#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2221722.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_2221722
loop_
_publ_author_name
'Yang, Zhao'
'Wang, Zhi-Xiang'
_publ_section_title
;
Phenyl N-(4-fluorophenyl)carbamate
;
_journal_coeditor_code HK2663
_journal_issue 5
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o1036
_journal_volume 65
_journal_year 2009
_chemical_formula_iupac 'C13 H10 F N O2'
_chemical_formula_moiety 'C13 H10 F N O2'
_chemical_formula_sum 'C13 H10 F N O2'
_chemical_formula_weight 231.22
_chemical_name_systematic
;
Phenyl N-(4-fluorophenyl)carbamate
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 96.62(3)
_cell_angle_beta 92.82(3)
_cell_angle_gamma 91.19(3)
_cell_formula_units_Z 4
_cell_length_a 5.8860(12)
_cell_length_b 7.8540(16)
_cell_length_c 24.761(5)
_cell_measurement_reflns_used 25
_cell_measurement_temperature 294(2)
_cell_measurement_theta_max 12
_cell_measurement_theta_min 8
_cell_volume 1135.3(4)
_computing_cell_refinement 'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection 'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics 'PLATON (Spek, 2009)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Enraf--Nonius CAD-4'
_diffrn_measurement_method \w/2\q
_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 0.0604
_diffrn_reflns_av_sigmaI/netI 0.0796
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min 0
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_l_max 29
_diffrn_reflns_limit_l_min -29
_diffrn_reflns_number 4548
_diffrn_reflns_theta_full 25.27
_diffrn_reflns_theta_max 25.27
_diffrn_reflns_theta_min 1.66
_diffrn_standards_decay_% 1
_diffrn_standards_interval_time 120
_diffrn_standards_number 3
_exptl_absorpt_coefficient_mu 0.103
_exptl_absorpt_correction_T_max 0.9918
_exptl_absorpt_correction_T_min 0.9898
_exptl_absorpt_correction_type psi-scan
_exptl_absorpt_process_details '(North et al., 1968)'
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.353
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 480
_exptl_crystal_size_max 0.10
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.08
_refine_diff_density_max 0.128
_refine_diff_density_min -0.129
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.000
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 307
_refine_ls_number_reflns 4110
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.000
_refine_ls_R_factor_all 0.1788
