#------------------------------------------------------------------------------
#$Date: 2019-11-04 14:06:35 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222965 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/44/4034447.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_4034447
loop_
_publ_author_name
'Synofzik, Judith'
'Dar'in, Dmitry'
'Novikov, Mikhail S.'
'Kantin, Grigory'
'Bakulina, Olga'
'Krasavin, Mikhail'
_publ_section_title
;
 α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12101
_journal_page_last               12110
_journal_paper_doi               10.1021/acs.joc.9b02030
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C19 H18 N2 O3'
_chemical_formula_sum            'C19 H18 N2 O3'
_chemical_formula_weight         322.37
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-07-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.369(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6492(4)
_cell_length_b                   8.7038(4)
_cell_length_c                   14.8276(7)
_cell_measurement_reflns_used    4821
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.1830
_cell_measurement_theta_min      4.0970
_cell_volume                     1581.39(12)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.9984
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10062
_diffrn_reflns_theta_full        72.4819
_diffrn_reflns_theta_max         72.48
_diffrn_reflns_theta_min         4.12
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72789
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear yellowish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.3539
_exptl_crystal_description       needle
_exptl_crystal_F_000             682.2353
_refine_diff_density_max         0.3352
_refine_diff_density_min         -0.2887
_refine_diff_density_rms         0.0579
_refine_ls_d_res_high            0.8084
_refine_ls_d_res_low             10.7292
_refine_ls_goodness_of_fit_ref   1.0359
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0359
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0644P)²+0.4919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1144
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -15
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -9
_reflns_number_gt                2679
_reflns_number_total             3126
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b02030_si_004.cif
_cod_data_source_block           1ver0-13522-KPZ124
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               4034447
_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:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C11(H11a,H11b), C13(H13a,H13b)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C16(H16), C17(H17), C18(H18), C19(H19)
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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
O1 O 0.16668(8) 0.20184(12) 0.66434(8) 0.0211(2) Uani 1.000000 .
O2 O 0.39331(7) 0.31024(11) 0.62803(7) 0.0165(2) Uani 1.000000 .
O3 O 0.40092(8) 0.18421(12) 0.49737(7) 0.0201(2) Uani 1.000000 .
N1 N 0.31384(9) 0.05538(14) 0.75040(8) 0.0165(3) Uani 1.000000 .
N2 N 0.28686(10) -0.28077(15) 0.45012(9) 0.0234(3) Uani 1.000000 .
C1 C 0.24825(10) 0.12388(16) 0.67506(10) 0.0165(3) Uani 1.000000 .
C2 C 0.31736(10) 0.06313(15) 0.60907(9) 0.0140(3) Uani 1.000000 .
C3 C 0.39218(10) -0.00731(16) 0.70204(9) 0.0142(3) Uani 1.000000 .
H3 H 0.38987(10) -0.12215(16) 0.70078(9) 0.0171(3) Uiso 1.000000 R
C4 C 0.50653(10) 0.05032(16) 0.74110(9) 0.0146(3) Uani 1.000000 .
C5 C 0.58862(11) 0.00923(16) 0.69771(10) 0.0167(3) Uani 1.000000 .
H5 H 0.57126(11) -0.05155(16) 0.64278(10) 0.0201(3) Uiso 1.000000 R
C6 C 0.69548(11) 0.05676(18) 0.73442(11) 0.0206(3) Uani 1.000000 .
H6 H 0.75095(11) 0.02964(18) 0.70432(11) 0.0247(4) Uiso 1.000000 R
C7 C 0.72084(11) 0.14400(18) 0.81522(11) 0.0232(3) Uani 1.000000 .
H7 H 0.79384(11) 0.17652(18) 0.84077(11) 0.0278(4) Uiso 1.000000 R
C8 C 0.63948(11) 0.18363(18) 0.85860(11) 0.0227(3) Uani 1.000000 .
H8 H 0.65766(11) 0.24251(18) 0.91426(11) 0.0273(4) Uiso 1.000000 R
C9 C 0.53120(11) 0.13872(16) 0.82211(10) 0.0177(3) Uani 1.000000 .
C10 C 0.44430(12) 0.19219(19) 0.86958(11) 0.0234(3) Uani 1.000000 .
H10a H 0.47609(12) 0.19502(19) 0.93767(11) 0.0280(4) Uiso 1.000000 R
H10b H 0.42230(12) 0.29820(19) 0.84894(11) 0.0280(4) Uiso 1.000000 R
C11 C 0.34269(11) 0.09013(18) 0.84942(10) 0.0212(3) Uani 1.000000 .
