#------------------------------------------------------------------------------
#$Date: 2022-09-29 04:21:32 +0300 (Thu, 29 Sep 2022) $
#$Revision: 278262 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/55/7245580.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_7245580
loop_
_publ_author_name
'Sigalov, Mark'
'Mazor, Royi'
'Ellern, Arkady'
'Larina, Nina'
'Lokshin, Vladimir'
'Khodorkovsky, Vladimir'
_publ_section_title
;
 Conjugated donor--acceptor substituted systems involving the
 1,3-indandione-derived electron accepting moieties
;
_journal_issue                   43
_journal_name_full               'RSC Advances'
_journal_page_first              27766
_journal_page_last               27774
_journal_paper_doi               10.1039/D2RA05335G
_journal_volume                  12
_journal_year                    2022
_chemical_formula_sum            'C20 H19 N O2'
_chemical_formula_weight         305.38
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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
_audit_update_record
;
2021-05-11 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                76.646(6)
_cell_angle_beta                 82.523(6)
_cell_angle_gamma                75.163(6)
_cell_formula_units_Z            2
_cell_length_a                   8.187(3)
_cell_length_b                   9.949(3)
_cell_length_c                   10.504(3)
_cell_measurement_reflns_used    1036
_cell_measurement_temperature    570(2)
_cell_measurement_theta_max      23.83
_cell_measurement_theta_min      2.63
_cell_volume                     802.4(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      570(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0563
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4083
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9974
_exptl_absorpt_correction_T_min  0.9898
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             185
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.004(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0783P)²+0.3121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1590
_refine_ls_wR_factor_ref         0.1853
_reflns_number_gt                1637
_reflns_number_total             2802
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ra05335g3.cif
_cod_data_source_block           ms2100s
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C20 H19 N1 O2'
_cod_database_code               7245580
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2849(4) 0.0160(3) 0.1790(3) 0.0461(7) Uani 1 1 d . . .
N1 N 0.1950(4) -0.2802(3) 0.5243(2) 0.0614(8) Uani 1 1 d . . .
O2 O 0.2545(3) 0.3586(3) -0.1585(2) 0.0776(8) Uani 1 1 d . . .
O1 O 0.6721(3) 0.1146(3) 0.1375(2) 0.0768(8) Uani 1 1 d . . .
C2 C 0.5276(4) 0.3896(3) -0.1261(3) 0.0493(8) Uani 1 1 d . . .
C3 C 0.6475(4) 0.3156(3) -0.0398(3) 0.0482(8) Uani 1 1 d . . .
C4 C 0.1375(4) -0.0343(3) 0.1973(3) 0.0531(8) Uani 1 1 d . . .
C5 C 0.3987(4) -0.0379(4) 0.2739(3) 0.0596(9) Uani 1 1 d . . .
C6 C 0.3820(4) 0.3214(3) -0.0993(3) 0.0510(8) Uani 1 1 d . . .
C7 C 0.3689(4) -0.1355(4) 0.3860(3) 0.0607(9) Uani 1 1 d . . .
C8 C 0.2199(4) -0.1828(3) 0.4043(3) 0.0512(8) Uani 1 1 d . . .
C9 C 0.1032(4) -0.1329(3) 0.3086(3) 0.0547(8) Uani 1 1 d . . .
C10 C 0.5887(4) 0.1969(3) 0.0511(3) 0.0498(8) Uani 1 1 d . . .
C11 C 0.5508(5) 0.5094(4) -0.2165(3) 0.0629(10) Uani 1 1 d . . .
C12 C 0.4195(4) 0.2012(3) 0.0152(3) 0.0458(7) Uani 1 1 d . . .
C13 C 0.3013(4) 0.1265(3) 0.0638(3) 0.0480(8) Uani 1 1 d . . .
C14 C 0.7977(4) 0.3581(4) -0.0415(3) 0.0618(9) Uani 1 1 d . . .
C15 C 0.6966(5) 0.5526(4) -0.2192(3) 0.0670(10) Uani 1 1 d . . .
