#------------------------------------------------------------------------------
#$Date: 2021-07-14 07:57:56 +0300 (Wed, 14 Jul 2021) $
#$Revision: 267525 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243868.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243868
loop_
_publ_author_name
'Martens, Viktor'
'Görls, Helmar'
'Imhof, Wolfgang'
_publ_section_title
;
 Crystal structure of 2-oxo-2-phenylethyl diisopropylcarbamate
;
_journal_coeditor_code           ZL5014
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              785
_journal_page_last               787
_journal_paper_doi               10.1107/S2056989021006927
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C15 H21 N O3'
_chemical_formula_moiety         'C15 H21 N O3'
_chemical_formula_sum            'C15 H21 N O3'
_chemical_formula_weight         263.33
_chemical_name_systematic
;
2-oxo-2-phenylethyl diisopropylcarbamate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 113.4680(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.4574(8)
_cell_length_b                   5.7020(2)
_cell_length_c                   14.8058(6)
_cell_measurement_reflns_used    13968
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.482
_cell_measurement_theta_min      2.751
_cell_volume                     1429.33(10)
_computing_cell_refinement
;
DENZO (Otwinowski & Minor, 1997)
;
_computing_data_collection
;
COLLECT (Nonius 1998)
;
_computing_data_reduction
;
DENZO (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 2012)
;
_computing_publication_material
;
MERCURY (Macrae et al.,  2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi + omega - scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.751
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.206
_refine_ls_extinction_coef       0.0093(16)
_refine_ls_extinction_method
;
SHELXL2018/3 (Sheldrick 2015)
;
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0494
_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)+(0.0368P)²+0.6743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1131
_reflns_number_gt                2464
_reflns_number_total             3280
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zl5014sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243868
_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   0.991
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.38605(6) 0.7949(2) 0.38826(9) 0.0338(3) Uani d 1 . .
O O2 0.27936(6) 0.4581(2) 0.32610(8) 0.0280(3) Uani d 1 . .
O O3 0.24228(6) 0.6202(2) 0.17458(8) 0.0285(3) Uani d 1 . .
N N1 0.17054(7) 0.6836(3) 0.26709(9) 0.0285(3) Uani d 1 . .
C C1 0.41005(8) 0.6137(3) 0.36687(11) 0.0234(3) Uani d 1 . .
C C2 0.35448(8) 0.4079(3) 0.32488(12) 0.0257(3) Uani d 1 . .
H H2A 0.348514 0.377390 0.256450 0.031 Uiso calc 1 . .
H H2B 0.376866 0.265560 0.364461 0.031 Uiso calc 1 . .
C C3 0.23136(8) 0.5945(3) 0.24965(11) 0.0249(3) Uani d 1 . .
C C4 0.16762(9) 0.6747(4) 0.36534(12) 0.0371(4) Uani d 1 . .
H H4 0.211633 0.570586 0.407718 0.044 Uiso calc 1 . .
C C5 0.18152(13) 0.9155(5) 0.41331(15) 0.0605(7) Uani d 1 . .
H H5A 0.228794 0.985787 0.409862 0.091 Uiso calc 1 . .
H H5B 0.188987 0.899895 0.482386 0.091 Uiso calc 1 . .
H H5C 0.135734 1.015930 0.378631 0.091 Uiso calc 1 . .
C C6 0.09072(11) 0.5665(4) 0.36026(15) 0.0452(5) Uani d 1 . .
H H6A 0.046572 0.670305 0.322993 0.068 Uiso calc 1 . .
H H6B 0.093071 0.545940 0.427083 0.068 Uiso calc 1 . .
H H6C 0.083000 0.413759 0.327431 0.068 Uiso calc 1 . .
C C7 0.11069(9) 0.8271(3) 0.19039(11) 0.0278(4) Uani d 1 . .
H H7 0.074178 0.887235 0.220031 0.033 Uiso calc 1 . .
C C8 0.06055(9) 0.6780(3) 0.10240(12) 0.0319(4) Uani d 1 . .
H H8A 0.019602 0.775918 0.054376 0.048 Uiso calc 1 . .
H H8B 0.035643 0.551161 0.124422 0.048 Uiso calc 1 . .
H H8C 0.094128 0.610990 0.071729 0.048 Uiso calc 1 . .
C C9 0.14496(11) 1.0413(3) 0.16096(14) 0.0405(5) Uani d 1 . .
H H9A 0.176297 0.991762 0.124230 0.061 Uiso calc 1 . .
