#------------------------------------------------------------------------------
#$Date: 2022-03-07 12:14:05 +0200 (Mon, 07 Mar 2022) $
#$Revision: 273501 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/46/8104673.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_8104673
loop_
_publ_author_name
'Manana, Pholani'
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of di-tert-butyl dicarbonate, C10H18O5
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1087
_journal_page_last               1089
_journal_paper_doi               10.1515/ncrs-2021-0228
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C10 H18 O5'
_chemical_formula_sum            'C10 H18 O5'
_chemical_formula_weight         218.24
_chemical_name_common            'di-tert-butyl dicarbonate'
_chemical_name_systematic        'di-tert-butyl dicarbonate'
_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     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 116.087(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3561(7)
_cell_length_b                   11.4569(7)
_cell_length_c                   10.9762(6)
_cell_measurement_reflns_used    5420
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.67
_cell_volume                     1282.59(13)
_computing_cell_refinement       'SAINT [1]'
_computing_data_collection       'APEX2 [1]'
_computing_data_reduction        'SAINT [1]'
_computing_molecular_graphics    'ORTEP3 [3], Mercury [4]'
_computing_publication_material  'SHELXL-97 [2], PLATON [5]'
_computing_structure_refinement  'SHELXL-97 [2]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11805
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.313
_diffrn_reflns_theta_min         1.997
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9282
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS[6]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.584
_exptl_crystal_size_mid          0.432
_exptl_crystal_size_min          0.376
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3182
_refine_ls_number_restraints     133
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0547
_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)+(0.082100P)²+0.238600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1677
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2386
_reflns_number_total             3182
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0228_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        1282.58(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8104673
_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.52863(15) 0.40516(15) 0.76473(17) 0.0618(4) Uani 1 1 d D . . . .
C2 C 0.5373(2) 0.3373(2) 0.8852(2) 0.0955(7) Uani 1 1 d . . . . .
H2A H 0.602527 0.275066 0.905995 0.143 Uiso 1 1 calc R U . . .
H2B H 0.451652 0.302985 0.864812 0.143 Uiso 1 1 calc R U . . .
H2C H 0.563527 0.389595 0.963441 0.143 Uiso 1 1 calc R U . . .
C3 C 0.6564(3) 0.4691(3) 0.7976(4) 0.1295(11) Uani 1 1 d . . . . .
H3A H 0.728741 0.412841 0.828337 0.194 Uiso 1 1 calc R U . . .
H3B H 0.672335 0.526404 0.869456 0.194 Uiso 1 1 calc R U . . .
H3C H 0.650420 0.509189 0.716236 0.194 Uiso 1 1 calc R U . . .
C4 C 0.4893(3) 0.3307(2) 0.6404(2) 0.0945(7) Uani 1 1 d . . . . .
H4A H 0.558053 0.272942 0.655477 0.142 Uiso 1 1 calc R U . . .
H4B H 0.477248 0.380044 0.562836 0.142 Uiso 1 1 calc R U . . .
H4C H 0.406965 0.290390 0.621608 0.142 Uiso 1 1 calc R U . . .
C7 C -0.00964(14) 0.75511(15) 0.68634(15) 0.0575(4) Uani 1 1 d D . . . .
C8 C 0.06147(18) 0.81784(17) 0.82089(17) 0.0696(5) Uani 1 1 d . . . . .
H8A H -0.001432 0.864227 0.839283 0.104 Uiso 1 1 calc R U . . .
H8B H 0.128511 0.869420 0.816858 0.104 Uiso 1 1 calc R U . . .
H8C H 0.103285 0.760391 0.893454 0.104 Uiso 1 1 calc R U . . .
C9 C -0.1066(2) 0.66714(19) 0.6889(2) 0.0805(5) Uani 1 1 d . . . . .
H9A H -0.180418 0.707761 0.693531 0.121 Uiso 1 1 calc R U . A 2
H9B H -0.063860 0.616630 0.768449 0.121 Uiso 1 1 calc R U . A 2
H9C H -0.138662 0.619613 0.606289 0.121 Uiso 1 1 calc R U . A 2
C10 C -0.0730(2) 0.8400(2) 0.5704(2) 0.0873(6) Uani 1 1 d . . . . .
H10A H -0.142392 0.883038 0.581133 0.131 Uiso 1 1 calc R U . . .
H10B H -0.110742 0.797090 0.484426 0.131 Uiso 1 1 calc R U . . .
H10C H -0.006851 0.894976 0.570410 0.131 Uiso 1 1 calc R U . . .
