#------------------------------------------------------------------------------
#$Date: 2019-11-24 00:41:16 +0200 (Sun, 24 Nov 2019) $
#$Revision: 235811 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/72/4037217.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_4037217
loop_
_publ_author_name
'Pigulski, Bartłomiej'
'Arendt, Agata'
'Tomilin, Denis N.'
'Sobenina, Lyubov N.'
'Trofimov, Boris A.'
'Szafert, Sławomir'
_publ_section_title
;
 Transition-Metal Free Mechanochemical Approach to Polyyne Substituted
 Pyrroles.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9188
_journal_page_last               9198
_journal_paper_doi               10.1021/acs.joc.6b01732
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C24 H16 N2 O2'
_chemical_formula_sum            'C24 H16 N2 O2'
_chemical_formula_weight         364.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.90(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.996(5)
_cell_length_b                   6.903(2)
_cell_length_c                   17.091(6)
_cell_measurement_reflns_used    1655
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.2672
_cell_measurement_theta_min      2.6860
_cell_volume                     1815.0(10)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.1956
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Xcalibur Onyx'
_diffrn_measurement_method       '/w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5088
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        63.365
_diffrn_reflns_theta_max         63.365
_diffrn_reflns_theta_min         2.872
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       plates
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.884
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.884
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0670
_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)+(0.1176P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1700
_refine_ls_wR_factor_ref         0.1847
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1634
_reflns_number_total             2844
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b01732_si_001.cif
_cod_data_source_block           2-C8THI-Vin
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037217
_shelx_shelxl_version_number     2014/7
_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   0.766
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O2 O 0.27499(15) 0.1201(3) 0.84804(13) 0.0371(6) Uani 1 1 d . .
N2 N -0.32711(16) 0.1071(4) -0.16464(14) 0.0247(6) Uani 1 1 d . .
C22 C -0.2834(2) 0.1185(5) -0.36525(18) 0.0283(7) Uani 1 1 d . .
H22A H -0.2392 0.0289 -0.3754 0.034 Uiso 1 1 calc R U
H22B H -0.2705 0.2504 -0.3815 0.034 Uiso 1 1 calc R U
C5 C -0.00883(19) 0.1304(5) 0.24319(18) 0.0263(7) Uani 1 1 d . .
C13 C 0.3053(2) 0.1108(5) 0.65012(18) 0.0290(7) Uani 1 1 d . .
H13 H 0.3670 0.1050 0.6642 0.035 Uiso 1 1 calc R U
C9 C 0.16534(19) 0.1225(4) 0.54979(17) 0.0237(7) Uani 1 1 d . .
C7 C 0.07597(19) 0.1315(4) 0.39512(19) 0.0283(8) Uani 1 1 d . .
C1 C -0.1874(2) 0.1176(4) -0.05594(18) 0.0270(7) Uani 1 1 d . .
C3 C -0.0957(2) 0.1249(4) 0.09247(19) 0.0279(7) Uani 1 1 d . .
C17 C -0.2792(2) 0.1169(4) -0.27675(18) 0.0260(7) Uani 1 1 d . .
C4 C -0.05420(19) 0.1275(5) 0.16390(18) 0.0281(8) Uani 1 1 d . .
C6 C 0.03150(19) 0.1325(4) 0.31489(19) 0.0270(7) Uani 1 1 d . .
N1 N 0.31358(17) 0.1170(4) 0.79548(15) 0.0293(7) Uani 1 1 d . .
C2 C -0.1430(2) 0.1221(4) 0.01319(19) 0.0281(7) Uani 1 1 d . .
C8 C 0.1159(2) 0.1274(4) 0.46645(19) 0.0276(7) Uani 1 1 d . .
C11 C 0.1728(2) 0.1259(4) 0.69300(18) 0.0270(7) Uani 1 1 d . .
H11 H 0.1457 0.1305 0.7359 0.032 Uiso 1 1 calc R U
C16 C -0.2061(2) 0.1186(4) -0.20669(18) 0.0271(7) Uani 1 1 d . .
H16 H -0.1468 0.1235 -0.2067 0.033 Uiso 1 1 calc R U
O1 O 0.39332(14) 0.1155(3) 0.80912(14) 0.0383(6) Uani 1 1 d . .
