#------------------------------------------------------------------------------
#$Date: 2022-02-11 23:53:46 +0100 (vie 11 de feb de 2022) $
#$Revision: 272932 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/97/7129703.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_7129703
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         'C18 H18 N2 O3'
_chemical_formula_sum            'C18 H18 N2 O3'
_chemical_formula_weight         310.34
_chemical_melting_point          484
_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             2018-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-10-06 deposited with the CCDC.	2022-02-03 downloaded from the CCDC.
;
_cell_angle_alpha                95.958(5)
_cell_angle_beta                 90.704(4)
_cell_angle_gamma                98.055(4)
_cell_formula_units_Z            2
_cell_length_a                   5.3474(3)
_cell_length_b                   10.8303(7)
_cell_length_c                   13.5741(8)
_cell_measurement_reflns_used    1320
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.7735
_cell_measurement_theta_min      3.2745
_cell_volume                     773.88(8)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1799
_diffrn_reflns_av_unetI/netI     0.1145
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16188
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.201
_diffrn_reflns_theta_min         3.275
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0840 before and 0.0642 after correction.
The Ratio of minimum to maximum transmission is 0.8567.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1772
_refine_ls_R_factor_gt           0.0879
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1897
_refine_ls_wR_factor_ref         0.2454
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1262
_reflns_number_total             2925
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc00513a2.cif
_cod_data_source_block           l
_cod_database_code               7129703
_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   0.943
_shelx_estimated_absorpt_t_min   0.896
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H) groups
2.a Riding coordinates:
 O3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C9(H9), C13(H13), C14(H14), C16(H16), C17(H17)
;
_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
O1 O 0.7303(7) 0.1126(4) 0.5412(3) 0.0676(11) Uani 1 1 d . . . . .
O2 O 1.2856(7) 0.0981(3) 0.0239(3) 0.0624(10) Uani 1 1 d . . . . .
O3 O 1.3882(6) -0.0510(3) 0.1133(3) 0.0616(10) Uani 1 1 d . . . . .
H3 H 1.5059 -0.0643 0.0537 0.074 Uiso 1 1 d R . . . .
N1 N -0.3409(8) 0.5900(4) 0.6483(3) 0.0658(13) Uani 1 1 d . . . . .
N2 N 0.6357(8) 0.2056(4) 0.4039(3) 0.0556(11) Uani 1 1 d . . . . .
H2 H 0.5408 0.2588 0.3839 0.067 Uiso 1 1 calc R . . . .
C1 C -0.0520(10) 0.4585(5) 0.7353(4) 0.0583(14) Uani 1 1 d . . . . .
C2 C -0.0170(11) 0.4939(5) 0.8460(4) 0.0631(15) Uani 1 1 d . . . . .
H2A H -0.1387 0.4371 0.8807 0.076 Uiso 1 1 calc R . . . .
H2B H -0.0555 0.5804 0.8623 0.076 Uiso 1 1 calc R . . . .
C3 C 0.2503(11) 0.4870(5) 0.8840(4) 0.0631(14) Uani 1 1 d . . . . .
H3A H 0.2851 0.5428 0.9466 0.076 Uiso 1 1 calc R . . . .
H3B H 0.3734 0.5174 0.8349 0.076 Uiso 1 1 calc R . . . .
C4 C 0.2863(11) 0.3528(5) 0.9022(4) 0.0661(15) Uani 1 1 d . . . . .
H4A H 0.4695 0.3482 0.9080 0.079 Uiso 1 1 calc R . . . .
H4B H 0.2107 0.3341 0.9662 0.079 Uiso 1 1 calc R . . . .
C5 C 0.1684(10) 0.2524(5) 0.8207(4) 0.0586(13) Uani 1 1 d . . . . .
H5A H 0.2376 0.1737 0.8284 0.070 Uiso 1 1 calc R . . . .
H5B H -0.0159 0.2362 0.8308 0.070 Uiso 1 1 calc R . . . .
C6 C 0.2106(10) 0.2843(5) 0.7164(4) 0.0545(13) Uani 1 1 d . . . . .
C7 C 0.0587(9) 0.3729(5) 0.6790(4) 0.0587(13) Uani 1 1 d . . . . .
H7 H 0.0367 0.3697 0.6092 0.070 Uiso 1 1 calc R . . . .
C8 C -0.2092(11) 0.5315(5) 0.6854(4) 0.0658(15) Uani 1 1 d . . . . .
C9 C 0.3680(9) 0.2272(5) 0.6567(4) 0.0575(13) Uani 1 1 d . . . . .
