#------------------------------------------------------------------------------
#$Date: 2020-09-23 02:23:30 +0300 (Wed, 23 Sep 2020) $
#$Revision: 256630 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/88/4038826.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_4038826
loop_
_publ_author_name
'Tasior, Mariusz'
'Vakuliuk, Olena'
'Koga, Daiki'
'Koszarna, Beata'
'Górski, Krzysztof'
'Grzybowski, Marek'
'Kielesiński, Łukasz'
'Krzeszewski, Maciej'
'Gryko, Daniel T.'
_publ_section_title
;
 Method for the Large-Scale Synthesis of Multifunctional
 1,4-Dihydro-pyrrolo[3,2-b]pyrroles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01665
_journal_year                    2020
_chemical_formula_moiety         'C42 H30 F12 N2'
_chemical_formula_sum            'C42 H30 F12 N2'
_chemical_formula_weight         790.68
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 97.551(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0701(1)
_cell_length_b                   25.7968(6)
_cell_length_c                   10.8547(3)
_cell_measurement_reflns_used    6444
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      69.9400
_cell_measurement_theta_min      3.4240
_cell_volume                     1684.99(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector_area_resol_mean 16.2974
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray Source'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17251
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.998
_diffrn_reflns_theta_min         7.559
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_description       needle
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0349
_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)+(0.0537P)²+0.5685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2728
_reflns_number_total             3194
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01665_si_002.cif
_cod_data_source_block           ov_892
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038826
_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   0.679
_shelx_estimated_absorpt_t_max   0.942
_shelxl_version_number           2013-3
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
F4 F 0.25085(17) 0.56198(4) 1.02067(8) 0.0358(2) Uani 1 1 d . . . . .
F5 F 0.04779(17) 0.58621(4) 0.85507(9) 0.0400(3) Uani 1 1 d . . . . .
F6 F 0.3804(2) 0.61463(4) 0.89523(12) 0.0503(3) Uani 1 1 d . . . . .
C54 C 0.2557(3) 0.57255(6) 0.90008(14) 0.0261(3) Uani 1 1 d . . . . .
C50 C 0.2945(3) 0.27061(6) 0.45996(14) 0.0247(3) Uani 1 1 d . . . . .
C51 C 0.4485(3) 0.22313(6) 0.46736(16) 0.0307(3) Uani 1 1 d . . . . .
H51A H 0.5310 0.2207 0.5510 0.046 Uiso 1 1 calc R U . . .
H51B H 0.5532 0.2267 0.4064 0.046 Uiso 1 1 calc R U . . .
H51C H 0.3594 0.1917 0.4493 0.046 Uiso 1 1 calc R U . . .
C53 C 0.1265(3) 0.26220(6) 0.55209(15) 0.0285(3) Uani 1 1 d . . . . .
H53A H 0.0210 0.2911 0.5461 0.043 Uiso 1 1 calc R U . . .
H53B H 0.2053 0.2603 0.6368 0.043 Uiso 1 1 calc R U . . .
H53C H 0.0457 0.2297 0.5322 0.043 Uiso 1 1 calc R U . . .
C52 C 0.1699(3) 0.27473(6) 0.32722(15) 0.0303(3) Uani 1 1 d . . . . .
H52A H 0.2775 0.2780 0.2678 0.046 Uiso 1 1 calc R U . . .
H52B H 0.0731 0.3053 0.3213 0.046 Uiso 1 1 calc R U . . .
H52C H 0.0798 0.2435 0.3081 0.046 Uiso 1 1 calc R U . . .
F3 F 0.17953(16) 0.38812(4) 0.94450(9) 0.0323(2) Uani 1 1 d . . . . .
F1 F 0.04402(15) 0.36777(4) 0.75838(9) 0.0298(2) Uani 1 1 d . . . . .
F2 F 0.38191(15) 0.34633(3) 0.83135(8) 0.0281(2) Uani 1 1 d . . . . .
N1 N 0.80932(19) 0.45683(5) 0.54556(11) 0.0194(2) Uani 1 1 d . . . . .
C7 C 0.4618(2) 0.44140(5) 0.69320(13) 0.0202(3) Uani 1 1 d . . . . .
C14 C 0.7376(2) 0.49885(5) 0.61123(13) 0.0196(3) Uani 1 1 d . . . . .
C5 C 0.5157(2) 0.40147(5) 0.60362(13) 0.0202(3) Uani 1 1 d . . . . .
C6 C 0.6896(2) 0.41048(5) 0.53208(13) 0.0198(3) Uani 1 1 d . . . . .
C17 C 0.8633(2) 0.54237(5) 0.59356(13) 0.0204(3) Uani 1 1 d . . . . .
H17 H 0.8489 0.5760 0.6273 0.024 Uiso 1 1 calc R U . . .
C12 C 0.4971(2) 0.53324(6) 0.75524(13) 0.0218(3) Uani 1 1 d . . . . .
H12 H 0.5654 0.5661 0.7486 0.026 Uiso 1 1 calc R U . . .
C1 C 0.7359(2) 0.37468(6) 0.44274(14) 0.0231(3) Uani 1 1 d . . . . .
H1 H 0.8547 0.3811 0.3959 0.028 Uiso 1 1 calc R U . . .
C8 C 0.3144(2) 0.43578(6) 0.78467(13) 0.0218(3) Uani 1 1 d . . . . .
