#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/86/1508681.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_1508681
loop_
_publ_author_name
'Ammermann, Sven'
'Hrib, Christian'
'Jones, Peter G.'
'du Mont, Wolf-Walther'
'Kowalsky, Wolfgang'
'Johannes, Hans-Hermann'
_publ_section_title
;
 Pyrrolo[1,2-a]quinoxalines: novel synthesis via annulation of
 2-alkylquinoxalines.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5090
_journal_page_last               5093
_journal_paper_doi               10.1021/ol302348v
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C19 H16 N2'
_chemical_formula_weight         272.34
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.626(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3778(4)
_cell_length_b                   11.2485(6)
_cell_length_c                   15.3805(8)
_cell_measurement_reflns_used    9847
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.07
_cell_measurement_theta_min      2.27
_cell_volume                     1408.63(13)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0123
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            51880
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         31.12
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular tablet'
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    'rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0721P)²+0.3705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1190
_reflns_number_gt                4001
_reflns_number_total             4528
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302348v_si_002.cif
_cod_data_source_block           schab
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1408.63(12)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1508681
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.31621(8) 0.44987(6) 0.60239(5) 0.01476(14) Uani 1 1 d .
N2 N 0.64717(8) 0.38703(6) 0.61800(4) 0.01309(13) Uani 1 1 d .
C1 C 0.42647(10) 0.47093(7) 0.67670(5) 0.01344(15) Uani 1 1 d .
C2 C 0.59719(9) 0.44631(7) 0.68810(5) 0.01337(15) Uani 1 1 d .
C3 C 0.52906(10) 0.34861(7) 0.54288(5) 0.01395(15) Uani 1 1 d .
C4 C 0.56519(11) 0.27361(8) 0.47748(6) 0.01878(17) Uani 1 1 d .
H4 H 0.6731 0.2430 0.4843 0.023 Uiso 1 1 calc R
C5 C 0.44351(12) 0.24408(9) 0.40283(6) 0.02164(18) Uani 1 1 d .
H5 H 0.4689 0.1937 0.3583 0.026 Uiso 1 1 calc R
C6 C 0.28408(11) 0.28741(8) 0.39218(6) 0.02030(17) Uani 1 1 d .
H6 H 0.2023 0.2690 0.3398 0.024 Uiso 1 1 calc R
C7 C 0.24581(10) 0.35730(8) 0.45834(5) 0.01710(16) Uani 1 1 d .
H7 H 0.1365 0.3850 0.4518 0.021 Uiso 1 1 calc R
C8 C 0.36652(10) 0.38801(7) 0.53524(5) 0.01395(15) Uani 1 1 d .
C9 C 0.36299(10) 0.51882(7) 0.75212(5) 0.01469(15) Uani 1 1 d .
C10 C 0.26471(11) 0.62056(8) 0.74099(6) 0.01833(16) Uani 1 1 d .
H10 H 0.2425 0.6622 0.6857 0.022 Uiso 1 1 calc R
C11 C 0.19925(12) 0.66097(8) 0.81075(6) 0.02190(18) Uani 1 1 d .
H11 H 0.1342 0.7311 0.8032 0.026 Uiso 1 1 calc R
C12 C 0.22827(11) 0.59960(8) 0.89129(6) 0.02098(18) Uani 1 1 d .
H12 H 0.1828 0.6273 0.9386 0.025 Uiso 1 1 calc R
C13 C 0.32411(11) 0.49747(8) 0.90232(6) 0.02045(17) Uani 1 1 d .
H13 H 0.3433 0.4547 0.9571 0.025 Uiso 1 1 calc R
C14 C 0.39222(11) 0.45757(8) 0.83322(6) 0.01820(16) Uani 1 1 d .
H14 H 0.4589 0.3883 0.8414 0.022 Uiso 1 1 calc R
C15 C 0.73855(10) 0.48112(7) 0.75091(5) 0.01489(15) Uani 1 1 d .
C16 C 0.87196(10) 0.44224(7) 0.71743(5) 0.01593(16) Uani 1 1 d .
H16 H 0.9843 0.4534 0.7464 0.019 Uiso 1 1 calc R
C17 C 0.81594(10) 0.38539(7) 0.63625(5) 0.01491(15) Uani 1 1 d .
C18 C 0.91818(11) 0.34160(8) 0.57561(6) 0.01993(17) Uani 1 1 d .
H18A H 0.9151 0.2545 0.5738 0.024 Uiso 1 1 calc R
H18B H 1.0318 0.3683 0.5979 0.024 Uiso 1 1 calc R
H18C H 0.8748 0.3732 0.5153 0.024 Uiso 1 1 calc R
C19 C 0.75360(11) 0.55398(9) 0.83384(6) 0.02179(18) Uani 1 1 d .
