#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/04/2220427.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_2220427
loop_
_publ_author_name
'Bian, Yan-Jiang'
_publ_section_title
;
 N-Benzyl-N-methylmorpholinium chloride
;
_journal_coeditor_code           BT2824
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o38
_journal_paper_doi               10.1107/S1600536808040506
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H18 N O +, Cl -'
_chemical_formula_moiety         'C12 H18 N O +, Cl -'
_chemical_formula_sum            'C12 H18 Cl N O'
_chemical_formula_weight         227.72
_chemical_name_systematic
;
N-Benzyl-N-methylmorpholinium chloride
;
_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'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.8693(8)
_cell_length_b                   9.5732(8)
_cell_length_c                   24.989(2)
_cell_measurement_reflns_used    5341
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.6
_cell_volume                     2361.0(3)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            23984
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         1.63
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  0.9539
_exptl_absorpt_correction_T_min  0.9373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.367
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0504P)²+0.8783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1029
_reflns_number_gt                2658
_reflns_number_total             2806
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2824.cif
_cod_data_source_block           I
_cod_original_cell_volume        2361.0(4)
_cod_database_code               2220427
_cod_database_fobs_code          2220427
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -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
Cl Cl1 0.06425(3) 0.24262(3) 0.579326(12) 0.01816(12) Uani d . 1 . .
O O1 0.67612(10) 0.15043(10) 0.57658(4) 0.0243(2) Uani d . 1 . .
N N1 0.44588(10) 0.33344(11) 0.59493(4) 0.0150(2) Uani d . 1 . .
C C1 0.59109(13) 0.37790(14) 0.60368(5) 0.0188(3) Uani d . 1 . .
H H1A 0.6158 0.3622 0.6416 0.023 Uiso calc R 1 . .
H H1B 0.5997 0.4791 0.5962 0.023 Uiso calc R 1 . .
C C2 0.68808(14) 0.29772(15) 0.56803(6) 0.0215(3) Uani d . 1 . .
H H2A 0.6683 0.3193 0.5301 0.026 Uiso calc R 1 . .
H H2B 0.7822 0.3275 0.5757 0.026 Uiso calc R 1 . .
C C3 0.54189(14) 0.10657(14) 0.56303(6) 0.0224(3) Uani d . 1 . .
H H3A 0.5349 0.0039 0.5668 0.027 Uiso calc R 1 . .
H H3B 0.5228 0.1307 0.5252 0.027 Uiso calc R 1 . .
C C4 0.43833(13) 0.17620(14) 0.59888(5) 0.0178(3) Uani d . 1 . .
H H4A 0.3464 0.1448 0.5886 0.021 Uiso calc R 1 . .
H H4B 0.4543 0.1475 0.6364 0.021 Uiso calc R 1 . .
C C5 0.35303(13) 0.40397(14) 0.63597(5) 0.0183(3) Uani d . 1 . .
H H5A 0.3710 0.5057 0.6352 0.022 Uiso calc R 1 . .
H H5B 0.2580 0.3899 0.6245 0.022 Uiso calc R 1 . .
C C6 0.36606(13) 0.35467(14) 0.69294(5) 0.0181(3) Uani d . 1 . .
C C7 0.28094(14) 0.24900(14) 0.71151(6) 0.0210(3) Uani d . 1 . .
H H7 0.2193 0.2053 0.6876 0.025 Uiso calc R 1 . .
C C8 0.28540(15) 0.20693(17) 0.76477(6) 0.0278(3) Uani d . 1 . .
H H8 0.2272 0.1346 0.7770 0.033 Uiso calc R 1 . .
C C9 0.37464(16) 0.27038(17) 0.79996(6) 0.0295(3) Uani d . 1 . .
H H9 0.3784 0.2411 0.8363 0.035 Uiso calc R 1 . .
C C10 0.45814(16) 0.37636(18) 0.78209(6) 0.0301(4) Uani d . 1 . .
H H10 0.5188 0.4203 0.8063 0.036 Uiso calc R 1 . .
C C11 0.45410(14) 0.41926(16) 0.72890(6) 0.0240(3) Uani d . 1 . .
H H11 0.5115 0.4927 0.7171 0.029 Uiso calc R 1 . .
C C12 0.39548(14) 0.38154(14) 0.54104(5) 0.0193(3) Uani d . 1 . .
H H12A 0.3981 0.4838 0.5394 0.029 Uiso calc R 1 . .
H H12B 0.3021 0.3494 0.5358 0.029 Uiso calc R 1 . .
H H12C 0.4534 0.3427 0.5129 0.029 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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
C3 O1 C2 . . 109.28(10) ?
C12 N1 C4 . . 110.28(10) ?
C12 N1 C1 . . 110.87(10) ?
C4 N1 C1 . . 108.54(10) ?
C12 N1 C5 . . 105.42(9) ?
C4 N1 C5 . . 111.47(9) ?
