#------------------------------------------------------------------------------
#$Date: 2017-02-05 21:54:36 +0200 (Sun, 05 Feb 2017) $
#$Revision: 191777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/96/7119617.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_7119617
loop_
_publ_author_name
'Ramya Raghunathan'
'Elango Kumarasamy'
'Steffen Jockusch'
'Angel Ugrinov'
'J. Sivaguru'
_publ_section_title
;
 Engaging electronic effects for atropselective [5+2]-photocycloaddition
 of maleimides
;
_journal_name_full               Chem.Commun.
_journal_page_first              8305
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H15 N O2'
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-11-02
_audit_creation_method
;
  Olex2 1.2
  (compiled Oct 26 2012 17:06:22, GUI svn.r4371)
;
_audit_update_record
;
2016-03-22 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9647(2)
_cell_length_b                   9.5076(3)
_cell_length_c                   16.0492(5)
_cell_measurement_reflns_used    5538
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.73
_cell_measurement_theta_min      5.41
_cell_volume                     1215.33(6)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7249
_diffrn_reflns_theta_full        67.72
_diffrn_reflns_theta_max         67.72
_diffrn_reflns_theta_min         5.41
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0551 before and 0.0351 after correction.
The Ratio of minimum to maximum transmission is 0.9158.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.16(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0357P)²+0.2026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0679
_refine_ls_wR_factor_ref         0.0684
_reflns_number_gt                2077
_reflns_number_total             2119
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc02962k2.cif
_cod_data_source_block           2b_PkA
_cod_database_code               7119617
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H12 of C12, H8 of C8, {H6A,H6B} of C6, {H4A,H4B} of C4, H5 of C5, H10 of
  C10, H9 of C9
 At 1.5 times of:
  {H14A,H14B,H14C} of C14, {H1A,H1B,H1C} of C1
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C12(H12)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x+1/2, -y+1/2, -z'
3 '-x, y+1/2, -z+1/2'
4 '-x+1/2, -y, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.11938(12) -0.72296(9) -0.78950(6) 0.0218(2) Uani 1 1 d . . .
O2 O 0.01590(13) -0.26297(10) -0.97666(5) 0.0252(2) Uani 1 1 d . . .
N1 N -0.10901(14) -0.61267(11) -0.84605(6) 0.0160(2) Uani 1 1 d . . .
C1 C 0.24911(17) -0.24649(13) -0.84969(8) 0.0206(3) Uani 1 1 d . . .
H1A H 0.3055 -0.2387 -0.9038 0.031 Uiso 1 1 calc R . .
H1B H 0.3321 -0.2684 -0.8065 0.031 Uiso 1 1 calc R . .
H1C H 0.1938 -0.1572 -0.8364 0.031 Uiso 1 1 calc R . .
C2 C 0.12029(17) -0.36175(13) -0.85332(7) 0.0169(3) Uani 1 1 d . . .
C3 C -0.01697(17) -0.33458(12) -0.91572(8) 0.0178(3) Uani 1 1 d . . .
C4 C -0.19499(17) -0.38419(13) -0.90217(8) 0.0204(3) Uani 1 1 d . . .
H4A H -0.2356 -0.4282 -0.9543 0.024 Uiso 1 1 calc R . .
H4B H -0.2665 -0.3011 -0.8911 0.024 Uiso 1 1 calc R . .
C5 C -0.21790(16) -0.48789(13) -0.83178(8) 0.0166(3) Uani 1 1 d . . .
H5 H -0.1877 -0.4424 -0.7776 0.020 Uiso 1 1 calc R . .
C6 C -0.39733(17) -0.54935(13) -0.82650(8) 0.0186(3) Uani 1 1 d . . .
H6A H -0.4398 -0.5466 -0.7685 0.022 Uiso 1 1 calc R . .
H6B H -0.4755 -0.4965 -0.8628 0.022 Uiso 1 1 calc R . .
C7 C -0.37757(17) -0.69918(13) -0.85629(8) 0.0175(3) Uani 1 1 d . . .
C8 C -0.50079(17) -0.79724(14) -0.87311(8) 0.0220(3) Uani 1 1 d . . .
H8 H -0.6157 -0.7767 -0.8630 0.026 Uiso 1 1 calc R . .
C9 C -0.45231(19) -0.92709(14) -0.90534(9) 0.0245(3) Uani 1 1 d . . .
H9 H -0.5344 -0.9974 -0.9156 0.029 Uiso 1 1 calc R . .
