3) Uani d 1 . .
O O2 0.4869(2) 0.32629(16) 0.59665(3) 0.0381(3) Uani d 1 . .
N N1 0.4188(2) 0.61084(19) 0.57509(4) 0.0276(3) Uani d 1 . .
C C5 0.2040(3) 0.5007(2) 0.70210(5) 0.0282(4) Uani d 1 . .
H H3 0.062937 0.449217 0.704797 0.034 Uiso calc 1 . .
C C6 0.3012(3) 0.5011(2) 0.66922(4) 0.0287(4) Uani d 1 . .
H H4 0.225190 0.452194 0.649669 0.034 Uiso calc 1 . .
C C7 0.6227(3) 0.5697(2) 0.63028(4) 0.0284(4) Uani d 1 . .
C C8 0.4985(3) 0.4927(2) 0.59863(4) 0.0281(4) Uani d 1 . .
C C9 0.4364(3) 0.8099(2) 0.58034(5) 0.0318(4) Uani d 1 . .
H H5 0.497384 0.829750 0.604367 0.038 Uiso calc 1 . .
C C10 0.5949(4) 0.8947(3) 0.55449(6) 0.0470(5) Uani d 1 . .
H H6 0.736401 0.833410 0.556225 0.070 Uiso calc 1 . .
H H7 0.612914 1.023717 0.559944 0.070 Uiso calc 1 . .
H H8 0.537864 0.881506 0.530604 0.070 Uiso calc 1 . .
C C11 0.2145(4) 0.9013(3) 0.57929(6) 0.0424(5) Uani d 1 . .
H H9 0.156583 0.896594 0.555338 0.064 Uiso calc 1 . .
H H10 0.229103 1.028114 0.586642 0.064 Uiso calc 1 . .
H H11 0.114502 0.838140 0.595205 0.064 Uiso calc 1 . .
C C12 0.3111(3) 0.5445(2) 0.54250(4) 0.0309(4) Uani d 1 . .
H H12 0.270143 0.654227 0.528562 0.037 Uiso calc 1 . .
C C13 0.4680(4) 0.4345(3) 0.51993(5) 0.0466(5) Uani d 1 . .
H H13 0.601203 0.504937 0.515886 0.070 Uiso calc 1 . .
H H14 0.398812 0.406781 0.497376 0.070 Uiso calc 1 . .
H H15 0.504725 0.321214 0.532000 0.070 Uiso calc 1 . .
C C14 0.1007(4) 0.4442(3) 0.55063(6) 0.0434(5) Uani d 1 . .
H H16 0.134408 0.331101 0.563027 0.065 Uiso calc 1 . .
H H17 0.024513 0.416204 0.528682 0.065 Uiso calc 1 . .
H H18 0.007510 0.520425 0.565414 0.065 Uiso calc 1 . .
C C15 0.2068(3) 0.5729(2) 0.76699(4) 0.0242(3) Uani d 1 . .
C C16 0.3150(3) 0.6450(2) 0.79631(5) 0.0327(4) Uani d 1 . .
H H19 0.454724 0.698538 0.793378 0.039 Uiso calc 1 . .
C C17 0.2219(4) 0.6397(3) 0.82944(5) 0.0385(5) Uani d 1 . .
H H20 0.299212 0.687471 0.848972 0.046 Uiso calc 1 . .
C C18 0.0172(4) 0.5653(3) 0.83418(5) 0.0387(5) Uani d 1 . .
H H21 -0.047408 0.563386 0.856828 0.046 Uiso calc 1 . .
C C19 -0.0930(3) 0.4937(3) 0.80572(5) 0.0360(4) Uani d 1 . .
H H22 -0.233437 0.441822 0.808872 0.043 Uiso calc 1 . .
C C20 0.0005(3) 0.4972(2) 0.77263(5) 0.0295(4) Uani d 1 . .
H H23 -0.077146 0.447082 0.753360 0.035 Uiso calc 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 118.98(15) ?
C6 C1 C7 . . 122.22(15) ?
C2 C1 C7 . . 118.80(15) ?
C3 C2 C1 . . 120.18(15) ?
C3 C2 H1 . . 119.9 ?
C1 C2 H1 . . 119.9 ?
C2 C3 C4 . . 121.88(15) ?
C2 C3 H2 . . 119.1 ?
C4 C3 H2 . . 119.1 ?
