#------------------------------------------------------------------------------
#$Date: 2022-06-29 12:18:45 +0300 (Wed, 29 Jun 2022) $
#$Revision: 276392 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/55/8105561.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_8105561
loop_
_publ_author_name
'Sun, Wei'
'Zhu, Zhi-Ling'
'Zuo, Li-Min'
'Zhao, Ting'
'Zhu, Ming-Hui'
'Shan, Guang-Zhi'
_publ_section_title
;
 Crystal structure of tert-butyl
 (R)-(1-(benzylamino)-3-methoxy-1-oxopropan-2-yl)carbamate, C16H24N2O4
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              119
_journal_page_last               120
_journal_paper_doi               10.1515/ncrs-2018-0219
_journal_volume                  234
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C16 H24 N2 O4'
_chemical_formula_sum            'C16 H24 N2 O4'
_chemical_formula_weight         308.37
_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   geom
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 94.2278(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.7872(2)
_cell_length_b                   5.02626(11)
_cell_length_c                   15.5479(3)
_cell_measurement_reflns_used    8805
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.5610
_cell_measurement_theta_min      4.1150
_cell_volume                     840.70(3)
_computing_cell_refinement
;
CrysAlisPro 1.171.39.32a (Rigaku OD, 2017) [2]
;
_computing_data_collection
;
CrysAlisPro 1.171.39.32a (Rigaku OD, 2017) [2]
;
_computing_data_reduction
;
CrysAlisPro 1.171.39.32a (Rigaku OD, 2017) [2]
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009) [5]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015) [4]'
_computing_structure_solution    'Superflip [3]'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4674
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -129.00 -53.00   1.00    1.00    --  -41.95 178.00  90.00   76
  2  ω     17.00 116.00   1.00    1.00    --   41.95  38.00 -30.00   99
  3  ω     35.00 131.00   1.00    1.00    --   41.95 178.00-180.00   96
  4  ω      1.00 122.00   1.00    1.00    --   41.95  19.00  90.00  121
  5  ω     67.00 166.00   1.00    1.10    --   92.50  45.00-150.00   99
  6  ω      9.00 129.00   1.00    1.10    --   92.50 -89.00 -68.52  120
  7  ω     10.00  84.00   1.00    1.10    --   92.50 -95.00 -90.00   74
  8  ω     20.00 122.00   1.00    1.10    --   92.50 -61.00  60.00  102
  9  ω      9.00 131.00   1.00    1.10    --   92.50 -92.00 136.49  122
 10  ω     63.00 165.00   1.00    1.10    --   92.50  61.00-120.00  102
 11  ω     20.00 122.00   1.00    1.10    --   92.50 -61.00 -60.00  102
 12  ω     10.00  84.00   1.00    1.10    --   92.50 -95.00-180.00   74
 13  ω      9.00 130.00   1.00    1.10    --   92.50 -90.00-146.34  121
 14  ω     11.00 145.00   1.00    1.10    --   92.50 -15.00-120.00  134
 15  ω     10.00  84.00   1.00    1.10    --   92.50 -95.00  30.00   74
 16  ω     16.00 125.00   1.00    1.10    --   92.50 -77.00-180.00  109
 17  ω     40.00 174.00   1.00    1.10    --   92.50  15.00-180.00  134
 18  ω     63.00 165.00   1.00    1.10    --   92.50  61.00   0.00  102
 19  ω     10.00  84.00   1.00    1.10    --   92.50 -95.00  60.00   74
 20  ω     73.00 166.00   1.00    1.10    --   92.50 125.00-120.00   93
 21  ω     67.00 166.00   1.00    1.10    --   92.50  45.00-180.00   99
 22  ω     73.00 166.00   1.00    1.10    --   92.50 125.00 -30.00   93
 23  ω      9.00 118.00   1.00    1.00    --   41.95  77.00 150.00  109
 24  ω     23.00 133.00   1.00    1.00    --   56.00  78.00-153.20  110
 25  ω     31.00 141.00   1.00    1.00    --   64.00  78.00  77.45  110
 26  ω     32.00 140.00   1.00    1.00    --   64.00  76.00 -47.90  108
 27  ω     35.00 145.00   1.00    1.10    --   68.00  79.00 142.39  110
 28  ω     35.00 145.00   1.00    1.10    --   68.00  78.00-112.94  110
