#------------------------------------------------------------------------------
#$Date: 2017-02-19 21:08:33 +0200 (Sun, 19 Feb 2017) $
#$Revision: 192306 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/37/2013770.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_2013770
loop_
_publ_author_name
'Reglinski, John'
'Taylor, Michelle K'
'Kennedy, Alan R'
_publ_section_title
;
 N,N'-Bis(2-methoxybenzylidene) adducts of
 ethane-1,2-diamine, propane-1,3-diamine and butane-1,4-diamine
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o169
_journal_page_last               o172
_journal_paper_doi               10.1107/S0108270104001404
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C19 H22 N2 O2'
_chemical_formula_moiety         'C19 H22 N2 O2'
_chemical_formula_sum            'C19 H22 N2 O2'
_chemical_formula_weight         310.39
_chemical_melting_point          75
_chemical_name_common            MeSalpr
_chemical_name_systematic
;
N,N-bis(2-methoxybenzylidene)propane-1,3-diamine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                101.140(2)
_cell_angle_beta                 92.341(2)
_cell_angle_gamma                109.442(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8669(2)
_cell_length_b                   9.9139(3)
_cell_length_c                   10.2724(4)
_cell_measurement_reflns_used    3737
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.0
_cell_volume                     830.05(5)
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)'
_computing_data_reduction        DENZO
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and PLATON (Spek 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement
'SHELXL97 (Sheldrick, 1997) and WinGX (Farrugia, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Nonius Kappa 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  0.063
_diffrn_reflns_av_sigmaI/netI    0.0775
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12958
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.215
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0622P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1216
_reflns_number_gt                2279
_reflns_number_total             3737
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg1727.cif
_cod_data_source_block           II
_cod_depositor_comments
;
 Marking atoms 'Cg1' and 'Cg2' as dummy atoms.

 Antanas Vaitkus,
 2017-02-19

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               2013770
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
O1 0.77317(12) 0.14374(12) 1.07537(10) 0.0282(3) Uani d . 1 . . O
O2 1.05404(13) 0.82837(12) 0.48211(10) 0.0335(3) Uani d . 1 . . O
N1 0.50559(15) 0.15505(14) 0.75501(12) 0.0241(3) Uani d . 1 . . N
N2 0.72851(15) 0.43107(14) 0.49220(12) 0.0269(3) Uani d . 1 . . N
C1 0.46774(19) 0.28801(17) 0.75720(15) 0.0250(4) Uani d . 1 . . C
H1A 0.5282 0.3644 0.8364 0.030 Uiso calc R 1 . . H
H1B 0.3513 0.2668 0.7636 0.030 Uiso calc R 1 . . H
C2 0.51246(18) 0.34378(17) 0.63030(15) 0.0241(4) Uani d . 1 . . C
H2A 0.4581 0.2639 0.5515 0.029 Uiso calc R 1 . . H
H2B 0.4726 0.4255 0.6274 0.029 Uiso calc R 1 . . H
C3 0.69278(18) 0.39654(18) 0.62193(15) 0.0269(4) Uani d . 1 . . C
