#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/99/2229904.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_2229904
loop_
_publ_author_name
'Şen, Fatih'
'Dinçer, Muharrem'
'Çukurovalı, Alaaddin'
'Yılmaz, Ibrahim'
_publ_section_title
;
 (Z)-1-(3-Mesityl-3-methylcyclobutyl)-2-(morpholin-4-yl)ethanone
 oxime
;
_journal_coeditor_code           ZS2100
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o958
_journal_page_last               o959
_journal_paper_doi               10.1107/S1600536811009408
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H30 N2 O2'
_chemical_formula_moiety         'C20 H30 N2 O2'
_chemical_formula_sum            'C20 H30 N2 O2'
_chemical_formula_weight         330.46
_chemical_melting_point          428
_chemical_name_systematic
;
(Z)-1-(3-Mesityl-3-methylcyclobutyl)-2-(morpholin-4-yl)ethanone oxime
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 126.574(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.0273(4)
_cell_length_b                   10.2337(2)
_cell_length_c                   18.1262(6)
_cell_measurement_reflns_used    29343
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.02
_cell_measurement_theta_min      1.40
_cell_volume                     1940.69(11)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS II CCD area-detector'
_diffrn_measurement_method       'rotation method'
_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  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28812
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9773
_exptl_absorpt_correction_T_min  0.9643
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.547
_exptl_crystal_size_min          0.480
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0517
_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)+(0.0970P)²+0.1596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1609
_refine_ls_wR_factor_ref         0.1710
_reflns_number_gt                3110
_reflns_number_total             4031
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2100.cif
_cod_data_source_block           I
_cod_original_cell_volume        1940.69(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229904
_cod_database_fobs_code          2229904
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_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
C C1 0.36380(14) -0.05777(14) 0.74190(10) 0.0528(4) Uani d . 1 . .
C C2 0.46281(15) -0.05329(16) 0.83667(11) 0.0601(4) Uani d . 1 . .
C C3 0.46390(18) -0.1424(2) 0.89474(12) 0.0715(5) Uani d . 1 . .
H H3 0.5287 -0.1366 0.9575 0.086 Uiso calc R 1 . .
C C4 0.3733(2) -0.2391(2) 0.86371(15) 0.0758(5) Uani d . 1 . .
C C5 0.28345(19) -0.24910(18) 0.77046(15) 0.0752(5) Uani d . 1 . .
H H5 0.2242 -0.3167 0.7476 0.090 Uiso calc R 1 . .
C C6 0.27696(16) -0.16278(16) 0.70854(12) 0.0625(4) Uani d . 1 . .
C C7 0.1786(2) -0.1905(2) 0.60720(14) 0.0886(6) Uani d . 1 . .
H H7A 0.1295 -0.2660 0.5997 0.133 Uiso calc R 1 . .
H H7B 0.2212 -0.2066 0.5794 0.133 Uiso calc R 1 . .
H H7C 0.1229 -0.1166 0.5782 0.133 Uiso calc R 1 . .
C C8 0.57461(17) 0.0403(2) 0.87941(14) 0.0814(6) Uani d . 1 . .
H H8A 0.5632 0.0968 0.8328 0.122 Uiso calc R 1 . .
H H8B 0.6524 -0.0084 0.9071 0.122 Uiso calc R 1 . .
H H8C 0.5790 0.0918 0.9255 0.122 Uiso calc R 1 . .
C C9 0.3761(3) -0.3317(3) 0.9297(2) 0.1137(9) Uani d . 1 . .
H H9A 0.4450 -0.3083 0.9916 0.171 Uiso calc R 1 . .
H H9B 0.3885 -0.4194 0.9175 0.171 Uiso calc R 1 . .
H H9C 0.2966 -0.3265 0.9219 0.171 Uiso calc R 1 . .
C C10 0.4242(2) 0.0076(2) 0.63806(16) 0.0834(6) Uani d . 1 . .
H H10A 0.4154 0.0753 0.5979 0.125 Uiso calc R 1 . .
