Crystal structure of 2-(bis(3,5-dimethylphenyl) ((methyldiphenylsilyl)oxy)methyl) pyrrolidine, C34H39NOSi
Govender, Kimberleigh B.; Samipillai, Marivel; Govender, Thavendran; Kruger, Hendrik G.; Naicker, Tricia; Zeitschrift für Kristallographie - New Crystal Structures 234 (2019) 413–415; doi:10.1515/ncrs-2018-0422

data_8105663
_publ_section_title
;
 Crystal structure of 2-(bis(3,5-dimethylphenyl)
 ((methyldiphenylsilyl)oxy)methyl) pyrrolidine, C34H39NOSi
;
_journal_issue                   3
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              413
_journal_page_last               415
_journal_paper_doi               10.1515/ncrs-2018-0422
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C33 H36 N O Si, C H2, H'
_chemical_formula_sum            'C34 H39 N O Si'
_chemical_formula_weight         505.75
_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
_cell_angle_alpha                69.2070(10)
_cell_angle_beta                 86.555(2)
_cell_angle_gamma                65.579(3)
_cell_formula_units_Z            2
_cell_length_a                   10.0901(2)
_cell_length_b                   11.5016(2)
_cell_length_c                   14.4098(3)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.68
_cell_measurement_theta_min      2.47
_cell_volume                     1416.10(6)
_computing_cell_refinement       'COSMO (Bruker, V1.61, 2009) [1]'
_computing_data_collection       'COSMO (Bruker, V1.61, 2009) [1]'
_computing_data_reduction        'SAINT (Bruker) [2-3]'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009) [4]'
_computing_publication_material  'ORTEP-3 [5]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)[6]'
_computing_structure_solution    'ShelXS-2013 (Sheldrick, 2008) [7]'
_diffrn_ambient_temperature      100.03
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39154
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.809
_diffrn_reflns_theta_min         2.087
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_recrystallization_method
'The material was recrystallised from acetonitrile by slow evaporation'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         7216
_refine_ls_number_restraints     153
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0463
_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/[\s^2^(Fo^2^)+(0.0456P)^2^+1.0464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1200
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6613
_reflns_number_total             7216
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2018-0422_suppl.cif
_cod_data_source_block           18zs_ggkm_gkb2_0m
_cod_database_code               8105663
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.961
_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
 H28-H32D
 2.11 with sigma of 0.001
 H13C-H1A
 2.2 with sigma of 0.001
 N1A-H1A = N1B-H1B
 0.89 with sigma of 0.001
 C34A-C33A \\sim C33A-C32A \\sim C32A-C31
 with sigma of 0.02
 N1A-C34A \\sim N1A-C31
 with sigma of 0.02
 N1A-C33A \\sim N1A-C32A
 with sigma of 0.04
 C33A-C31 \\sim C34A-C32A
 with sigma of 0.04
 N1A-C34A \\sim N1B-C33B
 with sigma of 0.02
 N1A-C31 \\sim N1B-C31
 with sigma of 0.02
 C34A-C33A \\sim C33B-C34B
 with sigma of 0.02
 C33A-C32A \\sim C34B-C32B
 with sigma of 0.02
 C32A-C31 \\sim C32B-C31
 with sigma of 0.02
 N1A-C33A \\sim N1B-C34B
 with sigma of 0.04
 C34A-C32A \\sim C33B-C32B
 with sigma of 0.04
 C34A-C31 \\sim C33B-C31
 with sigma of 0.04
 C33A-C31 \\sim C34B-C31
 with sigma of 0.04
3. Rigid bond restraints
 C31, C32B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
C31 \\sim N1A \\sim C32A \\sim C33A \\sim C34A: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08
Uanis(C34A) \\sim Ueq, Uanis(C33A) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C34A) \\sim Ueq, Uanis(C33A) \\sim Ueq, Uanis(C32A) \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.002
Uanis(N1B) \\sim Ueq, Uanis(C33B) \\sim Ueq, Uanis(C34B) \\sim Ueq, Uanis(C32B)
\\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Rigid body (RIGU) restrains
 C31, N1A, C32A, C33A, C34A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1A, C32A, C33A, C34A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1B, C32B, C33B, C34B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(H31A)=Sof(N1B)=Sof(C32B)=Sof(H32C)=Sof(H32D)=Sof(C33B)=Sof(H33C)=
 Sof(H33D)=1-FVAR(1)
 Sof(H31)=Sof(N1A)=Sof(C32A)=Sof(H32A)=Sof(H32B)=Sof(C33A)=Sof(H33A)=Sof(H33B)=
 FVAR(1)
 Fixed Sof: H1A(0.5) C34A(0.3) H34A(0.3) H34B(0.3) H1B(0.5) C34B(0.7)
 H34C(0.7) H34D(0.7)
7.a Ternary CH refined with riding coordinates:
 C31(H31), C31(H31A)
7.b Secondary CH2 refined with riding coordinates:
 C32A(H32A,H32B), C33A(H33A,H33B), C34A(H34A,H34B), C32B(H32C,H32D), C33B(H33C,
 H33D), C34B(H34C,H34D)
7.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C16(H16), C18(H18), C20(H20), C24(H24), C26(H26), C28(H28)
7.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C29(H29A,H29B,
 H29C), C30(H30A,H30B,H30C)
;