_refine_ls_R_factor_gt 0.0726
_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/[\s^2^(Fo^2^)+(0.052P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1214
_refine_ls_wR_factor_ref 0.1574
_reflns_number_gt 1662
_reflns_number_total 4110
_reflns_threshold_expression I>2\s(I)
_[local]_cod_data_source_file hk2663.cif
_[local]_cod_data_source_block I
_cod_database_code 2221722
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N N1 0.0390(6) -0.6473(4) 0.26993(14) 0.0831(11) Uani d . 1
H H1A -0.0691 -0.7213 0.2599 0.100 Uiso calc R 1
N N2 0.6939(5) -0.2644(4) 0.22504(13) 0.0755(11) Uani d . 1
H H2C 0.6083 -0.3507 0.2300 0.091 Uiso calc R 1
F F1 -0.0366(5) -0.3165(3) 0.47653(11) 0.1065(9) Uani d . 1
F F2 1.1428(5) -0.3284(4) 0.03482(12) 0.1253(11) Uani d . 1
O O1 0.1510(5) -0.7508(4) 0.19019(13) 0.1045(12) Uani d . 1
O O2 0.3575(5) -0.5355(4) 0.23766(11) 0.0916(10) Uani d . 1
O O3 0.5300(5) -0.1536(4) 0.29759(12) 0.0938(11) Uani d . 1
O O4 0.8164(4) -0.0021(3) 0.26628(10) 0.0724(8) Uani d . 1
C C1 0.3835(12) -0.7830(7) 0.0572(2) 0.1033(18) Uani d . 1
H H1B 0.3416 -0.7637 0.0218 0.124 Uiso calc R 1
C C2 0.2332(9) -0.7392(6) 0.0984(3) 0.0934(16) Uani d . 1
H H2A 0.0941 -0.6896 0.0917 0.112 Uiso calc R 1
C C3 0.3045(9) -0.7740(6) 0.1487(2) 0.0763(14) Uani d . 1
C C4 0.5077(11) -0.8420(6) 0.1599(2) 0.0894(16) Uani d . 1
H H4A 0.5516 -0.8605 0.1953 0.107 Uiso calc R 1
C C5 0.6465(9) -0.8828(6) 0.1186(3) 0.1024(18) Uani d . 1
H H5A 0.7849 -0.9327 0.1259 0.123 Uiso calc R 1
C C6 0.5889(11) -0.8528(7) 0.0673(3) 0.108(2) Uani d . 1
H H6A 0.6871 -0.8792 0.0394 0.130 Uiso calc R 1
C C7 0.1980(8) -0.6340(6) 0.23447(19) 0.0860(15) Uani d . 1
C C8 0.0241(7) -0.5556(5) 0.32213(17) 0.0698(12) Uani d . 1
C C9 -0.1636(7) -0.5849(5) 0.35086(18) 0.0740(12) Uani d . 1
H H9A -0.2782 -0.6603 0.3349 0.089 Uiso calc R 1
C C10 -0.1859(8) -0.5051(6) 0.4028(2) 0.0861(14) Uani d . 1
H H10A -0.3134 -0.5253 0.4221 0.103 Uiso calc R 1
C C11 -0.0157(8) -0.3963(5) 0.42483(19) 0.0776(13) Uani d . 1
C C12 0.1691(8) -0.3626(5) 0.39833(18) 0.0772(13) Uani d . 1
H H12A 0.2818 -0.2868 0.4150 0.093 Uiso calc R 1
C C13 0.1923(7) -0.4407(5) 0.34595(18) 0.0784(13) Uani d . 1
H H13A 0.3192 -0.4165 0.3269 0.094 Uiso calc R 1
C C14 0.4753(10) 0.1478(6) 0.4438(2) 0.0860(15) Uani d . 1
H H14A 0.4594 0.2114 0.4774 0.103 Uiso calc R 1
C C15 0.6668(9) 0.0580(6) 0.4346(2) 0.0882(15) Uani d . 1
