#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/65/1506530.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_1506530
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          73.5(5)
_chemical_name_systematic
; 
4-[4-(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                 101.8340(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2593(2)
_cell_length_b                   16.1551(3)
_cell_length_c                   10.1261(2)
_cell_measurement_temperature    123(2)
_cell_volume                     1482.52(5)
_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 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0727
_diffrn_reflns_av_sigmaI/netI    0.0704
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16721
_diffrn_reflns_theta_full        28.11
_diffrn_reflns_theta_max         28.11
_diffrn_reflns_theta_min         3.71
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       clear_needles
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3548
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1084
_refine_ls_R_factor_gt           0.0477
_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)+(0.0586P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1182
_reflns_number_gt                2072
_reflns_number_total             3548
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0501828si20050131_011114.cif
_cod_data_source_block           5baa
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '73-74' was changed to '73.5(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               1506530
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 0.80672(11) 0.03423(5) 0.93282(10) 0.0279(3) Uani 1 1 d .
N1 N 0.83020(12) -0.56126(7) 0.97242(11) 0.0226(3) Uani 1 1 d .
O4" O 0.87774(11) -0.72665(6) 1.07213(11) 0.0338(3) Uani 1 1 d .
C1 C 0.77155(15) -0.49160(8) 0.89651(14) 0.0200(3) Uani 1 1 d .
C7 C 0.60783(18) -0.26848(8) 0.67264(15) 0.0322(4) Uani 1 1 d .
H7A H 0.6415 -0.2688 0.5859 0.039 Uiso 1 1 calc R
H7B H 0.4986 -0.2699 0.6514 0.039 Uiso 1 1 calc R
C1' C 0.65672(16) -0.18846(8) 0.74479(14) 0.0234(3) Uani 1 1 d .
C6 C 0.67827(15) -0.43600(8) 0.94445(14) 0.0228(3) Uani 1 1 d .
H6 H 0.6498 -0.4468 1.0278 0.027 Uiso 1 1 calc R
C3 C 0.75402(17) -0.40139(8) 0.70203(14) 0.0280(4) Uani 1 1 d .
H3 H 0.7814 -0.3903 0.6184 0.034 Uiso 1 1 calc R
C5 C 0.62711(15) -0.36578(8) 0.87236(14) 0.0241(4) Uani 1 1 d .
H5 H 0.5645 -0.3292 0.9081 0.029 Uiso 1 1 calc R
C4 C 0.66339(16) -0.34630(8) 0.74969(14) 0.0242(3) Uani 1 1 d .
C4' C 0.74985(15) -0.03735(8) 0.87058(13) 0.0208(3) Uani 1 1 d .
C2 C 0.80661(16) -0.47261(9) 0.77237(14) 0.0260(4) Uani 1 1 d .
H2 H 0.8679 -0.5093 0.7352 0.031 Uiso 1 1 calc R
C2" C 0.90046(16) -0.62339(9) 0.90266(15) 0.0278(4) Uani 1 1 d .
H2"1 H 0.9751 -0.5963 0.8598 0.033 Uiso 1 1 calc R
H2"2 H 0.8254 -0.6489 0.8304 0.033 Uiso 1 1 calc R
C3" C 0.97338(16) -0.68955(9) 0.99706(16) 0.0310(4) Uani 1 1 d .
H3"1 H 1.0117 -0.7329 0.9442 0.037 Uiso 1 1 calc R
H3"2 H 1.0586 -0.6652 1.0603 0.037 Uiso 1 1 calc R
C3' C 0.85141(15) -0.09727(8) 0.85326(14) 0.0233(3) Uani 1 1 d .
H3' H 0.9538 -0.0874 0.8847 0.028 Uiso 1 1 calc R
C5' C 0.60221(15) -0.05279(9) 0.82672(14) 0.0243(4) Uani 1 1 d .
H5' H 0.5310 -0.0124 0.8376 0.029 Uiso 1 1 calc R
C6' C 0.55823(16) -0.12845(8) 0.76599(14) 0.0258(4) Uani 1 1 d .
H6' H 0.4557 -0.1392 0.7379 0.031 Uiso 1 1 calc R
C6" C 0.74247(16) -0.59800(9) 1.06121(14) 0.0286(4) Uani 1 1 d .
H6"1 H 0.6516 -0.6221 1.0060 0.034 Uiso 1 1 calc R
H6"2 H 0.7128 -0.5542 1.1187 0.034 Uiso 1 1 calc R
C5" C 0.82555(18) -0.66411(9) 1.14942(15) 0.0327(4) Uani 1 1 d .
