#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/91/2219107.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2219107
loop_
_publ_author_name
'Alhashimy, Nameer'
'Müller-Bunz, Helge'
'Schazmann, Benjamin'
'Diamond, Dermot'
_publ_section_title
;
 5',6-Dichloro-1',3',3'-trimethylspiro[2H-1-benzopyran-2,2'-indoline]
;
_journal_coeditor_code           NC2106
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1430
_journal_page_last               o1431
_journal_paper_doi               10.1107/S1600536808018722
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C19 H17 Cl2 N O'
_chemical_formula_moiety         'C19 H17 Cl2 N O'
_chemical_formula_sum            'C19 H17 Cl2 N O'
_chemical_formula_weight         346.24
_chemical_name_systematic
;
5',6-Dichloro-1',3',3'-trimethylspiro[2H-1-benzopyran-2,2'-indoline]
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.770(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3105(7)
_cell_length_b                   18.2576(16)
_cell_length_c                   11.1921(10)
_cell_measurement_reflns_used    7373
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.72
_cell_measurement_theta_min      2.19
_cell_volume                     1642.1(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'publCIF (Westrip, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16175
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.7398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.961
_refine_diff_density_min         -0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0653P)²+1.2622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1223
_reflns_number_gt                3857
_reflns_number_total             4312
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2106.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2219107
_cod_database_fobs_code          2219107
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Cl Cl1 1.29108(6) 0.46363(2) 0.01666(4) 0.02892(13) Uani d 1
C C1 1.2126(2) 0.38771(9) 0.07835(15) 0.0198(3) Uani d 1
C C2 1.0760(2) 0.39650(9) 0.12870(15) 0.0187(3) Uani d 1
H H2 1.029(3) 0.4437(13) 0.133(2) 0.025(5) Uiso d 1
C C3 1.01780(19) 0.33524(8) 0.17644(14) 0.0160(3) Uani d 1
C C4 1.09359(19) 0.26690(8) 0.17419(14) 0.0169(3) Uani d 1
C C5 1.2295(2) 0.25851(9) 0.12441(16) 0.0202(3) Uani d 1
H H5 1.284(3) 0.2115(12) 0.120(2) 0.020(5) Uiso d 1
C C6 1.2886(2) 0.32043(10) 0.07558(16) 0.0223(3) Uani d 1
H H6 1.381(3) 0.3155(12) 0.037(2) 0.024(5) Uiso d 1
N N 1.01339(17) 0.21423(7) 0.22743(13) 0.0186(3) Uani d 1
C C7 1.0459(2) 0.13674(9) 0.21878(17) 0.0225(3) Uani d 1
H H7A 1.015(3) 0.1214(13) 0.136(2) 0.029(6) Uiso d 1
H H7B 0.989(3) 0.1089(13) 0.271(2) 0.030(6) Uiso d 1
H H7C 1.163(3) 0.1284(14) 0.256(2) 0.038(7) Uiso d 1
C C8 0.88187(19) 0.32673(8) 0.24368(14) 0.0150(3) Uani d 1
