#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:33:26 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179535 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/04/4500416.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_4500416
loop_
_publ_author_name
'Collas, Alain'
'Bagrowska, Izabela'
'Aleksandrzak, Krzysztof'
'Zeller, Matthias'
'Blockhuys, Frank'
_publ_section_title
;
 Competition between Methoxy-Based and Pyrazine-Based Synthons in
 Methoxy-Substituted Distyrylpyrazines
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1299
_journal_paper_doi               10.1021/cg101523f
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         'C26 H28 N2 O6'
_chemical_formula_sum            'C26 H28 N2 O6'
_chemical_formula_weight         464.50
_chemical_name_systematic
;
 ?
;
_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                 98.52(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.371(2)
_cell_length_b                   13.193(4)
_cell_length_c                   20.695(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.01
_cell_measurement_theta_min      5.20
_cell_volume                     1180.2(7)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1996)'
_computing_molecular_graphics
'ORTEP (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material
'WINGX (Farrugia, 1999) and PLATON (Spek, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'ω/2τ 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  0.0874
_diffrn_reflns_av_sigmaI/netI    0.0992
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4801
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        5
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1571
_refine_ls_R_factor_gt           0.0483
_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)+(0.0594P)²+0.1671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1557
_reflns_number_gt                945
_reflns_number_total             2162
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg101523f_si_004.cif
_cod_data_source_block           new
_cod_depositor_comments
;
The following automatic conversions were performed:

'_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      'P 21/c'
_cod_database_code               4500416
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
C1 C -0.1190(8) 0.1561(2) 0.38011(15) 0.0459(9) Uani 1 1 d .
C2 C -0.0447(8) 0.1679(2) 0.31767(15) 0.0466(9) Uani 1 1 d .
H2 H 0.0281 0.2299 0.3050 0.056 Uiso 1 1 calc R
C3 C -0.0786(8) 0.0876(2) 0.27425(14) 0.0414(8) Uani 1 1 d .
C4 C -0.1844(8) -0.0054(2) 0.29347(15) 0.0420(8) Uani 1 1 d .
C5 C -0.2570(8) -0.0175(2) 0.35490(16) 0.0490(9) Uani 1 1 d .
C6 C -0.2286(9) 0.0635(3) 0.39845(16) 0.0539(10) Uani 1 1 d .
H6 H -0.2833 0.0554 0.4399 0.065 Uiso 1 1 calc R
C7 C -0.1038(9) 0.2405(3) 0.42614(15) 0.0513(10) Uani 1 1 d .
H7 H -0.1825 0.2291 0.4649 0.062 Uiso 1 1 calc R
C8 C 0.0116(9) 0.3319(3) 0.41806(15) 0.0552(10) Uani 1 1 d .
H8 H 0.1037 0.3423 0.3809 0.066 Uiso 1 1 calc R
C9 C 0.0062(9) 0.4170(2) 0.46236(15) 0.0516(10) Uani 1 1 d .
C10 C -0.1157(10) 0.4886(3) 0.55426(15) 0.0620(11) Uani 1 1 d .
H10 H -0.1958 0.4832 0.5933 0.074 Uiso 1 1 calc R
C31 C 0.1005(11) 0.1844(3) 0.18979(17) 0.0714(12) Uani 1 1 d .
H31A H -0.0372 0.2394 0.1952 0.107 Uiso 1 1 calc R
H31B H 0.1230 0.1783 0.1445 0.107 Uiso 1 1 calc R
H31C H 0.2989 0.1973 0.2151 0.107 Uiso 1 1 calc R
C41 C -0.5139(9) -0.0974(3) 0.2154(2) 0.0701(12) Uani 1 1 d .
H41A H -0.6555 -0.1084 0.2460 0.105 Uiso 1 1 calc R
H41B H -0.5191 -0.1546 0.1866 0.105 Uiso 1 1 calc R
H41C H -0.5726 -0.0374 0.1904 0.105 Uiso 1 1 calc R
C51 C -0.4665(10) -0.1279(3) 0.42864(17) 0.0728(12) Uani 1 1 d .
H51A H -0.3032 -0.1143 0.4640 0.109 Uiso 1 1 calc R
H51B H -0.5328 -0.1970 0.4311 0.109 Uiso 1 1 calc R
H51C H -0.6375 -0.0834 0.4317 0.109 Uiso 1 1 calc R
N1 N -0.1127(8) 0.4058(2) 0.51767(13) 0.0614(9) Uani 1 1 d .
O3 O -0.0228(6) 0.09283(16) 0.21128(10) 0.0543(7) Uani 1 1 d .
O4 O -0.2101(5) -0.08541(16) 0.24976(10) 0.0481(6) Uani 1 1 d .
O5 O -0.3590(7) -0.11198(18) 0.36919(12) 0.0686(8) Uani 1 1 d .
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_site_symmetry_1
_geom_angle_site_symmetry_3
C6 C1 C2 119.4(3) . .
