#------------------------------------------------------------------------------
#$Date: 2023-05-05 04:12:39 +0300 (Fri, 05 May 2023) $
#$Revision: 283188 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/84/1568442.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_1568442
loop_
_publ_author_name
'Ong, How Chee'
'Coimbra, João T S'
'Ramos, Maria J.'
'Xing, Bengang'
'Fernandes, Pedro A.'
'García, Felipe'
_publ_section_title
;
 Beyond the TPP⁺ "gold standard": a new generation
 mitochondrial delivery vector based on extended PN frameworks.
;
_journal_issue                   15
_journal_name_full               'Chemical science'
_journal_page_first              4126
_journal_page_last               4133
_journal_paper_doi               10.1039/d2sc06508h
_journal_volume                  14
_journal_year                    2023
_chemical_formula_sum            'C19 H19 Br N P'
_chemical_formula_weight         372.23
_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   mixed
_atom_sites_solution_primary     dual
_audit_update_record
;
2021-05-17 deposited with the CCDC.	2023-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                63.4570(10)
_cell_angle_beta                 80.694(2)
_cell_angle_gamma                85.3810(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4139(4)
_cell_length_b                   9.7021(4)
_cell_length_c                   10.4201(4)
_cell_measurement_reflns_used    5834
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      32.0207
_cell_measurement_theta_min      2.1923
_cell_volume                     840.16(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2017)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_unetI/netI     0.1030
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32540
_diffrn_reflns_theta_full        39.50
_diffrn_reflns_theta_max         39.50
_diffrn_reflns_theta_min         2.19
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    2.538
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile, diethyl ether'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.988
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         10017
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0341P)²+0.1842P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                5948
_reflns_number_total             10017
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc06508h2.cif
_cod_data_source_block           fg1003m
_cod_depositor_comments
;
The following automatic conversions were performed:

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 1568442--1568445.cif.
;
_cod_database_code               1568442
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
Br Br1 0.17568(2) 0.21005(2) 0.07624(2) 0.01834(5) Uani d . . . 1 . .
C C1 0.5230(2) 0.1009(2) 0.2510(2) 0.0213(4) Uani d . . . 1 . .
H H1A 0.626346 0.113213 0.215434 0.032 Uiso calc U . R 1 . .
H H1B 0.480894 0.040623 0.212403 0.032 Uiso calc U . R 1 . .
H H1C 0.508452 0.047238 0.35712 0.032 Uiso calc U . R 1 . .
C C2 0.30758(17) 0.24363(19) 0.46965(19) 0.0124(3) Uani d . . . 1 . .
C C3 0.22949(18) 0.1191(2) 0.4850(2) 0.0145(3) Uani d . . . 1 . .
H H3 0.244314 0.084297 0.411833 0.017 Uiso calc U . R 1 . .
C C4 0.12991(19) 0.0467(2) 0.6085(2) 0.0175(4) Uani d . . . 1 . .
H H4 0.0768 -0.0383 0.620043 0.021 Uiso calc U . R 1 . .
C C5 0.10795(19) 0.0980(2) 0.7147(2) 0.0187(4) Uani d . . . 1 . .
H H5 0.040565 0.047114 0.799174 0.022 Uiso calc U . R 1 . .
C C6 0.1836(2) 0.2235(2) 0.6989(2) 0.0192(4) Uani d . . . 1 . .
H H6 0.1676 0.25846 0.771909 0.023 Uiso calc U . R 1 . .
C C7 0.28261(19) 0.2970(2) 0.5758(2) 0.0155(3) Uani d . . . 1 . .
H H7 0.333464 0.383682 0.563639 0.019 Uiso calc U . R 1 . .
C C8 0.36778(18) 0.52967(19) 0.21117(19) 0.0130(3) Uani d . . . 1 . .
C C9 0.23300(19) 0.5462(2) 0.1653(2) 0.0176(3) Uani d . . . 1 . .
H H9 0.182265 0.457728 0.181762 0.021 Uiso calc U . R 1 . .
C C10 0.1735(2) 0.6922(2) 0.0958(2) 0.0207(4) Uani d . . . 1 . .
H H10 0.082425 0.704006 0.063609 0.025 Uiso calc U . R 1 . .
C C11 0.2480(2) 0.8209(2) 0.0735(2) 0.0215(4) Uani d . . . 1 . .
H H11 0.206448 0.920675 0.02843 0.026 Uiso calc U . R 1 . .
C C12 0.3816(2) 0.8047(2) 0.1164(2) 0.0218(4) Uani d . . . 1 . .
H H12 0.432027 0.893576 0.099339 0.026 Uiso calc U . R 1 . .
C C13 0.4438(2) 0.6596(2) 0.1843(2) 0.0177(3) Uani d . . . 1 . .
H H13 0.53686 0.64922 0.212084 0.021 Uiso calc U . R 1 . .
C C14 0.60928(18) 0.3418(2) 0.35239(19) 0.0131(3) Uani d . . . 1 . .
C C15 0.64036(19) 0.2829(2) 0.4938(2) 0.0145(3) Uani d . . . 1 . .
H H15 0.56564 0.241852 0.573403 0.017 Uiso calc U . R 1 . .
