#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/94/2239437.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_2239437
loop_
_publ_author_name
'Bugenhagen, Bernhard'
'Al Jasem, Yosef'
'Al-Azani, Mariam'
'Thiemann, Thies'
_publ_section_title
;
 Fluoren-9-one oxime
;
_journal_coeditor_code           GK2601
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o265
_journal_paper_doi               10.1107/S1600536814002669
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C13 H9 N O'
_chemical_formula_moiety         'C13 H9 N O'
_chemical_formula_sum            'C13 H9 N O'
_chemical_formula_weight         195.21
_chemical_melting_point_gt       471
_chemical_melting_point_lt       472
_chemical_name_common            'Fluorenone oxime'
_chemical_name_systematic
;
Fluoren-9-one oxime
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_method
;
  Olex2 1.2
  (compiled 2013.04.25 svn.r2679, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.80090(10)
_cell_length_b                   12.2309(2)
_cell_length_c                   16.0247(3)
_cell_measurement_reflns_used    3850
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      76.0550
_cell_measurement_theta_min      4.5280
_cell_volume                     940.96(3)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2013)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) within OLEX2 (Dolomanov et al.,
2009)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100.0(10)
_diffrn_detector_area_resol_mean 10.4127
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9884
_diffrn_measurement_device_type  'Agilent SuperNova (Dual, Cu at zero, Atlas)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7588
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.339
_diffrn_reflns_theta_min         4.548
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.175
_refine_ls_abs_structure_details
;
Flack parameter determined using 735 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   0.16(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0384P)²+0.1723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0745
_reflns_number_gt                1865
_reflns_number_total             1942
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2601sup1.cif
_cod_data_source_block           I
_cod_database_code               2239437
_cod_database_fobs_code          2239437
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           .2013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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'
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_occupancy
C C1 0.5506(4) 0.58330(13) 0.40422(10) 0.0189(4) Uani d 1
C C10 0.8197(4) 0.44386(15) 0.17647(10) 0.0251(4) Uani d 1
C C11 0.9543(4) 0.53953(15) 0.20052(10) 0.0242(4) Uani d 1
C C12 0.8830(4) 0.59306(14) 0.27456(10) 0.0219(4) Uani d 1
C C13 0.6741(4) 0.54803(13) 0.32367(10) 0.0196(3) Uani d 1
C C2 0.3367(4) 0.50126(13) 0.42679(10) 0.0194(3) Uani d 1
C C3 0.1613(4) 0.49391(13) 0.49503(10) 0.0209(3) Uani d 1
C C4 -0.0178(4) 0.40413(13) 0.50050(11) 0.0228(4) Uani d 1
C C5 -0.0177(4) 0.32387(14) 0.43891(11) 0.0246(4) Uani d 1
C C6 0.1590(4) 0.33133(14) 0.37017(11) 0.0235(4) Uani d 1
C C7 0.3353(4) 0.42037(13) 0.36414(10) 0.0195(3) Uani d 1
