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#$Date: 2022-03-25 12:23:26 +0200 (Fri, 25 Mar 2022) $
#$Revision: 273997 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/48/8104882.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_8104882
loop_
_publ_author_name
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 Crystal structure of N,N-diphenylformamide, C13H11NO
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              57
_journal_page_last               59
_journal_paper_doi               10.1515/ncrs-2020-0430
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C13 H11 N O'
_chemical_formula_sum            'C13 H11 N O'
_chemical_formula_weight         197.23
_chemical_name_common            N,N-Diphenylformamide
_chemical_name_systematic        N,N-Diphenylformamide
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      29
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.801(4)
_cell_length_b                   6.0510(13)
_cell_length_c                   7.2677(14)
_cell_measurement_reflns_used    5663
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.10
_cell_measurement_theta_min      2.57
_cell_volume                     1046.7(3)
_computing_cell_refinement       'SAINT [1]'
_computing_data_collection       'APEX2 [1]'
_computing_data_reduction        'SAINT [1]'
_computing_molecular_graphics    'ORTEP3 [3], Mercury [4]'
_computing_publication_material  'SHELXL-97 [2], PLATON [5]'
_computing_structure_refinement  'SHELXL-97 [2]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8805
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.980
_diffrn_reflns_theta_min         1.711
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9392
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS [6]                                         
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       platelet
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.533
_exptl_crystal_size_mid          0.414
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.109
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 894 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2435
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0383P)²+0.1750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0896
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                2215
_reflns_number_total             2435
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0430_suppl.cif
_cod_data_source_block           g
_cod_database_code               8104882
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.20491(8) 0.1138(3) 1.1184(2) 0.0623(5) Uani 1 1 d . . . . .
N1 N 0.15502(7) 0.2760(3) 0.8851(2) 0.0357(4) Uani 1 1 d . . . . .
C1 C 0.20289(9) 0.2146(4) 0.9744(3) 0.0476(5) Uani 1 1 d . . . . .
H1 H 0.237636 0.254101 0.919125 0.057 Uiso 1 1 calc R U . . .
C11 C 0.10008(8) 0.2313(3) 0.9566(3) 0.0338(4) Uani 1 1 d . . . . .
C12 C 0.05935(8) 0.3943(3) 0.9475(3) 0.0384(4) Uani 1 1 d . . . . .
H12 H 0.067806 0.532495 0.891941 0.046 Uiso 1 1 calc R U . . .
C13 C 0.00625(9) 0.3563(4) 1.0193(3) 0.0518(6) Uani 1 1 d . . . . .
H13 H -0.021596 0.468461 1.012349 0.062 Uiso 1 1 calc R U . . .
C14 C -0.00630(12) 0.1572(5) 1.1003(4) 0.0623(7) Uani 1 1 d . . . . .
H14 H -0.042573 0.132103 1.150692 0.075 Uiso 1 1 calc R U . . .
C15 C 0.03386(13) -0.0052(5) 1.1080(3) 0.0614(7) Uani 1 1 d . . . . .
H15 H 0.024988 -0.143169 1.163281 0.074 Uiso 1 1 calc R U . . .
C16 C 0.08721(10) 0.0287(4) 1.0365(3) 0.0478(5) Uani 1 1 d . . . . .
H16 H 0.114631 -0.085169 1.042042 0.057 Uiso 1 1 calc R U . . .
C21 C 0.15990(7) 0.4173(3) 0.7270(3) 0.0323(4) Uani 1 1 d . . . . .
C22 C 0.18657(8) 0.6188(4) 0.7428(3) 0.0436(5) Uani 1 1 d . . . . .
H22 H 0.201837 0.663403 0.857690 0.052 Uiso 1 1 calc R U . . .
C23 C 0.19106(10) 0.7557(4) 0.5914(4) 0.0579(7) Uani 1 1 d . . . . .
H23 H 0.210066 0.893198 0.601713 0.069 Uiso 1 1 calc R U . . .
C24 C 0.16818(11) 0.6936(4) 0.4267(4) 0.0608(7) Uani 1 1 d . . . . .
H24 H 0.170760 0.789279 0.323431 0.073 Uiso 1 1 calc R U . . .
C25 C 0.14137(10) 0.4925(5) 0.4101(3) 0.0559(6) Uani 1 1 d . . . . .
H25 H 0.125755 0.449763 0.295176 0.067 Uiso 1 1 calc R U . . .
