#------------------------------------------------------------------------------
#$Date: 2022-02-12 00:53:46 +0200 (Sat, 12 Feb 2022) $
#$Revision: 272932 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/97/7129702.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_7129702
loop_
_publ_author_name
'Gorobets, Evgueni'
'Papatzimas, James W.'
'Dourado, Jorge'
'Yousefalizadeh, Goonay'
'Lee, JinGyu'
'Brownsey, Duncan K.'
'Stamplecoskie, Kevin'
'Davis, Rebecca'
'Derksen, Darren J.'
_publ_section_title
;
 A vinylogous Norrish reaction as a strategy for light-mediated ring
 expansion.
;
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d2cc00513a
_journal_year                    2022
_chemical_formula_moiety         'C11 H13 N O2'
_chemical_formula_sum            'C11 H13 N O2'
_chemical_formula_weight         191.22
_chemical_melting_point          373
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2021-10-06 deposited with the CCDC.	2022-02-03 downloaded from the CCDC.
;
_cell_angle_alpha                106.962(2)
_cell_angle_beta                 92.401(2)
_cell_angle_gamma                105.495(2)
_cell_formula_units_Z            2
_cell_length_a                   5.7936(2)
_cell_length_b                   9.1414(3)
_cell_length_c                   10.1254(3)
_cell_measurement_reflns_used    6568
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.456
_cell_measurement_theta_min      3.700
_cell_volume                     490.09(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_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  0.0438
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17186
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         3.681
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0601 before and 0.0476 after correction. The Ratio of minimum to maximum transmission is 0.8540. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             204
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.157
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0359
_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)+(0.0386P)²+0.1157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1845
_reflns_number_total             2256
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc00513a2.cif
_cod_data_source_block           eg2101_3
_cod_database_code               7129702
_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_max   0.986
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C006(H00A,H00B), C00B(H00D,H00E), C00C(H00F,H00G), C00D(H00H,H00I), C00E(H00J,
 H00K)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.23445(16) 0.13351(10) 0.47093(9) 0.0330(2) Uani 1 1 d . . . . .
O002 O 0.11427(17) -0.13167(10) 0.37023(10) 0.0344(2) Uani 1 1 d . . . . .
N003 N 0.5621(2) 0.65096(13) 0.15170(12) 0.0360(3) Uani 1 1 d . . . . .
C004 C 0.6519(2) 0.12900(13) 0.30634(12) 0.0257(3) Uani 1 1 d . . . . .
C005 C 0.6406(2) 0.57412(13) 0.20162(12) 0.0267(3) Uani 1 1 d . . . . .
C006 C 0.9855(2) 0.46028(14) 0.21984(13) 0.0281(3) Uani 1 1 d . . . . .
H00A H 1.0718 0.4396 0.2934 0.034 Uiso 1 1 calc R . . . .
H00B H 1.0810 0.5601 0.2094 0.034 Uiso 1 1 calc R . . . .
C007 C 0.7457(2) 0.47790(13) 0.26198(12) 0.0243(2) Uani 1 1 d . . . . .
C008 C 0.6221(2) 0.40410(13) 0.34438(12) 0.0251(2) Uani 1 1 d . . . . .
H008 H 0.4736 0.4208 0.3629 0.030 Uiso 1 1 calc R . . . .
C009 C 0.2643(2) 0.01248(13) 0.39003(11) 0.0265(3) Uani 1 1 d . . . . .
C00A C 0.4592(2) 0.00768(14) 0.30274(12) 0.0274(3) Uani 1 1 d . . . . .
H00C H 0.4476 -0.0906 0.2376 0.033 Uiso 1 1 calc R . . . .
C00B C 0.9603(2) 0.32496(14) 0.08337(13) 0.0307(3) Uani 1 1 d . . . . .
H00D H 0.9065 0.3574 0.0073 0.037 Uiso 1 1 calc R . . . .
H00E H 1.1186 0.3111 0.0690 0.037 Uiso 1 1 calc R . . . .
C00C C 0.7865(2) 0.16386(14) 0.07622(12) 0.0281(3) Uani 1 1 d . . . . .
H00F H 0.7998 0.0849 -0.0088 0.034 Uiso 1 1 calc R . . . .
H00G H 0.6232 0.1719 0.0694 0.034 Uiso 1 1 calc R . . . .
