#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/71/2227164.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_2227164
loop_
_publ_author_name
'Xia, Cheng-Cai'
_publ_section_title
;
 2,2-Dimethyl-1,3-benzodioxol-4-yl N-methylcarbamate
;
_journal_coeditor_code           BH2301
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2580
_journal_paper_doi               10.1107/S1600536810036123
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H13 N O4'
_chemical_formula_moiety         'C11 H13 N O4'
_chemical_formula_sum            'C11 H13 N O4'
_chemical_formula_weight         223.22
_chemical_melting_point          408
_chemical_name_systematic
;
2,2-Dimethyl-1,3-benzodioxol-4-yl N-methylcarbamate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.326(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.505(6)
_cell_length_b                   9.669(7)
_cell_length_c                   12.355(8)
_cell_measurement_reflns_used    2406
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      2.68
_cell_volume                     1132.2(13)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5692
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_correction_T_min  0.9763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Siemens, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.130
_refine_ls_extinction_coef       0.035(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0354
_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)+(0.0465P)²+0.1766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0975
_reflns_number_gt                1615
_reflns_number_total             2003
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2301.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2227164
_cod_database_fobs_code          2227164
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O O1 0.78908(12) 0.22049(10) 0.73401(10) 0.0666(3) Uani d . 1 . .
O O2 0.91170(11) 0.04289(10) 0.81309(9) 0.0614(3) Uani d . 1 . .
O O3 1.07164(11) 0.14292(11) 0.63309(8) 0.0624(3) Uani d . 1 . .
O O4 1.27901(11) 0.26676(13) 0.65853(9) 0.0707(4) Uani d . 1 . .
N N1 0.69122(14) 0.01063(12) 0.74902(10) 0.0589(4) Uani d . 1 . .
H H1 0.7052 -0.0723 0.7726 0.071 Uiso calc R 1 . .
C C1 0.55627(18) 0.04608(19) 0.69670(16) 0.0748(5) Uani d . 1 . .
H H1A 0.5096 0.1103 0.7412 0.112 Uiso calc R 1 . .
H H1B 0.4999 -0.0360 0.6864 0.112 Uiso calc R 1 . .
H H1C 0.5689 0.0876 0.6275 0.112 Uiso calc R 1 . .
C C2 0.79399(16) 0.10118(14) 0.76185(11) 0.0491(4) Uani d . 1 . .
C C3 1.03134(16) 0.12582(15) 0.82661(12) 0.0537(4) Uani d . 1 . .
C C4 1.10295(15) 0.16741(14) 0.74063(11) 0.0505(4) Uani d . 1 . .
C C5 1.22535(16) 0.24235(16) 0.75644(12) 0.0554(4) Uani d . 1 . .
C C6 1.28072(19) 0.27957(18) 0.85695(14) 0.0674(5) Uani d . 1 . .
H H6 1.3632 0.3313 0.8667 0.081 Uiso calc R 1 . .
C C7 1.2084(2) 0.23669(19) 0.94372(14) 0.0730(5) Uani d . 1 . .
H H7 1.2435 0.2597 1.0137 0.088 Uiso calc R 1 . .
C C8 1.0863(2) 0.16103(17) 0.92966(13) 0.0670(5) Uani d . 1 . .
H H8 1.0402 0.1333 0.9898 0.080 Uiso calc R 1 . .
C C9 1.17105(17) 0.22577(17) 0.57665(13) 0.0602(4) Uani d . 1 . .
C C10 1.2336(2) 0.1358(2) 0.49544(16) 0.0884(6) Uani d . 1 . .
H H10A 1.3010 0.1879 0.4581 0.133 Uiso calc R 1 . .
H H10B 1.1604 0.1029 0.4441 0.133 Uiso calc R 1 . .
H H10C 1.2798 0.0586 0.5316 0.133 Uiso calc R 1 . .
C C11 1.0989(2) 0.35311(19) 0.53297(16) 0.0795(5) Uani d . 1 . .
H H11A 1.0580 0.4014 0.5908 0.119 Uiso calc R 1 . .
H H11B 1.0260 0.3280 0.4785 0.119 Uiso calc R 1 . .
H H11C 1.1662 0.4119 0.5015 0.119 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
C2 O2 C3 . . 116.85(11) ?
C4 O3 C9 . . 105.66(12) ?
C5 O4 C9 . . 106.26(12) ?
