#------------------------------------------------------------------------------
#$Date: 2023-12-07 13:51:13 +0200 (Thu, 07 Dec 2023) $
#$Revision: 288146 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/29/2022919.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_2022919
loop_
_publ_author_name
'Rharmili, Nohaila'
'Abdellaoui, Omar'
'Haoudi, Amal'
'Mague, Joel T.'
'Hökelek, Tuncer'
'Ouazzani Chahdi, Fouad'
'Kandri Rodi, Youssef'
'Mazzah, Ahmed'
'Sebbar, Nada Kheira'
_publ_section_title
;
 Synthesis, crystal structure and Hirshfeld surface analysis of
 1-(12-bromo-dodec-yl)indoline-2,3-dione.
;
_journal_coeditor_code           HB8077
_journal_issue                   'Pt 11'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1033
_journal_page_last               1036
_journal_paper_doi               10.1107/S2056989023009052
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C20 H28 Br N O2'
_chemical_formula_moiety         'C20 H28 Br N O2'
_chemical_formula_sum            'C20 H28 Br N O2'
_chemical_formula_weight         394.34
_chemical_name_systematic
;
1-(12-Bromododecyl)indoline-2,3-dione
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_cell_angle_alpha                90
_cell_angle_beta                 105.2310(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.5385(5)
_cell_length_b                   8.1977(2)
_cell_length_c                   12.3185(3)
_cell_measurement_reflns_used    9620
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      74.6592
_cell_measurement_theta_min      6.6070
_cell_volume                     2001.19(8)
_computing_cell_refinement
;
SAINT (Bruker, 2021)
;
_computing_data_collection
;
APEX4 (Bruker, 2021)
;
_computing_data_reduction
;
SAINT (Bruker, 2021)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2019/1 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Bruker D8 VENTURE PHOTON 3 CPAD'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 3 CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            42466
_diffrn_reflns_theta_full        74.700
_diffrn_reflns_theta_max         74.717
_diffrn_reflns_theta_min         5.841
_diffrn_source                   'INCOATEC I\mS micro----focus source'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.878
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.660
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0459P)²+0.8387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0839
_reflns_number_gt                3810
_reflns_number_total             4091
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8077sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2022919.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022919
_cod_database_fobs_code          2022919
_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.
;
_shelx_estimated_absorpt_t_min   0.560
_shelx_estimated_absorpt_t_max   0.874
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_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.23573(2) 0.63104(3) -0.09416(2) 0.04517(9) Uani d 1 . .
O O1 0.94289(6) 0.56654(16) 1.23349(9) 0.0368(3) Uani d 1 . .
O O2 0.85863(7) 0.82935(15) 1.10434(10) 0.0389(3) Uani d 1 . .
N N1 0.86491(7) 0.66570(16) 0.95494(10) 0.0284(3) Uani d 1 . .
C C1 0.89366(8) 0.51288(19) 0.94215(12) 0.0279(3) Uani d 1 . .
C C2 0.89087(9) 0.4326(2) 0.84263(13) 0.0342(3) Uani d 1 . .
H H2 0.868176 0.478183 0.771913 0.041 Uiso calc 1 . .
C C3 0.92292(10) 0.2814(2) 0.85063(15) 0.0408(4) Uani d 1 . .
H H3 0.921145 0.221844 0.783763 0.049 Uiso calc 1 . .
C C4 0.95722(11) 0.2157(2) 0.95316(17) 0.0441(4) Uani d 1 . .
H H4 0.978553 0.112444 0.955471 0.053 Uiso calc 1 . .
C C5 0.96083(9) 0.2996(2) 1.05346(15) 0.0381(4) Uani d 1 . .
H H5 0.984786 0.255493 1.123970 0.046 Uiso calc 1 . .
C C6 0.92842(8) 0.44880(19) 1.04685(12) 0.0291(3) Uani d 1 . .
C C7 0.92153(8) 0.5672(2) 1.13243(12) 0.0295(3) Uani d 1 . .
C C8 0.87763(8) 0.70783(19) 1.06527(12) 0.0288(3) Uani d 1 . .
