#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:20:24 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301776 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/55/1515500.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_1515500
loop_
_publ_author_name
'Khan, Hasan A.'
'Kou, Kevin G. M.'
'Dong, Vy M.'
_publ_section_title
;
 Nitrogen-directed ketone hydroacylation: Enantioselective synthesis of
 benzoxazecinones
;
_journal_issue                   3
_journal_name_full               'Chemical Science'
_journal_page_first              407
_journal_paper_doi               10.1039/c0sc00469c
_journal_volume                  2
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H16 Br N O2'
_chemical_formula_sum            'C17 H16 Br N O2'
_chemical_formula_weight         346.22
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2980(4)
_cell_length_b                   12.0690(4)
_cell_length_c                   16.9434(5)
_cell_measurement_reflns_used    10808
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     1492.37(11)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10808
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    2.758
_exptl_absorpt_correction_T_max  0.720
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.028(11)
_refine_ls_extinction_coef       0.0055(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0403P)²+0.2520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0842
_reflns_number_gt                2684
_reflns_number_total             3332
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c0sc00469c.txt
_cod_data_source_block           k09242a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_database_code               1515500
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br -0.00261(6) -0.48085(2) 0.955305(18) 0.03504(13) Uani 1 1 d .
O1 O 0.4980(3) -0.04290(14) 0.82733(11) 0.0235(4) Uani 1 1 d .
O2 O 0.7716(3) 0.02321(19) 0.81080(18) 0.0419(7) Uani 1 1 d .
N1 N 0.2815(4) 0.1960(2) 0.78144(16) 0.0255(6) Uani 1 1 d .
C1 C 0.6142(4) 0.0436(3) 0.8291(2) 0.0263(7) Uani 1 1 d .
C2 C 0.5610(4) 0.1561(3) 0.85918(19) 0.0226(7) Uani 1 1 d .
C3 C 0.6877(5) 0.1953(3) 0.9144(2) 0.0317(8) Uani 1 1 d .
H3A H 0.7902 0.1504 0.9274 0.038 Uiso 1 1 calc R
C4 C 0.6688(5) 0.2974(3) 0.9510(2) 0.0377(9) Uani 1 1 d .
H4A H 0.7536 0.3211 0.9900 0.045 Uiso 1 1 calc R
C5 C 0.5229(6) 0.3639(3) 0.92902(19) 0.0348(8) Uani 1 1 d .
H5A H 0.5088 0.4348 0.9527 0.042 Uiso 1 1 calc R
C6 C 0.3987(5) 0.3292(2) 0.8738(2) 0.0280(8) Uani 1 1 d .
H6A H 0.3010 0.3773 0.8598 0.034 Uiso 1 1 calc R
C7 C 0.4105(4) 0.2245(2) 0.8368(2) 0.0235(7) Uani 1 1 d .
C8 C 0.3003(5) 0.1028(2) 0.72762(19) 0.0256(7) Uani 1 1 d .
H8A H 0.4319 0.0899 0.7168 0.031 Uiso 1 1 calc R
H8B H 0.2397 0.1210 0.6770 0.031 Uiso 1 1 calc R
C9 C 0.2160(4) -0.0030(2) 0.76115(19) 0.0238(7) Uani 1 1 d .
H9A H 0.0823 0.0073 0.7678 0.029 Uiso 1 1 calc R
H9B H 0.2359 -0.0649 0.7238 0.029 Uiso 1 1 calc R
C10 C 0.3018(4) -0.0311(2) 0.84024(19) 0.0217(7) Uani 1 1 d .
H10A H 0.2773 0.0294 0.8792 0.026 Uiso 1 1 calc R
C11 C 0.1108(5) 0.2598(3) 0.7752(3) 0.0363(9) Uani 1 1 d .
H11A H 0.0624 0.2743 0.8281 0.054 Uiso 1 1 calc R
H11B H 0.0207 0.2173 0.7447 0.054 Uiso 1 1 calc R
H11C H 0.1353 0.3302 0.7484 0.054 Uiso 1 1 calc R
C12 C 0.2334(4) -0.1404(2) 0.87158(18) 0.0210(7) Uani 1 1 d .
C13 C 0.0746(5) -0.1447(3) 0.91556(19) 0.0268(7) Uani 1 1 d .
H13A H 0.0130 -0.0776 0.9280 0.032 Uiso 1 1 calc R
C14 C 0.0020(5) -0.2451(2) 0.94228(17) 0.0267(6) Uani 1 1 d .
H14A H -0.1068 -0.2469 0.9730 0.032 Uiso 1 1 calc R
C15 C 0.0931(5) -0.3417(3) 0.92264(19) 0.0256(7) Uani 1 1 d .
C16 C 0.2523(4) -0.3399(3) 0.8790(2) 0.0282(8) Uani 1 1 d .
H16A H 0.3138 -0.4071 0.8669 0.034 Uiso 1 1 calc R
C17 C 0.3221(5) -0.2401(2) 0.8531(2) 0.0269(7) Uani 1 1 d .
H17A H 0.4311 -0.2390 0.8224 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'
Br Br -0.2901 2.4595 '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
C1 O1 C10 122.7(2)
C7 N1 C8 123.9(3)
C7 N1 C11 120.0(3)
C8 N1 C11 116.1(3)
O2 C1 O1 115.7(3)
O2 C1 C2 120.9(3)
O1 C1 C2 123.1(3)
C3 C2 C7 119.5(3)
C3 C2 C1 111.2(3)
C7 C2 C1 129.2(3)
C4 C3 C2 122.3(3)
C5 C4 C3 118.2(3)
C6 C5 C4 121.0(3)
C5 C6 C7 122.4(3)
N1 C7 C6 119.0(3)
N1 C7 C2 124.4(3)
C6 C7 C2 116.6(3)
N1 C8 C9 112.1(3)
C10 C9 C8 110.4(3)
O1 C10 C12 107.0(2)
O1 C10 C9 107.2(2)
C12 C10 C9 111.7(2)
C13 C12 C17 118.5(3)
C13 C12 C10 120.1(3)
C17 C12 C10 121.3(3)
C12 C13 C14 121.8(3)
C15 C14 C13 118.0(3)
C16 C15 C14 121.4(3)
C16 C15 Br1 118.7(2)
C14 C15 Br1 119.9(2)
C15 C16 C17 119.8(3)
C16 C17 C12 120.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C15 1.902(3)
O1 C1 1.345(4)
O1 C10 1.456(4)
O2 C1 1.215(4)
N1 C7 1.373(4)
N1 C8 1.455(4)
N1 C11 1.468(4)
C1 C2 1.502(4)
C2 C3 1.398(5)
C2 C7 1.425(4)
C3 C4 1.386(5)
C4 C5 1.384(5)
C5 C6 1.368(5)
C6 C7 1.414(4)
C8 C9 1.526(4)
C9 C10 1.517(4)
C10 C12 1.507(4)
C12 C13 1.378(4)
C12 C17 1.403(4)
C13 C14 1.398(4)
C14 C15 1.383(4)
C15 C16 1.377(5)
C16 C17 1.379(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139043028