C00D C 0.8236(2) 0.10101(14) 0.19988(13) 0.0300(3) Uani 1 1 d . . . . .
H00H H 0.8038 -0.0129 0.1637 0.036 Uiso 1 1 calc R . . . .
H00I H 0.9880 0.1529 0.2458 0.036 Uiso 1 1 calc R . . . .
C00E C 0.7065(2) 0.29596(14) 0.40925(12) 0.0278(3) Uani 1 1 d . . . . .
H00J H 0.6264 0.2909 0.4907 0.033 Uiso 1 1 calc R . . . .
H00K H 0.8791 0.3392 0.4391 0.033 Uiso 1 1 calc R . . . .
H002 H -0.007(3) -0.123(2) 0.4273(19) 0.066(5) 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'
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
_geom_angle_publ_flag
C009 O002 H002 109.2(11) . . ?
C00A C004 C00D 118.68(11) . . ?
C00A C004 C00E 123.92(11) . . ?
C00D C004 C00E 117.38(10) . . ?
N003 C005 C007 178.23(13) . . ?
H00A C006 H00B 107.8 . . ?
C007 C006 H00A 109.0 . . ?
C007 C006 H00B 109.0 . . ?
C007 C006 C00B 112.87(9) . . ?
C00B C006 H00A 109.0 . . ?
C00B C006 H00B 109.0 . . ?
C005 C007 C006 116.60(10) . . ?
C008 C007 C005 119.17(10) . . ?
C008 C007 C006 124.13(11) . . ?
C007 C008 H008 117.8 . . ?
C007 C008 C00E 124.47(11) . . ?
C00E C008 H008 117.8 . . ?
O001 C009 O002 122.24(11) . . ?
O001 C009 C00A 125.80(11) . . ?
O002 C009 C00A 111.94(10) . . ?
C004 C00A C009 127.19(11) . . ?
C004 C00A H00C 116.4 . . ?
C009 C00A H00C 116.4 . . ?
C006 C00B H00D 108.4 . . ?
C006 C00B H00E 108.4 . . ?
H00D C00B H00E 107.5 . . ?
C00C C00B C006 115.32(10) . . ?
C00C C00B H00D 108.4 . . ?
C00C C00B H00E 108.4 . . ?
C00B C00C H00F 108.2 . . ?
C00B C00C H00G 108.2 . . ?
C00B C00C C00D 116.29(10) . . ?
H00F C00C H00G 107.4 . . ?
C00D C00C H00F 108.2 . . ?
C00D C00C H00G 108.2 . . ?
C004 C00D C00C 113.93(10) . . ?
C004 C00D H00H 108.8 . . ?
C004 C00D H00I 108.8 . . ?
C00C C00D H00H 108.8 . . ?
C00C C00D H00I 108.8 . . ?
H00H C00D H00I 107.7 . . ?
C004 C00E H00J 109.5 . . ?
C004 C00E H00K 109.5 . . ?
C008 C00E C004 110.73(9) . . ?
C008 C00E H00J 109.5 . . ?
C008 C00E H00K 109.5 . . ?
H00J C00E H00K 108.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C009 1.2290(14) . ?
O002 C009 1.3235(14) . ?
O002 H002 0.94(2) . ?
N003 C005 1.1465(15) . ?
C004 C00A 1.3377(17) . ?
C004 C00D 1.5107(17) . ?
C004 C00E 1.5171(16) . ?
C005 C007 1.4443(16) . ?
C006 H00A 0.9700 . ?
C006 H00B 0.9700 . ?
C006 C007 1.5062(16) . ?
C006 C00B 1.5330(17) . ?
C007 C008 1.3358(16) . ?
C008 H008 0.9300 . ?
C008 C00E 1.5029(16) . ?
C009 C00A 1.4645(17) . ?
C00A H00C 0.9300 . ?
C00B H00D 0.9700 . ?
C00B H00E 0.9700 . ?
C00B C00C 1.5255(16) . ?
C00C H00F 0.9700 . ?
C00C H00G 0.9700 . ?
C00C C00D 1.5516(16) . ?
C00D H00H 0.9700 . ?
C00D H00I 0.9700 . ?
C00E H00J 0.9700 . ?
C00E H00K 0.9700 . ?
