#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/29/2222960.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_2222960
loop_
_publ_author_name
'Mehmood, Tahir'
'Zaidi, Javid H.'
'Jones, Peter G.'
_publ_section_title
;
 tert-Butyl
 N-[1-diazoacetyl-3-(methylsulfanyl)propyl]carbamate
;
_journal_coeditor_code           AT2855
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2120
_journal_page_last               o2121
_journal_paper_doi               10.1107/S1600536809030815
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H19 N3 O3 S'
_chemical_formula_moiety         'C11 H19 N3 O3 S'
_chemical_formula_sum            'C11 H19 N3 O3 S'
_chemical_formula_weight         273.35
_chemical_name_common            Butoxymethionyldiazomethane
_chemical_name_systematic
;
tert-Butyl N-[1-diazoacetyl-3-(methylsulfanyl)propyl]carbamate
;
_space_group_IT_number           144
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_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                120.00
_cell_formula_units_Z            3
_cell_length_a                   9.7915(3)
_cell_length_b                   9.7915(3)
_cell_length_c                   13.8581(5)
_cell_measurement_reflns_used    14422
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.6851
_cell_measurement_theta_min      3.1893
_cell_volume                     1150.62(6)
_computing_cell_refinement
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3543
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Nova A'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16152
_diffrn_reflns_theta_full        72.50
_diffrn_reflns_theta_max         75.59
_diffrn_reflns_theta_min         5.22
_exptl_absorpt_coefficient_mu    1.930
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             438
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.138
_refine_ls_abs_structure_details 'Flack (1983), 1474 Freidel pairs'
_refine_ls_abs_structure_Flack   0.023(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         3073
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0227
_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)+(0.0342P)²+0.1663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0602
_refine_ls_wR_factor_ref         0.0604
_reflns_number_gt                3051
_reflns_number_total             3073
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2855.cif
_cod_data_source_block           I
_cod_database_code               2222960
_cod_database_fobs_code          2222960
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
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
S S 0.08692(4) -0.10432(4) 0.14682(2) 0.03648(9) Uani d . 1 . .
O O1 0.57182(11) 0.62115(10) 0.24352(6) 0.02868(19) Uani d . 1 . .
O O2 0.57776(11) 0.51506(10) 0.38885(6) 0.02855(19) Uani d . 1 . .
O O3 0.66256(11) 0.16891(11) 0.38136(6) 0.02857(19) Uani d . 1 . .
N N1 0.49938(13) 0.36907(12) 0.25188(8) 0.0259(2) Uani d . 1 . .
H H01 0.4999(17) 0.3757(17) 0.1913(12) 0.021(3) Uiso d . 1 . .
N N2 0.88980(14) 0.31145(15) 0.24685(9) 0.0340(3) Uani d . 1 . .
N N3 1.00277(17) 0.3112(2) 0.25596(10) 0.0492(4) Uani d . 1 . .
C C1 0.76526(17) 0.85794(16) 0.33133(11) 0.0350(3) Uani d . 1 . .
H H1A 0.7632 0.7991 0.3890 0.052 Uiso calc R 1 . .
H H1B 0.7907 0.9647 0.3499 0.052 Uiso calc R 1 . .
H H1C 0.8455 0.8640 0.2865 0.052 Uiso calc R 1 . .
C C2 0.60734(19) 0.86229(16) 0.19163(11) 0.0369(3) Uani d . 1 . .
H H2A 0.6887 0.8685 0.1477 0.055 Uiso calc R 1 . .
H H2B 0.6307 0.9690 0.2085 0.055 Uiso calc R 1 . .
H H2C 0.5042 0.8059 0.1600 0.055 Uiso calc R 1 . .
C C3 0.47294(18) 0.75163(17) 0.35029(12) 0.0364(3) Uani d . 1 . .
H H3A 0.3714 0.6914 0.3172 0.055 Uiso calc R 1 . .
H H3B 0.4883 0.8548 0.3693 0.055 Uiso calc R 1 . .
H H3C 0.4739 0.6940 0.4079 0.055 Uiso calc R 1 . .
C C4 0.60502(15) 0.77449(14) 0.28283(10) 0.0278(3) Uani d . 1 . .
C C5 0.55262(14) 0.50412(13) 0.30286(9) 0.0244(2) Uani d . 1 . .
C C6 0.48307(14) 0.22893(14) 0.29774(9) 0.0240(2) Uani d . 1 . .
H H6 0.4329 0.2173 0.3624 0.029 Uiso calc R 1 . .
C C7 0.64131(14) 0.23513(13) 0.31215(9) 0.0234(2) Uani d . 1 . .
C C8 0.75513(15) 0.31186(15) 0.23793(10) 0.0288(3) Uani d . 1 . .
H H8 0.7356 0.3609 0.1847 0.035 Uiso calc R 1 . .
C C9 0.37572(14) 0.08310(13) 0.23693(9) 0.0257(2) Uani d . 1 . .
H H9A 0.4220 0.0957 0.1718 0.031 Uiso calc R 1 . .
H H9B 0.3707 -0.0110 0.2670 0.031 Uiso calc R 1 . .
C C10 0.20871(15) 0.05652(15) 0.22743(10) 0.0300(3) Uani d . 1 . .
H H10A 0.2144 0.1544 0.2032 0.036 Uiso calc R 1 . .
H H10B 0.1588 0.0339 0.2920 0.036 Uiso calc R 1 . .
