#------------------------------------------------------------------------------
#$Date: 2019-11-10 05:51:03 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225624 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/54/4515469.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_4515469
loop_
_publ_author_name
'Featherston, Aaron L.'
'Shugrue, Christopher R.'
'Mercado, Brandon Q.'
'Miller, Scott J.'
_publ_section_title
;
 Phosphothreonine (pThr)-Based Multifunctional Peptide Catalysis for
 Asymmetric Baeyer-Villiger Oxidations of Cyclobutanones.
;
_journal_issue                   1
_journal_name_full               'ACS catalysis'
_journal_page_first              242
_journal_page_last               252
_journal_paper_doi               10.1021/acscatal.8b04132
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H14 Br N O4'
_chemical_formula_sum            'C17 H14 Br N O4'
_chemical_formula_weight         376.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.045(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.7393(8)
_cell_length_b                   5.21210(10)
_cell_length_c                   14.2943(4)
_cell_measurement_reflns_used    14935
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      66.6460
_cell_measurement_theta_min      3.4940
_cell_volume                     1691.76(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28915
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         3.569
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    3.482
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       Plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.939
_refine_diff_density_min         -0.944
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
; 
 Flack x determined using 1201 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.125(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2985
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0534P)²+3.1917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2858
_reflns_number_total             2985
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs8b04132_si_005.cif
_cod_data_source_block           007b-18036
_cod_original_sg_symbol_H-M      'I 2'
_cod_database_code               4515469
_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. 
;
_shelx_estimated_absorpt_t_min   0.768
_shelx_estimated_absorpt_t_max   0.934
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-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
Br1 Br 0.69148(3) 0.76956(12) 0.05329(3) 0.0470(2) Uani 1 1 d . .
O1 O 0.62393(13) 0.2260(7) 0.5765(2) 0.0271(8) Uani 1 1 d . .
O2 O 0.68386(15) 0.5533(7) 0.5385(2) 0.0296(8) Uani 1 1 d . .
O3 O 0.49860(15) 0.9259(7) 0.7055(3) 0.0333(8) Uani 1 1 d . .
O4 O 0.44396(16) 0.8433(8) 0.5752(3) 0.0417(10) Uani 1 1 d . .
N1 N 0.63188(17) 0.3108(9) 0.4268(3) 0.0279(10) Uani 1 1 d . .
H1 H 0.6084 0.1768 0.4220 0.033 Uiso 1 1 calc R U
C1 C 0.64320(18) 0.2503(13) 0.6717(3) 0.0245(9) Uani 1 1 d . .
C2 C 0.6844(2) 0.0733(10) 0.7055(3) 0.0274(10) Uani 1 1 d . .
H2 H 0.7000 -0.0508 0.6650 0.033 Uiso 1 1 calc R U
C3 C 0.7023(2) 0.0805(11) 0.7999(4) 0.0298(11) Uani 1 1 d . .
H3 H 0.7307 -0.0390 0.8244 0.036 Uiso 1 1 calc R U
C4 C 0.67919(18) 0.2598(14) 0.8575(3) 0.0291(9) Uani 1 1 d . .
H4 H 0.6910 0.2628 0.9222 0.035 Uiso 1 1 calc R U
C5 C 0.6383(2) 0.4379(10) 0.8214(3) 0.0300(11) Uani 1 1 d . .
H5 H 0.6233 0.5640 0.8617 0.036 Uiso 1 1 calc R U
C6 C 0.6189(2) 0.4347(10) 0.7269(3) 0.0274(11) Uani 1 1 d . .
C7 C 0.5771(2) 0.6352(10) 0.6859(3) 0.0292(11) Uani 1 1 d . .
H7 H 0.6000 0.7505 0.6453 0.035 Uiso 1 1 calc R U
C8 C 0.5224(2) 0.5456(11) 0.6281(4) 0.0357(12) Uani 1 1 d . .
H8A H 0.5320 0.5002 0.5633 0.043 Uiso 1 1 calc R U
H8B H 0.5037 0.3965 0.6575 0.043 Uiso 1 1 calc R U
C9 C 0.48362(19) 0.7803(14) 0.6297(3) 0.0310(10) Uani 1 1 d . .
C10 C 0.5484(2) 0.8022(13) 0.7580(3) 0.0342(12) Uani 1 1 d . .
H10A H 0.5344 0.6964 0.8099 0.041 Uiso 1 1 calc R U
H10B H 0.5765 0.9320 0.7842 0.041 Uiso 1 1 calc R U
C11 C 0.6505(2) 0.3840(10) 0.5157(3) 0.0267(10) Uani 1 1 d . .
C12 C 0.6465(2) 0.4275(10) 0.3434(3) 0.0258(10) Uani 1 1 d . .
C13 C 0.6243(2) 0.3155(11) 0.2597(3) 0.0310(12) Uani 1 1 d . .
H13 H 0.5999 0.1677 0.2622 0.037 Uiso 1 1 calc R U
C14 C 0.6370(3) 0.4153(12) 0.1744(4) 0.0367(12) Uani 1 1 d . .
H14 H 0.6220 0.3363 0.1181 0.044 Uiso 1 1 calc R U
C15 C 0.6716(2) 0.6305(11) 0.1710(4) 0.0325(11) Uani 1 1 d . .
C16 C 0.6935(2) 0.7504(14) 0.2524(3) 0.0325(10) Uani 1 1 d . .
H16 H 0.7169 0.9009 0.2489 0.039 Uiso 1 1 calc R U
C17 C 0.6810(2) 0.6488(11) 0.3383(4) 0.0297(11) Uani 1 1 d . .
