#------------------------------------------------------------------------------
#$Date: 2023-08-24 00:56:17 +0300 (Thu, 24 Aug 2023) $
#$Revision: 285849 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/20/7132045.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_7132045
loop_
_publ_author_name
'Matsuo, Bianca'
'Kim, Saegun'
'Shreiber, Scott T.'
'Levitre, Guillaume'
'Li, Longbo'
'Crane, Erika A.'
'McClain, Edward J.'
'Voight, Eric A.'
'Molander, Gary A.'
_publ_section_title
;
 Diversifying chemical space of DNA-encoded libraries: synthesis of
 2-oxa-1-azaspiro(bicyclo[3.2.0])heptanes on-DNA via visible
 light-mediated energy transfer catalysis.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc03421f
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H21 N O3'
_chemical_formula_sum            'C17 H21 N O3'
_chemical_formula_weight         287.35
_chemical_name_common            'chemical 1''
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-05
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-05-08 deposited with the CCDC.	2023-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.78560(10)
_cell_length_b                   32.0930(3)
_cell_length_c                   5.26760(10)
_cell_measurement_reflns_used    15994
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.2610
_cell_measurement_theta_min      2.7300
_cell_volume                     1485.23(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'HPC area detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix-6000HE
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -34.00   0.50    1.00    --  -47.31 -50.00  20.00  170
  2  ω    -60.00  25.00   0.50    1.00    --  -47.31  50.00 167.00  170
  3  ω     34.00 120.00   0.50    1.00    --   47.31  50.00 167.00  172
  4  ω    -24.00  54.00   0.50    1.00    --   47.31 -50.00  20.00  156
  5  ω   -161.00 -76.00   0.50    1.00    --  -90.00 -50.00  20.00  170
  6  ω    -60.00 -17.00   0.50    1.00    --  -90.00  50.00 167.00   86
  7  ω    100.00 178.00   0.50    1.00    --  113.25  50.00 167.00  156
  8  ω     25.00 120.00   0.50    1.00    --   47.31  77.00 -90.00  190
  9  ω     35.00 121.00   0.50    1.00    --   47.31  37.00 -90.00  172
 10  ω    -27.00  23.00   0.50    1.00    --   47.31 -19.00-150.00  100
 11  ω   -162.00 -73.00   0.50    1.00    --  -90.00 -63.00 -92.11  178
 12  ω   -162.00 -68.00   0.50    1.00    --  -90.00 -75.00-117.94  188
 13  ω    -54.00 -18.00   0.50    1.00    --  -90.00  45.00   0.00   72
 14  ω    -54.00 -18.00   0.50    1.00    --  -90.00  45.00 -30.00   72
 15  ω   -141.00 -76.00   0.50    1.00    --  -90.00 -52.00 -69.21  130
 16  ω    -99.00 -69.00   0.50    1.00    --  -90.00 -77.00 -90.00   60
 17  ω    -93.00 -67.00   0.50    1.00    --  -90.00 -77.00 -60.00   52
 18  ω    -98.00 -72.00   0.50    1.00    --  -90.00 -64.00 -39.17   52
 19  ω    136.00 178.00   0.50    1.00    --  113.25  77.00 -90.00   84
 20  ω    119.00 177.00   0.50    1.00    --  113.25  30.00  60.00  116
 21  ω     42.00  68.00   0.50    1.00    --  113.25 -61.00-180.00   52
 22  ω     42.00  67.00   0.50    1.00    --  113.25 -61.00 -60.00   50
 23  ω     62.00  98.00   0.50    1.00    --  113.25 -77.00 -30.00   72
 24  ω     64.00 101.00   0.50    1.00    --  113.25 -77.00 120.00   74
 25  ω     42.00  68.00   0.50    1.00    --  113.25 -61.00 150.00   52
 26  ω    151.00 177.00   0.50    1.00    --  113.25  77.00-150.00   52
 27  ω     91.00 129.00   0.50    1.00    --  113.25  77.00-150.00   76
 28  ω     42.00  67.00   0.50    1.00    --  113.25 -61.00 -30.00   50
 29  ω     42.00  67.00   0.50    1.00    --  113.25 -61.00  90.00   50
 30  ω    103.00 129.00   0.50    1.00    --  113.25  47.00-104.00   52
 31  ω     45.00  98.00   0.50    1.00    --  113.25 -77.00  90.00  106
