#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/60/2206085.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_2206085
loop_
_publ_author_name
'Zhao, Li-Fang'
_publ_section_title
;
 2-(Cyclopropyliminomethyl)-4-nitrophenol
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1670
_journal_page_last               o1671
_journal_paper_doi               10.1107/S1600536805014145
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C10 H10 N2 O3'
_chemical_formula_moiety         'C10 H10 N2 O3'
_chemical_formula_sum            'C10 H10 N2 O3'
_chemical_formula_weight         206.20
_chemical_name_systematic
;
2-(Cyclopropyliminomethyl)-4-nitrophenol
;
_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                 97.599(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.800(2)
_cell_length_b                   5.845(2)
_cell_length_c                   21.610(3)
_cell_measurement_reflns_used    2043
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.54
_cell_measurement_theta_min      2.63
_cell_volume                     976.6(4)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 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  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7544
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9854
_exptl_absorpt_correction_T_min  0.9741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.317
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2022
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0549
_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)+(0.0587P)²+0.2047P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1361
_reflns_number_gt                1694
_reflns_number_total             2022
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su6201.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_original_cell_volume        976.6(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2206085
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_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_type_symbol
O1 0.4591(2) 1.4388(3) 0.58930(7) 0.0670(5) Uani d . 1 O
O2 0.3451(2) 1.2372(3) 0.65605(7) 0.0771(5) Uani d . 1 O
O3 0.10989(19) 0.6631(2) 0.41891(6) 0.0547(4) Uani d D 1 O
N1 0.3727(2) 1.2762(3) 0.60290(7) 0.0494(4) Uani d . 1 N
N2 0.2233(2) 0.9255(3) 0.33760(7) 0.0442(4) Uani d . 1 N
C1 0.3014(2) 1.1201(3) 0.55368(8) 0.0393(4) Uani d . 1 C
C2 0.2180(2) 0.9241(3) 0.56979(8) 0.0449(5) Uani d . 1 C
H2 0.2052 0.8958 0.6113 0.054 Uiso calc R 1 H
C3 0.1548(2) 0.7727(3) 0.52426(9) 0.0464(5) Uani d . 1 C
H3A 0.0994 0.6402 0.5349 0.056 Uiso calc R 1 H
C4 0.1726(2) 0.8151(3) 0.46216(8) 0.0404(4) Uani d . 1 C
C5 0.2557(2) 1.0179(3) 0.44587(8) 0.0371(4) Uani d . 1 C
C6 0.3199(2) 1.1688(3) 0.49263(8) 0.0384(4) Uani d . 1 C
H6 0.3752 1.3024 0.4828 0.046 Uiso calc R 1 H
C7 0.2760(2) 1.0653(3) 0.38106(8) 0.0416(4) Uani d . 1 C
H7 0.3287 1.2009 0.3713 0.050 Uiso calc R 1 H
C8 0.2521(3) 0.9740(4) 0.27513(8) 0.0478(5) Uani d . 1 C
H8 0.3049 1.1220 0.2677 0.057 Uiso calc R 1 H
C9 0.2977(3) 0.7776(4) 0.23666(10) 0.0689(7) Uani d . 1 C
H9A 0.3783 0.8053 0.2070 0.083 Uiso calc R 1 H
H9B 0.3067 0.6276 0.2560 0.083 Uiso calc R 1 H
C10 0.1243(3) 0.8811(4) 0.22371(9) 0.0606(6) Uani d . 1 C
