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#$Date: 2020-08-06 04:30:05 +0300 (Thu, 06 Aug 2020) $
#$Revision: 254849 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/10/7241006.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_7241006
loop_
_publ_author_name
'Bieszczad, Bartosz'
'Pawlędzio, Sylwia'
'Polak, Katarzyna'
'Antonowicz, Jerzy'
'Mieczkowski, Adam'
'Trzybiński, Damian'
_publ_section_title
;
 Influence of halogen size on the supramolecular and energy landscape of
 the THF solvates of the halogen derivatives of dianthranilide
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00525H
_journal_year                    2020
_chemical_formula_moiety         'C14 H8 Cl2 N2 O2, C4 H8 O'
_chemical_formula_sum            'C18 H16 Cl2 N2 O3'
_chemical_formula_weight         379.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2020-04-06 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.6078(5)
_cell_length_b                   10.7273(4)
_cell_length_c                   31.0150(11)
_cell_measurement_reflns_used    2392
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.2210
_cell_measurement_theta_min      5.6910
_cell_volume                     3529.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0631265000
_diffrn_orient_matrix_UB_12      0.0953869000
_diffrn_orient_matrix_UB_13      -0.0301431000
_diffrn_orient_matrix_UB_21      -0.1145100000
_diffrn_orient_matrix_UB_22      -0.0871269000
_diffrn_orient_matrix_UB_23      -0.0048016000
_diffrn_orient_matrix_UB_31      -0.0628285000
_diffrn_orient_matrix_UB_32      0.0627840000
_diffrn_orient_matrix_UB_33      0.0392452000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7516
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         2.850
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.483
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.544
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       needle
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.462
_refine_diff_density_min         -0.956
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3152
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0617
_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)+(0.0916P)²+8.3758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1646
_refine_ls_wR_factor_ref         0.1764
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2558
_reflns_number_total             3152
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00525h2.cif
_cod_data_source_block           2018_01_25_dt_bbcl2thf_n
_cod_database_code               7241006
_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.
;
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C16-C17
 1.54 with sigma of 0.02
 N1-H1
 0.87 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
4. Rigid body (RIGU) restrains
 C17, C18, O3, C15, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.517
_oxdiff_exptl_absorpt_empirical_full_min 0.634
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6600(3) 0.1696(3) 0.40382(11) 0.0163(7) Uani 1 1 d . . . . .
C2 C 0.5491(3) 0.2272(3) 0.42596(10) 0.0155(7) Uani 1 1 d . . . . .
C3 C 0.5200(3) 0.3539(3) 0.42232(10) 0.0150(7) Uani 1 1 d . . . . .
C4 C 0.5909(3) 0.4311(3) 0.35180(10) 0.0154(7) Uani 1 1 d . . . . .
C5 C 0.5242(3) 0.3277(3) 0.32907(10) 0.0162(7) Uani 1 1 d . . . . .
C6 C 0.5621(3) 0.2029(3) 0.33197(10) 0.0157(7) Uani 1 1 d . . . . .
C7 C 0.4800(3) 0.1523(3) 0.45407(10) 0.0185(7) Uani 1 1 d . . . . .
H7 H 0.4986 0.0680 0.4567 0.022 Uiso 1 1 calc R . . . .
C8 C 0.3837(3) 0.2045(3) 0.47793(11) 0.0191(7) Uani 1 1 d . . . . .
C9 C 0.3562(4) 0.3303(3) 0.47600(11) 0.0217(8) Uani 1 1 d . . . . .
H9 H 0.2931 0.3643 0.4932 0.026 Uiso 1 1 calc R . . . .
C10 C 0.4250(3) 0.4052(3) 0.44782(11) 0.0194(7) Uani 1 1 d . . . . .
H10 H 0.4074 0.4900 0.4460 0.023 Uiso 1 1 calc R . . . .
C11 C 0.4334(3) 0.3618(3) 0.29860(11) 0.0191(7) Uani 1 1 d . . . . .
H11 H 0.4073 0.4443 0.2964 0.023 Uiso 1 1 calc R . . . .
C12 C 0.3826(3) 0.2720(4) 0.27171(11) 0.0221(8) Uani 1 1 d . . . . .
C13 C 0.4213(4) 0.1488(4) 0.27378(11) 0.0253(8) Uani 1 1 d . . . . .
H13 H 0.3873 0.0895 0.2552 0.030 Uiso 1 1 calc R . . . .
C14 C 0.5116(3) 0.1153(3) 0.30398(11) 0.0212(7) Uani 1 1 d . . . . .
H14 H 0.5386 0.0329 0.3055 0.025 Uiso 1 1 calc R . . . .
Cl1 Cl 0.29840(9) 0.10905(8) 0.51269(3) 0.0262(3) Uani 1 1 d . . . . .
