#------------------------------------------------------------------------------
#$Date: 2022-02-25 01:10:01 +0200 (Fri, 25 Feb 2022) $
#$Revision: 273146 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/64/1566413.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_1566413
loop_
_publ_author_name
'Wu, Wen-Biao'
'Mu, Bo-Shuai'
'Yu, Jin-Sheng'
'Zhou, Jian'
_publ_section_title
;
 Me2(CH2=CH)SiCN: a bifunctional ethylene equivalent for Diels-Alder
 reaction based controllable tandem synthesis
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00147K
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H17 N O'
_chemical_formula_sum            'C20 H17 N O'
_chemical_formula_weight         287.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-13 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.55952(19)
_cell_length_b                   7.19955(14)
_cell_length_c                   33.3740(6)
_cell_measurement_reflns_used    10042
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5650
_cell_measurement_theta_min      5.2840
_cell_volume                     1576.11(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  45.00   1.00    1.00    --    0.00  82.00 120.00   75
  2  ω    -88.00  -2.00   1.00    1.00    --    0.00 -57.00 120.00   86
  3  ω     -3.00  34.00   1.00    1.00    --    0.00  19.00  90.00   37
  4  ω     48.00  84.00   1.00    1.00    --    0.00  82.00 120.00   36
  5  ω    -48.00  23.00   1.00    1.00    --    0.00 -57.00   0.00   71
  6  ω     29.00  89.00   1.00    1.00    --    0.00  19.00-180.00   60
  7  ω    -19.00  20.00   1.00    1.00    --    0.00  19.00-180.00   39
  8  ω    -21.00  86.00   1.00    1.00    --    0.00  19.00 -60.00  107
  9  ω     -5.00  22.00   1.00    1.00    --    0.00  57.00 120.00   27
 10  ω     72.00 141.00   1.00    1.00    --   95.80  56.00-155.65   69
 11  ω     94.00 183.00   1.00    1.00    --   95.80  79.00-105.36   89
 12  ω     64.00  91.00   1.00    1.00    --   95.80  79.00-105.36   27
 13  ω     63.00 107.00   1.00    1.00    --   95.80  81.00  99.10   44
 14  ω    138.00 179.00   1.00    1.00    --   95.80  81.00  99.10   41
 15  ω    136.00 185.00   1.00    1.00    --   95.80  63.00 -54.19   49
 16  ω     74.00  99.00   1.00    1.00    --   95.80  54.00  -9.01   25
 17  ω    148.00 174.00   1.00    1.00    --   95.80  78.00 140.50   26
 18  ω    120.00 185.00   1.00    1.00    --   95.80  75.00-156.18   65
 19  ω     66.00  92.00   1.00    1.00    --   95.80  75.00-156.18   26
 20  ω     97.00 124.00   1.00    1.00    --   95.80  78.00 140.50   27
 21  ω     66.00  91.00   1.00    1.00    --   95.80  74.00 172.50   25
 22  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 23  ω     65.00  92.00   1.00    1.00    --   95.80  77.00 -30.00   27
 24  ω     76.00 102.00   1.00    1.00    --   95.80  45.00 -90.00   26
 25  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 26  ω      7.00 128.00   1.00    1.00    --   95.80 -82.00-150.00  121
 27  ω     99.00 182.00   1.00    1.00    --   95.80  82.00 -90.00   83
 28  ω     71.00 108.00   1.00    1.00    --   95.80  61.00   0.00   37
 29  ω     34.00  59.00   1.00    1.00    --   95.80 -82.00 120.00   25
 30  ω     71.00 103.00   1.00    1.00    --   95.80 -82.00 120.00   32
 31  ω     70.00 104.00   1.00    1.00    --   95.80  63.00 -54.19   34
 32  ω    145.00 171.00   1.00    1.00    --   95.80  77.00  55.21   26
 33  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 34  ω    117.00 142.00   1.00    1.00    --   95.80  82.00-150.00   25
 35  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  55.21   26
 36  ω     65.00  95.00   1.00    1.00    --   95.80  78.00 140.50   30
 37  ω    145.00 171.00   1.00    1.00    --   95.80  77.00  30.00   26
 38  ω     63.00  90.00   1.00    1.00    --   95.80  82.00-150.00   27
 39  ω    159.00 185.00   1.00    1.00    --   95.80  77.00 120.00   26
 40  ω     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 41  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 42  ω     59.00 127.00   1.00    1.00    --   95.80 -82.00 -60.00   68
 43  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 44  ω    111.00 184.00   1.00    1.00    --   95.80  82.00 150.00   73
 45  ω    113.00 139.00   1.00    1.00    --   95.80  56.00  24.21   26
 46  ω     75.00 100.00   1.00    1.00    --   95.80  61.00  60.00   25
 47  ω     94.00 138.00   1.00    1.00    --   95.80  77.00 120.00   44