C C9 0.82336(8) 0.75912(19) 0.86123(13) 0.0305(3) Uani d 1 . .
H H9A 0.846127 0.762987 0.799706 0.037 Uiso calc 1 . .
H H9B 0.819151 0.872468 0.886282 0.037 Uiso calc 1 . .
C C10 0.75317(8) 0.6868(2) 0.81630(13) 0.0331(3) Uani d 1 . .
H H10A 0.727660 0.697533 0.873860 0.040 Uiso calc 1 . .
H H10B 0.756986 0.569283 0.800587 0.040 Uiso calc 1 . .
C C11 0.71523(8) 0.7737(2) 0.70892(13) 0.0341(3) Uani d 1 . .
H H11A 0.711684 0.890940 0.725920 0.041 Uiso calc 1 . .
H H11B 0.741989 0.765068 0.653024 0.041 Uiso calc 1 . .
C C12 0.64480(9) 0.7080(2) 0.65650(15) 0.0368(4) Uani d 1 . .
H H12A 0.616860 0.722365 0.710190 0.044 Uiso calc 1 . .
H H12B 0.647686 0.589718 0.642263 0.044 Uiso calc 1 . .
C C13 0.61065(9) 0.7937(2) 0.54628(15) 0.0383(4) Uani d 1 . .
H H13A 0.607081 0.911480 0.561449 0.046 Uiso calc 1 . .
H H13B 0.639655 0.782183 0.494000 0.046 Uiso calc 1 . .
C C14 0.54078(9) 0.7290(2) 0.48892(16) 0.0417(4) Uani d 1 . .
H H14A 0.511876 0.738333 0.541513 0.050 Uiso calc 1 . .
H H14B 0.544331 0.611842 0.471812 0.050 Uiso calc 1 . .
C C15 0.50706(9) 0.8189(3) 0.38039(15) 0.0409(4) Uani d 1 . .
H H15A 0.502037 0.935261 0.398112 0.049 Uiso calc 1 . .
H H15B 0.536913 0.813268 0.329128 0.049 Uiso calc 1 . .
C C16 0.43816(10) 0.7513(3) 0.31976(16) 0.0441(4) Uani d 1 . .
H H16A 0.409126 0.750231 0.372436 0.053 Uiso calc 1 . .
H H16B 0.443516 0.637118 0.297345 0.053 Uiso calc 1 . .
C C17 0.40299(9) 0.8494(2) 0.21510(16) 0.0407(4) Uani d 1 . .
H H17A 0.396679 0.962919 0.237824 0.049 Uiso calc 1 . .
H H17B 0.432541 0.852711 0.163291 0.049 Uiso calc 1 . .
C C18 0.33462(9) 0.7797(2) 0.15255(15) 0.0401(4) Uani d 1 . .
H H18A 0.341349 0.670770 0.122508 0.048 Uiso calc 1 . .
H H18B 0.306601 0.765498 0.206143 0.048 Uiso calc 1 . .
C C19 0.29721(10) 0.8881(2) 0.05611(17) 0.0414(4) Uani d 1 . .
H H19A 0.292143 0.998012 0.086216 0.050 Uiso calc 1 . .
H H19B 0.324937 0.899538 0.001841 0.050 Uiso calc 1 . .
C C20 0.22811(10) 0.8256(2) -0.00592(17) 0.0439(4) Uani d 1 . .
H H20A 0.203421 0.911798 -0.056606 0.053 Uiso calc 1 . .
H H20B 0.202084 0.798731 0.048907 0.053 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C8 N1 C1 . . 111.16(12) ?
C8 N1 C9 . . 125.20(13) ?
C1 N1 C9 . . 123.53(13) ?
C2 C1 C6 . . 122.08(14) ?
C2 C1 N1 . . 127.01(14) ?
C6 C1 N1 . . 110.90(13) ?
C1 C2 C3 . . 116.91(15) ?
C1 C2 H2 . . 121.5 ?
C3 C2 H2 . . 121.5 ?
C4 C3 C2 . . 121.89(16) ?