H10A 0.0271 0.7947 0.2352 0.073 Uiso calc R 1 H
H10B 0.0988 0.9723 0.1861 0.073 Uiso calc R 1 H
H3 0.134(3) 0.721(4) 0.3822(7) 0.080 Uiso d D 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0845(12) 0.0542(9) 0.0588(10) -0.0142(8) -0.0032(8) -0.0081(7)
O2 0.1040(13) 0.0919(13) 0.0355(8) -0.0088(10) 0.0093(8) -0.0114(8)
O3 0.0682(9) 0.0483(8) 0.0465(8) -0.0178(7) 0.0038(7) -0.0028(6)
N1 0.0543(10) 0.0525(10) 0.0397(9) 0.0091(8) 0.0004(7) -0.0050(7)
N2 0.0501(9) 0.0481(9) 0.0342(8) 0.0009(7) 0.0051(7) 0.0004(7)
C1 0.0375(9) 0.0441(10) 0.0357(9) 0.0074(8) 0.0018(7) -0.0023(8)
C2 0.0445(10) 0.0553(11) 0.0350(9) 0.0071(8) 0.0062(8) 0.0075(8)
C3 0.0477(11) 0.0462(11) 0.0449(10) -0.0042(8) 0.0055(8) 0.0098(8)
C4 0.0389(9) 0.0401(10) 0.0413(10) 0.0000(7) 0.0022(7) 0.0011(8)
C5 0.0348(9) 0.0398(9) 0.0366(9) 0.0040(7) 0.0045(7) 0.0022(7)
C6 0.0376(9) 0.0374(9) 0.0402(9) 0.0014(7) 0.0046(7) 0.0011(7)
C7 0.0434(10) 0.0421(10) 0.0392(10) -0.0017(8) 0.0059(8) 0.0035(8)
C8 0.0525(11) 0.0557(12) 0.0352(9) -0.0030(9) 0.0058(8) 0.0018(8)
C9 0.0855(17) 0.0758(16) 0.0449(12) 0.0199(13) 0.0066(11) -0.0092(11)
C10 0.0643(13) 0.0737(15) 0.0413(11) -0.0065(11) -0.0019(10) -0.0009(10)
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
C4 O3 H3 105.4(17)
O2 N1 O1 122.96(18)
O2 N1 C1 118.28(18)
O1 N1 C1 118.75(16)
C7 N2 C8 119.70(17)
C6 C1 C2 121.64(17)
C6 C1 N1 119.56(17)
C2 C1 N1 118.80(16)
C3 C2 C1 119.47(16)
C3 C2 H2 120.3
C1 C2 H2 120.3
C2 C3 C4 120.47(17)
C2 C3 H3A 119.8
C4 C3 H3A 119.8
O3 C4 C3 118.90(17)
O3 C4 C5 121.32(16)
C3 C4 C5 119.78(17)
C6 C5 C4 118.97(16)
C6 C5 C7 120.40(16)
C4 C5 C7 120.63(16)
C1 C6 C5 119.67(17)
C1 C6 H6 120.2
C5 C6 H6 120.2
N2 C7 C5 121.48(17)
N2 C7 H7 119.3
C5 C7 H7 119.3
N2 C8 C9 117.04(18)
N2 C8 C10 117.32(17)
C9 C8 C10 59.27(15)
N2 C8 H8 116.9
C9 C8 H8 116.9
C10 C8 H8 116.9
C10 C9 C8 60.57(14)
C10 C9 H9A 117.7
C8 C9 H9A 117.7
C10 C9 H9B 117.7
C8 C9 H9B 117.7
H9A C9 H9B 114.8
C9 C10 C8 60.17(14)
C9 C10 H10A 117.8
C8 C10 H10A 117.8
C9 C10 H10B 117.8
C8 C10 H10B 117.8
H10A C10 H10B 114.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.223(2)
O2 N1 1.218(2)
O3 C4 1.335(2)
O3 H3 0.904(10)
N1 C1 1.455(2)
N2 C7 1.272(2)
N2 C8 1.426(2)
C1 C6 1.375(2)
C1 C2 1.384(3)
C2 C3 1.366(3)
C2 H2 0.9300
C3 C4 1.390(2)
C3 H3A 0.9300
C4 C5 1.418(3)
C5 C6 1.384(2)
C5 C7 1.457(2)
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.488(3)
C8 C10 1.494(3)
C8 H8 0.9800
C9 C10 1.474(3)
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9700
C10 H10B 0.9700
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3 N2 0.900(10) 1.739(15) 2.576(2) 153(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
O2 N1 C1 C6 175.36(17)
O1 N1 C1 C6 -5.5(3)
O2 N1 C1 C2 -5.4(3)
O1 N1 C1 C2 173.78(17)
C6 C1 C2 C3 1.1(3)
N1 C1 C2 C3 -178.12(16)
C1 C2 C3 C4 -0.5(3)
C2 C3 C4 O3 179.74(17)
C2 C3 C4 C5 -0.5(3)
O3 C4 C5 C6 -179.38(16)
C3 C4 C5 C6 0.9(3)
O3 C4 C5 C7 -0.4(3)
C3 C4 C5 C7 179.87(16)
C2 C1 C6 C5 -0.7(3)
N1 C1 C6 C5 178.49(15)
C4 C5 C6 C1 -0.3(2)
C7 C5 C6 C1 -179.25(16)
C8 N2 C7 C5 -177.43(16)
C6 C5 C7 N2 177.58(17)
C4 C5 C7 N2 -1.4(3)
C7 N2 C8 C9 141.5(2)
C7 N2 C8 C10 -150.94(19)
N2 C8 C9 C10 107.2(2)
N2 C8 C10 C9 -106.7(2)