C1 N1 C5 . . 110.26(10) ?
N1 C1 C2 . . 111.78(11) ?
N1 C1 H1A . . 109.3 ?
C2 C1 H1A . . 109.3 ?
N1 C1 H1B . . 109.3 ?
C2 C1 H1B . . 109.3 ?
H1A C1 H1B . . 107.9 ?
O1 C2 C1 . . 111.04(11) ?
O1 C2 H2A . . 109.4 ?
C1 C2 H2A . . 109.4 ?
O1 C2 H2B . . 109.4 ?
C1 C2 H2B . . 109.4 ?
H2A C2 H2B . . 108.0 ?
O1 C3 C4 . . 110.85(11) ?
O1 C3 H3A . . 109.5 ?
C4 C3 H3A . . 109.5 ?
O1 C3 H3B . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
N1 C4 C3 . . 111.52(10) ?
N1 C4 H4A . . 109.3 ?
C3 C4 H4A . . 109.3 ?
N1 C4 H4B . . 109.3 ?
C3 C4 H4B . . 109.3 ?
H4A C4 H4B . . 108.0 ?
C6 C5 N1 . . 116.35(10) ?
C6 C5 H5A . . 108.2 ?
N1 C5 H5A . . 108.2 ?
C6 C5 H5B . . 108.2 ?
N1 C5 H5B . . 108.2 ?
H5A C5 H5B . . 107.4 ?
C7 C6 C11 . . 118.87(12) ?
C7 C6 C5 . . 119.38(12) ?
C11 C6 C5 . . 121.57(12) ?
C8 C7 C6 . . 120.61(13) ?
C8 C7 H7 . . 119.7 ?
C6 C7 H7 . . 119.7 ?
C9 C8 C7 . . 120.04(14) ?
C9 C8 H8 . . 120.0 ?
C7 C8 H8 . . 120.0 ?
C10 C9 C8 . . 119.76(14) ?
C10 C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
C9 C10 C11 . . 120.56(14) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
C10 C11 C6 . . 120.15(14) ?
C10 C11 H11 . . 119.9 ?
C6 C11 H11 . . 119.9 ?
N1 C12 H12A . . 109.5 ?
N1 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N1 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
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
O1 C3 . 1.4304(17) ?
O1 C2 . 1.4310(17) ?
N1 C12 . 1.5075(16) ?
N1 C4 . 1.5104(18) ?
N1 C1 . 1.5109(16) ?
N1 C5 . 1.5321(16) ?
C1 C2 . 1.5164(19) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C4 . 1.5138(18) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.5056(17) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C7 . 1.3943(19) ?
C6 C11 . 1.3946(19) ?
C7 C8 . 1.3914(19) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.385(2) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.381(2) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.392(2) ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
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
C3 H3A Cl1 2_545 0.99 2.70 3.6610(14) 162.7
C5 H5A Cl1 2 0.99 2.74 3.6304(14) 150.1
C5 H5B Cl1 . 0.99 2.63 3.5373(14) 152.4
C9 H9 Cl1 8_657 0.95 2.80 3.5599(16) 138.1
C12 H12A Cl1 2 0.98 2.70 3.6085(14) 155.0
C12 H12B Cl1 . 0.98 2.78 3.6566(14) 148.9
C12 H12C Cl1 6_666 0.98 2.68 3.6380(14) 166.4
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
C12 N1 C1 C2 . . . . -70.18(14) ?
C4 N1 C1 C2 . . . . 51.09(13) ?
C5 N1 C1 C2 . . . . 173.45(10) ?
C3 O1 C2 C1 . . . . 61.86(14) ?
N1 C1 C2 O1 . . . . -57.37(14) ?
C2 O1 C3 C4 . . . . -62.50(14) ?
C12 N1 C4 C3 . . . . 70.00(13) ?
C1 N1 C4 C3 . . . . -51.64(13) ?
C5 N1 C4 C3 . . . . -173.26(11) ?
O1 C3 C4 N1 . . . . 58.57(14) ?
C12 N1 C5 C6 . . . . 169.98(11) ?
C4 N1 C5 C6 . . . . 50.32(14) ?
C1 N1 C5 C6 . . . . -70.30(14) ?
N1 C5 C6 C7 . . . . -93.35(14) ?
N1 C5 C6 C11 . . . . 91.63(15) ?
C11 C6 C7 C8 . . . . -1.1(2) ?
C5 C6 C7 C8 . . . . -176.30(12) ?
C6 C7 C8 C9 . . . . 0.2(2) ?
C7 C8 C9 C10 . . . . 0.6(2) ?
C8 C9 C10 C11 . . . . -0.5(2) ?
C9 C10 C11 C6 . . . . -0.5(2) ?
C7 C6 C11 C10 . . . . 1.3(2) ?
C5 C6 C11 C10 . . . . 176.32(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 15012527
