#------------------------------------------------------------------------------
#$Date: 2020-06-05 12:49:43 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252702 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/63/7126382.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_7126382
loop_
_publ_author_name
'O'Malley, Ciarán'
'Erxleben, Andrea'
'Kellehan, Seamus'
'McArdle, Patrick'
_publ_section_title
;
 Unprecedented morphology control of gas phase cocrystal growth using
 multi zone heating and tailor made additives.
;
_journal_issue                   42
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5657
_journal_page_last               5660
_journal_paper_doi               10.1039/d0cc01067g
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C36 H24 F4 N2 O6'
_chemical_formula_weight         656.57
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-04-07 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.309(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.7762(4)
_cell_length_b                   29.2094(16)
_cell_length_c                   13.5261(9)
_cell_measurement_reflns_used    1088
_cell_measurement_temperature    299.0(1)
_cell_measurement_theta_max      27.5140
_cell_measurement_theta_min      4.4390
_cell_volume                     1482.9(2)
_computing_cell_refinement       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_data_collection       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_data_reduction        'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_molecular_graphics
'ORTEX - P. McArdle, J.Appl.Cryst.,1995,28,65-65.'
_computing_publication_material
'Oscail - P. McArdle, J.Appl.Cryst.,2017,50,320-326.'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      299.0(1)
_diffrn_detector_area_resol_mean 16.1048
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_device_type  'xcalibur, sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6756
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.151
_diffrn_reflns_theta_min         3.683
_diffrn_source                   'fine-focus sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
crysalispro 1.171.40.14e (rigaku oxford diffraction, 2018) 
empirical absorption correction using spherical harmonics, 
 implemented in scale3 abspack scaling algorithm. 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3407
_refine_ls_number_restraints     68
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0521
_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)+(0.0449P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1933
_reflns_number_total             3407
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc01067g5.cif
_cod_data_source_block           dif_bipy
_cod_depositor_comments
'Adding full bibliography for 7126379--7126382.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7126382
_shelx_shelxl_version_number     2018/3
_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   0.944
_shelx_estimated_absorpt_t_max   0.977
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, 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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.7735(5) 0.03556(4) 0.37811(10) 0.0867(5) Uani 1 1 d . . . . .
F2 F 0.7428(4) 0.08186(4) 0.70701(9) 0.0673(4) Uani 1 1 d . . . . .
O1 O 1.0562(5) 0.27889(5) 0.87443(11) 0.0682(5) Uani 1 1 d D . . . .
O2 O 0.7461(5) 0.33148(5) 0.73720(11) 0.0729(5) Uani 1 1 d . . . . .
O3 O 0.5548(5) 0.30237(5) 0.58953(11) 0.0616(5) Uani 1 1 d D . . . .
N1 N 0.352(3) 0.3887(4) 0.5494(9) 0.044(2) Uani 0.5 1 d D U P A 1
C1 C 0.8273(7) 0.06858(6) 0.44901(16) 0.0538(6) Uani 1 1 d . . . . .
C2 C 0.9397(6) 0.11082(7) 0.42256(15) 0.0514(6) Uani 1 1 d . . . . .
H2 H 0.983195 0.116997 0.357535 0.067 Uiso 1 1 calc R U . . .
C3 C 0.9868(6) 0.14395(6) 0.49504(14) 0.0430(5) Uani 1 1 d . . . . .
H3A H 1.065261 0.172750 0.477840 0.056 Uiso 1 1 calc R U . . .
C4 C 0.9221(5) 0.13629(6) 0.59297(13) 0.0373(5) Uani 1 1 d . . . . .
C5 C 0.8143(6) 0.09223(6) 0.61300(14) 0.0450(5) Uani 1 1 d . . . . .
C6 C 0.7640(6) 0.05808(6) 0.54386(16) 0.0528(6) Uani 1 1 d . . . . .
H6 H 0.690142 0.028994 0.560637 0.069 Uiso 1 1 calc R U . . .
C7 C 0.9549(5) 0.17370(6) 0.66731(13) 0.0371(5) Uani 1 1 d . . . . .
C8 C 0.8265(5) 0.21691(6) 0.64092(14) 0.0394(5) Uani 1 1 d . . . . .
H8 H 0.718055 0.221835 0.576696 0.051 Uiso 1 1 calc R U . . .
C9 C 0.8556(5) 0.25311(6) 0.70804(13) 0.0402(5) Uani 1 1 d . . . . .
C10 C 1.0183(6) 0.24553(6) 0.80477(14) 0.0456(5) Uani 1 1 d . . . . .
C11 C 1.1506(6) 0.20251(7) 0.83149(15) 0.0477(5) Uani 1 1 d . . . . .
H11 H 1.261682 0.197488 0.895389 0.062 Uiso 1 1 calc R U . . .
