#------------------------------------------------------------------------------
#$Date: 2021-04-05 17:29:31 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263713 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/02/1560279.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_1560279
loop_
_publ_author_name
'Brownsey, Duncan K.'
'Rowley, Ben C.'
'Gorobets, Evgueni'
'Gelfand, Benjamin S.'
'Derksen, Darren J.'
_publ_section_title
;
 Rapid synthesis of pomalidomide-conjugates for the development of protein
 degrader libraries
;
_journal_issue                   12
_journal_name_full               'Chemical Science'
_journal_page_first              4519
_journal_page_last               4525
_journal_paper_doi               10.1039/D0SC05442A
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety
'C15 H15 N3 O4, 0.377(C4 H8 O2), 0.123(C6 H14)'
_chemical_formula_sum            'C17.24 H19.73 N3 O4.75'
_chemical_formula_weight         345.09
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-24 deposited with the CCDC.	2021-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                92.523(2)
_cell_angle_beta                 106.963(2)
_cell_angle_gamma                100.062(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2814(2)
_cell_length_b                   10.1224(2)
_cell_length_c                   12.1780(3)
_cell_measurement_reflns_used    9480
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.208
_cell_measurement_theta_min      3.814
_cell_volume                     841.02(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3077
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.282
_diffrn_reflns_theta_min         3.814
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.839
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0679 before and 0.0366 after correction. The Ratio of minimum to maximum transmission is 0.9275. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             364.5
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.206
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     286
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0482
_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)+(0.0836P)²+0.4639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1247
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2989
_reflns_number_total             3077
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc05442a2.cif
_cod_data_source_block           db-3-281
_cod_depositor_comments          'Adding full bibliography for 1560279.cif.'
_cod_database_code               1560279
_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_max   0.846
_shelx_estimated_absorpt_t_min   0.763
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C6T-C2S
 1.51 with sigma of 0.02
 O1S-C2S
 1.2 with sigma of 0.02
 O2S-C2S
 1.35 with sigma of 0.02
 O2S-C3S
 1.45 with sigma of 0.02
 C4S-C3S
 1.52 with sigma of 0.02
 C1T-C2T = C2T-C3T = C3T-C4T = C4T-C5T = C5T-C6T
 1.53 with sigma of 0.02
 C1T-C5T = C3T-C6T
 -2.75 with sigma of 0.02
 C1T-C3T = C2T-C4T = C3T-C5T = C4T-C6T
 2.54 with sigma of 0.04
 O1S-C6T
 2.25 with sigma of 0.04
 C6T-O2S
 2.52 with sigma of 0.04
 O2S-O1S
 2.25 with sigma of 0.04
 C2S-C3S
 2.37 with sigma of 0.04
 O2S-C4S
 2.46 with sigma of 0.04
3. Restrained planarity
 O1S, O2S, C6T, C2S
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C2T \\sim C3T \\sim C4T \\sim C1T \\sim C5T \\sim C6T \\sim C4S \\sim O1S \\sim
C2S \\sim O2S \\sim C1SA \\sim C3S: within 2.6A with sigma of 0.03 and sigma
for terminal atoms of 0.06
5. Rigid body (RIGU) restrains
 C5T, C3T, C2T, C4T, C1T, C6T
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C3T)=Sof(H3TA)=Sof(H3TB)=Sof(C6T)=Sof(H6TA)=Sof(H6TB)=Sof(H6TC)=Sof(C1T)=
 Sof(H1TA)=Sof(H1TB)=Sof(H1TC)=Sof(C2T)=Sof(H2TA)=Sof(H2TB)=Sof(C4T)=Sof(H4TA)=
 Sof(H4TB)=Sof(C5T)=Sof(H5TA)=Sof(H5TB)=0.5*(1-FVAR(2))
 Sof(O1S)=Sof(O2S)=Sof(C2S)=Sof(C3S)=Sof(H3SA)=Sof(H3SB)=Sof(C4S)=Sof(H4SA)=
 Sof(H4SB)=Sof(H4SC)=Sof(C1SA)=Sof(H1SA)=Sof(H1SB)=Sof(H1SC)=0.5*FVAR(2)
 Sof(C15)=Sof(H15A)=Sof(H15B)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C11(H11)
7.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C3T(H3TA,H3TB), C2T(H2TA,H2TB), C3S(H3SA,
 H3SB), C4T(H4TA,H4TB), C5T(H5TA,H5TB)
7.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C4(H4), C5(H5), C6(H6)
7.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6T(H6TA,H6TB,H6TC), C1T(H1TA,H1TB,H1TC), C4S(H4SA,H4SB,
 H4SC), C1SA(H1SA,H1SB,H1SC)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.33820(19) 0.42088(12) 0.77534(10) 0.0340(3) Uani 1 1 d . . . . .
