#------------------------------------------------------------------------------
#$Date: 2021-07-05 21:14:04 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267244 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158088.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_7158088
loop_
_publ_author_name
'Liu, Yali'
'Wei, Yu'
'Yang, Zhen'
'Li, Yang'
'Liu, Yan'
'Liu, Ping'
_publ_section_title
;
 Highly selective C3-H iodination of pyrrolo[1,2-a]quinoxalines.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5191
_journal_page_last               5196
_journal_paper_doi               10.1039/d1ob00759a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C20 H14 N2'
_chemical_formula_sum            'C20 H14 N2'
_chemical_formula_weight         282.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-10 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6464(2)
_cell_length_b                   30.7588(9)
_cell_length_c                   5.8780(2)
_cell_measurement_reflns_used    6901
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.44
_cell_volume                     1382.47(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            16722
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.720
_diffrn_reflns_theta_min         2.745
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2872
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0341
_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)+(0.0319P)²+0.3048P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0813
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2646
_reflns_number_total             2872
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00759a2.cif
_cod_data_source_block           11
_cod_depositor_comments
'Adding full bibliography for 7158088--7158089.cif.'
_cod_database_code               7158088
_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_max   0.985
_shelx_estimated_absorpt_t_min   0.981
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C15(H15), C16(H16),
 C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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
C2 C -0.3287(3) -0.17870(7) -0.3064(4) 0.0302(5) Uani 1 1 d . . . . .
H2 H -0.275846 -0.165431 -0.435101 0.036 Uiso 1 1 calc R . . . .
C1 C -0.3315(3) -0.22423(7) -0.2879(4) 0.0256(5) Uani 1 1 d . . . . .
C3 C -0.4020(3) -0.15311(7) -0.1390(4) 0.0326(5) Uani 1 1 d . . . . .
H3 H -0.400906 -0.122367 -0.154220 0.039 Uiso 1 1 calc R . . . .
C4 C -0.4776(3) -0.17207(7) 0.0517(4) 0.0309(5) Uani 1 1 d . . . . .
H4 H -0.526060 -0.154140 0.167255 0.037 Uiso 1 1 calc R . . . .
C5 C -0.4830(3) -0.21685(7) 0.0750(4) 0.0281(5) Uani 1 1 d . . . . .
H5 H -0.534949 -0.229740 0.205419 0.034 Uiso 1 1 calc R . . . .
C6 C -0.4112(3) -0.24269(6) -0.0954(4) 0.0237(4) Uani 1 1 d . . . . .
C7 C -0.4843(3) -0.31550(7) 0.0771(4) 0.0269(5) Uani 1 1 d . . . . .
H7 H -0.538056 -0.306945 0.215736 0.032 Uiso 1 1 calc R . . . .
C8 C -0.4597(3) -0.35748(7) 0.0041(4) 0.0285(5) Uani 1 1 d . . . . .
H8 H -0.492443 -0.382965 0.084845 0.034 Uiso 1 1 calc R . . . .
C9 C -0.3773(3) -0.35642(7) -0.2117(4) 0.0265(5) Uani 1 1 d . . . . .
C10 C -0.3506(3) -0.31260(7) -0.2633(4) 0.0243(5) Uani 1 1 d . . . . .
C11 C -0.2683(3) -0.29067(7) -0.4444(4) 0.0264(5) Uani 1 1 d . . . . .
H11 H -0.218469 -0.307853 -0.562015 0.032 Uiso 1 1 calc R . . . .
C12 C -0.3313(3) -0.39227(7) -0.3597(4) 0.0278(5) Uani 1 1 d . . . . .
C13 C -0.3036(3) -0.42093(8) -0.4838(4) 0.0300(5) Uani 1 1 d . . . . .
C14 C -0.2766(3) -0.45792(7) -0.6340(4) 0.0275(5) Uani 1 1 d . . . . .
C15 C -0.3313(3) -0.49955(7) -0.5677(4) 0.0283(5) Uani 1 1 d . . . . .
H15 H -0.386019 -0.503635 -0.424136 0.034 Uiso 1 1 calc R . . . .
