#------------------------------------------------------------------------------
#$Date: 2017-02-05 21:54:36 +0200 (Sun, 05 Feb 2017) $
#$Revision: 191777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/96/7119618.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_7119618
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         'C14 H12 Br N O2'
_chemical_formula_sum            'C14 H12 Br N O2'
_chemical_formula_weight         306.16
_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
_audit_creation_date             2014-07-02
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_audit_update_record
;
2016-03-22 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5431(8)
_cell_length_b                   9.8089(8)
_cell_length_c                   14.6636(12)
_cell_measurement_reflns_used    4182
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      2.50
_cell_volume                     1228.79(18)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_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  0.0252
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9446
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.089
_diffrn_reflns_theta_min         2.498
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.338
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0634 before and 0.0363 after correction.
The Ratio of minimum to maximum transmission is 0.8465.
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    1.655
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.417(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0204
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0203P)²+0.1990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0425
_refine_ls_wR_factor_ref         0.0436
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2542
_reflns_number_total             2719
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc02962k2.cif
_cod_data_source_block           3c
_cod_database_code               7119618
_shelxl_version_number           2014-1
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
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:
 C1(H1), C2(H2), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-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_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
Br1 Br 0.26017(3) 1.22124(3) 0.36424(2) 0.01455(8) Uani 1 1 d . . . . .
O1 O 0.3129(2) 1.2724(2) 0.70680(13) 0.0190(4) Uani 1 1 d . . . . .
O2 O 0.0588(2) 0.99782(19) 0.44981(12) 0.0141(4) Uani 1 1 d . . . . .
N1 N 0.2232(3) 0.9430(2) 0.56801(14) 0.0098(5) Uani 1 1 d . . . . .
C1 C 0.0658(4) 0.5675(3) 0.66468(19) 0.0166(7) Uani 1 1 d . . . . .
H1 H 0.0355 0.4783 0.6828 0.020 Uiso 1 1 calc R . . . .
C2 C 0.2248(4) 0.6014(3) 0.66071(16) 0.0142(6) Uani 1 1 d . . . . .
H2 H 0.3028 0.5378 0.6787 0.017 Uiso 1 1 calc R . . . .
C3 C 0.2653(3) 0.7304(2) 0.62981(15) 0.0113(5) Uani 1 1 d . . . . .
C4 C 0.4250(3) 0.7955(3) 0.62332(18) 0.0106(6) Uani 1 1 d . . . . .
H4A H 0.4890 0.7509 0.5756 0.013 Uiso 1 1 calc R . . . .
H4B H 0.4809 0.7897 0.6823 0.013 Uiso 1 1 calc R . . . .
C5 C 0.3902(3) 0.9451(3) 0.59809(19) 0.0106(6) Uani 1 1 d . . . . .
H5 H 0.4587 0.9739 0.5462 0.013 Uiso 1 1 calc R . . . .
C6 C 0.4040(3) 1.0470(3) 0.67566(19) 0.0141(6) Uani 1 1 d . . . . .
H6A H 0.3437 1.0131 0.7287 0.017 Uiso 1 1 calc R . . . .
H6B H 0.5151 1.0540 0.6942 0.017 Uiso 1 1 calc R . . . .
C7 C 0.3448(3) 1.1870(3) 0.65000(18) 0.0114(6) Uani 1 1 d . . . . .
C8 C 0.3332(3) 1.2264(3) 0.55085(17) 0.0134(6) Uani 1 1 d . . . . .
H8 H 0.3779 1.3111 0.5335 0.016 Uiso 1 1 calc R . . . .
C9 C -0.0477(3) 0.6626(3) 0.64239(19) 0.0151(6) Uani 1 1 d . . . . .
H9 H -0.1548 0.6381 0.6485 0.018 Uiso 1 1 calc R . . . .
C10 C -0.0104(3) 0.7942(3) 0.61104(17) 0.0117(6) Uani 1 1 d . . . . .
C11 C 0.1493(3) 0.8215(3) 0.60037(18) 0.0105(6) Uani 1 1 d . . . . .
C12 C 0.2655(4) 1.1525(2) 0.48539(15) 0.0107(5) Uani 1 1 d . . . . .
C13 C 0.1726(3) 1.0226(3) 0.49733(17) 0.0112(6) Uani 1 1 d . . . . .
C14 C -0.1370(3) 0.8994(3) 0.5978(2) 0.0165(6) Uani 1 1 d . . . . .
H14A H -0.0988 0.9886 0.6180 0.025 Uiso 1 1 calc GR . . . .
H14B H -0.2292 0.8739 0.6336 0.025 Uiso 1 1 calc GR . . . .
H14C H -0.1652 0.9040 0.5330 0.025 Uiso 1 1 calc GR . . . .
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'
Br Br -0.2901 2.4595 '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 109.6(2) . .
C13 N1 C5 121.2(2) . .
C13 N1 C11 126.0(2) . .
C2 C1 H1 119.7 . .
C9 C1 H1 119.7 . .
C9 C1 C2 120.6(3) . .
C1 C2 H2 120.9 . .
C3 C2 C1 118.2(3) . .
C3 C2 H2 120.9 . .
C2 C3 C4 129.2(2) . .