H3A 0.7465 0.4850 0.6935 0.032 Uiso calc R 1 . . H
H3B 0.7357 0.3195 0.6358 0.032 Uiso calc R 1 . . H
C11 0.62244(17) 0.01624(17) 0.86792(14) 0.0219(4) Uani d . 1 . . C
C12 0.72085(17) 0.01728(17) 0.97853(14) 0.0228(4) Uani d . 1 . . C
C13 0.76131(19) -0.10518(18) 0.98533(15) 0.0280(4) Uani d . 1 . . C
H13 0.8282 -0.1042 1.0604 0.034 Uiso calc R 1 . . H
C14 0.7039(2) -0.22879(19) 0.88232(16) 0.0316(4) Uani d . 1 . . C
H14 0.7313 -0.3126 0.8876 0.038 Uiso calc R 1 . . H
C15 0.60735(19) -0.23176(18) 0.77203(16) 0.0293(4) Uani d . 1 . . C
H15 0.5694 -0.3165 0.7014 0.035 Uiso calc R 1 . . H
C16 0.56651(18) -0.10966(17) 0.76566(15) 0.0253(4) Uani d . 1 . . C
H16 0.4993 -0.1118 0.6903 0.030 Uiso calc R 1 . . H
C17 0.57997(17) 0.14626(17) 0.85944(15) 0.0226(4) Uani d . 1 . . C
H17 0.6093 0.2261 0.9347 0.027 Uiso calc R 1 . . H
C18 0.8520(2) 0.1415(2) 1.19883(15) 0.0340(4) Uani d . 1 . . C
H18A 0.7847 0.0593 1.2341 0.051 Uiso calc R 1 . . H
H18B 0.8696 0.2337 1.2632 0.051 Uiso calc R 1 . . H
H18C 0.9559 0.1300 1.1837 0.051 Uiso calc R 1 . . H
C21 0.87439(17) 0.59806(17) 0.36295(14) 0.0217(4) Uani d . 1 . . C
C22 0.98652(17) 0.73724(17) 0.36087(15) 0.0235(4) Uani d . 1 . . C
C23 1.02586(18) 0.77502(18) 0.24003(15) 0.0256(4) Uani d . 1 . . C
H23 1.0991 0.8698 0.2392 0.031 Uiso calc R 1 . . H
C24 0.95873(19) 0.67495(18) 0.12104(15) 0.0289(4) Uani d . 1 . . C
H24 0.9878 0.7007 0.0388 0.035 Uiso calc R 1 . . H
C25 0.8495(2) 0.53756(19) 0.12092(16) 0.0317(4) Uani d . 1 . . C
H25 0.8039 0.4688 0.0391 0.038 Uiso calc R 1 . . H
C26 0.80752(18) 0.50115(18) 0.24110(15) 0.0267(4) Uani d . 1 . . C
H26 0.7309 0.4074 0.2404 0.032 Uiso calc R 1 . . H
C27 0.83081(17) 0.55534(18) 0.48955(15) 0.0240(4) Uani d . 1 . . C
H27 0.8805 0.6225 0.5714 0.029 Uiso calc R 1 . . H
C28 1.1828(2) 0.9626(2) 0.48021(17) 0.0428(5) Uani d . 1 . . C
H28A 1.2697 0.9397 0.4357 0.064 Uiso calc R 1 . . H
H28B 1.2239 1.0176 0.5720 0.064 Uiso calc R 1 . . H
H28C 1.1423 1.0218 0.4317 0.064 Uiso calc R 1 . . H
Cg1 0.66373 -0.10698 0.87530(6) 0.01 Uiso dum . . . . .
Cg2 0.91709 0.63733 0.24115(6) 0.01 Uiso dum . . . . .
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'
O O 0.0106 0.0060 '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'
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
C12 O1 C18 117.86(13) y
C22 O2 C28 116.49(12) y
C17 N1 C1 117.99(13) y
C27 N2 C3 118.37(13) y
N1 C1 C2 110.05(12) ?
N1 C1 H1A 109.7 ?
C2 C1 H1A 109.7 ?
N1 C1 H1B 109.7 ?
C2 C1 H1B 109.7 ?
H1A C1 H1B 108.2 ?
C3 C2 C1 112.78(12) ?
C3 C2 H2A 109.0 ?
C1 C2 H2A 109.0 ?
C3 C2 H2B 109.0 ?
C1 C2 H2B 109.0 ?
H2A C2 H2B 107.8 ?
N2 C3 C2 110.90(12) ?
N2 C3 H3A 109.5 ?
C2 C3 H3A 109.5 ?
N2 C3 H3B 109.5 ?
C2 C3 H3B 109.5 ?
H3A C3 H3B 108.0 ?
C16 C11 C12 118.70(14) ?
C16 C11 C17 120.75(14) y
C12 C11 C17 120.55(14) y
O1 C12 C13 123.50(14) y
O1 C12 C11 116.29(14) y
C13 C12 C11 120.22(14) ?
C14 C13 C12 119.84(15) ?
C14 C13 H13 120.1 ?
C12 C13 H13 120.1 ?
C15 C14 C13 120.84(16) ?
C15 C14 H14 119.6 ?
C13 C14 H14 119.6 ?
C14 C15 C16 119.25(16) ?
C14 C15 H15 120.4 ?
C16 C15 H15 120.4 ?
C15 C16 C11 121.15(15) ?
C15 C16 H16 119.4 ?
C11 C16 H16 119.4 ?
N1 C17 C11 122.23(14) y
N1 C17 H17 118.9 ?
C11 C17 H17 118.9 ?
