#------------------------------------------------------------------------------
#$Date: 2019-10-28 00:27:55 +0200 (Mon, 28 Oct 2019) $
#$Revision: 219540 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/44/4514438.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_4514438
loop_
_publ_author_name
'Lorenc, Chris'
'Vibbert, Hunter B.'
'Yao, Chengbo'
'Norton, Jack R.'
'Rauch, Michael'
_publ_section_title
;
 H· Transfer-Initiated Synthesis of γ-Lactams: Interpretation of
 Cycloisomerization and Hydrogenation Ratios
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              10294
_journal_paper_doi               10.1021/acscatal.9b03678
_journal_year                    2019
_chemical_formula_sum            'C17 H25 N O'
_chemical_formula_weight         259.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.8442(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5032(11)
_cell_length_b                   10.3652(10)
_cell_length_c                   12.7281(12)
_cell_measurement_reflns_used    6960
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      30.32
_cell_measurement_theta_min      2.56
_cell_volume                     1479.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      210(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0870
_diffrn_reflns_av_unetI/netI     0.0754
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17180
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         1.816
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.6987
_exptl_absorpt_correction_T_min  0.5897
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.949
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0791
_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)+(0.1092P)²+1.4035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2205
_refine_ls_wR_factor_ref         0.2412
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2307
_reflns_number_total             3019
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs9b03678_si_004.cif
_cod_data_source_block           tns10
_cod_database_code               4514438
_shelx_shelxl_version_number     2014/7
_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_min   0.978
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N N 0.04294(18) 0.7066(2) 0.13229(16) 0.0311(5) Uani 1 1 d . .
O O 0.03698(18) 0.5827(2) 0.28210(18) 0.0554(6) Uani 1 1 d . .
C1 C -0.0084(2) 0.6583(3) 0.2100(2) 0.0391(6) Uani 1 1 d . .
C2 C -0.1294(3) 0.7219(3) 0.1986(3) 0.0492(8) Uani 1 1 d . .
H2A H -0.1149 0.7992 0.2455 0.059 Uiso 1 1 calc R U
C3 C -0.1565(2) 0.7727(2) 0.0860(2) 0.0365(6) Uani 1 1 d . .
H3A H -0.1892 0.6990 0.0393 0.044 Uiso 1 1 calc R U
C4 C -0.0350(2) 0.8002(3) 0.0636(2) 0.0385(6) Uani 1 1 d . .
H4A H -0.0352 0.7865 -0.0126 0.046 Uiso 1 1 calc R U
H4B H -0.0099 0.8889 0.0835 0.046 Uiso 1 1 calc R U
C5 C -0.2188(3) 0.6447(4) 0.2390(3) 0.0654(10) Uani 1 1 d . .
H5A H -0.1846 0.6155 0.3117 0.098 Uiso 1 1 calc R U
H5B H -0.2419 0.5706 0.1925 0.098 Uiso 1 1 calc R U
H5C H -0.2884 0.6974 0.2392 0.098 Uiso 1 1 calc R U
C6 C -0.2460(3) 0.8774(3) 0.0592(3) 0.0484(7) Uani 1 1 d . .
H6A H -0.2225 0.9584 0.0898 0.058 Uiso 1 1 calc R U
C7 C -0.3506(3) 0.8713(3) 0.0001(3) 0.0525(8) Uani 1 1 d . .
H7A H -0.3794 0.7929 -0.0328 0.063 Uiso 1 1 calc R U
H7B H -0.3991 0.9452 -0.0108 0.063 Uiso 1 1 calc R U
C101 C 0.1717(2) 0.6928(2) 0.13375(18) 0.0271(5) Uani 1 1 d . .
C102 C 0.2029(3) 0.5513(3) 0.1215(3) 0.0481(8) Uani 1 1 d . .
H10G H 0.1569 0.5179 0.0528 0.058 Uiso 1 1 calc R U
H10H H 0.1825 0.5005 0.1798 0.058 Uiso 1 1 calc R U
C103 C 0.2455(2) 0.7459(3) 0.2402(2) 0.0379(6) Uani 1 1 d . .
H10D H 0.2259 0.8370 0.2475 0.045 Uiso 1 1 calc R U
H10E H 0.2260 0.6985 0.3007 0.045 Uiso 1 1 calc R U
C104 C 0.2037(2) 0.7699(3) 0.0413(2) 0.0378(6) Uani 1 1 d . .
H10A H 0.1572 0.7380 -0.0278 0.045 Uiso 1 1 calc R U
H10B H 0.1839 0.8611 0.0480 0.045 Uiso 1 1 calc R U
C105 C 0.3373(3) 0.5393(3) 0.1254(3) 0.0599(10) Uani 1 1 d . .
H10K H 0.3575 0.4474 0.1182 0.072 Uiso 1 1 calc R U
C106 C 0.3786(2) 0.7323(3) 0.2432(2) 0.0458(7) Uani 1 1 d . .
H10F H 0.4255 0.7663 0.3125 0.055 Uiso 1 1 calc R U
C107 C 0.3368(2) 0.7565(3) 0.0444(2) 0.0392(6) Uani 1 1 d . .
H10C H 0.3563 0.8068 -0.0155 0.047 Uiso 1 1 calc R U
C108 C 0.4082(3) 0.5907(4) 0.2326(3) 0.0594(10) Uani 1 1 d . .
