#------------------------------------------------------------------------------
#$Date: 2021-06-10 04:30:42 +0300 (Thu, 10 Jun 2021) $
#$Revision: 266340 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/32/1563274.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_1563274
loop_
_publ_author_name
'Yan, Zhi-Bo'
'Peng, Meng'
'Chen, Qi-Long'
'Lu, Ka'
'Tu, Yong Qiang'
'Dai, Kun Long'
'Zhang, Fu-Min'
'Zhang, Xiao-Ming'
_publ_section_title
;
 An Effective and Versatile Strategy for the Synthesis of Structurally
 Diverse Heteroarylsilanes via Ir(III)-Catalyzed C−H Silylation
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02344F
_journal_year                    2021
_chemical_formula_moiety         'C15 H23 N O Si'
_chemical_formula_sum            'C15 H23 N O Si'
_chemical_formula_weight         261.43
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-01-22
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.11.30 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5622)
;
_audit_update_record
;
2021-03-05 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   17.07243(19)
_cell_length_b                   17.07243(19)
_cell_length_c                   21.9046(4)
_cell_measurement_reflns_used    6303
_cell_measurement_temperature    149.96(10)
_cell_measurement_theta_max      76.0020
_cell_measurement_theta_min      3.2820
_cell_volume                     6384.49(15)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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      149.96(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00   4.00   1.00    0.15    --  -46.32  19.00 -90.00   29
  2  ω    -69.00 -44.00   1.00    0.70    -- -102.00  61.00  90.00   25
  3  ω    -69.00 -44.00   1.00    0.70    -- -102.00  61.00 120.00   25
  4  ω   -105.00 -79.00   1.00    0.70    -- -102.00   2.00  52.00   26
  5  ω   -174.00-149.00   1.00    0.70    -- -102.00   2.00  52.00   25
  6  ω    -96.00 -67.00   1.00    0.15    --  -46.32-137.00 -13.00   29
  7  ω     27.00  89.00   1.00    0.15    --   46.32-132.00 163.00   62
  8  ω    151.00 176.00   1.00    0.70    --  103.99  45.00 -30.00   25
  9  ω     92.00 175.00   1.00    0.70    --  103.99  45.00  60.00   83
 10  ω     92.00 143.00   1.00    0.70    --  103.99  45.00 -30.00   51
 11  ω     42.00 103.00   1.00    0.70    --  103.99-132.00 163.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0022570000
_diffrn_orient_matrix_UB_12      0.0280819000
_diffrn_orient_matrix_UB_13      -0.0668239000
_diffrn_orient_matrix_UB_21      -0.0016613000
_diffrn_orient_matrix_UB_22      -0.0856912000
_diffrn_orient_matrix_UB_23      -0.0219361000
_diffrn_orient_matrix_UB_31      -0.0902076000
_diffrn_orient_matrix_UB_32      0.0023644000
_diffrn_orient_matrix_UB_33      -0.0012432000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9382
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.231
_diffrn_reflns_theta_min         3.282
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.088
_exptl_crystal_description       block
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0480
_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)+(0.0762P)²+2.7684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1356
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2853
_reflns_number_total             3209
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc02344f2.cif
_cod_data_source_block           yanzhb_0120
_cod_original_cell_volume        6384.49(18)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               1563274
_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   0.920
_shelx_estimated_absorpt_t_min   0.869
_diffrn_oxdiff_digest_frames
;
0135eaa85b0fc23eb8080f5303423b02ff00029e143
;
_diffrn_oxdiff_digest_hkl
;
01322a70647203d8bf3e07b78c3fff9dbee268
;
_reflns_odcompleteness_completeness 99.56
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H11A,H11B), C12(H14A,H14B), C14(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H2), C2(H4), C4(H7), C5(H6), C7(H10)
2.c Idealised Me refined as rotating group:
 C9(H12A,H12B,H12C), C11(H16A,H16B,H16C), C13(H15A,H15B,H15C), C15(H17A,H17B,
 H17C)
;
_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 2.247
_oxdiff_exptl_absorpt_empirical_full_min 0.383
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+3/4, x+1/4, z+1/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z+1/4'
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
Si1 Si 0.80438(3) 0.67998(3) 0.11202(2) 0.04248(17) Uani 1 1 d . . . . .
O1 O 0.88929(6) 0.62922(6) -0.23205(5) 0.0400(3) Uani 1 1 d . . . . .
N1 N 0.83387(8) 0.69134(7) -0.01703(6) 0.0375(3) Uani 1 1 d . . . . .
H2 H 0.832154 0.741664 -0.015861 0.045 Uiso 1 1 calc R . . . .
C1 C 0.84814(8) 0.64774(8) -0.06847(7) 0.0344(3) Uani 1 1 d . . . . .
C2 C 0.86128(9) 0.67273(9) -0.12840(7) 0.0355(3) Uani 1 1 d . . . . .
H4 H 0.861172 0.725513 -0.138893 0.043 Uiso 1 1 calc R . . . .
C3 C 0.87443(8) 0.61471(9) -0.17118(7) 0.0353(3) Uani 1 1 d . . . . .
C4 C 0.87454(9) 0.53478(9) -0.15529(7) 0.0390(3) Uani 1 1 d . . . . .
H7 H 0.884319 0.497319 -0.185154 0.047 Uiso 1 1 calc R . . . .
C5 C 0.86043(9) 0.51140(9) -0.09639(8) 0.0412(4) Uani 1 1 d . . . . .
H6 H 0.859912 0.458436 -0.086460 0.049 Uiso 1 1 calc R . . . .