 32  ω    101.00 127.00   0.50    1.00    --  113.25  45.00 -90.00   52
 33  ω    130.00 155.00   0.50    1.00    --  113.25  45.00 -90.00   50
 34  ω     94.00 119.00   0.50    1.00    --  113.25  77.00 -90.00   50
 35  ω    151.00 176.00   0.50    1.00    --  113.25  61.00 -30.00   50
 36  ω     98.00 151.00   0.50    1.00    --  113.25  61.00 -60.00  106
 37  ω    110.00 136.00   0.50    1.00    --  113.25  61.00 -30.00   52
 38  ω     63.00  89.00   0.50    1.00    --  113.25 -77.00 -90.00   52
 39  ω     42.00  67.00   0.50    1.00    --  113.25 -61.00-120.00   50
 40  ω    122.00 175.00   0.50    1.00    --  113.25  77.00-180.00  106
 41  ω    103.00 121.00   0.50    1.00    --  113.25  61.00 -90.00   36
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0284994000
_diffrn_orient_matrix_UB_12      0.0473129000
_diffrn_orient_matrix_UB_13      -0.0132923000
_diffrn_orient_matrix_UB_21      0.1383492000
_diffrn_orient_matrix_UB_22      -0.0048976000
_diffrn_orient_matrix_UB_23      0.1772612000
_diffrn_orient_matrix_UB_31      0.1039257000
_diffrn_orient_matrix_UB_32      -0.0064465000
_diffrn_orient_matrix_UB_33      -0.2322263000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            19650
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.438
_diffrn_reflns_theta_min         2.754
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colorless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1269 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3023
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0425P)²+0.3159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0771
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2942
_reflns_number_total             3023
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc03421f2.cif
_cod_data_source_block           9262
_cod_database_code               7132045
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.732
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.490
_oxdiff_exptl_absorpt_empirical_full_min 0.366
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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 0.63131(14) 0.60099(4) 0.4746(2) 0.0192(3) Uani 1 1 d . . . . .
O2 O 0.55622(17) 0.73682(4) 0.6668(3) 0.0349(4) Uani 1 1 d . . . . .
O3 O 0.43846(15) 0.69200(4) 0.4085(3) 0.0256(3) Uani 1 1 d . . . . .
N1 N 0.70560(16) 0.63996(4) 0.5240(3) 0.0178(3) Uani 1 1 d . . . . .
C1 C 0.6086(2) 0.66358(5) 0.7113(3) 0.0187(4) Uani 1 1 d . . . . .
C2 C 0.4925(2) 0.63175(5) 0.8121(4) 0.0216(4) Uani 1 1 d . . . . .
H2A H 0.493792 0.630918 0.999989 0.026 Uiso 1 1 calc R U . . .
H2B H 0.388381 0.638775 0.754421 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5443(2) 0.58982(5) 0.7005(3) 0.0191(4) Uani 1 1 d . . . . .
H3 H 0.611826 0.575151 0.824454 0.023 Uiso 1 1 calc R U . . .
C4 C 0.4150(2) 0.56156(5) 0.6240(3) 0.0192(4) Uani 1 1 d . . . . .
C5 C 0.3208(2) 0.57109(6) 0.4191(3) 0.0232(4) Uani 1 1 d . . . . .
H5 H 0.341408 0.594929 0.317838 0.028 Uiso 1 1 calc R U . . .
C6 C 0.1970(2) 0.54590(6) 0.3623(4) 0.0258(4) Uani 1 1 d . . . . .
H6 H 0.133005 0.552614 0.222723 0.031 Uiso 1 1 calc R U . . .
C7 C 0.1663(2) 0.51094(6) 0.5087(4) 0.0247(4) Uani 1 1 d . . . . .
H7 H 0.081166 0.493830 0.469792 0.030 Uiso 1 1 calc R U . . .
C8 C 0.2598(2) 0.50102(5) 0.7114(4) 0.0245(4) Uani 1 1 d . . . . .
H8 H 0.238905 0.477130 0.811984 0.029 Uiso 1 1 calc R U . . .
C9 C 0.3847(2) 0.52619(6) 0.7676(4) 0.0220(4) Uani 1 1 d . . . . .
H9 H 0.449581 0.519102 0.905165 0.026 Uiso 1 1 calc R U . . .
C10 C 0.7505(2) 0.67190(6) 0.8747(4) 0.0203(4) Uani 1 1 d . . . . .
H10A H 0.793588 0.700195 0.854117 0.024 Uiso 1 1 calc R U . . .
H10B H 0.737670 0.664715 1.056218 0.024 Uiso 1 1 calc R U . . .
C11 C 0.83191(19) 0.63820(5) 0.7178(3) 0.0186(4) Uani 1 1 d . . . . .