C26 C 0.13713(9) 0.3522(4) 0.5609(3) 0.0413(5) Uani 1 1 d . . . . .
H26 H 0.118809 0.213298 0.549843 0.050 Uiso 1 1 calc R U . . .
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
C1 N1 C11 122.57(16) . .
C1 N1 C21 118.40(17) . .
C11 N1 C21 118.44(14) . .
O1 C1 N1 125.6(2) . .
O1 C1 H1 117.2 . .
N1 C1 H1 117.2 . .
C12 C11 C16 119.59(19) . .
C12 C11 N1 119.15(16) . .
C16 C11 N1 121.26(18) . .
C11 C12 C13 120.1(2) . .
C11 C12 H12 119.9 . .
C13 C12 H12 119.9 . .
C14 C13 C12 120.3(2) . .
C14 C13 H13 119.8 . .
C12 C13 H13 119.8 . .
C15 C14 C13 119.6(2) . .
C15 C14 H14 120.2 . .
C13 C14 H14 120.2 . .
C14 C15 C16 121.1(2) . .
C14 C15 H15 119.5 . .
C16 C15 H15 119.5 . .
C15 C16 C11 119.2(2) . .
C15 C16 H16 120.4 . .
C11 C16 H16 120.4 . .
C22 C21 C26 120.40(19) . .
C22 C21 N1 119.78(18) . .
C26 C21 N1 119.82(17) . .
C21 C22 C23 120.0(2) . .
C21 C22 H22 120.0 . .
C23 C22 H22 120.0 . .
C24 C23 C22 120.1(2) . .
C24 C23 H23 120.0 . .
C22 C23 H23 120.0 . .
C23 C24 C25 120.2(2) . .
C23 C24 H24 119.9 . .
C25 C24 H24 119.9 . .
C24 C25 C26 120.2(2) . .
C24 C25 H25 119.9 . .
C26 C25 H25 119.9 . .
C21 C26 C25 119.1(2) . .
C21 C26 H26 120.5 . .
C25 C26 H26 120.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.212(3) .
N1 C1 1.363(3) .
N1 C11 1.433(2) .
N1 C21 1.437(2) .
C1 H1 0.9500 .
C11 C12 1.384(3) .
C11 C16 1.391(3) .
C12 C13 1.386(3) .
C12 H12 0.9500 .
C13 C14 1.374(4) .
C13 H13 0.9500 .
C14 C15 1.372(4) .
C14 H14 0.9500 .
C15 C16 1.387(4) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C21 C22 1.379(3) .
C21 C26 1.381(3) .
C22 C23 1.381(3) .
C22 H22 0.9500 .
C23 C24 1.368(4) .
C23 H23 0.9500 .
C24 C25 1.379(4) .
C24 H24 0.9500 .
C25 C26 1.390(3) .
C25 H25 0.9500 .
C26 H26 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
C23 H23 O1 0.95 2.43 3.296(3) 152.0 3_564
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C11 N1 C1 O1 1.7(3) . . . .
C21 N1 C1 O1 172.8(2) . . . .
C1 N1 C11 C12 137.2(2) . . . .
C21 N1 C11 C12 -33.9(3) . . . .
C1 N1 C11 C16 -42.1(3) . . . .
C21 N1 C11 C16 146.81(19) . . . .
C16 C11 C12 C13 0.6(3) . . . .
N1 C11 C12 C13 -178.7(2) . . . .
C11 C12 C13 C14 0.2(3) . . . .
C12 C13 C14 C15 -0.8(4) . . . .
C13 C14 C15 C16 0.5(4) . . . .
C14 C15 C16 C11 0.3(4) . . . .
C12 C11 C16 C15 -0.9(3) . . . .
N1 C11 C16 C15 178.4(2) . . . .
C1 N1 C21 C22 -56.7(2) . . . .
C11 N1 C21 C22 114.8(2) . . . .
C1 N1 C21 C26 124.3(2) . . . .
C11 N1 C21 C26 -64.2(2) . . . .
C26 C21 C22 C23 -0.6(3) . . . .
N1 C21 C22 C23 -179.62(19) . . . .
C21 C22 C23 C24 1.2(3) . . . .
C22 C23 C24 C25 -1.1(4) . . . .
C23 C24 C25 C26 0.4(4) . . . .
C22 C21 C26 C25 -0.1(3) . . . .
N1 C21 C26 C25 178.90(18) . . . .
C24 C25 C26 C21 0.2(3) . . . .