H5"1 H 0.9104 -0.6389 1.2120 0.039 Uiso 1 1 calc R
H5"2 H 0.7601 -0.6895 1.2042 0.039 Uiso 1 1 calc R
C7' C 0.70485(17) 0.09518(9) 0.95640(17) 0.0354(4) Uani 1 1 d .
H7'1 H 0.6413 0.1112 0.8705 0.053 Uiso 1 1 calc R
H7'2 H 0.7587 0.1438 0.9985 0.053 Uiso 1 1 calc R
H7'3 H 0.6441 0.0727 1.0166 0.053 Uiso 1 1 calc R
C2' C 0.80482(16) -0.17111(8) 0.79081(13) 0.0243(4) Uani 1 1 d .
H2' H 0.8762 -0.2112 0.7790 0.029 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' 117.25(11)
C1 N1 C2" 116.56(11)
C1 N1 C6" 117.48(11)
C2" N1 C6" 112.35(11)
C3" O4" C5" 108.41(11)
C2 C1 C6 116.45(13)
C2 C1 N1 122.19(13)
C6 C1 N1 121.33(13)
C1' C7 C4 115.21(11)
C6' C1' C2' 116.55(13)
C6' C1' C7 122.42(13)
C2' C1' C7 121.01(14)
C5 C6 C1 120.89(13)
C4 C3 C2 122.07(14)
C6 C5 C4 122.70(13)
C3 C4 C5 116.36(13)
C3 C4 C7 121.58(14)
C5 C4 C7 122.06(13)
O1' C4' C5' 124.50(13)
O1' C4' C3' 116.18(12)
C5' C4' C3' 119.31(13)
C3 C2 C1 121.51(14)
N1 C2" C3" 111.71(12)
O4" C3" C2" 113.29(12)
C2' C3' C4' 120.42(13)
C4' C5' C6' 119.02(13)
C1' C6' C5' 122.96(14)
N1 C6" C5" 112.03(12)
O4" C5" C6" 111.65(12)
C3' C2' C1' 121.70(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1' C4' 1.3696(16)
O1' C7' 1.4173(17)
N1 C1 1.4076(17)
N1 C2" 1.4553(17)
N1 C6" 1.4560(17)
O4" C3" 1.4134(17)
O4" C5" 1.4220(17)
C1 C2 1.395(2)
C1 C6 1.4002(19)
C7 C1' 1.5080(19)
C7 C4 1.5130(19)
C1' C6' 1.378(2)
C1' C2' 1.3835(19)
C6 C5 1.3793(19)
C3 C4 1.377(2)
C3 C2 1.3878(19)
C5 C4 1.388(2)
C4' C5' 1.3708(19)
C4' C3' 1.3855(19)
C2" C3" 1.499(2)
C3' C2' 1.3775(19)
C5' C6' 1.3913(19)
C6" C5" 1.4994(19)
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" N1 C1 C2 -14.26(19)
C6" N1 C1 C2 -151.92(13)
C2" N1 C1 C6 167.92(12)
C6" N1 C1 C6 30.26(18)
C4 C7 C1' C6' -125.36(15)
C4 C7 C1' C2' 56.0(2)
C2 C1 C6 C5 -1.1(2)
N1 C1 C6 C5 176.82(12)
C1 C6 C5 C4 0.4(2)
C2 C3 C4 C5 0.0(2)
C2 C3 C4 C7 179.46(13)
C6 C5 C4 C3 0.2(2)
C6 C5 C4 C7 -179.25(12)
C1' C7 C4 C3 -117.59(16)
C1' C7 C4 C5 61.9(2)
C7' O1' C4' C5' 1.86(19)
C7' O1' C4' C3' -177.62(13)
C4 C3 C2 C1 -0.8(2)
C6 C1 C2 C3 1.3(2)
N1 C1 C2 C3 -176.59(12)
C1 N1 C2" C3" 173.57(11)
C6" N1 C2" C3" -46.68(16)
C5" O4" C3" C2" -59.67(15)
N1 C2" C3" O4" 53.58(16)
O1' C4' C3' C2' -179.52(12)
C5' C4' C3' C2' 1.0(2)
O1' C4' C5' C6' -179.37(12)
C3' C4' C5' C6' 0.1(2)
C2' C1' C6' C5' 1.8(2)
C7 C1' C6' C5' -176.88(13)
C4' C5' C6' C1' -1.5(2)
C1 N1 C6" C5" -172.35(11)
C2" N1 C6" C5" 48.29(16)
C3" O4" C5" C6" 60.26(15)
N1 C6" C5" O4" -55.80(16)
C4' C3' C2' C1' -0.7(2)
C6' C1' C2' C3' -0.7(2)
C7 C1' C2' C3' 178.01(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9464067