C12 C 1.1183(6) 0.16738(6) 0.76419(14) 0.0440(5) Uani 1 1 d . . . . .
H12 H 1.207006 0.138639 0.783341 0.057 Uiso 1 1 calc R U . . .
C13 C 0.7158(6) 0.29879(7) 0.68007(16) 0.0497(6) Uani 1 1 d . . . . .
C14 C 0.3866(15) 0.42072(15) 0.6201(4) 0.0510(13) Uani 0.5 1 d D . P A 1
H14 H 0.494298 0.412799 0.682942 0.061 Uiso 0.5 1 calc R U P A 1
C15 C 0.2692(15) 0.46500(15) 0.6041(3) 0.0505(13) Uani 0.5 1 d D . P A 1
H15 H 0.290908 0.485842 0.656382 0.061 Uiso 0.5 1 calc R U P A 1
C16 C 0.120(2) 0.4787(3) 0.5115(6) 0.0303(17) Uani 0.5 1 d D . P A 1
C17 C 0.137(5) 0.4474(5) 0.4376(10) 0.033(3) Uani 0.5 1 d D U P A 1
H17 H 0.090703 0.456239 0.371379 0.040 Uiso 0.5 1 calc R U P A 1
C18 C 0.224(8) 0.4024(6) 0.4608(10) 0.048(2) Uani 0.5 1 d D U P A 1
H18 H 0.188457 0.380645 0.410486 0.057 Uiso 0.5 1 calc R U P A 1
H1 H 0.964(7) 0.3037(7) 0.8414(17) 0.091(9) Uiso 1 1 d D . . . .
H3 H 0.487(8) 0.3326(6) 0.578(2) 0.122(11) Uiso 1 1 d D . . . .
N1A N 0.242(3) 0.3841(4) 0.5499(9) 0.050(3) Uani 0.5 1 d D U P B 2
C14A C 0.1469(15) 0.41142(16) 0.6199(4) 0.0525(13) Uani 0.5 1 d D . P B 2
H14A H 0.159181 0.399866 0.684282 0.063 Uiso 0.5 1 calc R U P B 2
C15A C 0.0314(15) 0.45564(15) 0.6048(3) 0.0476(12) Uani 0.5 1 d D . P B 2
H15A H -0.026277 0.473370 0.657869 0.057 Uiso 0.5 1 calc R U P B 2
C16A C 0.002(2) 0.4734(3) 0.5099(7) 0.0323(18) Uani 0.5 1 d D . P B 2
C17A C 0.054(5) 0.4433(5) 0.4362(10) 0.032(3) Uani 0.5 1 d D U P B 2
H17A H -0.010432 0.451369 0.370173 0.039 Uiso 0.5 1 calc R U P B 2
C18A C 0.203(8) 0.4007(6) 0.4585(10) 0.044(2) Uani 0.5 1 d D U P B 2
H18A H 0.277431 0.383111 0.407372 0.053 Uiso 0.5 1 calc R U P B 2
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'
F F 0.0171 0.0103 '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
C10 O1 H1 103.2(16) . . ?
C13 O3 H3 109.0(18) . . ?
C18 N1 C14 116.1(10) . . ?
F1 C1 C2 118.89(19) . . ?
F1 C1 C6 118.37(18) . . ?
C2 C1 C6 122.74(19) . . ?
C1 C2 C3 117.95(19) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C2 C3 C4 122.90(17) . . ?
C2 C3 H3A 118.5 . . ?
C4 C3 H3A 118.5 . . ?
C5 C4 C3 114.95(17) . . ?
C5 C4 C7 123.85(17) . . ?
C3 C4 C7 121.16(16) . . ?
F2 C5 C6 116.73(17) . . ?
F2 C5 C4 118.78(17) . . ?
C6 C5 C4 124.47(19) . . ?
C1 C6 C5 116.97(18) . . ?
C1 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
C8 C7 C12 117.89(17) . . ?
C8 C7 C4 119.79(17) . . ?
C12 C7 C4 122.31(16) . . ?
C7 C8 C9 121.65(18) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C10 119.00(17) . . ?
C8 C9 C13 121.49(17) . . ?
C10 C9 C13 119.50(17) . . ?
O1 C10 C11 117.67(19) . . ?
O1 C10 C9 122.62(17) . . ?
C11 C10 C9 119.71(17) . . ?
C12 C11 C10 120.23(18) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 121.50(18) . . ?
C11 C12 H12 119.2 . . ?
C7 C12 H12 119.2 . . ?
O2 C13 O3 121.90(19) . . ?
O2 C13 C9 122.6(2) . . ?
O3 C13 C9 115.47(17) . . ?
N1 C14 C15 122.8(6) . . ?
