#------------------------------------------------------------------------------
#$Date: 2022-03-16 10:51:57 +0200 (Wed, 16 Mar 2022) $
#$Revision: 273720 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/47/8104760.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_8104760
loop_
_publ_author_name
'Ke, Yu-Jing'
'Liang, Peng-Jie'
'Wang, Peng-Cheng'
'Xian, Shao-Hua'
'Li, Guo-Qiang'
_publ_section_title
;
 Crystal structure of
 9-methyl-3-methylene-1,2,3,9-tetrahydro-4H-carbazol-4-one, C14H13NO
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              541
_journal_page_last               542
_journal_paper_doi               10.1515/ncrs-2020-0617
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C14 H13 N O'
_chemical_formula_sum            'C14 H13 N O'
_chemical_formula_weight         211.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 98.199(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2770(7)
_cell_length_b                   8.4582(6)
_cell_length_c                   13.4430(12)
_cell_measurement_reflns_used    2146
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.1940
_cell_measurement_theta_min      2.8500
_cell_volume                     1044.05(14)
_computing_cell_refinement
;        
CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)[1]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)[1]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)[2]'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)[2]'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -59.00  36.00   1.00    3.00    --   11.90 -57.00 -30.00   95
  2  ω    -14.00  78.00   1.00    3.00    --   11.90  57.00 120.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0181700000
_diffrn_orient_matrix_UB_12      0.0090764000
_diffrn_orient_matrix_UB_13      0.0528048000
_diffrn_orient_matrix_UB_21      -0.0747498000
_diffrn_orient_matrix_UB_22      -0.0052950000
_diffrn_orient_matrix_UB_23      0.0054438000
_diffrn_orient_matrix_UB_31      0.0066728000
_diffrn_orient_matrix_UB_32      -0.0831569000
_diffrn_orient_matrix_UB_33      0.0053981000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5167
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.469
_diffrn_reflns_theta_min         2.509
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0484
_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)+(0.0443P)²+0.3486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1151
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1972
_reflns_number_total             2462
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0617_suppl.cif
_cod_data_source_block           tb-a-1
_cod_database_code               8104760
_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   0.991
_shelx_estimated_absorpt_t_min   0.989
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
O1 O 0.61090(11) -0.00383(12) 0.24068(8) 0.0211(3) Uani 1 1 d . . . . .
N1 N 0.46948(12) 0.30457(14) -0.03918(9) 0.0155(3) Uani 1 1 d . . . . .
C2 C 0.58035(15) 0.21320(16) 0.00686(11) 0.0153(3) Uani 1 1 d . . . . .
C3 C 0.71485(16) 0.17327(18) -0.03569(12) 0.0183(3) Uani 1 1 d . . . . .
H3A H 0.7434 0.2611 -0.0750 0.022 Uiso 1 1 calc R . . . .
H3B H 0.6984 0.0815 -0.0791 0.022 Uiso 1 1 calc R . . . .
C4 C 0.83483(16) 0.13829(18) 0.05277(12) 0.0210(4) Uani 1 1 d . . . . .
H4A H 0.9193 0.0959 0.0270 0.025 Uiso 1 1 calc R . . . .
H4B H 0.8637 0.2363 0.0875 0.025 Uiso 1 1 calc R . . . .
C5 C 0.78621(15) 0.02261(17) 0.12629(11) 0.0174(3) Uani 1 1 d . . . . .
C6 C 0.64345(15) 0.05667(17) 0.16308(11) 0.0160(3) Uani 1 1 d . . . . .
C7 C 0.54889(15) 0.16382(17) 0.10003(11) 0.0153(3) Uani 1 1 d . . . . .
C8 C 0.40946(15) 0.23055(17) 0.11246(11) 0.0154(3) Uani 1 1 d . . . . .
C9 C 0.32278(15) 0.22991(18) 0.18935(12) 0.0176(3) Uani 1 1 d . . . . .
H9 H 0.3501 0.1721 0.2479 0.021 Uiso 1 1 calc R . . . .
C10 C 0.19524(16) 0.31725(18) 0.17644(12) 0.0205(4) Uani 1 1 d . . . . .
H10 H 0.1371 0.3191 0.2274 0.025 Uiso 1 1 calc R . . . .
C11 C 0.15221(15) 0.40280(18) 0.08799(12) 0.0204(3) Uani 1 1 d . . . . .
H11 H 0.0663 0.4609 0.0818 0.025 Uiso 1 1 calc R . . . .
C12 C 0.23392(15) 0.40323(17) 0.00979(12) 0.0184(3) Uani 1 1 d . . . . .
H12 H 0.2039 0.4580 -0.0495 0.022 Uiso 1 1 calc R . . . .
C13 C 0.36371(15) 0.31760(17) 0.02408(11) 0.0158(3) Uani 1 1 d . . . . .
C14 C 0.45844(16) 0.37296(18) -0.13946(11) 0.0187(3) Uani 1 1 d . . . . .
H14A H 0.5526 0.4095 -0.1511 0.028 Uiso 1 1 calc GR . . . .
H14B H 0.3916 0.4602 -0.1448 0.028 Uiso 1 1 calc GR . . . .
H14C H 0.4239 0.2942 -0.1886 0.028 Uiso 1 1 calc GR . . . .
C15 C 0.86253(17) -0.1047(2) 0.15992(13) 0.0223(4) Uani 1 1 d . . . . .
H15A H 0.956(2) -0.128(2) 0.1372(14) 0.028(5) Uiso 1 1 d . . . . .
H15B H 0.8270(19) -0.177(2) 0.2101(14) 0.029(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
C2 N1 C13 108.65(12) . .
C2 N1 C14 126.46(13) . .
C13 N1 C14 124.84(12) . .
N1 C2 C3 125.16(14) . .
N1 C2 C7 109.74(13) . .
C7 C2 C3 125.10(13) . .
C2 C3 C4 107.55(13) . .
C5 C4 C3 112.42(12) . .
C4 C5 C6 116.82(12) . .
C15 C5 C4 123.63(14) . .
C15 C5 C6 119.54(14) . .
O1 C6 C5 121.97(13) . .
O1 C6 C7 123.50(13) . .
C7 C6 C5 114.53(13) . .
C2 C7 C6 121.86(13) . .
C2 C7 C8 107.08(13) . .
C8 C7 C6 130.94(14) . .
C9 C8 C7 134.77(14) . .
C9 C8 C13 119.29(13) . .
C13 C8 C7 105.89(13) . .
C10 C9 C8 118.48(14) . .
C9 C10 C11 121.14(15) . .
C12 C11 C10 121.78(14) . .
C11 C12 C13 116.78(14) . .
N1 C13 C8 108.64(12) . .
N1 C13 C12 128.84(14) . .
C12 C13 C8 122.50(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.2374(18) .
N1 C2 1.3625(18) .
N1 C13 1.3915(19) .
N1 C14 1.4570(19) .
C2 C3 1.484(2) .
C2 C7 1.390(2) .
C3 C4 1.537(2) .
C4 C5 1.505(2) .
C5 C6 1.506(2) .
C5 C15 1.332(2) .
C6 C7 1.448(2) .
C7 C8 1.4427(19) .
C8 C9 1.397(2) .
C8 C13 1.411(2) .
C9 C10 1.385(2) .
C10 C11 1.401(2) .
C11 C12 1.381(2) .
C12 C13 1.395(2) .