C6 C1 C7 118.6(3) . .
C2 C1 C7 121.9(3) . .
C3 C2 C1 120.2(3) . .
C3 C2 H2 119.9 . .
C1 C2 H2 119.9 . .
O3 C3 C2 124.4(3) . .
O3 C3 C4 115.6(3) . .
C2 C3 C4 119.9(3) . .
C5 C4 O4 120.8(3) . .
C5 C4 C3 120.2(3) . .
O4 C4 C3 119.0(3) . .
C4 C5 O5 115.8(3) . .
C4 C5 C6 120.2(3) . .
O5 C5 C6 124.0(3) . .
C1 C6 C5 120.1(3) . .
C1 C6 H6 120.0 . .
C5 C6 H6 120.0 . .
C8 C7 C1 126.3(3) . .
C8 C7 H7 116.9 . .
C1 C7 H7 116.9 . .
C7 C8 C9 125.5(3) . .
C7 C8 H8 117.2 . .
C9 C8 H8 117.2 . .
N1 C9 C10 120.2(3) . 3_566
N1 C9 C8 120.0(3) . .
C10 C9 C8 119.8(3) 3_566 .
N1 C10 C9 124.0(3) . 3_566
N1 C10 H10 118.0 . .
C9 C10 H10 118.0 3_566 .
O3 C31 H31A 109.5 . .
O3 C31 H31B 109.5 . .
H31A C31 H31B 109.5 . .
O3 C31 H31C 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
O4 C41 H41A 109.5 . .
O4 C41 H41B 109.5 . .
H41A C41 H41B 109.5 . .
O4 C41 H41C 109.5 . .
H41A C41 H41C 109.5 . .
H41B C41 H41C 109.5 . .
O5 C51 H51A 109.5 . .
O5 C51 H51B 109.5 . .
H51A C51 H51B 109.5 . .
O5 C51 H51C 109.5 . .
H51A C51 H51C 109.5 . .
H51B C51 H51C 109.5 . .
C10 N1 C9 115.8(3) . .
C3 O3 C31 118.2(2) . .
C4 O4 C41 113.1(3) . .
C5 O5 C51 119.3(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.386(5) .
C1 C2 1.387(4) .
C1 C7 1.460(4) .
C2 C3 1.382(4) .
C2 H2 0.9300 .
C3 O3 1.363(3) .
C3 C4 1.390(4) .
C4 C5 1.364(4) .
C4 O4 1.383(3) .
C5 O5 1.371(4) .
C5 C6 1.391(4) .
C6 H6 0.9300 .
C7 C8 1.326(5) .
C7 H7 0.9300 .
C8 C9 1.452(4) .
C8 H8 0.9300 .
C9 N1 1.334(4) .
C9 C10 1.396(5) 3_566
C10 N1 1.330(4) .
C10 C9 1.396(5) 3_566
C10 H10 0.9300 .
C31 O3 1.420(4) .
C31 H31A 0.9600 .
C31 H31B 0.9600 .
C31 H31C 0.9600 .
C41 O4 1.419(4) .
C41 H41A 0.9600 .
C41 H41B 0.9600 .
C41 H41C 0.9600 .
C51 O5 1.396(4) .
C51 H51A 0.9600 .
C51 H51B 0.9600 .
C51 H51C 0.9600 .
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_site_symmetry_1
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -0.3(5) . .
C7 C1 C2 C3 -176.4(3) . .
C1 C2 C3 O3 177.4(3) . .
C1 C2 C3 C4 -0.7(5) . .
O3 C3 C4 C5 -177.8(3) . .
C2 C3 C4 C5 0.5(5) . .
O3 C3 C4 O4 3.1(4) . .
C2 C3 C4 O4 -178.6(3) . .
O4 C4 C5 O5 -0.9(5) . .
C3 C4 C5 O5 -180.0(3) . .
O4 C4 C5 C6 179.7(3) . .
C3 C4 C5 C6 0.7(5) . .
C2 C1 C6 C5 1.4(5) . .
C7 C1 C6 C5 177.6(3) . .
C4 C5 C6 C1 -1.6(5) . .
O5 C5 C6 C1 179.1(3) . .
C6 C1 C7 C8 175.7(4) . .
C2 C1 C7 C8 -8.2(6) . .
C1 C7 C8 C9 175.6(3) . .
C7 C8 C9 N1 2.4(6) . .
C7 C8 C9 C10 -175.3(4) . 3_566
C9 C10 N1 C9 0.5(6) 3_566 .
C10 C9 N1 C10 -0.4(6) 3_566 .
C8 C9 N1 C10 -178.2(3) . .
C2 C3 O3 C31 4.9(5) . .
C4 C3 O3 C31 -176.9(3) . .
C5 C4 O4 C41 84.4(4) . .
C3 C4 O4 C41 -96.5(4) . .
C4 C5 O5 C51 -173.8(3) . .
C6 C5 O5 C51 5.5(5) . .
