#------------------------------------------------------------------------------
#$Date: 2016-10-08 00:52:34 +0300 (Sat, 08 Oct 2016) $
#$Revision: 187029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/46/7224692.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_7224692
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         426.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-11-30 deposited with the CCDC.
2016-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.433(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.0292(9)
_cell_length_b                   5.0669(4)
_cell_length_c                   14.7229(11)
_cell_measurement_reflns_used    4358
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.4585
_cell_measurement_theta_min      2.7989
_cell_volume                     1032.42(13)
_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_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '170 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_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2931
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.343
_diffrn_reflns_theta_min         2.805
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90840
_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            red
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0567
_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)+(0.0631P)²+1.1142P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1476
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2690
_reflns_number_total             2931
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce00266h4.cif
_cod_data_source_block           safin197red
_cod_depositor_comments
'Adding full bibliography for 7224692--7224693.cif.'
_cod_database_code               7224692
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C -0.0108(2) -0.6731(6) -0.1137(2) 0.0247(7) Uani 1 1 d . .
H1 H -0.0513 -0.7992 -0.1489 0.030 Uiso 1 1 calc R U
C2 C 0.0658(2) -0.5693(6) -0.1477(2) 0.0251(7) Uani 1 1 d . .
H2 H 0.0782 -0.6247 -0.2063 0.030 Uiso 1 1 calc R U
C3 C 0.1268(2) -0.3810(6) -0.0973(2) 0.0242(6) Uani 1 1 d . .
H3 H 0.1797 -0.3105 -0.1222 0.029 Uiso 1 1 calc R U
C4 C 0.11006(18) -0.2987(5) -0.0122(2) 0.0211(6) Uani 1 1 d . .
C5 C 0.03077(19) -0.4049(5) 0.0263(2) 0.0208(6) Uani 1 1 d . .
N6 N 0.17151(16) -0.1221(4) 0.04458(17) 0.0219(5) Uani 1 1 d . .
C7 C 0.22338(19) 0.0482(5) 0.00993(19) 0.0208(6) Uani 1 1 d . .
H7 H 0.2182 0.0602 -0.0551 0.025 Uiso 1 1 calc R U
C8 C 0.28968(18) 0.2229(5) 0.06776(19) 0.0188(6) Uani 1 1 d . .
C9 C 0.34945(19) 0.3939(5) 0.02696(19) 0.0207(6) Uani 1 1 d . .
H9 H 0.3477 0.3909 -0.0378 0.025 Uiso 1 1 calc R U
C10 C 0.41042(19) 0.5653(5) 0.0807(2) 0.0213(6) Uani 1 1 d . .
H10 H 0.4517 0.6777 0.0530 0.026 Uiso 1 1 calc R U
C11 C 0.41207(18) 0.5753(5) 0.17585(19) 0.0203(6) Uani 1 1 d . .
H11 H 0.4534 0.6972 0.2123 0.024 Uiso 1 1 calc R U
C12 C 0.35388(19) 0.4086(5) 0.21730(19) 0.0202(6) Uani 1 1 d . .
C13 C 0.29328(18) 0.2259(5) 0.16387(19) 0.0206(6) Uani 1 1 d . .
O14 O 0.35101(15) 0.4035(4) 0.31017(14) 0.0279(5) Uani 1 1 d . .
C15 C 0.4035(2) 0.6080(6) 0.3628(2) 0.0304(7) Uani 1 1 d . .
H15A H 0.4726 0.5882 0.3605 0.046 Uiso 1 1 calc R U
H15B H 0.3929 0.5965 0.4268 0.046 Uiso 1 1 calc R U
H15C H 0.3812 0.7799 0.3372 0.046 Uiso 1 1 calc R U
O16 O 0.23981(14) 0.0604(4) 0.20725(14) 0.0268(5) Uani 1 1 d . .
H16 H 0.1872 0.0286 0.1727 0.040 Uiso 1 1 calc R U
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 120.7(3) . 3_545
C2 C1 H1 119.7 . .
C5 C1 H1 119.7 3_545 .
