#------------------------------------------------------------------------------
#$Date: 2020-01-04 02:29:33 +0200 (Sat, 04 Jan 2020) $
#$Revision: 246504 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/39/4133907.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_4133907
loop_
_publ_author_name
'Wang, Yidong'
'Zhu, Jin'
'Durham, Austin C.'
'Lindberg, Haley'
'Wang, Yi-Ming'
_publ_section_title
;
 α-C-H Functionalization of π-Bonds Using Iron Complexes: Catalytic
 Hydroxyalkylation of Alkynes and Alkenes.
;
_journal_issue                   50
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              19594
_journal_page_last               19599
_journal_paper_doi               10.1021/jacs.9b11716
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C25 H21 N O2'
_chemical_formula_weight         367.43
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                66.5672(12)
_cell_angle_beta                 70.0783(15)
_cell_angle_gamma                65.0638(13)
_cell_formula_units_Z            2
_cell_length_a                   9.7884(3)
_cell_length_b                   10.4455(3)
_cell_length_c                   11.6886(3)
_cell_measurement_reflns_used    7828
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.301
_cell_measurement_theta_min      4.215
_cell_volume                     972.56(5)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13548
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.296
_diffrn_reflns_theta_min         4.214
_diffrn_source                   'Bruker X8 Prospector Ultra Cu IMuS'
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       'irregular prism'
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.637
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         3469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.637
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0344
_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)+(0.0680P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1280
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3214
_reflns_number_total             3469
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b11716_si_001.cif
_cod_data_source_block           acd26_1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'direct methods' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4133907
_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   0.896
_shelx_estimated_absorpt_t_max   0.918
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.25594(9) 0.53506(8) 0.10547(7) 0.0283(2) Uani 1 1 d
H1O H 0.3578(19) 0.5102(18) 0.1075(15) 0.041(4) Uiso 1 1 d
C1 C 0.22770(12) 0.64708(11) -0.01005(9) 0.0241(3) Uani 1 1 d
C8 C 0.32121(12) 0.58689(11) -0.12560(9) 0.0243(2) Uani 1 1 d
O2 O 0.46157(9) 0.52985(9) -0.15147(7) 0.0326(2) Uani 1 1 d
