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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
tert-Butyl 4-cyanophenyl carbonate
;
_chemical_name_common     'tboc benzonitrile'
_chemical_formula_moiety     'C12 H13 N O3'
_chemical_formula_sum     'C12 H13 N O3'
_chemical_formula_iupac     'C12 H13 N O3'
_chemical_formula_weight     219.23
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     5.7347(7)
_cell_length_b     14.3237(16)
_cell_length_c     13.7727(16)
_cell_angle_alpha     90.00
_cell_angle_beta     101.1100(10)
_cell_angle_gamma     90.00
_cell_volume     1110.1(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3143
_cell_measurement_theta_min     2.844
_cell_measurement_theta_max     27.482
_cell_measurement_temperature     296(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.312
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     464
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.9586
_exptl_absorpt_correction_T_max     0.9887
_exptl_special_details     ?
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEX CCD area-detector'
_diffrn_measurement_method     'ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6536
_diffrn_reflns_av_R_equivalents     0.0165
_diffrn_reflns_av_sigmaI/netI     0.0194
_diffrn_reflns_theta_min     2.07
_diffrn_reflns_theta_max     27.90
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.915
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     .
_refine_special_details     ?
_reflns_number_total     2427
_reflns_number_gt     2100
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0397
_refine_ls_R_factor_gt     0.0342
_refine_ls_wR_factor_gt     0.0868
_refine_ls_wR_factor_ref     0.0905
_refine_ls_goodness_of_fit_ref     1.048
_refine_ls_restrained_S_all     1.048
_refine_ls_number_reflns     2427
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0448P)²+0.3462P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.306
_refine_diff_density_min     -0.230
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
X-SEED (Barbour, 2001; Atwood & Barbour, 2003)
;
_computing_publication_material
;
X-SEED (Barbour, 2001; Atwood & Barbour, 2003)
;
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_disorder_assembly
    _atom_site_disorder_group
    N N1 0.33241(18) 0.70351(7) 0.16270(7) 0.0241(2) Uani d . 1 . .
    C C2 0.4174(2) 0.69212(8) 0.24446(8) 0.0182(2) Uani d . 1 . .
    C C3 0.52163(19) 0.67936(8) 0.34783(8) 0.0163(2) Uani d . 1 . .
    C C4 0.74719(19) 0.71664(8) 0.38553(8) 0.0180(2) Uani d . 1 . .
    H H4 0.8322 0.7469 0.3438 0.022 Uiso calc R 1 . .
    C C5 0.84213(19) 0.70792(8) 0.48552(8) 0.0187(2) Uani d . 1 . .
    H H5 0.9911 0.7325 0.5117 0.022 Uiso calc R 1 . .
    C C6 0.7118(2) 0.66212(8) 0.54586(8) 0.0170(2) Uani d . 1 . .
    C C7 0.4902(2) 0.62391(8) 0.50998(8) 0.0187(2) Uani d . 1 . .
    H H7 0.4072 0.5931 0.5521 0.022 Uiso calc R 1 . .
    C C8 0.3944(2) 0.63258(8) 0.40994(8) 0.0182(2) Uani d . 1 . .
    H H8 0.2459 0.6073 0.3843 0.022 Uiso calc R 1 . .
    O O9 0.79952(14) 0.65945(6) 0.64836(6) 0.0199(2) Uani d . 1 . .
    C C10 0.97513(19) 0.59643(8) 0.68019(8) 0.0159(2) Uani d . 1 . .
    O O11 1.04663(14) 0.53999(6) 0.62887(6) 0.0211(2) Uani d . 1 . .
    O O12 1.04148(14) 0.61088(6) 0.77662(5) 0.01731(19) Uani d . 1 . .
    C C13 1.22277(19) 0.54939(8) 0.83729(8) 0.0161(2) Uani d . 1 . .
    C C14 1.2463(2) 0.59433(9) 0.93865(8) 0.0210(3) Uani d . 1 . .
    H H14A 1.3021 0.6573 0.9359 0.032 Uiso calc R 1 . .