 29  ω     39.00 149.00   1.00    1.10    --   72.00  78.00 -25.88  110
 30  ω     39.00 149.00   1.00    1.10    --   72.00  79.00  36.08  110
 31  ω     46.00 149.00   1.00    1.10    --   76.00  66.00 114.97  103
 32  ω     63.00 165.00   1.00    1.10    --   92.50  61.00 120.00  102
 33  ω     63.00 165.00   1.00    1.10    --   92.50  61.00 -90.00  102
 34  ω     63.00 165.00   1.00    1.10    --   92.50  61.00 -60.00  102
 35  ω     63.00 165.00   1.00    1.10    --   92.50  61.00  60.00  102
 36  ω     60.00 169.00   1.00    1.10    --   92.50  77.00-180.00  109
 37  ω     60.00 150.00   1.00    1.10    --   92.50  77.00  60.00   90
 38  ω     63.00 165.00   1.00    1.10    --   92.50  61.00 150.00  102
 39  ω     63.00 165.00   1.00    1.10    --   92.50  61.00 -30.00  102
 40  ω     60.00 169.00   1.00    1.10    --   92.50  77.00   0.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1409832000
_diffrn_orient_matrix_UB_12      -0.0367978000
_diffrn_orient_matrix_UB_13      0.0050659000
_diffrn_orient_matrix_UB_21      -0.0103656000
_diffrn_orient_matrix_UB_22      -0.1108649000
_diffrn_orient_matrix_UB_23      -0.0926538000
_diffrn_orient_matrix_UB_31      0.0224741000
_diffrn_orient_matrix_UB_32      -0.2834360000
_diffrn_orient_matrix_UB_33      0.0355773000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24014
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.887
_diffrn_reflns_theta_max         66.887
_diffrn_reflns_theta_min         4.109
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.218
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
 Flack x determined using 1037 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(9)
_refine_ls_extinction_coef       0.0053(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2949
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0337
_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)+(0.0409P)²+0.1216P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2650
_reflns_number_total             2949
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0219_suppl.cif
_cod_data_source_block           exp_567
_cod_database_code               8105561
_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.
;
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
O1 O 0.93691(16) -0.0318(4) 0.78192(13) 0.0573(5) Uani 1 1 d . . . . .
O3 O 1.20050(17) 0.3403(3) 0.56779(10) 0.0564(5) Uani 1 1 d . . . . .
O4 O 1.1616(2) 0.6900(4) 0.65359(13) 0.0664(6) Uani 1 1 d . . . . .
N2 N 1.12537(18) 0.2669(4) 0.69396(12) 0.0470(5) Uani 1 1 d . . . . .
H2 H 1.1308 0.1018 0.6802 0.056 Uiso 1 1 calc R . . . .
O2 O 1.12205(17) 0.2756(4) 0.93128(11) 0.0656(5) Uani 1 1 d . . . . .
C8 C 0.9496(2) 0.2114(5) 0.78138(14) 0.0416(5) Uani 1 1 d . . . . .
C12 C 1.1619(2) 0.4537(5) 0.63973(15) 0.0443(6) Uani 1 1 d . . . . .
N1 N 0.85488(17) 0.3803(4) 0.78451(13) 0.0496(5) Uani 1 1 d . . . . .
H1 H 0.8690 0.5487 0.7849 0.060 Uiso 1 1 calc R . . . .
C9 C 1.0770(2) 0.3382(5) 0.77528(14) 0.0423(5) Uani 1 1 d . . . . .
H9 H 1.0692 0.5321 0.7787 0.051 Uiso 1 1 calc R . . . .
C1 C 0.6416(2) 0.4921(6) 0.81831(16) 0.0511(6) Uani 1 1 d . . . . .
C2 C 0.6622(3) 0.6066(6) 0.89848(17) 0.0595(7) Uani 1 1 d . . . . .
H2A H 0.7322 0.5592 0.9336 0.071 Uiso 1 1 calc R . . . .
C10 C 1.1665(2) 0.2404(6) 0.84898(15) 0.0534(6) Uani 1 1 d . . . . .
H10A H 1.1828 0.0528 0.8405 0.064 Uiso 1 1 calc R . . . .
H10B H 1.2447 0.3347 0.8470 0.064 Uiso 1 1 calc R . . . .
C13 C 1.2393(3) 0.5104(6) 0.49688(16) 0.0567(7) Uani 1 1 d . . . . .
C7 C 0.7278(2) 0.2844(7) 0.7872(2) 0.0682(8) Uani 1 1 d . . . . .
H7A H 0.7274 0.1311 0.8251 0.082 Uiso 1 1 calc R . . . .
H7B H 0.6974 0.2272 0.7299 0.082 Uiso 1 1 calc R . . . .
C6 C 0.5369(3) 0.5676(8) 0.76782(19) 0.0717(8) Uani 1 1 d . . . . .
H6 H 0.5211 0.4940 0.7132 0.086 Uiso 1 1 calc R . . . .
C3 C 0.5802(3) 0.7909(7) 0.92735(19) 0.0686(8) Uani 1 1 d . . . . .
