#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:26:09 +0300 (Fri, 05 May 2023) $
#$Revision: 283485 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/92/7159203.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_7159203
loop_
_publ_author_name
'Nalawade, Sachin A.'
'Singh, Manjeet'
'Puneeth Kumar, DRGKoppalu R'
'Dey, Sanjit'
'Gopi, Hosahudya N.'
_publ_section_title
;
 Stereoselective synthesis of backbone extended π-conjugated amino
 esters.
;
_journal_issue                   12
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2586
_journal_page_last               2595
_journal_paper_doi               10.1039/d3ob00090g
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C11 H21 N O3'
_chemical_formula_sum            'C11 H21 N O3'
_chemical_formula_weight         215.29
_chemical_name_common
'(tert-butyl (E)-(5-hydroxy-2-methylpent-3-en-2-yl)carbamate)'
_chemical_name_systematic
'(tert-butyl (E)-(5-hydroxy-2-methylpent-3-en-2-yl)carbamate)'
_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_method           SHELXL-2018/3
_audit_update_record
;
2022-10-17 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.989(8)
_cell_angle_beta                 108.378(7)
_cell_angle_gamma                91.637(8)
_cell_formula_units_Z            4
_cell_length_a                   9.165(2)
_cell_length_b                   10.586(3)
_cell_length_c                   13.936(3)
_cell_measurement_reflns_used    5120
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.349
_cell_measurement_theta_min      2.432
_cell_volume                     1282.1(5)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  microfocus
_diffrn_measurement_method       APEXIII
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35186
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.349
_diffrn_reflns_theta_min         2.432
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS,2008
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_description       plate-shape
_exptl_crystal_F_000             472.0
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0175(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.1417
_refine_ls_R_factor_gt           0.0941
_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)+(0.0001P)²+2.2682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1561
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3552
_reflns_number_total             5120
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00090g2.cif
_cod_data_source_block           3c
_cod_depositor_comments
'Adding full bibliography for 7159200--7159209.cif.'
_cod_database_code               7159203
_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_min   0.961
_shelx_estimated_absorpt_t_max   0.976
_exptl_absorpt_special_details   multi-scan
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
C1 C 0.6844(4) -0.0633(3) 0.0499(2) 0.0352(8) Uani 1 1 d . . . . .
H1A H 0.637651 -0.039991 -0.019803 0.042 Uiso 1 1 calc R U . . .
H1B H 0.775621 -0.109848 0.053867 0.042 Uiso 1 1 calc R U . . .
C2 C 0.7297(4) 0.0535(3) 0.1151(2) 0.0307(7) Uani 1 1 d . . . . .
H2 H 0.803773 0.107180 0.103052 0.037 Uiso 1 1 calc R U . . .
C3 C 0.6752(3) 0.0884(3) 0.1881(2) 0.0260(7) Uani 1 1 d . . . . .
H3 H 0.598570 0.036395 0.198688 0.031 Uiso 1 1 calc R U . . .
C4 C 0.7252(4) 0.2043(3) 0.2558(2) 0.0288(7) Uani 1 1 d . . . . .
C5 C 0.7956(4) 0.1619(3) 0.3646(2) 0.0418(9) Uani 1 1 d . . . . .
H5A H 0.820642 0.234636 0.409585 0.063 Uiso 1 1 calc R U . . .
H5B H 0.887349 0.116974 0.370217 0.063 Uiso 1 1 calc R U . . .
H5C H 0.723010 0.107432 0.382220 0.063 Uiso 1 1 calc R U . . .
C6 C 0.8407(4) 0.2911(3) 0.2278(3) 0.0434(9) Uani 1 1 d . . . . .
H6A H 0.795679 0.319303 0.160059 0.065 Uiso 1 1 calc R U . . .
H6B H 0.931584 0.245752 0.231990 0.065 Uiso 1 1 calc R U . . .
H6C H 0.867310 0.362903 0.273796 0.065 Uiso 1 1 calc R U . . .
C7 C 0.4906(3) 0.3245(3) 0.1734(2) 0.0247(7) Uani 1 1 d . . . . .
C8 C 0.2624(4) 0.4543(3) 0.1252(2) 0.0304(7) Uani 1 1 d . . . . .
C9 C 0.3245(4) 0.5506(3) 0.0680(3) 0.0456(9) Uani 1 1 d . . . . .
H9A H 0.396539 0.607612 0.115172 0.068 Uiso 1 1 calc R U . . .
H9B H 0.241201 0.597372 0.025833 0.068 Uiso 1 1 calc R U . . .
H9C H 0.375244 0.508220 0.026680 0.068 Uiso 1 1 calc R U . . .
