#------------------------------------------------------------------------------
#$Date: 2024-02-04 14:20:13 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289580 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/29/7062961.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_7062961
loop_
_publ_author_name
'Chau Nguyen, Khiem'
'Chung, Duy T. M.'
'Nalaoh, Phattananawee'
'Lindsey, Jonathan S.'
_publ_section_title
;
 Synthesis of chiral hexynones for use as precursors to native
 photosynthetic hydroporphyrins
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2097
_journal_page_last               2117
_journal_paper_doi               10.1039/D3NJ03900E
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C17 H31 N O3 Si'
_chemical_formula_sum            'C17 H31 N O3 Si'
_chemical_formula_weight         325.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-08-06 deposited with the CCDC.	2023-12-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.786(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1517(11)
_cell_length_b                   11.1177(19)
_cell_length_c                   14.455(2)
_cell_measurement_reflns_used    6393
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.31
_cell_volume                     988.1(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11928
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.744
_diffrn_reflns_theta_min         2.311
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1406 before and 0.0542 after correction.
The Ratio of minimum to maximum transmission is 0.8096.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.094
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.628
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1463 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4010
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0433
_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)+(0.0228P)²+0.4382P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                3646
_reflns_number_total             4010
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj03900e2.cif
_cod_data_source_block           mo_ncsu_pn35_kcn829_0m_a
_cod_depositor_comments
'Adding full bibliography for 7062961--7062963.cif.'
_cod_database_code               7062961
_shelx_shelxl_version_number     2019/1
_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   0.988
_shelx_estimated_absorpt_t_min   0.923
_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 Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C13(H13A,H13B)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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_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
C1 C 1.1268(6) 0.3589(4) 0.9508(2) 0.0372(8) Uani 1 1 d . . . . .
H1A H 1.191898 0.310208 1.000912 0.056 Uiso 1 1 calc GR . . . .
H1B H 1.192535 0.439214 0.951807 0.056 Uiso 1 1 calc GR . . . .
H1C H 1.152886 0.320306 0.891209 0.056 Uiso 1 1 calc GR . . . .
C2 C 0.0597(5) 0.5779(3) 0.4499(2) 0.0216(7) Uani 1 1 d . . . . .
H2 H -0.042651 0.624465 0.488652 0.026 Uiso 1 1 calc R . . . .
C3 C -0.0540(6) 0.4631(3) 0.4141(2) 0.0281(7) Uani 1 1 d . . . . .
H3A H -0.183634 0.445050 0.450505 0.034 Uiso 1 1 calc R . . . .
H3B H -0.099614 0.471914 0.348137 0.034 Uiso 1 1 calc R . . . .
C4 C 0.2664(5) 0.4086(2) 0.4858(2) 0.0226(7) Uani 1 1 d . . . . .
C5 C 0.3788(5) 0.5930(2) 0.5698(2) 0.0193(6) Uani 1 1 d . . . . .
H5 H 0.315069 0.674948 0.577896 0.023 Uiso 1 1 calc R . . . .
C6 C 0.4041(5) 0.5345(3) 0.6657(2) 0.0206(6) Uani 1 1 d . . . . .
H6 H 0.444208 0.448327 0.656319 0.025 Uiso 1 1 calc R . . . .
C7 C 0.5922(5) 0.5946(3) 0.7226(2) 0.0232(7) Uani 1 1 d . . . . .
H7 H 0.720240 0.598758 0.681710 0.028 Uiso 1 1 calc R . . . .
C8 C 0.6561(5) 0.5181(3) 0.8031(2) 0.0244(7) Uani 1 1 d . . . . .
C9 C 0.7126(6) 0.4576(3) 0.8681(2) 0.0285(7) Uani 1 1 d . . . . .
C10 C 0.1530(6) 0.6617(3) 0.3758(2) 0.0258(7) Uani 1 1 d . . . . .
H10 H 0.230171 0.729093 0.408781 0.031 Uiso 1 1 calc R . . . .
C11 C 0.3162(6) 0.6000(3) 0.3148(2) 0.0329(8) Uani 1 1 d . . . . .
H11A H 0.380931 0.659564 0.273885 0.049 Uiso 1 1 calc GR . . . .
H11B H 0.242191 0.537974 0.277389 0.049 Uiso 1 1 calc GR . . . .
H11C H 0.430834 0.562826 0.353734 0.049 Uiso 1 1 calc GR . . . .
C12 C 0.1897(6) 0.5369(3) 0.7151(2) 0.0301(7) Uani 1 1 d . . . . .
H12A H 0.209842 0.501176 0.776789 0.045 Uiso 1 1 calc GR . . . .
H12B H 0.080511 0.490739 0.679333 0.045 Uiso 1 1 calc GR . . . .
H12C H 0.140413 0.620271 0.721146 0.045 Uiso 1 1 calc GR . . . .
C13 C 0.5445(6) 0.7245(3) 0.7549(2) 0.0283(7) Uani 1 1 d . . . . .
H13A H 0.491100 0.772743 0.701290 0.034 Uiso 1 1 calc R . . . .
H13B H 0.428717 0.722656 0.800905 0.034 Uiso 1 1 calc R . . . .