H17 H 0.6959 0.7296 0.3943 0.036 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 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C11 O1 C1 115.8(4)
C9 O3 C10 108.5(4)
C11 N1 C12 126.5(4)
C11 N1 H1 116.8
C12 N1 H1 116.8
C6 C1 C2 123.3(4)
C6 C1 O1 120.1(4)
C2 C1 O1 116.5(5)
C1 C2 C3 118.7(5)
C1 C2 H2 120.6
C3 C2 H2 120.6
C4 C3 C2 120.0(5)
C4 C3 H3 120.0
C2 C3 H3 120.0
C3 C4 C5 120.1(4)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C6 121.3(5)
C4 C5 H5 119.4
C6 C5 H5 119.4
C1 C6 C5 116.5(4)
C1 C6 C7 121.6(4)
C5 C6 C7 121.7(5)
C6 C7 C10 114.6(4)
C6 C7 C8 118.4(5)
C10 C7 C8 100.1(4)
C6 C7 H7 107.7
C10 C7 H7 107.7
C8 C7 H7 107.7
C9 C8 C7 101.7(4)
C9 C8 H8A 111.4
C7 C8 H8A 111.4
C9 C8 H8B 111.4
C7 C8 H8B 111.4
H8A C8 H8B 109.3
O4 C9 O3 120.9(6)
O4 C9 C8 129.0(6)
O3 C9 C8 110.2(4)
O3 C10 C7 104.5(4)
O3 C10 H10A 110.9
C7 C10 H10A 110.9
O3 C10 H10B 110.9
C7 C10 H10B 110.9
H10A C10 H10B 108.9
O2 C11 O1 124.5(4)
O2 C11 N1 128.1(5)
O1 C11 N1 107.3(4)
N1 C12 C17 124.3(4)
N1 C12 C13 117.1(5)
C17 C12 C13 118.6(5)
C14 C13 C12 121.1(5)
C14 C13 H13 119.4
C12 C13 H13 119.4
C13 C14 C15 119.3(5)
C13 C14 H14 120.3
C15 C14 H14 120.3
C14 C15 C16 121.3(5)
C14 C15 Br1 120.3(4)
C16 C15 Br1 118.4(4)
C17 C16 C15 119.4(6)
C17 C16 H16 120.3
C15 C16 H16 120.3
C16 C17 C12 120.3(5)
C16 C17 H17 119.8
C12 C17 H17 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C15 1.909(5)
O1 C11 1.362(6)
O1 C1 1.413(5)
O2 C11 1.198(6)
O3 C9 1.352(7)
O3 C10 1.474(6)
O4 C9 1.205(6)
N1 C11 1.371(6)
N1 C12 1.395(7)
N1 H1 0.8800
C1 C6 1.377(8)
C1 C2 1.383(8)
C2 C3 1.388(7)
C2 H2 0.9500
C3 C4 1.369(8)
C3 H3 0.9500
C4 C5 1.393(8)
C4 H4 0.9500
C5 C6 1.399(7)
C5 H5 0.9500
C6 C7 1.510(7)
C7 C10 1.523(8)
C7 C8 1.529(7)
C7 H7 1.0000
C8 C9 1.509(8)
C8 H8A 0.9900
C8 H8B 0.9900
C10 H10A 0.9900
C10 H10B 0.9900
C12 C17 1.399(8)
C12 C13 1.401(7)
C13 C14 1.372(8)
C13 H13 0.9500
C14 C15 1.372(8)
C14 H14 0.9500
C15 C16 1.389(7)
C16 C17 1.381(7)
C16 H16 0.9500
C17 H17 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O4 0.88 2.11 2.984(6) 173.7 2_646
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
C11 O1 C1 C6 84.9(5)
C11 O1 C1 C2 -98.4(6)
C6 C1 C2 C3 0.0(8)
O1 C1 C2 C3 -176.6(4)
C1 C2 C3 C4 0.2(8)
C2 C3 C4 C5 -1.0(8)
C3 C4 C5 C6 1.5(8)
C2 C1 C6 C5 0.4(8)
O1 C1 C6 C5 176.9(4)
C2 C1 C6 C7 175.9(5)
O1 C1 C6 C7 -7.6(8)
C4 C5 C6 C1 -1.2(8)
C4 C5 C6 C7 -176.7(5)
C1 C6 C7 C10 172.6(5)
C5 C6 C7 C10 -12.2(7)
C1 C6 C7 C8 54.8(7)
C5 C6 C7 C8 -130.0(5)
C6 C7 C8 C9 161.1(4)
C10 C7 C8 C9 35.9(5)
C10 O3 C9 O4 -179.5(5)
C10 O3 C9 C8 1.0(6)
C7 C8 C9 O4 156.3(6)
C7 C8 C9 O3 -24.3(6)
C9 O3 C10 C7 23.1(6)
C6 C7 C10 O3 -164.3(4)
C8 C7 C10 O3 -36.5(5)
C1 O1 C11 O2 -7.4(7)
C1 O1 C11 N1 172.4(4)
C12 N1 C11 O2 -2.8(9)
C12 N1 C11 O1 177.4(4)
C11 N1 C12 C17 -3.1(8)
C11 N1 C12 C13 177.8(5)
N1 C12 C13 C14 -179.2(5)
C17 C12 C13 C14 1.7(8)
C12 C13 C14 C15 -0.8(8)
C13 C14 C15 C16 -0.6(9)
C13 C14 C15 Br1 178.6(4)
C14 C15 C16 C17 1.0(8)
Br1 C15 C16 C17 -178.2(4)
C15 C16 C17 C12 -0.1(8)
N1 C12 C17 C16 179.7(5)
C13 C12 C17 C16 -1.2(8)