H H10B 0.3894 -0.0724 0.6042 0.125 Uiso calc R 1 . .
H H10C 0.5131 -0.0045 0.6874 0.125 Uiso calc R 1 . .
C C11 0.35215(14) 0.04679(15) 0.67740(11) 0.0556(4) Uani d . 1 . .
C C12 0.38414(15) 0.18873(15) 0.71533(12) 0.0603(4) Uani d . 1 . .
H H12A 0.3857 0.2003 0.7691 0.072 Uiso calc R 1 . .
H H12B 0.4617 0.2227 0.7263 0.072 Uiso calc R 1 . .
C C13 0.26170(15) 0.24003(16) 0.62660(12) 0.0612(4) Uani d . 1 . .
H H13 0.2804 0.2744 0.5853 0.073 Uiso calc R 1 . .
C C14 0.21439(16) 0.09740(16) 0.60114(11) 0.0622(4) Uani d . 1 . .
H H14A 0.1840 0.0734 0.5394 0.075 Uiso calc R 1 . .
H H14B 0.1520 0.0746 0.6119 0.075 Uiso calc R 1 . .
C C15 0.18063(15) 0.33490(15) 0.63429(12) 0.0597(4) Uani d . 1 . .
C C16 0.18719(17) 0.34202(17) 0.71954(13) 0.0659(4) Uani d . 1 . .
H H16A 0.2731 0.3658 0.7713 0.079 Uiso calc R 1 . .
H H16B 0.1291 0.4090 0.7123 0.079 Uiso calc R 1 . .
C C17 0.01643(17) 0.1917(2) 0.67605(14) 0.0768(5) Uani d . 1 . .
H H17A -0.0136 0.1987 0.6127 0.092 Uiso calc R 1 . .
H H17B -0.0288 0.2556 0.6863 0.092 Uiso calc R 1 . .
C C18 -0.0090(2) 0.0568(3) 0.69414(19) 0.0989(7) Uani d . 1 . .
H H18A -0.1000 0.0394 0.6532 0.119 Uiso calc R 1 . .
H H18B 0.0338 -0.0066 0.6813 0.119 Uiso calc R 1 . .
C C19 0.1671(3) 0.0674(3) 0.84584(18) 0.1042(8) Uani d . 1 . .
H H19A 0.2119 0.0042 0.8346 0.125 Uiso calc R 1 . .
H H19B 0.1968 0.0574 0.9089 0.125 Uiso calc R 1 . .
C C20 0.1967(2) 0.2022(2) 0.83206(14) 0.0853(6) Uani d . 1 . .
H H20A 0.1544 0.2658 0.8451 0.102 Uiso calc R 1 . .
H H20B 0.2881 0.2175 0.8738 0.102 Uiso calc R 1 . .
N N1 0.09976(13) 0.41245(15) 0.57100(11) 0.0688(4) Uani d . 1 . .
N N2 0.15302(12) 0.21666(14) 0.73755(9) 0.0607(4) Uani d . 1 . .
O O1 0.09479(13) 0.40408(15) 0.49164(10) 0.0860(5) Uani d . 1 . .
H H1 0.0415 0.4558 0.4531 0.129 Uiso calc R 1 . .
O O2 0.03433(18) 0.0426(2) 0.78590(14) 0.1121(6) 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 0.0033 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 C1 C6 . . 117.83(14) ?
C2 C1 C11 . . 120.93(14) ?
C6 C1 C11 . . 121.24(14) ?
C3 C2 C1 . . 119.55(16) ?
C3 C2 C8 . . 117.12(16) ?
C1 C2 C8 . . 123.24(16) ?
C4 C3 C2 . . 122.95(17) ?
C4 C3 H3 . . 118.5 ?
C2 C3 H3 . . 118.5 ?
C5 C4 C3 . . 116.83(17) ?
C5 C4 C9 . . 122.0(2) ?
C3 C4 C9 . . 121.2(2) ?
C4 C5 C6 . . 122.97(18) ?
C4 C5 H5 . . 118.5 ?
C6 C5 H5 . . 118.5 ?
