#------------------------------------------------------------------------------
#$Date: 2016-02-20 04:06:23 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/52/2205200.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_2205200
loop_
_publ_author_name
'Quail, J. Wilson'
'Doroudi, Alireza'
'Das, Umashankar'
'Dimmock, Jonathan R.'
_publ_section_title
;
 1,4-Dimorpholinobenzene
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o693
_journal_page_last               o695
_journal_paper_doi               10.1107/S160053680500454X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C14 H20 N2 O2'
_chemical_formula_moiety         'C14 H20 N2 O2'
_chemical_formula_sum            'C14 H20 N2 O2'
_chemical_formula_weight         248.32
_chemical_melting_point          190
_chemical_name_systematic
;
1,4-dimorpholinobenzene
;
_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                 90.994(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.9410(7)
_cell_length_b                   8.1410(9)
_cell_length_c                   11.2120(6)
_cell_measurement_reflns_used    1414
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     633.46(10)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
'SCALEPACK and DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD; rotation images; thick slices'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2081
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.94
_diffrn_standards_decay_%        <1
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.220
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1232
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0519
_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)+(0.03P)²+0.2441P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1154
_reflns_number_gt                856
_reflns_number_total             1232
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ac6160.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2205200
_cod_database_fobs_code          2205200
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 0.0501(2) 0.13777(18) 0.40000(13) 0.0409(4) Uani d . 1 O
N1 0.2945(2) 0.0122(2) 0.21801(13) 0.0300(4) Uani d . 1 N
C1 0.3381(3) -0.0949(2) 0.01610(16) 0.0310(5) Uani d . 1 C
H1 0.2265 -0.1607 0.0257 0.037 Uiso calc R 1 H
C2 0.3980(3) 0.0085(2) 0.10886(16) 0.0284(5) Uani d . 1 C
C3 0.5619(3) 0.1039(3) 0.09000(17) 0.0315(5) Uani d . 1 C
H3 0.6060 0.1764 0.1510 0.038 Uiso calc R 1 H
C4 0.0846(3) 0.0220(3) 0.20140(17) 0.0358(5) Uani d . 1 C
H4e 0.0398 -0.0695 0.1498 0.043 Uiso calc R 1 H
H4a 0.0504 0.1266 0.1612 0.043 Uiso calc R 1 H
C5 -0.0147(3) 0.0129(3) 0.32015(19) 0.0415(6) Uani d . 1 C
H5e -0.1555 0.0240 0.3071 0.050 Uiso calc R 1 H
H5a 0.0102 -0.0960 0.3566 0.050 Uiso calc R 1 H
C6 0.2515(3) 0.1180(3) 0.41985(18) 0.0441(6) Uani d . 1 C
H6a 0.2766 0.0087 0.4555 0.053 Uiso calc R 1 H
H6e 0.2978 0.2024 0.4771 0.053 Uiso calc R 1 H
C7 0.3617(3) 0.1335(3) 0.30503(17) 0.0393(6) Uani d . 1 C
H7a 0.3438 0.2453 0.2718 0.047 Uiso calc R 1 H
H7e 0.5009 0.1171 0.3217 0.047 Uiso calc R 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 0.0360(8) 0.0385(9) 0.0485(9) 0.0028(7) 0.0052(6) -0.0089(7)
N1 0.0254(9) 0.0328(10) 0.0318(9) 0.0003(7) -0.0012(6) -0.0040(7)
C1 0.0271(10) 0.0303(12) 0.0354(11) -0.0026(9) -0.0034(8) 0.0016(9)
C2 0.0289(11) 0.0260(11) 0.0302(10) 0.0024(9) -0.0035(8) 0.0017(8)
C3 0.0319(11) 0.0310(12) 0.0315(11) -0.0022(9) -0.0058(8) -0.0034(8)
C4 0.0292(11) 0.0386(12) 0.0396(12) -0.0023(10) -0.0017(8) -0.0024(10)
C5 0.0335(12) 0.0434(14) 0.0477(13) -0.0040(10) 0.0028(9) -0.0072(11)
C6 0.0369(12) 0.0536(16) 0.0419(13) -0.0020(12) 0.0011(9) -0.0127(11)
C7 0.0319(12) 0.0466(14) 0.0392(12) -0.0065(10) 0.0004(9) -0.0115(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_site_symmetry_1
_geom_angle
C6 O1 C5 . 108.50(16)
C2 N1 C7 . 115.29(16)
C2 N1 C4 . 113.87(14)
C7 N1 C4 . 110.67(15)
C3 C1 C2 3_655 121.55(18)
C3 C1 H1 3_655 119.2
C2 C1 H1 . 119.2
C1 C2 C3 . 117.08(17)
C1 C2 N1 . 120.20(17)
C3 C2 N1 . 122.72(17)
C1 C3 C2 3_655 121.37(18)
C1 C3 H3 3_655 119.3
C2 C3 H3 . 119.3
N1 C4 C5 . 110.63(16)
N1 C4 H4e . 109.5
C5 C4 H4e . 109.5
N1 C4 H4a . 109.5
C5 C4 H4a . 109.5
H4e C4 H4a . 108.1
O1 C5 C4 . 112.03(18)
O1 C5 H5e . 109.2
C4 C5 H5e . 109.2
O1 C5 H5a . 109.2
C4 C5 H5a . 109.2
H5e C5 H5a . 107.9
O1 C6 C7 . 111.56(17)
O1 C6 H6a . 109.3
C7 C6 H6a . 109.3
O1 C6 H6e . 109.3
C7 C6 H6e . 109.3
H6a C6 H6e . 108.0
N1 C7 C6 . 110.60(17)
N1 C7 H7a . 109.5
C6 C7 H7a . 109.5
N1 C7 H7e . 109.5
C6 C7 H7e . 109.5
H7a C7 H7e . 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C6 . 1.421(2)
O1 C5 . 1.423(2)
N1 C2 . 1.430(2)
N1 C7 . 1.459(2)
N1 C4 . 1.468(2)
C1 C3 3_655 1.389(3)
C1 C2 . 1.396(3)
C1 H1 . 0.9500
C2 C3 . 1.397(3)
C3 C1 3_655 1.389(3)
C3 H3 . 0.9500
C4 C5 . 1.512(3)
C4 H4e . 0.9900
C4 H4a . 0.9900
C5 H5e . 0.9900
C5 H5a . 0.9900
C6 C7 . 1.514(3)
C6 H6a . 0.9900
C6 H6e . 0.9900
C7 H7a . 0.9900
C7 H7e . 0.9900
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_4
_geom_torsion
C3 C1 C2 C3 3_655 . 0.6(3)
C3 C1 C2 N1 3_655 . -178.58(18)
C7 N1 C2 C1 . . -175.68(17)
C4 N1 C2 C1 . . -46.2(2)
C7 N1 C2 C3 . . 5.2(3)
C4 N1 C2 C3 . . 134.7(2)
C1 C2 C3 C1 . 3_655 -0.6(3)
N1 C2 C3 C1 . 3_655 178.55(18)
C2 N1 C4 C5 . . 175.86(18)
C7 N1 C4 C5 . . -52.4(2)
C6 O1 C5 C4 . . -60.1(2)
N1 C4 C5 O1 . . 56.8(2)
C5 O1 C6 C7 . . 60.6(2)
C2 N1 C7 C6 . . -175.93(17)
C4 N1 C7 C6 . . 53.0(2)
O1 C6 C7 N1 . . -58.1(2)