H11a H 0.28172(11) 0.14416(18) 0.86674(10) 0.0255(4) Uiso 1.000000 R
H11b H 0.35787(11) -0.00598(18) 0.88606(10) 0.0255(4) Uiso 1.000000 R
C12 C 0.37436(9) 0.19153(15) 0.56984(9) 0.0139(3) Uani 1.000000 .
C13 C 0.45830(11) 0.43583(16) 0.60384(11) 0.0193(3) Uani 1.000000 .
H13a H 0.52509(11) 0.39526(16) 0.58893(11) 0.0232(4) Uiso 1.000000 R
H13b H 0.41553(11) 0.49314(16) 0.54920(11) 0.0232(4) Uiso 1.000000 R
C14 C 0.48733(11) 0.53839(18) 0.68779(11) 0.0231(3) Uani 1.000000 .
H14a H 0.5280(9) 0.6276(7) 0.6742(3) 0.0347(5) Uiso 1.000000 GR
H14b H 0.42044(12) 0.5731(12) 0.7036(5) 0.0347(5) Uiso 1.000000 GR
H14c H 0.5325(8) 0.4814(4) 0.7404(3) 0.0347(5) Uiso 1.000000 GR
C15 C 0.26455(10) -0.05221(16) 0.53641(9) 0.0153(3) Uani 1.000000 .
C16 C 0.32651(11) -0.16947(17) 0.51083(10) 0.0188(3) Uani 1.000000 .
H16 H 0.40270(11) -0.16999(17) 0.53879(10) 0.0225(4) Uiso 1.000000 R
C17 C 0.15364(11) -0.04842(17) 0.49314(10) 0.0184(3) Uani 1.000000 .
H17 H 0.10809(11) 0.02971(17) 0.50769(10) 0.0221(4) Uiso 1.000000 R
C18 C 0.11070(11) -0.16221(19) 0.42775(10) 0.0233(3) Uani 1.000000 .
H18 H 0.03552(11) -0.16200(19) 0.39619(10) 0.0279(4) Uiso 1.000000 R
C19 C 0.17973(12) -0.27510(18) 0.40987(11) 0.0236(3) Uani 1.000000 .
H19 H 0.14934(12) -0.35327(18) 0.36644(11) 0.0283(4) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C13 O2 C12 116.28(11)
C3 N1 C1 96.35(11)
C11 N1 C1 133.68(12)
C11 N1 C3 122.75(11)
C19 N2 C16 116.34(13)
N1 C1 O1 133.03(14)
C2 C1 O1 134.43(13)
C2 C1 N1 92.54(10)
C3 C2 C1 83.82(10)
C12 C2 C1 112.58(11)
C12 C2 C3 112.23(10)
C15 C2 C1 117.28(10)
C15 C2 C3 115.30(11)
C15 C2 C12 112.65(11)
C2 C3 N1 87.21(9)
C4 C3 N1 112.94(11)
C4 C3 C2 120.94(11)
C5 C4 C3 119.39(12)
C9 C4 C3 120.24(12)
C9 C4 C5 120.32(12)
C6 C5 C4 120.36(13)
C7 C6 C5 119.70(13)
C8 C7 C6 119.86(13)
C9 C8 C7 121.33(14)
C8 C9 C4 118.42(13)
C10 C9 C4 122.36(12)
C10 C9 C8 119.18(13)
C11 C10 C9 113.67(12)
C10 C11 N1 107.84(12)
O3 C12 O2 125.10(12)
C2 C12 O2 110.42(11)
C2 C12 O3 124.45(12)
C14 C13 O2 106.10(12)
C16 C15 C2 120.25(11)
C17 C15 C2 122.21(13)
C17 C15 C16 117.53(13)
C15 C16 N2 124.93(13)
C18 C17 C15 118.48(14)
C19 C18 C17 118.76(13)
C18 C19 N2 123.91(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2120(17)
O2 C12 1.3292(17)
O2 C13 1.4648(16)
O3 C12 1.2045(17)
N1 C1 1.3534(19)
N1 C3 1.4651(16)
N1 C11 1.4541(18)
N2 C16 1.333(2)
N2 C19 1.339(2)
C1 C2 1.5574(18)
C2 C3 1.5887(18)
C2 C12 1.5217(18)
C2 C15 1.5025(18)
C3 C4 1.5046(17)
C4 C5 1.3971(19)
C4 C9 1.395(2)
C5 C6 1.3890(19)
C6 C7 1.387(2)
C7 C8 1.386(2)
C8 C9 1.3976(19)
C9 C10 1.5180(19)
C10 C11 1.530(2)
C13 C14 1.502(2)
C15 C16 1.395(2)
C15 C17 1.3907(18)
C17 C18 1.398(2)
C18 C19 1.383(2)
