#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/53/2215339.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_2215339
loop_
_publ_author_name
'Yang, Shu-Ping'
'Han, Li-Jun'
'Wang, Da-Qi'
'Zhao, Cui'
_publ_section_title
;
 4-Methoxy-N-(3,4-methylenedioxybenzyl)aniline
;
_journal_coeditor_code           AT2401
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4100
_journal_page_last               o4100
_journal_paper_doi               10.1107/S1600536807045527
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H15 N O3'
_chemical_formula_moiety         'C15 H15 N O3'
_chemical_formula_sum            'C15 H15 N O3'
_chemical_formula_weight         257.28
_chemical_melting_point          339
_chemical_name_systematic
;
4-Methoxy-N-(3,4-methylenedioxybenzyl)aniline
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   54.050(3)
_cell_length_b                   7.3530(10)
_cell_length_c                   6.4830(9)
_cell_measurement_reflns_used    2390
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.655
_cell_measurement_theta_min      2.791
_cell_volume                     2576.5(5)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0605
_diffrn_reflns_av_sigmaI/netI    0.0600
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -64
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            9965
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.51
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9594
_exptl_absorpt_correction_T_min  0.9533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.286
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1264
_refine_ls_R_factor_gt           0.0938
_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)+(0.044P)²+7.8609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1985
_refine_ls_wR_factor_ref         0.2144
_reflns_number_gt                1478
_reflns_number_total             2201
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2401.cif
_cod_data_source_block           I
_cod_database_code               2215339
_cod_database_fobs_code          2215339
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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
N N1 0.37308(6) 0.2577(5) 0.7958(6) 0.0443(10) Uani d . 1
H H1A 0.3836 0.2220 0.8954 0.053 Uiso calc PR 0.50
H H1B 0.3765 0.3751 0.7687 0.053 Uiso calc PR 0.50
O O1 0.47087(6) 0.1691(6) 0.6437(6) 0.0680(12) Uani d . 1
O O2 0.47446(6) 0.3279(5) 0.3376(6) 0.0621(11) Uani d . 1
O O3 0.27794(6) 0.2373(5) 1.1237(6) 0.0570(10) Uani d . 1
C C1 0.37902(8) 0.1547(6) 0.6126(7) 0.0457(12) Uani d . 1
