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#$Date: 2022-06-24 10:29:28 +0300 (Fri, 24 Jun 2022) $
#$Revision: 276227 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/54/8105496.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_8105496
loop_
_publ_author_name
'Li, Wu-Wu'
'Liu, Xiong-Li'
_publ_section_title
;
 Synthesis and crystal structure of methyl
 2-(2-((tert-butoxycarbonyl)amino)phenyl)-2-(4-oxo-4H-chromen-3-yl)acetate,
 C23H23NO6
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1465
_journal_page_last               1467
_journal_paper_doi               10.1515/ncrs-2020-0360
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C23 H23 N O6'
_chemical_formula_sum            'C23 H23 N O6'
_chemical_formula_weight         409.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 98.753(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5845(4)
_cell_length_b                   14.7024(5)
_cell_length_c                   18.1433(6)
_cell_measurement_reflns_used    5490
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      2.6630
_cell_measurement_theta_min      29.0380
_cell_volume                     1999.60(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12760
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.271
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3510
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0389
_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)+(0.0433P)²+0.6984P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0965
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2963
_reflns_number_total             3510
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0360_suppl.cif
_cod_data_source_block           I
_cod_original_cell_volume        1999.62(14)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8105496
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O 0.71916(17) 0.66626(8) 0.54853(6) 0.0256(3) Uani 1 1 d . . . . .
O2 O 0.58388(16) 0.50290(7) 0.36722(6) 0.0221(3) Uani 1 1 d . . . . .
O3 O 0.85285(15) 0.66269(7) 0.23708(6) 0.0217(3) Uani 1 1 d . . . . .
O4 O 0.57052(17) 0.66172(8) 0.17288(6) 0.0293(3) Uani 1 1 d . . . . .
O5 O 0.83680(15) 0.79430(7) 0.42312(6) 0.0210(3) Uani 1 1 d . . . . .
O6 O 0.66384(16) 0.87639(7) 0.48784(6) 0.0227(3) Uani 1 1 d . . . . .
N1 N 0.65063(19) 0.75055(9) 0.27585(7) 0.0179(3) Uani 1 1 d . . . . .
H1 H 0.734(3) 0.7555(12) 0.3139(10) 0.026(5) Uiso 1 1 d . . . . .
C1 C 0.5813(2) 0.64917(10) 0.42435(8) 0.0172(3) Uani 1 1 d . . . . .
C2 C 0.6808(2) 0.61601(11) 0.49421(8) 0.0186(4) Uani 1 1 d . . . . .
C3 C 0.7328(2) 0.51983(10) 0.49408(9) 0.0190(4) Uani 1 1 d . . . . .
C4 C 0.8356(2) 0.47897(11) 0.55594(9) 0.0225(4) Uani 1 1 d . . . . .
H4 H 0.866215 0.511965 0.599754 0.027 Uiso 1 1 calc R U . . .
C5 C 0.8915(2) 0.39057(11) 0.55227(10) 0.0252(4) Uani 1 1 d . . . . .
H5 H 0.958815 0.363678 0.593681 0.030 Uiso 1 1 calc R U . . .
C6 C 0.8474(2) 0.34096(11) 0.48651(10) 0.0270(4) Uani 1 1 d . . . . .
H6 H 0.888454 0.281598 0.484023 0.032 Uiso 1 1 calc R U . . .
C7 C 0.7443(2) 0.37865(11) 0.42545(10) 0.0246(4) Uani 1 1 d . . . . .
H7 H 0.713567 0.345126 0.381914 0.030 Uiso 1 1 calc R U . . .
C8 C 0.6864(2) 0.46806(11) 0.42995(9) 0.0203(4) Uani 1 1 d . . . . .
C9 C 0.5358(2) 0.59178(10) 0.36736(9) 0.0192(4) Uani 1 1 d . . . . .
H9 H 0.466020 0.614490 0.324735 0.023 Uiso 1 1 calc R U . . .