H10L H 0.3883 0.5415 0.2920 0.071 Uiso 1 1 calc R U
H10M H 0.4937 0.5809 0.2362 0.071 Uiso 1 1 calc R U
C109 C 0.3679(3) 0.6161(3) 0.0325(3) 0.0552(8) Uani 1 1 d . .
H10I H 0.4531 0.6077 0.0339 0.066 Uiso 1 1 calc R U
H10J H 0.3226 0.5825 -0.0365 0.066 Uiso 1 1 calc R U
C110 C 0.4088(3) 0.8078(3) 0.1506(2) 0.0430(7) Uani 1 1 d . .
H11A H 0.3907 0.8994 0.1577 0.052 Uiso 1 1 calc R U
H11B H 0.4941 0.7997 0.1524 0.052 Uiso 1 1 calc R U
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
C1 N C4 111.7(2)
C1 N C101 123.42(19)
C4 N C101 123.11(19)
O C1 N 126.7(2)
O C1 C2 125.1(2)
N C1 C2 108.0(2)
C5 C2 C3 120.6(3)
C5 C2 C1 115.1(3)
C3 C2 C1 103.7(2)
C6 C3 C2 117.7(2)
C6 C3 C4 116.2(2)
C2 C3 C4 104.0(2)
N C4 C3 103.4(2)
C7 C6 C3 128.1(3)
N C101 C102 110.4(2)
N C101 C103 109.37(19)
C102 C101 C103 109.8(2)
N C101 C104 110.46(18)
C102 C101 C104 108.7(2)
C103 C101 C104 108.1(2)
C101 C102 C105 109.4(2)
C106 C103 C101 110.1(2)
C107 C104 C101 110.0(2)
C108 C105 C109 109.9(3)
C108 C105 C102 109.5(3)
C109 C105 C102 109.5(3)
C110 C106 C108 109.5(3)
C110 C106 C103 109.5(2)
C108 C106 C103 109.2(2)
C109 C107 C110 109.4(2)
C109 C107 C104 110.0(2)
C110 C107 C104 109.7(2)
C106 C108 C105 109.4(2)
C107 C109 C105 108.8(2)
C107 C110 C106 109.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N C1 1.355(3)
N C4 1.470(3)
N C101 1.484(3)
O C1 1.231(3)
C1 C2 1.518(4)
C2 C5 1.482(4)
C2 C3 1.493(4)
C3 C6 1.482(4)
C3 C4 1.514(4)
C6 C7 1.271(4)
C101 C102 1.526(3)
C101 C103 1.532(3)
C101 C104 1.533(3)
C102 C105 1.541(4)
C103 C106 1.530(4)
C104 C107 1.529(4)
C105 C108 1.522(5)
C105 C109 1.530(5)
C106 C110 1.519(4)
C106 C108 1.520(5)
C107 C109 1.515(4)
C107 C110 1.515(4)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C4 N C1 O -176.7(3)
C101 N C1 O -11.3(5)
C4 N C1 C2 -1.0(3)
C101 N C1 C2 164.4(2)
O C1 C2 C5 -31.0(5)
N C1 C2 C5 153.3(3)
O C1 C2 C3 -164.9(3)
N C1 C2 C3 19.4(3)
C5 C2 C3 C6 69.9(4)
C1 C2 C3 C6 -159.4(3)
C5 C2 C3 C4 -159.9(3)
C1 C2 C3 C4 -29.2(3)
C1 N C4 C3 -17.5(3)
C101 N C4 C3 177.1(2)
C6 C3 C4 N 159.7(2)
C2 C3 C4 N 28.6(3)
C2 C3 C6 C7 -109.5(4)
C4 C3 C6 C7 126.2(4)
C1 N C101 C102 65.8(3)
C4 N C101 C102 -130.5(3)
C1 N C101 C103 -55.1(3)
C4 N C101 C103 108.6(3)
C1 N C101 C104 -174.0(2)
C4 N C101 C104 -10.2(3)
N C101 C102 C105 -178.9(2)
C103 C101 C102 C105 -58.3(3)
C104 C101 C102 C105 59.8(3)
N C101 C103 C106 179.9(2)
C102 C101 C103 C106 58.7(3)
C104 C101 C103 C106 -59.8(3)
N C101 C104 C107 179.3(2)
C102 C101 C104 C107 -59.5(3)
C103 C101 C104 C107 59.6(3)
C101 C102 C105 C108 59.8(3)
C101 C102 C105 C109 -60.9(3)
C101 C103 C106 C110 60.3(3)
C101 C103 C106 C108 -59.6(3)
C101 C104 C107 C109 60.2(3)
C101 C104 C107 C110 -60.2(3)
C110 C106 C108 C105 -59.0(3)
C103 C106 C108 C105 60.8(3)
C109 C105 C108 C106 59.3(3)
C102 C105 C108 C106 -61.1(3)
C110 C107 C109 C105 60.5(3)
C104 C107 C109 C105 -60.0(3)
C108 C105 C109 C107 -60.0(3)
C102 C105 C109 C107 60.4(3)
C109 C107 C110 C106 -61.1(3)
C104 C107 C110 C106 59.7(3)
C108 C106 C110 C107 60.1(3)
C103 C106 C110 C107 -59.6(3)
