#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/18/2201861.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_2201861
loop_
_publ_author_name
'Muir, Kenneth W.'
'Morris, David G.'
_publ_section_title
;
 N,N-Dimethyl-N'-(o-fluorobenzoyl)hydrazide
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o490
_journal_page_last               o492
_journal_paper_doi               10.1107/S1600536803005634
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C9 H11 F1 N2 O1'
_chemical_formula_moiety         'C9 H11 F1 N2 O1'
_chemical_formula_sum            'C9 H11 F N2 O'
_chemical_formula_weight         182.2
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.8503(5)
_cell_length_b                   7.8530(3)
_cell_length_c                   19.9630(9)
_cell_measurement_reflns_used    1794
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.9
_cell_volume                     1857.76(13)
_computing_cell_refinement       'HKL SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'thick-slices ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.057
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6796
_diffrn_reflns_theta_full        25.92
_diffrn_reflns_theta_max         25.92
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.11
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.11
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.048P)²+0.85P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.116
_reflns_number_gt                1491
_reflns_number_total             1797
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf6244.cif
_cod_data_source_block           I
_cod_original_cell_volume        1857.77(13)
_cod_original_formula_sum        'C9 H11 F1 N2 O1'
_cod_database_code               2201861
_cod_database_fobs_code          2201861
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.04440(14) 0.0364(2) 0.31315(8) 0.0242(4) Uani d . 1 . . C
C2 0.01463(14) -0.0441(2) 0.25446(9) 0.0275(4) Uani d . 1 . . C
H2 -0.056 -0.0942 0.2495 0.033 Uiso calc R 1 . . H
C3 0.09321(15) -0.0482(2) 0.20276(8) 0.0285(4) Uani d . 1 . . C
H3 0.0747 -0.0992 0.1622 0.034 Uiso calc R 1 . . H
C4 0.19926(15) 0.0235(2) 0.21152(9) 0.0283(4) Uani d . 1 . . C
H4 0.2516 0.0203 0.1768 0.034 Uiso calc R 1 . . H
C5 0.22732(14) 0.0997(2) 0.27185(8) 0.0252(4) Uani d . 1 . . C
H5 0.2992 0.145 0.2777 0.03 Uiso calc R 1 . . H
C6 0.14924(13) 0.1093(2) 0.32376(8) 0.0217(4) Uani d . 1 . . C
C7 0.17407(14) 0.2139(2) 0.38546(8) 0.0220(4) Uani d . 1 . . C
C8 0.25331(19) 0.1700(3) 0.53962(9) 0.0384(5) Uani d . 1 . . C
H8A 0.1723 0.1678 0.5382 0.058 Uiso calc R 1 . . H
H8B 0.2776 0.2334 0.5781 0.058 Uiso calc R 1 . . H
H8C 0.2815 0.0556 0.5425 0.058 Uiso calc R 1 . . H
C9 0.41985(17) 0.2554(3) 0.47847(10) 0.0395(5) Uani d . 1 . . C
H9A 0.4488 0.1415 0.4814 0.059 Uiso calc R 1 . . H
H9B 0.4462 0.3206 0.5161 0.059 Uiso calc R 1 . . H
H9C 0.4456 0.3073 0.4377 0.059 Uiso calc R 1 . . H
F1 -0.03368(8) 0.04377(14) 0.36335(5) 0.0329(3) Uani d . 1 . . F
N1 0.26030(13) 0.15704(18) 0.42201(7) 0.0253(3) Uani d . 1 . . N