H3 H 0.5955 0.8668 0.9816 0.082 Uiso 1 1 calc R . . . .
C5 C 0.4551(3) 0.7527(9) 0.7979(3) 0.0875(11) Uani 1 1 d . . . . .
H5 H 0.3846 0.8016 0.7635 0.105 Uiso 1 1 calc R . . . .
C4 C 0.4770(3) 0.8626(7) 0.8770(2) 0.0781(10) Uani 1 1 d . . . . .
H4 H 0.4218 0.9865 0.8969 0.094 Uiso 1 1 calc R . . . .
C16 C 1.3534(3) 0.6659(8) 0.5278(2) 0.0862(12) Uani 1 1 d . . . . .
H16A H 1.3309 0.8018 0.5671 0.129 Uiso 1 1 calc GR . . . .
H16B H 1.3889 0.7467 0.4793 0.129 Uiso 1 1 calc GR . . . .
H16C H 1.4131 0.5484 0.5565 0.129 Uiso 1 1 calc GR . . . .
C11 C 1.1195(3) 0.5447(8) 0.9584(2) 0.0795(9) Uani 1 1 d . . . . .
H11A H 1.0580 0.6402 0.9228 0.119 Uiso 1 1 calc GR . . . .
H11B H 1.1996 0.6238 0.9533 0.119 Uiso 1 1 calc GR . . . .
H11C H 1.0991 0.5524 1.0174 0.119 Uiso 1 1 calc GR . . . .
C14 C 1.1332(3) 0.6807(7) 0.4626(2) 0.0736(9) Uani 1 1 d . . . . .
H14A H 1.0603 0.5725 0.4518 0.110 Uiso 1 1 calc GR . . . .
H14B H 1.1537 0.7633 0.4098 0.110 Uiso 1 1 calc GR . . . .
H14C H 1.1174 0.8155 0.5042 0.110 Uiso 1 1 calc GR . . . .
C15 C 1.2724(6) 0.3089(8) 0.4294(2) 0.132(2) Uani 1 1 d . . . . .
H15A H 1.3332 0.1868 0.4545 0.197 Uiso 1 1 calc GR . . . .
H15B H 1.3057 0.3998 0.3820 0.197 Uiso 1 1 calc GR . . . .
H15C H 1.1991 0.2126 0.4091 0.197 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C12 O3 C13 119.71(19) . .
C12 N2 C9 121.2(2) . .
C10 O2 C11 113.9(2) . .
O1 C8 N1 123.2(2) . .
O1 C8 C9 121.1(2) . .
N1 C8 C9 115.7(2) . .
O4 C12 O3 124.7(2) . .
O4 C12 N2 124.9(2) . .
N2 C12 O3 110.4(2) . .
C8 N1 C7 121.1(2) . .
N2 C9 C8 109.62(18) . .
N2 C9 C10 109.09(18) . .
C8 C9 C10 110.04(19) . .
C2 C1 C7 121.3(2) . .
C2 C1 C6 118.1(3) . .
C6 C1 C7 120.6(3) . .
C1 C2 C3 120.8(3) . .
O2 C10 C9 113.72(19) . .
O3 C13 C16 109.4(2) . .
O3 C13 C14 110.2(2) . .
O3 C13 C15 102.9(2) . .
C16 C13 C15 109.8(3) . .
C14 C13 C16 113.7(3) . .
C14 C13 C15 110.4(3) . .
N1 C7 C1 112.7(2) . .
C1 C6 C5 120.5(3) . .
C4 C3 C2 120.5(3) . .
C4 C5 C6 120.5(3) . .
C5 C4 C3 119.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C8 1.230(3) .
O3 C12 1.348(3) .
O3 C13 1.480(3) .
O4 C12 1.207(3) .
N2 C12 1.340(3) .
N2 C9 1.448(3) .
O2 C10 1.410(3) .
O2 C11 1.418(4) .
C8 N1 1.332(3) .
C8 C9 1.524(3) .
N1 C7 1.457(3) .
C9 C10 1.525(3) .
C1 C2 1.376(4) .
C1 C7 1.501(4) .
C1 C6 1.380(4) .
C2 C3 1.378(4) .
C13 C16 1.506(4) .
C13 C14 1.496(4) .
C13 C15 1.519(4) .
C6 C5 1.387(5) .
C3 C4 1.361(4) .
C5 C4 1.353(5) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O4 0.86 2.14 2.999(3) 174.3 1_545
N1 H1 O1 0.86 2.23 3.086(3) 170.8 1_565
C9 H9 O4 0.98 2.39 2.792(3) 104.1 .
C16 H16A O4 0.96 2.41 2.953(4) 115.3 .
C14 H14C O4 0.96 2.42 2.963(4) 115.5 .
