#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/04/2220487.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_2220487
loop_
_publ_author_name
'Sang, Guang-Ming'
'Luo, Shi-Neng'
'Lin, Jian-Guo'
'Yang, Hai-Lin'
'Xia, Yong-Mei'
_publ_section_title
;
 2-(1-Methylethoxy)-5-nitrophenyl N-methylcarbamate
;
_journal_coeditor_code           FJ2175
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o47
_journal_paper_doi               10.1107/S1600536808040622
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H14 N2 O5'
_chemical_formula_moiety         'C11 H14 N2 O5'
_chemical_formula_sum            'C11 H14 N2 O5'
_chemical_formula_weight         254.24
_chemical_name_systematic
;
2-(1-Methylethoxy)-5-nitrophenyl N-methylcarbamate
;
_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                91.361(3)
_cell_angle_beta                 97.492(2)
_cell_angle_gamma                94.6930(10)
_cell_formula_units_Z            2
_cell_length_a                   5.034(2)
_cell_length_b                   10.4221(16)
_cell_length_c                   12.6319(12)
_cell_measurement_reflns_used    825
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      25.43
_cell_measurement_theta_min      2.11
_cell_volume                     654.5(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7186
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.213
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0486
_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)+(0.04P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                2005
_reflns_number_total             3172
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2175.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2220487
_cod_database_fobs_code          2220487
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6429(3) 1.05070(14) 0.65269(13) 0.0418(3) Uani d . 1 . .
C C2 0.4552(3) 1.04573(14) 0.72651(12) 0.0408(3) Uani d . 1 . .
H H2 0.4010 1.1205 0.7557 0.049 Uiso calc R 1 . .
C C3 0.3576(3) 0.92824(15) 0.75300(12) 0.0401(3) Uani d . 1 . .
C C4 0.4281(3) 0.81480(14) 0.70606(12) 0.0404(3) Uani d . 1 . .
C C5 0.6183(3) 0.82349(14) 0.63360(12) 0.0410(3) Uani d . 1 . .
H H5 0.6732 0.7492 0.6039 0.049 Uiso calc R 1 . .
C C6 0.7215(3) 0.94193(14) 0.60731(12) 0.0412(3) Uani d . 1 . .
H H6 0.8450 0.9487 0.5586 0.049 Uiso calc R 1 . .
C C7 0.4126(3) 0.58077(15) 0.71348(12) 0.0419(3) Uani d . 1 . .
H H7 0.6049 0.5905 0.7068 0.050 Uiso calc R 1 . .
C C8 0.3506(4) 0.49615(16) 0.80518(15) 0.0503(4) Uani d . 1 . .
H H8A 0.4181 0.5406 0.8719 0.075 Uiso calc R 1 . .
H H8B 0.4351 0.4173 0.8004 0.075 Uiso calc R 1 . .
H H8C 0.1596 0.4772 0.8011 0.075 Uiso calc R 1 . .
C C9 0.2464(4) 0.52696(15) 0.61402(13) 0.0475(4) Uani d . 1 . .
H H9A 0.0596 0.5236 0.6231 0.071 Uiso calc R 1 . .
H H9B 0.2939 0.4417 0.5990 0.071 Uiso calc R 1 . .
H H9C 0.2783 0.5809 0.5556 0.071 Uiso calc R 1 . .
C C10 0.2341(3) 0.86019(14) 0.91676(12) 0.0379(3) Uani d . 1 . .
C C11 0.0362(3) 0.77353(16) 1.06731(13) 0.0446(4) Uani d . 1 . .
H H11A 0.1398 0.7002 1.0669 0.067 Uiso calc R 1 . .
H H11B -0.1414 0.7466 1.0827 0.067 Uiso calc R 1 . .
H H11C 0.1217 0.8356 1.1211 0.067 Uiso calc R 1 . .
N N1 0.7563(3) 1.17674(12) 0.62443(11) 0.0435(3) Uani d . 1 . .
N N2 0.0186(3) 0.83114(12) 0.96365(10) 0.0403(3) Uani d . 1 . .
H H2A -0.1364 0.8468 0.9318 0.048 Uiso calc R 1 . .
O O1 0.6715(2) 1.27246(10) 0.66209(9) 0.0473(3) Uani d . 1 . .
O O2 0.9315(2) 1.18325(10) 0.56528(9) 0.0446(3) Uani d . 1 . .
O O3 0.3060(2) 0.70444(10) 0.73769(9) 0.0420(3) Uani d . 1 . .
O O4 0.1650(2) 0.91925(10) 0.82168(9) 0.0418(3) Uani d . 1 . .
