#------------------------------------------------------------------------------
#$Date: 2021-08-26 04:25:24 +0300 (Thu, 26 Aug 2021) $
#$Revision: 268224 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/34/7243449.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_7243449
loop_
_publ_author_name
'Chinen, Beatrice L.'
'Hyvl, Jakub'
'Brayton, Daniel F.'
'Riek, Matthew M.'
'Yoshida, Wesley Y.'
'Chapp, Timothy W.'
'Rheingold, Arnold L.'
'Cain, Matthew F.'
_publ_section_title
;
 Trimerization and cyclization of reactive P-functionalities confined
 within OCO pincers
;
_journal_issue                   46
_journal_name_full               'RSC Advances'
_journal_page_first              28602
_journal_page_last               28613
_journal_paper_doi               10.1039/D1RA05926B
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C26 H29 Br O2'
_chemical_formula_sum            'C26 H29 Br O2'
_chemical_formula_weight         453.40
_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             2017-06-22
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2021-07-08 deposited with the CCDC.	2021-08-10 downloaded from the CCDC.
;
_cell_angle_alpha                101.293(4)
_cell_angle_beta                 100.471(5)
_cell_angle_gamma                94.032(6)
_cell_formula_units_Z            2
_cell_length_a                   7.4093(13)
_cell_length_b                   8.2707(14)
_cell_length_c                   18.706(3)
_cell_measurement_reflns_used    4237
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.285
_cell_measurement_theta_min      2.526
_cell_volume                     1098.7(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX CCD'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11445
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.372
_diffrn_reflns_theta_min         2.813
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.890
_exptl_absorpt_correction_T_max  0.2590
_exptl_absorpt_correction_T_min  0.2112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0637 before and 0.0404 after correction. The Ratio of minimum to maximum transmission is 0.8154. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_refine_diff_density_max         2.092
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0679P)²+1.2910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1231
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3478
_reflns_number_total             3990
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra05926b2.cif
_cod_data_source_block           cain57_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

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.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7243449
_shelx_shelxl_version_number     2016/6
_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   0.620
_shelx_estimated_absorpt_t_min   0.583
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C5(H5), C20(H20), C11(H11), C3(H3), C4(H4), C22(H22)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C26(H26A,H26B,
 H26C), C25(H25A,H25B,H25C), C16(H16A,H16B,H16C)
;
_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 0.20580(5) 0.14291(4) 0.50604(2) 0.02226(15) Uani 1 1 d . . . . .
O1 O 0.3198(3) 0.4135(3) 0.68291(13) 0.0170(5) Uani 1 1 d . . . . .
O2 O 0.1719(3) 0.2549(3) 0.32476(13) 0.0177(5) Uani 1 1 d . . . . .
C9 C 0.4142(5) 0.3949(5) 0.75211(19) 0.0172(7) Uani 1 1 d . . . . .
C18 C 0.0838(5) 0.1614(4) 0.25527(19) 0.0172(7) Uani 1 1 d . . . . .
C13 C 0.5742(5) 0.5178(5) 0.8762(2) 0.0239(8) Uani 1 1 d . . . . .
H13 H 0.620182 0.613324 0.914302 0.029 Uiso 1 1 calc R . . . .
C24 C 0.0386(5) 0.4310(5) 0.2127(2) 0.0234(8) Uani 1 1 d . . . . .
H24A H -0.058209 0.473080 0.238346 0.035 Uiso 1 1 calc GR . . . .
H24B H 0.026436 0.466055 0.165086 0.035 Uiso 1 1 calc GR . . . .
H24C H 0.160003 0.475318 0.243638 0.035 Uiso 1 1 calc GR . . . .
C14 C 0.4820(5) 0.5373(5) 0.8068(2) 0.0189(8) Uani 1 1 d . . . . .
C10 C 0.4363(5) 0.2357(5) 0.7652(2) 0.0204(8) Uani 1 1 d . . . . .
C17 C 0.4616(5) 0.7078(5) 0.7915(2) 0.0243(8) Uani 1 1 d . . . . .
H17A H 0.557331 0.737887 0.765056 0.036 Uiso 1 1 calc GR . . . .
H17B H 0.474584 0.788327 0.838615 0.036 Uiso 1 1 calc GR . . . .