 48  ω     64.00  89.00   1.00    1.00    --   95.80  82.00 120.00   25
 49  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 120.00   26
 50  ω     72.00 105.00   1.00    1.00    --   95.80  56.00  24.21   33
 51  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 52  ω     75.00 156.00   1.00    1.00    --   95.80  45.00-180.00   81
 53  ω     66.00 115.00   1.00    1.00    --   95.80  77.00-150.00   49
 54  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   26
 55  ω    158.00 185.00   1.00    1.00    --   95.80  56.00-155.65   27
 56  ω     76.00 171.00   1.00    1.00    --   95.80  45.00 120.00   95
 57  ω    124.00 150.00   1.00    1.00    --   95.80  54.00  -9.01   26
 58  ω    148.00 178.00   1.00    1.00    --   95.80  49.00  56.36   30
 59  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 60  ω     63.00 173.00   1.00    1.00    --   95.80  82.00  60.00  110
 61  ω     71.00 149.00   1.00    1.00    --   95.80  61.00 -30.00   78
 62  ω     14.00 113.00   1.00    1.00    --   95.80 -61.00-150.00   99
 63  ω     16.00 123.00   1.00    1.00    --   95.80 -82.00  60.00  107
 64  ω     74.00 142.00   1.00    1.00    --   95.80  49.00  56.36   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0018928000
_diffrn_orient_matrix_UB_12      0.0496753000
_diffrn_orient_matrix_UB_13      0.0448899000
_diffrn_orient_matrix_UB_21      -0.0104720000
_diffrn_orient_matrix_UB_22      0.2079197000
_diffrn_orient_matrix_UB_23      -0.0107231000
_diffrn_orient_matrix_UB_31      -0.2346435000
_diffrn_orient_matrix_UB_32      -0.0088519000
_diffrn_orient_matrix_UB_33      0.0008494000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            32998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         6.697
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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    1.211
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 985 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0392
_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)+(0.0558P)²+0.2626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1052
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2596
_reflns_number_total             2806
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc00147k2.cif
_cod_data_source_block           exp_1154
_cod_database_code               1566413
_shelx_shelxl_version_number     2016/6
_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   0.869
_shelx_estimated_absorpt_t_min   0.845
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: C01(0.5) C02(0.5) N01(0.5) N02(0.5)
3.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C12(H12a,H12b)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
;
_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 1.651
_oxdiff_exptl_absorpt_empirical_full_min 0.554
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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 -0.7470(5) -0.5160(4) -0.21941(7) 0.0456(6) Uani 1 1 d . . . . .
H1 H -0.618220 -0.513188 -0.231043 0.055 Uiso 1 1 calc R . . . .
C01 C -0.3755(9) 0.0458(7) -0.14494(16) 0.0420(12) Uani 0.5 1 d . . P . .
C02 C -0.4945(10) -0.2173(6) -0.10405(13) 0.0439(13) Uani 0.5 1 d . . P . .
C2 C -0.8786(5) -0.6609(4) -0.22777(7) 0.0524(7) Uani 1 1 d . . . . .
H2 H -0.838231 -0.754859 -0.245167 0.063 Uiso 1 1 calc R . . . .
C3 C -1.0700(5) -0.6671(4) -0.21042(8) 0.0528(7) Uani 1 1 d . . . . .
H3 H -1.157283 -0.765701 -0.215873 0.063 Uiso 1 1 calc R . . . .
C4 C -1.1311(5) -0.5264(4) -0.18498(7) 0.0476(6) Uani 1 1 d . . . . .
H4 H -1.260190 -0.530208 -0.173470 0.057 Uiso 1 1 calc R . . . .
C5 C -1.0017(4) -0.3800(4) -0.17652(7) 0.0428(6) Uani 1 1 d . . . . .
H5 H -1.044267 -0.285470 -0.159468 0.051 Uiso 1 1 calc R . . . .
C6 C -0.8075(4) -0.3736(3) -0.19348(7) 0.0403(6) Uani 1 1 d . . . . .
C7 C -0.6616(4) -0.2172(4) -0.18597(7) 0.0426(6) Uani 1 1 d . . . . .
C8 C -0.7128(4) -0.0719(3) -0.15448(7) 0.0412(6) Uani 1 1 d . . . . .
H8 H -0.851756 -0.028778 -0.159894 0.049 Uiso 1 1 calc R . . . .
C9 C -0.5732(4) 0.0979(4) -0.15648(8) 0.0445(6) Uani 1 1 d . . . . .
H9 H -0.571054 0.147391 -0.183830 0.053 Uiso 1 1 calc R . . . .
C10 C -0.6479(5) 0.2476(3) -0.12736(7) 0.0449(6) Uani 1 1 d . . . . .
H10A H -0.782223 0.289178 -0.135588 0.054 Uiso 1 1 calc R . . . .
H10B H -0.556592 0.353443 -0.128581 0.054 Uiso 1 1 calc R . . . .
C11 C -0.6585(4) 0.1770(3) -0.08402(7) 0.0431(6) Uani 1 1 d . . . . .
