#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:33:56 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257638 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/97/7059764.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_7059764
loop_
_publ_author_name
'Feng, Juhua'
'Wang, Siyuan'
'Feng, Jinxiang'
'Li, Qiuju'
'Yue, Junping'
'Yue, Guizhou'
'Zou, Ping'
'Wang, Guangtu'
_publ_section_title
;
 Mild and efficient synthesis of
 trans-3-aryl-2-nitro-2,3-dihydrobenzofurans on water
;
_journal_issue                   28
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11937
_journal_page_last               11940
_journal_paper_doi               10.1039/D0NJ00548G
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C15 H10 Br N O5'
_chemical_formula_sum            'C15 H10 Br N O5'
_chemical_formula_weight         364.15
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-10-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-21 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.390(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6910(7)
_cell_length_b                   13.9407(12)
_cell_length_c                   13.4635(12)
_cell_measurement_reflns_used    7800
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.519
_cell_measurement_theta_min      2.922
_cell_volume                     1441.0(2)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22584
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.627
_diffrn_reflns_theta_min         3.029
_exptl_absorpt_coefficient_mu    2.876
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0740 before and 0.0481 after correction.
The Ratio of minimum to maximum transmission is 0.8781.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0456
_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)+(0.0718P)²+0.5783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1347
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2272
_reflns_number_total             3330
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj00548g2.cif
_cod_data_source_block           222
_cod_depositor_comments
;Adding full bibliography for 7059764.cif.

 Adding full bibliography for 7059764.cif.
;
_cod_database_code               7059764
_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   0.689
_shelx_estimated_absorpt_t_min   0.522
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C5(H5), C2(H2), C3(H3), C4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.08757(5) 0.57884(3) 0.36571(3) 0.0878(2) Uani 1 1 d . . . . .
O3 O 0.5953(2) 0.56431(13) 0.08983(13) 0.0427(4) Uani 1 1 d . . . . .
O1 O 0.1497(3) 0.5775(2) 0.04239(19) 0.0768(8) Uani 1 1 d . . . . .
N1 N 0.3012(3) 0.59892(17) 0.03909(16) 0.0453(6) Uani 1 1 d . . . . .
O2 O 0.3608(3) 0.65350(18) -0.01973(17) 0.0728(7) Uani 1 1 d . . . . .
C10 C 0.5548(3) 0.65992(17) 0.22528(17) 0.0363(5) Uani 1 1 d . . . . .
O5 O 1.0103(3) 0.8069(2) 0.2146(2) 0.0815(8) Uani 1 1 d . . . . .
C9 C 0.6617(3) 0.63916(19) 0.15019(18) 0.0387(6) Uani 1 1 d . . . . .
O4 O 0.8338(4) 0.84588(17) 0.34172(18) 0.0752(7) Uani 1 1 d . . . . .
C8 C 0.4253(3) 0.54787(19) 0.11551(18) 0.0373(6) Uani 1 1 d . . . . .
H8 H 0.400703 0.478910 0.116301 0.045 Uiso 1 1 calc R . . . .
C6 C 0.4164(4) 0.51652(18) 0.30045(17) 0.0387(6) Uani 1 1 d . . . . .
C1 C 0.2913(4) 0.5013(2) 0.36798(19) 0.0475(7) Uani 1 1 d . . . . .
C7 C 0.4024(3) 0.59221(18) 0.21948(17) 0.0364(5) Uani 1 1 d . . . . .
H7 H 0.292102 0.627247 0.220744 0.044 Uiso 1 1 calc R . . . .
C11 C 0.6019(4) 0.73038(19) 0.29589(19) 0.0456(7) Uani 1 1 d . . . . .
H11 H 0.531400 0.746701 0.347078 0.055 Uiso 1 1 calc R . . . .
C12 C 0.7585(4) 0.7733(2) 0.2842(2) 0.0491(7) Uani 1 1 d . . . . .
C14 C 0.8199(4) 0.6829(2) 0.1369(2) 0.0503(7) Uani 1 1 d . . . . .