O1A O 0.43765(13) 0.50715(11) 0.73432(17) 0.0555(4) Uani 0.851(3) 1 d D . P B 1
O2A O 0.25815(15) 0.40045(13) 0.6966(2) 0.0818(6) Uani 0.851(3) 1 d D . P B 1
O3A O 0.2532(2) 0.59567(17) 0.6721(3) 0.0692(5) Uani 0.851(3) 1 d D . P B 1
O4A O 0.17181(14) 0.57709(12) 0.82467(14) 0.0658(4) Uani 0.851(3) 1 d D . P B 1
O5A O 0.09014(15) 0.70265(12) 0.64805(14) 0.0541(4) Uani 0.851(3) 1 d D . P B 1
C5A C 0.3147(4) 0.4878(3) 0.7046(5) 0.0556(6) Uani 0.851(3) 1 d D . P B 1
C6A C 0.1668(3) 0.6206(2) 0.7246(4) 0.0499(8) Uani 0.851(3) 1 d D . P B 1
O1B O 0.3916(9) 0.4374(9) 0.7597(10) 0.066(3) Uani 0.122(2) 1 d D . P B 2
O2B O 0.3397(10) 0.5534(10) 0.5778(11) 0.077(3) Uani 0.122(2) 1 d D . P B 2
O3B O 0.2003(9) 0.5234(8) 0.6676(13) 0.078(3) Uani 0.122(2) 1 d D . P B 2
O4B O 0.2330(8) 0.7173(7) 0.6996(10) 0.061(2) Uani 0.122(2) 1 d D . P B 2
O5B O 0.0433(7) 0.6268(7) 0.6669(9) 0.052(2) Uani 0.122(2) 1 d D . P B 2
C5B C 0.3226(14) 0.5105(14) 0.6679(17) 0.050(3) Uani 0.122(2) 1 d D . P B 2
C6B C 0.1670(17) 0.6332(14) 0.689(3) 0.052(6) Uani 0.122(2) 1 d D . P B 2
O1C O 0.413(2) 0.486(3) 0.676(3) 0.040(5) Uani 0.027(2) 1 d D . P B 3
O2C O 0.292(3) 0.425(3) 0.777(4) 0.040(5) Uani 0.027(2) 1 d D . P B 3
O3C O 0.262(3) 0.601(3) 0.666(5) 0.040(5) Uani 0.027(2) 1 d D . P B 3
O4C O 0.046(2) 0.550(3) 0.568(3) 0.040(5) Uani 0.027(2) 1 d D . P B 3
O5C O 0.1257(18) 0.701(3) 0.710(4) 0.040(5) Uani 0.027(2) 1 d D . P B 3
C5C C 0.312(7) 0.488(5) 0.702(9) 0.040(5) Uani 0.027(2) 1 d D . P B 3
C6C C 0.133(2) 0.613(3) 0.636(4) 0.040(5) Uani 0.027(2) 1 d D . P B 3
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'
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
O1A C1 C2 111.89(15) . .
O1A C1 C4 109.92(14) . .
C2 C1 C4 112.64(19) . .
O1A C1 C3 99.79(17) . .
C2 C1 C3 110.8(2) . .
C4 C1 C3 111.1(2) . .
C2 C1 O1C 124.9(10) . .
C4 C1 O1C 86.2(14) . .
C3 C1 O1C 108.7(13) . .
C2 C1 O1B 80.4(4) . .
C4 C1 O1B 101.9(4) . .
C3 C1 O1B 136.0(4) . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C1 C3 H3A 109.5 . .
C1 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
C1 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
C1 C4 H4A 109.5 . .
C1 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C1 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
O5A C7 C9 112.78(14) . .
O5A C7 C10 99.26(13) . .
C9 C7 C10 111.52(16) . .
O5A C7 C8 108.60(13) . .
C9 C7 C8 112.38(14) . .
C10 C7 C8 111.58(15) . .
C9 C7 O5C 113.8(14) . .
C10 C7 O5C 117.7(16) . .
C8 C7 O5C 87.8(10) . .
C9 C7 O5B 73.4(3) . .
C10 C7 O5B 122.3(3) . .
C8 C7 O5B 118.9(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 O5B 56.6(2) . .
C7 C9 H9A 109.5 . .
O5B C9 H9A 165.5 . .
C7 C9 H9B 109.5 . .
O5B C9 H9B 81.2 . .
H9A C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
O5B C9 H9C 74.6 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C7 C10 H10A 109.5 . .
C7 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C7 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C5A O1A C1 118.71(18) . .
C6A O3A C5A 116.8(2) . .
C6A O5A C7 118.77(18) . .
O2A C5A O1A 130.9(3) . .
O2A C5A O3A 123.0(3) . .
O1A C5A O3A 105.9(3) . .
O4A C6A O5A 130.2(2) . .
O4A C6A O3A 123.5(3) . .
O5A C6A O3A 106.1(3) . .
C5B O1B C1 115.7(9) . .
C6B O3B C5B 116.6(12) . .
C6B O5B C7 110.4(8) . .
C6B O5B C9 156.2(11) . .
C7 O5B C9 50.0(2) . .
O2B C5B O1B 130.9(13) . .
O2B C5B O3B 118.6(12) . .
O1B C5B O3B 109.6(11) . .
O4B C6B O5B 129.4(14) . .
