#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/47/1514790.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_1514790
loop_
_publ_author_name
'Cui, Sunliang'
'Zhang, Yan'
'Wu, Qifan'
_publ_section_title
;
 Rh(iii)-catalyzed C--H activation/cycloaddition of benzamides and
 methylenecyclopropanes: divergence in ring formation
;
_journal_issue                   9
_journal_name_full               'Chemical Science'
_journal_page_first              3421
_journal_paper_doi               10.1039/c3sc51424b
_journal_volume                  4
_journal_year                    2013
_chemical_formula_moiety         'C17 H15 N O'
_chemical_formula_sum            'C17 H15 N O'
_chemical_formula_weight         249.30
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.948(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1485(6)
_cell_length_b                   13.8946(8)
_cell_length_c                   10.4647(7)
_cell_measurement_reflns_used    1327
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3656
_cell_measurement_theta_min      3.0457
_cell_volume                     1296.40(15)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_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  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5082
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9690
_exptl_absorpt_correction_T_min  0.9652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0146(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2372
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0419
_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)+(0.0398P)²+0.1650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.1042
_reflns_number_gt                1692
_reflns_number_total             2372
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc51424b.txt
_cod_data_source_block           zhangyan_II_6
_cod_original_cell_volume        1296.40(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1514790
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
O1 O 0.67360(14) -0.02217(8) 0.97541(12) 0.0548(4) Uani 1 1 d .
N1 N 0.54545(15) 0.11141(9) 0.89689(12) 0.0422(4) Uani 1 1 d .
H1 H 0.4796 0.0975 0.9411 0.051 Uiso 1 1 calc R
C1 C 0.8947(2) 0.01382(14) 0.83635(17) 0.0510(5) Uani 1 1 d .
H1A H 0.8948 -0.0457 0.8771 0.061 Uiso 1 1 calc R
C2 C 1.0061(2) 0.03574(17) 0.77229(19) 0.0632(6) Uani 1 1 d .
H2 H 1.0816 -0.0086 0.7697 0.076 Uiso 1 1 calc R
C3 C 1.0050(2) 0.12316(19) 0.71247(19) 0.0676(6) Uani 1 1 d .
H3 H 1.0793 0.1377 0.6677 0.081 Uiso 1 1 calc R
C4 C 0.8952(2) 0.19036(15) 0.71739(17) 0.0574(5) Uani 1 1 d .
H4 H 0.8972 0.2497 0.6768 0.069 Uiso 1 1 calc R
C5 C 0.78147(19) 0.17042(12) 0.78227(14) 0.0411(4) Uani 1 1 d .
C6 C 0.78214(18) 0.07983(11) 0.84065(14) 0.0381(4) Uani 1 1 d .
C7 C 0.66319(18) 0.05256(11) 0.90972(15) 0.0382(4) Uani 1 1 d .
C8 C 0.51844(19) 0.19733(11) 0.81437(14) 0.0397(4) Uani 1 1 d .
H8 H 0.4694 0.2445 0.8605 0.048 Uiso 1 1 calc R
C9 C 0.6670(2) 0.24119(11) 0.80216(15) 0.0423(4) Uani 1 1 d .
C10 C 0.7244(3) 0.32627(13) 0.8900(2) 0.0680(6) Uani 1 1 d .
H10A H 0.6647 0.3479 0.9503 0.082 Uiso 1 1 calc R
H10B H 0.8320 0.3325 0.9222 0.082 Uiso 1 1 calc R
C11 C 0.6620(2) 0.34096(12) 0.74671(19) 0.0655(6) Uani 1 1 d .
H11A H 0.7319 0.3564 0.6924 0.079 Uiso 1 1 calc R
H11B H 0.5648 0.3718 0.7205 0.079 Uiso 1 1 calc R
C12 C 0.41261(18) 0.17908(11) 0.68246(14) 0.0364(4) Uani 1 1 d .
C13 C 0.32263(19) 0.25390(12) 0.62167(16) 0.0453(4) Uani 1 1 d .
H13 H 0.3268 0.3130 0.6640 0.054 Uiso 1 1 calc R
C14 C 0.2275(2) 0.24293(13) 0.50064(17) 0.0507(5) Uani 1 1 d .