C4 C3 H3 . . 119.1 ?
C2 C3 H3 . . 119.1 ?
C3 C4 C5 . . 120.73(16) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C6 C5 C4 . . 117.98(16) ?
C6 C5 H5 . . 121.0 ?
C4 C5 H5 . . 121.0 ?
C5 C6 C1 . . 120.39(14) ?
C5 C6 C7 . . 132.69(15) ?
C1 C6 C7 . . 106.93(13) ?
O1 C7 C6 . . 131.37(15) ?
O1 C7 C8 . . 123.61(15) ?
C6 C7 C8 . . 105.03(12) ?
O2 C8 N1 . . 127.38(15) ?
O2 C8 C7 . . 126.65(14) ?
N1 C8 C7 . . 105.96(12) ?
N1 C9 C10 . . 112.60(13) ?
N1 C9 H9A . . 109.1 ?
C10 C9 H9A . . 109.1 ?
N1 C9 H9B . . 109.1 ?
C10 C9 H9B . . 109.1 ?
H9A C9 H9B . . 107.8 ?
C9 C10 C11 . . 110.67(13) ?
C9 C10 H10A . . 109.5 ?
C11 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
C11 C10 H10B . . 109.5 ?
H10A C10 H10B . . 108.1 ?
C12 C11 C10 . . 114.56(14) ?
C12 C11 H11A . . 108.6 ?
C10 C11 H11A . . 108.6 ?
C12 C11 H11B . . 108.6 ?
C10 C11 H11B . . 108.6 ?
H11A C11 H11B . . 107.6 ?
C11 C12 C13 . . 112.25(14) ?
C11 C12 H12A . . 109.2 ?
C13 C12 H12A . . 109.2 ?
C11 C12 H12B . . 109.2 ?
C13 C12 H12B . . 109.2 ?
H12A C12 H12B . . 107.9 ?
C14 C13 C12 . . 114.24(15) ?
C14 C13 H13A . . 108.7 ?
C12 C13 H13A . . 108.7 ?
C14 C13 H13B . . 108.7 ?
C12 C13 H13B . . 108.7 ?
H13A C13 H13B . . 107.6 ?
C13 C14 C15 . . 113.28(16) ?
C13 C14 H14A . . 108.9 ?
C15 C14 H14A . . 108.9 ?
C13 C14 H14B . . 108.9 ?
C15 C14 H14B . . 108.9 ?
H14A C14 H14B . . 107.7 ?
C16 C15 C14 . . 113.84(16) ?
C16 C15 H15A . . 108.8 ?
C14 C15 H15A . . 108.8 ?
C16 C15 H15B . . 108.8 ?
C14 C15 H15B . . 108.8 ?
H15A C15 H15B . . 107.7 ?
C15 C16 C17 . . 113.24(16) ?
C15 C16 H16A . . 108.9 ?
C17 C16 H16A . . 108.9 ?
C15 C16 H16B . . 108.9 ?
C17 C16 H16B . . 108.9 ?
H16A C16 H16B . . 107.7 ?
C18 C17 C16 . . 113.39(16) ?
C18 C17 H17A . . 108.9 ?
C16 C17 H17A . . 108.9 ?
C18 C17 H17B . . 108.9 ?
C16 C17 H17B . . 108.9 ?
H17A C17 H17B . . 107.7 ?
C19 C18 C17 . . 112.64(16) ?
C19 C18 H18A . . 109.1 ?
C17 C18 H18A . . 109.1 ?
C19 C18 H18B . . 109.1 ?
C17 C18 H18B . . 109.1 ?
H18A C18 H18B . . 107.8 ?
C20 C19 C18 . . 114.25(16) ?
C20 C19 H19A . . 108.7 ?
C18 C19 H19A . . 108.7 ?
C20 C19 H19B . . 108.7 ?
C18 C19 H19B . . 108.7 ?
H19A C19 H19B . . 107.6 ?
C19 C20 Br1 . . 110.79(13) ?
C19 C20 H20A . . 109.5 ?
