#------------------------------------------------------------------------------
#$Date: 2023-11-06 10:18:34 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287404 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/95/7159583.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_7159583
loop_
_publ_author_name
'Yan, Maying'
'Xiao, Lei'
'Xiong, Jiangkun'
'Jin, Lvnan'
'Stephan, Douglas W.'
'Guo, Jing'
_publ_section_title
;
 Borane catalyzed transesterification of tert-butyl esters using
 α-aryl α-diazoesters.
;
_journal_issue                   41
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8279
_journal_page_last               8283
_journal_paper_doi               10.1039/d3ob01548c
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C18 H15 Br O4'
_chemical_formula_sum            'C18 H15 Br O4'
_chemical_formula_weight         375.21
_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
_audit_creation_date             2023-08-31
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-09-04 deposited with the CCDC.	2023-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                76.2280(10)
_cell_angle_beta                 82.9630(10)
_cell_angle_gamma                83.7500(10)
_cell_formula_units_Z            2
_cell_length_a                   5.8727(2)
_cell_length_b                   9.1764(3)
_cell_length_c                   15.6457(5)
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      2.92
_cell_volume                     809.96(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21478
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.468
_diffrn_reflns_theta_min         2.923
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.616
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6043
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1168 before and 0.0526 after correction.
The Ratio of minimum to maximum transmission is 0.8024.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.849
_refine_diff_density_min         -0.863
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0292
_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)+(0.0182P)²+0.7806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0693
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2765
_reflns_number_total             2893
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01548c2.cif
_cod_data_source_block           f1
_cod_depositor_comments
'Adding full bibliography for 7159583--7159585.cif.'
_cod_database_code               7159583
_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   0.965
_shelx_estimated_absorpt_t_min   0.899
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C5(H5), C11(H11), C18(H18), C3(H3), C2(H2), C14(H14), C16(H16),
 C17(H17), C6(H6), C15(H15)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Br1 Br 0.39042(5) 0.18991(3) 0.03245(2) 0.04622(11) Uani 1 1 d . . . . .
O3 O 0.4941(2) 0.58635(15) 0.33292(8) 0.0267(3) Uani 1 1 d . . . . .
O2 O 0.5968(3) 0.84299(16) 0.20912(10) 0.0374(3) Uani 1 1 d . . . . .
O1 O 0.9398(2) 0.73195(15) 0.17088(10) 0.0360(3) Uani 1 1 d . . . . .
O4 O 0.7301(2) 0.68742(17) 0.40163(10) 0.0350(3) Uani 1 1 d . . . . .
C8 C 0.7300(3) 0.7344(2) 0.21375(12) 0.0238(4) Uani 1 1 d . . . . .
C4 C 0.6163(3) 0.4825(2) 0.20795(12) 0.0231(4) Uani 1 1 d . . . . .
C9 C 0.6842(3) 0.5755(2) 0.26666(12) 0.0239(4) Uani 1 1 d . . . . .
H9 H 0.824317 0.525675 0.295451 0.029 Uiso 1 1 calc R U . . .
C12 C 0.3367(3) 0.7665(2) 0.51197(12) 0.0257(4) Uani 1 1 d . . . . .
H12 H 0.481373 0.802369 0.513791 0.031 Uiso 1 1 calc R U . . .
C13 C 0.1462(3) 0.8137(2) 0.57152(12) 0.0239(4) Uani 1 1 d . . . . .
C5 C 0.7514(3) 0.3542(2) 0.19529(13) 0.0295(4) Uani 1 1 d . . . . .
H5 H 0.890118 0.325592 0.222762 0.035 Uiso 1 1 calc R U . . .
C11 C 0.3311(3) 0.6791(2) 0.45541(12) 0.0267(4) Uani 1 1 d . . . . .
H11 H 0.194371 0.634370 0.452854 0.032 Uiso 1 1 calc R U . . .
C18 C 0.1662(3) 0.9388(2) 0.60565(12) 0.0278(4) Uani 1 1 d . . . . .
H18 H 0.304351 0.988408 0.591460 0.033 Uiso 1 1 calc R U . . .
C3 C 0.4143(3) 0.5239(2) 0.16700(13) 0.0296(4) Uani 1 1 d . . . . .
H3 H 0.321738 0.611869 0.175507 0.036 Uiso 1 1 calc R U . . .
C10 C 0.5405(3) 0.6532(2) 0.39694(12) 0.0262(4) Uani 1 1 d . . . . .
C2 C 0.3467(4) 0.4389(2) 0.11412(14) 0.0324(4) Uani 1 1 d . . . . .
H2 H 0.208857 0.467479 0.086084 0.039 Uiso 1 1 calc R U . . .
C14 C -0.0569(3) 0.7406(2) 0.59510(12) 0.0272(4) Uani 1 1 d . . . . .
H14 H -0.074432 0.655290 0.572754 0.033 Uiso 1 1 calc R U . . .
C16 C -0.2115(4) 0.9184(2) 0.68287(13) 0.0322(4) Uani 1 1 d . . . . .
H16 H -0.333589 0.954086 0.720359 0.039 Uiso 1 1 calc R U . . .
C1 C 0.4841(4) 0.3110(2) 0.10284(13) 0.0310(4) Uani 1 1 d . . . . .
C17 C -0.0118(4) 0.9916(2) 0.65975(13) 0.0317(4) Uani 1 1 d . . . . .
H17 H 0.003153 1.078397 0.681072 0.038 Uiso 1 1 calc R U . . .
C6 C 0.6847(4) 0.2679(2) 0.14271(14) 0.0350(5) Uani 1 1 d . . . . .
H6 H 0.776420 0.179622 0.134215 0.042 Uiso 1 1 calc R U . . .