H14 H 0.1694 0.2944 0.4615 0.061 Uiso 1 1 calc R
C15 C 0.2187(2) 0.15554(13) 0.43779(17) 0.0535(5) Uani 1 1 d .
H15 H 0.1542 0.1475 0.3561 0.064 Uiso 1 1 calc R
C16 C 0.3057(2) 0.08004(13) 0.49616(18) 0.0554(5) Uani 1 1 d .
H16 H 0.2995 0.0208 0.4540 0.066 Uiso 1 1 calc R
C17 C 0.4025(2) 0.09182(12) 0.61737(17) 0.0471(4) Uani 1 1 d .
H17 H 0.4615 0.0404 0.6555 0.057 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 N1 C8 125.84(14)
C7 N1 H1 117.1
C8 N1 H1 117.1
C2 C1 C6 120.43(18)
C2 C1 H1A 119.8
C6 C1 H1A 119.8
C3 C2 C1 119.4(2)
C3 C2 H2 120.3
C1 C2 H2 120.3
C2 C3 C4 121.00(19)
C2 C3 H3 119.5
C4 C3 H3 119.5
C3 C4 C5 120.87(19)
C3 C4 H4 119.6
C5 C4 H4 119.6
C4 C5 C6 117.50(17)
C4 C5 C9 124.35(16)
C6 C5 C9 117.98(14)
C1 C6 C5 120.76(16)
C1 C6 C7 118.53(15)
C5 C6 C7 120.70(15)
O1 C7 N1 122.00(15)
O1 C7 C6 120.75(15)
N1 C7 C6 117.25(14)
N1 C8 C12 112.92(13)
N1 C8 C9 109.93(13)
C12 C8 C9 112.96(12)
N1 C8 H8 106.9
C12 C8 H8 106.9
C9 C8 H8 106.9
C5 C9 C11 121.30(16)
C5 C9 C10 116.23(15)
C11 C9 C10 59.37(11)
C5 C9 C8 114.71(13)
C11 C9 C8 116.90(16)
C10 C9 C8 117.11(16)
C11 C10 C9 59.73(11)
C11 C10 H10A 117.8
C9 C10 H10A 117.8
C11 C10 H10B 117.8
C9 C10 H10B 117.8
H10A C10 H10B 114.9
C10 C11 C9 60.90(11)
C10 C11 H11A 117.7
C9 C11 H11A 117.7
C10 C11 H11B 117.7
C9 C11 H11B 117.7
H11A C11 H11B 114.8
C17 C12 C13 117.60(15)
C17 C12 C8 123.52(14)
C13 C12 C8 118.87(13)
C14 C13 C12 121.78(15)
C14 C13 H13 119.1
C12 C13 H13 119.1
C15 C14 C13 119.74(16)
C15 C14 H14 120.1
C13 C14 H14 120.1
C16 C15 C14 119.70(16)
C16 C15 H15 120.2
C14 C15 H15 120.2
C15 C16 C17 120.32(16)
C15 C16 H16 119.8
C17 C16 H16 119.8
C12 C17 C16 120.87(16)
C12 C17 H17 119.6
C16 C17 H17 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2371(18)
N1 C7 1.335(2)
N1 C8 1.4617(19)
N1 H1 0.8600
C1 C2 1.373(3)
C1 C6 1.387(2)
C1 H1A 0.9300
C2 C3 1.365(3)
C2 H2 0.9300
C3 C4 1.381(3)
C3 H3 0.9300
C4 C5 1.391(2)
C4 H4 0.9300
C5 C6 1.399(2)
C5 C9 1.485(2)
C6 C7 1.484(2)
C8 C12 1.519(2)
C8 C9 1.521(2)
C8 H8 0.9800
C9 C11 1.499(2)
C9 C10 1.517(2)
C10 C11 1.494(3)
C10 H10A 0.9700
C10 H10B 0.9700
C11 H11A 0.9700
C11 H11B 0.9700
C12 C17 1.384(2)
C12 C13 1.389(2)
C13 C14 1.375(2)
C13 H13 0.9300
C14 C15 1.375(2)
C14 H14 0.9300
C15 C16 1.375(2)
C15 H15 0.9300
C16 C17 1.385(2)
C16 H16 0.9300
C17 H17 0.9300
