#------------------------------------------------------------------------------
#$Date: 2019-11-17 07:48:04 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228737 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/85/1548532.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_1548532
loop_
_publ_author_name
'Joost, Maximilian'
'Transue, Wesley J.'
'Cummins, Christopher C.'
_publ_section_title
;
 Diazomethane umpolung atop anthracene: an electrophilic methylene
 transfer reagent.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              1540
_journal_page_last               1543
_journal_paper_doi               10.1039/c7sc04506a
_journal_volume                  9
_journal_year                    2018
_chemical_formula_sum            'C15 H12 N2'
_chemical_formula_weight         220.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-10-16 deposited with the CCDC.
2017-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.174(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.851(3)
_cell_length_b                   5.7145(6)
_cell_length_c                   16.970(2)
_cell_measurement_reflns_used    4668
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.43
_cell_volume                     2193.5(5)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20936
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.454
_diffrn_reflns_theta_min         1.801
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.055
_exptl_transmission_factor_max   0.7461
_exptl_transmission_factor_min   0.7006
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0474
_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)+(0.0637P)²+1.9170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1298
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2700
_reflns_number_total             3320
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7sc04506a2.cif
_cod_data_source_block           X8_16197
_cod_depositor_comments
'Adding full bibliography for 1548532--1548534.cif.'
_cod_original_cell_volume        2193.6(5)
_cod_database_code               1548532
_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_min   0.984
_shelx_estimated_absorpt_t_max   0.996
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.51761(6) 0.6387(2) 0.09477(8) 0.0221(3) Uani 1 1 d . .
H1A H 0.5005 0.4895 0.1008 0.027 Uiso 1 1 calc R U
H1B H 0.5077 0.7237 0.0466 0.027 Uiso 1 1 calc R U
N1 N 0.55384(5) 0.72505(19) 0.15141(6) 0.0202(2) Uani 1 1 d . .
N2 N 0.56716(4) 0.59558(18) 0.22091(6) 0.0162(2) Uani 1 1 d . .
C2 C 0.62866(5) 0.6454(2) 0.26266(7) 0.0157(2) Uani 1 1 d . .
H2 H 0.6385 0.8133 0.2747 0.019 Uiso 1 1 calc R U
C3 C 0.62541(5) 0.4860(2) 0.33422(7) 0.0163(2) Uani 1 1 d . .
C4 C 0.64548(5) 0.5054(2) 0.41481(7) 0.0180(2) Uani 1 1 d . .
H4 H 0.6676 0.6379 0.4355 0.022 Uiso 1 1 calc R U
C5 C 0.63223(5) 0.3243(2) 0.46514(7) 0.0204(3) Uani 1 1 d . .
H5 H 0.6458 0.3339 0.5206 0.024 Uiso 1 1 calc R U
C6 C 0.59963(5) 0.1309(2) 0.43500(7) 0.0198(2) Uani 1 1 d . .
H6 H 0.5915 0.0096 0.4701 0.024 Uiso 1 1 calc R U
C7 C 0.57852(5) 0.1121(2) 0.35328(7) 0.0175(2) Uani 1 1 d . .
H7 H 0.5557 -0.0187 0.3326 0.021 Uiso 1 1 calc R U
C8 C 0.59218(5) 0.2909(2) 0.30426(7) 0.0159(2) Uani 1 1 d . .
C9 C 0.57579(5) 0.3325(2) 0.21552(7) 0.0157(2) Uani 1 1 d . .
H9 H 0.5417 0.2405 0.1879 0.019 Uiso 1 1 calc R U
C10 C 0.63345(5) 0.3230(2) 0.17892(7) 0.0148(2) Uani 1 1 d . .
C11 C 0.65510(5) 0.1668(2) 0.12826(7) 0.0169(2) Uani 1 1 d . .
H11 H 0.6337 0.0297 0.1106 0.020 Uiso 1 1 calc R U
C12 C 0.70993(5) 0.2173(2) 0.10363(7) 0.0183(2) Uani 1 1 d . .
H12 H 0.7256 0.1135 0.0682 0.022 Uiso 1 1 calc R U
C13 C 0.74149(5) 0.4168(2) 0.13026(7) 0.0180(2) Uani 1 1 d . .
H13 H 0.7780 0.4491 0.1118 0.022 Uiso 1 1 calc R U
C14 C 0.72019(5) 0.5715(2) 0.18408(7) 0.0165(2) Uani 1 1 d . .
H14 H 0.7421 0.7061 0.2034 0.020 Uiso 1 1 calc R U
C15 C 0.66621(5) 0.5204(2) 0.20789(7) 0.0149(2) 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 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 H1A 120.0
N1 C1 H1B 120.0
H1A C1 H1B 120.0
C1 N1 N2 118.32(11)
N1 N2 C2 112.06(9)
N1 N2 C9 119.35(10)
C2 N2 C9 95.43(8)
N2 C2 C3 96.53(8)
N2 C2 C15 101.09(9)
C3 C2 C15 107.44(9)
N2 C2 H2 116.4
C3 C2 H2 116.4
C15 C2 H2 116.4
C4 C3 C8 120.54(11)
C4 C3 C2 133.70(11)
C8 C3 C2 105.69(10)
C3 C4 C5 118.22(11)
C3 C4 H4 120.9
C5 C4 H4 120.9
C6 C5 C4 120.92(11)
C6 C5 H5 119.5
C4 C5 H5 119.5
C5 C6 C7 120.99(11)
C5 C6 H6 119.5
C7 C6 H6 119.5
C8 C7 C6 117.54(11)
C8 C7 H7 121.2
C6 C7 H7 121.2
C7 C8 C3 121.78(11)
C7 C8 C9 131.94(11)
C3 C8 C9 106.24(10)
C8 C9 N2 96.36(9)
C8 C9 C10 106.91(9)
N2 C9 C10 100.68(9)
C8 C9 H9 116.7
N2 C9 H9 116.7
C10 C9 H9 116.7
C11 C10 C15 121.19(10)
C11 C10 C9 132.82(11)
C15 C10 C9 106.00(9)
C10 C11 C12 117.81(11)
C10 C11 H11 121.1
C12 C11 H11 121.1
C13 C12 C11 120.99(11)
C13 C12 H12 119.5
C11 C12 H12 119.5
C12 C13 C14 121.01(11)
C12 C13 H13 119.5
C14 C13 H13 119.5
C15 C14 C13 117.53(11)
C15 C14 H14 121.2
C13 C14 H14 121.2
C14 C15 C10 121.40(10)
C14 C15 C2 132.86(11)
C10 C15 C2 105.72(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.2753(17)
C1 H1A 0.9500
C1 H1B 0.9500
N1 N2 1.3890(14)
N2 C2 1.5082(15)
N2 C9 1.5209(16)
C2 C3 1.5282(16)
C2 C15 1.5287(16)
C2 H2 1.0000
C3 C4 1.3837(16)
C3 C8 1.4029(16)
C4 C5 1.4022(17)
C4 H4 0.9500
C5 C6 1.3889(18)
C5 H5 0.9500
C6 C7 1.4061(17)
C6 H6 0.9500
C7 C8 1.3810(16)
C7 H7 0.9500
C8 C9 1.5180(16)
C9 C10 1.5355(15)
C9 H9 1.0000
C10 C11 1.3788(16)
C10 C15 1.4036(16)
C11 C12 1.4059(16)
C11 H11 0.9500
C12 C13 1.3895(17)
C12 H12 0.9500
C13 C14 1.4070(16)
C13 H13 0.9500
C14 C15 1.3827(15)
C14 H14 0.9500
