#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/87/2228734.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_2228734
loop_
_publ_author_name
'Li, Yu-Feng'
_publ_section_title
;
 Methyl 3-(2-furylmethylidene)carbazate
;
_journal_coeditor_code           HB5763
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o64
_journal_paper_doi               10.1107/S1600536810051019
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C7 H8 N2 O3'
_chemical_formula_moiety         'C7 H8 N2 O3'
_chemical_formula_sum            'C7 H8 N2 O3'
_chemical_formula_weight         168.15
_chemical_name_systematic
;
Methyl 3-(2-furylmethylidene)carbazate
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 104.11(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.668(5)
_cell_length_b                   7.7356(15)
_cell_length_c                   14.720(3)
_cell_measurement_reflns_used    3695
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.17
_cell_volume                     1619.8(8)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'phi and omega 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  0.1171
_diffrn_reflns_av_sigmaI/netI    0.1634
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7823
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.283
_refine_ls_abs_structure_details none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3695
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.890
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0716
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1692
_refine_ls_wR_factor_ref         0.1858
_reflns_number_gt                2600
_reflns_number_total             3695
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5763.cif
_cod_data_source_block           I
_cod_original_cell_volume        1619.8(7)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2228734
_cod_database_fobs_code          2228734
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
O O5 0.18498(16) 0.9708(3) 0.08083(14) 0.0286(5) Uani d . 1 . .
N N4 0.22925(19) 0.8558(3) 0.25908(17) 0.0242(5) Uani d . 1 . .
N N3 0.1797(2) 0.7585(3) 0.18594(17) 0.0281(6) Uani d . 1 . .
H H3A 0.1595 0.6572 0.1951 0.034 Uiso calc R 1 . .
O O4 0.33569(18) 1.0262(3) 0.41175(15) 0.0358(6) Uani d . 1 . .
O O6 0.1200(2) 0.7115(3) 0.03597(15) 0.0397(7) Uani d . 1 . .
C C8 0.2972(2) 0.8690(4) 0.4211(2) 0.0276(7) Uani d . 1 . .
C C12 0.2438(2) 0.7836(4) 0.3391(2) 0.0260(7) Uani d . 1 . .
H H12A 0.2194 0.6741 0.3443 0.031 Uiso calc R 1 . .
C C13 0.1635(2) 0.8259(4) 0.0994(2) 0.0261(7) Uani d . 1 . .
C C9 0.3199(3) 0.8194(5) 0.5124(2) 0.0376(9) Uani d . 1 . .
H H9A 0.3020 0.7180 0.5371 0.045 Uiso calc R 1 . .
C C14 0.0973(4) 0.7748(5) -0.0591(2) 0.0489(11) Uani d . 1 . .
H H14A 0.0666 0.6853 -0.1005 0.073 Uiso calc R 1 . .
H H14B 0.1539 0.8086 -0.0759 0.073 Uiso calc R 1 . .
H H14C 0.0562 0.8728 -0.0640 0.073 Uiso calc R 1 . .
C C11 0.3764(3) 0.9529(6) 0.5622(2) 0.0419(9) Uani d . 1 . .
H H11A 0.4032 0.9564 0.6263 0.050 Uiso calc R 1 . .
C C10 0.3839(3) 1.0730(6) 0.4994(2) 0.0421(9) Uani d . 1 . .
H H10A 0.4176 1.1754 0.5137 0.051 Uiso calc R 1 . .
O O2 0.04032(17) 0.4665(3) 0.19917(14) 0.0296(5) Uani d . 1 . .
N N1 0.1456(2) 0.2564(4) 0.18947(19) 0.0291(6) Uani d . 1 . .
H H1A 0.1539 0.1531 0.1715 0.035 Uiso calc R 1 . .
N N2 0.22041(19) 0.3544(3) 0.23547(17) 0.0265(6) Uani d . 1 . .
C C6 0.0590(2) 0.3252(4) 0.1731(2) 0.0272(7) Uani d . 1 . .
O O3 -0.00370(18) 0.2153(3) 0.12255(17) 0.0371(6) Uani d . 1 . .
C C5 0.3004(2) 0.2814(4) 0.2473(2) 0.0264(7) Uani d . 1 . .
H H5A 0.3037 0.1687 0.2264 0.032 Uiso calc R 1 . .
O O1 0.37821(19) 0.5284(3) 0.3290(2) 0.0509(8) Uani d . 1 . .
C C1 0.3852(2) 0.3697(4) 0.2920(2) 0.0282(7) Uani d . 1 . .
C C2 0.4759(3) 0.3280(5) 0.3040(2) 0.0348(8) Uani d . 1 . .
H H2B 0.4995 0.2257 0.2857 0.042 Uiso calc R 1 . .
C C7 -0.0995(3) 0.2726(6) 0.0996(3) 0.0501(10) Uani d . 1 . .