H H1C 0.3668 0.1788 0.5067 0.055 Uiso calc R 1
H H1D 0.3786 0.0257 0.6440 0.055 Uiso calc R 1
C C2 0.40408(8) 0.2046(6) 0.5346(7) 0.0366(10) Uani d . 1
C C3 0.42537(8) 0.1544(6) 0.6460(7) 0.0436(11) Uani d . 1
H H3 0.4242 0.0916 0.7701 0.052 Uiso calc R 1
C C4 0.44761(8) 0.2016(6) 0.5649(7) 0.0396(11) Uani d . 1
C C5 0.45004(8) 0.2954(6) 0.3819(7) 0.0419(11) Uani d . 1
C C6 0.42980(9) 0.3458(7) 0.2706(8) 0.0507(13) Uani d . 1
H H6 0.4312 0.4090 0.1469 0.061 Uiso calc R 1
C C7 0.40707(8) 0.2980(6) 0.3510(8) 0.0456(12) Uani d . 1
H H7 0.3930 0.3305 0.2776 0.055 Uiso calc R 1
C C8 0.48742(10) 0.2496(9) 0.5030(10) 0.0771(19) Uani d . 1
H H8A 0.4970 0.3425 0.5727 0.093 Uiso calc R 1
H H8B 0.4988 0.1582 0.4512 0.093 Uiso calc R 1
C C9 0.34927(7) 0.2513(6) 0.8788(7) 0.0344(10) Uani d . 1
C C10 0.34322(8) 0.3562(6) 1.0500(7) 0.0383(11) Uani d . 1
H H10 0.3553 0.4287 1.1099 0.046 Uiso calc R 1
C C11 0.31982(8) 0.3557(6) 1.1336(7) 0.0421(11) Uani d . 1
H H11 0.3163 0.4286 1.2472 0.051 Uiso calc R 1
C C12 0.30174(8) 0.2492(6) 1.0509(7) 0.0396(11) Uani d . 1
C C13 0.30695(8) 0.1451(6) 0.8808(7) 0.0429(11) Uani d . 1
H H13 0.2945 0.0744 0.8220 0.051 Uiso calc R 1
C C14 0.33044(8) 0.1440(6) 0.7956(7) 0.0402(11) Uani d . 1
H H14 0.3337 0.0711 0.6816 0.048 Uiso calc R 1
C C15 0.27188(10) 0.3404(9) 1.3020(9) 0.0772(19) Uani d . 1
H H15A 0.2819 0.3011 1.4157 0.116 Uiso calc R 1
H H15B 0.2547 0.3230 1.3352 0.116 Uiso calc R 1
H H15C 0.2749 0.4670 1.2755 0.116 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'
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
C9 N1 C1 . . 120.3(4)
C9 N1 H1A . . 107.3
C1 N1 H1A . . 107.3
C9 N1 H1B . . 107.3
C1 N1 H1B . . 107.3
H1A N1 H1B . . 106.9
C4 O1 C8 . . 105.5(4)
C5 O2 C8 . . 104.4(4)
C12 O3 C15 . . 117.5(4)
N1 C1 C2 . . 110.6(4)
N1 C1 H1C . . 109.5
C2 C1 H1C . . 109.5
N1 C1 H1D . . 109.5
C2 C1 H1D . . 109.5
H1C C1 H1D . . 108.1
C7 C2 C3 . . 118.4(4)
C7 C2 C1 . . 121.3(4)
C3 C2 C1 . . 120.2(4)
C4 C3 C2 . . 117.3(4)
C4 C3 H3 . . 121.4
C2 C3 H3 . . 121.4
C3 C4 O1 . . 128.4(4)
C3 C4 C5 . . 123.1(4)
O1 C4 C5 . . 108.6(4)
C6 C5 O2 . . 127.9(4)
C6 C5 C4 . . 121.0(4)
O2 C5 C4 . . 111.1(4)
C5 C6 C7 . . 116.5(4)
C5 C6 H6 . . 121.8
C7 C6 H6 . . 121.8
C6 C7 C2 . . 123.7(4)
C6 C7 H7 . . 118.1
C2 C7 H7 . . 118.1
O2 C8 O1 . . 110.5(4)
O2 C8 O2 . 4_655 73.1(3)
O1 C8 O2 . 4_655 165.9(5)
O2 C8 O1 . 4_656 162.5(4)
O1 C8 O1 . 4_656 84.7(3)
O2 C8 O1 4_655 4_656 94.30(17)
O2 C8 H8A . . 109.6
O1 C8 H8A . . 109.6
O2 C8 H8A 4_655 . 81.0
O1 C8 H8A 4_656 . 55.3
O2 C8 H8B . . 109.6
O1 C8 H8B . . 109.6
O2 C8 H8B 4_655 . 57.1