    H H14B 1.3575 0.5594 0.9860 0.032 Uiso calc R 1 . .
    H H14C 1.0943 0.5947 0.9581 0.032 Uiso calc R 1 . .
    C C15 1.1255(2) 0.45053(8) 0.83660(9) 0.0203(2) Uani d . 1 . .
    H H15A 0.9751 0.4516 0.8574 0.030 Uiso calc R 1 . .
    H H15B 1.2350 0.4123 0.8811 0.030 Uiso calc R 1 . .
    H H15C 1.1050 0.4254 0.7709 0.030 Uiso calc R 1 . .
    C C16 1.45548(19) 0.55369(8) 0.79966(8) 0.0189(2) Uani d . 1 . .
    H H16A 1.4385 0.5204 0.7382 0.028 Uiso calc R 1 . .
    H H16B 1.5798 0.5257 0.8475 0.028 Uiso calc R 1 . .
    H H16C 1.4948 0.6177 0.7896 0.028 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 0.0254(5) 0.0257(6) 0.0193(5) -0.0037(4) -0.0003(4) 0.0010(4)
    C2 0.0180(5) 0.0158(5) 0.0206(6) -0.0013(4) 0.0029(4) -0.0008(4)
    C3 0.0179(5) 0.0151(5) 0.0150(5) 0.0023(4) 0.0012(4) -0.0004(4)
    C4 0.0181(5) 0.0186(5) 0.0176(5) -0.0002(4) 0.0039(4) 0.0022(4)
    C5 0.0150(5) 0.0210(6) 0.0189(6) -0.0004(4) 0.0007(4) 0.0001(4)
    C6 0.0187(5) 0.0184(5) 0.0135(5) 0.0058(4) 0.0019(4) 0.0013(4)
    C7 0.0201(5) 0.0181(6) 0.0191(6) 0.0015(4) 0.0070(4) 0.0025(4)
    C8 0.0158(5) 0.0175(5) 0.0207(6) -0.0009(4) 0.0022(4) -0.0012(4)
    O9 0.0201(4) 0.0259(4) 0.0133(4) 0.0071(3) 0.0020(3) 0.0025(3)
    C10 0.0144(5) 0.0171(5) 0.0160(5) -0.0008(4) 0.0029(4) 0.0025(4)
    O11 0.0240(4) 0.0221(4) 0.0167(4) 0.0043(3) 0.0026(3) -0.0016(3)
    O12 0.0181(4) 0.0204(4) 0.0130(4) 0.0056(3) 0.0018(3) 0.0013(3)
    C13 0.0153(5) 0.0179(5) 0.0144(5) 0.0036(4) 0.0008(4) 0.0032(4)
    C14 0.0238(6) 0.0241(6) 0.0144(5) 0.0055(5) 0.0016(4) 0.0012(4)
    C15 0.0192(5) 0.0197(6) 0.0221(6) 0.0001(4) 0.0040(4) 0.0035(4)
    C16 0.0168(5) 0.0191(6) 0.0208(6) 0.0010(4) 0.0037(4) 0.0014(4)
_geom_special_details     ?
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
    N1 C2 . 1.1493(15) ?
    C2 C3 . 1.4455(15) ?
    C3 C8 . 1.3979(16) ?
    C3 C4 . 1.4032(15) ?
    C4 C5 . 1.3855(15) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.3850(16) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.3846(16) ?
    C6 O9 . 1.4049(13) ?
    C7 C8 . 1.3871(16) ?
    C7 H7 . 0.9300 ?
    C8 H8 . 0.9300 ?
    O9 C10 . 1.3605(13) ?
    C10 O11 . 1.1971(14) ?
    C10 O12 . 1.3254(13) ?
    O12 C13 . 1.4899(13) ?
    C13 C14 . 1.5194(15) ?
    C13 C15 . 1.5214(16) ?
    C13 C16 . 1.5231(15) ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    C15 H15A . 0.9600 ?
    C15 H15B . 0.9600 ?