C10 C 0.5288(2) 0.74868(10) 0.42356(8) 0.0169(3) Uani 1 1 d . . . . .
H10 H 0.455981 0.756679 0.463304 0.020 Uiso 1 1 calc R U . . .
C11 C 0.4180(2) 0.78384(10) 0.35211(8) 0.0168(3) Uani 1 1 d . . . . .
C12 C 0.2487(2) 0.81868(10) 0.35582(9) 0.0198(4) Uani 1 1 d . . . . .
H12 H 0.208232 0.820904 0.401665 0.024 Uiso 1 1 calc R U . . .
C13 C 0.1397(2) 0.84994(11) 0.29313(9) 0.0232(4) Uani 1 1 d . . . . .
H13 H 0.026853 0.872607 0.296762 0.028 Uiso 1 1 calc R U . . .
C14 C 0.1994(2) 0.84735(11) 0.22476(9) 0.0231(4) Uani 1 1 d . . . . .
H14 H 0.125814 0.867670 0.182244 0.028 Uiso 1 1 calc R U . . .
C15 C 0.3676(2) 0.81477(10) 0.21935(9) 0.0203(4) Uani 1 1 d . . . . .
H15 H 0.407425 0.814028 0.173337 0.024 Uiso 1 1 calc R U . . .
C16 C 0.4780(2) 0.78301(10) 0.28248(8) 0.0169(3) Uani 1 1 d . . . . .
C17 C 0.6812(2) 0.68863(10) 0.22313(8) 0.0191(4) Uani 1 1 d . . . . .
C18 C 0.9195(2) 0.59164(11) 0.19078(9) 0.0221(4) Uani 1 1 d . . . . .
C19 C 0.8202(3) 0.50357(12) 0.19828(10) 0.0320(4) Uani 1 1 d . . . . .
H19A H 0.825584 0.488844 0.250127 0.048 Uiso 1 1 calc R U . . .
H19B H 0.874252 0.455578 0.173631 0.048 Uiso 1 1 calc R U . . .
H19C H 0.697907 0.510445 0.175849 0.048 Uiso 1 1 calc R U . . .
C20 C 1.1134(2) 0.58349(12) 0.22529(10) 0.0297(4) Uani 1 1 d . . . . .
H20A H 1.171759 0.640985 0.222080 0.044 Uiso 1 1 calc R U . . .
H20B H 1.170553 0.538205 0.199009 0.044 Uiso 1 1 calc R U . . .
H20C H 1.120931 0.566125 0.276683 0.044 Uiso 1 1 calc R U . . .
C21 C 0.9039(3) 0.62367(13) 0.11039(9) 0.0324(5) Uani 1 1 d . . . . .
H21A H 0.780515 0.633111 0.090568 0.049 Uiso 1 1 calc R U . . .
H21B H 0.953218 0.578433 0.081280 0.049 Uiso 1 1 calc R U . . .
H21C H 0.968047 0.679706 0.108556 0.049 Uiso 1 1 calc R U . . .
C22 C 0.6954(2) 0.80687(10) 0.44475(8) 0.0174(4) Uani 1 1 d . . . . .
C23 C 0.8152(3) 0.93334(12) 0.51410(10) 0.0305(4) Uani 1 1 d . . . . .
H23A H 0.868786 0.953831 0.472420 0.046 Uiso 1 1 calc R U . . .
H23B H 0.900902 0.899176 0.547457 0.046 Uiso 1 1 calc R U . . .
H23C H 0.776575 0.984913 0.539903 0.046 Uiso 1 1 calc R U . . .
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
C9 O2 C8 118.37(12) . .
C17 O3 C18 119.95(12) . .
C22 O6 C23 115.77(13) . .
C17 N1 C16 122.83(15) . .
C17 N1 H1 115.7(12) . .
C16 N1 H1 118.5(12) . .
C9 C1 C2 119.98(14) . .