Cl2 Cl 0.27108(10) 0.31894(10) 0.23425(3) 0.0355(3) Uani 1 1 d . . . . .
N1 N 0.5925(3) 0.4333(3) 0.39502(9) 0.0162(6) Uani 1 1 d D . . . .
H1 H 0.634(3) 0.491(3) 0.4081(11) 0.019 Uiso 1 1 d DR . . . .
N2 N 0.6613(3) 0.1664(3) 0.36006(9) 0.0164(6) Uani 1 1 d . . . . .
H2 H 0.722(4) 0.123(4) 0.3481(14) 0.021(11) Uiso 1 1 d . . . . .
O1 O 0.7441(2) 0.1221(2) 0.42554(7) 0.0180(5) Uani 1 1 d . . . . .
O2 O 0.6425(2) 0.5126(2) 0.32965(7) 0.0202(5) Uani 1 1 d . . . . .
C15 C 0.0489(5) 0.2692(5) 0.41827(18) 0.0511(11) Uani 1 1 d . U . . .
H15A H 0.0869 0.3287 0.4379 0.061 Uiso 1 1 calc R . . . .
H15B H -0.0229 0.2313 0.4325 0.061 Uiso 1 1 calc R . . . .
C16 C 0.0081(7) 0.3328(6) 0.37817(18) 0.0665(16) Uani 1 1 d D U . . .
H16A H -0.0790 0.3126 0.3716 0.080 Uiso 1 1 calc R . . . .
H16B H 0.0156 0.4225 0.3812 0.080 Uiso 1 1 calc R . . . .
C17 C 0.0911(7) 0.2875(7) 0.3444(2) 0.0779(15) Uani 1 1 d D U . . .
H17A H 0.1317 0.3566 0.3297 0.093 Uiso 1 1 calc R . . . .
H17B H 0.0442 0.2392 0.3234 0.093 Uiso 1 1 calc R . . . .
C18 C 0.1869(6) 0.2077(6) 0.3667(2) 0.0637(14) Uani 1 1 d . U . . .
H18A H 0.2030 0.1327 0.3502 0.076 Uiso 1 1 calc R . . . .
H18B H 0.2655 0.2527 0.3701 0.076 Uiso 1 1 calc R . . . .
O3 O 0.1368(4) 0.1777(4) 0.40665(14) 0.0622(10) Uani 1 1 d . U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cl Cl 0.3639 0.7018 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C2 118.5(3) . . ?
O1 C1 C2 119.4(3) . . ?
O1 C1 N2 122.0(3) . . ?
C3 C2 C1 122.6(3) . . ?
C7 C2 C1 117.6(3) . . ?
C7 C2 C3 119.6(3) . . ?
C2 C3 N1 120.6(3) . . ?
C10 C3 C2 119.9(3) . . ?
C10 C3 N1 119.4(3) . . ?
N1 C4 C5 119.4(3) . . ?
O2 C4 C5 118.1(3) . . ?
O2 C4 N1 122.4(3) . . ?
C6 C5 C4 123.0(3) . . ?
C11 C5 C4 116.9(3) . . ?
C11 C5 C6 119.4(3) . . ?
C5 C6 N2 121.0(3) . . ?
C14 C6 C5 119.8(3) . . ?
C14 C6 N2 118.9(3) . . ?
C2 C7 H7 120.3 . . ?
C8 C7 C2 119.5(3) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C9 121.9(3) . . ?
C7 C8 Cl1 118.6(3) . . ?
C9 C8 Cl1 119.4(3) . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.7(3) . . ?
C10 C9 H9 120.6 . . ?
C3 C10 H10 119.8 . . ?
C9 C10 C3 120.4(3) . . ?
C9 C10 H10 119.8 . . ?
C5 C11 H11 120.2 . . ?
C12 C11 C5 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 121.4(3) . . ?
C11 C12 Cl2 117.9(3) . . ?
C13 C12 Cl2 120.7(3) . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C14 118.9(3) . . ?
C14 C13 H13 120.6 . . ?
C6 C14 C13 120.9(3) . . ?
C6 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C3 N1 H1 115(3) . . ?
C4 N1 C3 125.2(3) . . ?
C4 N1 H1 119(3) . . ?
C1 N2 C6 126.7(3) . . ?
C1 N2 H2 116(3) . . ?
C6 N2 H2 116(3) . . ?
H15A C15 H15B 108.5 . . ?
C16 C15 H15A 110.2 . . ?
C16 C15 H15B 110.2 . . ?
O3 C15 H15A 110.2 . . ?
O3 C15 H15B 110.2 . . ?
O3 C15 C16 107.5(5) . . ?
C15 C16 H16A 110.5 . . ?
