#------------------------------------------------------------------------------
#$Date: 2022-05-05 23:36:22 +0300 (Thu, 05 May 2022) $
#$Revision: 274982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/46/7244670.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_7244670
loop_
_publ_author_name
'Goh, Jeffrey'
'Ong, Seng Kheong'
'Tan, Yan Sheng'
'Loh, Teck-Peng'
_publ_section_title
;
 Catalyst-free C--N bond formation under biocompatible reaction conditions
;
_journal_issue                   8
_journal_name_full               'Green Chemistry'
_journal_page_first              3321
_journal_page_last               3325
_journal_paper_doi               10.1039/D2GC00027J
_journal_volume                  24
_journal_year                    2022
_chemical_formula_sum            'C16 H14 Br N O'
_chemical_formula_weight         316.19
_chemical_melting_point          398.6(5)
_chemical_name_systematic
(Z)-3-((4-bromophenyl)amino)-1-phenylbut-2-en-1-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2022-03-16 deposited with the CCDC.	2022-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.963(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.3843(11)
_cell_length_b                   7.1053(12)
_cell_length_c                   15.724(3)
_cell_measurement_reflns_used    4558
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      32.5219
_cell_measurement_theta_min      2.6389
_cell_volume                     700.3(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_publication_material  'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'XT, VERSION 2018/2'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Photon II CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8167
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         32.58
_diffrn_reflns_theta_min         2.64
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Bruker D8 Quest'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.926
_exptl_absorpt_correction_T_max  0.72
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane, Ethyl Acetate'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.622
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0220P)²+0.2735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0621
_refine_ls_wR_factor_ref         0.0660
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2272
_reflns_number_total             2660
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2gc00027j2.cif
_cod_data_source_block           ltp350m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '398.15 - 399.15' was
changed to '398.6(5)' -- the average value was taken and precision
was estimated.

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7244670.cif.
;
_cod_database_code               7244670
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.7829(2) 0.6995(2) 0.23749(9) 0.0192(6) Uani d . P G 0.5 A -1
H H1 0.902857 0.638048 0.271129 0.023000 Uiso calc U P R 0.5 A -1
C C2 0.7547(3) 0.6990(3) 0.14762(9) 0.0221(6) Uani d . P G 0.5 A -1
H H2 0.855336 0.637333 0.119850 0.027000 Uiso calc U P R 0.5 A -1
C C3 0.5792(3) 0.7889(3) 0.09840(7) 0.0235(9) Uani d . P G 0.5 A -1
