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#$Date: 2023-03-02 12:36:04 +0200 (Thu, 02 Mar 2023) $
#$Revision: 281258 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106825.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_8106825
loop_
_publ_author_name
'Mabkhot, Yahia Nasser'
'Barakat, Assem'
'Ghabbour, Hazem A.'
'Fun, Hoong-Kun'
_publ_section_title
;
 Crystal structure of 2-amino-N-(4-methoxyphenyl)benzamide, C14H14N2O2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              203
_journal_page_last               204
_journal_paper_doi               10.1515/ncrs-2015-0089
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 100.448(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5536(9)
_cell_length_b                   5.0730(3)
_cell_length_c                   17.6641(12)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.99
_cell_measurement_theta_min      2.34
_cell_volume                     1194.40(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 Venture area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_source         'fine-focus micro-tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            27499
_diffrn_reflns_theta_full        33.15
_diffrn_reflns_theta_max         33.15
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_correction_T_min  0.9592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.458
_exptl_crystal_size_mid          0.365
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         4542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0461
_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)+(0.0637P)²+0.4126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1250
_reflns_number_gt                3515
_reflns_number_total             4542
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0089_suppl.cif
_cod_data_source_block           ie
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               8106825
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_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
O1 O 0.54796(5) 0.61486(14) 0.37478(4) 0.01443(15) Uani 1 1 d . . .
O2 O 0.10136(5) 0.19638(15) 0.34968(4) 0.01463(15) Uani 1 1 d . . .
N1 N 0.71804(7) 0.66015(19) 0.30501(5) 0.01728(18) Uani 1 1 d . . .
N2 N 0.52000(6) 0.17839(16) 0.38958(5) 0.01180(16) Uani 1 1 d . . .
C1 C 0.75525(7) 0.48494(19) 0.36367(5) 0.01255(18) Uani 1 1 d . . .
C2 C 0.85896(8) 0.4407(2) 0.38313(6) 0.0169(2) Uani 1 1 d . . .
H2A H 0.9033 0.5429 0.3591 0.020 Uiso 1 1 calc R . .
C3 C 0.89783(8) 0.2509(2) 0.43662(6) 0.0178(2) Uani 1 1 d . . .
H3A H 0.9684 0.2269 0.4496 0.021 Uiso 1 1 calc R . .
C4 C 0.83432(7) 0.0945(2) 0.47166(6) 0.01541(19) Uani 1 1 d . . .
H4A H 0.8610 -0.0388 0.5073 0.018 Uiso 1 1 calc R . .
C5 C 0.73160(7) 0.13682(19) 0.45353(5) 0.01249(18) Uani 1 1 d . . .
H5A H 0.6880 0.0313 0.4773 0.015 Uiso 1 1 calc R . .
C6 C 0.69097(7) 0.33200(18) 0.40089(5) 0.01022(17) Uani 1 1 d . . .
C7 C 0.58114(7) 0.38808(18) 0.38729(5) 0.01021(17) Uani 1 1 d . . .
C8 C 0.41307(7) 0.18989(18) 0.37815(5) 0.01051(17) Uani 1 1 d . . .
C9 C 0.35854(7) -0.00301(19) 0.33277(6) 0.01241(18) Uani 1 1 d . . .
H9A H 0.3929 -0.1331 0.3088 0.015 Uiso 1 1 calc R . .
C10 C 0.25386(7) -0.00822(19) 0.32189(6) 0.01253(18) Uani 1 1 d . . .
H10A H 0.2171 -0.1415 0.2911 0.015 Uiso 1 1 calc R . .
C11 C 0.20407(7) 0.18385(19) 0.35659(5) 0.01092(17) Uani 1 1 d . . .
C12 C 0.25832(7) 0.37806(19) 0.40201(6) 0.01272(18) Uani 1 1 d . . .
H12A H 0.2239 0.5089 0.4256 0.015 Uiso 1 1 calc R . .
C13 C 0.36239(7) 0.38164(19) 0.41301(5) 0.01232(18) Uani 1 1 d . . .
H13A H 0.3990 0.5142 0.4442 0.015 Uiso 1 1 calc R . .
C14 C 0.04602(8) -0.0231(2) 0.31302(6) 0.0175(2) Uani 1 1 d . . .
H14A H -0.0256 0.0021 0.3135 0.026 Uiso 1 1 calc R . .
H14B H 0.0692 -0.1854 0.3408 0.026 Uiso 1 1 calc R . .
H14C H 0.0565 -0.0365 0.2597 0.026 Uiso 1 1 calc R . .
H1N2 H 0.5447(11) 0.018(3) 0.3888(8) 0.023(4) Uiso 1 1 d . . .
H2N1 H 0.7624(12) 0.781(3) 0.2941(9) 0.029(4) Uiso 1 1 d . . .
H1N1 H 0.6560(12) 0.726(3) 0.3073(9) 0.027(4) Uiso 1 1 d . . .
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
C11 O2 C14 116.30(8) . .
C1 N1 H2N1 115.3(10) . .