C10 C 0.1819(4) 0.5191(4) 0.1921(3) 0.0461(10) Uani 1 1 d . . . . .
H10A H 0.151931 0.457372 0.232583 0.069 Uiso 1 1 calc R U . . .
H10B H 0.092187 0.559279 0.150350 0.069 Uiso 1 1 calc R U . . .
H10C H 0.250830 0.581493 0.235360 0.069 Uiso 1 1 calc R U . . .
C11 C 0.1573(4) 0.3552(3) 0.0568(3) 0.0464(10) Uani 1 1 d . . . . .
H11A H 0.208814 0.317406 0.013816 0.070 Uiso 1 1 calc R U . . .
H11B H 0.065669 0.393654 0.015924 0.070 Uiso 1 1 calc R U . . .
H11C H 0.130504 0.291315 0.096948 0.070 Uiso 1 1 calc R U . . .
C12 C 0.6919(4) 0.4383(3) 0.5262(2) 0.0368(8) Uani 1 1 d . . . . .
H12A H 0.782142 0.389154 0.555493 0.044 Uiso 1 1 calc R U . . .
H12B H 0.653200 0.464827 0.580400 0.044 Uiso 1 1 calc R U . . .
C13 C 0.7359(4) 0.5519(3) 0.4789(2) 0.0335(8) Uani 1 1 d . . . . .
H13 H 0.818583 0.601854 0.518862 0.040 Uiso 1 1 calc R U . . .
C14 C 0.6695(4) 0.5885(3) 0.3862(2) 0.0260(7) Uani 1 1 d . . . . .
H14 H 0.584647 0.540213 0.346959 0.031 Uiso 1 1 calc R U . . .
C15 C 0.7178(3) 0.7015(3) 0.3371(2) 0.0260(7) Uani 1 1 d . . . . .
C16 C 0.8297(4) 0.7924(3) 0.4121(3) 0.0373(8) Uani 1 1 d . . . . .
H16A H 0.851421 0.864245 0.377082 0.056 Uiso 1 1 calc R U . . .
H16B H 0.923368 0.750467 0.444291 0.056 Uiso 1 1 calc R U . . .
H16C H 0.785013 0.819895 0.462240 0.056 Uiso 1 1 calc R U . . .
C17 C 0.7892(4) 0.6536(3) 0.2582(2) 0.0348(8) Uani 1 1 d . . . . .
H17A H 0.717815 0.595719 0.211578 0.052 Uiso 1 1 calc R U . . .
H17B H 0.882083 0.611291 0.291561 0.052 Uiso 1 1 calc R U . . .
H17C H 0.812307 0.723876 0.222183 0.052 Uiso 1 1 calc R U . . .
C18 C 0.4812(4) 0.8198(3) 0.3219(2) 0.0269(7) Uani 1 1 d . . . . .
C19 C 0.2595(4) 0.9586(3) 0.2777(3) 0.0342(8) Uani 1 1 d . . . . .
C20 C 0.3304(5) 1.0576(4) 0.3586(3) 0.0586(11) Uani 1 1 d . . . . .
H20A H 0.378673 1.017519 0.421443 0.088 Uiso 1 1 calc R U . . .
H20B H 0.251937 1.111369 0.366181 0.088 Uiso 1 1 calc R U . . .
H20C H 0.406050 1.107326 0.340015 0.088 Uiso 1 1 calc R U . . .
C21 C 0.1815(5) 1.0204(5) 0.1789(3) 0.0656(13) Uani 1 1 d . . . . .
H21A H 0.253360 1.077331 0.162882 0.098 Uiso 1 1 calc R U . . .
H21B H 0.095865 1.066556 0.184696 0.098 Uiso 1 1 calc R U . . .
H21C H 0.145474 0.956665 0.126127 0.098 Uiso 1 1 calc R U . . .
C22 C 0.1503(5) 0.8688(4) 0.3051(4) 0.0747(15) Uani 1 1 d . . . . .
H22A H 0.119477 0.801059 0.255452 0.112 Uiso 1 1 calc R U . . .
H22B H 0.061254 0.912958 0.307215 0.112 Uiso 1 1 calc R U . . .
H22C H 0.200295 0.834966 0.370328 0.112 Uiso 1 1 calc R U . . .
N1 N 0.5892(3) 0.2759(2) 0.25599(18) 0.0277(6) Uani 1 1 d . . . . .
H1C H 0.572267 0.287194 0.312764 0.033 Uiso 1 1 calc R U . . .
N2 N 0.5798(3) 0.7693(2) 0.28015(18) 0.0258(6) Uani 1 1 d . . . . .
H2A H 0.561707 0.776749 0.216132 0.031 Uiso 1 1 calc R U . . .
