#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/65/1506529.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1506529
loop_
_publ_author_name
'Rosamilia, Anthony E.'
'Scott, Janet L.'
'Strauss, Christopher R.'
_publ_section_title
;
 Preparation of 2- and 4-arylmethyl N-substituted and N,N-disubstituted
 anilines via a "green", multicomponent reaction.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1525
_journal_page_last               1528
_journal_paper_doi               10.1021/ol0501828
_journal_volume                  7
_journal_year                    2005
_chemical_formula_moiety         'C18 H21 N O2'
_chemical_formula_sum            'C18 H21 N O2'
_chemical_formula_weight         283.36
_chemical_melting_point          64.5(5)
_chemical_name_systematic
; 
4-[2-(4-methoxybenzyl)phenyl]morpholine 
;
_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                 91.069(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8454(2)
_cell_length_b                   7.4615(3)
_cell_length_c                   27.2798(12)
_cell_measurement_temperature    123(2)
_cell_volume                     1393.13(9)
_computing_cell_refinement       'Nonius collect'
_computing_data_collection       'Nonius collect'
_computing_data_reduction        'Nonius collect'
_computing_molecular_graphics    X-Seed
_computing_publication_material  ciftab
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.848
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measurement_device_type  'Enraf Nonius Kappa CCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0603
_diffrn_reflns_av_sigmaI/netI    0.1093
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            6082
_diffrn_reflns_theta_full        30.28
_diffrn_reflns_theta_max         30.28
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       clear_plates
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.1373
_refine_ls_R_factor_gt           0.0503
_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)+(0.0544P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1238
_reflns_number_gt                1804
_reflns_number_total             3536
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0501828si20050131_011114.cif
_cod_data_source_block           4baa
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '64-65' was changed to '64.5(5)' -
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1506529
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1' O 0.45390(17) 0.97289(18) 0.31852(4) 0.0253(3) Uani 1 1 d .
N1 N 0.2680(2) 0.9375(2) 0.07868(5) 0.0205(4) Uani 1 1 d .
O4" O 0.56549(18) 0.74002(19) 0.03415(4) 0.0282(4) Uani 1 1 d .
C7 C 0.0012(2) 0.9115(3) 0.15425(6) 0.0220(4) Uani 1 1 d .
H7A H -0.1345 0.8897 0.1647 0.026 Uiso 1 1 calc R
H7B H 0.0434 0.8066 0.1349 0.026 Uiso 1 1 calc R
C3 C -0.1202(3) 1.2169(3) 0.13024(6) 0.0235(5) Uani 1 1 d .
H3 H -0.2080 1.2101 0.1567 0.028 Uiso 1 1 calc R
C5' C 0.1703(3) 1.0310(3) 0.27532(6) 0.0225(4) Uani 1 1 d .
H5' H 0.1233 1.0933 0.3031 0.027 Uiso 1 1 calc R
C1' C 0.1265(3) 0.9295(3) 0.19703(6) 0.0203(4) Uani 1 1 d .
C1 C 0.1343(2) 1.0841(3) 0.08624(6) 0.0195(4) Uani 1 1 d .
C2' C 0.3129(3) 0.8574(3) 0.19982(6) 0.0249(5) Uani 1 1 d .
H2' H 0.3606 0.7959 0.1720 0.030 Uiso 1 1 calc R
C4' C 0.3547(3) 0.9556(3) 0.27749(6) 0.0206(4) Uani 1 1 d .
C6 C 0.1291(3) 1.2330(3) 0.05765(6) 0.0235(5) Uani 1 1 d .
H6 H 0.2178 1.2420 0.0314 0.028 Uiso 1 1 calc R
C3' C 0.4285(3) 0.8698(3) 0.23940(6) 0.0241(4) Uani 1 1 d .
H3' H 0.5563 0.8203 0.2404 0.029 Uiso 1 1 calc R
C2 C 0.0061(2) 1.0743(3) 0.12301(6) 0.0191(4) Uani 1 1 d .
C5 C -0.0004(3) 1.3721(3) 0.06525(6) 0.0244(5) Uani 1 1 d .
H5 H 0.0003 1.4735 0.0442 0.029 Uiso 1 1 calc R
C6' C 0.0579(3) 1.0188(3) 0.23576(6) 0.0232(4) Uani 1 1 d .
H6' H -0.0683 1.0718 0.2347 0.028 Uiso 1 1 calc R
C7' C 0.6402(3) 0.8861(3) 0.32317(7) 0.0329(5) Uani 1 1 d .
H7'1 H 0.6256 0.7584 0.3156 0.049 Uiso 1 1 calc R
H7'2 H 0.6907 0.8999 0.3568 0.049 Uiso 1 1 calc R
H7'3 H 0.7316 0.9407 0.3003 0.049 Uiso 1 1 calc R
C4 C -0.1254(3) 1.3648(3) 0.10176(6) 0.0255(5) Uani 1 1 d .
H4 H -0.2148 1.4595 0.1076 0.031 Uiso 1 1 calc R
C2" C 0.4738(3) 0.9933(3) 0.08138(7) 0.0286(5) Uani 1 1 d .