H H15A 0.7815 0.0618 0.4620 0.106 Uiso calc R 1
C C16 0.6942(7) -0.0391(5) 0.3851(2) 0.0744(13) Uani d . 1
H H16A 0.8265 -0.0994 0.3790 0.089 Uiso calc R 1
C C17 0.5254(8) -0.0445(5) 0.34616(18) 0.0647(11) Uani d . 1
C C18 0.3329(8) 0.0490(6) 0.35436(18) 0.0775(13) Uani d . 1
H H18A 0.2203 0.0478 0.3266 0.093 Uiso calc R 1
C C19 0.3070(9) 0.1455(6) 0.4044(2) 0.0829(14) Uani d . 1
H H19A 0.1761 0.2075 0.4107 0.099 Uiso calc R 1
C C20 0.6969(7) -0.1294(6) 0.26345(17) 0.0763(13) Uani d . 1
C C21 0.8171(7) -0.2801(5) 0.17706(16) 0.0588(10) Uani d . 1
C C22 1.0269(7) -0.2011(5) 0.17460(18) 0.0738(12) Uani d . 1
H H22A 1.0954 -0.1378 0.2054 0.089 Uiso calc R 1
C C23 1.1343(7) -0.2167(5) 0.12616(19) 0.0798(13) Uani d . 1
H H23A 1.2738 -0.1612 0.1237 0.096 Uiso calc R 1
C C24 1.0365(9) -0.3124(6) 0.08250(19) 0.0840(14) Uani d . 1
C C25 0.8320(8) -0.3995(5) 0.08437(18) 0.0813(13) Uani d . 1
H H25A 0.7693 -0.4681 0.0540 0.098 Uiso calc R 1
C C26 0.7227(7) -0.3818(5) 0.13273(17) 0.0717(12) Uani d . 1
H H26A 0.5845 -0.4393 0.1352 0.086 Uiso calc R 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
N1 0.078(3) 0.080(3) 0.086(3) -0.031(2) 0.023(2) -0.013(2)
N2 0.082(3) 0.062(2) 0.080(3) -0.038(2) 0.023(2) -0.0024(19)
F1 0.120(2) 0.102(2) 0.094(2) -0.0065(17) 0.0279(17) -0.0139(16)
F2 0.140(3) 0.121(2) 0.112(2) -0.0283(19) 0.061(2) -0.0174(18)
O1 0.105(3) 0.109(3) 0.091(2) -0.056(2) 0.030(2) -0.027(2)
O2 0.094(2) 0.085(2) 0.091(2) -0.0490(18) 0.0269(18) -0.0119(17)
O3 0.099(2) 0.086(2) 0.089(2) -0.0449(18) 0.0397(19) -0.0265(18)
O4 0.0745(19) 0.0645(18) 0.0752(19) -0.0264(15) 0.0099(15) -0.0018(14)
C1 0.112(5) 0.125(5) 0.071(4) -0.036(4) -0.012(4) 0.014(3)
C2 0.081(4) 0.089(4) 0.112(5) -0.014(3) -0.010(4) 0.030(3)
C3 0.065(3) 0.070(3) 0.090(4) -0.027(3) 0.014(3) -0.005(3)
C4 0.099(4) 0.083(4) 0.083(4) -0.035(3) -0.008(3) 0.008(3)
C5 0.080(4) 0.063(3) 0.163(6) -0.007(3) -0.009(5) 0.013(4)
C6 0.081(4) 0.102(5) 0.134(6) -0.029(4) 0.032(4) -0.025(4)
C7 0.081(4) 0.093(4) 0.077(3) -0.033(3) 0.015(3) -0.015(3)
C8 0.069(3) 0.062(3) 0.079(3) -0.017(2) 0.015(2) 0.008(2)
C9 0.066(3) 0.067(3) 0.087(3) -0.016(2) 0.010(2) 0.002(2)
C10 0.083(3) 0.078(3) 0.097(4) -0.013(3) 0.025(3) 0.006(3)
C11 0.081(4) 0.061(3) 0.089(4) 0.005(3) 0.024(3) -0.007(3)
C12 0.081(3) 0.074(3) 0.076(3) -0.015(3) 0.000(3) 0.009(3)
C13 0.075(3) 0.077(3) 0.082(3) -0.030(2) 0.009(2) 0.006(3)
C14 0.093(4) 0.086(4) 0.078(4) -0.010(3) 0.020(3) 0.002(3)