C2 N1 C1 . . 121.84(14) ?
C2 N1 H1 . . 119.1 ?
C1 N1 H1 . . 119.1 ?
N1 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
N1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C2 N1 . . 126.32(15) ?
O1 C2 O2 . . 122.75(14) ?
N1 C2 O2 . . 110.93(13) ?
C4 C3 C8 . . 117.95(16) ?
C4 C3 O2 . . 121.84(13) ?
C8 C3 O2 . . 120.08(14) ?
O3 C4 C3 . . 128.60(14) ?
O3 C4 C5 . . 110.59(13) ?
C3 C4 C5 . . 120.80(14) ?
C6 C5 O4 . . 128.11(16) ?
C6 C5 C4 . . 122.36(15) ?
O4 C5 C4 . . 109.50(13) ?
C5 C6 C7 . . 116.66(17) ?
C5 C6 H6 . . 121.7 ?
C7 C6 H6 . . 121.7 ?
C8 C7 C6 . . 121.86(16) ?
C8 C7 H7 . . 119.1 ?
C6 C7 H7 . . 119.1 ?
C7 C8 C3 . . 120.35(16) ?
C7 C8 H8 . . 119.8 ?
C3 C8 H8 . . 119.8 ?
O4 C9 O3 . . 105.58(12) ?
O4 C9 C10 . . 109.58(15) ?
O3 C9 C10 . . 107.98(14) ?
O4 C9 C11 . . 108.10(14) ?
O3 C9 C11 . . 109.30(14) ?
C10 C9 C11 . . 115.83(16) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C9 C11 H11A . . 109.5 ?
C9 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C9 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
O1 C2 . 1.2037(18) ?
O2 C2 . 1.3650(18) ?
O2 C3 . 1.3911(19) ?
O3 C4 . 1.3603(19) ?
O3 C9 . 1.4560(19) ?
O4 C5 . 1.368(2) ?
O4 C9 . 1.441(2) ?
N1 C2 . 1.312(2) ?
N1 C1 . 1.434(2) ?
N1 H1 . 0.8600 ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C3 C4 . 1.365(2) ?
C3 C8 . 1.382(2) ?
C4 C5 . 1.372(2) ?
C5 C6 . 1.360(2) ?
C6 C7 . 1.380(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.372(3) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 C10 . 1.485(2) ?
C9 C11 . 1.490(2) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
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
N1 H1 O1 2_646 0.86 2.01 2.819(3) 157.1 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
C1 N1 C2 O1 . . . . 0.8(2) ?
C1 N1 C2 O2 . . . . -179.66(13) ?
C3 O2 C2 O1 . . . . -3.81(19) ?
C3 O2 C2 N1 . . . . 176.62(12) ?
C2 O2 C3 C4 . . . . -68.19(17) ?
C2 O2 C3 C8 . . . . 116.03(15) ?
C9 O3 C4 C3 . . . . 172.56(15) ?
C9 O3 C4 C5 . . . . -8.60(16) ?
C8 C3 C4 O3 . . . . 178.46(14) ?
O2 C3 C4 O3 . . . . 2.6(2) ?
C8 C3 C4 C5 . . . . -0.3(2) ?
O2 C3 C4 C5 . . . . -176.13(13) ?
C9 O4 C5 C6 . . . . -171.39(16) ?
C9 O4 C5 C4 . . . . 10.45(17) ?
O3 C4 C5 C6 . . . . -179.39(14) ?
C3 C4 C5 C6 . . . . -0.5(2) ?
O3 C4 C5 O4 . . . . -1.11(17) ?
C3 C4 C5 O4 . . . . 177.83(13) ?
O4 C5 C6 C7 . . . . -177.16(15) ?
C4 C5 C6 C7 . . . . 0.8(2) ?
C5 C6 C7 C8 . . . . -0.4(3) ?
C6 C7 C8 C3 . . . . -0.3(3) ?
C4 C3 C8 C7 . . . . 0.6(2) ?
O2 C3 C8 C7 . . . . 176.56(14) ?
C5 O4 C9 O3 . . . . -15.26(16) ?
C5 O4 C9 C10 . . . . -131.32(15) ?
C5 O4 C9 C11 . . . . 101.61(15) ?
C4 O3 C9 O4 . . . . 14.55(15) ?
C4 O3 C9 C10 . . . . 131.69(14) ?
C4 O3 C9 C11 . . . . -101.52(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2224