C C8 0.5403(4) 0.45037(13) 0.30001(10) 0.0198(4) Uani d 1
C C9 0.6112(4) 0.39797(14) 0.22607(11) 0.0239(4) Uani d 1
H H1 0.898(6) 0.773(2) 0.4668(17) 0.068(9) Uiso d 1
H H10 0.8703 0.4093 0.1256 0.030 Uiso calc 1
H H11 1.0969 0.5689 0.1661 0.029 Uiso calc 1
H H12 0.9750 0.6584 0.2908 0.026 Uiso calc 1
H H3 0.1626 0.5485 0.5372 0.025 Uiso calc 1
H H4 -0.1408 0.3978 0.5467 0.027 Uiso calc 1
H H5 -0.1399 0.2631 0.4438 0.029 Uiso calc 1
H H6 0.1583 0.2764 0.3283 0.028 Uiso calc 1
H H9 0.5200 0.3325 0.2097 0.029 Uiso calc 1
N N1 0.6059(3) 0.66488(11) 0.45230(8) 0.0202(3) Uani d 1
O O1 0.8178(3) 0.73127(10) 0.42014(7) 0.0233(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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 6 6 0.0594
-3 0 -1 0.0529
0 -6 -6 0.0581
3 1 2 0.0695
-1 6 -6 0.0572
-2 5 6 0.0659
0 -4 9 0.0754
1 -6 6 0.0762
2 -4 -8 0.0670
-2 4 5 0.0676
0 8 2 0.0653
2 5 -4 0.0723
3 -2 -6 0.0564
0 -8 -2 0.0732
-2 -6 2 0.0804
-2 -4 4 0.0804
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 O1 H1 107.7(17)
C1 N1 O1 112.25(13)
N1 C1 C2 121.43(15)
N1 C1 C13 131.53(16)
C2 C1 C13 107.00(14)
C3 C2 C1 131.26(15)
C3 C2 C7 120.97(15)
C7 C2 C1 107.75(14)
C2 C3 H3 120.8
C2 C3 C4 118.38(15)
C4 C3 H3 120.8
C3 C4 H4 119.7
C5 C4 C3 120.63(16)
C5 C4 H4 119.7
C4 C5 H5 119.5
C4 C5 C6 120.97(17)
C6 C5 H5 119.5
C5 C6 H6 120.7
C7 C6 C5 118.66(16)
C7 C6 H6 120.7
C2 C7 C8 108.64(14)
C6 C7 C2 120.39(16)
C6 C7 C8 130.96(16)
C9 C8 C7 130.19(16)
C9 C8 C13 120.61(16)
C13 C8 C7 109.20(14)
C8 C9 H9 120.8
C8 C9 C10 118.41(16)
C10 C9 H9 120.8
C9 C10 H10 119.6
C11 C10 C9 120.89(16)
C11 C10 H10 119.6
C10 C11 H11 119.5
C10 C11 C12 121.04(17)
C12 C11 H11 119.5
C11 C12 H12 120.9
C13 C12 C11 118.17(17)
C13 C12 H12 120.9
C8 C13 C1 107.38(15)
C12 C13 C1 131.75(16)
C12 C13 C8 120.87(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C13 1.484(2)
C1 C2 1.481(2)
C10 C11 1.391(3)
C10 H10 0.9500
C11 C12 1.398(2)
C11 H11 0.9500
C12 C13 1.389(2)
C12 H12 0.9500
C2 C7 1.410(2)
C2 C3 1.383(2)
C3 C4 1.397(2)
C3 H3 0.9500
C4 C5 1.392(2)
C4 H4 0.9500
C5 C6 1.393(2)
C5 H5 0.9500
C6 C7 1.383(2)
C6 H6 0.9500
C7 C8 1.469(2)
C8 C13 1.408(2)
C8 C9 1.389(2)
C9 C10 1.396(3)
C9 H9 0.9500
N1 C1 1.288(2)
O1 H1 0.98(3)
O1 N1 1.4000(19)
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
C12 H12 O1 1_555 0.95 2.38 2.898(2) 114
O1 H1 N1 3_566 0.98(3) 1.80(3) 2.7758(18) 169(3)
C5 H5 Cg1 3_456 0.95 3.076 3.873 142
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
O1 N1 C1 C2 178.85(14)
O1 N1 C1 C13 1.2(2)
N1 C1 C2 C3 1.5(3)
N1 C1 C2 C7 -177.14(15)
N1 C1 C13 C8 177.82(17)
N1 C1 C13 C12 -1.4(3)
C1 C2 C3 C4 -178.52(16)
C1 C2 C7 C6 178.38(15)
C1 C2 C7 C8 -1.52(18)
C2 C1 C13 C8 -0.04(18)
C2 C1 C13 C12 -179.28(17)
C2 C3 C4 C5 0.4(2)
C2 C7 C8 C9 -178.86(18)
C2 C7 C8 C13 1.53(18)
C3 C2 C7 C6 -0.5(2)
C3 C2 C7 C8 179.64(15)
C3 C4 C5 C6 -0.4(3)
C4 C5 C6 C7 0.0(3)
C5 C6 C7 C2 0.5(3)
C5 C6 C7 C8 -179.68(17)
C6 C7 C8 C9 1.3(3)
C6 C7 C8 C13 -178.35(18)
C7 C2 C3 C4 0.0(2)
C7 C8 C9 C10 -178.93(17)
C7 C8 C13 C1 -0.88(18)
C7 C8 C13 C12 178.46(15)
C8 C9 C10 C11 0.3(3)
C9 C8 C13 C1 179.46(15)
C9 C8 C13 C12 -1.2(2)
C9 C10 C11 C12 -0.6(3)
C10 C11 C12 C13 0.1(3)
C11 C12 C13 C1 179.97(17)
C11 C12 C13 C8 0.8(2)
C13 C1 C2 C3 179.66(16)
C13 C1 C2 C7 0.98(18)
C13 C8 C9 C10 0.6(2)