C3 C4 C5 . . 117.15(15) ?
C3 C4 C15 . . 121.29(14) ?
C5 C4 C15 . . 121.56(15) ?
C8 N1 C9 . . 121.65(14) ?
C8 N1 C12 . . 120.38(14) ?
C9 N1 C12 . . 117.97(14) ?
C6 C5 C4 . . 121.36(16) ?
C6 C5 H3 . . 119.3 ?
C4 C5 H3 . . 119.3 ?
C5 C6 C1 . . 120.44(15) ?
C5 C6 H4 . . 119.8 ?
C1 C6 H4 . . 119.8 ?
O1 C7 C1 . . 123.19(16) ?
O1 C7 C8 . . 118.74(16) ?
C1 C7 C8 . . 117.87(15) ?
O2 C8 N1 . . 125.77(17) ?
O2 C8 C7 . . 116.41(16) ?
N1 C8 C7 . . 117.78(15) ?
N1 C9 C10 . . 111.42(16) ?
N1 C9 C11 . . 111.71(16) ?
C10 C9 C11 . . 111.97(16) ?
N1 C9 H5 . . 107.1 ?
C10 C9 H5 . . 107.1 ?
C11 C9 H5 . . 107.1 ?
C9 C10 H6 . . 109.5 ?
C9 C10 H7 . . 109.5 ?
H6 C10 H7 . . 109.5 ?
C9 C10 H8 . . 109.5 ?
H6 C10 H8 . . 109.5 ?
H7 C10 H8 . . 109.5 ?
C9 C11 H9 . . 109.5 ?
C9 C11 H10 . . 109.5 ?
H9 C11 H10 . . 109.5 ?
C9 C11 H11 . . 109.5 ?
H9 C11 H11 . . 109.5 ?
H10 C11 H11 . . 109.5 ?
N1 C12 C14 . . 111.50(15) ?
N1 C12 C13 . . 111.46(16) ?
C14 C12 C13 . . 113.10(17) ?
N1 C12 H12 . . 106.8 ?
C14 C12 H12 . . 106.8 ?
C13 C12 H12 . . 106.8 ?
C12 C13 H13 . . 109.5 ?
C12 C13 H14 . . 109.5 ?
H13 C13 H14 . . 109.5 ?
C12 C13 H15 . . 109.5 ?
H13 C13 H15 . . 109.5 ?
H14 C13 H15 . . 109.5 ?
C12 C14 H16 . . 109.5 ?
C12 C14 H17 . . 109.5 ?
H16 C14 H17 . . 109.5 ?
C12 C14 H18 . . 109.5 ?
H16 C14 H18 . . 109.5 ?
H17 C14 H18 . . 109.5 ?
C20 C15 C16 . . 117.12(16) ?
C20 C15 C4 . . 121.66(15) ?
C16 C15 C4 . . 121.21(16) ?
C17 C16 C15 . . 121.34(18) ?
C17 C16 H19 . . 119.3 ?
C15 C16 H19 . . 119.3 ?
C18 C17 C16 . . 120.26(18) ?
C18 C17 H20 . . 119.9 ?
C16 C17 H20 . . 119.9 ?
C17 C18 C19 . . 119.54(17) ?
C17 C18 H21 . . 120.2 ?
C19 C18 H21 . . 120.2 ?
C18 C19 C20 . . 120.33(19) ?
C18 C19 H22 . . 119.8 ?
C20 C19 H22 . . 119.8 ?
C19 C20 C15 . . 121.40(17) ?
C19 C20 H23 . . 119.3 ?
C15 C20 H23 . . 119.3 ?
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
C1 C6 . 1.392(3) ?
C1 C2 . 1.398(2) ?
C1 C7 . 1.485(2) ?
C2 C3 . 1.380(2) ?
C2 H1 . 0.9500 ?
C3 C4 . 1.401(2) ?
C3 H2 . 0.9500 ?
C4 C5 . 1.404(2) ?
C4 C15 . 1.494(2) ?
O1 C7 . 1.217(2) ?
O2 C8 . 1.231(2) ?
N1 C8 . 1.342(2) ?
N1 C9 . 1.485(2) ?
N1 C12 . 1.489(2) ?
C5 C6 . 1.388(2) ?
C5 H3 . 0.9500 ?
C6 H4 . 0.9500 ?
C7 C8 . 1.535(2) ?