    C15 H15C . 0.9600 ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
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
    N1 C2 C3 . . 178.86(13) ?
    C8 C3 C4 . . 120.57(10) ?
    C8 C3 C2 . . 119.85(10) ?
    C4 C3 C2 . . 119.55(10) ?
    C5 C4 C3 . . 119.42(10) ?
    C5 C4 H4 . . 120.3 ?
    C3 C4 H4 . . 120.3 ?
    C6 C5 C4 . . 119.01(10) ?
    C6 C5 H5 . . 120.5 ?
    C4 C5 H5 . . 120.5 ?
    C7 C6 C5 . . 122.50(10) ?
    C7 C6 O9 . . 118.29(10) ?
    C5 C6 O9 . . 119.07(10) ?
    C6 C7 C8 . . 118.67(10) ?
    C6 C7 H7 . . 120.7 ?
    C8 C7 H7 . . 120.7 ?
    C7 C8 C3 . . 119.82(10) ?
    C7 C8 H8 . . 120.1 ?
    C3 C8 H8 . . 120.1 ?
    C10 O9 C6 . . 116.18(9) ?
    O11 C10 O12 . . 129.21(10) ?
    O11 C10 O9 . . 125.05(10) ?
    O12 C10 O9 . . 105.73(9) ?
    C10 O12 C13 . . 120.28(8) ?
    O12 C13 C14 . . 101.18(8) ?
    O12 C13 C15 . . 109.34(9) ?
    C14 C13 C15 . . 111.57(9) ?
    O12 C13 C16 . . 110.35(9) ?
    C14 C13 C16 . . 111.52(9) ?
    C15 C13 C16 . . 112.32(9) ?
    C13 C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C13 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C13 C15 H15A . . 109.5 ?
    C13 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C13 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C13 C16 H16A . . 109.5 ?
    C13 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C13 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
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
    C8 C3 C4 C5 . . . . -0.93(17) ?
    C2 C3 C4 C5 . . . . 177.14(10) ?
    C3 C4 C5 C6 . . . . 0.27(17) ?
    C4 C5 C6 C7 . . . . 0.48(17) ?
    C4 C5 C6 O9 . . . . -175.16(10) ?
    C5 C6 C7 C8 . . . . -0.55(17) ?
    O9 C6 C7 C8 . . . . 175.12(10) ?
    C6 C7 C8 C3 . . . . -0.12(17) ?
    C4 C3 C8 C7 . . . . 0.86(17) ?
    C2 C3 C8 C7 . . . . -177.20(10) ?
    C7 C6 O9 C10 . . . . 105.80(12) ?
    C5 C6 O9 C10 . . . . -78.37(13) ?
    C6 O9 C10 O11 . . . . -5.43(16) ?
    C6 O9 C10 O12 . . . . 175.49(9) ?
    O11 C10 O12 C13 . . . . -2.85(17) ?
    O9 C10 O12 C13 . . . . 176.18(8) ?
    C10 O12 C13 C14 . . . . 177.84(9) ?
    C10 O12 C13 C15 . . . . -64.35(12) ?
    C10 O12 C13 C16 . . . . 59.67(12) ?
data_global
_journal_date_recd_electronic     2010-09-15
_journal_date_accepted     2010-09-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     10
_journal_page_first     o2681
_journal_page_last     o2681
_journal_paper_category     QO
_journal_coeditor_code     BH2315
_publ_contact_author_name     'Malcolm.J Applewhite'
_publ_contact_author_address
;
Department of Chemistry and Polymer Science
Stellenbosch University
Private Bag X1, Matieland, 7602
South Africa
;
_publ_contact_author_email     malcolma@sun.ac.za
_publ_contact_author_fax     ?
_publ_contact_author_phone      218083597
_publ_section_title
;
tert-Butyl 4-cyanophenyl carbonate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    "Applewhite, Malcolm J." .
;
Department of Chemistry and Polymer Science
Stellenbosch University
Private Bag X1
Matieland 7602
South Africa
;