C1 C2 C3 121.0(3) . .
C1 C2 H2 119.5 . .
C3 C2 H2 119.5 . .
C4 C3 C2 120.3(3) . .
C4 C3 H3 119.8 . .
C2 C3 H3 119.8 . .
C3 C4 N6 123.4(2) . .
C3 C4 C5 120.4(3) . .
N6 C4 C5 116.1(2) . .
C1 C5 C4 122.4(3) 3_545 .
C1 C5 C5 119.2(3) 3_545 3_545
C4 C5 C5 118.4(3) . 3_545
C7 N6 C4 121.2(2) . .
N6 C7 C8 121.7(3) . .
N6 C7 H7 119.2 . .
C8 C7 H7 119.2 . .
C9 C8 C13 119.8(3) . .
C9 C8 C7 119.6(3) . .
C13 C8 C7 120.6(2) . .
C10 C9 C8 120.1(3) . .
C10 C9 H9 119.9 . .
C8 C9 H9 119.9 . .
C9 C10 C11 120.4(3) . .
C9 C10 H10 119.8 . .
C11 C10 H10 119.8 . .
C12 C11 C10 120.4(2) . .
C12 C11 H11 119.8 . .
C10 C11 H11 119.8 . .
O14 C12 C11 124.4(2) . .
O14 C12 C13 115.5(2) . .
C11 C12 C13 120.1(2) . .
O16 C13 C12 118.3(2) . .
O16 C13 C8 122.5(2) . .
C12 C13 C8 119.2(2) . .
C12 O14 C15 115.5(2) . .
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 1.364(4) .
C1 C5 1.416(4) 3_545
C1 H1 0.9500 .
C2 C3 1.409(4) .
C2 H2 0.9500 .
C3 C4 1.377(4) .
C3 H3 0.9500 .
C4 N6 1.417(3) .
C4 C5 1.434(4) .
C5 C1 1.416(4) 3_545
C5 C5 1.434(5) 3_545
N6 C7 1.287(4) .
C7 C8 1.454(4) .
C7 H7 0.9500 .
C8 C9 1.407(4) .
C8 C13 1.408(4) .
C9 C10 1.375(4) .
C9 H9 0.9500 .
C10 C11 1.399(4) .
C10 H10 0.9500 .
C11 C12 1.384(4) .
C11 H11 0.9500 .
C12 O14 1.375(3) .
C12 C13 1.407(4) .
C13 O16 1.353(3) .
O14 C15 1.424(3) .
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 -0.3(4) 3_545 .
C1 C2 C3 C4 0.2(4) . .
C2 C3 C4 N6 176.2(3) . .
C2 C3 C4 C5 0.4(4) . .
C3 C4 C5 C1 179.8(3) . 3_545
N6 C4 C5 C1 3.8(4) . 3_545
C3 C4 C5 C5 -0.8(5) . 3_545
N6 C4 C5 C5 -176.8(3) . 3_545
C3 C4 N6 C7 27.2(4) . .
C5 C4 N6 C7 -156.9(3) . .
C4 N6 C7 C8 -177.4(2) . .
N6 C7 C8 C9 175.9(2) . .
N6 C7 C8 C13 -5.3(4) . .
C13 C8 C9 C10 -0.7(4) . .
C7 C8 C9 C10 178.1(2) . .
C8 C9 C10 C11 -1.4(4) . .
C9 C10 C11 C12 1.4(4) . .
C10 C11 C12 O14 179.7(2) . .
C10 C11 C12 C13 0.6(4) . .
O14 C12 C13 O16 -1.3(4) . .
C11 C12 C13 O16 177.9(2) . .
O14 C12 C13 C8 178.2(2) . .
C11 C12 C13 C8 -2.7(4) . .
C9 C8 C13 O16 -177.9(2) . .
C7 C8 C13 O16 3.3(4) . .
C9 C8 C13 C12 2.7(4) . .
C7 C8 C13 C12 -176.1(2) . .
C11 C12 O14 C15 7.9(4) . .
C13 C12 O14 C15 -173.0(2) . .