C5 C6 C1 . . 119.40(16) ?
C5 C6 C7 . . 117.43(17) ?
C1 C6 C7 . . 123.12(16) ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C2 C8 H8A . . 109.5 ?
C2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C4 C9 H9A . . 109.5 ?
C4 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C4 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C11 C10 H10A . . 109.5 ?
C11 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C11 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C1 C11 C10 . . 111.39(13) ?
C1 C11 C12 . . 116.03(14) ?
C10 C11 C12 . . 111.90(15) ?
C1 C11 C14 . . 116.62(13) ?
C10 C11 C14 . . 111.97(15) ?
C12 C11 C14 . . 86.87(11) ?
C13 C12 C11 . . 91.08(12) ?
C13 C12 H12A . . 113.5 ?
C11 C12 H12A . . 113.5 ?
C13 C12 H12B . . 113.5 ?
C11 C12 H12B . . 113.5 ?
H12A C12 H12B . . 110.8 ?
C15 C13 C12 . . 118.29(15) ?
C15 C13 C14 . . 117.48(14) ?
C12 C13 C14 . . 88.30(12) ?
C15 C13 H13 . . 110.3 ?
C12 C13 H13 . . 110.3 ?
C14 C13 H13 . . 110.3 ?
C13 C14 C11 . . 90.31(12) ?
C13 C14 H14A . . 113.6 ?
C11 C14 H14A . . 113.6 ?
C13 C14 H14B . . 113.6 ?
C11 C14 H14B . . 113.6 ?
H14A C14 H14B . . 110.9 ?
N1 C15 C16 . . 114.07(15) ?
N1 C15 C13 . . 124.80(17) ?
C16 C15 C13 . . 121.10(13) ?
N2 C16 C15 . . 110.55(14) ?
N2 C16 H16A . . 109.5 ?
C15 C16 H16A . . 109.5 ?
N2 C16 H16B . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 108.1 ?
N2 C17 C18 . . 108.85(16) ?
N2 C17 H17A . . 109.9 ?
C18 C17 H17A . . 109.9 ?
N2 C17 H17B . . 109.9 ?
C18 C17 H17B . . 109.9 ?
H17A C17 H17B . . 108.3 ?
O2 C18 C17 . . 111.6(2) ?
O2 C18 H18A . . 109.3 ?
C17 C18 H18A . . 109.3 ?
O2 C18 H18B . . 109.3 ?
C17 C18 H18B . . 109.3 ?
H18A C18 H18B . . 108.0 ?
O2 C19 C20 . . 110.93(19) ?
O2 C19 H19A . . 109.5 ?
C20 C19 H19A . . 109.5 ?
O2 C19 H19B . . 109.5 ?
C20 C19 H19B . . 109.5 ?
H19A C19 H19B . . 108.0 ?
N2 C20 C19 . . 109.40(19) ?
N2 C20 H20A . . 109.8 ?
C19 C20 H20A . . 109.8 ?
N2 C20 H20B . . 109.8 ?
C19 C20 H20B . . 109.8 ?
H20A C20 H20B . . 108.2 ?
C15 N1 O1 . . 113.21(15) ?
C17 N2 C20 . . 109.05(15) ?
C17 N2 C16 . . 112.40(13) ?
C20 N2 C16 . . 113.32(16) ?
N1 O1 H1 . . 109.5 ?
C18 O2 C19 . . 109.51(16) ?
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 C2 . 1.406(2) ?
C1 C6 . 1.409(2) ?
C1 C11 . 1.524(2) ?
C2 C3 . 1.386(3) ?
C2 C8 . 1.515(3) ?
C3 C4 . 1.378(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.371(3) ?
C4 C9 . 1.509(3) ?
C5 C6 . 1.391(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.514(3) ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C11 . 1.533(2) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 C12 . 1.554(2) ?
C11 C14 . 1.563(2) ?
C12 C13 . 1.533(2) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C15 . 1.501(2) ?
C13 C14 . 1.544(2) ?