C2 C3 C11 120.4(3) . .
C11 C3 C4 110.4(2) . .
C3 C4 H4A 110.9 . .
C3 C4 H4B 110.9 . .
C3 C4 C5 104.1(2) . .
H4A C4 H4B 109.0 . .
C5 C4 H4A 110.9 . .
C5 C4 H4B 110.9 . .
N1 C5 C4 104.0(2) . .
N1 C5 H5 109.8 . .
N1 C5 C6 107.7(2) . .
C4 C5 H5 109.8 . .
C6 C5 C4 115.6(2) . .
C6 C5 H5 109.8 . .
C5 C6 H6A 109.1 . .
C5 C6 H6B 109.1 . .
H6A C6 H6B 107.8 . .
C7 C6 C5 112.7(2) . .
C7 C6 H6A 109.1 . .
C7 C6 H6B 109.1 . .
O1 C7 C6 122.2(2) . .
O1 C7 C8 118.1(3) . .
C8 C7 C6 119.7(2) . .
C7 C8 H8 117.2 . .
C12 C8 C7 125.7(3) . .
C12 C8 H8 117.2 . .
C1 C9 H9 118.8 . .
C1 C9 C10 122.4(3) . .
C10 C9 H9 118.8 . .
C9 C10 C14 120.5(2) . .
C11 C10 C9 115.6(3) . .
C11 C10 C14 123.7(3) . .
C3 C11 N1 108.8(2) . .
C10 C11 N1 128.8(3) . .
C10 C11 C3 122.2(3) . .
C8 C12 Br1 119.4(2) . .
C8 C12 C13 127.0(2) . .
C13 C12 Br1 113.25(17) . .
O2 C13 N1 124.8(3) . .
O2 C13 C12 121.3(2) . .
N1 C13 C12 113.8(2) . .
C10 C14 H14A 109.5 . .
C10 C14 H14B 109.5 . .
C10 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C12 1.901(2) .
O1 C7 1.212(3) .
O2 C13 1.221(3) .
N1 C5 1.493(3) .
N1 C11 1.429(3) .
N1 C13 1.368(3) .
C1 H1 0.9500 .
C1 C2 1.399(4) .
C1 C9 1.385(4) .
C2 H2 0.9500 .
C2 C3 1.388(4) .
C3 C4 1.509(3) .
C3 C11 1.402(4) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C4 C5 1.542(4) .
C5 H5 1.0000 .
C5 C6 1.519(4) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C6 C7 1.511(4) .
C7 C8 1.508(4) .
C8 H8 0.9500 .
C8 C12 1.334(4) .
C9 H9 0.9500 .
C9 C10 1.407(4) .
C10 C11 1.400(4) .
C10 C14 1.507(4) .
C12 C13 1.512(4) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
Br1 C12 C13 O2 -28.9(3) . . . .
Br1 C12 C13 N1 154.53(19) . . . .
O1 C7 C8 C12 -134.0(3) . . . .
N1 C5 C6 C7 -55.5(3) . . . .
C1 C2 C3 C4 176.5(2) . . . .
C1 C2 C3 C11 -2.3(4) . . . .
C1 C9 C10 C11 2.4(4) . . . .
C1 C9 C10 C14 -173.1(3) . . . .
C2 C1 C9 C10 3.0(4) . . . .
C2 C3 C4 C5 -171.7(2) . . . .
C2 C3 C11 N1 -177.0(2) . . . .
C2 C3 C11 C10 8.0(4) . . . .
C3 C4 C5 N1 -14.9(3) . . . .
C3 C4 C5 C6 103.0(2) . . . .
C4 C3 C11 N1 4.0(3) . . . .
C4 C3 C11 C10 -171.0(2) . . . .
C4 C5 C6 C7 -171.2(2) . . . .
C5 N1 C11 C3 -14.2(3) . . . .
C5 N1 C11 C10 160.3(3) . . . .
C5 N1 C13 O2 155.0(3) . . . .
C5 N1 C13 C12 -28.6(3) . . . .
C5 C6 C7 O1 162.9(3) . . . .
C5 C6 C7 C8 -20.8(3) . . . .
C6 C7 C8 C12 49.6(4) . . . .
C7 C8 C12 Br1 179.1(2) . . . .
C7 C8 C12 C13 6.7(5) . . . .
C8 C12 C13 O2 143.9(3) . . . .
C8 C12 C13 N1 -32.7(4) . . . .
C9 C1 C2 C3 -3.0(4) . . . .
C9 C10 C11 N1 178.3(2) . . . .
C9 C10 C11 C3 -7.8(4) . . . .
C11 N1 C5 C4 18.1(3) . . . .
C11 N1 C5 C6 -105.0(3) . . . .
C11 N1 C13 O2 -2.5(4) . . . .
C11 N1 C13 C12 173.9(2) . . . .
C11 C3 C4 C5 7.2(3) . . . .
C13 N1 C5 C4 -142.7(2) . . . .
C13 N1 C5 C6 94.1(3) . . . .
C13 N1 C11 C3 145.5(2) . . . .
C13 N1 C11 C10 -40.0(4) . . . .
C14 C10 C11 N1 -6.4(4) . . . .
C14 C10 C11 C3 167.5(2) . . . .
