#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/12/2221245.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_2221245
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Kia, Reza'
'Kargar, Hadi'
'Jamshidvand, Arezoo'
_publ_section_title
;
 A second tricilinc polymorph of
 6,6'-diethoxy-2,2'-[propane-1,2-diylbis(nitrilomethylidyne)]diphenol
;
_journal_coeditor_code           AT2736
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o722
_journal_page_last               o723
_journal_paper_doi               10.1107/S1600536809008137
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H26 N2 O4'
_chemical_formula_moiety         'C21 H26 N2 O4'
_chemical_formula_sum            'C21 H26 N2 O4'
_chemical_formula_weight         370.44
_chemical_name_systematic
;
6,6'-diethoxy-2,2'-[propane-1,2-diylbis(nitrilomethylidyne)]diphenol
;
_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           SHELXL-97
_cell_angle_alpha                107.4320(10)
_cell_angle_beta                 108.4870(10)
_cell_angle_gamma                95.9790(10)
_cell_formula_units_Z            2
_cell_length_a                   8.9729(2)
_cell_length_b                   10.7008(4)
_cell_length_c                   11.3633(2)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    100
_cell_measurement_theta_max      33.91
_cell_measurement_theta_min      2.45
_cell_volume                     963.03(5)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type
;
Bruker SMART APEXII 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  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19581
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9783
_exptl_absorpt_correction_T_min  0.9516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         5527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0795P)²+0.2658P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1357
_reflns_number_gt                4721
_reflns_number_total             5527
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2736.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               2221245
_cod_database_fobs_code          2221245
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_disorder_assembly
_atom_site_disorder_group
O O1 0.45973(9) 0.68396(7) 1.04387(8) 0.02067(16) Uani d . 1 . .
H H1 0.3996 0.6074 0.9989 0.031 Uiso calc R 1 . .
O O2 0.23678(10) 0.61221(7) 0.56112(7) 0.02165(17) Uani d . 1 . .
H H2 0.2199 0.5617 0.6018 0.032 Uiso calc R 1 . .
O O3 0.60593(9) 0.93704(7) 1.19014(7) 0.02040(16) Uani d . 1 . .
O O4 0.30071(10) 0.74269(7) 0.41348(7) 0.02157(17) Uani d . 1 . .
N N1 0.20357(10) 0.51029(9) 0.87252(9) 0.01932(18) Uani d . 1 . .
N N2 0.22170(11) 0.39204(9) 0.61688(9) 0.01981(18) Uani d . 1 . .
C C1 0.37342(12) 0.77863(10) 1.03131(9) 0.01695(19) Uani d . 1 . .
C C2 0.45003(12) 0.91483(10) 1.10727(10) 0.01745(19) Uani d . 1 . .
C C3 0.36454(13) 1.01381(10) 1.09335(10) 0.0202(2) Uani d . 1 . .
H H3A 0.4165 1.1055 1.1421 0.024 Uiso calc R 1 . .
C C4 0.20267(13) 0.98033(11) 1.00838(11) 0.0230(2) Uani d . 1 . .
H H4A 0.1456 1.0492 1.0003 0.028 Uiso calc R 1 . .
C C5 0.12610(12) 0.84751(11) 0.93638(11) 0.0218(2) Uani d . 1 . .
H H5A 0.0158 0.8249 0.8801 0.026 Uiso calc R 1 . .
C C6 0.21104(12) 0.74568(10) 0.94623(10) 0.01782(19) Uani d . 1 . .
C C7 0.13033(12) 0.60568(10) 0.86605(10) 0.0193(2) Uani d . 1 . .
H H7A 0.0211 0.5852 0.8079 0.023 Uiso calc R 1 . .
C C8 0.11726(12) 0.37212(10) 0.78846(10) 0.0197(2) Uani d . 1 . .
H H8A 0.0055 0.3712 0.7325 0.024 Uiso calc R 1 . .