C16 C -0.3058(3) -0.53456(7) -0.7103(4) 0.0284(5) Uani 1 1 d . . . . .
H16 H -0.343587 -0.562565 -0.662943 0.034 Uiso 1 1 calc R . . . .
C17 C -0.2260(3) -0.52993(7) -0.9225(4) 0.0276(5) Uani 1 1 d . . . . .
C18 C -0.1717(3) -0.48862(7) -0.9879(4) 0.0296(5) Uani 1 1 d . . . . .
H18 H -0.116315 -0.484699 -1.131097 0.036 Uiso 1 1 calc R . . . .
C19 C -0.1974(3) -0.45304(7) -0.8462(4) 0.0303(5) Uani 1 1 d . . . . .
H19 H -0.160673 -0.425017 -0.894578 0.036 Uiso 1 1 calc R . . . .
C20 C -0.2026(3) -0.56880(7) -1.0763(5) 0.0339(5) Uani 1 1 d . . . . .
H20A H -0.097001 -0.584723 -1.031749 0.051 Uiso 1 1 calc GR . . . .
H20B H -0.191030 -0.558956 -1.234191 0.051 Uiso 1 1 calc GR . . . .
H20C H -0.304513 -0.587939 -1.062933 0.051 Uiso 1 1 calc GR . . . .
N1 N -0.4176(2) -0.28815(5) -0.0850(3) 0.0230(4) Uani 1 1 d . . . . .
N2 N -0.2553(2) -0.24857(6) -0.4625(3) 0.0280(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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C3 C2 C1 120.5(2) . . ?
C6 C1 C2 118.2(2) . . ?
N2 C1 C2 118.1(2) . . ?
N2 C1 C6 123.76(19) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 121.33(18) . . ?
C5 C6 N1 121.7(2) . . ?
N1 C6 C1 117.0(2) . . ?
C8 C7 H7 126.0 . . ?
N1 C7 H7 126.0 . . ?
N1 C7 C8 108.0(2) . . ?
C7 C8 H8 125.7 . . ?
C7 C8 C9 108.6(2) . . ?
C9 C8 H8 125.7 . . ?
C8 C9 C12 128.9(2) . . ?
C10 C9 C8 106.4(2) . . ?
C10 C9 C12 124.7(2) . . ?
C9 C10 C11 133.8(2) . . ?
N1 C10 C9 107.75(19) . . ?
N1 C10 C11 118.43(18) . . ?
C10 C11 H11 117.6 . . ?
N2 C11 C10 124.9(2) . . ?
N2 C11 H11 117.6 . . ?
C13 C12 C9 176.2(2) . . ?
C12 C13 C14 177.1(2) . . ?
C15 C14 C13 120.2(2) . . ?
C19 C14 C13 121.3(2) . . ?
C19 C14 C15 118.4(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.2 . . ?
C15 C16 C17 121.7(2) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C20 120.4(2) . . ?
C18 C17 C16 118.1(2) . . ?
C18 C17 C20 121.5(2) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.8(2) . . ?
C19 C18 H18 119.6 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.8(2) . . ?
C18 C19 H19 119.6 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7 N1 C6 131.05(19) . . ?
C7 N1 C10 109.26(16) . . ?
C10 N1 C6 119.68(19) . . ?
C11 N2 C1 116.14(19) . . ?
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
C2 H2 0.9500 . ?
C2 C1 1.405(3) . ?
C2 C3 1.379(3) . ?
C1 C6 1.405(3) . ?
C1 N2 1.398(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(3) . ?
C6 N1 1.400(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.373(3) . ?
C7 N1 1.369(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.417(3) . ?
C9 C10 1.396(3) . ?
C9 C12 1.448(3) . ?
C10 C11 1.409(3) . ?
C10 N1 1.388(3) . ?
C11 H11 0.9500 . ?
C11 N2 1.303(3) . ?
C12 C13 1.164(3) . ?
C13 C14 1.455(3) . ?
C14 C15 1.402(3) . ?
C14 C19 1.395(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.379(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.396(3) . ?
C17 C18 1.391(3) . ?
C17 C20 1.510(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(3) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