C19 C -0.4437(2) 0.1074(5) -0.30086(19) 0.0308(8) Uani 1 1 d . .
H19A H -0.4787 0.2025 -0.2801 0.037 Uiso 1 1 calc R U
H19B H -0.4689 -0.0230 -0.2989 0.037 Uiso 1 1 calc R U
C12 C 0.2616(2) 0.1171(4) 0.70870(17) 0.0254(7) Uani 1 1 d . .
C15 C -0.23688(19) 0.1117(4) -0.13941(18) 0.0250(7) Uani 1 1 d . .
C18 C -0.35245(19) 0.1113(4) -0.25022(17) 0.0247(7) Uani 1 1 d . .
C14 C 0.2555(2) 0.1130(5) 0.56871(19) 0.0305(8) Uani 1 1 d . .
H14 H 0.2834 0.1081 0.5263 0.037 Uiso 1 1 calc R U
C20 C -0.4452(2) 0.1578(5) -0.38875(19) 0.0324(8) Uani 1 1 d . .
H20A H -0.5024 0.1210 -0.4255 0.039 Uiso 1 1 calc R U
H20B H -0.4385 0.2996 -0.3932 0.039 Uiso 1 1 calc R U
C10 C 0.1235(2) 0.1281(5) 0.61118(18) 0.0297(8) Uani 1 1 d . .
H10 H 0.0619 0.1333 0.5978 0.036 Uiso 1 1 calc R U
C23 C -0.3883(2) 0.0879(5) -0.1186(2) 0.0322(8) Uani 1 1 d . .
H23 H -0.4471 0.1184 -0.1457 0.039 Uiso 1 1 calc R U
C21 C -0.3741(2) 0.0563(5) -0.41610(19) 0.0335(8) Uani 1 1 d . .
H21A H -0.3805 0.0867 -0.4741 0.040 Uiso 1 1 calc R U
H21B H -0.3803 -0.0855 -0.4112 0.040 Uiso 1 1 calc R U
C24 C -0.3719(3) 0.0318(5) -0.0416(2) 0.0397(9) Uani 1 1 d . .
H24A H -0.3142 -0.0003 -0.0117 0.048 Uiso 1 1 calc R U
H24B H -0.4177 0.0238 -0.0163 0.048 Uiso 1 1 calc R 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'
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
C15 N2 C18 107.5(2)
C15 N2 C23 130.2(3)
C18 N2 C23 122.1(3)
C17 C22 C21 110.1(3)
C17 C22 H22A 109.6
C21 C22 H22A 109.6
C17 C22 H22B 109.6
C21 C22 H22B 109.6
H22A C22 H22B 108.1
C6 C5 C4 179.5(4)
C12 C13 C14 117.4(3)
C12 C13 H13 121.3
C14 C13 H13 121.3
C10 C9 C14 120.6(3)
C10 C9 C8 120.2(3)
C14 C9 C8 119.3(3)
C8 C7 C6 178.9(4)
C2 C1 C15 177.5(3)
C4 C3 C2 179.2(3)
C18 C17 C16 107.5(3)
C18 C17 C22 122.0(3)
C16 C17 C22 130.4(3)
C3 C4 C5 179.6(3)
C5 C6 C7 179.0(4)
O2 N1 O1 124.5(3)
O2 N1 C12 118.4(3)
O1 N1 C12 117.1(3)
C1 C2 C3 177.6(3)
C7 C8 C9 178.3(3)
C12 C11 C10 117.6(3)
C12 C11 H11 121.2
C10 C11 H11 121.2
C15 C16 C17 107.7(3)
C15 C16 H16 126.1
C17 C16 H16 126.1
C18 C19 C20 108.4(3)
C18 C19 H19A 110.0
C20 C19 H19A 110.0
C18 C19 H19B 110.0
C20 C19 H19B 110.0
H19A C19 H19B 108.4
C13 C12 C11 124.5(3)
C13 C12 N1 118.0(3)
C11 C12 N1 117.4(3)
C16 C15 N2 108.8(3)
C16 C15 C1 127.5(3)
N2 C15 C1 123.7(3)
C17 C18 N2 108.4(3)