C2 C 0.06440(12) 0.68986(11) -0.02189(9) 0.0234(2) Uani 1 1 d
C3 C -0.07451(12) 0.74324(11) 0.05552(10) 0.0256(2) Uani 1 1 d
H3 H -0.0764(15) 0.7568(16) 0.1340(14) 0.032(3) Uiso 1 1 d
C4 C -0.21250(12) 0.77153(11) 0.02313(10) 0.0267(3) Uani 1 1 d
C5 C -0.20512(12) 0.74516(12) -0.08679(11) 0.0289(3) Uani 1 1 d
H5 H -0.3047(16) 0.7656(16) -0.1082(14) 0.033(3) Uiso 1 1 d
C6 C -0.06557(13) 0.69158(12) -0.16620(10) 0.0281(3) Uani 1 1 d
H6 H -0.0622(15) 0.6718(15) -0.2433(14) 0.030(3) Uiso 1 1 d
C7 C 0.06744(12) 0.66476(11) -0.13124(9) 0.0238(2) Uani 1 1 d
N1 N 0.22209(10) 0.60542(10) -0.19250(8) 0.0249(2) Uani 1 1 d
C9 C 0.27138(13) 0.77773(12) -0.02029(10) 0.0288(3) Uani 1 1 d
H9A H 0.2046(16) 0.8180(16) 0.0476(14) 0.031(3) Uiso 1 1 d
H9B H 0.3799(16) 0.7361(15) -0.0096(13) 0.030(3) Uiso 1 1 d
C10 C 0.25856(13) 0.89571(12) -0.14131(11) 0.0295(3) Uani 1 1 d
C11 C 0.25169(13) 0.99296(12) -0.24018(11) 0.0293(3) Uani 1 1 d
C12 C 0.10200(13) 1.20174(13) -0.39164(12) 0.0320(3) Uani 1 1 d
H12 H 0.010(2) 1.1829(18) -0.3357(16) 0.044(4) Uiso 1 1 d
C13 C 0.09541(14) 1.31514(14) -0.50558(12) 0.0356(3) Uani 1 1 d
H13 H -0.006(2) 1.375(2) -0.5270(17) 0.053(4) Uiso 1 1 d
C14 C 0.22873(16) 1.33904(13) -0.58659(11) 0.0362(3) Uani 1 1 d
H14 H 0.2238(19) 1.4179(19) -0.6675(17) 0.048(4) Uiso 1 1 d
C15 C 0.36992(15) 1.25079(14) -0.55325(12) 0.0372(3) Uani 1 1 d
H15 H 0.462(2) 1.272(2) -0.6105(18) 0.058(5) Uiso 1 1 d
C16 C 0.37788(13) 1.13814(13) -0.43855(11) 0.0317(3) Uani 1 1 d
H16 H 0.4812(19) 1.0776(18) -0.4165(15) 0.043(4) Uiso 1 1 d
C17 C 0.24382(12) 1.11179(11) -0.35766(10) 0.0263(3) Uani 1 1 d
C18 C 0.26804(13) 0.55231(12) -0.30193(10) 0.0268(3) Uani 1 1 d
H18A H 0.2030(16) 0.4975(16) -0.2897(14) 0.035(3) Uiso 1 1 d
H18B H 0.3722(16) 0.4819(16) -0.2986(13) 0.033(3) Uiso 1 1 d
C19 C 0.31285(12) 0.62491(13) -0.53821(11) 0.0282(3) Uani 1 1 d
H19 H 0.3498(17) 0.5208(18) -0.5305(14) 0.037(4) Uiso 1 1 d
C20 C 0.31060(13) 0.72755(14) -0.65829(11) 0.0323(3) Uani 1 1 d
H20 H 0.3459(18) 0.6944(18) -0.7336(16) 0.043(4) Uiso 1 1 d
C21 C 0.25880(13) 0.87736(13) -0.67156(11) 0.0332(3) Uani 1 1 d
H21 H 0.2573(16) 0.9501(16) -0.7569(14) 0.036(3) Uiso 1 1 d
C22 C 0.20966(13) 0.92401(13) -0.56424(12) 0.0324(3) Uani 1 1 d
H22 H 0.1737(19) 1.030(2) -0.5752(17) 0.052(4) Uiso 1 1 d
C23 C 0.21164(12) 0.82081(12) -0.44304(11) 0.0285(3) Uani 1 1 d
H23 H 0.1729(16) 0.8546(16) -0.3675(14) 0.035(3) Uiso 1 1 d
C24 C 0.26306(11) 0.67114(12) -0.42973(10) 0.0241(2) Uani 1 1 d
C25 C -0.36641(13) 0.82956(14) 0.10587(12) 0.0340(3) Uani 1 1 d
H25A H -0.3602(18) 0.7901(19) 0.1985(17) 0.048(4) Uiso 1 1 d
H25B H -0.442(2) 0.801(2) 0.0986(18) 0.057(5) Uiso 1 1 d
H25C H -0.4025(19) 0.936(2) 0.0836(17) 0.053(4) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 O1 H1O 107.8(10)
