#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/35/2233599.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_2233599
loop_
_publ_author_name
'Rofouei, Mohammad Kazem'
'Attar Gharamaleki, Jafar'
'Younesian, Fereshteh'
'Bruno, Giuseppe'
'Rudbari, Hadi Amiri'
_publ_section_title
;
 N-(2-Ethoxyphenyl)formamide
;
_journal_coeditor_code           PV2505
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o505
_journal_paper_doi               10.1107/S160053681200205X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C9 H11 N O2'
_chemical_formula_moiety         'C9 H11 N O2'
_chemical_formula_sum            'C9 H11 N O2'
_chemical_formula_weight         165.19
_chemical_name_systematic
;
N-(2-Ethoxyphenyl)formamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.9079(4)
_cell_length_b                   14.1253(6)
_cell_length_c                   15.9555(7)
_cell_measurement_reflns_used    2150
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.11
_cell_measurement_theta_min      2.55
_cell_volume                     1782.25(14)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'XPW in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8725
_diffrn_reflns_theta_full        27.11
_diffrn_reflns_theta_max         27.11
_diffrn_reflns_theta_min         3.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Cubic
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0433
_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)+(0.0514P)²+0.2780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1203
_reflns_number_gt                1248
_reflns_number_total             1961
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2505.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               2233599
_cod_database_fobs_code          2233599
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.14029(12) 0.40133(8) 0.12756(7) 0.0571(3) Uani d . 1 1
N N1 -0.12270(15) 0.33831(10) 0.04588(8) 0.0525(4) Uani d . 1 1
H H1 -0.0300 0.3086 0.0561 0.063 Uiso calc R 1 1
O O2 -0.37570(15) 0.31796(10) -0.02102(9) 0.0808(4) Uani d . 1 1
C C1 0.3874(2) 0.33886(16) 0.18902(13) 0.0842(7) Uani d . 1 1
H H1A 0.3183 0.2875 0.2085 0.126 Uiso calc R 1 1
H H1B 0.4759 0.3507 0.2288 0.126 Uiso calc R 1 1
H H1C 0.4361 0.3226 0.1358 0.126 Uiso calc R 1 1
C C2 0.2815(2) 0.42535(14) 0.17963(11) 0.0653(5) Uani d . 1 1
H H2A 0.2425 0.4468 0.2340 0.078 Uiso calc R 1 1
H H2B 0.3469 0.4758 0.1540 0.078 Uiso calc R 1 1
C C3 0.00875(19) 0.46374(11) 0.12280(10) 0.0489(4) Uani d . 1 1
C C4 -0.13409(18) 0.43045(11) 0.07964(9) 0.0466(4) Uani d . 1 1
C C5 -0.23581(19) 0.29108(14) 0.00042(10) 0.0597(5) Uani d . 1 1
H H5 -0.2045 0.2307 -0.0170 0.072 Uiso calc R 1 1
C C6 -0.2759(2) 0.48701(12) 0.07355(11) 0.0585(5) Uani d . 1 1
H H6 -0.3704 0.4656 0.0446 0.070 Uiso calc R 1 1
C C7 -0.2773(2) 0.57530(14) 0.11042(14) 0.0732(6) Uani d . 1 1