H17C H 0.339500 0.708181 0.760756 0.036 Uiso 1 1 calc GR . . . .
C19 C 0.0193(5) 0.2451(5) 0.1989(2) 0.0187(8) Uani 1 1 d . . . . .
C2 C 0.3472(5) 0.4811(4) 0.56610(19) 0.0143(7) Uani 1 1 d . . . . .
C12 C 0.6002(5) 0.3620(5) 0.8905(2) 0.0263(9) Uani 1 1 d . . . . .
C21 C -0.0882(5) -0.0224(5) 0.1154(2) 0.0245(9) Uani 1 1 d . . . . .
C6 C 0.1519(5) 0.4236(4) 0.44098(19) 0.0152(7) Uani 1 1 d . . . . .
C5 C 0.1739(5) 0.5923(4) 0.44172(19) 0.0181(8) Uani 1 1 d . . . . .
H5 H 0.113927 0.632033 0.400246 0.022 Uiso 1 1 calc R . . . .
C20 C -0.0663(5) 0.1495(5) 0.1296(2) 0.0227(8) Uani 1 1 d . . . . .
H20 H -0.111193 0.203838 0.090686 0.027 Uiso 1 1 calc R . . . .
C23 C 0.0678(5) -0.0109(5) 0.2425(2) 0.0203(8) Uani 1 1 d . . . . .
C8 C 0.0438(5) 0.3069(4) 0.37228(19) 0.0175(7) Uani 1 1 d . . . . .
H8A H -0.016395 0.209506 0.385699 0.021 Uiso 1 1 calc R . . . .
H8B H -0.053042 0.363416 0.346262 0.021 Uiso 1 1 calc R . . . .
C11 C 0.5307(5) 0.2227(5) 0.8346(2) 0.0250(9) Uani 1 1 d . . . . .
H11 H 0.548286 0.115773 0.844254 0.030 Uiso 1 1 calc R . . . .
C7 C 0.2378(5) 0.3714(4) 0.50380(19) 0.0135(7) Uani 1 1 d . . . . .
C3 C 0.3678(5) 0.6474(4) 0.5627(2) 0.0174(7) Uani 1 1 d . . . . .
H3 H 0.443084 0.724621 0.603349 0.021 Uiso 1 1 calc R . . . .
C15 C 0.3635(6) 0.0824(5) 0.7058(2) 0.0266(9) Uani 1 1 d . . . . .
H15A H 0.268403 0.109780 0.667602 0.040 Uiso 1 1 calc GR . . . .
H15B H 0.309981 -0.002564 0.728031 0.040 Uiso 1 1 calc GR . . . .
H15C H 0.464803 0.040290 0.683023 0.040 Uiso 1 1 calc GR . . . .
C1 C 0.4457(5) 0.4257(4) 0.63328(19) 0.0159(7) Uani 1 1 d . . . . .
H1A H 0.489953 0.316557 0.617837 0.019 Uiso 1 1 calc R . . . .
H1B H 0.553954 0.506571 0.658974 0.019 Uiso 1 1 calc R . . . .
C4 C 0.2820(5) 0.7032(4) 0.5021(2) 0.0199(8) Uani 1 1 d . . . . .
H4 H 0.296736 0.817979 0.501530 0.024 Uiso 1 1 calc R . . . .
C22 C -0.0183(6) -0.1003(5) 0.1723(2) 0.0257(9) Uani 1 1 d . . . . .
H22 H -0.029831 -0.218062 0.162863 0.031 Uiso 1 1 calc R . . . .
C26 C 0.1386(6) -0.1006(5) 0.3031(2) 0.0282(9) Uani 1 1 d . . . . .
H26A H 0.223074 -0.023312 0.343805 0.042 Uiso 1 1 calc GR . . . .
H26B H 0.204166 -0.192364 0.282963 0.042 Uiso 1 1 calc GR . . . .
H26C H 0.034337 -0.144444 0.321898 0.042 Uiso 1 1 calc GR . . . .
C25 C -0.1889(6) -0.1229(6) 0.0403(2) 0.0370(11) Uani 1 1 d . . . . .
H25A H -0.289975 -0.063955 0.020163 0.055 Uiso 1 1 calc GR . . . .