H1 0.2893(17) 0.051(3) 0.4152(10) 0.034(5) Uiso d . 1 . . H
N2 0.29666(13) 0.25077(19) 0.47890(7) 0.0273(4) Uani d . 1 . . N
O1 0.11979(10) 0.34444(15) 0.39699(6) 0.0279(3) Uani d . 1 . . O
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
C1 0.0200(8) 0.0247(8) 0.0278(9) 0.0017(7) 0.0018(7) -0.0009(7)
C2 0.0199(8) 0.0294(9) 0.0332(9) -0.0004(7) -0.0047(7) -0.0045(7)
C3 0.0281(9) 0.0311(9) 0.0263(9) 0.0038(8) -0.0055(7) -0.0055(7)
C4 0.0265(9) 0.0326(9) 0.0260(9) 0.0013(7) 0.0021(7) 0.0004(7)
C5 0.0203(8) 0.0273(9) 0.0280(8) -0.0017(7) -0.0012(7) 0.0005(7)
C6 0.0208(8) 0.0195(8) 0.0248(8) 0.0015(6) -0.0028(7) 0.0013(6)
C7 0.0211(8) 0.0210(8) 0.0239(8) -0.0026(6) 0.0004(6) 0.0020(6)
C8 0.0498(12) 0.0378(10) 0.0275(9) -0.0050(9) -0.0023(9) -0.0040(8)
C9 0.0332(10) 0.0449(11) 0.0405(11) -0.0068(9) -0.0097(9) -0.0056(9)
F1 0.0235(5) 0.0414(6) 0.0338(6) -0.0067(5) 0.0068(4) -0.0083(4)
N1 0.0301(8) 0.0192(7) 0.0267(7) 0.0030(6) -0.0073(6) -0.0043(6)
N2 0.0313(8) 0.0252(7) 0.0254(7) 0.0001(7) -0.0088(6) -0.0043(6)
O1 0.0256(6) 0.0250(6) 0.0331(7) 0.0028(5) -0.0046(5) -0.0053(5)
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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 0.006 '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
F1 C1 C2 118.06(15)
F1 C1 C6 118.58(14)
C2 C1 C6 123.36(16)
C1 C2 C3 118.07(16)
C1 C2 H2 121
C3 C2 H2 121
C4 C3 C2 120.23(16)
C4 C3 H3 119.9
C2 C3 H3 119.9
C5 C4 C3 120.13(16)
C5 C4 H4 119.9
C3 C4 H4 119.9
C4 C5 C6 120.75(16)
C4 C5 H5 119.6
C6 C5 H5 119.6
C1 C6 C5 117.42(15)
C1 C6 C7 121.66(15)
C5 C6 C7 120.50(14)
O1 C7 N1 125.22(15)
O1 C7 C6 120.24(14)
N1 C7 C6 114.46(14)
N2 C8 H8A 109.5
N2 C8 H8B 109.5
H8A C8 H8B 109.5
N2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N2 C9 H9A 109.5
N2 C9 H9B 109.5
H9A C9 H9B 109.5
N2 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C7 N1 N2 119.79(14)
C7 N1 H1 120.9(13)
N2 N1 H1 118.6(13)
N1 N2 C9 108.16(14)
N1 N2 C8 109.36(14)
C9 N2 C8 111.54(15)
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 F1 . 1.3653(19) ?
C1 C2 . 1.377(2) ?
C1 C6 . 1.384(2) ?
C2 C3 . 1.390(3) ?
C2 H2 . 0.93 ?
C3 C4 . 1.388(3) ?
C3 H3 . 0.93 ?
C4 C5 . 1.385(2) ?
C4 H4 . 0.93 ?
C5 C6 . 1.391(2) ?
C5 H5 . 0.93 ?
C6 C7 . 1.509(2) ?
C7 O1 . 1.232(2) ?
C7 N1 . 1.333(2) ?
C8 N2 . 1.462(2) ?
C8 H8A . 0.96 ?
C8 H8B . 0.96 ?
C8 H8C . 0.96 ?
C9 N2 . 1.460(2) ?
C9 H9A . 0.96 ?
C9 H9B . 0.96 ?
C9 H9C . 0.96 ?
N1 N2 . 1.4202(19) ?
N1 H1 . 0.91(2) ?
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 H1 O1 7_655 0.91(2) 1.98(2) 2.8801(19) 168.8(19)
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
F1 C1 C2 C3 178.55(15)
C6 C1 C2 C3 -1.7(3)
C1 C2 C3 C4 1.6(3)
C2 C3 C4 C5 -0.1(3)
C3 C4 C5 C6 -1.6(3)
F1 C1 C6 C5 179.89(14)
C2 C1 C6 C5 0.1(2)
F1 C1 C6 C7 -7.5(2)
C2 C1 C6 C7 172.74(15)
C4 C5 C6 C1 1.5(2)
C4 C5 C6 C7 -171.20(15)
C1 C6 C7 O1 -60.7(2)
C5 C6 C7 O1 111.73(18)
C1 C6 C7 N1 122.50(17)
C5 C6 C7 N1 -65.1(2)
O1 C7 N1 N2 -0.7(3)
C6 C7 N1 N2 175.91(14)
C7 N1 N2 C9 -136.70(17)
C7 N1 N2 C8 101.65(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3651187