O1 C8 H8B 4_656 . 71.4
H8A C8 H8B . . 108.1
C10 C9 N1 . . 120.4(4)
C10 C9 C14 . . 116.8(4)
N1 C9 C14 . . 122.8(4)
C11 C10 C9 . . 122.0(4)
C11 C10 H10 . . 119.0
C9 C10 H10 . . 119.0
C12 C11 C10 . . 120.4(4)
C12 C11 H11 . . 119.8
C10 C11 H11 . . 119.8
C11 C12 C13 . . 119.4(4)
C11 C12 O3 . . 125.0(4)
C13 C12 O3 . . 115.7(4)
C12 C13 C14 . . 120.8(4)
C12 C13 H13 . . 119.6
C14 C13 H13 . . 119.6
C13 C14 C9 . . 120.7(4)
C13 C14 H14 . . 119.6
C9 C14 H14 . . 119.6
O3 C15 H15A . . 109.5
O3 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
O3 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C9 . 1.396(5)
N1 C1 . 1.445(6)
N1 H1A . 0.9000
N1 H1B . 0.9000
O1 C4 . 1.378(5)
O1 C8 . 1.408(6)
O2 C5 . 1.371(5)
O2 C8 . 1.405(6)
O3 C12 . 1.373(5)
O3 C15 . 1.420(6)
C1 C2 . 1.491(6)
C1 H1C . 0.9700
C1 H1D . 0.9700
C2 C7 . 1.384(6)
C2 C3 . 1.408(6)
C3 C4 . 1.357(6)
C3 H3 . 0.9300
C4 C5 . 1.379(6)
C5 C6 . 1.362(6)
C6 C7 . 1.380(6)
C6 H6 . 0.9300
C7 H7 . 0.9300
C8 O2 4_655 3.074(7)
C8 O1 4_656 3.267(7)
C8 H8A . 0.9700
C8 H8B . 0.9700
C9 C10 . 1.391(6)
C9 C14 . 1.396(6)
C10 C11 . 1.376(6)
C10 H10 . 0.9300
C11 C12 . 1.362(6)
C11 H11 . 0.9300
C12 C13 . 1.371(6)
C13 C14 . 1.385(6)
C13 H13 . 0.9300
C14 H14 . 0.9300
C15 H15A . 0.9600
C15 H15B . 0.9600
C15 H15C . 0.9600
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
_geom_hbond_publ_flag
C15 H15B O3 2 0.96 2.61 3.454(6) 146.8 n
C3 H3 Cg1 8_556 0.93 2.82 3.64(2) 148.2 y
C6 H6 Cg1 8_565 0.93 2.75 3.55(2) 144.8 y
C11 H11 Cg2 8_566 0.93 2.80 3.63(2) 149.5 y
C14 H14 Cg2 8 0.93 2.76 3.59(2) 149.0 y
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_4
_geom_torsion
C9 N1 C1 C2 . 171.2(4)
N1 C1 C2 C7 . -111.3(5)
N1 C1 C2 C3 . 69.7(5)
C7 C2 C3 C4 . 0.0(6)
C1 C2 C3 C4 . 179.0(4)
C2 C3 C4 O1 . 179.8(5)
C2 C3 C4 C5 . 0.3(7)
C8 O1 C4 C3 . -178.6(5)
C8 O1 C4 C5 . 0.9(6)
C8 O2 C5 C6 . 179.2(5)
C8 O2 C5 C4 . -0.1(6)
C3 C4 C5 C6 . -0.4(7)
O1 C4 C5 C6 . -179.9(5)
C3 C4 C5 O2 . 179.0(4)
O1 C4 C5 O2 . -0.5(5)
O2 C5 C6 C7 . -179.2(5)
C4 C5 C6 C7 . 0.1(7)
C5 C6 C7 C2 . 0.2(7)
C3 C2 C7 C6 . -0.2(7)
C1 C2 C7 C6 . -179.3(4)
C5 O2 C8 O1 . 0.7(7)
C5 O2 C8 O2 4_655 166.3(3)
C5 O2 C8 O1 4_656 -148.4(13)
C4 O1 C8 O2 . -1.0(7)
C4 O1 C8 O2 4_655 -103.3(15)
C4 O1 C8 O1 4_656 170.0(3)
C1 N1 C9 C10 . -177.3(4)
C1 N1 C9 C14 . 1.8(7)
N1 C9 C10 C11 . 178.8(4)
C14 C9 C10 C11 . -0.4(7)
C9 C10 C11 C12 . 0.8(7)
C10 C11 C12 C13 . -1.3(7)
C10 C11 C12 O3 . 179.2(4)
C15 O3 C12 C11 . -1.7(7)
C15 O3 C12 C13 . 178.9(5)
C11 C12 C13 C14 . 1.5(7)
O3 C12 C13 C14 . -179.0(4)
C12 C13 C14 C9 . -1.1(7)
C10 C9 C14 C13 . 0.5(7)
N1 C9 C14 C13 . -178.6(4)