H11 H -0.519181 0.149061 -0.075301 0.052 Uiso 1 1 calc R . . . .
C12 C -0.7821(5) -0.0028(3) -0.08163(7) 0.0445(6) Uani 1 1 d . . . . .
H12A H -0.924280 0.025524 -0.086801 0.053 Uiso 1 1 calc R . . . .
H12B H -0.772595 -0.051874 -0.054628 0.053 Uiso 1 1 calc R . . . .
C13 C -0.7114(5) -0.1534(3) -0.11137(7) 0.0446(6) Uani 1 1 d . . . . .
C14 C -0.7447(4) 0.3224(3) -0.05585(7) 0.0412(6) Uani 1 1 d . . . . .
C15 C -0.9351(4) 0.4029(4) -0.06286(8) 0.0455(6) Uani 1 1 d . . . . .
H15 H -1.009631 0.367971 -0.085333 0.055 Uiso 1 1 calc R . . . .
C16 C -1.0144(5) 0.5341(3) -0.03677(8) 0.0485(7) Uani 1 1 d . . . . .
H16 H -1.141212 0.586724 -0.041931 0.058 Uiso 1 1 calc R . . . .
C17 C -0.9065(5) 0.5869(4) -0.00321(9) 0.0494(7) Uani 1 1 d . . . . .
H17 H -0.959430 0.675626 0.014177 0.059 Uiso 1 1 calc R . . . .
C18 C -0.7198(5) 0.5071(4) 0.00433(8) 0.0506(7) Uani 1 1 d . . . . .
H18 H -0.646958 0.541308 0.027077 0.061 Uiso 1 1 calc R . . . .
C19 C -0.6390(4) 0.3758(3) -0.02180(8) 0.0457(6) Uani 1 1 d . . . . .
H19 H -0.512477 0.323242 -0.016348 0.055 Uiso 1 1 calc R . . . .
N01 N -0.2096(8) 0.0126(8) -0.13427(17) 0.0652(14) Uani 0.5 1 d . . P . .
N02 N -0.3265(9) -0.2643(7) -0.09880(13) 0.0608(14) Uani 0.5 1 d . . P . .
O1 O -0.5032(3) -0.2053(3) -0.20497(6) 0.0553(5) Uani 1 1 d . . . . .
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 C1 C6 120.0(3) . . ?
N01 C01 C9 175.9(5) . . ?
N02 C02 C13 179.0(5) . . ?
C1 C2 C3 120.4(3) . . ?
C4 C3 C2 119.8(3) . . ?
C3 C4 C5 120.4(3) . . ?
C4 C5 C6 120.2(2) . . ?
C1 C6 C7 118.2(2) . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 122.7(2) . . ?
C6 C7 C8 119.4(2) . . ?
O1 C7 C6 120.6(2) . . ?
O1 C7 C8 119.9(3) . . ?
C7 C8 C9 112.8(2) . . ?
C7 C8 C13 112.27(19) . . ?
C9 C8 C13 109.8(2) . . ?
C01 C9 C8 109.1(3) . . ?
C01 C9 C10 108.1(3) . . ?
C8 C9 C10 110.1(2) . . ?
C9 C10 C11 112.3(2) . . ?
C12 C11 C10 110.7(2) . . ?
C14 C11 C10 111.84(19) . . ?
C14 C11 C12 110.8(2) . . ?
C11 C12 C13 113.7(2) . . ?
C02 C13 C8 105.6(3) . . ?
C02 C13 C12 113.1(3) . . ?
C12 C13 C8 109.18(19) . . ?
C15 C14 C11 121.1(2) . . ?
C19 C14 C11 120.9(2) . . ?
C19 C14 C15 118.0(2) . . ?
C16 C15 C14 120.9(3) . . ?
C17 C16 C15 120.4(3) . . ?
C18 C17 C16 119.4(3) . . ?
C17 C18 C19 120.5(3) . . ?
C14 C19 C18 120.8(3) . . ?
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
C1 C2 1.383(4) . ?
C1 C6 1.399(3) . ?
C01 C9 1.403(6) . ?
C01 N01 1.170(7) . ?
C02 C13 1.516(7) . ?
C02 N02 1.166(7) . ?
C2 C3 1.383(4) . ?
C3 C4 1.381(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.395(4) . ?
C6 C7 1.499(4) . ?
C7 C8 1.520(3) . ?
C7 O1 1.220(3) . ?
C8 C9 1.529(4) . ?
C8 C13 1.554(3) . ?
C9 C10 1.532(4) . ?
C10 C11 1.535(3) . ?
C11 C12 1.529(4) . ?
C11 C14 1.517(3) . ?
C12 C13 1.542(3) . ?
C14 C15 1.396(4) . ?
C14 C19 1.386(4) . ?
C15 C16 1.386(4) . ?
C16 C17 1.379(4) . ?
C17 C18 1.376(4) . ?
C18 C19 1.391(4) . ?