C12 C 0.8820(2) 0.59781(5) 0.8542(4) 0.0208(4) Uani 1 1 d . . . . .
H12A H 0.838135 0.594361 1.025980 0.025 Uiso 1 1 calc R U . . .
H12B H 0.868987 0.572241 0.751327 0.025 Uiso 1 1 calc R U . . .
C13 C 1.0458(2) 0.61539(6) 0.8528(4) 0.0236(4) Uani 1 1 d . . . . .
H13A H 1.124318 0.594710 0.804944 0.028 Uiso 1 1 calc R U . . .
H13B H 1.074119 0.630192 1.010759 0.028 Uiso 1 1 calc R U . . .
C14 C 0.9980(2) 0.64465(6) 0.6332(4) 0.0226(4) Uani 1 1 d . . . . .
H14A H 1.034825 0.673639 0.651758 0.027 Uiso 1 1 calc R U . . .
H14B H 1.020838 0.633546 0.461991 0.027 Uiso 1 1 calc R U . . .
C15 C 0.5335(2) 0.70183(5) 0.5957(3) 0.0202(4) Uani 1 1 d . . . . .
C16 C 0.3608(2) 0.72704(6) 0.2881(4) 0.0288(4) Uani 1 1 d . . . . .
H16A H 0.433513 0.743215 0.183716 0.035 Uiso 1 1 calc R U . . .
H16B H 0.317641 0.745747 0.419053 0.035 Uiso 1 1 calc R U . . .
C17 C 0.2366(2) 0.71001(6) 0.1248(4) 0.0255(4) Uani 1 1 d . . . . .
H17A H 0.279682 0.690281 0.002295 0.038 Uiso 1 1 calc R U . . .
H17B H 0.186940 0.732891 0.033577 0.038 Uiso 1 1 calc R U . . .
H17C H 0.161593 0.695669 0.231271 0.038 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 0.0181 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
N1 O1 C3 107.74(12) . . ?
C15 O3 C16 115.62(14) . . ?
O1 N1 C1 107.44(12) . . ?
O1 N1 C11 115.13(12) . . ?
C1 N1 C11 89.54(12) . . ?
N1 C1 C2 105.47(13) . . ?
N1 C1 C10 89.74(13) . . ?
N1 C1 C15 112.90(14) . . ?
C10 C1 C2 117.35(15) . . ?
C15 C1 C2 112.73(15) . . ?
C15 C1 C10 115.82(15) . . ?
C3 C2 C1 104.64(14) . . ?
O1 C3 C2 104.61(13) . . ?
O1 C3 C4 108.95(15) . . ?
C4 C3 C2 113.91(15) . . ?
C5 C4 C3 121.47(16) . . ?
C9 C4 C3 119.38(16) . . ?
C9 C4 C5 119.09(17) . . ?
C6 C5 C4 120.30(17) . . ?
C5 C6 C7 120.23(18) . . ?
C8 C7 C6 119.94(17) . . ?
C7 C8 C9 119.84(17) . . ?
C4 C9 C8 120.59(18) . . ?
C11 C10 C1 87.38(13) . . ?
N1 C11 C10 89.71(13) . . ?
N1 C11 C12 123.73(14) . . ?
N1 C11 C14 119.74(15) . . ?
C10 C11 C12 118.19(15) . . ?
C10 C11 C14 120.14(15) . . ?
C14 C11 C12 88.70(13) . . ?
C13 C12 C11 87.53(13) . . ?
C12 C13 C14 88.42(14) . . ?
C11 C14 C13 87.66(13) . . ?
O2 C15 O3 123.91(17) . . ?
O2 C15 C1 123.89(17) . . ?
O3 C15 C1 112.19(15) . . ?
O3 C16 C17 108.04(15) . . ?
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 N1 1.4345(18) . ?
O1 C3 1.459(2) . ?
O2 C15 1.200(2) . ?
O3 C15 1.330(2) . ?
O3 C16 1.460(2) . ?
N1 C1 1.508(2) . ?
N1 C11 1.509(2) . ?
C1 C2 1.538(2) . ?
C1 C10 1.538(2) . ?
C1 C15 1.521(2) . ?
C2 C3 1.537(2) . ?
C3 C4 1.508(2) . ?
C4 C5 1.395(3) . ?
C4 C9 1.390(2) . ?
C5 C6 1.388(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.384(3) . ?
C8 C9 1.394(3) . ?
C10 C11 1.538(2) . ?
C11 C12 1.546(2) . ?
C11 C14 1.540(2) . ?
C12 C13 1.545(2) . ?
C13 C14 1.548(3) . ?
C16 C17 1.493(3) . ?