C C9 0.20882(13) 0.31383(10) 0.70025(10) 0.0209(2) Uani d . 1 . .
H H9A 0.3182 0.3127 0.7564 0.025 Uiso calc R 1 . .
H H9B 0.1525 0.2200 0.6432 0.025 Uiso calc R 1 . .
C C10 0.25539(12) 0.33633(10) 0.51501(10) 0.0195(2) Uani d . 1 . .
H H10A 0.2624 0.2448 0.4936 0.023 Uiso calc R 1 . .
C C11 0.28343(12) 0.40753(10) 0.43059(10) 0.01798(19) Uani d . 1 . .
C C12 0.32606(13) 0.34087(11) 0.32285(10) 0.0224(2) Uani d . 1 . .
H H12A 0.3319 0.2492 0.3041 0.027 Uiso calc R 1 . .
C C13 0.35938(13) 0.40746(11) 0.24449(10) 0.0236(2) Uani d . 1 . .
H H13A 0.3881 0.3617 0.1721 0.028 Uiso calc R 1 . .
C C14 0.35108(12) 0.54260(11) 0.27131(10) 0.0211(2) Uani d . 1 . .
H H14A 0.3732 0.5880 0.2165 0.025 Uiso calc R 1 . .
C C15 0.31054(12) 0.61053(10) 0.37785(10) 0.01799(19) Uani d . 1 . .
C C16 0.27562(11) 0.54322(10) 0.45865(9) 0.01716(19) Uani d . 1 . .
C C17 0.11095(14) 0.29050(11) 0.87711(11) 0.0251(2) Uani d . 1 . .
H H17A 0.0583 0.3321 0.9376 0.038 Uiso calc R 1 . .
H H17B 0.2207 0.2884 0.9286 0.038 Uiso calc R 1 . .
H H17C 0.0497 0.1987 0.8220 0.038 Uiso calc R 1 . .
C C18 0.68435(13) 1.07531(10) 1.27022(10) 0.0207(2) Uani d . 1 . .
H H18A 0.6284 1.1129 1.3306 0.025 Uiso calc R 1 . .
H H18B 0.6818 1.1295 1.2129 0.025 Uiso calc R 1 . .
C C19 0.85652(13) 1.07880(11) 1.34933(11) 0.0250(2) Uani d . 1 . .
H H19A 0.9117 1.1714 1.4071 0.038 Uiso calc R 1 . .
H H19B 0.9119 1.0446 1.2887 0.038 Uiso calc R 1 . .
H H19C 0.8576 1.0226 1.4036 0.038 Uiso calc R 1 . .
C C20 0.32265(13) 0.81235(11) 0.32824(11) 0.0228(2) Uani d . 1 . .
H H20A 0.2482 0.7626 0.2357 0.027 Uiso calc R 1 . .
H H20B 0.4345 0.8213 0.3305 0.027 Uiso calc R 1 . .
C C21 0.28754(16) 0.94927(12) 0.37877(13) 0.0284(2) Uani d . 1 . .
H H21A 0.3039 1.0011 0.3242 0.043 Uiso calc R 1 . .
H H21B 0.3602 0.9965 0.4710 0.043 Uiso calc R 1 . .
H H21C 0.1757 0.9390 0.3739 0.043 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
_geom_angle_publ_flag
C1 O1 H1 . . 109.5 ?
C16 O2 H2 . . 109.5 ?
C2 O3 C18 . . 116.03(8) ?
C15 O4 C20 . . 116.95(8) ?
C7 N1 C8 . . 118.97(9) ?
C10 N2 C9 . . 117.69(9) ?
O1 C1 C6 . . 122.09(9) ?
O1 C1 C2 . . 118.39(8) ?
C6 C1 C2 . . 119.52(9) ?
O3 C2 C3 . . 125.27(9) ?
O3 C2 C1 . . 115.48(9) ?
C3 C2 C1 . . 119.25(9) ?
C2 C3 C4 . . 120.94(9) ?
C2 C3 H3A . . 119.5 ?
