#------------------------------------------------------------------------------
#$Date: 2016-02-19 23:18:51 +0100 (vie 19 de feb de 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/94/2019405.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_2019405
loop_
_publ_author_name
'Garay, Alexander'
'Abonía, Rodrigo'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 Comparison of N-(3,4,5-trimethoxybenzylidene)naphthalen-1-amine
 and its reduction product
 N-(3,4,5-trimethoxybenzyl)naphthalen-1-amine
;
_journal_coeditor_code           SF3215
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              210
_journal_page_last               215
_journal_paper_doi               10.1107/S2053229613034839
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C20 H21 N O3'
_chemical_formula_moiety         'C20 H21 N O3'
_chemical_formula_sum            'C20 H21 N O3'
_chemical_formula_weight         323.38
_chemical_name_systematic
;
N-(3,4,5-trimethoxybenzyl)naphthalen-1-amine
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4460(17)
_cell_length_b                   11.0868(18)
_cell_length_c                   15.8195(16)
_cell_measurement_reflns_used    2170
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.65
_cell_volume                     1656.7(4)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al., 2000)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16040
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.83
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0460P)²+0.4465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                1799
_reflns_number_total             2168
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf3215sup1.cif
_cod_data_source_block           II
_cod_database_code               2019405
_cod_database_fobs_code          2019405
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -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_symmetry_multiplicity
C C1 0.1583(2) 0.6593(2) 0.39872(15) 0.0225(5) Uani d . 1 1
C C2 0.1231(3) 0.5526(2) 0.43806(15) 0.0253(5) Uani d . 1 1
H H2 0.1945 0.5075 0.4662 0.030 Uiso calc R 1 1
C C3 -0.0173(3) 0.5090(2) 0.43722(16) 0.0279(6) Uani d . 1 1
H H3 -0.0385 0.4349 0.4646 0.033 Uiso calc R 1 1
C C4 -0.1232(3) 0.5712(2) 0.39793(16) 0.0280(5) Uani d . 1 1
H H4 -0.2171 0.5405 0.3981 0.034 Uiso calc R 1 1
C C5 -0.1997(3) 0.7497(2) 0.31591(17) 0.0316(6) Uani d . 1 1
H H5 -0.2938 0.7195 0.3145 0.038 Uiso calc R 1 1
C C6 -0.1700(3) 0.8580(2) 0.27839(17) 0.0317(6) Uani d . 1 1
H H6 -0.2430 0.9017 0.2507 0.038 Uiso calc R 1 1
C C7 -0.0316(3) 0.9049(2) 0.28072(17) 0.0311(6) Uani d . 1 1
H H7 -0.0116 0.9808 0.2555 0.037 Uiso calc R 1 1
C C8 0.0740(3) 0.8412(2) 0.31924(16) 0.0282(6) Uani d . 1 1
H H8 0.1670 0.8737 0.3202 0.034 Uiso calc R 1 1
C C9 0.0484(3) 0.7277(2) 0.35786(15) 0.0238(5) Uani d . 1 1
C C10 -0.0924(3) 0.6816(2) 0.35684(16) 0.0252(5) Uani d . 1 1
N N1 0.2942(2) 0.70652(18) 0.40028(13) 0.0251(4) Uani d . 1 1
H H1 0.3276 0.7576 0.3547 0.030 Uiso d R 1 1
C C17 0.4065(3) 0.6527(2) 0.44923(16) 0.0256(5) Uani d . 1 1
H H17A 0.3703 0.6377 0.5070 0.031 Uiso calc R 1 1
H H17B 0.4843 0.7122 0.4540 0.031 Uiso calc R 1 1
C C11 0.4685(2) 0.5354(2) 0.41586(15) 0.0239(5) Uani d . 1 1
C C12 0.4780(3) 0.5146(2) 0.32929(15) 0.0245(5) Uani d . 1 1
H H12 0.4419 0.5721 0.2903 0.029 Uiso calc R 1 1
C C13 0.5407(3) 0.4088(2) 0.30039(14) 0.0222(5) Uani d . 1 1
C C14 0.5933(3) 0.3236(2) 0.35702(16) 0.0240(5) Uani d . 1 1
C C15 0.5822(3) 0.3443(2) 0.44355(16) 0.0258(5) Uani d . 1 1
C C16 0.5209(3) 0.4509(2) 0.47294(16) 0.0259(5) Uani d . 1 1
H H16 0.5150 0.4659 0.5320 0.031 Uiso calc R 1 1
O O13 0.55711(19) 0.37999(15) 0.21667(11) 0.0282(4) Uani d . 1 1
C C23 0.5280(3) 0.4733(2) 0.15638(16) 0.0334(6) Uani d . 1 1
H H23A 0.4263 0.4908 0.1562 0.050 Uiso calc R 1 1
H H23B 0.5573 0.4465 0.1000 0.050 Uiso calc R 1 1
H H23C 0.5805 0.5463 0.1718 0.050 Uiso calc R 1 1
O O14 0.65142(19) 0.21920(15) 0.32366(11) 0.0299(4) Uani d . 1 1
C C24 0.7927(3) 0.1905(3) 0.35080(17) 0.0333(6) Uani d . 1 1
H H24A 0.8464 0.2652 0.3591 0.050 Uiso calc R 1 1
H H24B 0.8393 0.1410 0.3077 0.050 Uiso calc R 1 1
H H24C 0.7886 0.1456 0.4041 0.050 Uiso calc R 1 1
O O15 0.6316(2) 0.25456(17) 0.49517(12) 0.0350(5) Uani d . 1 1
C C25 0.6763(3) 0.2872(3) 0.57782(16) 0.0371(7) Uani d . 1 1
H H25A 0.7381 0.3580 0.5746 0.056 Uiso calc R 1 1
H H25B 0.7283 0.2199 0.6033 0.056 Uiso calc R 1 1
H H25C 0.5934 0.3062 0.6126 0.056 Uiso calc R 1 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
_geom_angle_publ_flag
C2 C1 N1 122.7(2) ?
