#------------------------------------------------------------------------------
#$Date: 2016-10-08 00:52:34 +0300 (Sat, 08 Oct 2016) $
#$Revision: 187029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/46/7224693.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_7224693
loop_
_publ_author_name
'Safin, Damir A.'
'Robeyns, Koen'
'Babashkina, Maria G.'
'Filinchuk, Yaroslav'
'Rotaru, Aurelian'
'Jureschi, Catalin'
'Mitoraj, Mariusz P.'
'Hooper, James'
'Brela, Mateusz'
'Garcia, Yann'
_publ_section_title
;
 Polymorphism driven optical properties of an anil dye
;
_journal_issue                   38
_journal_name_full               CrystEngComm
_journal_page_first              7249
_journal_paper_doi               10.1039/C6CE00266H
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C26 H22 N2 O4'
_chemical_formula_sum            'C26 H22 N2 O4'
_chemical_formula_weight         426.46
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-11-30 deposited with the CCDC.
2016-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 112.293(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.7362(6)
_cell_length_b                   24.2039(15)
_cell_length_c                   6.8686(5)
_cell_measurement_reflns_used    3241
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.7756
_cell_measurement_theta_min      2.5194
_cell_volume                     1036.17(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       MAR
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '132 images, ΔΦ 1.5° '
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7641
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.83
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0411
_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)+(0.0475P)²+0.3181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1073
_reflns_number_gt                1608
_reflns_number_total             1954
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce00266h4.cif
_cod_data_source_block           safin197yel
_cod_depositor_comments
'Adding full bibliography for 7224692--7224693.cif.'
_cod_original_cell_volume        1036.17(13)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7224693
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.9200(3) 1.01230(6) 1.2285(2) 0.0234(4) Uani 1 1 d .
H1 H 0.9623 1.0343 1.3521 0.028 Uiso 1 1 calc R
C2 C 0.7510(3) 0.97675(7) 1.1836(2) 0.0258(4) Uani 1 1 d .
H2 H 0.6783 0.9740 1.2777 0.031 Uiso 1 1 calc R
C3 C 0.6829(3) 0.94423(6) 1.0008(2) 0.0240(4) Uani 1 1 d .
H3 H 0.5646 0.9199 0.9717 0.029 Uiso 1 1 calc R
C4 C 0.7870(2) 0.94763(6) 0.8644(2) 0.0210(3) Uani 1 1 d .
C5 C 0.9673(2) 0.98348(6) 0.9079(2) 0.0204(3) Uani 1 1 d .
N6 N 0.7297(2) 0.91433(5) 0.6819(2) 0.0233(3) Uani 1 1 d .
C7 C 0.5323(2) 0.90724(6) 0.5613(2) 0.0225(3) Uani 1 1 d .
H7 H 0.4238 0.9248 0.5958 0.027 Uiso 1 1 calc R
C8 C 0.4702(2) 0.87325(6) 0.3740(2) 0.0211(3) Uani 1 1 d .
C9 C 0.2540(2) 0.87040(6) 0.2367(3) 0.0248(4) Uani 1 1 d .
H9 H 0.1480 0.8896 0.2701 0.030 Uiso 1 1 calc R
C10 C 0.1952(3) 0.84026(7) 0.0552(3) 0.0260(4) Uani 1 1 d .
H10 H 0.0485 0.8385 -0.0364 0.031 Uiso 1 1 calc R
C11 C 0.3502(3) 0.81189(6) 0.0032(2) 0.0240(4) Uani 1 1 d .
H11 H 0.3081 0.7909 -0.1230 0.029 Uiso 1 1 calc R
C12 C 0.5637(2) 0.81445(6) 0.1353(2) 0.0216(4) Uani 1 1 d .
C13 C 0.6265(2) 0.84487(6) 0.3230(2) 0.0207(3) Uani 1 1 d .
O14 O 0.72913(17) 0.79033(5) 0.09830(17) 0.0277(3) Uani 1 1 d .
C15 C 0.6786(3) 0.76148(7) -0.0961(3) 0.0303(4) Uani 1 1 d .
H15A H 0.5787 0.7313 -0.1043 0.046 Uiso 1 1 calc R
H15B H 0.8103 0.7463 -0.1037 0.046 Uiso 1 1 calc R
H15C H 0.6120 0.7870 -0.2135 0.046 Uiso 1 1 calc R
O16 O 0.83740(17) 0.84656(5) 0.44538(18) 0.0283(3) Uani 1 1 d .
