#------------------------------------------------------------------------------
#$Date: 2023-01-19 04:05:18 +0200 (Thu, 19 Jan 2023) $
#$Revision: 280428 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/61/7246163.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_7246163
loop_
_publ_author_name
'Guo, Mengping'
'Li, Yingmin'
'Wen, Yongju'
'Shen, Xiuli'
_publ_section_title
;
 Synthesis of aryloxyacetamides from arylboronic acids and
 2-bromoacetonitrile promoted by alkaline solutions of hydrogen peroxide
;
_journal_issue                   4
_journal_name_full               'RSC Advances'
_journal_page_first              2631
_journal_page_last               2634
_journal_paper_doi               10.1039/D2RA07451F
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C8 H9 N O2'
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-21 deposited with the CCDC.	2023-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                93.647(5)
_cell_angle_beta                 95.000(5)
_cell_angle_gamma                103.040(5)
_cell_formula_units_Z            4
_cell_length_a                   6.1970(4)
_cell_length_b                   9.2995(6)
_cell_length_c                   13.4406(8)
_cell_measurement_reflns_used    3461
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      29.3150
_cell_measurement_theta_min      2.5870
_cell_volume                     748.95(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  61.00   1.00    1.01    --  -11.74  57.00 -30.00  101
  2  ω    -85.00  16.00   1.00    1.01    --  -11.74 -57.00-180.00  101
  3  ω    -21.00  88.00   1.00    1.01    --   11.90  77.00  90.00  109
  4  ω    -85.00 -41.00   1.00    1.01    --  -11.74 -57.00 -60.00   44
  5  ω    -20.00  25.00   1.00    1.01    --   11.90 -99.00  90.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0416516000
_diffrn_orient_matrix_UB_12      -0.0640211000
_diffrn_orient_matrix_UB_13      0.0073117000
_diffrn_orient_matrix_UB_21      -0.0787141000
_diffrn_orient_matrix_UB_22      -0.0402668000
_diffrn_orient_matrix_UB_23      -0.0391738000
_diffrn_orient_matrix_UB_31      0.0776188000
_diffrn_orient_matrix_UB_32      0.0213291000
_diffrn_orient_matrix_UB_33      -0.0352007000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6792
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         2.256
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.056
_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         2634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0420
_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)+(0.0512P)²+0.1528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1058
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2298
_reflns_number_total             2634
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra07451f2.cif
_cod_data_source_block           1_3
_cod_database_code               7246163
_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.
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7B(H7BA,H7BB), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C6B(H6B), C4(H4), C6(H6), C1(H1), C2B(H2B), C3(H3), C5B(H5B), C2(H2),
 C4B(H4B), C3B(H3B)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N1B(H1BA,H1BB)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.355
_oxdiff_exptl_absorpt_empirical_full_min 0.629
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.41639(17) 0.70750(11) 0.28521(7) 0.0226(3) Uani 1 1 d . . . . .
O1B O 0.39892(17) 0.19122(11) 0.27846(7) 0.0221(3) Uani 1 1 d . . . . .
O2 O 0.22085(17) 0.43785(12) 0.45012(8) 0.0260(3) Uani 1 1 d . . . . .
O2B O 0.28539(18) 0.09927(12) 0.52280(7) 0.0293(3) Uani 1 1 d . . . . .
N1 N 0.1244(2) 0.65229(14) 0.41896(9) 0.0244(3) Uani 1 1 d . . . . .
H1A H 0.016777 0.636044 0.456137 0.029 Uiso 1 1 calc R . . . .
H1B H 0.151298 0.731901 0.388394 0.029 Uiso 1 1 calc R . . . .
N1B N 0.0814(2) 0.03085(15) 0.37207(9) 0.0276(3) Uani 1 1 d . . . . .
H1BA H -0.032998 -0.016107 0.398199 0.033 Uiso 1 1 calc R . . . .
H1BB H 0.076875 0.034046 0.308132 0.033 Uiso 1 1 calc R . . . .
C5 C 0.5895(2) 0.76046(16) 0.22970(10) 0.0192(3) Uani 1 1 d . . . . .
C1B C 0.5662(3) 0.25142(16) 0.22166(10) 0.0195(3) Uani 1 1 d . . . . .
C6B C 0.7907(3) 0.29189(16) 0.25716(11) 0.0219(4) Uani 1 1 d . . . . .
H6B H 0.836764 0.283818 0.323881 0.026 Uiso 1 1 calc R . . . .
C8 C 0.2490(2) 0.55451(17) 0.40875(10) 0.0210(3) Uani 1 1 d . . . . .
C4 C 0.5788(3) 0.88842(16) 0.18298(11) 0.0224(4) Uani 1 1 d . . . . .
H4 H 0.461018 0.933344 0.190988 0.027 Uiso 1 1 calc R . . . .