H H3 0.559896 0.788578 0.036980 0.028000 Uiso calc U P R 0.5 A -1
C C4 0.4319(2) 0.8791(3) 0.13903(9) 0.0207(6) Uani d . P G 0.5 A -1
H H4 0.311976 0.940538 0.105387 0.025000 Uiso calc U P R 0.5 A -1
C C5 0.4601(2) 0.8796(3) 0.22889(9) 0.0169(5) Uani d . P G 0.5 A -1
H H5 0.359494 0.941255 0.256666 0.020000 Uiso calc U P R 0.5 A -1
C C6 0.6356(3) 0.7897(2) 0.27812(7) 0.0137(6) Uani d . P G 0.5 A -1
C C7 0.6761(4) 0.7913(3) 0.37557(15) 0.0144(6) Uani d . P . 0.5 A -1
C C8 0.4998(4) 0.7986(3) 0.41925(15) 0.0140(5) Uani d . P . 0.5 A -1
H H8 0.360077 0.807877 0.385411 0.017000 Uiso calc U P R 0.5 A -1
C C9 0.5223(4) 0.7929(3) 0.50862(16) 0.0136(6) Uani d . P . 0.5 A -1
C C10 0.3271(4) 0.7863(4) 0.54884(16) 0.0169(9) Uani d . P . 0.5 A -1
H H10A 0.357229 0.711295 0.602086 0.025000 Uiso calc U P R 0.5 A -1
H H10B 0.209264 0.728750 0.508090 0.025000 Uiso calc U P R 0.5 A -1
H H10C 0.287514 0.914394 0.562593 0.025000 Uiso calc U P R 0.5 A -1
C C11 0.7802(2) 0.7809(3) 0.64972(6) 0.0127(8) Uani d . P G 0.5 A -1
C C12 0.9574(2) 0.6719(3) 0.68335(9) 0.0147(5) Uani d . P G 0.5 A -1
H H12 1.027779 0.602114 0.645532 0.018000 Uiso calc U P R 0.5 A -1
C C13 1.0318(2) 0.6650(3) 0.77232(9) 0.0162(5) Uani d . P G 0.5 A -1
H H13 1.152895 0.590463 0.795309 0.019000 Uiso calc U P R 0.5 A -1
C C14 0.9289(3) 0.7670(3) 0.82766(6) 0.0148(5) Uani d . P G 0.5 A -1
C C15 0.7516(3) 0.8760(3) 0.79402(9) 0.0174(5) Uani d . P G 0.5 A -1
H H15 0.681280 0.945762 0.831843 0.021000 Uiso calc U P R 0.5 A -1
C C16 0.6773(2) 0.8829(3) 0.70505(9) 0.0169(5) Uani d . P G 0.5 A -1
H H16 0.556161 0.957415 0.682066 0.020000 Uiso calc U P R 0.5 A -1
Br Br1 1.02846(4) 0.7501(3) 0.94801(2) 0.02275(9) Uani d . P . 0.5 A -1
N N1 0.7180(3) 0.7876(3) 0.55861(12) 0.0133(7) Uani d . P . 0.5 A -1
H H1A 0.824009 0.788406 0.530112 0.016000 Uiso calc U P R 0.5 A -1
O O1 0.8670(3) 0.7783(8) 0.41506(11) 0.0191(12) Uani d . P . 0.5 A -1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 120.000000 ?
C1 C2 C3 . . 120.000000 ?
C4 C3 C2 . . 120.000000 ?
C3 C4 C5 . . 120.000000 ?
C6 C5 C4 . . 120.000000 ?
C5 C6 C1 . . 120.000000 ?
C5 C6 C7 . . 121.85(13) ?
C1 C6 C7 . . 118.13(13) ?
O1 C7 C8 . . 122.9(2) ?
O1 C7 C6 . . 117.6(2) ?
C8 C7 C6 . . 119.5(2) ?
C9 C8 C7 . . 123.2(2) ?
N1 C9 C8 . . 120.0(2) ?
N1 C9 C10 . . 120.4(2) ?
C8 C9 C10 . . 119.6(2) ?
C12 C11 C16 . . 120.000000 ?
C12 C11 N1 . . 117.15(13) ?
C16 C11 N1 . . 122.81(13) ?
C11 C12 C13 . . 120.000000 ?
C14 C13 C12 . . 120.000000 ?
C13 C14 C15 . . 120.000000 ?
C13 C14 Br1 . . 119.11(11) ?
C15 C14 Br1 . . 120.87(10) ?
C16 C15 C14 . . 120.000000 ?
C15 C16 C11 . . 120.000000 ?
C9 N1 C11 . . 130.16(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.390000 ?
C1 C6 . 1.390000 ?
C2 C3 . 1.390000 ?
C3 C4 . 1.390000 ?
C4 C5 . 1.390000 ?
C5 C6 . 1.390000 ?
C6 C7 . 1.505(3) ?
C7 O1 . 1.262(3) ?
C7 C8 . 1.427(3) ?
C8 C9 . 1.386(3) ?
C9 N1 . 1.344(3) ?
C9 C10 . 1.502(3) ?
C11 C12 . 1.390000 ?
C11 C16 . 1.390000 ?
C11 N1 . 1.413(2) ?
C12 C13 . 1.390000 ?
C13 C14 . 1.390000 ?
C14 C15 . 1.390000 ?
C14 Br1 . 1.882100 ?
C15 C16 . 1.390000 ?
