#------------------------------------------------------------------------------
#$Date: 2016-04-05 20:59:19 +0300 (Tue, 05 Apr 2016) $
#$Revision: 181737 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/73/7037377.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_7037377
loop_
_publ_author_name
'Younis, Fadi M.'
'Krieck, Sven'
'Görls, Helmar'
'Westerhausen, Matthias'
_publ_section_title
;
 Hydroamination of diphenylbutadiyne with secondary N-methyl-anilines
 using the dipotassium tetrakis(2,6-diisopropylanilino)calciate
 precatalyst.
;
_journal_issue                   14
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6241
_journal_page_last               6250
_journal_paper_doi               10.1039/c5dt03818a
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C30 H27 F N2'
_chemical_formula_sum            'C30 H27 F N2'
_chemical_formula_weight         434.54
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-09-24 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.576(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.7393(4)
_cell_length_b                   8.3583(3)
_cell_length_c                   11.9106(4)
_cell_measurement_temperature    133(2)
_cell_volume                     1148.82(7)
_computing_cell_refinement       DENZO
_computing_data_collection       COLLECT
_computing_data_reduction        DENZO
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7762
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.042
_exptl_crystal_size_mid          0.038
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0671
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0716P)²+1.1608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1778
_refine_ls_wR_factor_ref         0.1824
_reflns_number_gt                2346
_reflns_number_total             2618
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5dt03818a2.cif
_cod_data_source_block           FO5630
_cod_depositor_comments
'Adding full bibliography for 7037372--7037377.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7037377
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.78383(14) 0.4321(2) 0.45055(14) 0.0228(4) Uani 1 1 d . . .
C1 C 0.88809(16) 0.3499(2) 0.44009(16) 0.0212(4) Uani 1 1 d . . .
C2 C 0.99189(17) 0.4192(2) 0.47857(17) 0.0232(4) Uani 1 1 d . . .
H2 H 1.062(2) 0.355(3) 0.482(2) 0.021(6) Uiso 1 1 d . . .
C3 C 0.7554(2) 0.4508(3) 0.56385(19) 0.0335(5) Uani 1 1 d . . .
H3C H 0.821(2) 0.411(3) 0.623(2) 0.038(7) Uiso 1 1 d . . .
H3B H 0.685(3) 0.399(4) 0.569(3) 0.061(10) Uiso 1 1 d . . .
H3A H 0.740(3) 0.564(4) 0.584(3) 0.049(8) Uiso 1 1 d . . .
C4 C 0.70634(17) 0.4847(2) 0.35495(16) 0.0214(4) Uani 1 1 d . A .
C5 C 0.73135(18) 0.4673(3) 0.24449(18) 0.0247(4) Uani 1 1 d . . .
H5 H 0.803(2) 0.415(4) 0.235(2) 0.042(8) Uiso 1 1 d . . .
C6 C 0.65842(19) 0.5303(3) 0.15012(19) 0.0301(5) Uani 1 1 d . A .
H6 H 0.677(3) 0.522(4) 0.076(3) 0.044(8) Uiso 1 1 d . . .
F1 F 0.4964(2) 0.6815(4) 0.0691(2) 0.0406(7) Uani 0.50 1 d P A 1
C7 C 0.55907(19) 0.6103(3) 0.1634(2) 0.0326(5) Uani 1 1 d . . .
H7A H 0.5102 0.6553 0.0987 0.039 Uiso 0.50 1 calc PR A 2
C8 C 0.53009(18) 0.6254(3) 0.2703(2) 0.0309(5) Uani 1 1 d . A .
H8 H 0.459(2) 0.683(4) 0.277(2) 0.042(8) Uiso 1 1 d . . .
C9 C 0.60222(17) 0.5628(3) 0.36550(19) 0.0257(5) Uani 1 1 d . . .
H9 H 0.583(2) 0.575(3) 0.441(2) 0.034(7) Uiso 1 1 d . . .
C10 C 0.87718(17) 0.1837(2) 0.39635(16) 0.0215(4) Uani 1 1 d . . .
C11 C 0.96991(18) 0.1004(3) 0.36519(17) 0.0243(4) Uani 1 1 d . . .
H11 H 1.049(2) 0.155(3) 0.368(2) 0.028(6) Uiso 1 1 d . . .
C12 C 0.9578(2) -0.0594(3) 0.33214(18) 0.0276(5) Uani 1 1 d . . .