C9 C1 C10 124.38(14) . .
C2 C1 C10 115.57(13) . .
O1 C2 C1 121.59(14) . .
O1 C2 C3 123.27(15) . .
C1 C2 C3 115.13(14) . .
C8 C3 C4 118.35(15) . .
C8 C3 C2 119.66(14) . .
C4 C3 C2 121.93(15) . .
C5 C4 C3 120.39(16) . .
C5 C4 H4 119.8 . .
C3 C4 H4 119.8 . .
C4 C5 C6 120.09(16) . .
C4 C5 H5 120.0 . .
C6 C5 H5 120.0 . .
C7 C6 C5 120.82(16) . .
C7 C6 H6 119.6 . .
C5 C6 H6 119.6 . .
C6 C7 C8 118.68(16) . .
C6 C7 H7 120.7 . .
C8 C7 H7 120.7 . .
O2 C8 C3 121.85(14) . .
O2 C8 C7 116.51(14) . .
C3 C8 C7 121.63(15) . .
C1 C9 O2 124.80(15) . .
C1 C9 H9 117.6 . .
O2 C9 H9 117.6 . .
C1 C10 C11 116.45(13) . .
C1 C10 C22 109.43(13) . .
C11 C10 C22 110.64(12) . .
C1 C10 H10 106.6 . .
C11 C10 H10 106.6 . .
C22 C10 H10 106.6 . .
C12 C11 C16 118.23(15) . .
C12 C11 C10 118.46(13) . .
C16 C11 C10 123.31(14) . .
C13 C12 C11 121.59(14) . .
C13 C12 H12 119.2 . .
C11 C12 H12 119.2 . .
C12 C13 C14 119.53(16) . .
C12 C13 H13 120.2 . .
C14 C13 H13 120.2 . .
C15 C14 C13 120.36(16) . .
C15 C14 H14 119.8 . .
C13 C14 H14 119.8 . .
C14 C15 C16 120.30(15) . .
C14 C15 H15 119.9 . .
C16 C15 H15 119.9 . .
C15 C16 C11 119.98(15) . .
C15 C16 N1 119.41(14) . .
C11 C16 N1 120.60(14) . .
O4 C17 O3 126.26(14) . .
O4 C17 N1 125.05(16) . .
O3 C17 N1 108.68(14) . .
O3 C18 C20 102.46(13) . .
O3 C18 C19 109.63(13) . .
C20 C18 C19 111.12(14) . .
O3 C18 C21 110.07(13) . .
C20 C18 C21 110.51(14) . .
C19 C18 C21 112.58(15) . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C18 C20 H20A 109.5 . .
C18 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C18 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C18 C21 H21A 109.5 . .
C18 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C18 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
O5 C22 O6 123.72(15) . .
O5 C22 C10 124.96(14) . .
O6 C22 C10 111.25(13) . .
O6 C23 H23A 109.5 . .
O6 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
O6 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.2307(19) .
O2 C9 1.3569(19) .
O2 C8 1.3760(19) .
O3 C17 1.343(2) .
O3 C18 1.4769(18) .
O4 C17 1.208(2) .
O5 C22 1.2107(19) .
O6 C22 1.3306(18) .
O6 C23 1.442(2) .
N1 C17 1.366(2) .
N1 C16 1.416(2) .
N1 H1 0.87(2) .
C1 C9 1.338(2) .
C1 C2 1.457(2) .
C1 C10 1.516(2) .
C2 C3 1.468(2) .
C3 C8 1.390(2) .
C3 C4 1.401(2) .
C4 C5 1.372(2) .
C4 H4 0.9300 .
C5 C6 1.395(2) .
C5 H5 0.9300 .
C6 C7 1.372(2) .
C6 H6 0.9300 .
C7 C8 1.392(2) .
C7 H7 0.9300 .
C9 H9 0.9300 .
C10 C11 1.524(2) .
C10 C22 1.526(2) .
C10 H10 0.9800 .