C14 C 0.7468(7) 0.7837(3) 0.7977(2) 0.0356(9) Uani 1 1 d . . . . .
H14A H 0.708767 0.863063 0.821862 0.053 Uiso 1 1 calc GR . . . .
H14B H 0.856640 0.792614 0.750579 0.053 Uiso 1 1 calc GR . . . .
H14C H 0.805081 0.733435 0.848406 0.053 Uiso 1 1 calc GR . . . .
C15 C 0.7724(7) 0.4564(4) 1.0752(2) 0.0394(9) Uani 1 1 d . . . . .
H15A H 0.614923 0.465026 1.081124 0.059 Uiso 1 1 calc GR . . . .
H15B H 0.839486 0.536285 1.072756 0.059 Uiso 1 1 calc GR . . . .
H15C H 0.833049 0.412184 1.128699 0.059 Uiso 1 1 calc GR . . . .
C16 C 0.7092(7) 0.2181(3) 0.9707(3) 0.0394(9) Uani 1 1 d . . . . .
H16A H 0.550750 0.224130 0.974165 0.059 Uiso 1 1 calc GR . . . .
H16B H 0.767705 0.175345 1.025339 0.059 Uiso 1 1 calc GR . . . .
H16C H 0.746186 0.173804 0.914727 0.059 Uiso 1 1 calc GR . . . .
C17 C -0.0335(6) 0.7165(3) 0.3170(2) 0.0367(9) Uani 1 1 d . . . . .
H17A H 0.024050 0.779022 0.276682 0.055 Uiso 1 1 calc GR . . . .
H17B H -0.140630 0.752090 0.357691 0.055 Uiso 1 1 calc GR . . . .
H17C H -0.103267 0.653586 0.279037 0.055 Uiso 1 1 calc GR . . . .
N1 N 0.2285(4) 0.5229(2) 0.51003(17) 0.0187(5) Uani 1 1 d . . . . .
O1 O 0.1085(3) 0.3688(2) 0.42560(14) 0.0263(5) Uani 1 1 d . . . . .
O2 O 0.4162(4) 0.34264(16) 0.51094(15) 0.0266(5) Uani 1 1 d . . . . .
O3 O 0.5799(4) 0.6061(2) 0.52769(15) 0.0216(5) Uani 1 1 d . . . . .
Si1 Si 0.82933(15) 0.37221(8) 0.96680(6) 0.0275(2) Uani 1 1 d . . . . .
H3 H 0.589(6) 0.669(3) 0.519(2) 0.017(10) Uiso 1 1 d . . . . .
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'
Si Si 0.0817 0.0704 '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
C3 C2 C10 116.2(3) . . ?
N1 C2 C3 99.2(2) . . ?
N1 C2 C10 113.0(3) . . ?
O1 C3 C2 104.8(2) . . ?
N1 C4 O1 110.5(3) . . ?
O2 C4 N1 128.7(3) . . ?
O2 C4 O1 120.8(3) . . ?
N1 C5 C6 110.5(2) . . ?
O3 C5 C6 111.7(2) . . ?
O3 C5 N1 110.3(2) . . ?
C5 C6 C7 110.4(2) . . ?
C12 C6 C5 110.6(3) . . ?
C12 C6 C7 112.8(3) . . ?
C8 C7 C6 110.1(2) . . ?
C8 C7 C13 110.2(3) . . ?
C13 C7 C6 114.6(3) . . ?
C9 C8 C7 178.4(4) . . ?
C8 C9 Si1 173.7(3) . . ?
C11 C10 C2 113.4(3) . . ?
C11 C10 C17 110.8(3) . . ?
C17 C10 C2 109.7(3) . . ?
C14 C13 C7 111.5(3) . . ?
C2 N1 C5 123.2(2) . . ?
C4 N1 C2 111.5(2) . . ?
C4 N1 C5 123.0(2) . . ?
C4 O1 C3 108.3(2) . . ?
C1 Si1 C15 110.82(18) . . ?
C1 Si1 C16 108.84(19) . . ?
C9 Si1 C1 107.84(16) . . ?
C9 Si1 C15 108.26(17) . . ?
C9 Si1 C16 110.57(17) . . ?
C16 Si1 C15 110.48(19) . . ?
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
C1 Si1 1.858(4) . ?
C2 C3 1.537(4) . ?
C2 C10 1.544(4) . ?
C2 N1 1.467(4) . ?
C3 O1 1.455(4) . ?
C4 N1 1.341(4) . ?
C4 O1 1.357(3) . ?
C4 O2 1.224(4) . ?
C5 C6 1.534(4) . ?
C5 N1 1.470(4) . ?
C5 O3 1.403(4) . ?
C6 C7 1.550(4) . ?
C6 C12 1.520(5) . ?
C7 C8 1.485(4) . ?
C7 C13 1.548(4) . ?
C8 C9 1.198(4) . ?
C9 Si1 1.841(3) . ?
C10 C11 1.520(5) . ?
C10 C17 1.533(4) . ?
C13 C14 1.522(5) . ?
C15 Si1 1.868(4) . ?
C16 Si1 1.868(4) . ?