C15 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
C17 C16 C15 105.9(5) . . ?
C17 C16 H16A 110.5 . . ?
C17 C16 H16B 110.5 . . ?
C16 C17 H17A 110.6 . . ?
C16 C17 H17B 110.6 . . ?
C16 C17 C18 105.5(5) . . ?
H17A C17 H17B 108.8 . . ?
C18 C17 H17A 110.6 . . ?
C18 C17 H17B 110.6 . . ?
C17 C18 H18A 110.4 . . ?
C17 C18 H18B 110.4 . . ?
H18A C18 H18B 108.6 . . ?
O3 C18 C17 106.6(5) . . ?
O3 C18 H18A 110.4 . . ?
O3 C18 H18B 110.4 . . ?
C18 O3 C15 108.8(4) . . ?
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 C2 1.495(5) . ?
C1 N2 1.358(4) . ?
C1 O1 1.229(4) . ?
C2 C3 1.399(5) . ?
C2 C7 1.394(5) . ?
C3 C10 1.394(5) . ?
C3 N1 1.427(4) . ?
C4 C5 1.493(4) . ?
C4 N1 1.341(4) . ?
C4 O2 1.239(4) . ?
C5 C6 1.402(5) . ?
C5 C11 1.398(5) . ?
C6 C14 1.387(5) . ?
C6 N2 1.421(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.380(5) . ?
C8 C9 1.382(5) . ?
C8 Cl1 1.740(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.394(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.384(5) . ?
C12 C13 1.385(5) . ?
C12 Cl2 1.733(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(5) . ?
C14 H14 0.9300 . ?
N1 H1 0.867(10) . ?
N2 H2 0.88(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.483(7) . ?
C15 O3 1.401(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.453(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.499(9) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 O3 1.385(7) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C10 -172.1(3) . . . . ?
C1 C2 C3 N1 3.3(5) . . . . ?
C1 C2 C7 C8 174.5(3) . . . . ?
C2 C1 N2 C6 -5.9(5) . . . . ?
C2 C3 C10 C9 -2.0(5) . . . . ?
C2 C3 N1 C4 71.2(4) . . . . ?
C2 C7 C8 C9 -2.3(5) . . . . ?
C2 C7 C8 Cl1 179.8(3) . . . . ?
C3 C2 C7 C8 0.0(5) . . . . ?
C4 C5 C6 C14 -167.9(3) . . . . ?
C4 C5 C6 N2 5.4(5) . . . . ?
C4 C5 C11 C12 169.9(3) . . . . ?
C5 C4 N1 C3 -9.5(5) . . . . ?
C5 C6 C14 C13 -1.7(5) . . . . ?
C5 C6 N2 C1 66.8(5) . . . . ?
C5 C11 C12 C13 -1.1(5) . . . . ?
C5 C11 C12 Cl2 -179.6(3) . . . . ?
C6 C5 C11 C12 -0.2(5) . . . . ?
C7 C2 C3 C10 2.1(5) . . . . ?
C7 C2 C3 N1 177.6(3) . . . . ?
C7 C8 C9 C10 2.5(6) . . . . ?
C8 C9 C10 C3 -0.3(5) . . . . ?
C10 C3 N1 C4 -113.3(4) . . . . ?
C11 C5 C6 C14 1.6(5) . . . . ?
C11 C5 C6 N2 174.8(3) . . . . ?
C11 C12 C13 C14 1.0(6) . . . . ?
C12 C13 C14 C6 0.5(5) . . . . ?
C14 C6 N2 C1 -119.9(4) . . . . ?
Cl1 C8 C9 C10 -179.7(3) . . . . ?
Cl2 C12 C13 C14 179.4(3) . . . . ?
N1 C3 C10 C9 -177.5(3) . . . . ?
N1 C4 C5 C6 -64.2(5) . . . . ?
N1 C4 C5 C11 126.1(3) . . . . ?
N2 C1 C2 C3 -65.2(4) . . . . ?
N2 C1 C2 C7 120.5(3) . . . . ?
N2 C6 C14 C13 -175.1(3) . . . . ?
O1 C1 C2 C3 117.9(4) . . . . ?
O1 C1 C2 C7 -56.4(4) . . . . ?
O1 C1 N2 C6 170.9(3) . . . . ?
O2 C4 C5 C6 116.2(4) . . . . ?
O2 C4 C5 C11 -53.5(4) . . . . ?
O2 C4 N1 C3 170.1(3) . . . . ?
C15 C16 C17 C18 -5.4(8) . . . . ?
C16 C15 O3 C18 21.2(7) . . . . ?
C16 C17 C18 O3 18.2(8) . . . . ?
C17 C18 O3 C15 -24.6(7) . . . . ?
O3 C15 C16 C17 -9.0(7) . . . . ?