C6 C 0.7649(3) 0.69306(16) 0.21729(10) 0.0218(3) Uani 1 1 d . . . . .
H6 H 0.771900 0.607085 0.247910 0.026 Uiso 1 1 calc R . . . .
C1 C 0.9299(3) 0.75526(17) 0.15871(11) 0.0243(4) Uani 1 1 d . . . . .
H1 H 1.047793 0.710494 0.150481 0.029 Uiso 1 1 calc R . . . .
C2B C 0.4972(3) 0.26910(17) 0.12257(11) 0.0237(4) Uani 1 1 d . . . . .
H2B H 0.346453 0.244096 0.099480 0.028 Uiso 1 1 calc R . . . .
C3 C 0.7440(3) 0.94855(17) 0.12461(11) 0.0245(4) Uani 1 1 d . . . . .
H3 H 0.736395 1.033789 0.093194 0.029 Uiso 1 1 calc R . . . .
C8B C 0.2651(3) 0.09849(16) 0.43052(11) 0.0223(4) Uani 1 1 d . . . . .
C7B C 0.4640(3) 0.17396(17) 0.38067(10) 0.0223(4) Uani 1 1 d . . . . .
H7BA H 0.529657 0.270369 0.415849 0.027 Uiso 1 1 calc R . . . .
H7BB H 0.575206 0.115381 0.383931 0.027 Uiso 1 1 calc R . . . .
C7 C 0.4414(3) 0.59138(16) 0.34627(10) 0.0212(3) Uani 1 1 d . . . . .
H7A H 0.579897 0.621819 0.389840 0.025 Uiso 1 1 calc R . . . .
H7B H 0.447737 0.504117 0.304102 0.025 Uiso 1 1 calc R . . . .
C5B C 0.9454(3) 0.34466(17) 0.19133(11) 0.0255(4) Uani 1 1 d . . . . .
H5B H 1.096238 0.369744 0.214212 0.031 Uiso 1 1 calc R . . . .
C2 C 0.9212(3) 0.88259(17) 0.11256(11) 0.0250(4) Uani 1 1 d . . . . .
H2 H 1.032789 0.923788 0.073806 0.030 Uiso 1 1 calc R . . . .
C4B C 0.8794(3) 0.36051(17) 0.09269(11) 0.0275(4) Uani 1 1 d . . . . .
H4B H 0.984799 0.395273 0.049366 0.033 Uiso 1 1 calc R . . . .
C3B C 0.6537(3) 0.32398(17) 0.05870(11) 0.0270(4) Uani 1 1 d . . . . .
H3B H 0.607689 0.336494 -0.007264 0.032 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'
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
C5 O1 C7 116.55(11) . . ?
C1B O1B C7B 116.82(11) . . ?
O1 C5 C4 115.77(13) . . ?
O1 C5 C6 124.17(13) . . ?
C6 C5 C4 120.05(14) . . ?
O1B C1B C6B 124.16(13) . . ?
O1B C1B C2B 115.50(13) . . ?
C6B C1B C2B 120.34(14) . . ?
C1B C6B C5B 118.93(14) . . ?
O2 C8 N1 123.82(14) . . ?
O2 C8 C7 118.28(13) . . ?
N1 C8 C7 117.85(13) . . ?
C3 C4 C5 119.81(14) . . ?
C5 C6 C1 119.39(14) . . ?
C2 C1 C6 120.92(14) . . ?
C3B C2B C1B 119.76(15) . . ?
C4 C3 C2 120.51(14) . . ?
O2B C8B N1B 124.09(14) . . ?
O2B C8B C7B 117.99(13) . . ?
N1B C8B C7B 117.87(13) . . ?
O1B C7B C8B 110.33(12) . . ?
O1 C7 C8 110.30(12) . . ?
C4B C5B C6B 121.25(15) . . ?
C1 C2 C3 119.31(14) . . ?
C5B C4B C3B 119.33(15) . . ?
C2B C3B C4B 120.33(14) . . ?
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
O1 C5 1.3777(18) . ?
O1 C7 1.4247(17) . ?
O1B C1B 1.3790(18) . ?
O1B C7B 1.4270(17) . ?
O2 C8 1.2348(18) . ?
O2B C8B 1.2351(17) . ?
N1 C8 1.3270(19) . ?
N1B C8B 1.3295(19) . ?
C5 C4 1.392(2) . ?
C5 C6 1.388(2) . ?
C1B C6B 1.389(2) . ?
C1B C2B 1.394(2) . ?
C6B C5B 1.391(2) . ?
C8 C7 1.507(2) . ?
C4 C3 1.383(2) . ?
C6 C1 1.390(2) . ?
C1 C2 1.381(2) . ?
C2B C3B 1.384(2) . ?
C3 C2 1.389(2) . ?
C8B C7B 1.508(2) . ?
C5B C4B 1.380(2) . ?
C4B C3B 1.391(2) . ?