H H7A -0.1386 0.1857 0.0629 0.075 Uiso calc R 1 . .
H H7B -0.1046 0.3780 0.0644 0.075 Uiso calc R 1 . .
H H7C -0.1194 0.2924 0.1562 0.075 Uiso calc R 1 . .
C C4 0.5291(3) 0.4693(6) 0.3499(3) 0.0463(10) Uani d . 1 . .
H H4B 0.5943 0.4781 0.3669 0.056 Uiso calc R 1 . .
C C3 0.4682(3) 0.5862(6) 0.3638(3) 0.0587(13) Uani d . 1 . .
H H3B 0.4842 0.6924 0.3929 0.070 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
C12 N4 N3 . . 115.1(3) ?
C13 N3 N4 . . 118.1(3) ?
C13 N3 H3A . . 121.0 ?
N4 N3 H3A . . 121.0 ?
C10 O4 C8 . . 105.9(3) ?
C13 O6 C14 . . 114.4(3) ?
C9 C8 O4 . . 110.1(3) ?
C9 C8 C12 . . 131.0(3) ?
O4 C8 C12 . . 118.9(3) ?
N4 C12 C8 . . 120.8(3) ?
N4 C12 H12A . . 119.6 ?
C8 C12 H12A . . 119.6 ?
O5 C13 O6 . . 124.2(3) ?
O5 C13 N3 . . 125.2(3) ?
O6 C13 N3 . . 110.6(3) ?
C8 C9 C11 . . 106.2(3) ?
C8 C9 H9A . . 126.9 ?
C11 C9 H9A . . 126.9 ?
O6 C14 H14A . . 109.5 ?
O6 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O6 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C10 C11 C9 . . 106.6(3) ?
C10 C11 H11A . . 126.7 ?
C9 C11 H11A . . 126.7 ?
C11 C10 O4 . . 111.1(4) ?
C11 C10 H10A . . 124.4 ?
O4 C10 H10A . . 124.4 ?
C6 N1 N2 . . 118.5(3) ?
C6 N1 H1A . . 120.7 ?
N2 N1 H1A . . 120.7 ?
C5 N2 N1 . . 115.0(3) ?
O2 C6 O3 . . 124.8(3) ?
O2 C6 N1 . . 125.3(3) ?
O3 C6 N1 . . 109.9(3) ?
C6 O3 C7 . . 115.9(3) ?
N2 C5 C1 . . 121.2(3) ?
N2 C5 H5A . . 119.4 ?
C1 C5 H5A . . 119.4 ?
C1 O1 C3 . . 106.6(3) ?
C2 C1 O1 . . 109.6(3) ?
C2 C1 C5 . . 132.1(3) ?
O1 C1 C5 . . 118.4(3) ?
C1 C2 C4 . . 106.9(3) ?
C1 C2 H2B . . 126.5 ?
C4 C2 H2B . . 126.5 ?
O3 C7 H7A . . 109.5 ?
O3 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O3 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C3 C4 C2 . . 106.8(3) ?
C3 C4 H4B . . 126.6 ?
C2 C4 H4B . . 126.6 ?
C4 C3 O1 . . 110.2(4) ?
C4 C3 H3B . . 124.9 ?
O1 C3 H3B . . 124.9 ?
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
O5 C13 . 1.214(4) ?
N4 C12 . 1.273(4) ?
N4 N3 . 1.368(3) ?
N3 C13 . 1.343(4) ?
N3 H3A . 0.8600 ?
O4 C10 . 1.360(4) ?
O4 C8 . 1.361(4) ?
O6 C13 . 1.331(4) ?
O6 C14 . 1.442(4) ?
C8 C9 . 1.359(4) ?
C8 C12 . 1.430(4) ?
C12 H12A . 0.9300 ?
C9 C11 . 1.412(6) ?
C9 H9A . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C11 C10 . 1.334(6) ?
C11 H11A . 0.9300 ?
C10 H10A . 0.9300 ?
O2 C6 . 1.211(4) ?
N1 C6 . 1.344(4) ?
N1 N2 . 1.369(4) ?
N1 H1A . 0.8600 ?
N2 C5 . 1.275(4) ?
C6 O3 . 1.338(4) ?
O3 C7 . 1.432(5) ?
C5 C1 . 1.431(4) ?
C5 H5A . 0.9300 ?
O1 C1 . 1.357(4) ?
O1 C3 . 1.370(5) ?
C1 C2 . 1.339(5) ?
C2 C4 . 1.414(6) ?
C2 H2B . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C4 C3 . 1.321(6) ?
C4 H4B . 0.9300 ?
C3 H3B . 0.9300 ?
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 H1A O5 1_545 0.86 2.07 2.867(4) 155
N3 H3A O2 . 0.86 2.30 3.085(4) 152
N3 H3A N2 . 0.86 2.53 3.232(3) 140