O2 O 0.05758(19) 0.15674(12) 0.43537(10) 0.0330(3) Uani 1 1 d . . . . .
O3 O 0.51537(17) 0.17136(12) 0.73062(11) 0.0304(3) Uani 1 1 d . . . . .
O4 O 0.26038(19) -0.01730(17) 0.99452(12) 0.0469(4) Uani 1 1 d . . . . .
N1 N 0.4170(2) 0.71237(15) 0.67328(16) 0.0378(4) Uani 1 1 d . . . . .
N2 N 0.18079(19) 0.26484(13) 0.61954(11) 0.0220(3) Uani 1 1 d . . . . .
N3 N 0.38090(19) 0.08175(14) 0.86191(11) 0.0245(3) Uani 1 1 d . . . . .
H3 H 0.499028 0.078265 0.906314 0.029 Uiso 1 1 calc R . . . .
C1 C 0.5130(3) 0.8477(2) 0.6611(3) 0.0563(7) Uani 1 1 d . . . . .
H1A H 0.608297 0.841261 0.619507 0.084 Uiso 1 1 calc GR . . . .
H1B H 0.580452 0.896083 0.737728 0.084 Uiso 1 1 calc GR . . . .
H1C H 0.414665 0.896490 0.617901 0.084 Uiso 1 1 calc GR . . . .
C2 C 0.3188(3) 0.7137(2) 0.7615(2) 0.0417(5) Uani 1 1 d . . . . .
H2A H 0.221(4) 0.777(3) 0.745(2) 0.063 Uiso 1 1 d R . . . .
H2B H 0.414(4) 0.749(3) 0.835(3) 0.063 Uiso 1 1 d R . . . .
H2C H 0.250(4) 0.625(3) 0.769(2) 0.063 Uiso 1 1 d R . . . .
C3 C 0.3370(2) 0.62201(16) 0.57530(16) 0.0273(4) Uani 1 1 d . . . . .
C4 C 0.3314(2) 0.66254(17) 0.46491(18) 0.0332(4) Uani 1 1 d . . . . .
H4 H 0.381859 0.754264 0.459336 0.040 Uiso 1 1 calc R . . . .
C5 C 0.2568(3) 0.57612(19) 0.36529(17) 0.0338(4) Uani 1 1 d . . . . .
H5 H 0.257697 0.609538 0.293735 0.041 Uiso 1 1 calc R . . . .
C6 C 0.1794(2) 0.43993(18) 0.36712(15) 0.0278(4) Uani 1 1 d . . . . .
H6 H 0.125778 0.379613 0.298642 0.033 Uiso 1 1 calc R . . . .
C7 C 0.1858(2) 0.39869(15) 0.47384(14) 0.0213(3) Uani 1 1 d . . . . .
C8 C 0.2630(2) 0.48365(15) 0.57662(14) 0.0215(3) Uani 1 1 d . . . . .
C9 C 0.2692(2) 0.39663(15) 0.67174(14) 0.0228(3) Uani 1 1 d . . . . .
C10 C 0.1298(2) 0.25864(15) 0.50098(13) 0.0213(3) Uani 1 1 d . . . . .
C11 C 0.1655(2) 0.14848(15) 0.68419(13) 0.0216(3) Uani 1 1 d . . . . .
H11 H 0.115987 0.066676 0.626928 0.026 Uiso 1 1 calc R . . . .
C12 C 0.3700(2) 0.13822(15) 0.75943(13) 0.0211(3) Uani 1 1 d . . . . .
C13 C 0.2275(2) 0.03024(17) 0.90243(14) 0.0268(4) Uani 1 1 d . . . . .
C14 C 0.0253(2) 0.03221(18) 0.82674(14) 0.0277(4) Uani 1 1 d . . . . .