H14 H 0.889941 0.668113 0.085088 0.060 Uiso 1 1 calc R . . . .
C13 C 0.8624(4) 0.7503(2) 0.2079(2) 0.0536(8) Uani 1 1 d . . . . .
C5 C 0.5660(5) 0.4586(2) 0.3100(2) 0.0546(8) Uani 1 1 d . . . . .
H5 H 0.655049 0.467888 0.267156 0.066 Uiso 1 1 calc R . . . .
C2 C 0.3092(6) 0.4307(2) 0.4403(2) 0.0641(9) Uani 1 1 d . . . . .
H2 H 0.222551 0.421574 0.484765 0.077 Uiso 1 1 calc R . . . .
C3 C 0.4546(6) 0.3746(2) 0.4459(2) 0.0673(10) Uani 1 1 d . . . . .
H3 H 0.466218 0.326699 0.493857 0.081 Uiso 1 1 calc R . . . .
C4 C 0.5827(5) 0.3881(2) 0.3821(2) 0.0626(9) Uani 1 1 d . . . . .
H4 H 0.681824 0.349798 0.386867 0.075 Uiso 1 1 calc R . . . .
C15 C 1.0032(6) 0.8583(3) 0.3056(3) 0.0887(13) Uani 1 1 d . . . . .
H15A H 1.025620 0.925832 0.294717 0.106 Uiso 1 1 calc R . . . .
H15B H 1.091047 0.834152 0.353961 0.106 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'
Br Br -0.2901 2.4595 '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'
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
C8 O3 C9 107.14(19) . . ?
O1 N1 O2 125.8(3) . . ?
O1 N1 C8 115.1(2) . . ?
O2 N1 C8 119.1(2) . . ?
C9 C10 C7 109.2(2) . . ?
C9 C10 C11 120.4(3) . . ?
C11 C10 C7 130.2(2) . . ?
C13 O5 C15 105.7(3) . . ?
C10 C9 O3 111.8(2) . . ?
C10 C9 C14 124.9(3) . . ?
C14 C9 O3 123.2(2) . . ?
C12 O4 C15 105.0(3) . . ?
O3 C8 N1 108.3(2) . . ?
O3 C8 H8 110.4 . . ?
O3 C8 C7 108.5(2) . . ?
N1 C8 H8 110.4 . . ?
N1 C8 C7 108.7(2) . . ?
C7 C8 H8 110.4 . . ?
C1 C6 C7 123.9(2) . . ?
C1 C6 C5 116.8(3) . . ?
C5 C6 C7 119.2(2) . . ?
C6 C1 Br1 120.6(2) . . ?
C6 C1 C2 121.9(3) . . ?
C2 C1 Br1 117.5(3) . . ?
C10 C7 C8 99.7(2) . . ?
C10 C7 C6 112.2(2) . . ?
C10 C7 H7 111.0 . . ?
C8 C7 H7 111.0 . . ?
C6 C7 C8 111.4(2) . . ?
C6 C7 H7 111.0 . . ?
C10 C11 H11 122.4 . . ?
C12 C11 C10 115.2(3) . . ?
C12 C11 H11 122.4 . . ?
C11 C12 O4 127.0(3) . . ?
C11 C12 C13 122.7(3) . . ?
C13 C12 O4 110.3(3) . . ?
C9 C14 H14 123.5 . . ?
C13 C14 C9 112.9(3) . . ?
C13 C14 H14 123.5 . . ?
C12 C13 O5 109.3(3) . . ?
C14 C13 O5 126.9(3) . . ?
C14 C13 C12 123.9(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.7 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 119.9 . . ?
O5 C15 O4 108.3(3) . . ?
O5 C15 H15A 110.0 . . ?
O5 C15 H15B 110.0 . . ?
O4 C15 H15A 110.0 . . ?
O4 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
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
Br1 C1 1.902(3) . ?
O3 C9 1.400(3) . ?
O3 C8 1.391(3) . ?