C1 N1 H1N1 114.5(10) . .
H2N1 N1 H1N1 114.5(15) . .
C7 N2 C8 125.09(8) . .
C7 N2 H1N2 119.2(10) . .
C8 N2 H1N2 114.5(10) . .
N1 C1 C2 119.82(9) . .
N1 C1 C6 121.80(9) . .
C2 C1 C6 118.20(9) . .
C3 C2 C1 121.24(10) . .
C3 C2 H2A 119.4 . .
C1 C2 H2A 119.4 . .
C2 C3 C4 120.61(9) . .
C2 C3 H3A 119.7 . .
C4 C3 H3A 119.7 . .
C5 C4 C3 118.91(9) . .
C5 C4 H4A 120.5 . .
C3 C4 H4A 120.5 . .
C4 C5 C6 121.32(9) . .
C4 C5 H5A 119.3 . .
C6 C5 H5A 119.3 . .
C5 C6 C1 119.67(9) . .
C5 C6 C7 120.16(8) . .
C1 C6 C7 120.09(8) . .
O1 C7 N2 122.01(9) . .
O1 C7 C6 121.64(8) . .
N2 C7 C6 116.35(8) . .
C9 C8 C13 119.48(9) . .
C9 C8 N2 118.22(8) . .
C13 C8 N2 122.26(8) . .
C8 C9 C10 120.88(9) . .
C8 C9 H9A 119.6 . .
C10 C9 H9A 119.6 . .
C11 C10 C9 119.23(9) . .
C11 C10 H10A 120.4 . .
C9 C10 H10A 120.4 . .
O2 C11 C10 123.88(9) . .
O2 C11 C12 115.98(8) . .
C10 C11 C12 120.14(9) . .
C13 C12 C11 120.43(9) . .
C13 C12 H12A 119.8 . .
C11 C12 H12A 119.8 . .
C12 C13 C8 119.84(9) . .
C12 C13 H13A 120.1 . .
C8 C13 H13A 120.1 . .
O2 C14 H14A 109.5 . .
O2 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
O2 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.2404(11) .
O2 C11 1.3767(11) .
O2 C14 1.4303(13) .
N1 C1 1.3888(13) .
N1 H2N1 0.902(17) .
N1 H1N1 0.913(16) .
N2 C7 1.3535(12) .
N2 C8 1.4277(12) .
N2 H1N2 0.880(16) .
C1 C2 1.4032(14) .
C1 C6 1.4146(13) .
C2 C3 1.3845(15) .
C2 H2A 0.9500 .
C3 C4 1.3954(15) .
C3 H3A 0.9500 .
C4 C5 1.3875(13) .
C4 H4A 0.9500 .
C5 C6 1.4009(13) .
C5 H5A 0.9500 .
C6 C7 1.4916(13) .
C8 C9 1.3897(13) .
C8 C13 1.3967(13) .
C9 C10 1.3971(13) .
C9 H9A 0.9500 .
C10 C11 1.3894(13) .
C10 H10A 0.9500 .
C11 C12 1.3932(13) .
C12 C13 1.3886(13) .
C12 H12A 0.9500 .
C13 H13A 0.9500 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
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
N1 C1 C2 C3 -174.35(10) . . . .
C6 C1 C2 C3 0.70(15) . . . .
C1 C2 C3 C4 1.23(16) . . . .
C2 C3 C4 C5 -1.67(16) . . . .
C3 C4 C5 C6 0.18(15) . . . .
C4 C5 C6 C1 1.75(14) . . . .
C4 C5 C6 C7 -175.00(9) . . . .
N1 C1 C6 C5 172.79(9) . . . .
C2 C1 C6 C5 -2.15(14) . . . .
N1 C1 C6 C7 -10.47(14) . . . .
C2 C1 C6 C7 174.59(9) . . . .
C8 N2 C7 O1 0.15(15) . . . .
C8 N2 C7 C6 179.96(8) . . . .
C5 C6 C7 O1 144.12(10) . . . .
C1 C6 C7 O1 -32.61(13) . . . .
C5 C6 C7 N2 -35.70(12) . . . .
C1 C6 C7 N2 147.57(9) . . . .
C7 N2 C8 C9 137.17(10) . . . .
C7 N2 C8 C13 -45.10(14) . . . .
C13 C8 C9 C10 -0.29(14) . . . .
N2 C8 C9 C10 177.51(9) . . . .
C8 C9 C10 C11 0.49(14) . . . .
C14 O2 C11 C10 8.62(13) . . . .
C14 O2 C11 C12 -170.95(9) . . . .
C9 C10 C11 O2 -179.90(9) . . . .
C9 C10 C11 C12 -0.35(14) . . . .
O2 C11 C12 C13 179.58(8) . . . .
C10 C11 C12 C13 0.00(14) . . . .
C11 C12 C13 C8 0.21(14) . . . .
C9 C8 C13 C12 -0.07(14) . . . .
N2 C8 C13 C12 -177.77(9) . . . .