H14A H -0.060725 0.038829 0.875629 0.033 Uiso 1 1 calc R . . . .
H14B H -0.026684 -0.053731 0.776256 0.033 Uiso 1 1 calc R . . . .
C15 C 0.0193(2) 0.14933(18) 0.75183(14) 0.0272(6) Uani 0.998(8) 1 d . . P . .
H15A H -0.114250 0.141029 0.697653 0.033 Uiso 0.998(8) 1 calc R . P . .
H15B H 0.052040 0.235696 0.801217 0.033 Uiso 0.998(8) 1 calc R . P . .
O1S O 0.0391(13) 0.6921(8) 0.9190(7) 0.108(3) Uani 0.377(4) 1 d D U P A -1
O2S O 0.0090(13) 0.5114(10) 1.0245(4) 0.0648(19) Uani 0.377(4) 1 d D U P A -1
C3T C 0.127(4) 0.564(3) 1.005(3) 0.100(7) Uani 0.123(4) 1 d D U P A -2
H3TA H 0.064198 0.608237 1.054723 0.120 Uiso 0.123(4) 1 calc R . P A -2
H3TB H 0.218167 0.634072 0.981890 0.120 Uiso 0.123(4) 1 calc R . P A -2
C6T C -0.257(5) 0.559(5) 0.989(4) 0.113(11) Uani 0.123(4) 1 d D U P A -2
H6TA H -0.342174 0.592137 0.922287 0.170 Uiso 0.123(4) 1 calc GR . P A -2
H6TB H -0.137292 0.627808 1.022773 0.170 Uiso 0.123(4) 1 calc GR . P A -2
H6TC H -0.325016 0.541000 1.046721 0.170 Uiso 0.123(4) 1 calc GR . P A -2
C1T C 0.110(5) 0.316(3) 1.058(3) 0.083(8) Uani 0.123(4) 1 d D U P A -2
H1TA H -0.027479 0.318499 1.018567 0.124 Uiso 0.123(4) 1 calc GR . P A -2
H1TB H 0.122364 0.287449 1.135184 0.124 Uiso 0.123(4) 1 calc GR . P A -2
H1TC H 0.153429 0.251200 1.013430 0.124 Uiso 0.123(4) 1 calc GR . P A -2
C2S C -0.0476(13) 0.6174(10) 0.9653(6) 0.067(2) Uani 0.377(4) 1 d D U P A -1
C2T C 0.235(6) 0.454(4) 1.067(3) 0.102(8) Uani 0.123(4) 1 d D U P A -2
H2TA H 0.343049 0.445561 1.035506 0.122 Uiso 0.123(4) 1 calc R . P A -2
H2TB H 0.294175 0.486901 1.150262 0.122 Uiso 0.123(4) 1 calc R . P A -2
C3S C 0.2035(17) 0.4944(14) 1.0142(10) 0.086(3) Uani 0.377(4) 1 d D U P A -1
H3SA H 0.310435 0.563774 1.065969 0.103 Uiso 0.377(4) 1 calc R . P A -1
H3SB H 0.206905 0.500478 0.933917 0.103 Uiso 0.377(4) 1 calc R . P A -1
C4T C -0.025(4) 0.478(4) 0.900(3) 0.107(6) Uani 0.123(4) 1 d D U P A -2
H4TA H 0.025522 0.402249 0.873600 0.128 Uiso 0.123(4) 1 calc R . P A -2
H4TB H -0.065701 0.533388 0.834950 0.128 Uiso 0.123(4) 1 calc R . P A -2
C4S C 0.221(4) 0.354(2) 1.0506(19) 0.105(8) Uani 0.377(4) 1 d D U P A -1
H4SA H 0.097371 0.290691 1.013250 0.158 Uiso 0.377(4) 1 calc GR . P A -1
H4SB H 0.250894 0.355964 1.134563 0.158 Uiso 0.377(4) 1 calc GR . P A -1
H4SC H 0.326613 0.324032 1.027272 0.158 Uiso 0.377(4) 1 calc GR . P A -1
C5T C -0.201(4) 0.427(4) 0.950(3) 0.116(8) Uani 0.123(4) 1 d D U P A -2
H5TA H -0.312900 0.370313 0.889262 0.139 Uiso 0.123(4) 1 calc R . P A -2
H5TB H -0.158905 0.373484 1.015465 0.139 Uiso 0.123(4) 1 calc R . P A -2
C1SA C -0.241(3) 0.623(2) 0.9551(15) 0.079(5) Uani 0.377(4) 1 d . U P A -1
H1SA H -0.261511 0.715129 0.944020 0.118 Uiso 0.377(4) 1 calc GR . P A -1
H1SB H -0.270313 0.595818 1.025431 0.118 Uiso 0.377(4) 1 calc GR . P A -1
H1SC H -0.327930 0.561509 0.888665 0.118 Uiso 0.377(4) 1 calc GR . P A -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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
_geom_angle_publ_flag
C2 N1 C1 111.74(16) . . ?