C17 C18 C19 127.2(3)
N2 C18 C19 124.4(3)
C9 C14 C13 120.2(3)
C9 C14 H14 119.9
C13 C14 H14 119.9
C21 C20 C19 112.7(3)
C21 C20 H20A 109.1
C19 C20 H20A 109.1
C21 C20 H20B 109.1
C19 C20 H20B 109.1
H20A C20 H20B 107.8
C9 C10 C11 119.7(3)
C9 C10 H10 120.1
C11 C10 H10 120.1
C24 C23 N2 126.6(3)
C24 C23 H23 116.7
N2 C23 H23 116.7
C20 C21 C22 111.7(3)
C20 C21 H21A 109.3
C22 C21 H21A 109.3
C20 C21 H21B 109.3
C22 C21 H21B 109.3
H21A C21 H21B 107.9
C23 C24 H24A 120.0
C23 C24 H24B 120.0
H24A C24 H24B 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 N1 1.222(3)
N2 C15 1.389(4)
N2 C18 1.407(4)
N2 C23 1.421(4)
C22 C17 1.496(4)
C22 C21 1.534(4)
C22 H22A 0.9900
C22 H22B 0.9900
C5 C6 1.218(4)
C5 C4 1.351(4)
C13 C12 1.370(4)
C13 C14 1.401(4)
C13 H13 0.9500
C9 C10 1.391(4)
C9 C14 1.391(4)
C9 C8 1.428(4)
C7 C8 1.212(4)
C7 C6 1.361(4)
C1 C2 1.201(4)
C1 C15 1.430(4)
C3 C4 1.219(4)
C3 C2 1.359(4)
C17 C18 1.368(4)
C17 C16 1.426(4)
N1 O1 1.232(3)
N1 C12 1.489(4)
C11 C12 1.372(4)
C11 C10 1.405(4)
C11 H11 0.9500
C16 C15 1.370(4)
C16 H16 0.9500
C19 C18 1.480(4)
C19 C20 1.536(4)
C19 H19A 0.9900
C19 H19B 0.9900
C14 H14 0.9500
C20 C21 1.515(4)
C20 H20A 0.9900
C20 H20B 0.9900
C10 H10 0.9500
C23 C24 1.327(5)
C23 H23 0.9500
C21 H21A 0.9900
C21 H21B 0.9900
C24 H24A 0.9500
C24 H24B 0.9500
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
C21 C22 C17 C18 -15.8(4)
C21 C22 C17 C16 163.4(3)
C18 C17 C16 C15 0.6(4)
C22 C17 C16 C15 -178.7(3)
C14 C13 C12 C11 -0.2(5)
C14 C13 C12 N1 -179.3(3)
C10 C11 C12 C13 0.2(5)
C10 C11 C12 N1 179.4(3)
O2 N1 C12 C13 -179.1(3)
O1 N1 C12 C13 1.6(4)
O2 N1 C12 C11 1.7(4)
O1 N1 C12 C11 -177.7(3)
C17 C16 C15 N2 -0.4(4)
C17 C16 C15 C1 -177.5(3)
C18 N2 C15 C16 0.0(3)
C23 N2 C15 C16 175.8(3)
C18 N2 C15 C1 177.3(3)
C23 N2 C15 C1 -7.0(5)
C16 C17 C18 N2 -0.7(3)
C22 C17 C18 N2 178.8(3)
C16 C17 C18 C19 -179.9(3)
C22 C17 C18 C19 -0.4(5)
C15 N2 C18 C17 0.4(3)
C23 N2 C18 C17 -175.8(3)
C15 N2 C18 C19 179.7(3)
C23 N2 C18 C19 3.5(5)
C20 C19 C18 C17 -12.9(5)
C20 C19 C18 N2 168.0(3)
C10 C9 C14 C13 -0.5(5)
C8 C9 C14 C13 179.1(3)
C12 C13 C14 C9 0.3(5)
C18 C19 C20 C21 43.3(4)
C14 C9 C10 C11 0.6(5)
C8 C9 C10 C11 -179.1(3)
C12 C11 C10 C9 -0.4(5)
C15 N2 C23 C24 -14.4(5)
C18 N2 C23 C24 160.8(3)
C19 C20 C21 C22 -62.8(4)
C17 C22 C21 C20 46.0(4)