C2 C1 C9 118.7(2) ?
N1 C1 C9 118.5(2) ?
C1 C2 C3 121.1(2) ?
C1 C2 H2 119.4 ?
C3 C2 H2 119.4 ?
C4 C3 C2 121.4(2) ?
C4 C3 H3 119.3 ?
C2 C3 H3 119.3 ?
C3 C4 C10 119.7(2) ?
C3 C4 H4 120.1 ?
C10 C4 H4 120.1 ?
C6 C5 C10 121.1(2) ?
C6 C5 H5 119.4 ?
C10 C5 H5 119.4 ?
C5 C6 C7 120.2(2) ?
C5 C6 H6 119.9 ?
C7 C6 H6 119.9 ?
C8 C7 C6 119.9(2) ?
C8 C7 H7 120.0 ?
C6 C7 H7 120.0 ?
C7 C8 C9 121.7(2) ?
C7 C8 H8 119.1 ?
C9 C8 H8 119.1 ?
C8 C9 C10 118.2(2) ?
C8 C9 C1 122.5(2) ?
C10 C9 C1 119.3(2) ?
C4 C10 C5 121.5(2) ?
C4 C10 C9 119.8(2) ?
C5 C10 C9 118.8(2) ?
C1 N1 C17 122.3(2) y
C1 N1 H1 120.6 ?
C17 N1 H1 113.7 ?
N1 C17 C11 116.8(2) y
N1 C17 H17A 108.1 ?
C11 C17 H17A 108.1 ?
N1 C17 H17B 108.1 ?
C11 C17 H17B 108.1 ?
H17A C17 H17B 107.3 ?
C12 C11 C16 120.3(2) ?
C12 C11 C17 120.6(2) ?
C16 C11 C17 119.1(2) ?
C13 C12 C11 119.4(2) ?
C13 C12 H12 120.3 ?
C11 C12 H12 120.3 ?
O13 C13 C12 124.2(2) y
O13 C13 C14 115.0(2) y
C12 C13 C14 120.8(2) ?
O14 C14 C13 117.6(2) y
O14 C14 C15 122.8(2) y
C15 C14 C13 119.6(2) ?
O15 C15 C14 116.2(2) y
O15 C15 C16 123.9(2) y
C14 C15 C16 119.9(2) ?
C11 C16 C15 120.1(2) ?
C11 C16 H16 120.0 ?
C15 C16 H16 120.0 ?
C13 O13 C23 116.94(19) ?
O13 C23 H23A 109.5 ?
O13 C23 H23B 109.5 ?
H23A C23 H23B 109.5 ?
O13 C23 H23C 109.5 ?
H23A C23 H23C 109.5 ?
H23B C23 H23C 109.5 ?
C14 O14 C24 116.0(2) ?
O14 C24 H24A 109.5 ?
O14 C24 H24B 109.5 ?
H24A C24 H24B 109.5 ?
O14 C24 H24C 109.5 ?
H24A C24 H24C 109.5 ?
H24B C24 H24C 109.5 ?
C15 O15 C25 117.7(2) ?
O15 C25 H25A 109.5 ?
O15 C25 H25B 109.5 ?
H25A C25 H25B 109.5 ?
O15 C25 H25C 109.5 ?
H25A C25 H25C 109.5 ?
H25B C25 H25C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.378(3) ?