C4 C3 H3A . . 119.5 ?
C5 C4 C3 . . 120.10(10) ?
C5 C4 H4A . . 119.9 ?
C3 C4 H4A . . 119.9 ?
C4 C5 C6 . . 120.06(10) ?
C4 C5 H5A . . 120.0 ?
C6 C5 H5A . . 120.0 ?
C5 C6 C1 . . 120.10(9) ?
C5 C6 C7 . . 119.59(9) ?
C1 C6 C7 . . 120.30(9) ?
N1 C7 C6 . . 121.39(9) ?
N1 C7 H7A . . 119.3 ?
C6 C7 H7A . . 119.3 ?
N1 C8 C9 . . 108.28(8) ?
N1 C8 C17 . . 108.78(8) ?
C9 C8 C17 . . 109.96(9) ?
N1 C8 H8A . . 109.9 ?
C9 C8 H8A . . 109.9 ?
C17 C8 H8A . . 109.9 ?
N2 C9 C8 . . 111.50(8) ?
N2 C9 H9A . . 109.3 ?
C8 C9 H9A . . 109.3 ?
N2 C9 H9B . . 109.3 ?
C8 C9 H9B . . 109.3 ?
H9A C9 H9B . . 108.0 ?
N2 C10 C11 . . 122.60(9) ?
N2 C10 H10A . . 118.7 ?
C11 C10 H10A . . 118.7 ?
C16 C11 C12 . . 119.72(10) ?
C16 C11 C10 . . 120.87(9) ?
C12 C11 C10 . . 119.35(9) ?
C13 C12 C11 . . 120.54(9) ?
C13 C12 H12A . . 119.7 ?
C11 C12 H12A . . 119.7 ?
C12 C13 C14 . . 120.13(9) ?
C12 C13 H13A . . 119.9 ?
C14 C13 H13A . . 119.9 ?
C15 C14 C13 . . 120.23(10) ?
C15 C14 H14A . . 119.9 ?
C13 C14 H14A . . 119.9 ?
O4 C15 C14 . . 124.90(9) ?
O4 C15 C16 . . 114.95(8) ?
C14 C15 C16 . . 120.15(9) ?
O2 C16 C11 . . 122.22(9) ?
O2 C16 C15 . . 118.56(9) ?
C11 C16 C15 . . 119.22(9) ?
C8 C17 H17A . . 109.5 ?
C8 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C8 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O3 C18 C19 . . 107.74(8) ?
O3 C18 H18A . . 110.2 ?
C19 C18 H18A . . 110.2 ?
O3 C18 H18B . . 110.2 ?
C19 C18 H18B . . 110.2 ?
H18A C18 H18B . . 108.5 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
O4 C20 C21 . . 106.98(9) ?
O4 C20 H20A . . 110.3 ?
C21 C20 H20A . . 110.3 ?
O4 C20 H20B . . 110.3 ?
C21 C20 H20B . . 110.3 ?
H20A C20 H20B . . 108.6 ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 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 C1 . 1.3514(12) ?
O1 H1 . 0.8400 ?
O2 C16 . 1.3484(11) ?
O2 H2 . 0.8400 ?
O3 C2 . 1.3643(12) ?
O3 C18 . 1.4432(12) ?
O4 C15 . 1.3701(12) ?
O4 C20 . 1.4338(13) ?
N1 C7 . 1.2780(14) ?
N1 C8 . 1.4644(13) ?
N2 C10 . 1.2777(13) ?
N2 C9 . 1.4614(14) ?
C1 C6 . 1.4062(13) ?
C1 C2 . 1.4153(13) ?
C2 C3 . 1.3885(14) ?
C3 C4 . 1.4018(15) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.3802(15) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.4046(14) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.4617(14) ?
C7 H7A . 0.9500 ?
C8 C9 . 1.5242(15) ?
C8 C17 . 1.5277(15) ?
C8 H8A . 1.0000 ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.4542(15) ?