C10 C 0.13923(16) -0.47875(14) -0.80732(8) 0.0176(3) Uani 1 1 d . . .
H10 H 0.2229 -0.4736 -0.7652 0.021 Uiso 1 1 calc R . .
C11 C 0.04855(16) -0.61504(13) -0.81265(7) 0.0163(3) Uani 1 1 d . . .
C12 C -0.28439(19) -0.95419(13) -0.92252(8) 0.0226(3) Uani 1 1 d . . .
H12 H -0.2551 -1.0421 -0.9467 0.027 Uiso 1 1 calc R . .
C13 C -0.15646(17) -0.85705(13) -0.90561(8) 0.0189(3) Uani 1 1 d . . .
C14 C 0.02087(18) -0.88837(14) -0.93081(9) 0.0236(3) Uani 1 1 d . . .
H14A H 0.0215 -0.9649 -0.9717 0.035 Uiso 1 1 calc R . .
H14B H 0.0856 -0.9166 -0.8817 0.035 Uiso 1 1 calc R . .
H14C H 0.0714 -0.8041 -0.9555 0.035 Uiso 1 1 calc R . .
C15 C -0.20852(16) -0.73056(12) -0.86870(7) 0.0165(3) 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
C11 N1 C5 119.26(10) . .
C11 N1 C15 126.92(11) . .
C15 N1 C5 110.10(10) . .
H1A C1 H1B 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
C1 C2 C3 113.37(10) . .
C10 C2 C1 120.39(12) . .
C10 C2 C3 126.11(12) . .
O2 C3 C2 118.25(12) . .
O2 C3 C4 119.42(12) . .
C2 C3 C4 122.19(11) . .
C3 C4 H4A 108.5 . .
C3 C4 H4B 108.5 . .
C3 C4 C5 115.15(11) . .
H4A C4 H4B 107.5 . .
C5 C4 H4A 108.5 . .
C5 C4 H4B 108.5 . .
N1 C5 C4 109.58(10) . .
N1 C5 H5 109.8 . .
N1 C5 C6 104.24(9) . .
C4 C5 H5 109.8 . .
C4 C5 C6 113.53(11) . .
C6 C5 H5 109.8 . .
C5 C6 H6A 110.9 . .
C5 C6 H6B 110.9 . .
H6A C6 H6B 109.0 . .
C7 C6 C5 104.04(10) . .
C7 C6 H6A 110.9 . .
C7 C6 H6B 110.9 . .
C8 C7 C6 128.66(13) . .
C8 C7 C15 120.96(12) . .
C15 C7 C6 110.35(11) . .
C7 C8 H8 120.9 . .
C7 C8 C9 118.30(13) . .
C9 C8 H8 120.9 . .
C8 C9 H9 119.8 . .
C12 C9 C8 120.32(12) . .
C12 C9 H9 119.8 . .
C2 C10 H10 115.3 . .
C2 C10 C11 129.48(12) . .
C11 C10 H10 115.3 . .
O1 C11 N1 123.69(12) . .
O1 C11 C10 119.19(11) . .
N1 C11 C10 117.08(11) . .
C9 C12 H12 118.7 . .
C9 C12 C13 122.61(12) . .
C13 C12 H12 118.7 . .
C12 C13 C14 120.12(12) . .
C12 C13 C15 115.57(12) . .
C15 C13 C14 124.23(12) . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C7 C15 N1 109.49(10) . .
C7 C15 C13 121.96(12) . .
C13 C15 N1 128.29(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C11 1.2285(16) .
O2 C3 1.2201(15) .
N1 C5 1.4873(15) .
N1 C11 1.3648(17) .
N1 C15 1.4200(16) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C1 C2 1.5023(18) .
C2 C3 1.5049(18) .
C2 C10 1.3436(18) .
C3 C4 1.5100(19) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C4 C5 1.5105(17) .
C5 H5 1.0000 .
C5 C6 1.5462(18) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C6 C7 1.5109(18) .
C7 C8 1.3803(19) .
C7 C15 1.3934(19) .
C8 H8 0.9500 .
C8 C9 1.393(2) .
C9 H9 0.9500 .
C9 C12 1.390(2) .
C10 H10 0.9500 .
C10 C11 1.4859(18) .
C12 H12 0.9500 .
C12 C13 1.4017(19) .
C13 C14 1.499(2) .
C13 C15 1.4032(17) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