Br1 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
Br1 C20 H20B . . 109.5 ?
H20A C20 H20B . . 108.1 ?
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
Br1 C20 . 1.9593(18) ?
O1 C7 . 1.2064(19) ?
O2 C8 . 1.214(2) ?
N1 C8 . 1.3595(19) ?
N1 C1 . 1.4113(19) ?
N1 C9 . 1.4593(19) ?
C1 C2 . 1.379(2) ?
C1 C6 . 1.402(2) ?
C2 C3 . 1.395(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.384(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.399(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.385(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.467(2) ?
C7 C8 . 1.560(2) ?
C9 C10 . 1.522(2) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.524(2) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.519(2) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.526(2) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.519(2) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.524(3) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.521(3) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 C17 . 1.530(3) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 C18 . 1.524(2) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 C19 . 1.521(3) ?
C18 H18A . 0.9900 ?
C18 H18B . 0.9900 ?
C19 C20 . 1.514(3) ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
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
C2 H2 O2 4_575 0.95 2.56 3.441(2) 154 yes
C3 H3 O1 4_565 0.95 2.51 3.271(2) 137 y
C5 H5 O1 2_747 0.95 2.51 3.424(2) 160 y
C9 H9A O2 4_575 0.99 2.60 3.503(2) 152 yes
C20 H20A O2 3_676 0.99 2.47 3.393(2) 156 yes
C20 H20B Cg2 3_666 0.99 2.96 3.756(2) 139 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
C8 N1 C1 C2 . . . . -179.95(16) ?
C9 N1 C1 C2 . . . . 3.8(3) ?
C8 N1 C1 C6 . . . . -1.14(19) ?
C9 N1 C1 C6 . . . . -177.41(14) ?
C6 C1 C2 C3 . . . . 1.6(3) ?
N1 C1 C2 C3 . . . . -179.68(16) ?
C1 C2 C3 C4 . . . . -1.3(3) ?
C2 C3 C4 C5 . . . . 0.1(3) ?
C3 C4 C5 C6 . . . . 0.8(3) ?
C4 C5 C6 C1 . . . . -0.5(3) ?
C4 C5 C6 C7 . . . . 179.77(18) ?
C2 C1 C6 C5 . . . . -0.8(3) ?
N1 C1 C6 C5 . . . . -179.66(15) ?
C2 C1 C6 C7 . . . . 179.05(15) ?
N1 C1 C6 C7 . . . . 0.16(18) ?
C5 C6 C7 O1 . . . . 0.3(3) ?
C1 C6 C7 O1 . . . . -179.48(17) ?
C5 C6 C7 C8 . . . . -179.49(18) ?
C1 C6 C7 C8 . . . . 0.71(16) ?
C1 N1 C8 O2 . . . . -178.14(16) ?
C9 N1 C8 O2 . . . . -1.9(3) ?
C1 N1 C8 C7 . . . . 1.52(17) ?
C9 N1 C8 C7 . . . . 177.72(14) ?
O1 C7 C8 O2 . . . . -1.5(3) ?
C6 C7 C8 O2 . . . . 178.29(16) ?
O1 C7 C8 N1 . . . . 178.80(15) ?
C6 C7 C8 N1 . . . . -1.37(16) ?
C8 N1 C9 C10 . . . . -101.92(18) ?
C1 N1 C9 C10 . . . . 73.83(19) ?
N1 C9 C10 C11 . . . . -172.10(13) ?
C9 C10 C11 C12 . . . . 179.03(14) ?
C10 C11 C12 C13 . . . . -177.09(15) ?
C11 C12 C13 C14 . . . . 178.41(15) ?
C12 C13 C14 C15 . . . . 178.72(16) ?
C13 C14 C15 C16 . . . . 177.83(17) ?
C14 C15 C16 C17 . . . . 176.30(16) ?
C15 C16 C17 C18 . . . . 178.65(16) ?
C16 C17 C18 C19 . . . . 174.02(16) ?
C17 C18 C19 C20 . . . . -178.23(16) ?
C18 C19 C20 Br1 . . . . -70.41(19) ?