C16 C 0.9829(2) 0.47386(5) 0.48525(13) 0.0200(3) Uani 1 1 d . . . . .
C4 C 0.3885(2) 0.35625(6) 0.57568(13) 0.0215(3) Uani 1 1 d . . . . .
H4 H 0.2650 0.3503 0.6193 0.026 Uiso 1 1 calc R U . . .
C13 C 0.5615(2) 0.49082(5) 0.68681(13) 0.0199(3) Uani 1 1 d . . . . .
C2 C 0.6115(3) 0.33018(6) 0.42153(14) 0.0240(3) Uani 1 1 d . . . . .
H2 H 0.6468 0.3061 0.3609 0.029 Uiso 1 1 calc R U . . .
C11 C 0.3361(2) 0.52731(6) 0.83151(13) 0.0229(3) Uani 1 1 d . . . . .
C10 C 0.2490(2) 0.47822(6) 0.84879(13) 0.0237(3) Uani 1 1 d . . . . .
H10 H 0.1434 0.4739 0.9053 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4335(2) 0.31990(5) 0.48803(14) 0.0220(3) Uani 1 1 d . . . . .
C9 C 0.2308(3) 0.38457(6) 0.82822(14) 0.0250(3) Uani 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 0.0181 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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
F6 C54 F5 106.56(14) . . ?
F6 C54 F4 106.88(13) . . ?
F5 C54 F4 105.62(12) . . ?
F6 C54 C11 113.07(12) . . ?
F5 C54 C11 112.11(13) . . ?
F4 C54 C11 112.11(13) . . ?
C3 C50 C53 112.51(12) . . ?
C3 C50 C51 109.61(13) . . ?
C53 C50 C51 107.76(13) . . ?
C3 C50 C52 108.56(12) . . ?
C53 C50 C52 109.41(13) . . ?
C51 C50 C52 108.93(13) . . ?
C16 N1 C6 129.84(12) . . ?
C16 N1 C14 107.61(11) . . ?
C6 N1 C14 121.64(12) . . ?
C13 C7 C8 115.83(13) . . ?
C13 C7 C5 117.44(12) . . ?
C8 C7 C5 126.70(13) . . ?
C17 C14 N1 110.13(12) . . ?
C17 C14 C13 131.04(13) . . ?
N1 C14 C13 118.78(12) . . ?
C4 C5 C6 116.53(13) . . ?
C4 C5 C7 123.66(13) . . ?
C6 C5 C7 119.51(13) . . ?
C1 C6 N1 119.35(13) . . ?
C1 C6 C5 120.52(13) . . ?
N1 C6 C5 120.04(12) . . ?
C14 C17 C16 105.31(12) . 3_766 ?
C11 C12 C13 120.14(14) . . ?
C2 C1 C6 120.83(13) . . ?
C10 C8 C7 121.12(13) . . ?
C10 C8 C9 113.81(13) . . ?
C7 C8 C9 124.89(13) . . ?
N1 C16 C16 107.33(15) . 3_766 ?
N1 C16 C17 143.04(13) . 3_766 ?
C16 C16 C17 109.63(15) 3_766 3_766 ?
C3 C4 C5 123.69(13) . . ?
C12 C13 C7 121.62(13) . . ?
C12 C13 C14 117.77(13) . . ?
C7 C13 C14 120.60(13) . . ?
C1 C2 C3 120.98(13) . . ?
C12 C11 C10 119.74(13) . . ?
C12 C11 C54 121.16(14) . . ?
C10 C11 C54 119.08(13) . . ?
C8 C10 C11 120.80(13) . . ?
C4 C3 C2 117.37(13) . . ?
C4 C3 C50 122.91(13) . . ?
C2 C3 C50 119.70(13) . . ?
F3 C9 F2 105.55(12) . . ?
F3 C9 F1 105.57(12) . . ?
F2 C9 F1 107.37(12) . . ?
F3 C9 C8 111.28(12) . . ?
F2 C9 C8 113.15(12) . . ?
F1 C9 C8 113.34(12) . . ?
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
F4 C54 1.3412(18) . ?
F5 C54 1.3390(19) . ?
F6 C54 1.3284(19) . ?
C54 C11 1.500(2) . ?
C50 C3 1.534(2) . ?
C50 C53 1.535(2) . ?
C50 C51 1.536(2) . ?
C50 C52 1.541(2) . ?
F3 C9 1.3423(17) . ?
F1 C9 1.3500(19) . ?
F2 C9 1.3442(18) . ?
N1 C16 1.3832(18) . ?
N1 C6 1.3968(18) . ?
N1 C14 1.3979(17) . ?
C7 C13 1.417(2) . ?
C7 C8 1.429(2) . ?
C7 C5 1.4823(19) . ?
C14 C17 1.385(2) . ?
C14 C13 1.446(2) . ?
C5 C4 1.410(2) . ?
C5 C6 1.409(2) . ?
C6 C1 1.394(2) . ?
C17 C16 1.410(2) 3_766 ?
C12 C11 1.370(2) . ?
C12 C13 1.406(2) . ?
C1 C2 1.377(2) . ?
C8 C10 1.383(2) . ?
C8 C9 1.513(2) . ?
C16 C16 1.395(3) 3_766 ?
C16 C17 1.410(2) 3_766 ?
C4 C3 1.388(2) . ?
C2 C3 1.401(2) . ?
C11 C10 1.394(2) . ?