O1 N1 1.206(3) . ?
N1 O2 1.208(3) . ?
N1 C8 1.536(3) . ?
C10 C9 1.371(4) . ?
C10 C7 1.503(4) . ?
C10 C11 1.400(4) . ?
O5 C13 1.383(4) . ?
O5 C15 1.424(6) . ?
C9 C14 1.382(4) . ?
O4 C12 1.380(3) . ?
O4 C15 1.428(5) . ?
C8 H8 0.9800 . ?
C8 C7 1.550(3) . ?
C6 C1 1.379(4) . ?
C6 C7 1.516(3) . ?
C6 C5 1.405(4) . ?
C1 C2 1.387(4) . ?
C7 H7 0.9800 . ?
C11 H11 0.9300 . ?
C11 C12 1.362(4) . ?
C12 C13 1.377(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.365(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.382(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.362(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.358(5) . ?
C4 H4 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C3 -178.8(2) . . . . ?
O3 C9 C14 C13 -176.5(2) . . . . ?
O3 C8 C7 C10 18.8(2) . . . . ?
O3 C8 C7 C6 -99.7(2) . . . . ?
O1 N1 C8 O3 168.0(2) . . . . ?
O1 N1 C8 C7 -74.3(3) . . . . ?
N1 C8 C7 C10 -98.7(2) . . . . ?
N1 C8 C7 C6 142.7(2) . . . . ?
O2 N1 C8 O3 -9.9(3) . . . . ?
O2 N1 C8 C7 107.8(3) . . . . ?
C10 C9 C14 C13 0.6(4) . . . . ?
C10 C11 C12 O4 178.5(3) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C9 O3 C8 N1 99.0(2) . . . . ?
C9 O3 C8 C7 -18.8(3) . . . . ?
C9 C10 C7 C8 -12.1(3) . . . . ?
C9 C10 C7 C6 105.8(2) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C9 C14 C13 O5 -179.3(3) . . . . ?
C9 C14 C13 C12 -0.7(4) . . . . ?
O4 C12 C13 O5 0.8(3) . . . . ?
O4 C12 C13 C14 -178.0(3) . . . . ?
C8 O3 C9 C10 11.0(3) . . . . ?
C8 O3 C9 C14 -171.6(2) . . . . ?
C6 C1 C2 C3 0.4(5) . . . . ?
C6 C5 C4 C3 -0.8(5) . . . . ?
C1 C6 C7 C10 123.5(3) . . . . ?
C1 C6 C7 C8 -125.8(3) . . . . ?
C1 C6 C5 C4 1.9(4) . . . . ?
C1 C2 C3 C4 0.8(5) . . . . ?
C7 C10 C9 O3 1.8(3) . . . . ?
C7 C10 C9 C14 -175.6(2) . . . . ?
C7 C10 C11 C12 173.9(3) . . . . ?
C7 C6 C1 Br1 -1.3(4) . . . . ?
C7 C6 C1 C2 179.5(3) . . . . ?
C7 C6 C5 C4 -179.2(3) . . . . ?
C11 C10 C9 O3 177.6(2) . . . . ?
C11 C10 C9 C14 0.3(4) . . . . ?
C11 C10 C7 C8 172.6(3) . . . . ?
C11 C10 C7 C6 -69.4(3) . . . . ?
C11 C12 C13 O5 178.8(3) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C12 O4 C15 O5 11.9(4) . . . . ?
C13 O5 C15 O4 -11.6(4) . . . . ?
C5 C6 C1 Br1 177.5(2) . . . . ?
C5 C6 C1 C2 -1.7(4) . . . . ?
C5 C6 C7 C10 -55.3(3) . . . . ?
C5 C6 C7 C8 55.4(3) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C15 O5 C13 C12 6.7(4) . . . . ?
C15 O5 C13 C14 -174.5(3) . . . . ?
C15 O4 C12 C11 174.2(3) . . . . ?
C15 O4 C12 C13 -7.9(3) . . . . ?