C C16 0.7812(2) 0.2844(2) 0.5179(2) 0.0192(4) Uani d . . . 1 . .
H H16 0.802893 0.243285 0.614177 0.023 Uiso calc U . R 1 . .
C C17 0.8900(2) 0.3458(2) 0.4016(2) 0.0193(4) Uani d . . . 1 . .
H H17 0.985777 0.347897 0.418531 0.023 Uiso calc U . R 1 . .
C C18 0.8596(2) 0.4041(2) 0.2607(2) 0.0209(4) Uani d . . . 1 . .
H H18 0.934691 0.44476 0.181444 0.025 Uiso calc U . R 1 . .
C C19 0.71982(19) 0.4030(2) 0.2356(2) 0.0193(4) Uani d . . . 1 . .
H H19 0.698871 0.443905 0.139144 0.023 Uiso calc U . R 1 . .
N N1 0.45294(16) 0.25365(18) 0.20303(17) 0.0140(3) Uani d . . D 1 . .
P P1 0.43411(5) 0.33885(5) 0.30821(5) 0.01134(8) Uani d . . . 1 . .
H H1N 0.386(2) 0.260(3) 0.159(3) 0.038(8) Uiso d . . D 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'
P P 0.1023 0.0942 '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
N1 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
N1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C7 C2 C3 . . 120.11(16) ?
C7 C2 P1 . . 120.71(13) ?
C3 C2 P1 . . 119.12(14) ?
C4 C3 C2 . . 119.33(17) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C5 C4 C3 . . 120.25(17) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C4 C5 C6 . . 120.67(17) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C7 C6 C5 . . 119.56(18) ?
C7 C6 H6 . . 120.2 ?
C5 C6 H6 . . 120.2 ?
C6 C7 C2 . . 120.06(17) ?
C6 C7 H7 . . 120.0 ?
C2 C7 H7 . . 120.0 ?
C13 C8 C9 . . 120.11(17) ?
C13 C8 P1 . . 122.12(14) ?
C9 C8 P1 . . 117.75(13) ?
C10 C9 C8 . . 119.93(17) ?
C10 C9 H9 . . 120.0 ?
C8 C9 H9 . . 120.0 ?
C9 C10 C11 . . 119.58(18) ?
C9 C10 H10 . . 120.2 ?
C11 C10 H10 . . 120.2 ?
C12 C11 C10 . . 120.41(18) ?
C12 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
C11 C12 C13 . . 120.81(18) ?
C11 C12 H12 . . 119.6 ?
C13 C12 H12 . . 119.6 ?
C12 C13 C8 . . 119.12(18) ?
C12 C13 H13 . . 120.4 ?
C8 C13 H13 . . 120.4 ?
C15 C14 C19 . . 119.77(16) ?
C15 C14 P1 . . 123.76(13) ?
C19 C14 P1 . . 116.43(13) ?
C16 C15 C14 . . 119.75(17) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C17 C16 C15 . . 120.09(17) ?
C17 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C16 C17 C18 . . 120.34(17) ?
C16 C17 H17 . . 119.8 ?
C18 C17 H17 . . 119.8 ?
C19 C18 C17 . . 119.98(18) ?
C19 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C18 C19 C14 . . 120.06(18) ?
C18 C19 H19 . . 120.0 ?
C14 C19 H19 . . 120.0 ?
C1 N1 P1 . . 119.21(13) ?
C1 N1 H1N . . 111.2(19) ?
P1 N1 H1N . . 117.7(19) ?
N1 P1 C8 . . 108.43(8) ?
N1 P1 C14 . . 106.15(8) ?
C8 P1 C14 . . 111.06(8) ?
N1 P1 C2 . . 112.82(8) ?
C8 P1 C2 . . 107.47(8) ?
C14 P1 C2 . . 110.93(8) ?
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 N1 . 1.473(2) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 C7 . 1.398(3) ?
C2 C3 . 1.400(2) ?
C2 P1 . 1.8007(17) ?
C3 C4 . 1.392(2) ?
C3 H3 . 0.95 ?
C4 C5 . 1.384(3) ?
C4 H4 . 0.95 ?
C5 C6 . 1.393(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.387(2) ?
C6 H6 . 0.95 ?
C7 H7 . 0.95 ?
C8 C13 . 1.395(2) ?
C8 C9 . 1.399(2) ?
C8 P1 . 1.7846(18) ?
C9 C10 . 1.390(3) ?
C9 H9 . 0.95 ?
C10 C11 . 1.392(3) ?
C10 H10 . 0.95 ?
C11 C12 . 1.376(3) ?
C11 H11 . 0.95 ?
C12 C13 . 1.391(3) ?
C12 H12 . 0.95 ?
C13 H13 . 0.95 ?
C14 C15 . 1.394(2) ?
C14 C19 . 1.400(2) ?
C14 P1 . 1.7879(17) ?
C15 C16 . 1.391(2) ?
C15 H15 . 0.95 ?
C16 C17 . 1.387(3) ?
C16 H16 . 0.95 ?
C17 C18 . 1.388(3) ?
C17 H17 . 0.95 ?
C18 C19 . 1.384(3) ?
C18 H18 . 0.95 ?
C19 H19 . 0.95 ?
N1 P1 . 1.6245(16) ?
N1 H1N . 0.823(16) ?