C13 H13 . 0.9800 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 N1 . 1.271(2) ?
C15 C16 . 1.498(3) ?
C16 N2 . 1.457(2) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 N2 . 1.453(2) ?
C17 C18 . 1.500(3) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 O2 . 1.410(3) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 O2 . 1.414(3) ?
C19 C20 . 1.493(4) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 N2 . 1.456(2) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
N1 O1 . 1.404(2) ?
O1 H1 . 0.8200 ?
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
O1 H1 N1 3_566 0.82 2.11 2.7944(19) 141
C16 H16B O2 2_556 0.97 2.55 3.494(2) 165
C19 H19B O1 4_566 0.97 2.56 3.305(3) 134
C12 H12B Cg1 2_645 0.97 2.84 3.777(3) 161
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
C6 C1 C2 C3 . . . . -6.9(2) ?
C11 C1 C2 C3 . . . . 173.84(15) ?
C6 C1 C2 C8 . . . . 169.57(16) ?
C11 C1 C2 C8 . . . . -9.6(2) ?
C1 C2 C3 C4 . . . . 1.8(3) ?
C8 C2 C3 C4 . . . . -174.94(18) ?
C2 C3 C4 C5 . . . . 3.5(3) ?
C2 C3 C4 C9 . . . . -178.3(2) ?
C3 C4 C5 C6 . . . . -3.6(3) ?
C9 C4 C5 C6 . . . . 178.3(2) ?
C4 C5 C6 C1 . . . . -1.6(3) ?
C4 C5 C6 C7 . . . . 175.97(19) ?
C2 C1 C6 C5 . . . . 6.9(2) ?
C11 C1 C6 C5 . . . . -173.91(15) ?
C2 C1 C6 C7 . . . . -170.59(17) ?
C11 C1 C6 C7 . . . . 8.6(3) ?
C2 C1 C11 C10 . . . . 91.37(19) ?
C6 C1 C11 C10 . . . . -87.81(19) ?
C2 C1 C11 C12 . . . . -38.2(2) ?
C6 C1 C11 C12 . . . . 142.60(15) ?
C2 C1 C11 C14 . . . . -138.40(15) ?
C6 C1 C11 C14 . . . . 42.4(2) ?
C1 C11 C12 C13 . . . . -132.15(13) ?
C10 C11 C12 C13 . . . . 98.51(15) ?
C14 C11 C12 C13 . . . . -13.94(13) ?
C11 C12 C13 C15 . . . . 134.65(15) ?
C11 C12 C13 C14 . . . . 14.10(13) ?
C15 C13 C14 C11 . . . . -135.28(15) ?
C12 C13 C14 C11 . . . . -14.01(13) ?
C1 C11 C14 C13 . . . . 131.49(14) ?
C10 C11 C14 C13 . . . . -98.55(16) ?
C12 C11 C14 C13 . . . . 13.83(13) ?
C12 C13 C15 N1 . . . . 159.02(16) ?
C14 C13 C15 N1 . . . . -97.0(2) ?
C12 C13 C15 C16 . . . . -22.9(2) ?
C14 C13 C15 C16 . . . . 81.1(2) ?
N1 C15 C16 N2 . . . . 118.59(16) ?
C13 C15 C16 N2 . . . . -59.7(2) ?
N2 C17 C18 O2 . . . . 59.1(2) ?
O2 C19 C20 N2 . . . . -59.6(3) ?
C16 C15 N1 O1 . . . . -179.84(14) ?
C13 C15 N1 O1 . . . . -1.6(2) ?
C18 C17 N2 C20 . . . . -58.0(2) ?
C18 C17 N2 C16 . . . . 175.45(18) ?
C19 C20 N2 C17 . . . . 58.7(2) ?
C19 C20 N2 C16 . . . . -175.29(17) ?
C15 C16 N2 C17 . . . . -74.95(18) ?
C15 C16 N2 C20 . . . . 160.85(15) ?
C17 C18 O2 C19 . . . . -59.2(3) ?
C20 C19 O2 C18 . . . . 59.2(3) ?