O1 O 0.5794(3) -0.1420(2) 0.07956(15) 0.0363(6) Uani 1 1 d . . . . .
H1 H 0.538788 -0.194381 0.034260 0.055 Uiso 1 1 calc R U . . .
O2 O 0.4925(3) 0.3092(2) 0.08694(15) 0.0327(6) Uani 1 1 d . . . . .
O3 O 0.3886(2) 0.3940(2) 0.20083(14) 0.0312(5) Uani 1 1 d . . . . .
O4 O 0.5776(3) 0.3615(2) 0.45476(15) 0.0365(6) Uani 1 1 d . . . . .
H4 H 0.535351 0.314099 0.484613 0.055 Uiso 1 1 calc R U . . .
O5 O 0.4797(3) 0.8066(2) 0.40803(16) 0.0375(6) Uani 1 1 d . . . . .
O6 O 0.3805(2) 0.8895(2) 0.25269(16) 0.0342(6) Uani 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'
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
O1 C1 C2 111.9(3) . . ?
O1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
O1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C3 C2 C1 126.5(3) . . ?
C3 C2 H2 116.8 . . ?
C1 C2 H2 116.8 . . ?
C2 C3 C4 126.2(3) . . ?
C2 C3 H3 116.9 . . ?
C4 C3 H3 116.9 . . ?
N1 C4 C3 109.8(2) . . ?
N1 C4 C6 109.7(3) . . ?
C3 C4 C6 113.9(3) . . ?
N1 C4 C5 105.2(2) . . ?
C3 C4 C5 108.3(3) . . ?
C6 C4 C5 109.4(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 N1 125.7(3) . . ?
O2 C7 O3 125.0(3) . . ?
N1 C7 O3 109.3(2) . . ?
O3 C8 C11 110.0(3) . . ?
O3 C8 C9 110.6(3) . . ?
C11 C8 C9 112.9(3) . . ?
O3 C8 C10 101.4(2) . . ?
C11 C8 C10 110.7(3) . . ?
C9 C8 C10 110.6(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 C13 111.6(2) . . ?
O4 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
O4 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 126.4(3) . . ?
C14 C13 H13 116.8 . . ?
C12 C13 H13 116.8 . . ?
C13 C14 C15 126.3(3) . . ?
C13 C14 H14 116.9 . . ?
C15 C14 H14 116.9 . . ?
N2 C15 C14 109.3(2) . . ?
N2 C15 C16 109.5(2) . . ?
C14 C15 C16 113.3(3) . . ?
N2 C15 C17 105.9(2) . . ?
C14 C15 C17 108.4(2) . . ?
C16 C15 C17 110.1(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O5 C18 N2 126.5(3) . . ?
O5 C18 O6 124.2(3) . . ?
N2 C18 O6 109.2(2) . . ?
O6 C19 C20 110.2(3) . . ?
O6 C19 C22 110.8(3) . . ?
C20 C19 C22 113.0(3) . . ?
O6 C19 C21 101.4(3) . . ?
C20 C19 C21 110.0(3) . . ?
C22 C19 C21 110.9(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C7 N1 C4 124.2(2) . . ?
C7 N1 H1C 117.9 . . ?
C4 N1 H1C 117.9 . . ?
C18 N2 C15 124.1(2) . . ?
C18 N2 H2A 117.9 . . ?
C15 N2 H2A 117.9 . . ?
C1 O1 H1 109.5 . . ?
C7 O3 C8 121.3(2) . . ?
C12 O4 H4 109.5 . . ?
C18 O6 C19 121.5(2) . . ?
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 O1 1.417(4) . ?
C1 C2 1.490(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.318(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.503(4) . ?
C3 H3 0.9300 . ?
C4 N1 1.478(4) . ?
C4 C6 1.527(5) . ?
C4 C5 1.530(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 O2 1.218(3) . ?
C7 N1 1.341(4) . ?
C7 O3 1.348(4) . ?
C8 O3 1.467(3) . ?
C8 C11 1.505(5) . ?
C8 C9 1.510(5) . ?
C8 C10 1.525(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O4 1.420(4) . ?
C12 C13 1.487(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.313(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.511(4) . ?
C14 H14 0.9300 . ?
C15 N2 1.477(4) . ?
C15 C16 1.517(4) . ?
C15 C17 1.532(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O5 1.215(3) . ?
C18 N2 1.338(4) . ?
C18 O6 1.352(4) . ?
C19 O6 1.472(4) . ?
C19 C20 1.500(5) . ?
C19 C22 1.501(5) . ?
C19 C21 1.508(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 H1C 0.8600 . ?
N2 H2A 0.8600 . ?
O1 H1 0.8200 . ?
O4 H4 0.8200 . ?
