#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/71/2227175.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_2227175
loop_
_publ_author_name
'Applewhite, Malcolm J.'
_publ_section_title
;
 tert-Butyl 4-cyanophenyl carbonate
;
_journal_coeditor_code           BH2315
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2681
_journal_paper_doi               10.1107/S1600536810038602
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H13 N O3'
_chemical_formula_moiety         'C12 H13 N O3'
_chemical_formula_sum            'C12 H13 N O3'
_chemical_formula_weight         219.23
_chemical_name_common            'tboc benzonitrile'
_chemical_name_systematic
;
tert-Butyl 4-cyanophenyl carbonate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 101.1100(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7347(7)
_cell_length_b                   14.3237(16)
_cell_length_c                   13.7727(16)
_cell_measurement_reflns_used    3143
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.482
_cell_measurement_theta_min      2.844
_cell_volume                     1110.1(2)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
;
X-SEED (Barbour, 2001; Atwood & Barbour, 2003)
;
_computing_publication_material
;
X-SEED (Barbour, 2001; Atwood & Barbour, 2003)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6536
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         2.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_correction_T_min  0.9586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0342
_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)+(0.0448P)²+0.3462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0905
_reflns_number_gt                2100
_reflns_number_total             2427
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2315.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227175
_cod_database_fobs_code          2227175
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'
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_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_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_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_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) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656179