H H9B 0.178789 1.126741 0.220191 0.061 Uiso calc 1 . .
H H9C 0.101940 1.143637 0.119443 0.061 Uiso calc 1 . .
C C10 0.49370(8) 0.5861(3) 0.37810(11) 0.0248(3) Uani d 1 . .
C C11 0.51983(9) 0.3863(3) 0.34607(12) 0.0315(4) Uani d 1 . .
H H11 0.484354 0.260546 0.317232 0.038 Uiso calc 1 . .
C C12 0.59781(10) 0.3710(4) 0.35634(13) 0.0420(5) Uani d 1 . .
H H12 0.615586 0.234665 0.334388 0.050 Uiso calc 1 . .
C C13 0.64925(10) 0.5519(4) 0.39804(13) 0.0478(6) Uani d 1 . .
H H13 0.702529 0.540331 0.404875 0.057 Uiso calc 1 . .
C C14 0.62389(10) 0.7512(4) 0.43024(13) 0.0437(5) Uani d 1 . .
H H14 0.659736 0.876252 0.458872 0.052 Uiso calc 1 . .
C C15 0.54637(9) 0.7686(3) 0.42078(12) 0.0327(4) Uani d 1 . .
H H15 0.529143 0.904967 0.443406 0.039 Uiso calc 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O2 C2 . . 114.64(12) ?
C3 N1 C7 . . 119.12(13) ?
C3 N1 C4 . . 122.37(13) ?
C7 N1 C4 . . 117.83(13) ?
O1 C1 C10 . . 121.89(14) ?
O1 C1 C2 . . 120.45(14) ?
C10 C1 C2 . . 117.64(13) ?
O2 C2 C1 . . 110.00(13) ?
O2 C2 H2A . . 109.7 ?
C1 C2 H2A . . 109.7 ?
O2 C2 H2B . . 109.7 ?
C1 C2 H2B . . 109.7 ?
H2A C2 H2B . . 108.2 ?
O3 C3 N1 . . 125.75(14) ?
O3 C3 O2 . . 122.46(14) ?
N1 C3 O2 . . 111.72(13) ?
N1 C4 C5 . . 111.30(16) ?
N1 C4 C6 . . 111.37(14) ?
C5 C4 C6 . . 111.69(16) ?
N1 C4 H4 . . 107.4 ?
C5 C4 H4 . . 107.4 ?
C6 C4 H4 . . 107.4 ?
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 ?
N1 C7 C9 . . 113.40(13) ?
N1 C7 C8 . . 111.27(13) ?
C9 C7 C8 . . 112.63(14) ?
N1 C7 H7 . . 106.3 ?
C9 C7 H7 . . 106.3 ?
C8 C7 H7 . . 106.3 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C15 C10 C11 . . 119.50(15) ?
C15 C10 C1 . . 118.42(15) ?
C11 C10 C1 . . 122.07(14) ?
C12 C11 C10 . . 119.92(17) ?
C12 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
C13 C12 C11 . . 120.25(18) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C12 C13 C14 . . 120.29(16) ?
C12 C13 H13 . . 119.9 ?
C14 C13 H13 . . 119.9 ?
C13 C14 C15 . . 120.11(18) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C14 C15 C10 . . 119.93(18) ?
C14 C15 H15 . . 120.0 ?
C10 C15 H15 . . 120.0 ?
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
O1 C1 . 1.2149(19) ?
O2 C3 . 1.3684(18) ?
O2 C2 . 1.4230(17) ?
O3 C3 . 1.2148(18) ?
N1 C3 . 1.348(2) ?
N1 C7 . 1.4764(19) ?
N1 C4 . 1.478(2) ?
C1 C10 . 1.494(2) ?
C1 C2 . 1.519(2) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C4 C5 . 1.520(3) ?
C4 C6 . 1.522(2) ?
C4 H4 . 1.0000 ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C7 C9 . 1.517(2) ?
C7 C8 . 1.522(2) ?
C7 H7 . 1.0000 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 C15 . 1.392(2) ?
C10 C11 . 1.392(2) ?
C11 C12 . 1.389(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.371(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.384(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.385(2) ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2B O1 1_545 0.99 2.70 3.605(2) 151.7 yes
C5 H5B O3 4_576 0.98 2.62 3.578(2) 167.3 yes
C9 H9B O2 1_565 0.98 2.68 3.599(2) 157.3 yes

_cod_database_fobs_code 2243868