H9 H 0.4614 0.1696 0.6836 0.069 Uiso 1 1 calc R . . . .
C10 C 0.4056(10) 0.2490(5) 0.5499(4) 0.0604(14) Uani 1 1 d . . . . .
H10A H 0.4516 0.3401 0.5459 0.072 Uiso 1 1 calc R . . . .
H10B H 0.2436 0.2216 0.5127 0.072 Uiso 1 1 calc R . . . .
C11 C 0.6072(10) 0.1810(5) 0.5005(4) 0.0575(13) Uani 1 1 d . . . . .
C12 C 0.7941(9) 0.1582(5) 0.3326(4) 0.0536(13) Uani 1 1 d . . . . .
C13 C 0.9640(9) 0.0761(5) 0.3487(4) 0.0563(13) Uani 1 1 d . . . . .
H13 H 0.9787 0.0472 0.4119 0.068 Uiso 1 1 calc R . . . .
C14 C 1.1116(10) 0.0367(5) 0.2722(4) 0.0568(13) Uani 1 1 d . . . . .
H14 H 1.2240 -0.0214 0.2831 0.068 Uiso 1 1 calc R . . . .
C15 C 1.1001(9) 0.0797(4) 0.1798(4) 0.0519(12) Uani 1 1 d . . . . .
C16 C 0.9301(9) 0.1623(4) 0.1635(4) 0.0548(13) Uani 1 1 d . . . . .
H16 H 0.9196 0.1926 0.1005 0.066 Uiso 1 1 calc R . . . .
C17 C 0.7769(9) 0.2003(5) 0.2385(4) 0.0566(13) Uani 1 1 d . . . . .
H17 H 0.6588 0.2553 0.2264 0.068 Uiso 1 1 calc R . . . .
C18 C 1.2648(10) 0.0408(5) 0.1003(4) 0.0569(13) Uani 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O3 H3 109.1 . . ?
C11 N2 H2 115.4 . . ?
C11 N2 C12 129.2(4) . . ?
C12 N2 H2 115.4 . . ?
C7 C1 C2 127.3(5) . . ?
C7 C1 C8 117.4(5) . . ?
C8 C1 C2 115.2(4) . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C1 C2 C3 113.0(4) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C2 C3 C4 112.0(5) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 C3 113.8(5) . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C4 C5 H5A 108.4 . . ?
C4 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C6 C5 C4 115.4(5) . . ?
C6 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
C7 C6 C5 117.6(4) . . ?
C9 C6 C5 121.6(5) . . ?
C9 C6 C7 120.6(5) . . ?
C1 C7 C6 125.4(5) . . ?
C1 C7 H7 117.3 . . ?
C6 C7 H7 117.3 . . ?
N1 C8 C1 177.5(6) . . ?
C6 C9 H9 118.0 . . ?
C6 C9 C10 124.1(5) . . ?
C10 C9 H9 118.0 . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C9 C10 C11 114.0(4) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
O1 C11 N2 123.9(5) . . ?
O1 C11 C10 124.7(5) . . ?
N2 C11 C10 111.4(4) . . ?
N2 C12 C17 115.7(4) . . ?
C13 C12 N2 125.1(5) . . ?
C13 C12 C17 119.1(5) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(5) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.2 . . ?
C13 C14 C15 121.7(5) . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C16 118.8(5) . . ?
C14 C15 C18 121.2(5) . . ?
C16 C15 C18 120.0(5) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(5) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.5(5) . . ?
C16 C17 H17 119.7 . . ?
O2 C18 O3 122.6(5) . . ?
O2 C18 C15 119.9(5) . . ?
O3 C18 C15 117.4(5) . . ?
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
O1 C11 1.225(6) . ?
O2 C18 1.261(6) . ?
O3 H3 1.0418 . ?
O3 C18 1.294(5) . ?
N1 C8 1.155(7) . ?
N2 H2 0.8800 . ?
N2 C11 1.371(6) . ?
N2 C12 1.399(5) . ?
C1 C2 1.514(7) . ?
C1 C7 1.346(6) . ?
C1 C8 1.441(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.528(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.537(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.531(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.504(6) . ?
C6 C7 1.466(6) . ?
C6 C9 1.344(6) . ?
C7 H7 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.504(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.514(6) . ?
C12 C13 1.388(6) . ?
C12 C17 1.407(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(7) . ?
C15 C16 1.393(6) . ?
C15 C18 1.467(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.380(6) . ?
C17 H17 0.9500 . ?