C16 C 0.8202(5) 0.4773(4) -0.1342(4) 0.0669(10) Uani 1 1 d . . .
C17 C -0.0633(5) -0.1759(5) 0.3217(4) 0.0864(13) Uani 1 1 d . . .
H8 H -0.1298 -0.1202 0.2506 0.130 Uiso 1 1 calc R . .
H10 H -0.1237 -0.1600 0.4036 0.130 Uiso 1 1 calc R . .
H9 H -0.0420 -0.2748 0.3192 0.130 Uiso 1 1 calc R . .
C18 C 0.4978(5) -0.1911(5) 0.4871(4) 0.1028(16) Uani 1 1 d . . .
H11 H 0.5822 -0.1362 0.4671 0.154 Uiso 1 1 calc R . .
H12 H 0.5508 -0.2888 0.4861 0.154 Uiso 1 1 calc R . .
H13 H 0.4425 -0.1836 0.5724 0.154 Uiso 1 1 calc R . .
C19 C 0.1732(9) -0.4144(5) 0.5236(4) 0.133(2) Uani 1 1 d . . .
H16 H 0.2073 -0.4783 0.6043 0.199 Uiso 1 1 calc R . .
H18 H 0.2411 -0.4492 0.4512 0.199 Uiso 1 1 calc R . .
H17 H 0.0560 -0.4083 0.5150 0.199 Uiso 1 1 calc R . .
C20 C 0.1084(7) -0.2238(5) 0.6325(4) 0.129(2) Uani 1 1 d . . .
H19 H -0.0112 -0.1972 0.6222 0.193 Uiso 1 1 calc R . .
H14 H 0.1466 -0.1417 0.6372 0.193 Uiso 1 1 calc R . .
H15 H 0.1308 -0.2942 0.7117 0.193 Uiso 1 1 calc R . .
H7 H 0.045(4) 0.004(3) 0.130(3) 0.054(8) Uiso 1 1 d . . .
H5 H 0.196(4) 0.162(3) 0.013(3) 0.060(9) Uiso 1 1 d . . .
H4 H 0.892(5) 0.296(4) 0.023(4) 0.091(12) Uiso 1 1 d . . .
H3 H 0.939(5) 0.511(4) -0.129(4) 0.095(12) Uiso 1 1 d . . .
H6 H 0.493(4) -0.003(3) 0.266(3) 0.057(9) Uiso 1 1 d . . .
H1 H 0.701(4) 0.649(4) -0.279(4) 0.086(11) Uiso 1 1 d . . .
H2 H 0.474(5) 0.557(4) -0.272(4) 0.086(13) Uiso 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
_geom_angle_publ_flag
C5 C1 C4 117.6(3) . . ?
C5 C1 C13 125.3(3) . . ?
C4 C1 C13 117.0(3) . . ?
C19 N1 C20 113.7(4) . . ?
C19 N1 C8 120.8(3) . . ?
C20 N1 C8 117.9(3) . . ?
C3 C2 C11 121.1(3) . . ?
C3 C2 C6 108.8(3) . . ?
C11 C2 C6 130.1(3) . . ?
C2 C3 C14 121.1(3) . . ?
C2 C3 C10 110.6(3) . . ?
C14 C3 C10 128.3(3) . . ?
C9 C4 C1 121.9(3) . . ?
C9 C4 H7 116.8(16) . . ?
C1 C4 H7 121.2(16) . . ?
C1 C5 C7 122.2(3) . . ?
C1 C5 H6 118.9(19) . . ?
C7 C5 H6 119(2) . . ?
O2 C6 C2 126.3(3) . . ?
O2 C6 C12 126.5(3) . . ?
C2 C6 C12 107.2(2) . . ?
C5 C7 C8 119.6(3) . . ?
C5 C7 C18 120.0(3) . . ?
C8 C7 C18 120.3(3) . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 N1 116.6(3) . . ?
C9 C8 N1 123.6(3) . . ?