C15 C -0.2323(3) 0.7920(2) 0.65081(13) 0.0305(4) Uani 1 1 d . . . . .
H15 H -0.368386 0.740427 0.667343 0.037 Uiso 1 1 calc R U . . .
C7 C 1.0112(4) 0.8739(2) 0.11723(16) 0.0411(5) Uani 1 1 d . . . . .
H7A H 1.140484 0.855218 0.074226 0.062 Uiso 1 1 calc R U . . .
H7B H 1.059058 0.933461 0.155245 0.062 Uiso 1 1 calc R U . . .
H7C H 0.882337 0.929355 0.085859 0.062 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O3 C9 114.01(14) . . ?
C8 O1 C7 116.57(15) . . ?
O2 C8 O1 124.92(17) . . ?
O2 C8 C9 125.69(17) . . ?
O1 C8 C9 109.35(15) . . ?
C5 C4 C9 120.65(17) . . ?
C5 C4 C3 119.48(18) . . ?
C3 C4 C9 119.86(16) . . ?
O3 C9 C8 108.53(14) . . ?
O3 C9 C4 107.46(14) . . ?
O3 C9 H9 110.0 . . ?
C8 C9 H9 110.0 . . ?
C4 C9 C8 110.84(15) . . ?
C4 C9 H9 110.0 . . ?
C13 C12 H12 116.2 . . ?
C11 C12 H12 116.2 . . ?
C11 C12 C13 127.63(18) . . ?
C18 C13 C12 118.60(17) . . ?
C18 C13 C14 118.32(18) . . ?
C14 C13 C12 123.07(17) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.13(19) . . ?
C6 C5 H5 119.9 . . ?
C12 C11 H11 120.6 . . ?
C12 C11 C10 118.89(18) . . ?
C10 C11 H11 120.6 . . ?
C13 C18 H18 119.5 . . ?
C17 C18 C13 121.06(18) . . ?
C17 C18 H18 119.5 . . ?
C4 C3 H3 119.6 . . ?
C2 C3 C4 120.84(18) . . ?
C2 C3 H3 119.6 . . ?
O3 C10 C11 111.13(16) . . ?
O4 C10 O3 122.41(17) . . ?
O4 C10 C11 126.44(18) . . ?
C3 C2 H2 120.7 . . ?
C3 C2 C1 118.56(19) . . ?
C1 C2 H2 120.7 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.32(18) . . ?
C15 C14 H14 119.8 . . ?
C17 C16 H16 120.3 . . ?
C17 C16 C15 119.45(19) . . ?
C15 C16 H16 120.3 . . ?
C2 C1 Br1 119.20(16) . . ?
C6 C1 Br1 119.18(16) . . ?
C6 C1 C2 121.60(19) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 C18 120.17(19) . . ?
C16 C17 H17 119.9 . . ?
C5 C6 H6 120.3 . . ?
C1 C6 C5 119.39(19) . . ?
C1 C6 H6 120.3 . . ?
C14 C15 C16 120.66(19) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
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 1.901(2) . ?
O3 C9 1.440(2) . ?
O3 C10 1.360(2) . ?
O2 C8 1.192(2) . ?
O1 C8 1.330(2) . ?
O1 C7 1.446(2) . ?
O4 C10 1.205(2) . ?
C8 C9 1.530(3) . ?
C4 C9 1.506(3) . ?
C4 C5 1.387(3) . ?
C4 C3 1.390(3) . ?
C9 H9 1.0000 . ?
C12 H12 0.9500 . ?
C12 C13 1.462(3) . ?
C12 C11 1.333(3) . ?
C13 C18 1.398(3) . ?
C13 C14 1.399(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.473(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.383(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.381(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.384(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(3) . ?
C16 C15 1.391(3) . ?
C1 C6 1.376(3) . ?
C17 H17 0.9500 . ?
C6 H6 0.9500 . ?
C15 H15 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
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 C6 C5 -178.86(15) . . . . ?
O2 C8 C9 O3 -20.1(3) . . . . ?
O2 C8 C9 C4 97.7(2) . . . . ?
O1 C8 C9 O3 162.05(15) . . . . ?
O1 C8 C9 C4 -80.17(19) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C4 C3 C2 C1 0.1(3) . . . . ?
C9 O3 C10 O4 -6.3(3) . . . . ?
C9 O3 C10 C11 172.33(15) . . . . ?
C9 C4 C5 C6 178.60(18) . . . . ?
C9 C4 C3 C2 -178.87(18) . . . . ?
C12 C13 C18 C17 177.69(17) . . . . ?
C12 C13 C14 C15 -179.09(17) . . . . ?
C12 C11 C10 O3 -168.51(17) . . . . ?
C12 C11 C10 O4 10.1(3) . . . . ?
C13 C12 C11 C10 176.06(17) . . . . ?
C13 C18 C17 C16 1.7(3) . . . . ?
C13 C14 C15 C16 1.2(3) . . . . ?
C5 C4 C9 O3 -124.12(18) . . . . ?
C5 C4 C9 C8 117.45(19) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C11 C12 C13 C18 -161.00(19) . . . . ?
C11 C12 C13 C14 18.1(3) . . . . ?
C18 C13 C14 C15 0.0(3) . . . . ?
C3 C4 C9 O3 54.9(2) . . . . ?
C3 C4 C9 C8 -63.6(2) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C3 C2 C1 Br1 178.59(15) . . . . ?
C3 C2 C1 C6 -0.1(3) . . . . ?
C10 O3 C9 C8 -67.12(19) . . . . ?
C10 O3 C9 C4 172.96(14) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C14 C13 C18 C17 -1.5(3) . . . . ?
C17 C16 C15 C14 -1.0(3) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C7 O1 C8 O2 2.1(3) . . . . ?
C7 O1 C8 C9 179.97(17) . . . . ?