H2"1 H 0.5015 1.0530 0.1132 0.034 Uiso 1 1 calc R
H2"2 H 0.5007 1.0797 0.0548 0.034 Uiso 1 1 calc R
C3" C 0.6032(3) 0.8304(3) 0.07631(7) 0.0310(5) Uani 1 1 d .
H3"1 H 0.7417 0.8687 0.0771 0.037 Uiso 1 1 calc R
H3"2 H 0.5830 0.7494 0.1045 0.037 Uiso 1 1 calc R
C6" C 0.2305(3) 0.8445(3) 0.03526(7) 0.0284(5) Uani 1 1 d .
H6"1 H 0.2498 0.9251 0.0069 0.034 Uiso 1 1 calc R
H6"2 H 0.0931 0.8030 0.0344 0.034 Uiso 1 1 calc R
C5" C 0.3664(3) 0.6850(3) 0.03174(7) 0.0314(5) Uani 1 1 d .
H5"1 H 0.3405 0.6008 0.0589 0.038 Uiso 1 1 calc R
H5"2 H 0.3407 0.6213 0.0004 0.038 Uiso 1 1 calc R
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
C4' O1' C7' 118.62(14)
C6" N1 C1 113.05(14)
C6" N1 C2" 110.19(13)
C1 N1 C2" 112.81(15)
C3" O4" C5" 110.49(13)
C1' C7 C2 111.63(16)
C4 C3 C2 123.73(16)
C6' C5' C4' 121.72(17)
C6' C1' C2' 119.03(17)
C6' C1' C7 118.17(17)
C2' C1' C7 122.80(16)
C2 C1 C6 117.52(18)
C2 C1 N1 119.26(17)
C6 C1 N1 123.22(15)
C3' C2' C1' 123.44(17)
O1' C4' C3' 121.30(17)
O1' C4' C5' 117.17(15)
C3' C4' C5' 121.53(17)
C1 C6 C5 122.54(17)
C4' C3' C2' 116.07(18)
C1 C2 C3 118.71(17)
C1 C2 C7 119.60(17)
C3 C2 C7 121.68(15)
C4 C5 C6 120.41(19)
C5' C6' C1' 118.19(18)
C5 C4 C3 117.07(19)
N1 C2" C3" 109.29(16)
O4" C3" C2" 112.06(16)
N1 C6" C5" 109.97(16)
O4" C5" C6" 111.04(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1' C4' 1.305(2)
O1' C7' 1.434(2)
N1 C6" 1.392(2)
N1 C1 1.444(2)
N1 C2" 1.470(2)
O4" C3" 1.354(2)
O4" C5" 1.424(2)
C7 C1' 1.442(2)
C7 C2 1.485(3)
C3 C4 1.350(3)
C3 C2 1.387(3)
C5' C6' 1.317(2)
C5' C4' 1.383(2)
C1' C6' 1.341(2)
C1' C2' 1.385(2)
C1 C2 1.347(2)
C1 C6 1.357(3)
C2' C3' 1.330(2)
C4' C3' 1.328(2)
C6 C5 1.383(3)
C5 C4 1.326(2)
C2" C3" 1.512(3)
C6" C5" 1.515(3)
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
C2 C7 C1' C6' 81.8(2)
C2 C7 C1' C2' -98.7(2)
C6" N1 C1 C2 112.17(19)
C2" N1 C1 C2 -121.95(18)
C6" N1 C1 C6 -67.2(2)
C2" N1 C1 C6 58.7(2)
C6' C1' C2' C3' 0.9(3)
C7 C1' C2' C3' -178.57(19)
C7' O1' C4' C3' -4.4(3)
C7' O1' C4' C5' 175.87(16)
C6' C5' C4' O1' -179.12(18)
C6' C5' C4' C3' 1.2(3)
C2 C1 C6 C5 0.4(3)
N1 C1 C6 C5 179.77(16)
O1' C4' C3' C2' 178.72(18)
C5' C4' C3' C2' -1.6(3)
C1' C2' C3' C4' 0.6(3)
C6 C1 C2 C3 -1.3(3)
N1 C1 C2 C3 179.31(15)
C6 C1 C2 C7 177.87(17)
N1 C1 C2 C7 -1.5(2)
C4 C3 C2 C1 1.5(3)
C4 C3 C2 C7 -177.69(18)
C1' C7 C2 C1 92.1(2)
C1' C7 C2 C3 -88.8(2)
C1 C6 C5 C4 0.5(3)
C4' C5' C6' C1' 0.4(3)
C2' C1' C6' C5' -1.3(3)
C7 C1' C6' C5' 178.16(17)
C6 C5 C4 C3 -0.4(3)
C2 C3 C4 C5 -0.6(3)
C6" N1 C2" C3" -56.2(2)
C1 N1 C2" C3" 176.44(14)
C5" O4" C3" C2" -58.2(2)
N1 C2" C3" O4" 57.1(2)
C1 N1 C6" C5" -175.79(15)
C2" N1 C6" C5" 56.9(2)
C3" O4" C5" C6" 58.0(2)
N1 C6" C5" O4" -57.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9452559