C3 N1 C1 118.01(19) . . ?
C3 N1 C2 120.23(15) . . ?
C9 N2 C11 123.37(13) . . ?
C10 N2 C9 111.79(13) . . ?
C10 N2 C11 124.53(13) . . ?
C13 N3 C12 127.34(13) . . ?
N1 C3 C4 121.18(16) . . ?
N1 C3 C8 123.90(16) . . ?
C8 C3 C4 114.86(16) . . ?
C5 C4 C3 123.39(15) . . ?
C4 C5 C6 121.34(16) . . ?
C7 C6 C5 115.96(16) . . ?
C6 C7 C8 124.00(15) . . ?
C6 C7 C10 126.83(15) . . ?
C8 C7 C10 108.98(13) . . ?
C3 C8 C9 132.38(15) . . ?
C7 C8 C3 120.41(15) . . ?
C7 C8 C9 106.75(13) . . ?
O1 C9 N2 121.75(15) . . ?
O1 C9 C8 131.76(15) . . ?
N2 C9 C8 106.44(13) . . ?
O2 C10 N2 125.28(14) . . ?
O2 C10 C7 128.86(14) . . ?
N2 C10 C7 105.85(13) . . ?
N2 C11 C12 108.98(12) . . ?
N2 C11 C15 112.62(13) . . ?
C15 C11 C12 113.33(12) . . ?
O3 C12 N3 120.55(14) . . ?
O3 C12 C11 123.04(14) . . ?
N3 C12 C11 116.33(13) . . ?
O4 C13 N3 119.72(15) . . ?
O4 C13 C14 123.18(15) . . ?
N3 C13 C14 117.06(14) . . ?
C13 C14 C15 112.65(14) . . ?
C11 C15 C14 109.83(13) . . ?
C2S O2S C3S 109.1(8) . . ?
C4T C3T C2T 101(2) . . ?
O1S C2S O2S 128.9(9) . . ?
O1S C2S C1SA 119.6(13) . . ?
O2S C2S C1SA 111.3(12) . . ?
C1T C2T C3T 116(2) . . ?
O2S C3S C4S 103.8(12) . . ?
C3T C4T C5T 102(2) . . ?
C6T C5T C4T 104(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
O1 C9 1.210(2) . ?
O2 C10 1.213(2) . ?
O3 C12 1.2079(19) . ?
O4 C13 1.216(2) . ?
N1 C1 1.459(3) . ?
N1 C2 1.455(3) . ?
N1 C3 1.383(2) . ?
N2 C9 1.409(2) . ?
N2 C10 1.3775(19) . ?
N2 C11 1.4514(18) . ?
N3 C12 1.3826(19) . ?
N3 C13 1.380(2) . ?
C3 C4 1.414(3) . ?
C3 C8 1.413(2) . ?
C4 C5 1.374(3) . ?
C5 C6 1.399(2) . ?
C6 C7 1.373(2) . ?
C7 C8 1.396(2) . ?
C7 C10 1.484(2) . ?
C8 C9 1.481(2) . ?
C11 C12 1.528(2) . ?
C11 C15 1.525(2) . ?
C13 C14 1.496(2) . ?
C14 C15 1.526(2) . ?
O1S C2S 1.169(11) . ?
O2S C2S 1.375(12) . ?
O2S C3S 1.495(12) . ?
C3T C2T 1.57(2) . ?
C3T C4T 1.54(2) . ?
C6T C5T 1.56(2) . ?
C1T C2T 1.51(2) . ?
C2S C1SA 1.39(2) . ?
C3S C4S 1.526(18) . ?
C4T C5T 1.59(2) . ?