C10 H10A . 0.9500 ?
C11 C16 . 1.4046(13) ?
C11 C12 . 1.4087(14) ?
C12 C13 . 1.3765(16) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.4008(15) ?
C13 H13A . 0.9500 ?
C14 C15 . 1.3905(14) ?
C14 H14A . 0.9500 ?
C15 C16 . 1.4112(14) ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 C19 . 1.5110(15) ?
C18 H18A . 0.9900 ?
C18 H18B . 0.9900 ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
C20 C21 . 1.5107(16) ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 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
O1 H1 N1 . 0.8400 1.8300 2.5752(13) 146.00 y
O2 H2 N2 . 0.8400 1.8800 2.6178(13) 147.00 y
C9 H9A O1 2_667 0.9900 2.4900 3.4293(14) 159.00 y
C18 H18b Cg1 2_566 0.9900 2.9800 3.8340(12) 142.00 y
C7 H7A Cg2 2_677 0.9600 2.7200 3.5554(12) 176.00 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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C18 O3 C2 C3 . . . . 1.11(15) ?
C18 O3 C2 C1 . . . . -178.73(8) ?
O1 C1 C2 O3 . . . . -1.69(13) ?
C6 C1 C2 O3 . . . . 177.98(9) ?
O1 C1 C2 C3 . . . . 178.45(9) ?
C6 C1 C2 C3 . . . . -1.88(15) ?
O3 C2 C3 C4 . . . . -177.92(10) ?
C1 C2 C3 C4 . . . . 1.92(15) ?
C2 C3 C4 C5 . . . . -0.39(17) ?
C3 C4 C5 C6 . . . . -1.17(16) ?
C4 C5 C6 C1 . . . . 1.18(16) ?
C4 C5 C6 C7 . . . . -177.88(9) ?
O1 C1 C6 C5 . . . . -179.99(9) ?
C2 C1 C6 C5 . . . . 0.35(15) ?
O1 C1 C6 C7 . . . . -0.94(15) ?
C2 C1 C6 C7 . . . . 179.41(9) ?
C8 N1 C7 C6 . . . . -179.15(9) ?
C5 C6 C7 N1 . . . . -179.86(10) ?
C1 C6 C7 N1 . . . . 1.08(15) ?
C7 N1 C8 C9 . . . . 121.02(10) ?
C7 N1 C8 C17 . . . . -119.50(10) ?
C10 N2 C9 C8 . . . . -161.52(9) ?
N1 C8 C9 N2 . . . . -59.47(11) ?
C17 C8 C9 N2 . . . . -178.20(8) ?
C9 N2 C10 C11 . . . . -175.17(9) ?
N2 C10 C11 C16 . . . . 0.46(15) ?
N2 C10 C11 C12 . . . . 177.59(10) ?
C16 C11 C12 C13 . . . . -0.30(15) ?
C10 C11 C12 C13 . . . . -177.47(9) ?
C11 C12 C13 C14 . . . . -0.02(16) ?
C12 C13 C14 C15 . . . . 0.56(16) ?
C20 O4 C15 C14 . . . . 4.75(14) ?
C20 O4 C15 C16 . . . . -175.21(8) ?
C13 C14 C15 O4 . . . . 179.28(9) ?
C13 C14 C15 C16 . . . . -0.76(15) ?
C12 C11 C16 O2 . . . . -179.44(9) ?
C10 C11 C16 O2 . . . . -2.33(15) ?
C12 C11 C16 C15 . . . . 0.10(14) ?
C10 C11 C16 C15 . . . . 177.22(9) ?
O4 C15 C16 O2 . . . . -0.05(13) ?
C14 C15 C16 O2 . . . . 179.99(9) ?
O4 C15 C16 C11 . . . . -179.61(8) ?
C14 C15 C16 C11 . . . . 0.43(14) ?
C2 O3 C18 C19 . . . . -177.40(9) ?
C15 O4 C20 C21 . . . . 173.58(9) ?
