#------------------------------------------------------------------------------
#$Date: 2017-03-04 09:51:59 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193237 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/22/4032235.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_4032235
loop_
_publ_author_name
'Bera, Sourav Sekhar'
'Debbarma, Suvankar'
'Ghosh, Avick Kumar'
'Chand, Santanu'
'Maji, Modhu Sudan'
_publ_section_title
;
 Cp*Co(III)-Catalyzed syn-Selective C-H Hydroarylation of Alkynes Using
 Benzamides: An Approach Toward Highly Conjugated Organic Frameworks.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              420
_journal_page_last               430
_journal_paper_doi               10.1021/acs.joc.6b02516
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C25 H24 F N O'
_chemical_formula_weight         373.45
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 102.399(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   14.384(5)
_cell_length_b                   10.019(5)
_cell_length_c                   15.264(5)
_cell_measurement_reflns_used    8245
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1
_cell_measurement_theta_min      2.2
_cell_volume                     2148.4(15)
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45  (Bruker, 2003)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1280
_diffrn_reflns_av_sigmaI/netI    0.1009
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26830
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9498
_exptl_absorpt_correction_T_min  0.9088
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.801
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.801
_refine_ls_R_factor_all          0.1800
_refine_ls_R_factor_gt           0.0624
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0809P)²+0.9797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1425
_refine_ls_wR_factor_ref         0.1900
_reflns_number_gt                1642
_reflns_number_total             4355
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02516_si_002.cif
_cod_data_source_block           ffff
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4032235
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.75091(16) 0.6362(2) 0.25353(15) 0.0717(7) Uani 1 1 d .
F1 F 0.86479(15) 0.4770(2) 0.41917(13) 0.0959(7) Uani 1 1 d .
N1 N 0.69922(19) 0.4241(3) 0.21784(18) 0.0587(7) Uani 1 1 d .
C1 C 0.8672(2) 0.4627(3) 0.2659(2) 0.0562(8) Uani 1 1 d .
C7 C 0.8734(2) 0.4438(3) 0.1010(2) 0.0579(8) Uani 1 1 d .
C8 C 0.8793(2) 0.3221(3) 0.0455(2) 0.0603(9) Uani 1 1 d .
C14 C 0.8337(2) 0.5605(3) 0.0678(2) 0.0628(9) Uani 1 1 d .
H14 H 0.8352 0.6270 0.1106 0.075 Uiso 1 1 calc R
C15 C 0.7884(2) 0.6013(3) -0.0246(2) 0.0647(9) Uani 1 1 d .
C21 C 0.7662(2) 0.5161(3) 0.2448(2) 0.0570(8) Uani 1 1 d .
C6 C 0.9168(2) 0.4305(3) 0.1992(2) 0.0579(8) Uani 1 1 d .
C22 C 0.5955(2) 0.4506(3) 0.1869(2) 0.0673(9) Uani 1 1 d .
C5 C 1.0106(3) 0.3841(4) 0.2256(3) 0.0746(10) Uani 1 1 d .
H5 H 1.0438 0.3611 0.1818 0.089 Uiso 1 1 calc R
C2 C 0.9150(3) 0.4474(3) 0.3544(2) 0.0699(10) Uani 1 1 d .
C3 C 1.0068(3) 0.4041(4) 0.3806(3) 0.0828(11) Uani 1 1 d .
H3 H 1.0361 0.3968 0.4410 0.099 Uiso 1 1 calc R
C13 C 0.9495(3) 0.3067(4) -0.0016(3) 0.0889(12) Uani 1 1 d .
H13 H 0.9943 0.3741 -0.0001 0.107 Uiso 1 1 calc R
C16 C 0.7600(3) 0.7327(4) -0.0382(3) 0.0940(13) Uani 1 1 d .
H16 H 0.7689 0.7902 0.0107 0.113 Uiso 1 1 calc R
C9 C 0.8139(3) 0.2199(4) 0.0416(2) 0.0803(11) Uani 1 1 d .
H9 H 0.7656 0.2272 0.0733 0.096 Uiso 1 1 calc R
C4 C 1.0546(3) 0.3716(4) 0.3142(3) 0.0866(12) Uani 1 1 d .
H4 H 1.1170 0.3411 0.3296 0.104 Uiso 1 1 calc R
C20 C 0.7716(3) 0.5195(4) -0.0996(3) 0.0937(13) Uani 1 1 d .
H20 H 0.7881 0.4297 -0.0932 0.112 Uiso 1 1 calc R
C11 C 0.8889(4) 0.0937(4) -0.0559(3) 0.0914(13) Uani 1 1 d .
H11 H 0.8914 0.0180 -0.0906 0.110 Uiso 1 1 calc R
C10 C 0.8195(4) 0.1076(4) -0.0088(3) 0.0951(13) Uani 1 1 d .