H16 H 0.8565 0.8671 0.5496 0.042 Uiso 1 1 calc R
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
C2 C1 C5 120.43(14) . 3_777
C2 C1 H1 119.8 . .
C5 C1 H1 119.8 3_777 .
C1 C2 C3 121.11(15) . .
C1 C2 H2 119.4 . .
C3 C2 H2 119.4 . .
C4 C3 C2 120.01(15) . .
C4 C3 H3 120.0 . .
C2 C3 H3 120.0 . .
C3 C4 N6 122.23(14) . .
C3 C4 C5 120.57(14) . .
N6 C4 C5 117.13(14) . .
C1 C5 C5 119.14(17) 3_777 3_777
C1 C5 C4 122.13(14) 3_777 .
C5 C5 C4 118.72(18) 3_777 .
C7 N6 C4 121.03(13) . .
N6 C7 C8 121.87(14) . .
N6 C7 H7 119.1 . .
C8 C7 H7 119.1 . .
C9 C8 C13 119.45(14) . .
C9 C8 C7 120.03(14) . .
C13 C8 C7 120.46(13) . .
C10 C9 C8 120.42(15) . .
C10 C9 H9 119.8 . .
C8 C9 H9 119.8 . .
C9 C10 C11 120.44(15) . .
C9 C10 H10 119.8 . .
C11 C10 H10 119.8 . .
C12 C11 C10 120.05(14) . .
C12 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
O14 C12 C11 125.40(14) . .
O14 C12 C13 114.39(13) . .
C11 C12 C13 120.19(14) . .
O16 C13 C12 117.84(13) . .
O16 C13 C8 122.71(13) . .
C12 C13 C8 119.43(14) . .
C12 O14 C15 117.46(12) . .
O14 C15 H15A 109.5 . .
O14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
O14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C13 O16 H16 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.366(2) .
C1 C5 1.415(2) 3_777
C1 H1 0.9500 .
C2 C3 1.403(2) .
C2 H2 0.9500 .
C3 C4 1.370(2) .
C3 H3 0.9500 .
C4 N6 1.415(2) .
C4 C5 1.429(2) .
C5 C1 1.415(2) 3_777
C5 C5 1.418(3) 3_777
N6 C7 1.2837(19) .
C7 C8 1.449(2) .
C7 H7 0.9500 .
C8 C9 1.405(2) .
C8 C13 1.408(2) .
C9 C10 1.367(2) .
C9 H9 0.9500 .
C10 C11 1.404(2) .
C10 H10 0.9500 .
C11 C12 1.380(2) .
C11 H11 0.9500 .
C12 O14 1.3643(19) .
C12 C13 1.404(2) .
C13 O16 1.3494(18) .
O14 C15 1.4286(19) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
O16 H16 0.8400 .
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
C5 C1 C2 C3 -0.9(2) 3_777 .
C1 C2 C3 C4 0.3(2) . .
C2 C3 C4 N6 177.68(14) . .
C2 C3 C4 C5 1.0(2) . .
C3 C4 C5 C1 179.45(14) . 3_777
N6 C4 C5 C1 2.6(2) . 3_777
C3 C4 C5 C5 -1.7(2) . 3_777
N6 C4 C5 C5 -178.53(16) . 3_777
C3 C4 N6 C7 44.7(2) . .
C5 C4 N6 C7 -138.50(15) . .
C4 N6 C7 C8 -179.90(13) . .
N6 C7 C8 C9 -174.49(14) . .
N6 C7 C8 C13 2.6(2) . .
C13 C8 C9 C10 0.2(2) . .
C7 C8 C9 C10 177.29(14) . .
C8 C9 C10 C11 -0.2(2) . .
C9 C10 C11 C12 -0.2(2) . .
C10 C11 C12 O14 -177.62(15) . .
C10 C11 C12 C13 0.7(2) . .
O14 C12 C13 O16 -0.7(2) . .
C11 C12 C13 O16 -179.25(14) . .
O14 C12 C13 C8 177.73(13) . .
C11 C12 C13 C8 -0.8(2) . .
C9 C8 C13 O16 178.74(14) . .
C7 C8 C13 O16 1.6(2) . .
C9 C8 C13 C12 0.4(2) . .
C7 C8 C13 C12 -176.77(14) . .
C11 C12 O14 C15 2.1(2) . .
C13 C12 O14 C15 -176.32(13) . .