H12 H 1.028(2) -0.112(3) 0.316(2) 0.035(7) Uiso 1 1 d . . .
C13 C 0.8532(2) -0.1376(3) 0.32685(18) 0.0279(5) Uani 1 1 d . . .
H13 H 0.846(2) -0.248(4) 0.306(2) 0.037(7) Uiso 1 1 d . . .
C14 C 0.7595(2) -0.0560(3) 0.35415(19) 0.0289(5) Uani 1 1 d . . .
H14 H 0.682(3) -0.104(4) 0.347(2) 0.041(7) Uiso 1 1 d . . .
C15 C 0.77114(18) 0.1033(3) 0.38847(17) 0.0250(4) Uani 1 1 d . . .
H15 H 0.706(2) 0.156(3) 0.408(2) 0.036(7) Uiso 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C4 N1 C1 121.48(16) . .
C4 N1 C3 119.83(17) . .
C1 N1 C3 118.56(17) . .
C2 C1 N1 119.84(18) . .
C2 C1 C10 122.43(18) . .
N1 C1 C10 117.49(17) . .
C1 C2 C2 125.0(2) . 3_766
C1 C2 H2 119.0(14) . .
C2 C2 H2 115.9(14) 3_766 .
N1 C3 H3C 109.9(16) . .
N1 C3 H3B 111(2) . .
H3C C3 H3B 112(3) . .
N1 C3 H3A 114.1(18) . .
H3C C3 H3A 107(2) . .
H3B C3 H3A 102(3) . .
N1 C4 C5 121.01(18) . .
N1 C4 C9 121.32(18) . .
C5 C4 C9 117.62(19) . .
C6 C5 C4 121.02(19) . .
C6 C5 H5 119.5(17) . .
C4 C5 H5 119.4(17) . .
C7 C6 C5 120.1(2) . .
C7 C6 H6 119.2(18) . .
C5 C6 H6 120.7(18) . .
F1 C7 C6 117.3(2) . .
F1 C7 C8 122.1(2) . .
C6 C7 C8 120.4(2) . .
F1 C7 H7A 4.5 . .
C6 C7 H7A 119.8 . .
C8 C7 H7A 119.8 . .
C7 C8 C9 120.1(2) . .
C7 C8 H8 118.8(17) . .
C9 C8 H8 121.1(17) . .
C8 C9 C4 120.7(2) . .
C8 C9 H9 120.5(16) . .
C4 C9 H9 118.7(16) . .
C11 C10 C15 117.93(18) . .
C11 C10 C1 122.63(18) . .
C15 C10 C1 119.42(18) . .
C12 C11 C10 120.59(19) . .
C12 C11 H11 118.5(14) . .
C10 C11 H11 120.9(14) . .
C13 C12 C11 120.6(2) . .
C13 C12 H12 123.1(16) . .
C11 C12 H12 116.2(16) . .
C14 C13 C12 119.7(2) . .
C14 C13 H13 120.2(17) . .
C12 C13 H13 120.1(17) . .
C13 C14 C15 120.1(2) . .
C13 C14 H14 122.9(17) . .
C15 C14 H14 117.0(17) . .
C14 C15 C10 121.1(2) . .
C14 C15 H15 118.4(17) . .
C10 C15 H15 120.5(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C4 1.392(3) .
N1 C1 1.429(2) .
N1 C3 1.457(3) .
C1 C2 1.351(3) .
C1 C10 1.481(3) .
C2 C2 1.443(4) 3_766
C2 H2 0.98(2) .
C3 H3C 1.00(3) .
C3 H3B 0.95(4) .
C3 H3A 1.00(3) .
C4 C5 1.407(3) .
C4 C9 1.412(3) .
C5 C6 1.386(3) .
C5 H5 0.98(3) .
C6 C7 1.378(3) .
C6 H6 0.95(3) .
F1 C7 1.362(3) .
C7 C8 1.383(3) .
C7 H7A 0.9500 .
C8 C9 1.387(3) .
C8 H8 0.99(3) .
C9 H9 0.98(3) .
C10 C11 1.399(3) .
C10 C15 1.402(3) .
C11 C12 1.392(3) .
C11 H11 1.03(3) .
C12 C13 1.383(3) .
C12 H12 0.98(3) .
C13 C14 1.383(3) .
C13 H13 0.95(3) .
C14 C15 1.392(3) .
C14 H14 0.99(3) .
C15 H15 0.95(3) .