C C11 0.0623(2) -0.26955(18) 0.21754(14) 0.0502(4) Uani d . 1 . .
H H11A 0.1660 -0.2559 0.2331 0.075 Uiso calc R 1 . .
H H11B 0.0012 -0.3671 0.1806 0.075 Uiso calc R 1 . .
H H11C 0.0062 -0.2755 0.2774 0.075 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C11 S C10 . . 100.36(7) ?
C5 O1 C4 . . 120.53(10) ?
C5 N1 C6 . . 120.23(11) ?
N3 N2 C8 . . 178.84(15) ?
O1 C4 C1 . . 110.78(10) ?
O1 C4 C3 . . 109.87(10) ?
C1 C4 C3 . . 112.46(12) ?
O1 C4 C2 . . 101.65(10) ?
C1 C4 C2 . . 110.15(11) ?
C3 C4 C2 . . 111.43(11) ?
O2 C5 O1 . . 126.21(10) ?
O2 C5 N1 . . 124.23(11) ?
O1 C5 N1 . . 109.57(11) ?
N1 C6 C7 . . 112.93(10) ?
N1 C6 C9 . . 109.93(10) ?
C7 C6 C9 . . 108.48(9) ?
O3 C7 C8 . . 123.12(12) ?
O3 C7 C6 . . 120.91(11) ?
C8 C7 C6 . . 115.84(11) ?
N2 C8 C7 . . 116.62(12) ?
C10 C9 C6 . . 112.51(10) ?
C9 C10 S . . 112.65(9) ?
C5 N1 H01 . . 117.4(10) ?
C6 N1 H01 . . 120.3(10) ?
C4 C1 H1A . . 109.5 ?
C4 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C4 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C4 C2 H2A . . 109.5 ?
C4 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C4 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C4 C3 H3A . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C4 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
N1 C6 H6 . . 108.5 ?
C7 C6 H6 . . 108.5 ?
C9 C6 H6 . . 108.5 ?
N2 C8 H8 . . 121.7 ?
C7 C8 H8 . . 121.7 ?
C10 C9 H9A . . 109.1 ?
C6 C9 H9A . . 109.1 ?
C10 C9 H9B . . 109.1 ?
C6 C9 H9B . . 109.1 ?
H9A C9 H9B . . 107.8 ?
C9 C10 H10A . . 109.1 ?
S C10 H10A . . 109.1 ?
C9 C10 H10B . . 109.1 ?
S C10 H10B . . 109.1 ?
H10A C10 H10B . . 107.8 ?
S C11 H11A . . 109.5 ?
S C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
S C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 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
S C11 . 1.8015(17) ?
S C10 . 1.8089(13) ?
O1 C5 . 1.3450(14) ?
O1 C4 . 1.4727(14) ?
O2 C5 . 1.2107(16) ?
O3 C7 . 1.2323(15) ?
N1 C5 . 1.3528(15) ?
N1 C6 . 1.4468(15) ?
N2 N3 . 1.1145(18) ?
N2 C8 . 1.3264(18) ?
C1 C4 . 1.5163(19) ?
C2 C4 . 1.5223(19) ?
C3 C4 . 1.5189(19) ?
C6 C7 . 1.5330(17) ?
C6 C9 . 1.5340(16) ?
C7 C8 . 1.4237(17) ?
C9 C10 . 1.5276(17) ?
N1 H01 . 0.842(16) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C2 H2A . 0.9800 ?
C2 H2B . 0.9800 ?
C2 H2C . 0.9800 ?
C3 H3A . 0.9800 ?
C3 H3B . 0.9800 ?
C3 H3C . 0.9800 ?
C6 H6 . 1.0000 ?
C8 H8 . 0.9500 ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
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 H01 O3 3_664 0.842(16) 2.027(16) 2.8465(14) 164.1(14)
C8 H8 O2 3_664 0.95 2.51 2.9686(16) 110.0
C11 H11B O2 3_554 0.98 2.52 3.457(2) 159.6
C3 H3B O3 1_565 0.98 2.67 3.5693(17) 152.0
C1 H1C S 1_665 0.98 2.95 3.9281(16) 177.2
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
C5 O1 C4 C1 . . . . 66.13(15) ?
C5 O1 C4 C3 . . . . -58.74(14) ?
C5 O1 C4 C2 . . . . -176.85(11) ?
C4 O1 C5 O2 . . . . -9.28(19) ?
C4 O1 C5 N1 . . . . 170.45(10) ?
C6 N1 C5 O2 . . . . -5.96(19) ?
C6 N1 C5 O1 . . . . 174.30(10) ?
C5 N1 C6 C7 . . . . -76.13(14) ?
C5 N1 C6 C9 . . . . 162.57(10) ?
N1 C6 C7 O3 . . . . 148.43(11) ?
C9 C6 C7 O3 . . . . -89.46(13) ?
N1 C6 C7 C8 . . . . -35.64(15) ?
C9 C6 C7 C8 . . . . 86.47(12) ?
O3 C7 C8 N2 . . . . -0.93(19) ?
C6 C7 C8 N2 . . . . -176.76(11) ?
N1 C6 C9 C10 . . . . -62.16(13) ?
C7 C6 C9 C10 . . . . 173.92(10) ?
C6 C9 C10 S . . . . 174.67(9) ?
C11 S C10 C9 . . . . 69.91(11) ?