C1 N1 1.386(3) ?
C1 C9 1.440(3) ?
C2 C3 1.411(4) ?
C2 H2 0.9500 ?
C3 C4 1.364(4) ?
C3 H3 0.9500 ?
C4 C10 1.417(4) ?
C4 H4 0.9500 ?
C5 C6 1.369(4) ?
C5 C10 1.420(4) ?
C5 H5 0.9500 ?
C6 C7 1.408(4) ?
C6 H6 0.9500 ?
C7 C8 1.365(4) ?
C7 H7 0.9500 ?
C8 C9 1.419(3) ?
C8 H8 0.9500 ?
C9 C10 1.425(3) ?
N1 C17 1.443(3) y
N1 H1 0.9698 ?
C17 C11 1.520(3) ?
C17 H17A 0.9900 ?
C17 H17B 0.9900 ?
C11 C12 1.392(3) ?
C11 C16 1.392(3) ?
C12 C13 1.392(3) ?
C12 H12 0.9500 ?
C13 O13 1.371(3) ?
C13 C14 1.393(3) ?
C14 O14 1.385(3) ?
C14 C15 1.392(4) ?
C15 O15 1.369(3) ?
C15 C16 1.396(4) ?
C16 H16 0.9500 ?
O13 C23 1.434(3) ?
C23 H23A 0.9800 ?
C23 H23B 0.9800 ?
C23 H23C 0.9800 ?
O14 C24 1.437(3) ?
C24 H24A 0.9800 ?
C24 H24B 0.9800 ?
C24 H24C 0.9800 ?
O15 C25 1.421(3) ?
C25 H25A 0.9800 ?
C25 H25B 0.9800 ?
C25 H25C 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
_geom_hbond_publ_flag
N1 H1 O13 4_655 0.97 2.07 3.016(3) 163 y
C12 H12 O14 4_655 0.95 2.59 3.535(3) 176 y
C4 H4 Cg1 1_455 0.95 2.69 3.632(3) 173 y
C7 H7 Cg2 4_555 0.95 2.86 3.677(3) 145 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
_geom_torsion_publ_flag
N1 C1 C2 C3 178.1(2) ?
C9 C1 C2 C3 1.3(4) ?
C1 C2 C3 C4 -0.4(4) ?
C2 C3 C4 C10 0.1(4) ?
C10 C5 C6 C7 -0.8(4) ?
C5 C6 C7 C8 1.1(4) ?
C6 C7 C8 C9 -0.2(4) ?
C7 C8 C9 C10 -1.0(4) ?
C7 C8 C9 C1 180.0(2) ?
C2 C1 C9 C8 177.0(2) ?
N1 C1 C9 C8 0.1(3) ?
C2 C1 C9 C10 -2.0(3) ?
N1 C1 C9 C10 -179.0(2) ?
C3 C4 C10 C5 -179.4(2) ?
C3 C4 C10 C9 -0.9(3) ?
C6 C5 C10 C4 178.1(2) ?
C6 C5 C10 C9 -0.4(4) ?
C8 C9 C10 C4 -177.3(2) ?
C1 C9 C10 C4 1.8(3) ?
C8 C9 C10 C5 1.3(3) ?
C1 C9 C10 C5 -179.6(2) ?
C2 C1 N1 C17 -5.3(4) y
C9 C1 N1 C17 171.5(2) ?
C1 N1 C17 C11 73.6(3) y
N1 C17 C11 C12 33.4(3) y
N1 C17 C11 C16 -149.0(2) ?
C16 C11 C12 C13 -0.2(4) ?
C17 C11 C12 C13 177.3(2) ?
C11 C12 C13 O13 -179.1(2) ?
C11 C12 C13 C14 0.3(4) ?
O13 C13 C14 O14 -2.0(3) ?
C12 C13 C14 O14 178.6(2) ?
O13 C13 C14 C15 179.9(2) ?
C12 C13 C14 C15 0.5(4) ?
O14 C14 C15 O15 -0.3(4) ?
C13 C14 C15 O15 177.7(2) ?
O14 C14 C15 C16 -179.2(2) ?
C13 C14 C15 C16 -1.2(4) ?
C12 C11 C16 C15 -0.5(4) ?
C17 C11 C16 C15 -178.1(2) ?
O15 C15 C16 C11 -177.5(2) ?
C14 C15 C16 C11 1.3(4) ?
C12 C13 O13 C23 10.2(3) y
C14 C13 O13 C23 -169.2(2) ?
C15 C14 O14 C24 -55.7(3) ?
C13 C14 O14 C24 126.2(2) y
C14 C15 O15 C25 154.8(2) ?
C16 C15 O15 C25 -26.3(4) y