C C9 0.9546(2) 0.34836(9) 0.37930(15) 0.0197(3) Uani d 1
H H9A 0.989(3) 0.3981(13) 0.383(2) 0.024(5) Uiso d 1
H H9B 0.870(3) 0.3426(12) 0.427(2) 0.027(6) Uiso d 1
H H9C 1.051(3) 0.3191(13) 0.419(2) 0.029(6) Uiso d 1
C C10 0.7265(2) 0.37244(10) 0.18951(16) 0.0204(3) Uani d 1
H H10A 0.687(3) 0.3635(12) 0.100(2) 0.022(5) Uiso d 1
H H10B 0.756(3) 0.4243(13) 0.202(2) 0.028(6) Uiso d 1
H H10C 0.647(3) 0.3607(12) 0.233(2) 0.023(5) Uiso d 1
C C11 0.85232(19) 0.24213(9) 0.23280(14) 0.0163(3) Uani d 1
O O 0.73274(14) 0.23176(6) 0.11246(10) 0.0178(2) Uani d 1
C C12 0.7959(2) 0.20568(9) 0.33518(15) 0.0194(3) Uani d 1
H H12 0.853(3) 0.2181(12) 0.417(2) 0.025(5) Uiso d 1
C C13 0.6788(2) 0.15405(9) 0.31410(15) 0.0200(3) Uani d 1
H H13 0.651(3) 0.1291(13) 0.381(2) 0.028(6) Uiso d 1
C C14 0.5891(2) 0.13478(8) 0.18904(15) 0.0166(3) Uani d 1
C C15 0.61892(19) 0.17667(8) 0.09238(14) 0.0147(3) Uani d 1
C C16 0.52518(19) 0.16618(9) -0.02828(14) 0.0159(3) Uani d 1
H H16 0.550(3) 0.1972(12) -0.090(2) 0.021(5) Uiso d 1
C C17 0.4051(2) 0.11154(9) -0.05435(15) 0.0185(3) Uani d 1
H H17 0.345(2) 0.1032(11) -0.1356(18) 0.014(5) Uiso d 1
C C18 0.38016(19) 0.06811(8) 0.04128(16) 0.0183(3) Uani d 1
Cl Cl2 0.23079(5) -0.00073(2) 0.00933(4) 0.02523(13) Uani d 1
C C19 0.4695(2) 0.07902(9) 0.16192(16) 0.0188(3) Uani d 1
H H19 0.452(3) 0.0512(12) 0.226(2) 0.022(5) Uiso d 1
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'
Cl Cl 0.1484 0.1585 '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_publ_flag
C6 C1 C2 122.16(15) n
C6 C1 Cl1 118.44(13) n
C2 C1 Cl1 119.41(13) n
C3 C2 C1 117.62(15) n
C3 C2 H2 121.6(14) n
C1 C2 H2 120.7(14) n
C2 C3 C4 120.77(15) n
C2 C3 C8 130.88(14) n
C4 C3 C8 108.24(13) n
N C4 C5 128.63(15) n
N C4 C3 110.00(14) n
C5 C4 C3 121.37(15) n
C4 C5 C6 118.05(15) n
C4 C5 H5 123.3(13) n
C6 C5 H5 118.6(13) n
C1 C6 C5 120.02(15) n
C1 C6 H6 120.4(13) n
C5 C6 H6 119.5(13) n
C4 N C11 108.93(13) y
C4 N C7 122.00(14) y
C11 N C7 122.46(14) y
N C7 H7A 110.4(14) n
N C7 H7B 109.9(14) n
H7A C7 H7B 112(2) n
N C7 H7C 108.0(16) n
H7A C7 H7C 112(2) n
H7B C7 H7C 104(2) n
C3 C8 C10 114.10(13) n
C3 C8 C9 107.98(13) n
C10 C8 C9 109.39(13) n
C3 C8 C11 100.63(12) n
C10 C8 C11 114.13(13) n
C9 C8 C11 110.21(13) n
C8 C9 H9A 109.3(13) n
C8 C9 H9B 110.6(13) n
H9A C9 H9B 108.9(19) n
C8 C9 H9C 112.7(14) n
H9A C9 H9C 107.3(19) n
H9B C9 H9C 107.9(19) n
C8 C10 H10A 109.9(13) n
C8 C10 H10B 108.3(14) n
H10A C10 H10B 108.3(18) n
C8 C10 H10C 107.7(14) n
H10A C10 H10C 113.3(18) n
H10B C10 H10C 109.2(19) n
N C11 O 109.47(12) n
N C11 C12 110.36(13) y
O C11 C12 111.93(13) n
N C11 C8 102.84(12) n
O C11 C8 104.77(12) y
C12 C11 C8 116.89(13) n
C15 O C11 121.79(12) n
C13 C12 C11 122.36(15) n
C13 C12 H12 120.5(14) n
C11 C12 H12 117.0(14) n
C12 C13 C14 120.98(15) n
C12 C13 H13 120.8(14) n
C14 C13 H13 118.2(14) n
C15 C14 C19 119.07(15) n
C15 C14 C13 117.73(14) n