H H7 -0.3740 0.6126 0.1075 0.088 Uiso calc R 1 1
C C8 -0.1370(3) 0.60824(13) 0.15134(14) 0.0784(6) Uani d . 1 1
H H8 -0.1384 0.6683 0.1751 0.094 Uiso calc R 1 1
C C9 0.0067(2) 0.55295(13) 0.15765(12) 0.0661(5) Uani d . 1 1
H H9 0.1017 0.5759 0.1853 0.079 Uiso calc R 1 1
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 0.0371(6) 0.0752(8) 0.0591(7) 0.0031(5) -0.0080(5) -0.0113(5)
N1 0.0351(6) 0.0705(9) 0.0520(8) 0.0038(6) -0.0041(6) -0.0075(7)
O2 0.0456(7) 0.0982(10) 0.0987(10) 0.0009(7) -0.0234(6) -0.0143(8)
C1 0.0558(11) 0.1186(17) 0.0781(13) 0.0172(11) -0.0227(10) -0.0244(12)
C2 0.0391(8) 0.0894(13) 0.0675(11) -0.0060(9) -0.0073(8) -0.0142(10)
C3 0.0410(8) 0.0582(9) 0.0476(9) -0.0031(7) 0.0054(7) 0.0057(7)
C4 0.0390(7) 0.0587(10) 0.0421(8) -0.0028(7) 0.0041(6) 0.0076(7)
C5 0.0450(9) 0.0784(12) 0.0556(10) -0.0038(9) -0.0016(8) -0.0094(8)
C6 0.0457(9) 0.0660(11) 0.0638(10) 0.0035(8) -0.0006(8) 0.0135(9)
C7 0.0614(12) 0.0597(11) 0.0984(15) 0.0127(10) 0.0058(11) 0.0182(10)
C8 0.0793(14) 0.0480(11) 0.1079(17) -0.0010(10) 0.0074(12) 0.0047(10)
C9 0.0584(11) 0.0632(11) 0.0768(13) -0.0131(9) 0.0000(9) 0.0013(9)
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
C3 O1 C2 118.24(12)
C5 N1 C4 128.85(14)
C5 N1 H1 115.6
C4 N1 H1 115.6
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O1 C2 C1 107.60(14)
O1 C2 H2A 110.2
C1 C2 H2A 110.2
O1 C2 H2B 110.2
C1 C2 H2B 110.2
H2A C2 H2B 108.5
O1 C3 C9 125.23(15)
O1 C3 C4 115.08(14)
C9 C3 C4 119.68(15)
C6 C4 C3 119.61(15)
C6 C4 N1 123.97(14)
C3 C4 N1 116.40(13)
O2 C5 N1 127.37(18)
O2 C5 H5 116.3
N1 C5 H5 116.3
C7 C6 C4 120.02(17)
C7 C6 H6 120.0
C4 C6 H6 120.0
C8 C7 C6 120.28(18)
C8 C7 H7 119.9
C6 C7 H7 119.9
C7 C8 C9 120.60(18)
C7 C8 H8 119.7
C9 C8 H8 119.7
C3 C9 C8 119.78(17)
C3 C9 H9 120.1
C8 C9 H9 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.3656(18)
O1 C2 1.4328(18)
N1 C5 1.331(2)
N1 C4 1.411(2)
N1 H1 0.8600
O2 C5 1.2185(19)
C1 C2 1.488(3)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 H2A 0.9700
C2 H2B 0.9700
C3 C9 1.377(2)
C3 C4 1.404(2)
C4 C6 1.380(2)
C5 H5 0.9300
C6 C7 1.379(3)
C6 H6 0.9300
C7 C8 1.369(3)
C7 H7 0.9300
C8 C9 1.383(3)
C8 H8 0.9300
C9 H9 0.9300
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 H1 O1 . 0.86 2.20 2.6108(16) 109.3
N1 H1 O2 2 0.86 2.24 2.9741(18) 143.9
C2 H2A Cg 8_656 0.97 2.78 3.5853(19) 141
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
C3 O1 C2 C1 167.77(15)
C2 O1 C3 C9 6.7(2)
C2 O1 C3 C4 -172.08(14)
O1 C3 C4 C6 178.00(13)
C9 C3 C4 C6 -0.8(2)
O1 C3 C4 N1 -0.97(19)
C9 C3 C4 N1 -179.82(14)
C5 N1 C4 C6 3.4(3)
C5 N1 C4 C3 -177.67(15)
C4 N1 C5 O2 -0.8(3)
C3 C4 C6 C7 -0.6(2)
N1 C4 C6 C7 178.25(15)
C4 C6 C7 C8 1.7(3)
C6 C7 C8 C9 -1.2(3)
O1 C3 C9 C8 -177.42(16)
C4 C3 C9 C8 1.3(3)
C7 C8 C9 C3 -0.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 498399