N1 C14 H14 118.6 . . ?
C15 C14 H14 118.6 . . ?
C16 C15 C14 120.6(6) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 115.2(9) . . ?
C16 C17 C18 120.0(11) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
N1 C18 C17 123.7(13) . . ?
N1 C18 H18 118.1 . . ?
C17 C18 H18 118.1 . . ?
C14A N1A C18A 116.1(11) . . ?
N1A C14A C15A 124.8(7) . . ?
N1A C14A H14A 117.6 . . ?
C15A C14A H14A 117.6 . . ?
C14A C15A C16A 119.1(6) . . ?
C14A C15A H15A 120.5 . . ?
C16A C15A H15A 120.5 . . ?
C17A C16A C15A 115.8(9) . . ?
C16A C17A C18A 120.6(11) . . ?
C16A C17A H17A 119.7 . . ?
C18A C17A H17A 119.7 . . ?
N1A C18A C17A 122.3(13) . . ?
N1A C18A H18A 118.8 . . ?
C17A C18A H18A 118.8 . . ?
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
F1 C1 1.360(2) . ?
F2 C5 1.363(2) . ?
O1 C10 1.352(2) . ?
O1 H1 0.900(16) . ?
O2 C13 1.226(2) . ?
O3 C13 1.310(2) . ?
O3 H3 0.927(17) . ?
N1 C18 1.306(11) . ?
N1 C14 1.334(11) . ?
C1 C2 1.365(3) . ?
C1 C6 1.366(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.386(2) . ?
C4 C7 1.481(2) . ?
C5 C6 1.366(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(2) . ?
C7 C12 1.398(2) . ?
C8 C9 1.390(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.401(3) . ?
C9 C13 1.469(3) . ?
C10 C11 1.386(3) . ?
C11 C12 1.368(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C14 C15 1.377(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.363(9) . ?
C17 C18 1.381(10) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
N1A C14A 1.318(11) . ?
N1A C18A 1.320(11) . ?
C14A C15A 1.371(6) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.378(8) . ?
C15A H15A 0.9300 . ?
C16A C17A 1.361(9) . ?
C17A C18A 1.384(10) . ?
C17A H17A 0.9300 . ?
C18A H18A 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.900(16) 1.752(19) 2.588(2) 153(2) . yes
O3 H3 N1^a 0.927(17) 1.75(2) 2.673(11) 177(3) . yes
O3 H3 N1A^b 0.927(17) 1.79(2) 2.691(12) 165(3) . yes
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
F1 C1 C2 C3 178.93(19) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C2 C3 C4 C7 -176.2(2) . . . . ?
C3 C4 C5 F2 -179.55(18) . . . . ?
C7 C4 C5 F2 -1.9(3) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C7 C4 C5 C6 176.2(2) . . . . ?
F1 C1 C6 C5 -178.8(2) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
F2 C5 C6 C1 178.5(2) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C5 C4 C7 C8 -136.0(2) . . . . ?
C3 C4 C7 C8 41.5(3) . . . . ?
C5 C4 C7 C12 45.2(3) . . . . ?
C3 C4 C7 C12 -137.3(2) . . . . ?
C12 C7 C8 C9 -0.3(3) . . . . ?
C4 C7 C8 C9 -179.24(18) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C7 C8 C9 C13 -179.39(19) . . . . ?
C8 C9 C10 O1 -179.86(19) . . . . ?
C13 C9 C10 O1 -0.6(3) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C13 C9 C10 C11 -179.98(19) . . . . ?
O1 C10 C11 C12 179.70(19) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
C10 C11 C12 C7 0.4(3) . . . . ?
C8 C7 C12 C11 0.2(3) . . . . ?
C4 C7 C12 C11 179.09(19) . . . . ?
C8 C9 C13 O2 -178.2(2) . . . . ?
C10 C9 C13 O2 2.6(3) . . . . ?
C8 C9 C13 O3 2.0(3) . . . . ?
C10 C9 C13 O3 -177.26(19) . . . . ?
C18 N1 C14 C15 4.9(19) . . . . ?
N1 C14 C15 C16 -2.4(10) . . . . ?
C14 C15 C16 C17 -7.2(12) . . . . ?
C15 C16 C17 C18 14(2) . . . . ?
C14 N1 C18 C17 2(3) . . . . ?
C16 C17 C18 N1 -12(4) . . . . ?
C18A N1A C14A C15A -4(2) . . . . ?
N1A C14A C15A C16A 1.5(11) . . . . ?
C14A C15A C16A C17A 7.1(11) . . . . ?
C15A C16A C17A C18A -14(2) . . . . ?
C14A N1A C18A C17A -3(3) . . . . ?
C16A C17A C18A N1A 12(4) . . . . ?