C19 C14 C13 123.13(15) n
O C15 C16 117.17(14) n
O C15 C14 122.00(14) n
C16 C15 C14 120.72(14) n
C17 C16 C15 119.88(15) n
C17 C16 H16 123.2(13) n
C15 C16 H16 116.9(13) n
C16 C17 C18 119.23(15) n
C16 C17 H17 119.9(12) n
C18 C17 H17 120.8(12) n
C19 C18 C17 121.53(15) n
C19 C18 Cl2 118.93(13) n
C17 C18 Cl2 119.53(13) n
C18 C19 C14 119.48(15) n
C18 C19 H19 121.8(14) n
C14 C19 H19 118.7(14) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.7474(17) n
C1 C6 1.385(2) n
C1 C2 1.399(2) n
C2 C3 1.379(2) n
C2 H2 0.95(2) n
C3 C4 1.401(2) n
C3 C8 1.517(2) n
C4 N 1.388(2) n
C4 C5 1.389(2) n
C5 C6 1.398(2) n
C5 H5 0.98(2) n
C6 H6 0.98(2) n
N C11 1.448(2) y
N C7 1.448(2) n
C7 H7A 0.94(2) n
C7 H7B 0.98(2) n
C7 H7C 0.96(3) n
C8 C10 1.527(2) n
C8 C9 1.535(2) n
C8 C11 1.564(2) n
C9 H9A 0.95(2) n
C9 H9B 1.00(2) n
C9 H9C 0.97(2) n
C10 H10A 0.98(2) n
C10 H10B 0.98(2) n
C10 H10C 0.94(2) n
C11 O 1.4680(18) y
C11 C12 1.500(2) n
O C15 1.3596(18) n
C12 C13 1.332(2) n
C12 H12 0.94(2) n
C13 C14 1.451(2) n
C13 H13 0.95(2) n
C14 C15 1.397(2) n
C14 C19 1.401(2) n
C15 C16 1.390(2) n
C16 C17 1.389(2) n
C16 H16 0.96(2) n
C17 C18 1.389(2) n
C17 H17 0.93(2) n
C18 C19 1.379(2) n
C18 Cl2 1.7384(16) n
C19 H19 0.92(2) n
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_publ_flag
C6 C1 C2 C3 0.0(2) n
Cl1 C1 C2 C3 179.99(12) n
C1 C2 C3 C4 0.0(2) n
C1 C2 C3 C8 175.66(15) n
C2 C3 C4 N 179.88(14) n
C8 C3 C4 N 3.35(17) y
C2 C3 C4 C5 0.2(2) n
C8 C3 C4 C5 -176.36(14) n
N C4 C5 C6 179.99(16) n
C3 C4 C5 C6 -0.4(2) n
C2 C1 C6 C5 -0.2(3) n
Cl1 C1 C6 C5 179.82(13) n
C4 C5 C6 C1 0.4(3) n
C5 C4 N C11 -163.27(16) n
C3 C4 N C11 17.04(17) n
C5 C4 N C7 -11.2(3) n
C3 C4 N C7 169.10(15) n
C2 C3 C8 C10 41.2(2) n
C4 C3 C8 C10 -142.78(14) n
C2 C3 C8 C9 -80.7(2) n
C4 C3 C8 C9 95.37(15) n
C2 C3 C8 C11 163.81(16) n
C4 C3 C8 C11 -20.12(15) n
C4 N C11 O 81.89(15) n
C7 N C11 O -70.01(18) n
C4 N C11 C12 -154.49(13) n
C7 N C11 C12 53.62(19) n
C4 N C11 C8 -29.08(16) n
C7 N C11 C8 179.02(14) y
C3 C8 C11 N 28.87(14) y
C10 C8 C11 N 151.51(13) n
C9 C8 C11 N -84.95(15) n
C3 C8 C11 O -85.57(13) n
C10 C8 C11 O 37.07(17) n
C9 C8 C11 O 160.62(12) n
C3 C8 C11 C12 149.91(14) n
C10 C8 C11 C12 -87.45(17) n
C9 C8 C11 C12 36.10(19) n
N C11 O C15 102.17(16) n
C12 C11 O C15 -20.53(19) n
C8 C11 O C15 -148.14(13) n
N C11 C12 C13 -104.55(18) n
O C11 C12 C13 17.6(2) n
C8 C11 C12 C13 138.45(16) n
C11 C12 C13 C14 -5.4(3) n
C12 C13 C14 C15 -5.7(2) n
C12 C13 C14 C19 177.48(16) n
C11 O C15 C16 -172.39(13) n
C11 O C15 C14 11.3(2) n
C19 C14 C15 O 179.72(14) n
C13 C14 C15 O 2.8(2) n
C19 C14 C15 C16 3.6(2) n
C13 C14 C15 C16 -173.34(14) n
O C15 C16 C17 -178.97(14) n
C14 C15 C16 C17 -2.7(2) n
C15 C16 C17 C18 0.2(2) n
C16 C17 C18 C19 1.4(2) n
C16 C17 C18 Cl2 -179.66(12) n
C17 C18 C19 C14 -0.4(2) n
Cl2 C18 C19 C14 -179.39(12) n
C15 C14 C19 C18 -2.0(2) n
C13 C14 C19 C18 174.72(15) n