H10 H 0.7750 0.0398 -0.0105 0.114 Uiso 1 1 calc R
C25 C 0.5494(3) 0.3192(4) 0.1522(3) 0.1181(17) Uani 1 1 d .
H25A H 0.5592 0.2551 0.2000 0.177 Uiso 1 1 calc R
H25B H 0.5775 0.2869 0.1046 0.177 Uiso 1 1 calc R
H25C H 0.4824 0.3325 0.1300 0.177 Uiso 1 1 calc R
C18 C 0.7060(3) 0.6995(5) -0.1957(3) 0.0940(13) Uani 1 1 d .
H18 H 0.6808 0.7323 -0.2529 0.113 Uiso 1 1 calc R
C19 C 0.7310(3) 0.5685(5) -0.1836(3) 0.1000(14) Uani 1 1 d .
H19 H 0.7206 0.5112 -0.2327 0.120 Uiso 1 1 calc R
C12 C 0.9552(3) 0.1929(5) -0.0515(3) 0.1014(14) Uani 1 1 d .
H12 H 1.0042 0.1838 -0.0821 0.122 Uiso 1 1 calc R
C24 C 0.5805(3) 0.5509(4) 0.1107(3) 0.0979(13) Uani 1 1 d .
H24A H 0.6094 0.6343 0.1323 0.147 Uiso 1 1 calc R
H24B H 0.5135 0.5639 0.0880 0.147 Uiso 1 1 calc R
H24C H 0.6090 0.5179 0.0635 0.147 Uiso 1 1 calc R
C23 C 0.5559(3) 0.5048(5) 0.2648(3) 0.1106(15) Uani 1 1 d .
H23A H 0.5866 0.5878 0.2847 0.166 Uiso 1 1 calc R
H23B H 0.5676 0.4416 0.3132 0.166 Uiso 1 1 calc R
H23C H 0.4886 0.5189 0.2454 0.166 Uiso 1 1 calc R
C17 C 0.7182(4) 0.7817(5) -0.1230(3) 0.1193(17) Uani 1 1 d .
H17 H 0.6988 0.8703 -0.1300 0.143 Uiso 1 1 calc R
H1A H 0.717(2) 0.343(3) 0.2169(19) 0.063(10) 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'
O O 0.0106 0.0060 '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
C21 N1 C22 125.7(3)
C2 C1 C6 117.4(3)
C2 C1 C21 119.9(3)
C6 C1 C21 122.7(3)
C14 C7 C6 120.2(3)
C14 C7 C8 124.2(3)
C6 C7 C8 115.5(3)
C13 C8 C9 117.8(3)
C13 C8 C7 121.9(3)
C9 C8 C7 120.4(3)
C7 C14 C15 131.4(3)
C16 C15 C20 116.5(3)
C16 C15 C14 117.6(3)
C20 C15 C14 125.9(3)
O1 C21 N1 125.0(3)
O1 C21 C1 120.3(3)
N1 C21 C1 114.7(3)
C1 C6 C5 118.4(3)
C1 C6 C7 122.6(3)
C5 C6 C7 119.0(3)
N1 C22 C25 106.8(3)
N1 C22 C24 109.2(3)
C25 C22 C24 109.1(3)
N1 C22 C23 109.4(3)
C25 C22 C23 111.9(3)
C24 C22 C23 110.3(3)
C4 C5 C6 121.7(4)
C3 C2 F1 118.8(3)
C3 C2 C1 124.5(3)
F1 C2 C1 116.7(3)
C2 C3 C4 117.5(4)
C8 C13 C12 121.4(4)
C15 C16 C17 122.0(4)
C10 C9 C8 120.6(4)
C5 C4 C3 120.5(4)
C19 C20 C15 121.4(4)
C10 C11 C12 118.9(4)
C11 C10 C9 121.2(4)
C17 C18 C19 119.2(4)
C18 C19 C20 121.0(4)
C11 C12 C13 120.1(4)
C18 C17 C16 119.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C21 1.236(3)
F1 C2 1.376(4)
N1 C21 1.332(4)
N1 C22 1.489(4)
C1 C2 1.387(4)
C1 C6 1.401(4)
C1 C21 1.517(4)
C7 C14 1.352(4)
C7 C6 1.500(4)
C7 C8 1.498(4)
C8 C13 1.368(4)
C8 C9 1.384(4)
C14 C15 1.478(4)
C15 C16 1.381(5)
C15 C20 1.387(5)
C6 C5 1.402(4)
C22 C25 1.517(5)
C22 C24 1.517(5)
C22 C23 1.524(5)
C5 C4 1.370(5)
C2 C3 1.366(5)
C3 C4 1.380(5)
C13 C12 1.383(5)
C16 C17 1.395(5)
C9 C10 1.375(5)
C20 C19 1.380(5)
C11 C10 1.357(5)
C11 C12 1.370(5)
C18 C17 1.362(6)
C18 C19 1.363(5)