O O5 0.4638(2) 0.84188(10) 0.95050(9) 0.0421(3) Uani d . 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
C6 C1 C2 . . 122.26(14) ?
C6 C1 N1 . . 119.34(15) ?
C2 C1 N1 . . 118.40(14) ?
C3 C2 C1 . . 117.29(14) ?
C3 C2 H2 . . 121.4 ?
C1 C2 H2 . . 121.4 ?
C2 C3 O4 . . 119.06(13) ?
C2 C3 C4 . . 122.00(15) ?
O4 C3 C4 . . 118.72(13) ?
O3 C4 C3 . . 115.20(14) ?
O3 C4 C5 . . 125.76(13) ?
C3 C4 C5 . . 119.03(14) ?
C6 C5 C4 . . 119.41(14) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C5 C6 C1 . . 119.92(15) ?
C5 C6 H6 . . 120.0 ?
C1 C6 H6 . . 120.0 ?
O3 C7 C9 . . 106.04(13) ?
O3 C7 C8 . . 104.34(12) ?
C9 C7 C8 . . 108.30(15) ?
O3 C7 H7 . . 112.5 ?
C9 C7 H7 . . 112.5 ?
C8 C7 H7 . . 112.5 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
O5 C10 N2 . . 126.72(15) ?
O5 C10 O4 . . 122.87(14) ?
N2 C10 O4 . . 110.40(13) ?
N2 C11 H11A . . 109.5 ?
N2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
N2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O1 N1 O2 . . 122.72(13) ?
O1 N1 C1 . . 117.78(13) ?
O2 N1 C1 . . 119.50(13) ?
C10 N2 C11 . . 121.78(13) ?
C10 N2 H2A . . 119.1 ?
C11 N2 H2A . . 119.1 ?
C4 O3 C7 . . 118.97(12) ?
C10 O4 C3 . . 116.28(12) ?
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
C1 C6 . 1.368(2) ?
C1 C2 . 1.410(2) ?
C1 N1 . 1.4600(19) ?
C2 C3 . 1.348(2) ?
C2 H2 . 0.9300 ?
C3 O4 . 1.3818(18) ?
C3 C4 . 1.402(2) ?
C4 O3 . 1.3530(19) ?
C4 C5 . 1.408(2) ?
C5 C6 . 1.365(2) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O3 . 1.4766(18) ?
C7 C9 . 1.486(2) ?
C7 C8 . 1.521(2) ?
C7 H7 . 0.9800 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 O5 . 1.2107(18) ?
C10 N2 . 1.3195(18) ?
C10 O4 . 1.3797(19) ?
C11 N2 . 1.4487(19) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
N1 O1 . 1.2263(17) ?
N1 O2 . 1.2270(17) ?
N2 H2A . 0.8600 ?
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
_geom_hbond_publ_flag
N2 H2A O5 1_455 0.86 2.05 2.788(2) 143 yes
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
C6 C1 C2 C3 . . . . 1.2(2) ?
N1 C1 C2 C3 . . . . -178.66(15) ?
C1 C2 C3 O4 . . . . -177.36(14) ?
C1 C2 C3 C4 . . . . -2.9(2) ?
C2 C3 C4 O3 . . . . -177.54(14) ?
O4 C3 C4 O3 . . . . -3.1(2) ?
C2 C3 C4 C5 . . . . 3.7(3) ?
O4 C3 C4 C5 . . . . 178.15(14) ?
O3 C4 C5 C6 . . . . 178.71(15) ?
C3 C4 C5 C6 . . . . -2.7(2) ?
C4 C5 C6 C1 . . . . 1.1(3) ?
C2 C1 C6 C5 . . . . -0.3(3) ?
N1 C1 C6 C5 . . . . 179.56(14) ?
C6 C1 N1 O1 . . . . 176.26(14) ?
C2 C1 N1 O1 . . . . -3.8(2) ?
C6 C1 N1 O2 . . . . -4.2(2) ?
C2 C1 N1 O2 . . . . 175.73(15) ?
O5 C10 N2 C11 . . . . 1.4(2) ?
O4 C10 N2 C11 . . . . -177.13(13) ?
C3 C4 O3 C7 . . . . -165.57(13) ?
C5 C4 O3 C7 . . . . 13.1(2) ?
C9 C7 O3 C4 . . . . -96.64(16) ?
C8 C7 O3 C4 . . . . 149.11(14) ?
O5 C10 O4 C3 . . . . 15.7(2) ?
N2 C10 O4 C3 . . . . -165.71(12) ?
C2 C3 O4 C10 . . . . -118.54(16) ?
C4 C3 O4 C10 . . . . 66.83(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741324
