#------------------------------------------------------------------------------
#$Date: 2019-11-23 17:42:21 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234264 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/61/4036119.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_4036119
loop_
_publ_author_name
'Krzeszewski, Maciej'
'Gryko, Daniel T.'
_publ_section_title
;
 χ-Shaped bis(areno)-1,4-dihydropyrrolo[3,2-b]pyrroles generated by
 oxidative aromatic coupling.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2893
_journal_page_last               2899
_journal_paper_doi               10.1021/acs.joc.5b00052
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C50 H42 N2'
_chemical_formula_sum            'C50 H42 N2'
_chemical_formula_weight         670.86
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.511(2)
_cell_angle_beta                 96.832(2)
_cell_angle_gamma                117.146(2)
_cell_formula_units_Z            1
_cell_length_a                   9.1073(3)
_cell_length_b                   9.5689(3)
_cell_length_c                   12.2523(4)
_cell_measurement_reflns_used    5477
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      67.21
_cell_measurement_theta_min      3.68
_cell_volume                     932.65(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9409
_diffrn_reflns_theta_full        67.64
_diffrn_reflns_theta_max         67.64
_diffrn_reflns_theta_min         3.68
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  0.9371
_exptl_absorpt_correction_T_min  0.8823
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0696P)²+0.2229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1499
_reflns_number_gt                2888
_reflns_number_total             3314
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00052_si_002.cif
_cod_data_source_block           mk189_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        932.65(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4036119
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.88166(16) 0.48096(15) 0.60406(10) 0.0413(3) Uani 1 1 d .
C1 C 0.1282(3) 0.2479(3) 0.7145(3) 0.0876(8) Uani 1 1 d .
H1A H 0.1885 0.3503 0.7599 0.131 Uiso 1 1 calc R
H1B H 0.0225 0.1885 0.7376 0.131 Uiso 1 1 calc R
H1C H 0.1094 0.2610 0.6381 0.131 Uiso 1 1 calc R
C2 C 0.2298(2) 0.1592(2) 0.72705(17) 0.0548(5) Uani 1 1 d .
C3 C 0.4028(2) 0.24777(19) 0.69452(13) 0.0427(4) Uani 1 1 d .
C4 C 0.4578(2) 0.3929(2) 0.65586(15) 0.0481(4) Uani 1 1 d .
H4 H 0.3877 0.4394 0.6495 0.058 Uiso 1 1 calc R
C5 C 0.6146(2) 0.46985(19) 0.62661(15) 0.0480(4) Uani 1 1 d .
H5 H 0.6484 0.5665 0.6003 0.058 Uiso 1 1 calc R
C6 C 0.72097(19) 0.40334(18) 0.63637(13) 0.0399(4) Uani 1 1 d .
C7 C 1.08508(18) 0.54145(17) 0.50148(12) 0.0381(3) Uani 1 1 d .
C8 C 0.6695(2) 0.25944(19) 0.67468(14) 0.0460(4) Uani 1 1 d .
H8 H 0.7406 0.2140 0.6815 0.055 Uiso 1 1 calc R
C9 C 0.5127(2) 0.18306(19) 0.70280(15) 0.0475(4) Uani 1 1 d .
H9 H 0.4792 0.0857 0.7280 0.057 Uiso 1 1 calc R
C10 C 0.1332(3) -0.0038(3) 0.6532(2) 0.0845(7) Uani 1 1 d .
H10A H 0.1186 0.0107 0.5768 0.127 Uiso 1 1 calc R
H10B H 0.0254 -0.0619 0.6741 0.127 Uiso 1 1 calc R
H10C H 0.1950 -0.0619 0.6627 0.127 Uiso 1 1 calc R
C11 C 0.2507(3) 0.1311(4) 0.8482(2) 0.0905(8) Uani 1 1 d .
H11A H 0.3121 0.0724 0.8564 0.136 Uiso 1 1 calc R
H11B H 0.1423 0.0719 0.8679 0.136 Uiso 1 1 calc R
H11C H 0.3107 0.2315 0.8961 0.136 Uiso 1 1 calc R
C12 C 1.16617(19) 0.61951(17) 0.61316(12) 0.0380(3) Uani 1 1 d .
C13 C 1.3376(2) 0.71587(17) 0.66949(13) 0.0416(4) Uani 1 1 d .
C14 C 1.3682(2) 0.75109(19) 0.78714(14) 0.0476(4) Uani 1 1 d .
C15 C 1.5373(3) 0.8316(2) 0.84104(18) 0.0674(6) Uani 1 1 d .
H15 H 1.5607 0.8527 0.9183 0.081 Uiso 1 1 calc R
C16 C 1.6679(2) 0.8798(2) 0.78346(19) 0.0696(6) Uani 1 1 d .
H16 H 1.7778 0.9288 0.8215 0.083 Uiso 1 1 calc R
C17 C 1.6358(2) 0.8552(2) 0.66926(18) 0.0613(5) Uani 1 1 d .
H17 H 1.7241 0.8934 0.6299 0.074 Uiso 1 1 calc R
C18 C 1.4744(2) 0.7749(2) 0.61347(16) 0.0509(4) Uani 1 1 d .
H18 H 1.4547 0.7589 0.5361 0.061 Uiso 1 1 calc R
C19 C 1.2292(2) 0.71145(19) 0.84736(13) 0.0499(4) Uani 1 1 d .
C20 C 1.2578(3) 0.7606(3) 0.96318(16) 0.0692(6) Uani 1 1 d .
H20 H 1.3674 0.8112 1.0018 0.083 Uiso 1 1 calc R
C21 C 1.1318(3) 0.7367(3) 1.02002(17) 0.0812(7) Uani 1 1 d .