O4B C6B O3B 123.5(13) . .
O5B C6B O3B 105.7(11) . .
C5C O1C C1 117(3) . .
C6C O3C C5C 116(3) . .
C6C O4C O4C 157(3) . 3_566
C6C O5C C7 121.4(19) . .
O2C C5C O1C 127(3) . .
O2C C5C O3C 125(4) . .
O1C C5C O3C 104(2) . .
O4C C6C O5C 126(2) . .
O4C C6C O3C 127(2) . .
O5C C6C O3C 107(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1A 1.497(2) .
C1 C2 1.499(3) .
C1 C4 1.502(3) .
C1 C3 1.520(3) .
C1 O1C 1.553(15) .
C1 O1B 1.577(8) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C7 O5A 1.4969(18) .
C7 C9 1.502(3) .
C7 C10 1.509(2) .
C7 C8 1.517(2) .
C7 O5C 1.569(15) .
C7 O5B 1.637(7) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 O5B 1.878(7) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
O1A C5A 1.306(3) .
O2A C5A 1.171(4) .
O3A C6A 1.369(3) .
O3A C5A 1.387(3) .
O4A C6A 1.184(4) .
O5A C6A 1.306(3) .
O1B C5B 1.279(13) .
O2B C5B 1.195(13) .
O3B C6B 1.363(15) .
O3B C5B 1.395(14) .
O4B C6B 1.194(15) .
O5B C6B 1.319(14) .
O1C C5C 1.297(17) .
O2C C5C 1.185(19) .
O3C C6C 1.359(17) .
O3C C5C 1.395(18) .
O4C C6C 1.189(17) .
O4C O4C 1.81(5) 3_566
O5C C6C 1.316(17) .
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
C3 H3A O4B^b 0.98 2.33 3.141(9) 140 2_646
C4 H4A O4B^b 0.98 2.29 3.138(10) 144 2_646
C10 H10A O4A^a 0.98 2.54 3.332(3) 138 2_556
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C10 C7 C9 O5B 118.8(3) . . . .
C8 C7 C9 O5B -115.0(3) . . . .
C2 C1 O1A C5A -60.7(3) . . . .
C4 C1 O1A C5A 65.2(3) . . . .
C3 C1 O1A C5A -177.9(3) . . . .
C9 C7 O5A C6A -60.8(3) . . . .
C10 C7 O5A C6A -178.9(2) . . . .
C8 C7 O5A C6A 64.5(2) . . . .
C1 O1A C5A O2A 0.0(6) . . . .
C1 O1A C5A O3A -175.8(2) . . . .
C6A O3A C5A O2A 47.4(6) . . . .
C6A O3A C5A O1A -136.4(3) . . . .
C7 O5A C6A O4A 0.4(5) . . . .
C7 O5A C6A O3A -175.55(19) . . . .
C5A O3A C6A O4A 24.9(5) . . . .
C5A O3A C6A O5A -158.8(3) . . . .
C2 C1 O1B C5B 176.4(13) . . . .
C4 C1 O1B C5B -72.3(13) . . . .
C3 C1 O1B C5B 66.3(14) . . . .
C9 C7 O5B C6B -164.2(15) . . . .
C10 C7 O5B C6B 90.5(15) . . . .
C8 C7 O5B C6B -57.4(16) . . . .
C10 C7 O5B C9 -105.3(3) . . . .
C8 C7 O5B C9 106.8(2) . . . .
C7 C9 O5B C6B 39(3) . . . .
C1 O1B C5B O2B 6(3) . . . .
C1 O1B C5B O3B 175.0(10) . . . .
C6B O3B C5B O2B -68(3) . . . .
C6B O3B C5B O1B 121(2) . . . .
C7 O5B C6B O4B -12(4) . . . .
C9 O5B C6B O4B -43(6) . . . .
C7 O5B C6B O3B -178.8(14) . . . .
C9 O5B C6B O3B 150.2(19) . . . .
C5B O3B C6B O4B 5(4) . . . .
C5B O3B C6B O5B 172.1(15) . . . .
C2 C1 O1C C5C -5(6) . . . .
C4 C1 O1C C5C 110(6) . . . .
C3 C1 O1C C5C -139(6) . . . .
C9 C7 O5C C6C 54(5) . . . .
C10 C7 O5C C6C -80(4) . . . .
C8 C7 O5C C6C 167(4) . . . .
C1 O1C C5C O2C -10(13) . . . .
C1 O1C C5C O3C 150(5) . . . .
C6C O3C C5C O2C -44(12) . . . .
C6C O3C C5C O1C 156(5) . . . .
O4C O4C C6C O5C 156(8) 3_566 . . .
O4C O4C C6C O3C -33(14) 3_566 . . .
C7 O5C C6C O4C -17(8) . . . .
C7 O5C C6C O3C 170(3) . . . .
C5C O3C C6C O4C -44(9) . . . .
C5C O3C C6C O5C 128(6) . . . .