C15 0.090(4) 0.098(4) 0.077(4) -0.012(3) 0.002(3) 0.018(3)
C16 0.055(3) 0.064(3) 0.108(4) -0.001(2) 0.015(3) 0.020(3)
C17 0.065(3) 0.057(3) 0.072(3) -0.014(2) 0.012(3) 0.005(2)
C18 0.077(4) 0.078(3) 0.079(3) -0.020(3) -0.004(3) 0.021(3)
C19 0.080(4) 0.069(3) 0.102(4) 0.013(3) 0.022(3) 0.008(3)
C20 0.081(3) 0.070(3) 0.076(3) -0.028(3) 0.017(3) -0.003(3)
C21 0.059(3) 0.048(2) 0.068(3) -0.007(2) 0.003(2) 0.002(2)
C22 0.054(3) 0.073(3) 0.090(3) -0.018(2) 0.002(2) -0.005(2)
C23 0.068(3) 0.070(3) 0.099(4) -0.010(2) 0.029(3) -0.007(3)
C24 0.099(4) 0.070(3) 0.082(4) -0.006(3) 0.032(3) -0.006(3)
C25 0.093(4) 0.073(3) 0.074(3) -0.006(3) 0.009(3) -0.008(2)
C26 0.072(3) 0.065(3) 0.074(3) -0.018(2) 0.007(2) -0.007(2)
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'
F F 0.0171 0.0103 '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
C7 N1 C8 128.3(4)
C7 N1 H1A 115.8
C8 N1 H1A 115.8
C20 N2 C21 126.8(3)
C20 N2 H2C 116.6
C21 N2 H2C 116.6
C7 O1 C3 120.4(3)
C20 O3 C17 118.5(3)
C6 C1 C2 122.3(5)
C6 C1 H1B 118.9
C2 C1 H1B 118.9
C3 C2 C1 115.4(5)
C3 C2 H2A 122.3
C1 C2 H2A 122.3
C4 C3 C2 123.5(5)
C4 C3 O1 118.5(6)
C2 C3 O1 117.8(6)
C3 C4 C5 118.9(5)
C3 C4 H4A 120.6
C5 C4 H4A 120.6
C6 C5 C4 121.5(6)
C6 C5 H5A 119.2
C4 C5 H5A 119.2
C5 C6 C1 118.4(6)
C5 C6 H6A 120.8
C1 C6 H6A 120.8
O2 C7 N1 128.5(4)
O2 C7 O1 122.5(4)
N1 C7 O1 109.0(4)
C9 C8 C13 118.8(4)
C9 C8 N1 118.1(4)
C13 C8 N1 123.0(4)
C8 C9 C10 121.4(4)
C8 C9 H9A 119.3
C10 C9 H9A 119.3
C11 C10 C9 117.7(4)
C11 C10 H10A 121.2
C9 C10 H10A 121.2
C12 C11 C10 123.0(4)
C12 C11 F1 118.9(4)
C10 C11 F1 118.1(4)
C11 C12 C13 119.8(4)
C11 C12 H12A 120.1
C13 C12 H12A 120.1
C12 C13 C8 119.2(4)
C12 C13 H13A 120.4
C8 C13 H13A 120.4
C19 C14 C15 120.5(5)
C19 C14 H14A 119.7
C15 C14 H14A 119.7
C14 C15 C16 121.0(5)
C14 C15 H15A 119.5
C16 C15 H15A 119.5
C17 C16 C15 118.7(4)
C17 C16 H16A 120.6
C15 C16 H16A 120.6
C16 C17 C18 120.9(4)
C16 C17 O3 121.9(5)
C18 C17 O3 117.0(4)
C17 C18 C19 119.7(4)
C17 C18 H18A 120.1
C19 C18 H18A 120.1
C14 C19 C18 119.0(5)
C14 C19 H19A 120.5
C18 C19 H19A 120.5
O4 C20 N2 127.1(4)
O4 C20 O3 124.4(4)
N2 C20 O3 108.3(3)
C26 C21 C22 120.3(4)
C26 C21 N2 117.4(3)
C22 C21 N2 122.3(4)
C21 C22 C23 119.4(4)
C21 C22 H22A 120.3
C23 C22 H22A 120.3
C24 C23 C22 119.6(4)
C24 C23 H23A 120.2
C22 C23 H23A 120.2
C23 C24 F2 119.6(4)
C23 C24 C25 122.3(4)
F2 C24 C25 118.1(4)
C24 C25 C26 118.1(4)
C24 C25 H25A 121.0
C26 C25 H25A 121.0