O1 C18 H18A 109.5 ?
O1 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
O1 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C26 C21 C22 117.86(14) ?
C26 C21 C27 120.79(14) y
C22 C21 C27 121.34(14) y
O2 C22 C23 123.15(14) y
O2 C22 C21 116.56(13) y
C23 C22 C21 120.28(14) ?
C24 C23 C22 120.16(15) ?
C24 C23 H23 119.9 ?
C22 C23 H23 119.9 ?
C23 C24 C25 120.45(15) ?
C23 C24 H24 119.8 ?
C25 C24 H24 119.8 ?
C26 C25 C24 119.39(15) ?
C26 C25 H25 120.3 ?
C24 C25 H25 120.3 ?
C25 C26 C21 121.82(15) ?
C25 C26 H26 119.1 ?
C21 C26 H26 119.1 ?
N2 C27 C21 121.70(14) y
N2 C27 H27 119.1 ?
C21 C27 H27 119.1 ?
O2 C28 H28A 109.5 ?
O2 C28 H28B 109.5 ?
H28A C28 H28B 109.5 ?
O2 C28 H28C 109.5 ?
H28A C28 H28C 109.5 ?
H28B C28 H28C 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 C12 . 1.3674(17) y
O1 C18 . 1.4307(17) y
O2 C22 . 1.3674(17) y
O2 C28 . 1.4404(19) y
N1 C17 . 1.2688(18) y
N1 C1 . 1.4609(19) y
N2 C27 . 1.270(2) y
N2 C3 . 1.4600(18) y
C1 C2 . 1.529(2) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.520(2) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C11 C16 . 1.395(2) ?
C11 C12 . 1.400(2) ?
C11 C17 . 1.475(2) y
C12 C13 . 1.389(2) ?
C13 C14 . 1.386(2) ?
C13 H13 . 0.95 ?
C14 C15 . 1.382(2) ?
C14 H14 . 0.95 ?
C15 C16 . 1.386(2) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C21 C26 . 1.392(2) ?
C21 C22 . 1.412(2) ?
C21 C27 . 1.471(2) y
C22 C23 . 1.390(2) ?
C23 C24 . 1.382(2) ?
C23 H23 . 0.95 ?
C24 C25 . 1.383(2) ?
C24 H24 . 0.95 ?
C25 C26 . 1.383(2) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?
C27 H27 . 0.95 ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
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
C1 H1B Cg2 2_666 0.99 2.84 3.725 149 y
C23 H23 Cg1 2_766 0.95 3.05 3.944 157 y
C17 H17 Cg1 2_657 0.95 3.23 3.546 102 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
C17 N1 C1 C2 133.21(14)
N1 C1 C2 C3 -66.40(17)
C27 N2 C3 C2 128.37(15)
C1 C2 C3 N2 172.76(13)
C18 O1 C12 C13 -10.2(2)
C18 O1 C12 C11 170.25(13)
C16 C11 C12 O1 179.57(13)
C17 C11 C12 O1 0.0(2)
C16 C11 C12 C13 0.0(2)
C17 C11 C12 C13 -179.52(13)
O1 C12 C13 C14 -179.58(14)
C11 C12 C13 C14 -0.1(2)
C12 C13 C14 C15 0.4(2)
C13 C14 C15 C16 -0.7(2)
C14 C15 C16 C11 0.6(2)
C12 C11 C16 C15 -0.3(2)
C17 C11 C16 C15 179.23(13)
C1 N1 C17 C11 179.40(13)
C16 C11 C17 N1 -7.1(2)
C12 C11 C17 N1 172.39(13)
C28 O2 C22 C23 -6.3(2)
C28 O2 C22 C21 172.46(15)
C26 C21 C22 O2 -177.99(13)
C27 C21 C22 O2 1.2(2)
C26 C21 C22 C23 0.8(2)
C27 C21 C22 C23 179.94(13)
O2 C22 C23 C24 176.90(14)
C21 C22 C23 C24 -1.8(2)
C22 C23 C24 C25 1.3(2)
C23 C24 C25 C26 0.2(2)
C24 C25 C26 C21 -1.2(2)
C22 C21 C26 C25 0.7(2)
C27 C21 C26 C25 -178.42(14)
C3 N2 C27 C21 179.51(13)
C26 C21 C27 N2 -1.8(2)
C22 C21 C27 N2 179.08(14)
