#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/07/7120736.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_7120736
loop_
_publ_author_name
'an, zhenyu'
'Zhao, Lian-Biao'
'Wu, Mingzhong'
'ni, jixiang'
'Qi, Zhenjie'
'Yu, Guiqin'
'Yan, Rulong'
_publ_section_title
;
 FeCl3-Catalyzed Synthesis of Pyrrolo[1,2-a]quinoxaline Derivatives from
 1-(2-Aminophenyl)pyrroles through Annulation and Cleavage of Cyclic
 Ethers
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC07089F
_journal_year                    2017
_chemical_formula_sum            'C14 H13 F N2 O'
_chemical_formula_weight         244.27
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-09-06 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.298(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.4593(5)
_cell_length_b                   15.9030(18)
_cell_length_c                   16.534(2)
_cell_measurement_temperature    296(2)
_cell_volume                     1172.2(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7389
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.390
_diffrn_reflns_theta_min         1.777
_exptl_absorpt_coefficient_mu    0.227
_exptl_crystal_density_diffrn    2.021
_exptl_crystal_F_000             713
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0394
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1494
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2241
_reflns_number_total             2887
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cc07089f2.cif
_cod_data_source_block           1
_cod_depositor_comments
;

2018-01-23
Z value and formula changed, original values are absurd
                 miguel
;
_cod_original_formula_sum        'C H F N O'
_cod_original_formula_units_Z    23
_cod_original_formula_weight     62.03
_cod_database_code               7120736
_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.
;
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
F1 F 0.00353(18) 0.28375(5) 0.61623(5) 0.0611(3) Uani 1 1 d . .
N2 N 0.6591(2) 0.20722(6) 0.83706(6) 0.0407(3) Uani 1 1 d . .
C11 C 0.9446(2) 0.31941(8) 0.90134(7) 0.0392(3) Uani 1 1 d . .
C5 C 0.5351(2) 0.26515(7) 0.78273(7) 0.0365(3) Uani 1 1 d . .
N1 N 0.8416(2) 0.37470(6) 0.84961(6) 0.0398(3) Uani 1 1 d . .
O1 O 0.9598(2) 0.45714(5) 1.16610(5) 0.0487(3) Uani 1 1 d . .
H1 H 0.9934 0.5078 1.1666 0.073 Uiso 1 1 calc R U
C6 C 0.3217(3) 0.24256(8) 0.72354(7) 0.0421(3) Uani 1 1 d . .
H6 H 0.2551 0.1874 0.7185 0.051 Uiso 1 1 calc R U
C3 C 0.5146(3) 0.40885(8) 0.73692(8) 0.0441(3) Uani 1 1 d . .
H3 H 0.5785 0.4644 0.7411 0.053 Uiso 1 1 calc R U
C4 C 0.6326(2) 0.34886(7) 0.79031(7) 0.0368(3) Uani 1 1 d . .
C10 C 0.8590(3) 0.23307(8) 0.89872(7) 0.0415(3) Uani 1 1 d . .
C2 C 0.3053(3) 0.38734(8) 0.67812(8) 0.0471(3) Uani 1 1 d . .
H2 H 0.2272 0.4275 0.6426 0.056 Uiso 1 1 calc R U
C13 C 0.9615(3) 0.38709(8) 1.03682(7) 0.0402(3) Uani 1 1 d . .
H13A H 0.8442 0.4338 1.0154 0.048 Uiso 1 1 calc R U
H13B H 0.8225 0.3445 1.0549 0.048 Uiso 1 1 calc R U
C1 C 0.2142(3) 0.30431(8) 0.67333(7) 0.0436(3) Uani 1 1 d . .
C14 C 1.1461(3) 0.41747(8) 1.10862(7) 0.0417(3) Uani 1 1 d . .
H14A H 1.2492 0.3702 1.1338 0.050 Uiso 1 1 calc R U
H14B H 1.2962 0.4570 1.0906 0.050 Uiso 1 1 calc R U
C12 C 1.1483(3) 0.35035(9) 0.96882(8) 0.0451(3) Uani 1 1 d . .
H12A H 1.2821 0.3931 0.9484 0.054 Uiso 1 1 calc R U
H12B H 1.2694 0.3042 0.9896 0.054 Uiso 1 1 calc R U
C9 C 0.9356(4) 0.16292(9) 0.94334(9) 0.0562(4) Uani 1 1 d . .
H9 H 1.0645 0.1613 0.9883 0.067 Uiso 1 1 calc R U
C7 C 0.6163(4) 0.12222(8) 0.84361(9) 0.0557(4) Uani 1 1 d . .
H7 H 0.4949 0.0893 0.8099 0.067 Uiso 1 1 calc R U
C8 C 0.7836(4) 0.09445(10) 0.90850(10) 0.0662(4) Uani 1 1 d . .
H8 H 0.7948 0.0391 0.9266 0.079 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 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C7 N2 C5 130.53(11)
C7 N2 C10 108.64(11)
C5 N2 C10 120.81(10)
N1 C11 C10 122.68(10)
N1 C11 C12 117.63(11)
C10 C11 C12 119.61(11)
N2 C5 C6 122.43(10)
N2 C5 C4 116.85(10)
C6 C5 C4 120.72(11)
C11 N1 C4 118.75(10)
C1 C6 C5 117.73(11)
C2 C3 C4 121.16(11)
C3 C4 N1 118.58(10)
C3 C4 C5 118.68(11)
N1 C4 C5 122.73(11)
C9 C10 N2 107.37(11)
C9 C10 C11 134.54(12)
N2 C10 C11 118.06(11)
C3 C2 C1 118.13(12)
C14 C13 C12 113.82(10)
F1 C1 C6 118.54(11)
F1 C1 C2 117.89(12)
C6 C1 C2 123.57(11)
O1 C14 C13 110.52(10)
C11 C12 C13 109.86(9)
C10 C9 C8 107.34(12)
C8 C7 N2 107.85(12)
C7 C8 C9 108.80(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C1 1.3567(13)
N2 C7 1.3697(17)
N2 C5 1.3925(15)
N2 C10 1.4005(14)
C11 N1 1.3031(16)
C11 C10 1.4255(18)
C11 C12 1.5055(15)
C5 C6 1.3965(16)
C5 C4 1.4052(16)
N1 C4 1.3989(14)
O1 C14 1.4240(15)
C6 C1 1.3658(18)
C3 C2 1.3756(17)
C3 C4 1.3948(17)
C10 C9 1.3762(19)
C2 C1 1.3831(19)
C13 C14 1.5087(15)
C13 C12 1.5304(16)
C9 C8 1.400(2)
C7 C8 1.366(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139188100