H21 H 1.1553 0.7698 1.0964 0.097 Uiso 1 1 calc R
C22 C 0.9697(3) 0.6637(3) 0.96480(17) 0.0793(7) Uani 1 1 d .
H22 H 0.8833 0.6495 1.0036 0.095 Uiso 1 1 calc R
C23 C 0.9334(3) 0.6111(2) 0.85231(16) 0.0655(5) Uani 1 1 d .
H23 H 0.8225 0.5617 0.8161 0.079 Uiso 1 1 calc R
C24 C 1.0612(2) 0.63058(18) 0.79073(13) 0.0462(4) Uani 1 1 d .
C25 C 1.03549(19) 0.57784(17) 0.67323(12) 0.0400(4) 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'
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
C7 N1 C25 107.07(12) 2_766 .
C7 N1 C6 125.33(12) 2_766 .
C25 N1 C6 127.24(13) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C1 C2 C3 113.00(15) . .
C1 C2 C11 108.91(19) . .
C3 C2 C11 109.31(16) . .
C1 C2 C10 109.07(19) . .
C3 C2 C10 108.53(16) . .
C11 C2 C10 107.9(2) . .
C4 C3 C9 117.07(14) . .
C4 C3 C2 122.79(14) . .
C9 C3 C2 120.14(14) . .
C5 C4 C3 121.50(15) . .
C5 C4 H4 119.2 . .
C3 C4 H4 119.2 . .
C6 C5 C4 120.08(15) . .
C6 C5 H5 120.0 . .
C4 C5 H5 120.0 . .
C8 C6 C5 119.61(14) . .
C8 C6 N1 120.17(14) . .
C5 C6 N1 120.20(14) . .
C7 C7 N1 108.76(16) 2_766 2_766
C7 C7 C12 109.11(16) 2_766 .
N1 C7 C12 142.12(14) 2_766 .
C9 C8 C6 119.91(15) . .
C9 C8 H8 120.0 . .
C6 C8 H8 120.0 . .
C8 C9 C3 121.82(14) . .
C8 C9 H9 119.1 . .
C3 C9 H9 119.1 . .
C2 C10 H10A 109.5 . .
C2 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C2 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C2 C11 H11A 109.5 . .
C2 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C2 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C25 C12 C7 104.42(13) . .
C25 C12 C13 119.88(14) . .
C7 C12 C13 135.64(14) . .
C18 C13 C14 118.61(15) . .
C18 C13 C12 123.18(15) . .
C14 C13 C12 118.21(15) . .
C15 C14 C13 117.17(18) . .
C15 C14 C19 122.45(17) . .
C13 C14 C19 120.31(15) . .
C16 C15 C14 122.29(19) . .
C16 C15 H15 118.9 . .
C14 C15 H15 118.9 . .
C15 C16 C17 119.66(18) . .
C15 C16 H16 120.2 . .
C17 C16 H16 120.2 . .
C18 C17 C16 120.1(2) . .
C18 C17 H17 120.0 . .
C16 C17 H17 120.0 . .
C17 C18 C13 121.86(18) . .
C17 C18 H18 119.1 . .
C13 C18 H18 119.1 . .
C20 C19 C24 117.88(18) . .
C20 C19 C14 121.04(18) . .
C24 C19 C14 120.98(15) . .
C21 C20 C19 122.5(2) . .
C21 C20 H20 118.8 . .
C19 C20 H20 118.8 . .
C20 C21 C22 119.77(19) . .
C20 C21 H21 120.1 . .
C22 C21 H21 120.1 . .
C21 C22 C23 120.5(2) . .
C21 C22 H22 119.7 . .
C23 C22 H22 119.7 . .
C22 C23 C24 121.3(2) . .
C22 C23 H23 119.3 . .
C24 C23 H23 119.3 . .
C23 C24 C19 117.97(16) . .
C23 C24 C25 125.35(16) . .
C19 C24 C25 116.66(15) . .
C12 C25 N1 110.63(13) . .
C12 C25 C24 123.07(14) . .
N1 C25 C24 126.30(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C7 1.3852(19) 2_766
N1 C25 1.3961(19) .
N1 C6 1.4291(19) .
C1 C2 1.518(3) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C3 1.530(2) .
C2 C11 1.534(3) .
C2 C10 1.537(3) .
C3 C4 1.389(2) .
C3 C9 1.396(2) .
C4 C5 1.383(2) .
C4 H4 0.9300 .
C5 C6 1.380(2) .
C5 H5 0.9300 .
C6 C8 1.379(2) .
C7 C7 1.376(3) 2_766
C7 N1 1.3852(19) 2_766
C7 C12 1.439(2) .
C8 C9 1.377(2) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 C25 1.392(2) .
C12 C13 1.447(2) .
C13 C18 1.402(2) .
C13 C14 1.418(2) .
C14 C15 1.413(3) .
C14 C19 1.456(3) .
C15 C16 1.370(3) .
C15 H15 0.9300 .
C16 C17 1.374(3) .
C16 H16 0.9300 .
C17 C18 1.366(2) .
C17 H17 0.9300 .
C18 H18 0.9300 .
C19 C20 1.413(2) .
C19 C24 1.415(3) .
C20 C21 1.353(3) .
C20 H20 0.9300 .
C21 C22 1.369(3) .
C21 H21 0.9300 .
C22 C23 1.376(3) .
C22 H22 0.9300 .
C23 C24 1.411(3) .
C23 H23 0.9300 .
C24 C25 1.442(2) .