C9 C10 . 1.519(3) ?
C9 C11 . 1.519(3) ?
C9 H5 . 1.0000 ?
C10 H6 . 0.9800 ?
C10 H7 . 0.9800 ?
C10 H8 . 0.9800 ?
C11 H9 . 0.9800 ?
C11 H10 . 0.9800 ?
C11 H11 . 0.9800 ?
C12 C14 . 1.519(3) ?
C12 C13 . 1.524(3) ?
C12 H12 . 1.0000 ?
C13 H13 . 0.9800 ?
C13 H14 . 0.9800 ?
C13 H15 . 0.9800 ?
C14 H16 . 0.9800 ?
C14 H17 . 0.9800 ?
C14 H18 . 0.9800 ?
C15 C20 . 1.399(3) ?
C15 C16 . 1.404(2) ?
C16 C17 . 1.386(3) ?
C16 H19 . 0.9500 ?
C17 C18 . 1.382(3) ?
C17 H20 . 0.9500 ?
C18 C19 . 1.382(3) ?
C18 H21 . 0.9500 ?
C19 C20 . 1.385(3) ?
C19 H22 . 0.9500 ?
C20 H23 . 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
_geom_hbond_publ_flag
C9 H5 O1 . 1.00 2.65 3.245(2) 119 yes
C13 H15 O2 . 0.98 2.47 3.033(3) 117 yes
C14 H16 O2 . 0.98 2.51 3.072(3) 116 yes
C14 H18 O1 1_455 0.98 2.71 3.612(3) 154 yes
C17 H20 O2 4_656 0.95 2.66 3.608(2) 179 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 1.2(2) ?
C7 C1 C2 C3 . . . . -178.37(15) ?
C1 C2 C3 C4 . . . . 0.3(2) ?
C2 C3 C4 C5 . . . . -1.0(2) ?
C2 C3 C4 C15 . . . . 178.55(15) ?
C3 C4 C5 C6 . . . . 0.2(3) ?
C15 C4 C5 C6 . . . . -179.27(16) ?
C4 C5 C6 C1 . . . . 1.2(3) ?
C2 C1 C6 C5 . . . . -1.9(2) ?
C7 C1 C6 C5 . . . . 177.64(16) ?
C6 C1 C7 O1 . . . . -171.73(18) ?
C2 C1 C7 O1 . . . . 7.8(3) ?
C6 C1 C7 C8 . . . . 3.1(2) ?
C2 C1 C7 C8 . . . . -177.40(15) ?
C9 N1 C8 O2 . . . . 178.42(19) ?
C12 N1 C8 O2 . . . . -2.2(3) ?
C9 N1 C8 C7 . . . . -3.9(2) ?
C12 N1 C8 C7 . . . . 175.50(16) ?
O1 C7 C8 O2 . . . . 97.1(2) ?
C1 C7 C8 O2 . . . . -77.9(2) ?
O1 C7 C8 N1 . . . . -80.7(2) ?
C1 C7 C8 N1 . . . . 104.20(19) ?
C8 N1 C9 C10 . . . . 110.4(2) ?
C12 N1 C9 C10 . . . . -69.1(2) ?
C8 N1 C9 C11 . . . . -123.57(18) ?
C12 N1 C9 C11 . . . . 57.0(2) ?
C8 N1 C12 C14 . . . . 65.9(2) ?
C9 N1 C12 C14 . . . . -114.69(18) ?
C8 N1 C12 C13 . . . . -61.6(2) ?
C9 N1 C12 C13 . . . . 117.88(18) ?
C3 C4 C15 C20 . . . . -179.53(16) ?
C5 C4 C15 C20 . . . . -0.1(2) ?
C3 C4 C15 C16 . . . . -0.4(2) ?
C5 C4 C15 C16 . . . . 179.07(17) ?
C20 C15 C16 C17 . . . . 0.6(3) ?
C4 C15 C16 C17 . . . . -178.57(17) ?
C15 C16 C17 C18 . . . . -1.1(3) ?
C16 C17 C18 C19 . . . . 1.0(3) ?
C17 C18 C19 C20 . . . . -0.3(3) ?
C18 C19 C20 C15 . . . . -0.2(3) ?
C16 C15 C20 C19 . . . . 0.0(2) ?
C4 C15 C20 C19 . . . . 179.20(16) ?

_cod_database_fobs_code 2243842