O1 C1 C2 110.78(8)
O1 C1 C9 109.22(8)
C2 C1 C9 114.00(9)
O1 C1 C8 110.73(8)
C2 C1 C8 101.70(8)
C9 C1 C8 110.24(8)
O2 C8 N1 125.38(10)
O2 C8 C1 125.91(9)
N1 C8 C1 108.70(8)
C3 C2 C7 120.09(9)
C3 C2 C1 131.10(9)
C7 C2 C1 108.80(9)
C2 C3 C4 119.44(10)
C2 C3 H3 120.0(8)
C4 C3 H3 120.5(8)
C5 C4 C3 118.93(10)
C5 C4 C25 120.27(10)
C3 C4 C25 120.81(10)
C6 C5 C4 122.31(10)
C6 C5 H5 119.9(8)
C4 C5 H5 117.8(8)
C7 C6 C5 117.15(10)
C7 C6 H6 121.5(8)
C5 C6 H6 121.3(8)
C6 C7 C2 122.09(10)
C6 C7 N1 128.00(9)
C2 C7 N1 109.87(9)
C8 N1 C7 110.79(8)
C8 N1 C18 123.97(9)
C7 N1 C18 124.72(8)
C10 C9 C1 114.02(8)
C10 C9 H9A 108.8(8)
C1 C9 H9A 107.8(8)
C10 C9 H9B 109.4(8)
C1 C9 H9B 106.7(8)
H9A C9 H9B 110.1(11)
C11 C10 C9 178.09(11)
C10 C11 C17 178.72(11)
C13 C12 C17 119.99(11)
C13 C12 H12 120.8(10)
C17 C12 H12 119.2(10)
C14 C13 C12 120.39(11)
C14 C13 H13 121.8(10)
C12 C13 H13 117.8(10)
C13 C14 C15 119.98(11)
C13 C14 H14 120.2(10)
C15 C14 H14 119.9(10)
C14 C15 C16 120.18(11)
C14 C15 H15 118.7(11)
C16 C15 H15 121.1(11)
C15 C16 C17 120.00(10)
C15 C16 H16 118.3(9)
C17 C16 H16 121.7(9)
C16 C17 C12 119.44(10)
C16 C17 C11 120.26(10)
C12 C17 C11 120.30(10)
N1 C18 C24 115.21(8)
N1 C18 H18A 108.6(9)
C24 C18 H18A 109.2(9)
N1 C18 H18B 105.0(8)
C24 C18 H18B 111.2(8)
H18A C18 H18B 107.3(12)
C20 C19 C24 120.47(10)
C20 C19 H19 119.3(9)
C24 C19 H19 120.3(9)
C19 C20 C21 120.19(10)
C19 C20 H20 120.0(10)
C21 C20 H20 119.8(10)
C20 C21 C22 119.63(11)
C20 C21 H21 120.1(9)
C22 C21 H21 120.3(9)
C23 C22 C21 120.31(11)
C23 C22 H22 121.1(11)
C21 C22 H22 118.6(11)
C22 C23 C24 120.06(10)
C22 C23 H23 119.9(9)
C24 C23 H23 120.0(9)
C23 C24 C19 119.33(10)
C23 C24 C18 123.37(9)
C19 C24 C18 117.30(9)
C4 C25 H25A 111.2(9)
C4 C25 H25B 111.1(11)
H25A C25 H25B 107.2(15)
C4 C25 H25C 111.8(10)
H25A C25 H25C 107.1(14)
H25B C25 H25C 108.2(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4121(11)
O1 H1O 0.925(16)
C1 C2 1.5077(14)
C1 C9 1.5450(14)
C1 C8 1.5507(14)
C8 O2 1.2264(13)
C8 N1 1.3522(14)
C2 C3 1.3791(15)
C2 C7 1.3919(14)
C3 C4 1.4064(15)
C3 H3 0.976(15)
C4 C5 1.3904(16)
C4 C25 1.5086(15)
C5 C6 1.3946(16)
C5 H5 1.004(14)
C6 C7 1.3801(14)
C6 H6 0.989(15)
C7 N1 1.4183(13)
N1 C18 1.4519(14)
C9 C10 1.4627(14)
C9 H9A 0.956(15)
C9 H9B 0.995(14)
C10 C11 1.1974(17)
C11 C17 1.4381(15)
C12 C13 1.3858(17)
C12 C17 1.3952(16)
C12 H12 0.963(17)
C13 C14 1.3808(19)
C13 H13 0.981(17)
C14 C15 1.3852(19)
C14 H14 0.976(18)
C15 C16 1.3883(17)
C15 H15 0.976(19)
C16 C17 1.3942(17)
C16 H16 0.999(17)
C18 C24 1.5161(14)
C18 H18A 0.967(14)
C18 H18B 0.977(14)
C19 C20 1.3872(16)
C19 C24 1.3949(15)
C19 H19 0.967(16)
C20 C21 1.3861(18)
C20 H20 0.973(17)
C21 C22 1.3855(17)
C21 H21 0.985(15)
C22 C23 1.3985(16)
C22 H22 0.973(19)
C23 C24 1.3850(16)
C23 H23 0.976(15)
C25 H25A 1.007(18)
C25 H25B 0.942(19)
C25 H25C 0.963(19)