C4 C9 C8 118.9(3) . . ?
C4 C9 C17 117.7(3) . . ?
C8 C9 C17 123.3(3) . . ?
O1 C10 C12 129.5(3) . . ?
O1 C10 C3 123.6(3) . . ?
C12 C10 C3 106.9(2) . . ?
C15 C11 C2 118.6(3) . . ?
C15 C11 H2 120(3) . . ?
C2 C11 H2 122(3) . . ?
C13 C12 C10 134.8(3) . . ?
C13 C12 C6 118.8(3) . . ?
C10 C12 C6 106.4(2) . . ?
C12 C13 C1 134.2(3) . . ?
C12 C13 H5 112.1(17) . . ?
C1 C13 H5 113.4(17) . . ?
C16 C14 C3 117.1(3) . . ?
C16 C14 H4 123(2) . . ?
C3 C14 H4 120(2) . . ?
C11 C15 C16 120.9(3) . . ?
C11 C15 H1 116(2) . . ?
C16 C15 H1 123(2) . . ?
C15 C16 C14 121.2(3) . . ?
C15 C16 H3 124(2) . . ?
C14 C16 H3 115(2) . . ?
C9 C17 H8 109.5 . . ?
C9 C17 H10 109.5 . . ?
H8 C17 H10 109.5 . . ?
C9 C17 H9 109.5 . . ?
H8 C17 H9 109.5 . . ?
H10 C17 H9 109.5 . . ?
C7 C18 H11 109.5 . . ?
C7 C18 H12 109.5 . . ?
H11 C18 H12 109.5 . . ?
C7 C18 H13 109.5 . . ?
H11 C18 H13 109.5 . . ?
H12 C18 H13 109.5 . . ?
N1 C19 H16 109.5 . . ?
N1 C19 H18 109.5 . . ?
H16 C19 H18 109.5 . . ?
N1 C19 H17 109.5 . . ?
H16 C19 H17 109.5 . . ?
H18 C19 H17 109.5 . . ?
N1 C20 H19 109.5 . . ?
N1 C20 H14 109.5 . . ?
H19 C20 H14 109.5 . . ?
N1 C20 H15 109.5 . . ?
H19 C20 H15 109.5 . . ?
H14 C20 H15 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C5 1.374(4) . ?
C1 C4 1.396(4) . ?
C1 C13 1.452(4) . ?
N1 C19 1.394(5) . ?
N1 C20 1.411(5) . ?
N1 C8 1.427(4) . ?
O2 C6 1.216(4) . ?
O1 C10 1.222(3) . ?
C2 C3 1.371(4) . ?
C2 C11 1.380(4) . ?
C2 C6 1.483(4) . ?
C3 C14 1.396(4) . ?
C3 C10 1.479(4) . ?
C4 C9 1.391(4) . ?
C4 H7 1.04(3) . ?
C5 C7 1.381(4) . ?
C5 H6 0.91(3) . ?
C6 C12 1.488(4) . ?
C7 C8 1.392(4) . ?
C7 C18 1.506(5) . ?
C8 C9 1.395(4) . ?
C9 C17 1.510(5) . ?
C10 C12 1.470(4) . ?
C11 C15 1.363(5) . ?
C11 H2 0.88(4) . ?
C12 C13 1.347(4) . ?
C13 H5 1.02(3) . ?
C14 C16 1.386(5) . ?
C14 H4 1.07(4) . ?
C15 C16 1.386(5) . ?
C15 H1 1.03(4) . ?
C16 H3 1.12(4) . ?
C17 H8 0.9600 . ?
C17 H10 0.9600 . ?
C17 H9 0.9600 . ?
C18 H11 0.9600 . ?
C18 H12 0.9600 . ?
C18 H13 0.9600 . ?
C19 H16 0.9600 . ?
C19 H18 0.9600 . ?
C19 H17 0.9600 . ?
C20 H19 0.9600 . ?
C20 H14 0.9600 . ?
C20 H15 0.9600 . ?