H25B H -0.239133 -0.231421 0.045914 0.055 Uiso 1 1 calc GR . . . .
H25C H -0.102648 -0.138134 0.006115 0.055 Uiso 1 1 calc GR . . . .
C16 C 0.7060(6) 0.3434(6) 0.9649(2) 0.0371(11) Uani 1 1 d . . . . .
H16A H 0.836783 0.381760 0.969996 0.056 Uiso 1 1 calc GR . . . .
H16B H 0.693210 0.226447 0.968221 0.056 Uiso 1 1 calc GR . . . .
H16C H 0.656647 0.409807 1.004857 0.056 Uiso 1 1 calc GR . . . .
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'
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
C9 O1 C1 110.7(2) . . ?
C18 O2 C8 112.6(3) . . ?
O1 C9 C10 119.7(3) . . ?
C14 C9 O1 118.4(3) . . ?
C14 C9 C10 121.8(3) . . ?
O2 C18 C19 118.5(3) . . ?
C23 C18 O2 119.8(3) . . ?
C23 C18 C19 121.7(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.4(4) . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
C9 C14 C13 118.1(3) . . ?
C9 C14 C17 121.3(3) . . ?
C13 C14 C17 120.6(3) . . ?
C9 C10 C15 121.6(3) . . ?
C11 C10 C9 117.9(3) . . ?
C11 C10 C15 120.4(3) . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C19 C24 121.5(3) . . ?
C20 C19 C18 117.7(3) . . ?
C20 C19 C24 120.8(3) . . ?
C7 C2 C1 123.3(3) . . ?
C3 C2 C7 116.9(3) . . ?
C3 C2 C1 119.7(3) . . ?
C13 C12 C11 118.9(4) . . ?
C13 C12 C16 120.7(4) . . ?
C11 C12 C16 120.4(4) . . ?
C20 C21 C22 118.4(3) . . ?
C20 C21 C25 120.8(4) . . ?
C22 C21 C25 120.8(4) . . ?
C5 C6 C8 119.0(3) . . ?
C5 C6 C7 117.6(3) . . ?
C7 C6 C8 123.4(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C19 C20 H20 118.9 . . ?
C21 C20 C19 122.1(4) . . ?
C21 C20 H20 118.9 . . ?
C18 C23 C26 121.6(3) . . ?
C22 C23 C18 118.3(3) . . ?
C22 C23 C26 120.1(3) . . ?
O2 C8 C6 107.5(3) . . ?
O2 C8 H8A 110.2 . . ?
O2 C8 H8B 110.2 . . ?
C6 C8 H8A 110.2 . . ?
C6 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C10 C11 C12 121.8(4) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C2 C7 Br1 118.3(3) . . ?
C6 C7 Br1 118.9(3) . . ?
C6 C7 C2 122.8(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C1 C2 109.0(3) . . ?
O1 C1 H1A 109.9 . . ?
O1 C1 H1B 109.9 . . ?
C2 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C21 C22 H22 119.1 . . ?
C23 C22 C21 121.8(4) . . ?
C23 C22 H22 119.1 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 C7 1.897(3) . ?
O1 C9 1.397(4) . ?
O1 C1 1.443(4) . ?
O2 C18 1.393(4) . ?
O2 C8 1.445(4) . ?
C9 C14 1.395(5) . ?
C9 C10 1.401(5) . ?
C18 C19 1.403(5) . ?
C18 C23 1.391(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.396(5) . ?
C13 C12 1.386(6) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 C19 1.501(5) . ?
C14 C17 1.506(5) . ?
C10 C11 1.387(5) . ?
C10 C15 1.506(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 C20 1.391(5) . ?
C2 C7 1.406(5) . ?
C2 C3 1.389(5) . ?
C2 C1 1.503(5) . ?
C12 C11 1.391(6) . ?
C12 C16 1.510(5) . ?
C21 C20 1.387(5) . ?
C21 C22 1.389(6) . ?
C21 C25 1.516(5) . ?
C6 C5 1.390(5) . ?
C6 C8 1.502(5) . ?
C6 C7 1.392(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(5) . ?
C20 H20 0.9500 . ?
C23 C22 1.388(5) . ?
C23 C26 1.510(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C11 H11 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.374(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C4 H4 0.9500 . ?
C22 H22 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