H19A H 0.6743 0.6195 0.8218 0.026 Uiso 1 1 calc R
H19B H 0.8651 0.5863 0.8523 0.026 Uiso 1 1 calc R
H19C H 0.7312 0.5039 0.8817 0.026 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C8 117.61(7)
C17 N2 C3 131.05(7)
C17 N2 C2 109.02(6)
C3 N2 C2 119.77(7)
N1 C1 C2 123.52(7)
N1 C1 C9 115.96(7)
C2 C1 C9 120.47(7)
C15 C2 N2 107.75(7)
C15 C2 C1 133.86(7)
N2 C2 C1 117.82(7)
C4 C3 N2 123.26(7)
C4 C3 C8 119.84(7)
N2 C3 C8 116.89(7)
C5 C4 C3 119.94(8)
C4 C5 C6 120.75(8)
C7 C6 C5 119.62(8)
C6 C7 C8 120.89(8)
N1 C8 C7 117.64(7)
N1 C8 C3 123.43(7)
C7 C8 C3 118.81(7)
C14 C9 C10 119.24(7)
C14 C9 C1 119.94(7)
C10 C9 C1 120.68(7)
C11 C10 C9 120.08(8)
C12 C11 C10 120.50(8)
C11 C12 C13 119.65(8)
C12 C13 C14 120.14(8)
C13 C14 C9 120.37(8)
C2 C15 C16 106.10(7)
C2 C15 C19 129.11(8)
C16 C15 C19 124.61(7)
C17 C16 C15 110.15(7)
N2 C17 C16 106.98(7)
N2 C17 C18 126.26(7)
C16 C17 C18 126.50(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3108(10)
N1 C8 1.3905(10)
N2 C17 1.3753(10)
N2 C3 1.4007(10)
N2 C2 1.4125(10)
C1 C2 1.4266(11)
C1 C9 1.4864(11)
C2 C15 1.3964(11)
C3 C4 1.3996(11)
C3 C8 1.4104(11)
C4 C5 1.3843(12)
C5 C6 1.3947(13)
C6 C7 1.3821(12)
C7 C8 1.4062(11)
C9 C14 1.3953(11)
C9 C10 1.3966(11)
C10 C11 1.3913(12)
C11 C12 1.3887(13)
C12 C13 1.3889(13)
C13 C14 1.3936(11)
C15 C16 1.4060(11)
C15 C19 1.4963(12)
C16 C17 1.3829(11)
C17 C18 1.4908(11)
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
C18 H18B N1 0.98 2.54 3.4821(11) 161.5 1_655
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
C8 N1 C1 C2 7.54(12)
C8 N1 C1 C9 -170.13(7)
C17 N2 C2 C15 -0.34(9)
C3 N2 C2 C15 -176.21(7)
C17 N2 C2 C1 172.22(7)
C3 N2 C2 C1 -3.65(11)
N1 C1 C2 C15 164.70(9)
C9 C1 C2 C15 -17.74(14)
N1 C1 C2 N2 -5.46(12)
C9 C1 C2 N2 172.11(7)
C17 N2 C3 C4 15.49(13)
C2 N2 C3 C4 -169.69(8)
C17 N2 C3 C8 -165.19(8)
C2 N2 C3 C8 9.63(11)
N2 C3 C4 C5 -176.84(8)
C8 C3 C4 C5 3.86(13)
C3 C4 C5 C6 -0.58(14)
C4 C5 C6 C7 -2.22(14)
C5 C6 C7 C8 1.72(13)
C1 N1 C8 C7 175.17(7)
C1 N1 C8 C3 -0.75(12)
C6 C7 C8 N1 -174.58(7)
C6 C7 C8 C3 1.53(12)
C4 C3 C8 N1 171.57(8)
N2 C3 C8 N1 -7.78(11)
C4 C3 C8 C7 -4.31(12)
N2 C3 C8 C7 176.35(7)
N1 C1 C9 C14 121.83(9)
C2 C1 C9 C14 -55.91(11)
N1 C1 C9 C10 -53.85(11)
C2 C1 C9 C10 128.41(9)
C14 C9 C10 C11 1.02(13)
C1 C9 C10 C11 176.73(8)
C9 C10 C11 C12 -1.20(14)
C10 C11 C12 C13 0.33(14)
C11 C12 C13 C14 0.69(14)
C12 C13 C14 C9 -0.85(14)
C10 C9 C14 C13 -0.01(13)
C1 C9 C14 C13 -175.75(8)
N2 C2 C15 C16 0.08(9)
C1 C2 C15 C16 -170.79(9)
N2 C2 C15 C19 175.16(8)
C1 C2 C15 C19 4.29(16)
C2 C15 C16 C17 0.21(9)
C19 C15 C16 C17 -175.15(8)
C3 N2 C17 C16 175.71(8)
C2 N2 C17 C16 0.46(9)
C3 N2 C17 C18 1.32(14)
C2 N2 C17 C18 -173.92(8)
C15 C16 C17 N2 -0.42(9)
C15 C16 C17 C18 173.95(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652038
2 PubChem 139040632
