Influence of halogen size on the supramolecular and energy landscape of the THF solvates of the halogen derivatives of dianthranilide
Bieszczad, Bartosz; Pawlędzio, Sylwia; Polak, Katarzyna; Antonowicz, Jerzy; Mieczkowski, Adam; Trzybiński, Damian; CrystEngComm  (2020) –; doi:10.1039/D0CE00525H

data_7241008
_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 F2 N2 O2, C4 H8 O'
_chemical_formula_sum            'C18 H16 F2 N2 O3'
_chemical_formula_weight         346.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-03-23
_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                 90.046(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.6612(3)
_cell_length_b                   20.5090(5)
_cell_length_c                   14.3063(3)
_cell_measurement_reflns_used    11270
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.1850
_cell_measurement_theta_min      4.6590
_cell_volume                     3128.08(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_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       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0281840000
_diffrn_orient_matrix_UB_12      0.0581351000
_diffrn_orient_matrix_UB_13      -0.0648767000
_diffrn_orient_matrix_UB_21      -0.0778260000
_diffrn_orient_matrix_UB_22      0.0449174000
_diffrn_orient_matrix_UB_23      0.0638840000
_diffrn_orient_matrix_UB_31      0.1184323000
_diffrn_orient_matrix_UB_32      0.0156845000
_diffrn_orient_matrix_UB_33      0.0574975000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0228
_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       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            42020
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.062
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_min         3.767
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.993
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.471
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         5600
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0518
_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/[\s^2^(Fo^2^)+(0.0962P)^2^+1.0125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1642
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4030
_reflns_number_total             5600
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00525h2.cif
_cod_data_source_block           2018_03_27_dt_bbf2-thf_n
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7241008
_reflns_odcompleteness_completeness 99.98
_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 C(H,H,H,H,H,H) groups
2. Restrained distances
 N2A-H2A
 0.87 with sigma of 0.01
 N1A-H1A
 0.87 with sigma of 0.01
 N1B-H1B
 0.87 with sigma of 0.01
 N2B-H2B
 0.87 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C15A(H15A,H15B), C16A(H16A,H16B), C17A(H17A,H17B), C18A(H18A,H18B), C15B(H15C,
 H15D), C16B(H16C,H16D), C17B(H17C,H17D), C18B(H18C,H18D)
3.b Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C9A(H9A), C10A(H10A), C11A(H11A), C13A(H13A), C14A(H14A), C7B(H7B),
 C9B(H9B), C10B(H10B), C11B(H11B), C13B(H13B), C14B(H14B)
;
_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 1.173
_oxdiff_exptl_absorpt_empirical_full_min 0.826