C6 C 0.84675(9) 0.56831(9) -0.05113(7) 0.0373(3) Uani 1 1 d . . . . .
C7 C 0.83001(10) 0.56666(9) 0.01274(7) 0.0429(4) Uani 1 1 d . . . . .
H10 H 0.824997 0.521829 0.036532 0.051 Uiso 1 1 calc R . . . .
C8 C 0.82256(10) 0.64224(9) 0.03310(7) 0.0396(3) Uani 1 1 d . . . . .
C9 C 0.88615(13) 0.70863(11) -0.25151(8) 0.0547(5) Uani 1 1 d . . . . .
H12A H 0.897238 0.711408 -0.294423 0.082 Uiso 1 1 calc GR . . . .
H12B H 0.924283 0.738710 -0.229424 0.082 Uiso 1 1 calc GR . . . .
H12C H 0.834824 0.729361 -0.243828 0.082 Uiso 1 1 calc GR . . . .
C10 C 0.74816(14) 0.77383(11) 0.10605(8) 0.0568(5) Uani 1 1 d . . . . .
H11A H 0.745858 0.798061 0.146067 0.068 Uiso 1 1 calc R . . . .
H11B H 0.776151 0.809205 0.079128 0.068 Uiso 1 1 calc R . . . .
C11 C 0.66472(17) 0.76335(16) 0.08205(13) 0.0817(7) Uani 1 1 d . . . . .
H16A H 0.666281 0.737764 0.043046 0.123 Uiso 1 1 calc GR . . . .
H16B H 0.640285 0.813702 0.077810 0.123 Uiso 1 1 calc GR . . . .
H16C H 0.635192 0.732003 0.110237 0.123 Uiso 1 1 calc GR . . . .
C12 C 0.74809(13) 0.60407(11) 0.15450(9) 0.0559(5) Uani 1 1 d . . . . .
H14A H 0.698067 0.596252 0.134410 0.067 Uiso 1 1 calc R . . . .
H14B H 0.776555 0.554948 0.152751 0.067 Uiso 1 1 calc R . . . .
C13 C 0.73339(17) 0.62524(16) 0.22169(10) 0.0766(7) Uani 1 1 d . . . . .
H15A H 0.703870 0.673021 0.223861 0.115 Uiso 1 1 calc GR . . . .
H15B H 0.782632 0.632074 0.242170 0.115 Uiso 1 1 calc GR . . . .
H15C H 0.704488 0.583875 0.241013 0.115 Uiso 1 1 calc GR . . . .
C14 C 0.90084(13) 0.69663(13) 0.15015(9) 0.0614(5) Uani 1 1 d . . . . .
H13A H 0.931932 0.731463 0.124925 0.074 Uiso 1 1 calc R . . . .
H13B H 0.891831 0.722738 0.188851 0.074 Uiso 1 1 calc R . . . .
C15 C 0.94757(15) 0.62207(16) 0.16178(11) 0.0740(6) Uani 1 1 d . . . . .
H17A H 0.953406 0.593655 0.124239 0.111 Uiso 1 1 calc GR . . . .
H17B H 0.920417 0.590109 0.190972 0.111 Uiso 1 1 calc GR . . . .
H17C H 0.998341 0.635487 0.177459 0.111 Uiso 1 1 calc GR . . . .
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'
Si Si 0.2541 0.3302 '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
C8 Si1 C10 108.38(8) . . ?
C12 Si1 C8 107.91(8) . . ?
C12 Si1 C10 111.46(10) . . ?
C12 Si1 C14 109.71(10) . . ?
C14 Si1 C8 108.62(9) . . ?
C14 Si1 C10 110.67(10) . . ?
C3 O1 C9 117.00(12) . . ?
C1 N1 C8 110.18(12) . . ?
N1 C1 C2 129.33(13) . . ?
N1 C1 C6 107.33(13) . . ?
C2 C1 C6 123.34(13) . . ?
C3 C2 C1 116.36(14) . . ?
O1 C3 C2 123.82(14) . . ?
O1 C3 C4 114.37(13) . . ?
C2 C3 C4 121.81(14) . . ?
C5 C4 C3 120.95(14) . . ?
C4 C5 C6 119.38(14) . . ?
C1 C6 C7 106.65(13) . . ?
C5 C6 C1 118.16(14) . . ?
C5 C6 C7 135.19(15) . . ?
C8 C7 C6 108.58(13) . . ?
N1 C8 Si1 122.91(11) . . ?
C7 C8 Si1 129.80(12) . . ?
C7 C8 N1 107.26(13) . . ?
C11 C10 Si1 113.67(15) . . ?
C13 C12 Si1 113.53(15) . . ?
C15 C14 Si1 114.16(16) . . ?
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
Si1 C8 1.8708(16) . ?
Si1 C10 1.872(2) . ?
Si1 C12 1.8626(18) . ?
Si1 C14 1.868(2) . ?
O1 C3 1.3796(18) . ?
O1 C9 1.422(2) . ?
N1 C1 1.3723(19) . ?
N1 C8 1.3948(19) . ?
C1 C2 1.398(2) . ?
C1 C6 1.408(2) . ?
C2 C3 1.382(2) . ?
C3 C4 1.408(2) . ?
C4 C5 1.372(2) . ?
C5 C6 1.408(2) . ?
C6 C7 1.428(2) . ?
C7 C8 1.371(2) . ?
C10 C11 1.529(4) . ?
C12 C13 1.536(3) . ?
C14 C15 1.524(3) . ?