C11 C12 1.394(2) .
C11 C16 1.406(2) .
C12 C13 1.379(2) .
C12 H12 0.9300 .
C13 C14 1.384(2) .
C13 H13 0.9300 .
C14 C15 1.380(2) .
C14 H14 0.9300 .
C15 C16 1.393(2) .
C15 H15 0.9300 .
C18 C20 1.513(3) .
C18 C19 1.514(2) .
C18 C21 1.520(2) .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
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
C9 C1 C2 O1 -177.37(15) . . . .
C10 C1 C2 O1 -0.2(2) . . . .
C9 C1 C2 C3 3.5(2) . . . .
C10 C1 C2 C3 -179.28(13) . . . .
O1 C2 C3 C8 -179.01(15) . . . .
C1 C2 C3 C8 0.1(2) . . . .
O1 C2 C3 C4 -2.0(2) . . . .
C1 C2 C3 C4 177.16(14) . . . .
C8 C3 C4 C5 1.3(2) . . . .
C2 C3 C4 C5 -175.82(15) . . . .
C3 C4 C5 C6 0.6(2) . . . .
C4 C5 C6 C7 -1.7(3) . . . .
C5 C6 C7 C8 1.0(3) . . . .
C9 O2 C8 C3 3.6(2) . . . .
C9 O2 C8 C7 -175.24(14) . . . .
C4 C3 C8 O2 179.16(14) . . . .
C2 C3 C8 O2 -3.7(2) . . . .
C4 C3 C8 C7 -2.0(2) . . . .
C2 C3 C8 C7 175.12(15) . . . .
C6 C7 C8 O2 179.79(14) . . . .
C6 C7 C8 C3 0.9(2) . . . .
C2 C1 C9 O2 -3.9(2) . . . .
C10 C1 C9 O2 179.16(14) . . . .
C8 O2 C9 C1 0.3(2) . . . .
C9 C1 C10 C11 -0.5(2) . . . .
C2 C1 C10 C11 -177.54(13) . . . .
C9 C1 C10 C22 -126.83(16) . . . .
C2 C1 C10 C22 56.09(17) . . . .
C1 C10 C11 C12 119.24(16) . . . .
C22 C10 C11 C12 -114.99(16) . . . .
C1 C10 C11 C16 -60.8(2) . . . .
C22 C10 C11 C16 64.95(18) . . . .
C16 C11 C12 C13 1.4(2) . . . .
C10 C11 C12 C13 -178.66(14) . . . .
C11 C12 C13 C14 -0.4(2) . . . .
C12 C13 C14 C15 -0.8(2) . . . .
C13 C14 C15 C16 0.9(2) . . . .
C14 C15 C16 C11 0.2(2) . . . .
C14 C15 C16 N1 -179.50(14) . . . .
C12 C11 C16 C15 -1.3(2) . . . .
C10 C11 C16 C15 178.79(14) . . . .
C12 C11 C16 N1 178.38(14) . . . .
C10 C11 C16 N1 -1.6(2) . . . .
C17 N1 C16 C15 -49.7(2) . . . .
C17 N1 C16 C11 130.69(16) . . . .
C18 O3 C17 O4 -3.0(2) . . . .
C18 O3 C17 N1 176.42(12) . . . .
C16 N1 C17 O4 7.4(2) . . . .
C16 N1 C17 O3 -172.05(13) . . . .
C17 O3 C18 C20 -179.62(13) . . . .
C17 O3 C18 C19 -61.55(18) . . . .
C17 O3 C18 C21 62.81(19) . . . .
C23 O6 C22 O5 -5.6(2) . . . .
C23 O6 C22 C10 177.11(13) . . . .
C1 C10 C22 O5 41.5(2) . . . .
C11 C10 C22 O5 -88.14(18) . . . .
C1 C10 C22 O6 -141.29(12) . . . .
C11 C10 C22 O6 89.09(15) . . . .