C21 C26 C25 120.2(4)
C21 C26 H26A 119.9
C25 C26 H26A 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.325(5)
N1 C8 1.413(4)
N1 H1A 0.8600
N2 C20 1.340(4)
N2 C21 1.417(4)
N2 H2C 0.8600
F1 C11 1.371(4)
F2 C24 1.358(4)
O1 C3 1.399(5)
O1 C7 1.359(4)
O2 C7 1.198(4)
O3 C17 1.396(5)
O3 C20 1.351(4)
O4 C20 1.204(4)
C1 C6 1.361(7)
C1 C2 1.400(6)
C1 H1B 0.9300
C2 C3 1.355(6)
C2 H2A 0.9300
C3 C4 1.349(6)
C4 C5 1.353(6)
C4 H4A 0.9300
C5 C6 1.348(7)
C5 H5A 0.9300
C6 H6A 0.9300
C8 C9 1.373(5)
C8 C13 1.388(5)
C9 C10 1.379(5)
C9 H9A 0.9300
C10 C11 1.354(5)
C10 H10A 0.9300
C11 C12 1.335(5)
C12 C13 1.384(5)
C12 H12A 0.9300
C13 H13A 0.9300
C14 C19 1.354(6)
C14 C15 1.357(6)
C14 H14A 0.9300
C15 C16 1.385(6)
C15 H15A 0.9300
C16 C17 1.347(5)
C16 H16A 0.9300
C17 C18 1.374(5)
C18 C19 1.393(6)
C18 H18A 0.9300
C19 H19A 0.9300
C21 C26 1.368(5)
C21 C22 1.377(5)
C22 C23 1.377(5)
C22 H22A 0.9300
C23 C24 1.341(5)
C23 H23A 0.9300
C24 C25 1.377(6)
C25 C26 1.381(5)
C25 H25A 0.9300
C26 H26A 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 H1A O4 1_445 0.86 2.32 3.044(4) 142.00
N2 H2C O2 . 0.86 2.08 2.931(4) 171.00
C19 H19A Cg2 1_565 0.93 2.94 3.644(4) 133.71
C23 H23A Cg1 1_665 0.93 2.97 3.710(5) 137.68
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
C6 C1 C2 C3 -1.2(7)
C1 C2 C3 C4 1.7(7)
C1 C2 C3 O1 -173.0(4)
C7 O1 C3 C4 67.3(6)
C7 O1 C3 C2 -117.7(5)
C2 C3 C4 C5 -2.0(7)
O1 C3 C4 C5 172.7(4)
C3 C4 C5 C6 1.8(7)
C4 C5 C6 C1 -1.3(8)
C2 C1 C6 C5 1.1(8)
C8 N1 C7 O2 -4.2(9)
C8 N1 C7 O1 177.7(4)
C3 O1 C7 O2 7.6(8)
C3 O1 C7 N1 -174.2(4)
C7 N1 C8 C9 176.8(5)
C7 N1 C8 C13 -4.7(7)
C13 C8 C9 C10 -1.1(7)
N1 C8 C9 C10 177.5(4)
C8 C9 C10 C11 -0.1(7)
C9 C10 C11 C12 0.6(7)
C9 C10 C11 F1 -180.0(4)
C10 C11 C12 C13 0.0(8)
F1 C11 C12 C13 -179.4(4)
C11 C12 C13 C8 -1.1(7)
C9 C8 C13 C12 1.6(7)
N1 C8 C13 C12 -176.9(4)
C19 C14 C15 C16 -0.6(7)
C14 C15 C16 C17 -0.7(6)
C15 C16 C17 C18 2.3(6)
C15 C16 C17 O3 -173.0(3)
C20 O3 C17 C16 -63.8(6)
C20 O3 C17 C18 120.8(4)
C16 C17 C18 C19 -2.6(6)
O3 C17 C18 C19 172.9(4)
C15 C14 C19 C18 0.3(7)
C17 C18 C19 C14 1.3(6)
C21 N2 C20 O4 -5.8(8)
C21 N2 C20 O3 170.2(4)
C17 O3 C20 O4 -15.0(7)
C17 O3 C20 N2 168.9(4)
C20 N2 C21 C26 -150.6(4)
C20 N2 C21 C22 31.2(6)
C26 C21 C22 C23 4.0(6)
N2 C21 C22 C23 -177.8(4)
C21 C22 C23 C24 -1.9(7)
C22 C23 C24 F2 -179.7(4)
C22 C23 C24 C25 -1.2(8)
C23 C24 C25 C26 2.1(7)
F2 C24 C25 C26 -179.4(4)
C22 C21 C26 C25 -3.1(6)
N2 C21 C26 C25 178.6(4)
C24 C25 C26 C21 0.1(7)